Method for producing iodofluoroalkane compounds

Abstract

This invention provides a method for producing iodofluoroalkane compounds that improves reaction conversion rate, selectivity, and environmental impact by using more suitable reagents or operating conditions. [Solution] The present invention provides a method comprising the following steps: a) contacting a fluoroolefin with hydrogen iodide to form a flow A containing the iodofluoroalkane compound and unreacted hydrogen iodide; b) separating flow A into a first flow B1 containing the iodofluoroalkane compound and a flow B2 containing unreacted hydrogen iodide; and c) recirculating flow B2 back to step a).

Description

[Technical Field]

[0001] This invention relates to a method for producing haloalkane compounds. In particular, this invention relates to a method for producing iodofluoroalkane compounds. [Background technology]

[0002] Considering the reactivity of the iodine atom, iodofluoro compounds are important synthetic intermediates for the manufacture of pharmaceuticals, plant protection products, fire extinguishing agents, and products for processing various substrates (especially electronic application substrates).

[0003] Iodofluoro compounds are also used in the field of refrigeration and air conditioning systems. Compositions containing CF3I and HFC-152A intended for use in refrigerant compositions, refrigeration systems, expander-based compositions, aerosol propellants, etc., are known from International Publication No. 2006 / 112881.

[0004] Furthermore, French Patent Application Publication No. 2794456 discloses a method for preparing trifluoromethyl iodide or pentafluoroethyl iodide. Also, French Patent Application Publication No. 2745286 discloses a method for preparing trifluoromethyl iodide.

[0005] The process for producing iodofluoro compounds can be improved in terms of both reaction conversion rate and selectivity, as well as environmental impact, by using more suitable reagents or operating conditions. [Disclosure of the Invention]

[0006] The object of the present invention is to solve all or some of the drawbacks observed in prior art processes.

[0007] Invention I Summary of Invention I The present invention relates to a method for producing iodofluoroalkane compounds, comprising the following steps: a) Contacting a fluoroolefin with hydrogen iodide to form a stream A containing the iodo fluoroalkane compound and unreacted hydrogen iodide. b) Separating the stream A into a first stream B1 containing the iodo fluoroalkane compound and a stream B2 containing unreacted hydrogen iodide. c) Recycling the stream B2 to step a).

[0008] According to a preferred embodiment, the hydrogen iodide is anhydrous.

[0009] According to a preferred embodiment, the fluoroolefin is anhydrous.

[0010] The fact that the method is carried out under anhydrous conditions makes it possible to obtain better conversion and / or selectivity of the reaction. Also, the anhydrous operating conditions can suppress the corrosion of equipment.

[0011] According to a preferred embodiment, the fluoroolefin is of formula (I) (R 4 , 3 , 2 , 1 , 4 , 10 , 10 , 10 , 3 , 1 , 4 , 2 , 10 , 10 )(R 2 )C=C(R 3 )(R 4 ), wherein R 1 , R 2 , R 3 and R 4 are, independently of each other, H, F, Cl, I, a C1-C 10 alkyl group optionally substituted with at least one fluorine atom, a C3-C 10 cycloalkyl group optionally substituted with at least one fluorine atom, a C2-C 10 alkenyl group optionally substituted with at least one fluorine atom, a C3-C 10 cycloalkenyl group optionally substituted with at least one fluorine atom, and a C6-C 10 aryl group optionally substituted with at least one fluorine atom, provided that the substituents R 1 , R 2 , R 3 or R 4At least one of them is F or a group as described above containing at least one fluorine atom.

[0012] According to another preferred embodiment, the fluoroolefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is of the same type, and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0013] According to another preferred embodiment, the fluoroolefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is of the same type, and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , R 4 , Y1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0014] According to a preferred embodiment, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CH-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, Cl, I, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing at least one fluorine atom; or, The iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CH-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10Selected from the group consisting of perfluoroaryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 is F or a perfluoro group as described above, provided that at least one of them is F; or The iodo fluoroalkane compound is a compound of formula (II) (R 1 )(R 2 )CH-C(I)(R 3 )(R 4 ), wherein R 1 , R 2 , R 3 and R 4 are each independently H, F or Y 1 -[-C(Y 2 )(Y 3 )-] n -(wherein Y 1 , Y 2 and Y 3 are each independently and for each unit n independently selected from the group consisting of H and F, and n is an integer from 1 to 5), provided that the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 is F.

[0015] According to a preferred embodiment, the fluoroolefin is CHF=CH2, CF2=CH2, CHF=CHF, CF2=CHF, CF2=CF2, CH3-CF=CH2, CH3-CH=CHF, CH2F-CH=CH2, CH3-CF=CHF, CH2F-CF=CH2, CH3-CH=CF2, CH2F-CH=CHF, CHF2-CH=CH2, CH3-CF=CF2, CH2F-CF=CHF, CHF2-CF=CH2, CH2F-CH=CF2, CHF2-CH=CHF, CF Selected from the group consisting of 3-CH=CH2, CH2F-CF=CF2, CHF2-CF=CHF, CF3-CF=CH2, CHF2-CH=CF2, CF3-CH=CHF, CHF2-CF=CF2, CF3-CF=CHF, CF3-CH=CF2, CF3-CF=CF2, and selected from the group consisting of Tivoli, CF2=CH2, CF2=CHF, CF2=CF2, CF3-CH=CH2, CF3-CF=CH2, CF3-CH=CHF, CF3-CF=CHF, CF3-CF=CF2.

[0016] According to a preferred embodiment, the iodofluoroalkane compound is CH2F-CH2I, CHFI-CH3, CHF2-CH2I, CF2I-CH3, CH2F-CHFI, CHF2-CHFI, CF2I-CH2F, CHF2-CF2I, CH3-CHF-CH2I, CH3-CFI-CH3, CH3-CH2-CHFI, CH3-CHI-CH2F, CH2F-CH2-CH2I, CH3-CHF-CHFI, CH3-CFI-CH2F, CH2F-CHF-CH2 I, CH3-CH2-CF2I, CH3-CHI-CHF2, CH2F-CH2-CHFI, CH2F-CHI-CH2F, CHF2-CH2-CH2I, CH3-CHF-CF2I, CH3-CFI-CHF2, CH2F-CHF-C HFI, CH2F-CFI-CH2F, CHF2-CHF-CH2I, CH2F-CH2-CF2I, CH2F-CHI-CHF2, CHF2-CH2-CHFI, CF3-CH2-CH2I, CF3-CHI-CH3, CH2F-CHF -CF2I, CH2F-CFI-CHF2, CHF2-CHF-CHFI, CF3-CHF-CH2I, CF3-CFI-CH3, CHF2-CH2-CF2I, CHF2-CHI-CHF2, CF3-CH2-CHFI, CF3-CH I-CH2F, CHF2-CHF-CF2I, CHF2-CFI-CHF2, CF3-CHF-CHFI, CF3-CFI-CH2F, CF3-CH2-CF2I, CF3-CHI-CHF2, CF3-CHF-CF2I, CF3-CF Selected from the group consisting of I-CHF2, preferably from the group consisting of CHF2-CH2I, CF2I-CH3, CHF2-CHFI, CF2I-CH2F, CHF2-CF2I, CF3-CH2-CH2I, CF3-CHI-CH3, CF3-CHF-CH2I, CF3-CFI-CH3, CF3-CH2-CHFI, CF3-CHI-CH2F, CF3-CHF-CHFI, CF3-CFI-CH2F, CF3-CHF-CF2I, and CF3-CFI-CHF2.

[0017] According to a preferred embodiment, step a) includes: - Converting CF2=CH2 to CF2I-CH3; or - Converting CF2=CHF to CF2I-CH2F; or - Converting CF2=CF2 to CHF2-CF2I; or - Converting CF3-CH=CH2 to CF3-CH2-CH2; or - Converting CF3-CF=CH2 to CF3-CFI-CH3; or - Converting CF3-CH=CHF to CF3-CH2-CHFI; or - Converting CF3-CF=CHF to CF3-CHF-CHFI; or - Convert CF3-CF=CF2 to CF3-CHF-CF2I.

[0018] According to a preferred embodiment, the fluoroolefin has a boiling point of less than 100°C at atmospheric pressure.

[0019] According to a preferred embodiment, step a) is carried out in the gas phase in the presence of an oxide, oxyhalide, or halide of a metal from groups 4 to 12 of the periodic table, or a catalyst selected from the group consisting of oxides, oxyhalides, or halides of a metal selected from Li, Na, K, Cs, Mg, Ca, Al, and Sb.

[0020] According to a preferred embodiment, step a) is carried out at a temperature of 150°C to 700°C.

[0021] According to a preferred embodiment, step a) is carried out in the liquid phase in the presence of solvent S1 and a catalyst selected from alkali metal salts or alkaline earth metal salts.

[0022] According to a preferred embodiment, step a) is carried out in the presence of a solvent S1 having a boiling point between 20°C and 250°C.

[0023] Detailed description of Invention I The present invention relates to a method for producing iodofluoroalkane compounds. The method particularly includes contacting a fluoroolefin with hydrogen iodide to form a flow A containing the iodofluoroalkane compound and unreacted hydrogen iodide.

[0024] The method preferably also includes a step of separating the compound contained in flow A. The method may also include a step of recirculating the starting reagent.

[0025] Therefore, the method includes the following steps: a) A step of contacting a fluoroolefin with hydrogen iodide to form a flow A containing the iodofluoroalkane compound and unreacted hydrogen iodide. b) A step of separating the flow A into a first flow B1 containing the iodofluoroalkane compound and a flow B2 containing unreacted hydrogen iodide. c) A process to recirculate flow B2 back to process a).

[0026] Step a) of this method In step a) of this method, it is necessary to bring the fluoroolefin into contact with hydrogen iodide (HI).

[0027] The fluoroolefin is preferably of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) is of the same type, and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, Cl, I, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4At least one of them is F or a group as described above containing at least one fluorine atom.

[0028] The term "alkyl" refers to a monovalent group derived from linear or branched alkanes containing a specific number of carbon atoms. The term "cycloalkyl" refers to a monovalent group derived from cycloalkanes containing a specific number of carbon atoms. The term "alkenyl" refers to a monovalent group containing a specific number of carbon atoms and at least one carbon-carbon double bond. The term "cycloalkenyl" refers to a monovalent group derived from cycloalkenes containing a specific number of carbon atoms and at least one carbon-carbon double bond in the cyclic portion. The term "aryl" refers to a monovalent group derived from arenes containing a specific number of carbon atoms.

[0029] Preferably, the alkyl, cycloalkyl, alkenyl, cycloalkenyl, or aryl group is not substituted with a functional group other than fluorine. Nevertheless, the group may contain several fluorine atoms on its carbon chain, for example, 1 to 10 fluorine atoms, preferably 1 to 5 fluorine atoms.

[0030] Preferably, the fluoroolefin is of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) is of the same type, and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, I, and 1 to 10 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0031] Preferably, the fluoroolefin is of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) is of the same type, and in the formula, R 1 , R 2 , R 3 and R 4 The C1-C atoms may be independently substituted with H, F, I, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0032] Preferably, the fluoroolefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is of the same type, and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0033] Preferably, the fluoroolefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is of the same type, and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0034] Alternatively, the fluoroolefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is of the same type, and in the formula, R 1 , R 2 , R 3 and R 4 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F, where n is an integer from 1 to 10. 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0035] The aforementioned fluoroolefin is formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) may be of the same nature, and in the formula, R 1 , R 2 , R 3 and R 4 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F (where n is an integer from 1 to 5), however, the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0036] The aforementioned fluoroolefin is formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) may be of the same nature, and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3)-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 10, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F. The aforementioned fluoroolefin is formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) may be of the same nature, and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0037] In particular, the fluoroolefin is selected from the group consisting of CHF=CH2, CF2=CH2, CHF=CHF, CF2=CHF, CF2=CF2, CH3-CF=CH2, CH3-CH=CHF, CH2F-CH=CH2, CH3-CF=CHF, CH2F-CF=CH2, CH3-CH=CF2, CH2F-CH=CHF, CHF2-CH=CH2, CH3-CF=CF2, CH2F-CF=CHF, CHF2-CF=CH2, CH2F-CH=CF2, CHF2-CH=CHF, CF3-CH=CH2, CH2F-CF=CF2, CHF2-CF=CHF, CF3-CF=CH2, CHF2-CH=CF2, CF3-CH=CHF, CHF2-CF=CF2, CF3-CF=CHF, CF3-CH=CF2, CF3-CF=CF2.

[0038] More specifically, the fluoroolefin is selected from the group consisting of CF2=CH2, CF2=CHF, CF2=CF2, CF3-CH=CH2, CF3-CF=CH2, CF3-CH=CHF, CF3-CF=CHF, and CF3-CF=CF2.

[0039] Preferably, step a) is carried out in the presence of anhydrous fluoroolefin. Herein, “anhydrous” means a fluoroolefin containing less than 500 ppm of water, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, more precisely less than 10 ppm, preferably less than 5 ppm, and preferentially, the fluoroolefin is water-free. The use of anhydrous fluoroolefin in this method makes it possible to avoid the formation of impurities (such as reaction by-products and polymers derived from fluoroolefins).

[0040] The fluoroolefin may have a boiling point of less than 100°C at atmospheric pressure. Advantageously, the fluoroolefin has a boiling point of less than 75°C at atmospheric pressure. Preferably, the fluoroolefin has a boiling point of less than 50°C at atmospheric pressure. More preferably, the fluoroolefin has a boiling point of less than 25°C at atmospheric pressure. In particular, the fluoroolefin has a boiling point of less than 10°C at atmospheric pressure.

[0041] In step a), the fluoroolefin is brought into contact with hydrogen iodide (HI). Preferably, the hydrogen iodide is also anhydrous. Here, the term “anhydrous” refers to hydrogen iodide containing less than 500 ppm of water, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, more precisely less than 10 ppm, preferably less than 5 ppm, and preferably, the hydrogen iodide is water-free. The use of anhydrous hydrogen iodide in this method also prevents the formation of the impurities described above. The use of anhydrous fluoroolefin and anhydrous hydrogen iodide makes it possible to achieve particularly advantageous selectivity at an industrial level.

[0042] Preferably, hydrogen iodide is brought into contact with the fluoroolefin in a stoichiometric or greater amount. For example, the molar ratio of HI / fluoroolefin is 1 to 50, preferably 2 to 25, and particularly 5 to 20.

[0043] Preferably, hydrogen iodide is prepared by contacting hydrogen (H2) with iodine (I2). In particular, hydrogen iodide is prepared by contacting anhydrous hydrogen with anhydrous iodine. The term "anhydrous" refers to the same definition as given above for hydrogen iodide.

[0044] Alternatively, hydrogen iodide may be deficient relative to the fluoroolefin. In that case, flows A and B2 contain the unreacted fluoroolefin instead of unreacted hydrogen iodide. Therefore, the compound recycled to step a) is the fluoroolefin.

[0045] As described above, step a) forms a flow A containing the iodofluoroalkane compound and unreacted hydrogen iodide.

[0046] The iodofluoroalkane compound formed is preferably of formula (II)(R 1 )(R 2 )CH-C(I)(R 3 )(R4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, Cl, I, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing at least one fluorine atom.

[0047] Preferably, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CH-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, I, and 1 to 10 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R3 or R 4 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0048] Preferably, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CH-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 The C1-C atoms may be independently substituted with H, F, I, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0049] According to a preferred embodiment, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CH-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0050] Preferably, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CH-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0051] According to another preferred embodiment, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CH-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F, where n is an integer from 1 to 10. 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0052] Preferably, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CH-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0053] The iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CH-C(I)(R 3 )(R 4 ) may be a compound of the same type, where R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1-[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 10, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0054] The iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CH-C(I)(R 3 )(R 4 ) may be a compound of the same type, where R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0055] In particular, the iodofluoroalkane compounds include CH2F-CH2I, CHFI-CH3, CHF2-CH2I, CF2I-CH3, CH2F-CHFI, CHF2-CHFI, CF2I-CH2F, CHF2-CF2I, CH3-CHF-CH2I, CH3-CFI-CH3, CH3-CH2-CHFI, CH3-CHI-CH2F, CH2F-CH2-CH2I, CH3-CHF-CHFI, CH3-CFI-CH2F, CH2F-CHF-CH2I, CH3-CH2-CF2I, CH3-CHI-CHF2, CH2F-CH2-CHFI, CH2F-CHI-CH2F, CHF2-CH2-CH2I, CH3-CHF-CF2I, CH3-CFI-CHF2, CH2F-CHF-CHFI, CH2F-CFI-CH 2F, CHF2-CHF-CH2I, CH2F-CH2-CF2I, CH2F-CHI-CHF2, CHF2-CH2-CHFI, CF3-CH2-CH2I, CF3-CHI- CH3, CH2F-CHF-CF2I, CH2F-CFI-CHF2, CHF2-CHF-CHFI, CF3-CHF-CH2I, CF3-CFI-CH3, CHF2-CH2-C F2I, CHF2-CHI-CHF2, CF3-CH2-CHFI, CF3-CHI-CH2F, CHF2-CHF-CF2I, CHF2-CFI-CHF2, CF3-CHF-C HFI, CF3-CFI-CH2F, CF3-CH2-CF2I, CF3-CHI-CHF2, CF3-CHF-CF2I, CF3-CFI-CHF2.

[0056] More specifically, the iodofluoroalkane is selected from the group consisting of CHF2-CH2I, CF2I-CH3, CHF2-CHFI, CF2I-CH2F, CHF2-CF2I, CF3-CH2-CH2I, CF3-CHI-CH3, CF3-CHF-CH2I, CF3-CFI-CH3, CF3-CH2-CHFI, CF3-CHI-CH2F, CF3-CHF-CHFI, CF3-CFI-CH2F, CF3-CHF-CF2I, and CF3-CFI-CHF2.

[0057] In a particularly preferred method, step a) of this manufacturing method includes: - Converting CF2=CH2 to CF2I-CH3; or - Converting CF2=CHF to CF2I-CH2F; or - Converting CF2=CF2 to CHF2-CF2I; or - Converting CF3-CH=CH2 to CF3-CH2-CH2; or - Converting CF3-CF=CH2 to CF3-CFI-CH3; or - Converting CF3-CH=CHF to CF3-CH2-CHFI; or - Converting CF3-CF=CHF to CF3-CHF-CHFI; or - Convert CF3-CF=CF2 to CF3-CHF-CF2I.

[0058] Step a) can be carried out in the liquid phase or the gas phase. Step a) can be carried out in or without the catalyst.

[0059] When step a) is carried out in the gas phase, it may be carried out in the presence of a catalyst. Preferably, the catalyst is selected from the group consisting of oxides, oxyhalides, or halides of metals from groups 4 to 12 of the periodic table, or oxides, oxyhalides, or halides of metals selected from Li, Na, K, Cs, Mg, Ca, Al, and Sb.

[0060] Preferably, the catalyst is chromium oxide, chromium oxyfluoride, or chromium fluoride. Chromium oxyfluoride preferably has a fluorine content of 10% to 50% by weight, preferably 20% to 50% by weight, and particularly 30% to 50% by weight. The fluorine content is measured by ion measurement, by the weight change of the catalyst, or by any other quantitative method known to those skilled in the art. The chromium oxyfluoride or chromium fluoride catalyst is preferably 15m 2 / g to 100m 2 It has a specific surface area of ​​ / g. The chromium oxide catalyst is preferably 100m 2 / g to 300m 2It has a specific surface area of ​​1 / g. The specific surface area is measured using a Micromeritics Gemini 2360 instrument with a standard 5-point method (BET method).

[0061] When the catalyst is chromium oxide, chromium oxyfluoride, or chromium fluoride, the catalyst may contain 0.5% to 10% by weight of a co-catalyst relative to the total weight of the catalyst. The co-catalyst is selected from Cr, Ni, Zn, Ti, V, Zr, Mo, Ge, Sn, Pb, and Mg.

[0062] When the metal is selected from Li, Na, K, Cs, Mg, Ca, Al, and Sb, the anion that associates with that metal is F - Cl - , I - or CO3 2- Preferably, the catalyst is NaI or KI. Preferably, the catalyst is 20m 2 / g to 1000m 2 Specific surface area between / g, especially 20m² 2 / g to 300m 2 It has a specific surface area between / g.

[0063] The catalyst may be deposited on a porous support. The porous support may be selected from activated carbon, graphite, alumina, and alumina fluoride.

[0064] When the metal of the catalyst is selected from Li, Na, K, Cs, Mg, Ca, Al, and Sb, the catalyst content is 1% to 30% by weight relative to the fluoroolefin.

[0065] If the catalyst is selected from the group consisting of oxides, oxyhalides, or halides of metals from groups 4 to 12 of the periodic table, the catalyst may be activated before use in step a). For example, the catalyst may be activated in the presence of oxygen, air, hydrogen iodide or HF, or a mixture thereof.

[0066] The catalyst may become inactive over time. Therefore, step a) may be carried out in the presence of oxygen or air, or in the presence of an oxygen-nitrogen mixture. When oxygen is used in step a), the oxygen is present in an amount of 0.005 mol% to 10 mol% relative to the molar amount of fluoroolefin.

[0067] The catalyst may also be regenerated after the method has been carried out. The regeneration step may include bringing the catalyst into contact with a flow of oxygen or air at a temperature of 200°C to 700°C.

[0068] Alternatively, step a) may be carried out in the gas phase, in the absence of the catalyst.

[0069] In the gas phase, step a) is carried out at a temperature of 150°C to 700°C, preferably 250°C to 600°C.

[0070] Regardless of whether step a) is carried out in the gas phase, in the presence or absence of the catalyst, the pressure in this step is 0.1 bar to 30 bar, preferably 1 bar to 20 bar, and particularly 1 bar to 15 bar.

[0071] Alternatively, step a) is carried out in the liquid phase. Preferably, if step a) is carried out in the liquid phase, it is carried out in the presence of solvent S1. Preferably, solvent S1 is anhydrous. The term “anhydrous” as used herein means solvent S1 containing less than 500 ppm of water, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, more precisely less than 10 ppm, preferably less than 5 ppm, and preferentially, solvent S1 does not contain water.

[0072] Solvent S1 has a boiling point of 0°C to 250°C, preferably 20°C to 250°C, and particularly 20°C to 200°C. Solvent S1 is selected from the group consisting of acetic acid, CCl4, chloroform, dichloromethane, sulfolane, tetramethylenesulfone, N,N-dimethylformamide, dimethyl sulfoxide, N,N-dimethylacetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone, and mixtures thereof.

[0073] The temperature at which step a) is carried out is 50°C to 280°C, preferably 50°C to 250°C.

[0074] Preferably, step a) in the liquid phase is carried out in the presence of a catalyst selected from alkali metal salts or alkaline earth metal salts. Preferably, the catalyst is an alkali metal salt. Any alkali metal iodide may be used, but preferably sodium iodide or potassium iodide is used. The ratio of the catalyst to the fluoroolefin is between 1 and 20, preferably between 1 and 10. The catalyst is preferably 20 ml 2 / g to 1000m 2 Specific surface area between / g, especially 20m² 2 / g to 300m 2 It has a specific surface area between / g. The catalyst may be deposited on a porous support. The porous support may be selected from activated carbon, graphite, alumina, and alumina fluoride. When the metal of the catalyst is selected from Li, Na, K, Cs, Mg, Ca, Al, and Sb, the catalyst content is 1% to 30% by weight relative to the fluoroolefin.

[0075] As described above, step a) makes it possible to obtain flow A containing the iodofluoroalkane compound and unreacted hydrogen iodide. Flow A may also contain other compounds such as impurities, reaction by-products, or unreacted fluoroolefins.

[0076] For example, if the fluoroolefin is CF2=CH2, flow A may contain CHF2-CH2I in addition to CF2I-CH3. If the fluoroolefin is CF2=CHF, flow A may contain CF3-CHFI in addition to CF2I-CH2F. If the fluoroolefin is CF3-CH=CH2, flow A may contain CF3-CHI-CH3 in addition to CF3-CH2-CH2I. If the fluoroolefin is CF3-CF=CH2, flow A may contain CF3-CHF-CH2I in addition to CF3-CFI-CH3. If the fluoroolefin is CF3-CH=CHF, flow A may contain CF3-CHI-CH2F in addition to CF3-CH2-CHFI. If the fluoroolefin is CF3-CF=CHF, flow A may contain CF3-CFI-CH2F in addition to CF3-CHF-CHFI. If the fluoroolefin is CF3-CF=CF2, then flow A may contain CF3-CFI-CHF2 in addition to CF3-CHF-CF2I.

[0077] According to another embodiment, the method may be carried out in the presence of a mixture of fluoroolefins as described above to result in the formation of a mixture of iodofluoroalkane compounds in flow A and flow B1.

[0078] Step b) of this method Subsequently, flow A is separated to form a first flow B1 containing the iodofluoroalkane compound and a flow B2 containing unreacted hydrogen iodide. Both flow B1 and flow B2 may contain impurities, reaction by-products, or unreacted fluoroolefins. In that case, flow B1 is subjected to a further purification step to obtain a purified flow B1 containing the iodofluoroalkane compound. Preferably, after separation and possible purification steps, the content of the iodofluoroalkane compound in flow B1 is greater than 90%, advantageously greater than 92%, preferably greater than 94%, more preferably greater than 96%, particularly greater than 98%, and more precisely greater than 99%.

[0079] The flow A is preferably separated and / or purified by distillation, azeotropic distillation, pressurized distillation, extractive distillation, cold separation, absorption into a solvent, or a combination thereof.

[0080] Flow A may also be separated or purified by contact with an adsorbent. The adsorbent can be a molecular sieve or zeolite having pore openings with an average diameter between 3 angstroms and 11 angstroms, preferably between 4 angstroms and 10 angstroms, and more preferably between 5 angstroms and 10 angstroms.

[0081] Step c) of this method Step c) of this method includes recirculating flow B2 back to step a). This recirculation step improves the overall yield of the method (a better conversion rate), saves expensive reagents (and catalysts), and minimizes the environmental impact. Without this recirculation step, unreacted hydrogen iodide would have to be incinerated, thus increasing the carbon dioxide emissions of the method.

[0082] If flow B1 contains unreacted fluoroolefins, they can be removed from flow B1 and recycled back to step a).

[0083] This method may be performed continuously, or in batch or semi-batch form.

[0084] Preferably, in order to avoid corrosion problems, the reactor in which step a) is carried out is made of a material that includes a base layer made of material M1 and an inner layer made of material M2.

[0085] Advantageously, material M2 contains at least 40% by weight of nickel relative to the total weight of material M2. Preferably, material M2 contains at least 45% by weight of nickel, more preferably at least 50% by weight of nickel, particularly at least 55% by weight of nickel, especially at least 60% by weight of nickel, preferably at least 65% by weight of nickel, and more preferably at least 70% by weight of nickel relative to the total weight of material M2.

[0086] Material M2 also contains chromium in an amount of less than 35% by weight, preferably less than 30% by weight, preferably less than 20% by weight, more preferably less than 15% by weight, particularly less than 10% by weight, and especially less than 5% by weight relative to the total weight of Material M2.

[0087] Material M2 also contains molybdenum in an amount of less than 35% by weight, preferably less than 30% by weight, preferably less than 20% by weight, more preferably less than 15% by weight, particularly less than 10% by weight, and especially less than 5% by weight, relative to the total weight of Material M2.

[0088] Preferably, material M2 is Monel®, Hastelloy®, Inconel®, or Incoloy®.

[0089] According to a preferred embodiment, the material M1 comprises at least 70% by weight of iron, advantageously at least 75% by weight, preferably at least 80% by weight, more preferably at least 85% by weight, particularly at least 90% by weight, and especially at least 95% by weight, based on the total weight of the material M1.

[0090] Material M1 may also contain less than 2% by weight, advantageously less than 1.5% by weight, preferably less than 1% by weight, more preferably less than 0.75% by weight, particularly less than 0.5% by weight, especially less than 0.2% by weight, and preferably less than 0.1% by weight of carbon relative to the total weight of Material M1. More specifically, Material M1 may contain between 0.01% and 0.2% by weight of carbon based on the total weight of Material M1.

[0091] Preferably, the base layer and the inner layer are arranged to face each other by molten or low-temperature plating, hot or cold rolling, or pressure welding.

[0092] Examples Example 1 250 mL of sulfolane and 0.1 mol of sodium iodide were introduced into a 500 mL Hastelloy C276 reactor equipped with a stirrer, heater, and temperature control system. The reaction medium was heated to 90°C to 100°C while stirring. Anhydrous reagent, 0.5 mol of CF2=CHF, and 0.8 mol of HI (prepared from H2 and I2) were introduced into the reaction medium. After reacting for 4 hours with stirring, the sample was taken, washed, dried, and then analyzed by gas chromatography (area percentage method). The conversion rate of CF2=CHF was 85%, and the selectivity for CF2I-CH2F was 89%.

[0093] Example 2 A chromium oxyfluoride catalyst with a fluorine content between 15% and 20% by weight was introduced into a tubular reactor made of Inconel 600. The catalyst was pre-activated at 300°C in the presence of an O2 gas stream. A gas stream of hexafluoropropene and a gas stream of hydrogen iodide prepared from H2 and I2 (HFP / HI molar ratio = 1 / 2) were passed over the catalyst at 3 bar and 270°C. The gas was washed at the reactor outlet, then dried and condensed in a cooling trap. Samples were taken and analyzed by gas chromatography (area percentage method). The conversion rate of hexafluoropropene was 95%, and the selectivity for CF3-CHF-CF2I was 97%.

[0094] For the fluoroolefins CF3-CF=CHF, CF3-CH=CHF, CF3-CF=CH2, and CF3-CH=CH2, equivalent conversion rates and selectivity values ​​were obtained.

[0095] Invention II Summary of Invention II The present invention relates to a method for producing an iodofluoroalkane compound, comprising step a) contacting an olefin with anhydrous iodine monofluoride (IF) to form a flow A containing the iodofluoroalkane compound and optionally unreacted iodine monofluoride.

[0096] This method makes it possible to obtain iodofluoroalkane compounds with improved selectivity while maintaining a high conversion rate of the starting olefin.

[0097] According to a preferred embodiment, the olefin is a fluoroolefin.

[0098] According to a preferred embodiment, the olefin is of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 )[where R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, Cl, I, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 [A fluoroolefin is provided that at least one of them is F or a group as described above containing at least one fluorine atom.]

[0099] According to another preferred embodiment, the olefin is of formula (I)(R 1) (R 2 )C=C(R3 )(R 4 )[where R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 The fluoroolefin is provided that at least one of the elements is either F or a perfluoro group as described above.

[0100] According to another preferred embodiment, the olefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 )[where R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 It is a fluoroolefin [provided that at least one of them is F].

[0101] The iodofluoroalkane compound is obtained by adding an iodine monofluoride (IF) molecule to the carbon-carbon double bond of the olefin.

[0102] According to a preferred embodiment, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, Cl, I, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing at least one fluorine atom; Alternatively, the iodofluoroalkane compound may be of formula (II)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above; Alternatively, the iodofluoroalkane compound may be of formula (II)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y1, Y 2 and Y 3 The substituents R are selected independently of each other and for each n unit from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , R 4 , Y1, Y 2 or Y 3 The condition is that at least one of them is F.

[0103] According to a preferred embodiment, the olefin is CHF=CH2, CF2=CH2, CHF=CHF, CF2=CHF, CF2=CF2, CH3-CF=CH2, CH3-CH=CHF, CH2F-CH=CH2, CH3-CF=CHF, CH2F-CF=CH2, CH3-CH=CF2, CH2F-CH=CHF, CHF2-CH=CH2, CH3-CF=CF2, CH2F-CF=CHF, CHF2-CF=CH2, CH2F-CH=CF2, CHF2-CH=CHF, CF3-CH=CH2 , is a fluoroolefin selected from the group consisting of CH2F-CF=CF2, CHF2-CF=CHF, CF3-CF=CH2, CHF2-CH=CF2, CF3-CH=CHF, CHF2-CF=CF2, CF3-CF=CHF, CF3-CH=CF2, CF3-CF=CF2, and is also a fluoroolefin selected from the group consisting of CF2=CH2, CF2=CHF, CF2=CF2, CF3-CH=CH2, CF3-CF=CH2, CF3-CH=CHF, CF3-CF=CHF, and CF3-CF=CF2.

[0104] According to a preferred embodiment, the iodofluoroalkane compound is CHFI-CH2F, CHF2-CH2I, CF2I-CH2F, CF3-CH2I, CHFI-CHF2, CF2I-CHF2, CF3-CHFI, CF2I-CF3, CH3-CFI-CH2F, CH3-CF2-CH2I, CH3-CHI-CHF2, CH3-CHF-CHFI, CH2F-CHI-CH2F, CH2F-CHF-CH2I, CH3-CFI-CHF2, CH3-CF2-CH FI, CH2F-CFI-CH2F, CH2F-CF2-CH2I, CH3-CHI-CF3, CH3-CHF-CF2I, CH2F-CHI-CHF2, CH2F-CHF-CHFI, CHF2-CHF-CH2I, CH3-CFI- CF3, CH3-CF2-CF2I, CH2F-CFI-CHF2, CH2F-CF2-CHFI, CHF2-CF2-CH2I, CH2F-CHF-CF2I, CHF2-CHI-CHF2, CHF2-CHF-CHFI, CF3-C HI-CH2F, CF3-CHF-CH2I, CH2F-CF2-CF2I, CHF2-CFI-CHF2, CHF2-CF2-CHFI, CF3-CFI-CH2F, CF3-CF2-CH2I, CHF2-CHF-CF2I, CF3 -CHI-CHF2, CF3-CHF-CHFI, CHF2-CF2-CF2I, CF3-CFI-CHF2, CF3-CF2-CHFI, CF3-CHI-CF3, CF3-CHF-CF2I, CF3-CFI-CF3, CF3-CF Selected from the group consisting of 2-CF2I; Preferably, selected from the group consisting of CF2I-CH2F, CF3-CH2I, CF2I-CHF2, CF3-CHFI, CF2I-CF3, CF3-CHI-CH2F, CF3-CHF-CH2I, CF3-CFI-CH2F, CF3-CF2-CH2I, CF3-CHI-CHF2, CF3-CHF-CHFI, CF3-CFI-CHF2, CF3-CF2-CHFI, CF3-CFI-CF3, and CF3-CF2-CF2I.

[0105] According to a preferred embodiment, step a) includes: - Converting CF2=CH2 to CF3-CH2I; - Converting CF2=CHF to CF3-CHFI; or - Converting CF2=CF2 to CF3-CF2I; or - Converting CF3-CH=CH2 to CF3-CHI-CH2F; or - Converting CF3-CF=CH2 to CF3-CF2-CH2I; or - Converting CF3-CH=CHF to CF3-CHI-CHF2; or - Converting CF3-CF=CHF to CF3-CFI-CHF2; or - Convert CF3-CF=CF2 to CF3-CFI-CF3.

[0106] According to a preferred embodiment, anhydrous iodine monofluoride is prepared by mixing anhydrous iodine (I2) with anhydrous iodine pentafluoride (IF5).

[0107] According to a preferred embodiment, the method includes step b) purifying stream A to form stream B1 containing at least 90% by weight of the iodofluoroalkane compound.

[0108] Detailed description of Invention II The present invention relates to a method for producing an iodofluoroalkane compound, comprising step a) contacting an olefin with anhydrous iodine monofluoride (IF) to form a flow A containing the iodofluoroalkane compound and optionally unreacted iodine monofluoride.

[0109] Step a) of this method This method makes it possible to obtain iodofluoroalkane compounds with improved selectivity while maintaining a high conversion rate of the starting olefin.

[0110] The aforementioned olefin is formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) may be of the same nature, and in the formula, R 1 , R 2 , R 3 and R 4These are H, F, Cl, I, and C1-C, which are independent of each other. 10 Alkyl, C3-C 10 Cycloalkyl groups, C2-C 10 Alkenyl group, C3-C 10 Cycloalkenyl group, and C6-C 10 Selected from the group consisting of aryl groups.

[0111] The selectivity and conversion rate of this reaction can be increased by carrying out step a) using anhydrous iodine monofluoride. Here, the term "anhydrous" refers to iodine monofluoride containing less than 500 ppm of water, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, especially less than 10 ppm, preferably less than 5 ppm, and more preferably, the iodine monofluoride does not contain water.

[0112] According to a preferred embodiment, the olefin is a fluoroolefin. Preferably, the fluoroolefin is anhydrous. The term “anhydrous” as used herein refers to a fluoroolefin containing less than 500 ppm of water, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, particularly less than 10 ppm, and preferably less than 5 ppm, and the fluoroolefin is water-free, preferentially preferred. The use of anhydrous fluoroolefin in this method makes it possible to avoid the formation of impurities (such as reaction by-products and polymers derived from fluoroolefins).

[0113] According to a preferred embodiment, the fluoroolefin is of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) is of the same type, and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, Cl, I, and at least one fluorine atom. 10Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing at least one fluorine atom.

[0114] The term "alkyl" refers to a monovalent group derived from linear or branched alkanes containing a specific number of carbon atoms. The term "cycloalkyl" refers to a monovalent group derived from cycloalkanes containing a specific number of carbon atoms. The term "alkenyl" refers to a monovalent group containing a specific number of carbon atoms and at least one carbon-carbon double bond. The term "cycloalkenyl" refers to a monovalent group derived from cycloalkenes containing a specific number of carbon atoms and at least one carbon-carbon double bond in the cyclic portion. The term "aryl" refers to a monovalent group derived from arenes containing a specific number of carbon atoms.

[0115] Preferably, the alkyl, cycloalkyl, alkenyl, cycloalkenyl, or aryl group is not substituted with a functional group other than fluorine. Nevertheless, the group may contain several fluorine atoms on its carbon chain, for example, 1 to 10 fluorine atoms, preferably 1 to 5 fluorine atoms.

[0116] Preferably, the fluoroolefin is of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) is of the same type, and in the formula, R 1 , R 2 , R 3 and R4 These are C1-C atoms that may be independently substituted with H, F, I, and 1 to 10 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0117] Preferably, the fluoroolefin is of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) is of the same type, and in the formula, R 1 , R 2 , R 3 and R 4 The C1-C atoms may be independently substituted with H, F, I, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0118] According to a preferred embodiment, the fluoroolefin is of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) is of the same type, and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C5-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a perfluoro group as described above containing at least one fluorine atom.

[0119] Preferably, the fluoroolefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is of the same type, and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or 4 At least one of them is F or a perfluoro group as described above containing at least one fluorine atom.

[0120] According to another preferred embodiment, the fluoroolefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is of the same type, and in the formula, R 1 , R 2 , R 3 and R 4 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F, where n is an integer from 1 to 10. 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0121] The aforementioned fluoroolefin is formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) may be of the same nature, and in the formula, R 1 , R 2 , R 3 and R 4 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F (where n is an integer from 1 to 5), however, the substituent R 1 , R 2 , R 3 , R 4 , Y1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0122] The aforementioned fluoroolefin is formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) may be of the same nature, and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 10, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0123] The aforementioned fluoroolefin is formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) may be of the same nature, and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0124] In particular, the fluoroolefin is selected from the group consisting of CHF=CH2, CF2=CH2, CHF=CHF, CF2=CHF, CF2=CF2, CH3-CF=CH2, CH3-CH=CHF, CH2F-CH=CH2, CH3-CF=CHF, CH2F-CF=CH2, CH3-CH=CF2, CH2F-CH=CHF, CHF2-CH=CH2, CH3-CF=CF2, CH2F-CF=CHF, CHF2-CF=CH2, CH2F-CH=CF2, CHF2-CH=CHF, CF3-CH=CH2, CH2F-CF=CF2, CHF2-CF=CHF, CF3-CF=CH2, CHF2-CH=CF2, CF3-CH=CHF, CHF2-CF=CF2, CF3-CF=CHF, CF3-CH=CF2, CF3-CF=CF2.

[0125] More specifically, the fluoroolefin is selected from the group consisting of CF2=CH2, CF2=CHF, CF2=CF2, CF3-CH=CH2, CF3-CF=CH2, CF3-CH=CHF, CF3-CF=CHF, and CF3-CF=CF2.

[0126] Preferably, iodine monofluoride is brought into contact with the olefin, preferably a fluoroolefin, in a stoichiometric or greater amount. For example, the molar ratio of IF / fluoroolefin is 1 to 50, preferably 1.5 to 25, and particularly 2 to 20.

[0127] Preferably, anhydrous iodine monofluoride is prepared from an anhydrous reagent. Preferably, anhydrous iodine monofluoride is prepared in situ by mixing anhydrous iodine (I2) with anhydrous iodine pentafluoride (IF5). In this case, flow A may contain unreacted iodine and / or iodine pentafluoride in addition to the iodofluoroalkane compound and optionally unreacted iodine monofluoride. For both iodine and iodine pentafluoride, the term "anhydrous" as used herein means that the amount of water in the compound under consideration is less than 500 ppm, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, especially less than 10 ppm, and preferably less than 5 ppm. Preferably, iodine and iodine pentafluoride do not contain water.

[0128] The mixing of anhydrous iodine and anhydrous iodine pentafluoride can be carried out in liquid form. Therefore, the iodine dissolves in the iodine pentafluoride. Alternatively, iodine may be introduced into the iodine pentafluoride solution in gaseous form.

[0129] Alternatively, anhydrous monofluoride can be produced by mixing anhydrous iodine with anhydrous iodine heptafluoride, or anhydrous iodine with anhydrous iodine difluoride, or anhydrous iodine with anhydrous iodine trifluoride.

[0130] The iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, Cl, I, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing at least one fluorine atom.

[0131] Preferably, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, I, and 1 to 10 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0132] Preferably, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1, R 2 , R 3 and R 4 The C1-C atoms may be independently substituted with H, F, I, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0133] According to a preferred embodiment, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C5-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a perfluoro group as described above containing at least one fluorine atom.

[0134] Preferably, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or 4 At least one of them is F or a perfluoro group as described above containing at least one fluorine atom.

[0135] According to another preferred embodiment, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F, where n is an integer from 1 to 10. 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3The condition is that at least one of them is F.

[0136] The iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 ) may be a compound of the same type, where R 1 , R 2 , R 3 and R 4 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F (where n is an integer from 1 to 5), however, the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0137] The iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 ) may be a compound of the same type, where R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 10, but the substituent R 1 , R2 、R 3 、R 4 、Y 1 、Y 2 or Y 3 on condition that at least one of them is F.

[0138] The iodo fluoroalkane compound may be a compound of formula (II) (R 1 )(R 2 )CF-C(I)(R 3 )(R 4 ]>), wherein R 1 、R 2 、R 3 and R 4 are, independently of each other, H, F or Y 1 -[-C(Y 2 )(Y 3 )-] n -(wherein Y 1 、Y 2 and Y 3 are, independently of each other and independently for each unit n, selected from the group consisting of H and F, and n is an integer from 1 to 5), provided that at least one of the substituents R 1 、R 2 、R 3 、R 4 、Y 1 、Y 2 or Y 3 is F.

[0139] According to a preferred embodiment, the iodofluoroalkane compound is CHFI-CH2F, CHF2-CH2I, CF2I-CH2F, CF3-CH2I, CHFI-CHF2, CF2I-CHF2, CF3-CHFI, CF2I-CF3, CH3-CFI-CH2F, CH3-CF2-CH2I, CH3-CHI-CHF2, CH3-CHF-CHFI, CH2F-CHI-CH2F, CH2F-CHF-CH2I, CH3-CFI-CHF2, CH3-CF2-CHFI, CH2F-CFI-CH2F, CH2F-CF2-CH2I, CH3-CHI-CF3, CH3-CHF-CF2I, CH2F-CHI-CHF2, CH2F-CHF-CHFI, CHF2-CHF-CH2I, CH3-CFI-CF3, CH3-CF 2-CF2I, CH2F-CFI-CHF2, CH2F-CF2-CHFI, CHF2-CF2-CH2I, CH2F-CHF-CF2I, CHF2-CHI-CHF2, CHF2 -CHF-CHFI, CF3-CHI-CH2F, CF3-CHF-CH2I, CH2F-CF2-CF2I, CHF2-CFI-CHF2, CHF2-CF2-CHFI, CF3- CFI-CH2F, CF3-CF2-CH2I, CHF2-CHF-CF2I, CF3-CHI-CHF2, CF3-CHF-CHFI, CHF2-CF2-CF2I, CF3-CF I-CHF2, CF3-CF2-CHFI, CF3-CHI-CF3, CF3-CHF-CF2I, CF3-CFI-CF3, CF3-CF2-CF2I.

[0140] Preferably, the iodofluoroalkane compound is selected from the group consisting of CF2I-CH2F, CF3-CH2I, CF2I-CHF2, CF3-CHFI, CF2I-CF3, CF3-CHI-CH2F, CF3-CHF-CH2I, CF3-CFI-CH2F, CF3-CF2-CH2I, CF3-CHI-CHF2, CF3-CHF-CHFI, CF3-CFI-CHF2, CF3-CF2-CHFI, CF3-CFI-CF3, and CF3-CF2-CF2I.

[0141] According to a preferred embodiment, step a) includes: - Converting CF2=CH2 to CF3-CH2I; - Converting CF2=CHF to CF3-CHFI; or - Converting CF2=CF2 to CF3-CF2I; or - Converting CF3-CH=CH2 to CF3-CHI-CH2F; or - Converting CF3-CF=CH2 to CF3-CF2-CH2I; or - Converting CF3-CH=CHF to CF3-CHI-CHF2; or - Converting CF3-CF=CHF to CF3-CFI-CHF2; or - Convert CF3-CF=CF2 to CF3-CFI-CF3.

[0142] Step a) can be carried out in either the liquid or gas phase. Step a) can be carried out in either the presence or absence of the catalyst.

[0143] gas phase process a) When step a) is carried out in the gas phase, it may be carried out in the presence of a catalyst. Preferably, the catalyst is selected from the group consisting of oxides, oxyhalides, or halides of metals or metalloids from groups 4 to 15 of the periodic table, or oxides, oxyhalides, or halides of metals selected from Li, Na, K, Cs, Mg, and Ca.

[0144] Preferably, the catalyst is chromium oxide, chromium oxyfluoride, or chromium fluoride. Chromium oxyfluoride preferably has a fluorine content of 10% to 50% by weight, preferably 20% to 50% by weight, and particularly 30% to 50% by weight. The fluorine content is measured by ion measurement, by the weight change of the catalyst, or by any other quantitative method known to those skilled in the art. The chromium oxyfluoride or chromium fluoride catalyst is preferably 15m 2 / g to 100m 2 It has a specific surface area of ​​ / g. The chromium oxide catalyst is preferably 100m 2 / g to 300m 2It has a specific surface area of ​​ / g. The specific surface area is measured using a Micromeritics Gemini 2360 instrument with a standard 5-point method (BET method). Furthermore, the catalyst content is 0.01% to 10% by weight relative to the fluoroolefin. If the catalyst is chromium oxide, chromium oxyfluoride, or chromium fluoride, it may contain 0.5% to 10% by weight of a co-catalyst relative to the total weight of the catalyst. The co-catalyst is selected from Cr, Ni, Zn, Ti, V, Zr, Mo, Ge, Sn, Pb, and Mg.

[0145] When the metal is selected from Li, Na, K, Cs, Mg, and Ca, the anion that associates with that metal is F - Cl - , I - or CO3 2- Preferably, the catalyst is NaI or KI. Preferably, the catalyst is 20m 2 / g to 1000m 2 Specific surface area between / g, especially 20m² 2 / g to 300m 2 It has a specific surface area between / g.

[0146] The catalyst may be deposited on a porous support. The porous support may be selected from activated carbon, graphite, alumina, and alumina fluoride.

[0147] When the metal of the catalyst is selected from Li, Na, K, Cs, Mg, and Ca, the catalyst content is 1% to 30% by weight relative to the fluoroolefin.

[0148] If the catalyst is selected from the group consisting of oxides, oxyhalides, or halides of metals or metalloids from groups 4 to 15 of the periodic table, the catalyst may be activated before use in step a). For example, the catalyst may be activated in the presence of oxygen, air, hydrogen iodide or HF, or a mixture thereof.

[0149] The catalyst may become inactive over time. Therefore, step a) may be carried out in the presence of oxygen or air, or in the presence of an oxygen-nitrogen mixture. When oxygen is used in step a), the oxygen is present in an amount of 0.005 mol% to 10 mol% relative to the molar amount of fluoroolefin.

[0150] The catalyst may also be regenerated after the method has been carried out. The regeneration step may include bringing the catalyst into contact with a flow of oxygen or air at a temperature of 200°C to 700°C.

[0151] Alternatively, step a) may be carried out in the gas phase, in the absence of the catalyst.

[0152] In the gas phase, step a) is carried out at a temperature of 150°C to 700°C, preferably 250°C to 600°C, with or without the catalyst.

[0153] Regardless of whether step a) is carried out in the gas phase, in the presence or absence of the catalyst, the pressure in this step is 0.1 bar to 30 bar, preferably 1 bar to 20 bar, and particularly 1 bar to 15 bar.

[0154] Liquid phase process a) Alternatively, step a) may be carried out in the liquid phase. The temperature at which step a) is carried out in the liquid phase is 50°C to 280°C, preferably 50°C to 250°C.

[0155] Step a) may be carried out in the presence of solvent S1. Preferably, solvent S1 is anhydrous. The term “anhydrous” here means solvent S1 containing less than 500 ppm of water, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, particularly less than 10 ppm, preferably less than 5 ppm, and preferentially preferably solvent S1 does not contain water. Solvent S1 has a boiling point from 0°C to 250°C, preferably from 20°C to 250°C, particularly from 20°C to 200°C. The solvent S1 is selected from the group consisting of acetic acid, CCl4, chloroform, dichloromethane, sulfolane, tetramethylene sulfone, N,N-dimethylformamide, dimethyl sulfoxide, N,N-dimethylacetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone, and mixtures thereof.

[0156] According to one embodiment, step a) is carried out in the presence of a catalyst selected from alkali metals or alkaline earth metal salts. Preferably, the catalyst is an alkali metal salt. Any alkali metal iodide may be used, but preferably sodium iodide or potassium iodide is used. The ratio of the catalyst to the olefin (preferably the fluoroolefin described above) is between 1 and 20, preferably between 1 and 10. The catalyst is preferably 20 ml 2 / g to 1000m 2 Specific surface area between / g, especially 20m² 2 / g to 300m 2 It has a specific surface area between / g. The catalyst may be deposited on a porous support. The porous support may be selected from activated carbon, graphite, alumina, and alumina fluoride.

[0157] According to another embodiment, step a) is carried out in the presence of a catalyst containing a Lewis acid catalyst, a metal halide, particularly an antimony, tin, tantalum, or titanium halide, or a transition metal halide such as molybdenum, niobium, or iron. For example, the catalyst may be SbF5, SbF3, TiF4, SnF4, TaF5, NbF5, TiF4, FeF3, or MoF6. Preferably, the catalyst is liquid at the temperature in which step a) is carried out. Therefore, the presence of solvent S1 is optional when these catalysts are used to carry out step a).

[0158] According to another embodiment, the method may be carried out in the presence of a mixture of fluoroolefins as described above to result in the formation of a mixture of iodofluoroalkane compounds in flow A and flow B1.

[0159] As described above, step a) makes it possible to obtain flow A, which contains the iodofluoroalkane compound and optionally unreacted iodine monofluoride. If iodine monofluoride is prepared by mixing anhydrous iodine (I2) and anhydrous iodine pentafluoride (IF5), flow A may also contain unreacted iodine and / or iodine pentafluoride. Flow A may also contain other compounds such as impurities, reaction by-products (e.g., products resulting from the addition of one or more iodine or fluorine atoms to one or more carbon atoms of an olefin) or unreacted olefins.

[0160] Step b) of this method The stream A is purified to form a stream B1 containing at least 90% by weight of the iodofluoroalkane compound. Preferably, after purification, the content of the iodofluoroalkane compound in the stream B1 is greater than 92%, advantageously greater than 94%, preferably 96%, more preferably 98%, particularly greater than 99%, and more precisely greater than 99.5%. The stream A is preferably purified by distillation, azeotropic distillation, pressurized distillation, extractive distillation, cold separation, absorption into a solvent, or a combination thereof. The stream A may also be purified by contact with an adsorbent. The adsorbent can be a molecular sieve or zeolite having pore openings with an average diameter between 3 angstroms and 11 angstroms, advantageously between 4 angstroms and 10 angstroms, preferably between 5 angstroms and 10 angstroms. The purification of the stream A may include one or more of the above purification techniques, i.e., a series of distillations, or a combination of, for example, cold separation and distillation.

[0161] Furthermore, the purification of flow A results in the formation of, for example, flow B2 containing iodine monofluoride, or (if flow A contains) flow B2 containing iodine and iodine pentafluoride, or (if flow A contains) flow B2 containing unreacted olefins. To remove impurities or reaction by-products that may be generated during step a) and present in flow A before purification, flow B2 may be purified before carrying out step c), depending on its components. Preferably, flow B2 contains unreacted iodine and iodine pentafluoride, and optionally unreacted iodine monofluoride and olefins.

[0162] Step c) of this method Step c) of this method includes recirculating flow B2 back to step a). This recirculation step improves the overall yield of the method (better conversion rate), saves expensive reagents (and catalysts), and minimizes the environmental impact. Without this recirculation step, unreacted iodine monofluoride (or its precursors I2 and IF5) and / or olefins would have to be incinerated, thus increasing the carbon dioxide emissions of the method.

[0163] If flow B1 contains unreacted olefins, the reagent can be removed from flow B1 and recycled back to step a).

[0164] This method may be performed continuously, or in batch or semi-batch form.

[0165] Preferably, in order to avoid corrosion problems, the reactor in which step a) is carried out is made of a material that includes a base layer made of material M1 and an inner layer made of material M2.

[0166] Advantageously, material M2 contains at least 40% by weight of nickel relative to the total weight of material M2. Preferably, material M2 contains at least 45% by weight of nickel, more preferably at least 50% by weight of nickel, particularly at least 55% by weight of nickel, especially at least 60% by weight of nickel, preferably at least 65% by weight of nickel, and more preferably at least 70% by weight of nickel relative to the total weight of material M2.

[0167] Material M2 may also contain chromium in an amount of less than 35% by weight, preferably less than 30% by weight, more preferably less than 20% by weight, more preferably less than 15% by weight, particularly less than 10% by weight, and more precisely less than 5% by weight relative to the total weight of Material M2.

[0168] Material M2 may also contain molybdenum in an amount of less than 35% by weight, preferably less than 30% by weight, more preferably less than 20% by weight, more preferably less than 15% by weight, particularly less than 10% by weight, and more precisely less than 5% by weight relative to the total weight of material M2.

[0169] Preferably, material M2 is Monel®, Hastelloy®, Inconel®, or Incoloy®.

[0170] According to a preferred embodiment, material M1 comprises at least 70% by weight of iron, advantageously at least 75% by weight, preferably at least 80% by weight, more preferably at least 85% by weight, particularly at least 90% by weight, and more precisely at least 95% by weight of iron relative to the total weight of material M1.

[0171] Material M1 may also contain less than 2% by weight, advantageously less than 1.5% by weight, preferably less than 1% by weight, more preferably less than 0.75% by weight, particularly less than 0.5% by weight, more precisely less than 0.2% by weight, and preferably less than 0.1% by weight of carbon relative to the total weight of Material M1. More specifically, Material M1 may contain between 0.01% and 0.2% by weight of carbon relative to the total weight of Material M1.

[0172] Preferably, the base layer and the inner layer are arranged to face each other by molten or low-temperature plating, hot or cold rolling, or pressure welding.

[0173] Examples Example 1 Synthesis of CF3-CFI-CF3 The apparatus used was a 0.8 L autoclave made of Hastelloy C276, equipped with a condenser and pressure regulating valve. The autoclave was degassed and inert with nitrogen, and the following components were sequentially introduced: 150 g (0.59 mol) of anhydrous iodine, 65 g (0.29 mol) of anhydrous iodine pentafluoride, and 6.5 g (0.03 mol) of antimony pentafluoride (SbF5). The autoclave was then stirred for 45 minutes, immersed in an oil bath, and the temperature was raised to 80°C while maintaining the condenser temperature at approximately 17°C. When the reaction medium temperature reached 80°C, 12.5 g / h (0.083 mol / h) of hexafluoropropene (C3F6) was continuously injected.

[0174] During the reaction, volatile products were continuously removed, washed, and recovered. Six hours after the reaction, the autoclave was cooled to room temperature. The reaction products were then degassed, washed, dried, and analyzed by gas chromatography (area percentage method).

[0175] The yield of CF3-CFI-CF3, expressed as the ratio of the number of moles of detected CF3-CFI-CF3 to the number of moles of hexafluoropropene initially introduced, was 93.6%.

[0176] Example 2 Synthesis of CF3-CF2-CH2I The following were introduced sequentially into a reaction assembly similar to that in Example 1: 200 g (0.79 mol) of anhydrous iodine, 85 g (0.38 mol) of anhydrous iodine pentafluoride, and 22.0 g (0.1 mol) of antimony pentafluoride (SbF5). The autoclave was then stirred for 60 minutes, immersed in an oil bath, and the temperature was raised to 80°C while maintaining the condenser temperature at approximately 17°C. Once the reaction medium reached 80°C, 11.4 g / h (0.1 mol / h) of 2,3,3,3-tetrafluoropropene (HFO-1234yf) was continuously injected.

[0177] During the reaction, volatile products were continuously removed, washed, and recovered. After 10 hours of reaction, the autoclave was cooled to room temperature. The reaction products were then degassed, washed, dried, and analyzed by gas chromatography (area percentage method).

[0178] The yield of CF3-CF2-CH2I, expressed as the ratio of the number of moles of detected CF3-CF2-CH2I to the number of moles of initially introduced CF3-CF=CH2, was 80.5%.

[0179] Invention III Summary of Invention III The present invention relates to a method for producing an iodofluoroalkane compound, comprising step a) contacting a hydrofluoroalkane with iodine anhydride to form a flow A containing the iodofluoroalkane compound, hydrogen iodide (HI), and unreacted iodine. Step a) allows for the substitution of hydrogen atoms in the hydrofluoroalkane with iodine atoms to form the iodofluoroalkane. Preferably, the hydrofluoroalkane consists of carbon, hydrogen, and fluorine atoms.

[0180] According to a preferred embodiment, the method includes step b), in which flow A is separated to form flow B1 containing the iodofluoroalkane compound and flow B2 containing unreacted iodine. Hydrogen iodide is contained in flow B1, flow B2, or both.

[0181] According to a preferred embodiment, the method includes step c), in which flow B2 is recirculated to step a).

[0182] According to a preferred embodiment, the hydrofluoroalkane is of formula (I)(R 1 )(R 2 )CF(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, and at least one fluorine atom. 10 C3-C which may be substituted with alkyl groups and at least one fluorine atom. 10 Selected from the group consisting of cycloalkyl groups, provided that the substituent R 1 , R 2 or R 3at least one of which is H or a group as described above containing at least one hydrogen atom, provided that this is the case.

[0183] According to a preferred embodiment, the iodo-fluoroalkane has the formula (II) (R 1 )(R 2 )CF(R 3 ), where R 1 , R 2 and R 3 are, independently of one another, H, F, I, a C1-C 10 alkyl group optionally substituted with at least one fluorine atom and / or at least one iodine atom, and a C3-C 10 cycloalkyl group optionally substituted with at least one fluorine atom and / or at least one iodine atom, provided that at least one of the substituents R 1 , R 2 or R 3 is I or a group as described above containing at least one iodine atom, provided that this is the case.

[0184] According to a preferred embodiment, the hydrofluoroalkane has the formula (I) (R 1 )(R 2 )CH(R 3 ), where R 1 , R 2 and R 3 are, independently of one another, selected from the group consisting of H, F, a C1-C5 perfluoroalkyl group and a C5-C 10 perfluorocycloalkyl group.

[0185] According to a preferred embodiment, the iodo-fluoroalkane compound has the formula (II) (R 1 )(R 2 )CFI, where R 1 and R 2 are, independently of one another, selected from the group consisting of H, F, a C1-C5 perfluoroalkyl group and a C5-C 10 perfluorocycloalkyl group.

[0186] According to a preferred embodiment, the hydrofluoroalkane is of formula (I)(R 1 )(R 2 )CF(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 10, but the substituent R 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is H.

[0187] According to a preferred embodiment, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF(R 3 It is a compound of ) and in the formula, R 1 , R 2 and R 3 These are H, F, I, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 H and I are independent of each other and independent of each unit n. A group consisting of and F is selected, where n is an integer from 1 to 10, but the substituent R is selected. 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is I.

[0188] According to a preferred embodiment, the hydrofluoroalkane compound is CH3F, CH2F2, CHF3, CH2F-CH3, CHF2-CH3, CH2F-CH2F, CF3-CH3, CHF2-CH2F, CF3-CH2F, CHF2-CHF2, CF3-CHF2, CH2F-CH2-CH3, CH3-CHF-CH3, CH2F-CH2-CH2F, CHF2-CH2-C H3, CH2F-CHF-CH3, CH3-CF2-CH3, CHF2-CH2-CH2F, CF3-CH2-CH3, CH2F-CHF-CH2F, CHF2-CHF-CH3, CH2 F-CF2-CH3, CHF2-CH2-CHF2, CF3-CH2-CH2F, CHF2-CHF-CH2F, CF3-CHF-CH3, CH2F-CF2-CH2F, CHF2-CF Selected from the group consisting of 2-CH3, CF3-CH2-CHF2, CHF2-CHF-CHF2, CF3-CHF-CH2F, CHF2-CF2-CH2F, CF3-CF2-CH3, CF3-CH2-CF3, CF3-CHF-CHF2, CHF2-CF2-CHF2, CF3-CF2-CH2F, CF3-CHF-CF3, and CF3-CF2-CHF2, and TivoliCH2 The group is selected from F2, CHF3, CHF2-CH3, CF3-CH3, CF3-CH2F, CF3-CHF2, CH2F-CHF-CH3, CF3-CH2-CH3, CF3-CH2-CH2F, CF3-CHF-CH3, CF3-CH2-CHF2, CF3-CHF-CH2F, CF3-CH2-CF3, CF3-CHF-CHF2, and CF3-CHF-CF3.

[0189] According to a preferred embodiment, the iodo-fluoroalkane compound is CH2FI, CHFI2, CHF2I, CF2I2, CF3I, CHFI-CH3, CH2F-CH2I, CFI2-CH3, CH2F-CHI2, CHFI-CH2I, CF2I-CH3, CHF2-CH2I, CHF2-CHI2, CF2I-CH2I, CHFI-CH2F, CFI2-CH2F, CHFI-CHFI, CF3-CH2I, CF3-CHI2, CF2I-CH2F, CHF2-CHFI, CHF2-CFI2, CF2I-CHFI, CF3-CHFI, CF3-CFI2, CF2I-CHF2, CF2I-CF2I, CF3-CF2I, CHFI-CH2-CH3, CH2F-CHI-CH3, CH2F-CH2-CH2I, CFI2-CH2-CH3, CH2F-CI2-CH3, CH2F-CH2-CHI2, CHFI-CHI-CH3, CHFI-CH2-CH2I, CH2F-CHI-CH2I, CH2I-CHF-CH3, CH3-CFI-CH3, CHI2-CHF-CH3, CH2I-CFI-CH3, CH2I-CHF-CH2I, CHFI-CH2-CH2F, CH2F-CHI-CH2F, CFI2-CH2-CH2F, CH2F-CI2-CH2F, CHFI-CHI-CH2F, CHFI-CH2-CHFI, CF2I-CH2-CH3, CHF2-CHI-CH3, CHF2-CH2-CH2I, CHF2-CI2-CH3, CHF2-CH2-CHI2, CF2I-CHI-CH3, CF2I-CH2-CH2I, CHF2-CHI-CH2I, CHFI-CHF-CH3, CH2F-CFI-CH3, CH2F-CHF-CH2I, CFI2-CHF-CH3, CH2F-CHF-CHI2, CHFI-CFI-CH3, CHFI-CHF-CH2I, CH2F-CFI-CH2I, CH2I-CF2-CH3, CHI2-CF2-CH3, CH2I-CF2-CH2I, CF2I-CH2-CH2F, CHF2-CHI-CH2F, CHF2-CH2-CHFI, CHF2-CI2-CH2F, CHF2-CH2-CFI2, CF2I-CHI-CH2F, CF2I-CH2-CHFI, CHF2-CHI-CHFI, CF3-CHI-CH3, CF3-CH2-CH2I, CF3-CI2-CH3, CF3-CH2-CHI2, CF3-CHI-CH2I, CHFI-CHF-CH2F,Selected from the group consisting of CH2F-CFI-CH2F, CFI2-CHF-CH2F, CHFI-CFI-CH2F, CHFI-CHF-CHFI, CF2I-CHF-CH3, CHF2-CFI-CH3, CHF2-CHF-CH2I, CHF2-CHF-CHI2, CF2I-CFI-CH3, CF2I-CHF-CH2I, CHF2-CFI-CH2I, CHFI-CF2-CH3, CH2F-CF2-CH2I, CFI2-CF2-CH3, CH2F-CF2-CHI2, CHFI-CF2-CH2I, CF2I-CH2-CHF2, CHF2-CHI-CHF2, CHF2-CI2-CHF2, CF2I-CHI-CHF2, CF2I-CH2-CF2I, CF3-CHI-CH2F, CF3-CH2-CHFI, CF3-CI2-CH2F, CF3-CH2-CFI2, CF3-CHI-CHFI, CF2I-CHF-CH2F, CHF2-CFI-CH2F, CHF2-CHF-CHFI, CHF2-CHF-CFI2, CF2I-CFI-CH2F, CF2I-CHF-CHFI, CHF2-CFI-CHFI, CF3-CFI-CH3, CF3-CHF-CH2I, CF3-CHF-CHI2, CF3-CFI-CH2I, CHFI-CF2-CH2F, CFI2-CF2-CH2F, CHFI-CF2-CHFI, CF2I-CF2-CH3, CHF2-CF2-CH2I, CHF2-CF2-CHI2, CF2I-CF2-CH2I, CF3-CHI-CHF2, CF3-CH2-CF2I, CF3-CI2-CHF2, CF3-CHI-CF2I, CF2I-CHF-CHF2, CHF2-CFI-CHF2, CF2I-CFI-CHF2, CF2I-CHF-CF2I, CF3-CFI-CH2F, CF3-CHF-CHFI, CF3-CHF-CFI2, CF3-CFI-CHFI, CF2I-CF2-CH2F, CHF2-CF2-CHFI, CHF2-CF2-CFI2, CF2I-CF2-CHFI, CF3-CF2-CH2I, CF3-CF2-CHI2, CF3-CHI-CF3, CF3-CI2-CF3, CF3-CFI-CHF2, CF3-CHF-CF2I, CF3-CFI-CF2I, CF2I-CF2-CHF2, CF2I-CF2-CF2I, CF3-CF2-CHFI, CF3-CF2-CFI2, CF3-CFI-CF3, CF3-CF2-CF2I; preferably,The iodofluoroalkane compounds mentioned above are CHF2I, CF2I2, CF3I, CF2I-CH3, CHF2-CH2I, CHF2-H2I, CF2I-CH2I, CF3-CH2I, CF3-H2I, CF3-CHFI, CF3-CFI2, CF3-CF2I, CHFI-CHF-CH3, CH2F-CFI-CH3, CH2F-CHF-CH2I, CFI2-CHF-CH3, and CH2F-CHF-C HI2, CHFI-CFI-CH3, CHFI-CHF-CH2I, CH2F-CFI-CH2I, CF3-CHI-CH3, CF3-CH2-CH2I, CF3-CI2-CH3, CF3-CH2-C HI2, CF3-CHI-CH2I, CF3-CHI-CH2F, CF3-CH2-CHFI, CF3-CI2-CH2F, CF3-CH2-CFI2, CF3-CHI-CHFI, CF3-CFI-C H3, CF3-CHF-CH2I, CF3-CHF-CHI2, CF3-CFI-CH2I, CF3-CHI-CHF2, CF3-CH2-CF2I, CF3-CI2-CHF2, CF3-CHI-CF 2I, CF3-CFI-CH2F, CF3-CHF-CHFI, CF3-CHF-CFI2, CF3-CFI-CHFI, CF3-CHI-CF3, CF3-CI2-CF3, CF3-CFI-CHF2 The iodofluoroalkane compound is selected from the group consisting of CF3-CHF-CF2I, CF3-CFI-CF2I, and CF3-CFI-CF3; preferably, the iodofluoroalkane compound is selected from the group consisting of CH2FI, CHF2I, CF3I, CHFI-CH3, CF2I-CH3, CHFI-CH2F, CF3-CH2I, CF2I-CH2F, CF3-CHFI, CF2I-CHF2, CF3-CF2I, CHFI-CH2-CH3, CH3, -CFI-CH3, CHFI-CH2-CH2F, CF2I-CH2-CH3, CHFI-CHF-CH3, CH2I-CF2-CH3, CF2I-CH2-CH2F, CF3-CH2-CH2I, CHFI-CHF-CH2F, CF2I-CHF-CH3, CHFI-CF2-CH3, CF2I-CH2-C HF2, CF3-CH2-CHFI, CF2I-CHF-CH2F, CF3-CFI-CH3, CHFI-CF2-CH2F, CF2I-CF2-CH3, CF3-CH2-CF2I, CF2I-CHF-CHF2, CF3-CHF-CHFI, CF2I-CF2-CH2F, CF3-CF2-CH2I, CF3 -The iodofluoroalkane compound is selected from the group consisting of CHI-CF3, CF3-CHF-CF2I, CF2I-CF2-CHF2, CF3-CF2-CHFI, CF3-CFI-CF3, and CF3-CF2-CF2I; in particular, the iodofluoroalkane compound is selected from the group consisting of CHF2I, CF3I, CF2I-CH3, CF3-CH2I, CF3-CHFI, CF3-CF2I, CHFI-CHF-CH3, CF3-CH2-CH2I, CF3-CH2-CHFI, CF3-CFI-CH3, CF3-CH2-CF2I, CF3-CHF-CHFI, CF3-CHI-CF3, CF3-CHF-CF2I, and CF3-CFI-CF3.

[0190] According to a preferred embodiment, step a) involves one of the following reactions: - Converting CH2F2 to CHF2I, CF2I2, or a mixture of both, preferably CHF2I; - Converting CF3 to CF3I; - Converting CHF2-CH3 to CF2I-CH3, CHF2-CH2I, CHF2-CHI2, CF2I-CH2I, or a mixture thereof, preferably CF2I-CH3; - Converting CF3-CH3 to CF3-CH2I, CF3-CHI2, or a mixture of both, preferably CF3-CH2I; - Converting CF3-CH2F to CF3-CHFI, CF3-CFI2, or a mixture of both, preferably CF3-CHFI; - Converting CF3-CHF2 to CF3-CF2I; - Converting CH2F-CHF-CH3 to CHFI-CHF-CH3, CH2F-CFI-CH3, CH2F-CHF-CH2I, CFI2-CHF-CH3, CH2F-CHF-CHI2, CHFI-CFI-CH3, CHFI-CHF-CH2I, CH2F-CFI-CH2I, or a mixture thereof, preferably CHFI-CHF-CH3; - Converting CF3-CH2-CH3 to CF3-CHI-CH3, CF3-CH2-CH2I, CF3-CI2-CH3, CF3-CH2-CHI2, CF3-CHI-CH2I, or a mixture thereof, preferably CF3-CH2-CH2I; - Converting CF3-CH2-CH2F to CF3-CHI-CH2F, CF3-CH2-CHFI, CF3-CI2-CH2F, CF3-CH2-CFI2, CF3-CHI-CHFI, or a mixture thereof, preferably CF3-CH2-CHFI; - Converting CF3-CHF-CH3 to CF3-CFI-CH3, CF3-CHF-CH2I, CF3-CHF-CHI2, CF3-CFI-CH2I, or a mixture thereof, preferably CF3-CFI-CH3; - Converting CF3-CH2-CHF2 to CF3-CHI-CHF2, CF3-CH2-CF2I, CF3-CI2-CHF2, CF3-CHI-CF2I, or a mixture thereof, preferably CF3-CH2-CF2I; - Converting CF3-CHF-CH2F to CF3-CFI-CH2F, CF3-CHF-CHFI, CF3-CHF-CFI2, CF3-CFI-CHFI, or a mixture thereof, preferably CF3-CHF-CHFI; - Converting CF3-CH2-CF3 to CF3-CHI-CF3 or CF3-CI2-CF3 or a mixture of both, preferably CF3-CHI-CF3; - Converting CF3-CHF-CHF2 to CF3-CFI-CHF2, CF3-CHF-CF2I, CF3-CFI-CF2I, or a mixture thereof, preferably CF3-CHF-CF2I; or - Converting CF3-CHF-CF3 to CF3-CFI-CF3.

[0191] According to a preferred embodiment, step a) is carried out in the presence of a catalyst selected from antimony halides, iron halides, titanium halides, or tin halides; oxides, oxyhalides, or halides of chromium or aluminum; and alkali metal or alkaline earth metal salts or mixtures thereof.

[0192] According to a preferred embodiment, step a) is carried out in the gas phase at a temperature of 250°C to 700°C.

[0193] According to a preferred embodiment, step a) is carried out in a liquid phase, in the presence of a polar aprotic solvent, preferably at a temperature of 50°C to 300°C.

[0194] Detailed description of Invention III The present invention relates to a method for producing iodofluoroalkane compounds. In particular, the method involves contacting a hydrofluoroalkane with iodine anhydride. Step a) forms a flow A containing the iodofluoroalkane compound, hydrogen iodide, and unreacted iodine.

[0195] Preferably, the method also includes a step of separating the compounds contained in flow A. The method may also include a step of recirculating the starting reagent.

[0196] Therefore, preferably, the method includes the following steps: a) A step of contacting a hydrofluoroalkane with iodine anhydride to form a flow A containing the iodofluoroalkane compound, hydrogen iodide (HI), and unreacted iodine; b) A step of separating flow A to form flow B1 containing the iodofluoroalkane compound and flow B2 containing unreacted iodine, wherein hydrogen iodide is contained in flow B1, flow B2, or both; C) A step of recirculating the flow B2 to step a).

[0197] Step a) of this method Step a) of this method requires contacting the hydrofluoroalkane with anhydrous iodine. Here, the term "anhydrous" refers to iodine containing less than 500 ppm of water, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, more precisely less than 10 ppm, preferably less than 5 ppm, and preferentially, the iodine does not contain water. The use of anhydrous iodine in this method prevents the formation of impurities.

[0198] Preferably, the hydrofluoroalkane is of formula (I)(R 1 )(R 2 )CF(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, and at least one fluorine atom. 10 C3-C which may be substituted with alkyl groups and at least one fluorine atom. 10 Selected from the group consisting of cycloalkyl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is H or a group as described above containing at least one hydrogen atom.

[0199] The term "alkyl" refers to a monovalent group derived from linear or branched alkanes containing a specific number of carbon atoms. The term "cycloalkyl" refers to a monovalent group derived from cycloalkanes containing a specific number of carbon atoms.

[0200] Preferably, the alkyl or cycloalkyl group is not substituted with a functional group other than fluorine. Nevertheless, the group may contain several fluorine atoms on its carbon chain, for example, 1 to 5 fluorine atoms, preferably 1 to 3 fluorine atoms.

[0201] More preferably, the hydrofluoroalkane is of formula (I)(R 1 )(R 2 )CF(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, and 1 to 10 fluorine atoms. 10 C3-C which may be substituted with alkyl groups and 1 to 10 fluorine atoms. 10 Selected from the group consisting of cycloalkyl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is H or a group as described above containing at least one hydrogen atom.

[0202] In particular, hydrofluoroalkanes are given by formula (I)(R 1 )(R 2 )CF(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 The substituents R are independently selected from the group consisting of C1-C5 alkyl groups which may be substituted with H, F, and 1 to 5 fluorine atoms, and C3-C5 cycloalkyl groups which may be substituted with 1 to 5 fluorine atoms, provided that the substituent R 1 , R 2 or R 3 At least one of them is H or a group as described above containing at least one hydrogen atom.

[0203] Therefore, advantageously, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF(R3 It is a compound of ) and in the formula, R 1 , R 2 and R 3 The C1-C atoms may be independently substituted with H, F, I, at least one fluorine atom and / or at least one iodine atom. 10 C3-C which may be substituted with an alkyl group and at least one fluorine atom and / or at least one iodine atom. 10 Selected from the group consisting of cycloalkyl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is I or a group as described above containing at least one iodine atom.

[0204] Preferably, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF(R 3 It is a compound of ) and in the formula, R 1 , R 2 and R 3 C1-C may be independently substituted with H, F, I, 1 to 10 fluorine atoms and / or at least 1 iodine atom. 10 C3-C which may be substituted with alkyl groups and 1 to 10 fluorine atoms and / or at least 1 iodine atom. 10 Selected from the group consisting of cycloalkyl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is I or a group as described above containing at least one iodine atom.

[0205] In particular, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF(R 3 It is a compound of ) and in the formula, R 1 , R 2 and R 3The C1-C atoms may be independently substituted with H, F, I, 1 to 5 fluorine atoms and / or at least 1 iodine atom. 10 C3-C which may be substituted with alkyl groups and 1 to 5 fluorine atoms and / or at least 1 iodine atom. 10 Selected from the group consisting of cycloalkyl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is I or a group as described above containing at least one iodine atom.

[0206] According to a preferred embodiment, the hydrofluoroalkane is of formula (I)(R 1 )(R 2 )CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, and C1-C, which are independent of each other. 10 Perfluoroalkyl groups and C3-C 10 Selected from the group consisting of perfluorocycloalkyl groups. Preferably, the hydrofluoroalkane is of formula (I)(R 1 )(R 2 )CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, C1-C5 perfluoroalkyl groups and C5-C 10 Selected from the group consisting of perfluorocycloalkyl groups.

[0207] In this embodiment, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )C(R 3 ) is a compound of I, in which R 1 and R 2 These are H, F, and C1-C, which are independent of each other. 10 Perfluoroalkyl groups and C3-C 10The iodofluoroalkane compound is selected from the group consisting of perfluorocycloalkyl groups. Preferably, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )C(R 3 ) is a compound of I, in which R 1 and R 2 These are H, F, C1-C5 perfluoroalkyl groups and C5-C 10 Selected from the group consisting of perfluorocycloalkyl groups.

[0208] According to another preferred embodiment, the hydrofluoroalkane is of formula (I)(R 1 )(R 2 )CF(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 10, but the substituent R 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is H. Preferably, the hydrofluoroalkane is of formula (I)(R 1 )(R 2 )CF(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is H.

[0209] In this embodiment, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF(R 3 It is a compound of ) and in the formula, R 1 , R 2 and R 3 These are H, F, I, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F (where n is an integer from 1 to 10), however, the substituent R 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is I. Preferably, the iodofluoroalkane compound is of formula (II)(R 1 )(R 2 )CF(R 3 It is a compound of ) and in the formula, R 1 , R 2 and R 3 These are H, F, I, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 H and I are independent of each other and independent of each unit n. A group consisting of and F is selected, where n is an integer from 1 to 5, but the substituent R is selected. 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is I.

[0210] According to another preferred embodiment, the hydrofluoroalkane is CH3F, CH2F2, CHF3, CH2F-CH3, CHF2-CH3, CH2F-CH2F, CF3-CH3, CHF2-CH2F, CF3-CH2F, CHF2-CHF2, CF3-CHF2, CH2F-CH2-CH3, CH3-CHF-CH3, CH2F-CH2-CH2F, CHF2-CH2-C H3, CH2F-CHF-CH3, CH3-CF2-CH3, CHF2-CH2-CH2F, CF3-CH2-CH3, CH2F-CHF-CH2F, CHF2-CHF-CH3, CH2 F-CF2-CH3, CHF2-CH2-CHF2, CF3-CH2-CH2F, CHF2-CHF-CH2F, CF3-CHF-CH3, CH2F-CF2-CH2F, CHF2-CF Selected from the group consisting of 2-CH3, CF3-CH2-CHF2, CHF2-CHF-CHF2, CF3-CHF-CH2F, CHF2-CF2-CH2F, CF3-CF2-CH3, CF3-CH2-CF3, CF3-CHF-CHF2, CHF2-CF2-CHF2, CF3-CF2-CH2F, CF3-CHF-CF3, and CF3-CF2-CHF2, and TivoliCH2 The group is selected from F2, CHF3, CHF2-CH3, CF3-CH3, CF3-CH2F, CF3-CHF2, CH2F-CHF-CH3, CF3-CH2-CH3, CF3-CH2-CH2F, CF3-CHF-CH3, CF3-CH2-CHF2, CF3-CHF-CH2F, CF3-CH2-CF3, CF3-CHF-CHF2, and CF3-CHF-CF3.

[0211] In this preferred embodiment, the iodo-fluoroalkane compound is CH2FI, CHFI2, CHF2I, CF2I2, CF3I, CHFI-CH3, CH2F-CH2I, CFI2-CH3, CH2F-CHI2, CHFI-CH2I, CF2I-CH3, CHF2-CH2I, CHF2-CHI2, CF2I-CH2I, CHFI-CH2F, CFI2-CH2F, CHFI-CHFI, CF3-CH2I, CF3-CHI2, CF2I-CH2F, CHF2-CHFI, CHF2-CFI2, CF2I-CHFI, CF3-CHFI, CF3-CFI2, CF2I-CHF2, CF2I-CF2I, CF3-CF2I, CHFI-CH2-CH3, CH2F-CHI-CH3, CH2F-CH2-CH2I, CFI2-CH2-CH3, CH2F-CI2-CH3, CH2F-CH2-CHI2, CHFI-CHI-CH3, CHFI-CH2-CH2I, CH2F-CHI-CH2I, CH2I-CHF-CH3, CH3-CFI-CH3, CHI2-CHF-CH3, CH2I-CFI-CH3, CH2I-CHF-CH2I, CHFI-CH2-CH2F, CH2F-CHI-CH2F, CFI2-CH2-CH2F, CH2F-CI2-CH2F, CHFI-CHI-CH2F, CHFI-CH2-CHFI, CF2I-CH2-CH3, CHF2-CHI-CH3, CHF2-CH2-CH2I, CHF2-CI2-CH3, CHF2-CH2-CHI2, CF2I-CHI-CH3, CF2I-CH2-CH2I, CHF2-CHI-CH2I, CHFI-CHF-CH3, CH2F-CFI-CH3, CH2F-CHF-CH2I, CFI2-CHF-CH3, CH2F-CHF-CHI2, CHFI-CFI-CH3, CHFI-CHF-CH2I, CH2F-CFI-CH2I, CH2I-CF2-CH3, CHI2-CF2-CH3, CH2I-CF2-CH2I, CF2I-CH2-CH2F, CHF2-CHI-CH2F, CHF2-CH2-CHFI, CHF2-CI2-CH2F, CHF2-CH2-CFI2, CF2I-CHI-CH2F, CF2I-CH2-CHFI, CHF2-CHI-CHFI, CF3-CHI-CH3, CF3-CH2-CH2I, CF3-CI2-CH3, CF3-CH2-CHI2, CF3-CHI-CH2I, CHFI-CHF-CH2F,Selected from the group consisting of CH2F-CFI-CH2F, CFI2-CHF-CH2F, CHFI-CFI-CH2F, CHFI-CHF-CHFI, CF2I-CHF-CH3, CHF2-CFI-CH3, CHF2-CHF-CH2I, CHF2-CHF-CHI2, CF2I-CFI-CH3, CF2I-CHF-CH2I, CHF2-CFI-CH2I, CHFI-CF2-CH3, CH2F-CF2-CH2I, CFI2-CF2-CH3, CH2F-CF2-CHI2, CHFI-CF2-CH2I, CF2I-CH2-CHF2, CHF2-CHI-CHF2, CHF2-CI2-CHF2, CF2I-CHI-CHF2, CF2I-CH2-CF2I, CF3-CHI-CH2F, CF3-CH2-CHFI, CF3-CI2-CH2F, CF3-CH2-CFI2, CF3-CHI-CHFI, CF2I-CHF-CH2F, CHF2-CFI-CH2F, CHF2-CHF-CHFI, CHF2-CHF-CFI2, CF2I-CFI-CH2F, CF2I-CHF-CHFI, CHF2-CFI-CHFI, CF3-CFI-CH3, CF3-CHF-CH2I, CF3-CHF-CHI2, CF3-CFI-CH2I, CHFI-CF2-CH2F, CFI2-CF2-CH2F, CHFI-CF2-CHFI, CF2I-CF2-CH3, CHF2-CF2-CH2I, CHF2-CF2-CHI2, CF2I-CF2-CH2I, CF3-CHI-CHF2, CF3-CH2-CF2I, CF3-CI2-CHF2, CF3-CHI-CF2I, CF2I-CHF-CHF'2, CHF2-CFI-CHF2, CF2I-CFI-CHF2, CF2I-CHF-CF2I, CF3-CFI-CH2F, CF3-CHF-CHFI, CF3-CHF-CFI2, CF3-CFI-CHFI, CF2I-CF2-CH2F, CHF2-CF2-CHFI, CHF2-CF2-CFI2, CF2I-CF2-CHFI, CF3-CF2-CH2I, CF3-CF'2-CHI2, CF3-CHI-CF3, CF3-CI2-CF3, CF3-CFI-CHF2, CF3-CHF-CF2I, CF3-CFI-CF2I, CF2I-CF2-CHF2, CF2I-CF2-CF2I, CF3-CF2-CHFI, CF3-CF2-CFI2, CF3-CFI-CF3, CF3-CF2-CF2I; preferably,The iodofluoroalkane compounds mentioned above are CHF2I, CF2I2, CF3I, CF2I-CH3, CHF2-CH2I, CHF2-H2I, CF2I-CH2I, CF3-CH2I, CF3-H2I, CF3-CHFI, CF3-CFI2, CF3-CF2I, CHFI-CHF-CH3, CH2F-CFI-CH3, CH2F-CHF-CH2I, CFI2-CHF-CH3, and CH2F-CHF-C HI2, CHFI-CFI-CH3, CHFI-CHF-CH2I, CH2F-CFI-CH2I, CF3-CHI-CH3, CF3-CH2-CH2I, CF3-CI2-CH3, CF3-CH2-C HI2, CF3-CHI-CH2I, CF3-CHI-CH2F, CF3-CH2-CHFI, CF3-CI2-CH2F, CF3-CH2-CFI2, CF3-CHI-CHFI, CF3-CFI-C H3, CF3-CHF-CH2I, CF3-CHF-CHI2, CF3-CFI-CH2I, CF3-CHI-CHF2, CF3-CH2-CF2I, CF3-CI2-CHF2, CF3-CHI-CF 2I, CF3-CFI-CH2F, CF3-CHF-CHFI, CF3-CHF-CFI2, CF3-CFI-CHFI, CF3-CHI-CF3, CF3-CI2-CF3, CF3-CFI-CHF2 The iodofluoroalkane compound is selected from the group consisting of CF3-CHF-CF2I, CF3-CFI-CF2I, and CF3-CFI-CF3; preferably, the iodofluoroalkane compound is selected from the group consisting of CH2FI, CHF2I, CF3I, CHFI-CH3, CF2I-CH3, CHFI-CH2F, CF3-CH2I, CF2I-CH2F, CF3-CHFI, CF2I-CHF2, CF3-CF2I, CHFI-CH2-CH3, CH, 3-CFI-CH3, CHFI-CH2-CH2F, CF2I-CH2-CH3, CHFI-CHF-CH3, CH2I-CF2-CH3, CF2I-CH2-CH2F, CF3-CH2-CH2I, CHFI-CHF-CH2F, CF2I-CHF-CH3, CHFI-CF2-CH3, CF2I-CH2- CHF2, CF3-CH2-CHFI, CF2I-CHF-CH2F, CF3-CFI-CH3, CHFI-CF2-CH2F, CF2I-CF2-CH3, CF3-CH2-CF2I, CF2I-CHF-CHF2, CF3-CHF-CHFI, CF2I-CF2-CH2F, CF3-CF2-CH2I, CF The iodofluoroalkane compound is selected from the group consisting of 3-CHI-CF3, CF3-CHF-CF2I, CF2I-CF2-CHF2, CF3-CF2-CHFI, CF3-CFI-CF3, and CF3-CF2-CF2I; in particular, the iodofluoroalkane compound is selected from the group consisting of CHF2I, CF3I, CF2I-CH3, CF3-CH2I, CF3-CHFI, CF3-CF2I, CHFI-CHF-CH3, CF3-CH2-CH2I, CF3-CH2-CHFI, CF3-CFI-CH3, CF3-CH2-CF2I, CF3-CHF-CHFI, CF3-CHI-CF3, CF3-CHF-CF2I, and CF3-CFI-CF3.

[0212] In a particularly preferred embodiment, step a) of the method involves one of the following reactions: - Converting CH2F2 to CHF2I, CF2I2, or a mixture of both, preferably CHF2I; - Converting CF3 to CF3I; - Converting CHF2-CH3 to CF2I-CH3, CHF2-CH2I, CHF2-CHI2, CF2I-CH2I, or a mixture thereof, preferably CF2I-CH3; - Converting CF3-CH3 to CF3-CH2I, CF3-CHI2, or a mixture of both, preferably CF3-CH2I; - Converting CF3-CH2F to CF3-CHFI, CF3-CFI2, or a mixture of both, preferably CF3-CHFI; - Converting CF3-CHF2 to CF3-CF2I; - Converting CH2F-CHF-CH3 to CHFI-CHF-CH3, CH2F-CFI-CH3, CH2F-CHF-CH2I, CFI2-CHF-CH3, CH2F-CHF-CHI2, CHFI-CFI-CH3, CHFI-CHF-CH2I, CH2F-CFI-CH2I, or a mixture thereof, preferably CHFI-CHF-CH3; - Converting CF3-CH2-CH3 to CF3-CHI-CH3, CF3-CH2-CH2I, CF3-CI2-CH3, CF3-CH2-CHI2, CF3-CHI-CH2I, or a mixture thereof, preferably CF3-CH2-CH2I; - Converting CF3-CH2-CH2F to CF3-CHI-CH2F, CF3-CH2-CHFI, CF3-CI2-CH2F, CF3-CH2-CFI2, CF3-CHI-CHFI, or a mixture thereof, preferably CF3-CH2-CHFI; - Converting CF3-CHF-CH3 to CF3-CFI-CH3, CF3-CHF-CH2I, CF3-CHF-CHI2, CF3-CFI-CH2I, or a mixture thereof, preferably CF3-CFI-CH3; - Converting CF3-CH2-CHF2 to CF3-CHI-CHF2, CF3-CH2-CF2I, CF3-CI2-CHF2, CF3-CHI-CF2I, or a mixture thereof, preferably CF3-CH2-CF2I; - Converting CF3-CHF-CH2F to CF3-CFI-CH2F, CF3-CHF-CHFI, CF3-CHF-CFI2, CF3-CFI-CHFI, or a mixture thereof, preferably CF3-CHF-CHFI; - Converting CF3-CH2-CF3 to CF3-CHI-CF3 or CF3-CI2-CF3 or a mixture of both, preferably CF3-CHI-CF3; - Converting CF3-CHF-CHF2 to CF3-CFI-CHF2, CF3-CHF-CF2I, CF3-CFI-CF2I, or a mixture thereof, preferably CF3-CHF-CF2I; or - Converting CF3-CHF-CF3 to CF3-CFI-CF3.

[0213] Preferably, step a) is carried out in the presence of anhydrous hydrofluoroalkane. Herein, the term “anhydrous” refers to a hydrofluoroalkane containing less than 500 ppm of water, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, more precisely less than 10 ppm, preferably less than 5 ppm, and preferentially, the hydrofluoroalkane is water-free. The use of anhydrous iodine and anhydrous hydrofluoroalkane in this method prevents the formation of impurities and improves the reaction selectivity.

[0214] Preferably, iodine (I2) is brought into contact with the hydrofluoroalkane in a stoichiometric amount or more. For example, the molar ratio of I2 to hydrofluoroalkane is 1 to 50, preferably 2 to 25, and particularly 5 to 20.

[0215] Alternatively, the iodine may be deficient relative to the hydrofluoroalkane. In that case, flows A and B2 contain the unreacted hydrofluoroalkane instead of unreacted iodine. Therefore, the compound recycled to step a) is the hydrofluoroalkane.

[0216] Step a) can be carried out with or without the catalyst.

[0217] According to certain embodiments, the catalyst is selected from alkali metal or alkaline earth metal salts or mixtures thereof. The alkali metal or alkaline earth metal is preferably selected from Li, Na, K, Cs, Mg, and Ca. The anion that associates with the metal is F - Cl - , I -or CO3 2- Preferably, the catalyst is NaI or KI. Preferably, the catalyst is 20m 2 / g to 1000m 2 Specific surface area between / g, especially 20m² 2 / g to 300m 2 It has a specific surface area between / g. The catalyst content is 1% to 30% by weight relative to the hydrofluoroalkane. The catalyst is preferred in the case of a liquid-phase reaction.

[0218] According to another specific embodiment, the catalyst may be selected from the group consisting of oxides, oxyhalides, or halides of metals or metalloids from groups 4 to 15 of the periodic table. The catalyst may be an oxide, oxyhalide, or halide of chromium or aluminum, and in particular, the halide is a fluoride. More specifically, the catalyst may be chromium fluoride, chromium oxyfluoride, or chromium oxide. Preferably, chromium oxyfluoride or aluminum oxyfluoride has a fluorine content of 10% to 50% by weight, preferably 20% to 50% by weight, and particularly 30% to 50% by weight. The fluorine content is measured by ion measurement, by the weight change of the catalyst, or by any other quantitative method known to those skilled in the art. The chromium oxyfluoride or chromium fluoride catalyst is preferably 15m 2 / g to 100m 2 It has a specific surface area of ​​ / g. The chromium oxide catalyst is preferably 100m 2 / g to 300m 2 It has a specific surface area of ​​ / g. The specific surface area is measured using a Micromeritics Gemini 2360 instrument with a standard 5-point method (BET method). When the catalyst is chromium oxide, chromium oxyfluoride, or chromium fluoride, it may contain 0.5% to 10% by weight of a co-catalyst relative to the total weight of the catalyst. The co-catalyst is selected from Cr, Ni, Zn, Ti, V, Zr, Mo, Ge, Sn, Pb, and Mg. The catalyst content is 0.01% to 20% by weight, particularly 0.1% to 10% by weight, relative to the hydrofluoroalkane. These catalysts are preferred for carrying out step a) in the gas phase.

[0219] According to another specific embodiment, the catalyst may be an antimony, iron, titanium, or tin-based catalyst, for example, an antimony halide, iron, titanium, or tin-based catalyst. Thus, the catalyst may be SbCl5, SbF5, FeCl3, TiCl4, or SnCl4. The catalyst content is preferably 0.01% to 50% by weight, particularly 0.1% to 30% by weight, relative to the hydrofluoroalkane. These catalysts can be used in either the liquid or gas phase.

[0220] Therefore, preferred catalysts for carrying out step a) are selected from the group consisting of SbCl5, SbF5, FeCl3, TiCl4, SnCl4, NaI, KI, Cr2O3, Al2O3, chromium oxyfluoride, aluminum oxyfluoride, chromium fluoride, and aluminum fluoride.

[0221] All of the above catalysts can be deposited on a porous support. The porous support may be selected from activated carbon, graphite, alumina, and alumina fluoride. When supported, the catalyst is present in a mass content of 1% to 50% of the total weight of the catalyst and support.

[0222] The catalyst may be activated before use in step a) of this method. Activation preferably involves treating the catalyst with a flow of HF, Cl2, I2, or O2, or a mixture thereof.

[0223] The catalyst may become inactive over time. Therefore, step a) may be carried out in the presence of oxygen or air, or in the presence of an oxygen-nitrogen mixture. When oxygen is used in step a), the oxygen is present in an amount of 0.005 mol% to 10 mol% relative to the molar amount of hydrofluoroalkane.

[0224] The catalyst may also be regenerated after the method has been carried out. The regeneration step may include bringing the catalyst into contact with a flow of oxygen or air at a temperature of 200°C to 700°C.

[0225] Step a) can be performed in either the liquid or gas phase.

[0226] When carried out in the gas phase, step a) is performed at a temperature of 250°C to 700°C, preferably 300°C to 600°C.

[0227] Furthermore, when carried out in the liquid phase, step a) is performed at a temperature of 50°C to 300°C, preferably 50°C to 280°C.

[0228] Furthermore, if step a) is carried out in the liquid phase, it is carried out in the presence of a polar aprotic solvent S1. Preferably, the solvent S1 is anhydrous. The term “anhydrous” here means solvent S1 containing less than 500 ppm of water, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, more precisely less than 10 ppm, preferably less than 5 ppm, and preferentially, the solvent S1 does not contain water. The solvent S1 has a boiling point from 0°C to 250°C, preferably from 20°C to 250°C, particularly from 20°C to 200°C. The solvent S1 is selected from the group consisting of acetic acid, CCl4, chloroform, dichloromethane, sulfolane, tetramethylene sulfone, N,N-dimethylformamide, dimethyl sulfoxide, N,N-dimethylacetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone, and mixtures thereof.

[0229] Step b) of this method Subsequently, flow A is separated to form a first flow B1 containing the iodofluoroalkane compound and a flow containing unreacted iodine. Both flow B1 and flow B2 may contain impurities, reaction by-products, or unreacted hydrofluoroalkanes. Both flow B1 and flow B2 may optionally contain hydrogen iodide. Preferably, flow B1 is subjected to a further purification step to obtain a purified flow B1 containing the iodofluoroalkane compound. Stream B2 can also be subjected to a further purification step to separate unreacted iodine and any potentially present hydrogen iodide. Preferably, after separation and possible purification steps, the content of the iodofluoroalkane compound in flow B1 is greater than 90%, advantageously greater than 92%, preferably greater than 94%, more preferably greater than 96%, particularly greater than 98%, and more precisely greater than 99%.

[0230] The flow A is preferably separated and / or purified by distillation, azeotropic distillation, pressurized distillation, extractive distillation, cold separation, absorption into a solvent, or a combination thereof.

[0231] Flow A may also be separated or purified by contact with an adsorbent. The adsorbent can be a molecular sieve or zeolite having pore openings with an average diameter between 3 angstroms and 11 angstroms, preferably between 4 angstroms and 10 angstroms, and more preferably between 5 angstroms and 10 angstroms.

[0232] Step c) of this method Step c) of this method includes recirculating flow B2 back to step a). This recirculation step improves the overall yield of the method (a better conversion rate), saves expensive reagents (and catalysts), and minimizes the environmental impact. Without this recirculation step, unreacted iodine would have to be incinerated, thus increasing the carbon dioxide emissions of the method.

[0233] If stream B1 contains unreacted hydrofluoroalkanes, the reagents can be removed from stream B1 and recycled back to step a).

[0234] This method can be performed continuously, in batches, or in semi-batches.

[0235] Preferably, in order to avoid corrosion problems, the reactor in which step a) is carried out is made of a material that includes a base layer made of material M1 and an inner layer made of material M2.

[0236] Advantageously, material M2 contains at least 40% by weight of nickel relative to the total weight of material M2. Preferably, material M2 contains at least 45% by weight of nickel, more preferably at least 50% by weight of nickel, particularly at least 55% by weight of nickel, especially at least 60% by weight of nickel, preferably at least 65% by weight of nickel, and more preferably at least 70% by weight of nickel relative to the total weight of material M2.

[0237] Material M2 may also contain chromium in an amount of less than 35% by weight, preferably less than 30% by weight, more preferably less than 20% by weight, more preferably less than 15% by weight, particularly less than 10% by weight, and more precisely less than 5% by weight relative to the total weight of Material M2.

[0238] Material M2 may also contain molybdenum in an amount of less than 35% by weight, preferably less than 30% by weight, more preferably less than 20% by weight, more preferably less than 15% by weight, particularly less than 10% by weight, and more precisely less than 5% by weight relative to the total weight of material M2.

[0239] Preferably, material M2 is Monel®, Hastelloy®, Inconel®, or Incoloy®.

[0240] According to a preferred embodiment, material M1 comprises at least 70% by weight of iron, advantageously at least 75% by weight, preferably at least 80% by weight, more preferably at least 85% by weight, particularly at least 90% by weight, and more precisely at least 95% by weight of iron relative to the total weight of material M1.

[0241] Material M1 may also contain less than 2% by weight, advantageously less than 1.5% by weight, preferably less than 1% by weight, more preferably less than 0.75% by weight, particularly less than 0.5% by weight, more precisely less than 0.2% by weight, and preferably less than 0.1% by weight of carbon relative to the total weight of Material M1. More specifically, Material M1 may contain between 0.01% and 0.2% by weight of carbon relative to the total weight of Material M1.

[0242] Preferably, the base layer and the inner layer are arranged to face each other by molten or low-temperature plating, hot or cold rolling, or pressure welding.

[0243] Examples Example 1 The apparatus used was a 500 ml autoclave made of Hastelloy C276, equipped with a stirrer, heater, and temperature control system. The autoclave was degassed and inactivated with nitrogen, and the following anhydrous components were introduced sequentially: 250 mL of sulfolane, 15.0 g (0.1 mol) of sodium iodide, 67.0 g (0.5 mol) of CF3-CH2-CHF2 (HFC-245fa), and 0.0 g (0.79 mol) of anhydrous I2200. The reaction medium was heated to 170°C to 180°C while stirring. After reacting for 6 hours with stirring, the sample was taken, washed, dried, and then analyzed by gas chromatography (area percentage method). The conversion rate of CF3-CH2-CHF2 was 88%, and the selectivity for CF3-CH2-CF2I was 92%. Small amounts of CF3-CHI-CHF2, CF3-CI2-CHF2, and CF3-CHI-CF2I were observed.

[0244] Example 2 A reactor consisting of an Inconel 600 tube with an inner diameter of 28 mm and a length of 640 mm, placed vertically inside a tubular furnace, is used. The catalyst bed consists of a 40 mm corundum layer at the bottom, followed by an 85 mm chromium oxyfluoride catalyst layer containing 15% to 25% by weight of fluorine. The catalyst was pre-activated at a temperature of 350°C in the presence of an O2 gas stream. A gas stream of CF3-CHF-CH2F(HFC-245eb) and anhydrous I2 (molar ratio of CF3-CHF-CH2F / I2 = 1 / 2) passes over the catalyst at a temperature of 550°C. The gas is washed at the outlet of the reactor and then dried and condensed in a cold trap. A sample is taken and analyzed by gas chromatography (area percentage method). The conversion rate of CF3-CHF-CH2F(HFC-245eb) is 94%, and the selectivity for CF3-CHF-CHFI is 98%. Small amounts of CF3-CFI-CH2F, CF3-CHF-CFI2, and CF3-CFI-CHFI were observed.

[0245] Equivalent conversion rates and selectivity values ​​were obtained for the conversion of CF3-CHF-CH3 to CF3-CFI-CH3, CF3-CH2-CH2F to CF3-CH2-CHFI, and CF3-CHF-CHF2 to CF3-CHF-CF2I.

[0246] Invention IV Summary of Invention IV According to a first aspect, the present invention relates to a method for producing an iodofluoroolefin compound, comprising the following steps: a) Equation (I) (R 1 )(R 2 )C=CH(R 3 The fluoroolefin of ) is brought into contact with iodine (I2) in the liquid phase, and formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3 The process of forming a diiodofluoroalkane compound; b) The diiodofluoroalkane compound of formula (II) obtained in step a) is subjected to a deiodation reaction, resulting in formula (III)(R 1 )(R 2 )C=C(I)(R 3A step of forming a flow B containing the iodofluoroolefin, wherein substituent R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 A step of forming flow B, wherein at least one of the groups is F or a group as described above containing at least one fluorine atom.

[0247] According to a preferred embodiment, R 1 , R 2 and R 3 These are H, F, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, however, R 1 , R 2 and R 3 The condition is that both are not H at the same time.

[0248] According to a preferred embodiment, R 1 , R 2 and R 3 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 10, but the substituent R 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0249] According to a preferred embodiment, the fluoroolefin is CHF=CH2, CF2=CH2, CHF=CHF, CF2=CHF, CH3-CF=CH2, CH3-CH=CHF, CH2F-CH=CH2, CH3-CF=CHF, CH2F-CF=CH2, CH3-CH=CF2, CH2F-CH=CHF, CHF2-CH=CH2, CH3-CF=CF2, CH2F-CF=CHF, CHF2-CF=CH2, CH2F-CH=CF2, CHF2-CH=C The fluoroolefin is selected from the group consisting of HF, CF3-CH=CH2, CH2F-CF=CF2, CHF2-CF=CHF, CF3-CF=CH2, CHF2-CH=CF2, CF3-CH=CHF, CHF2-CF=CF2, CF3-CF=CHF, and CF3-CH=CF2; advantageously, the fluoroolefin is selected from the group consisting of CF2=CH2, CF2=CHF, CF3-CH=CH2, CF3-CF=CH2, CF3-CH=CHF, and CF3-CF=CHF; The diiodofluoroalkane compounds include CHFI-CH2I, CF2I-CH2I, CHFI-CHFI, CF2I-CHFI, CH3-CFI-CH2I, CH3-CHI-CHFI, CH2F-CHI-CH2I, CH3-CFI-CHFI, CH2F-C FI-CH2I, CH3-CHI-CF2I, CH2F-CHI-CHFI, CHF2-CHI-CH2I, CH3-CFI-CF2I, CH2F-CFI-CHFI, CHF2-CFI-CH2I, CH2F-CHI-CF2I, CHF2-CHI-CHFI, The compounds are selected from the group consisting of CF3-CHI-CH2I, CH2F-CFI-CF2I, CHF2-CFI-CHFI, CF3-CFI-CH2I, CHF2-CHI-CF2I, CF3-CHI-CHFI, CHF2-CFI-CF2I, CF3-CFI-CHFI, and CF3-CHI-CF2I; advantageously, the diiodofluoroalkane compounds are selected from the group consisting of CF2I-CH2I, CF2I-CHFI, CF3-CHI-CH2I, CF3-CFI-CH2I, CF3-CHI-CHFI, and CF3-CFI-CHFI; The iodofluoroolefins are CFI=CH2, CHF=CHI, CF2=CHI, CFI=CHF, CF2=CFI, CH2=CF-CH2I, CH3-CF=CHI, CH2=CH-CHFI, CH3-CI=CHF, CH3-CH=CFI, CHF=CH-CH 2I, CH2F-CI=CH2, CH2F-CH=CHI, CH2=CF-CHFI, CH3-CF=CFI, CHF=CF-CH2I, CH2F-CF=CHI, CH2=CH-CF2I, CH3-CI=CF2, CHF=CH-CHFI, CH2F-CI=CHF, CH 2F-CH=CFI, CF2=CH-CH2I, CHF2-CI=CH2, CHF2-CH=CHI, CH2=CF-CF2I, CHF=CF-CHFI, CH2F-CF=CFI, CF2=CF-CH2I, CHF2-CF=CHI, CHF=CH-CF2I, CH2F- CI=CF2, CF2=CH-CHFI, CHF2-CI=CHF, CHF2-CH=CFI, CF3-CI=CH2, CF3-CH=CHI, CHF=CF-CF2I, CF2=CF-CHFI, CHF2-CF=CFI, CF3-CF=CHI, CF2=CH-CF2I The iodofluoroolefin is selected from the group consisting of CHF2-CI=CF2, CF3-CI=CHF, CF3-CH=CFI, CF2=CF-CF2I, CF3-CF=CFI, and CF3-CI=CF2; preferably, the iodofluoroolefin is selected from the group consisting of CHI=CHF, CF2=CHI, CFI=CHF, CF2=CFI, CH3-CF=CHI, CH3-CI=CHF, CH2F-CI=CH2, CH2=CF-CHFI, CH2F-CF=CHI, CH3-CI=CF2, CH2F-CI=CHF, CHF2-CI=CH2, CH2=CF-CF2I, and CHF=CF- The iodofluoroolefin is selected from the group consisting of CHFI, CHF2-CF=CHI, CH2F-CI=CF2, CHF2-CI=CHF, CF3-CI=CH2, CHF=CF-CF2I, CHF2-CF=CFI, CF3-CF=CHI, CHF2-CI=CF2, CF3-CI=CHF, CF2=CF-CF2I, CF3-CF=CFI, and CF3-CI=CF2; in particular, the iodofluoroolefin is selected from the group consisting of CF2=CHI, CF2=CFI, CF3-CI=CH2, CF3-CF=CHI, CF3-CI=CHF, and CF3-CF=CFI.

[0250] According to a preferred embodiment, flow B also includes HI, and the method includes a step of separating the iodofluoroolefin from the HI.

[0251] According to a preferred embodiment, the diiodofluoroalkane compound is dried and optionally purified before being used in step b).

[0252] According to a preferred embodiment, step a) is carried out in the liquid phase in the presence of a solvent selected from the group consisting of aqueous potassium iodide, ethers, fluorinated ethers, alcohols, fluorinated alcohols, esters, aromatic solvents, fluorinated aromatic solvents, halogenated solvents, and mixtures thereof.

[0253] According to a preferred embodiment, step b) is carried out using a basic aqueous mixture; advantageously, the mixture comprises a base selected from alkali metals or alkaline earth metal hydroxides; preferably, the mixture has an alkali metal or alkaline earth metal hydroxide content of 20% to 80% by weight of the total weight of the mixture.

[0254] According to a preferred embodiment, step b) is carried out in the gas phase, and the deiodide catalyst is selected from the group consisting of oxides, oxyhalides, or halides of metals or metalloids from groups 4 to 15 of the periodic table; preferably, it is selected from the group consisting of oxides, oxyhalides, or halides of aluminum, iron, or chromium.

[0255] According to a second aspect, the present invention relates to formula (I)(R 1 )(R 2 )C=CH(R 3 The fluoroolefin of ) is brought into contact with iodine (I2) in the liquid phase, and formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3 )(wherein, R 1 , R 2 and R 3The present invention provides a method for producing a diiodofluoroalkane compound, comprising the step of forming a diiodofluoroalkane compound (as described above). According to a preferred embodiment, the diiodofluoroalkane compound is CHFI-CH2I, CF2I-CH2I, CHFI-CHFI, CF2I-CHFI, CH3-CFI-CH2I, CH3-CHI-CHFI, CH2F-CHI-CH2I, CH3-CFI-CHFI, CH2F-CFI-CH2I, CH3-CHI-CF2I, CH2F-CHI-CHFI, CHF2-CHI-CH2I, CH3-CFI-CF2I, CH2F-CFI-CHFI, CHF2-CFI-CH2I, CH2F-CHI-CF2I, CHF2-CHI- The iodofluoroalkane compound is selected from the group consisting of CHFI, CF3-CHI-CH2I, CH2F-CFI-CF2I, CHF2-CFI-CHFI, CF3-CFI-CH2I, CHF2-CHI-CF2I, CF3-CHI-CHFI, CHF2-CFI-CF2I, CF3-CFI-CHFI, and CF3-CHI-CF2I; advantageously, the iodofluoroalkane compound is selected from the group consisting of CF2I-CH2I, CF2I-CHFI, CF3-CHI-CH2I, CF3-CFI-CH2I, CF3-CHI-CHFI, and CF3-CFI-CHFI.

[0256] According to a preferred embodiment, the diiodofluoroalkane compound is isolated and purified.

[0257] Modes for carrying out the invention According to a first aspect, the present invention relates to a method for producing an iodofluoroolefin compound. Preferably, the method is based on formula (I)(R 1 )(R 2 )C=CH(R 3 When the fluoroolefin of ) is brought into contact with iodine (I2) in the liquid phase, formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3The method comprises at least one step of forming a diiodofluoroalkane compound of formula (III)(R) obtained in step a). Preferably, the method involves a deiodation reaction of the diiodofluoroalkane compound of formula (II) obtained in step a), thereby forming a compound of formula (III)(R) 1 )(R 2 )C=C(I)(R 3 The process also includes forming a flow B containing the iodofluoroolefin. Substituent R 1 , R 2 and R 3 The details are as follows:

[0258] Therefore, the method includes the following steps: a) Equation (I) (R 1 )(R 2 )C=CH(R 3 The fluoroolefin of ) is brought into contact with iodine (I2) in the liquid phase, and formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3 The process of forming a diiodofluoroalkane compound; b) The diiodofluoroalkane compound of formula (II) obtained in step a) is subjected to a deiodation reaction, resulting in formula (III)(R 1 )(R 2 )C=C(I)(R 3 A step of forming a flow B containing the iodofluoroolefin, wherein substituent R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2or R 3 A step of forming flow B, wherein at least one of the groups is F or a group as described above containing at least one fluorine atom.

[0259] Step a) of this method Step a) of this method requires contacting the fluoroolefin with iodine (I2) in the liquid phase.

[0260] The fluoroolefin is preferably of formula (I)(R 1 )(R 2 )C=CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These C1-C atoms may be independently substituted with H, F, I, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing at least one fluorine atom.

[0261] The fluoroolefin is preferably of formula (I)(R 1 )(R 2 )C=CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing at least one fluorine atom.

[0262] The term "alkyl" refers to a monovalent group derived from linear or branched alkanes containing a specific number of carbon atoms. The term "cycloalkyl" refers to a monovalent group derived from cycloalkanes containing a specific number of carbon atoms. The term "alkenyl" refers to a monovalent group containing a specific number of carbon atoms and at least one carbon-carbon double bond. The term "cycloalkenyl" refers to a monovalent group derived from cycloalkenes containing a specific number of carbon atoms and at least one carbon-carbon double bond in the cyclic portion. The term "aryl" refers to a monovalent group derived from arenes containing a specific number of carbon atoms.

[0263] Preferably, the alkyl, cycloalkyl, alkenyl, cycloalkenyl, or aryl group is not substituted with a functional group other than fluorine. Nevertheless, the group may contain several fluorine atoms on its carbon chain; for example, the group may contain 1 to 10 fluorine atoms, preferably 1 to 5 fluorine atoms.

[0264] Preferably, the fluoroolefin is of formula (I)(R 1 )(R 2 )C=CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, I, and 1 to 10 fluorine atoms. 10Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0265] Preferably, the fluoroolefin is of formula (I)(R 1 )(R 2 )C=CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, and 1 to 10 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0266] Preferably, the fluoroolefin is of formula (I)(R 1 )(R 2 )C=CH(R 3 ) is of the same type, and in the formula, R 1 , R2 and R 3 The C1-C atoms may be independently substituted with H, F, I, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0267] Preferably, the fluoroolefin is of formula (I)(R 1 )(R 2 )C=CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0268] Preferably, the fluoroolefin is of formula (I)(R 1)(R 2 )C=CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, I, C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 or R 3 At least one of them is either F or a perfluoro group as described above.

[0269] Preferably, the fluoroolefin is of formula (I)(R 1) (R 2 )C=CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, and C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 or R 3 At least one of them is either F or a perfluoro group as described above.

[0270] Preferably, the fluoroolefin is of formula (I)(R 1) (R 2 )C=CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 or R 3 At least one of them is either F or a perfluoro group as described above.

[0271] Preferably, the fluoroolefin is of formula (I)(R 1) (R 2 )C=CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 or R 3 At least one of them is either F or a perfluoro group as described above.

[0272] Alternatively, the fluoroolefin is of formula (I)(R 1 )(R 2 )C=CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F, where n is an integer from 1 to 10. 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0273] Preferably, the fluoroolefin is of formula (I)(R 1 )(R 2 )C=CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F (where n is an integer from 1 to 5), however, the substituent R 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0274] Preferably, the fluoroolefin is of formula (I)(R 1 )(R 2 )CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 10, but the substituent R 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0275] Preferably, the fluoroolefin is of formula (I)(R 1 )(R 2 )CH(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0276] According to a preferred embodiment, the fluoroolefin is selected from the group consisting of CHF=CH2, CF2=CH2, CHF=CHF, CF2=CHF, CH3-CF=CH2, CH3-CH=CHF, CH2F-CH=CH2, CH3-CF=CHF, CH2F-CF=CH2, CH3-CH=CF2, CH2F-CH=CHF, CHF2-CH=CH2, CH3-CF=CF2, CH2F-CF=CHF, CHF2-CF=CH2, CH2F-CH=CF2, CHF2-CH=CHF, CF3-CH=CH2, CH2F-CF=CF2, CHF2-CF=CHF, CF3-CF=CH2, CHF2-CH=CF2, CF3-CH=CHF, CHF2-CF=CF2, CF3-CF=CHF, and CF3-CH=CF. Advantageously, the fluoroolefin is selected from the group consisting of CF2=CH2, CF2=CHF, CF3-CH=CH2, CF3-CF=CH2, CF3-CH=CHF, and CF3-CF=CHF.

[0277] The fluoroolefin may have a boiling point of less than 100°C at atmospheric pressure. Advantageously, the fluoroolefin has a boiling point of less than 75°C at atmospheric pressure. Preferably, the fluoroolefin has a boiling point of less than 50°C at atmospheric pressure. More preferably, the fluoroolefin has a boiling point of less than 25°C at atmospheric pressure. In particular, the fluoroolefin has a boiling point of less than 10°C at atmospheric pressure.

[0278] According to a preferred embodiment, step a) can be carried out in the presence of a mixture of fluoroolefins to bring about the co-production of iodofluoroolefins via the corresponding diiodofluoroalkane compounds according to the present method.

[0279] Step a) is given by equation (II)(R 1 )(R 2 )C(I)-CH(I)(R 3 ) enables the generation of diiodofluoroalkane compounds, in which R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, and at least one fluorine atom. 10Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing at least one fluorine atom.

[0280] Preferably, the diiodofluoroalkane compound is of formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3 It is a compound of ) and in the formula, R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, I, and 1 to 10 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0281] Preferably, the diiodofluoroalkane compound is of formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3It is a compound of ) and in the formula, R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, and 1 to 10 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0282] Preferably, the diiodofluoroalkane compound is of formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3 It is a compound of ) and in the formula, R 1 , R 2 and R 3 The C1-C atoms may be independently substituted with H, F, I, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0283] Preferably, the diiodofluoroalkane compound is of formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3 It is a compound of ) and in the formula, R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0284] Preferably, the diiodofluoroalkane compound is of formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3 It is a compound of ) and in the formula, R 1 , R 2 and R 3 These are H, F, I, C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 or R 3 At least one of them is either F or a perfluoro group as described above.

[0285] Preferably, the diiodofluoroalkane compound is of formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3 It is a compound of ) and in the formula, R 1 , R 2 and R 3 These are H, F, and C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 or R 3 At least one of them is either F or a perfluoro group as described above.

[0286] Preferably, the diiodofluoroalkane compound is of formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3 It is a compound of ) and in the formula, R 1 , R 2 and R 3 These are H, F, I, C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 or R 3 At least one of them is either F or a perfluoro group as described above.

[0287] Preferably, the diiodofluoroalkane compound is of formula (II)(R 1 )(R 2 )C(I)-CH(I)(R3 It is a compound of ) and in the formula, R 1 , R 2 and R 3 These are H, F, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 or R 3 At least one of them is either F or a perfluoro group as described above.

[0288] Alternatively, the diiodofluoroalkane compound may be of formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3 It is a compound of ) and in the formula, R 1 , R 2 and R 3 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F, where n is an integer from 1 to 10. 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0289] Preferably, the diiodofluoroalkane compound is of formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3 It is a compound of ) and in the formula, R 1 , R 2 and R3 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F (where n is an integer from 1 to 5), however, the substituent R 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0290] Preferably, the diiodofluoroalkane compound is of formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3 It is a compound of ) and in the formula, R 1 , R 2 and R 3 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 10, but the substituent R 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0291] Preferably, the diiodofluoroalkane compound is of formula (II)(R 1 )(R 2 )C(I)-CH(I)(R 3 It is a compound of ) and in the formula, R 1 , R2 and R 3 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0292] In particular, the diiodofluoroalkane compounds include CHFI-CH2I, CF2I-CH2I, CHFI-CHFI, CF2I-CHFI, CH3-CFI-CH2I, CH3-CHI-CHFI, CH2F-CHI-CH2I, CH3-CFI-CHFI, CH2F-CFI-CH2I, CH3-CHI-CF2I, CH2F-CHI-CHFI, CHF2-CHI-CH2I, CH3-CFI-CF2I, CH2 The diiodofluoroalkane compound is selected from the group consisting of F-CFI-CHFI, CHF2-CFI-CH2I, CH2F-CHI-CF2I, CHF2-CHI-CHFI, CF3-CHI-CH2I, CH2F-CFI-CF2I, CHF2-CFI-CHFI, CF3-CFI-CH2I, CHF2-CHI-CF2I, CF3-CHI-CHFI, CHF2-CFI-CF2I, CF3-CFI-CHFI, and CF3-CHI-CF2I. More specifically, the diiodofluoroalkane compound is selected from the group consisting of CF2I-CH2I, CF2I-CHFI, CF3-CHI-CH2I, CF3-CFI-CH2I, CF3-CHI-CHFI, and CF3-CFI-CHFI.

[0293] Preferably, step a) allows at least one of the following reactions: - The reaction that converts CHF=CH2 to CHFI-CH2I; or - A reaction that converts CF2=CH2 to CF2I-CH2I; or - The reaction that converts CHF=CHF to CHFI-CHFI; or - The reaction that converts CF2=CHF to CF2I-CHFI; or - A reaction that converts CH3-CF=CH2 to CH3-CFI-CH2I; or - The reaction that converts CH3-CH=CHF to CH3-CHI-CHFI; or - A reaction that converts CH2F-CH=CH2 to CH2F-CHI-CH2I; or - The reaction that converts CH3-CF=CHF to CH3-CFI-CHFI; or - A reaction that converts CH2F-CF=CH2 to CH2F-CFI-CH2I; or - The reaction that converts CH3-CH=CF2 to CH3-CHI-CF2I; or - The reaction that converts CH2F-CH=CHF to CH2F-CHI-CHFI; or - The reaction that converts CHF2-CH=CH2 to CHF2-CHI-CH2I; or - The reaction that converts CH3-CF=CF2 to CH3-CFI-CF2I; or - The reaction that converts CH2F-CF=CHF to CH2F-CFI-CHFI; or - The reaction that converts CHF2-CF=CH2 to CHF2-CFI-CH2I; or - The reaction that converts CH2F-CH=CF2 to CH2F-CHI-CF2I; or - The reaction that converts CHF2-CH=CHF to CHF2-CHI-CHFI; or - The reaction that converts CF3-CH=CH2 to CF3-CHI-CH2I; or - The reaction that converts CH2F-CF=CF2 to CH2F-CFI-CF2I; or - The reaction that converts CHF2-CF=CHF to CHF2-CFI-CHFI; or - The reaction that converts CF3-CF=CH2 to CF3-CFI-CH2I; or - The reaction that converts CHF2-CH=CF2 to CHF2-CHI-CF2I; or - The reaction that converts CF3-CH=CHF to CF3-CHI-CHFI; or - The reaction that converts CHF2-CF=CF2 to CHF2-CFI-CF2I; or - The reaction that converts CF3-CF=CHF to CF3-CFI-CHFI; or - A reaction that converts CF3-CH=CF2 to CF3-CHI-CF2I.

[0294] Preferably, step a) is carried out in the absence of a catalyst. Preferably, step a) is carried out in the presence of solvent S1. Preferably, solvent S1 is selected from the group consisting of aqueous potassium iodide, ethers, fluorinated ethers, alcohols, fluorinated alcohols, esters, aromatic solvents, fluorinated aromatic solvents, halogenated solvents, and mixtures thereof. Advantageously, solvent S1 is selected from the group consisting of aqueous potassium iodide, ethyl and methyl ethers, hydrofluoroethers, ethyl and methyl alcohols, ethyl lactate, toluene, xylene, para-chlorotrifluoromethylbenzene, hexafluorobenzene, tetrachloromethane, chloroform, dichloromethane, 1-bromopropane, and mixtures thereof. The use of a solvent in this method makes it possible to avoid clogging problems associated with iodine sublimation and to limit the formation of impurities (such as reaction by-products and polymers derived from fluoroolefins), which makes it possible to achieve a selectivity that is particularly advantageous from an industrial standpoint.

[0295] Preferably, iodine is brought into contact with the fluoroolefin described above in a stoichiometric or greater amount. For example, the molar ratio of I2 / olefin is 0.1 to 50, preferably 0.5 to 25, and particularly 1 to 20.

[0296] Preferably, the oxygen content dissolved in solvent S1 is less than 3000 ppm, advantageously less than 2000 ppm, preferably less than 1000 ppm, more preferably less than 500 ppm, particularly less than 250 ppm, more specifically less than 100 ppm, preferably less than 50 ppm, and preferentially less than 10 ppm. This avoids decomposition of the starting material and the desired product. Solvent S1 preferably has a boiling point of 0°C to 250°C, preferably 20°C to 250°C, and particularly 20°C to 200°C.

[0297] The temperature at which step a) is carried out is 20°C to 280°C, preferably 30°C to 250°C. Step a) can be carried out at a pressure of 0.1 bar to 15 bar, preferably 1 bara to 10 bara (absolute pressure).

[0298] The diiodofluoroalkane compound may be dried before use in step b). This removes any trace amounts of water that may be present. This drying can be carried out by contact with an adsorbent, absorbent, 3-angstrom to 5-angstrom sieve, or zeolite.

[0299] The diiodofluoroalkane compound may be purified before use in step b). This purification may be performed before or after the drying step. This allows for the removal of certain impurities that are difficult to separate from the iodofluoroolefin compound obtained in step b). This step also allows for an increase in the selectivity of step b). Purification can be carried out by distillation, azeotropic distillation, pressurized distillation, extractive distillation, cold separation, absorption into a solvent, contact with an adsorbent, or a combination thereof. Advantageously, the purification of the diiodofluoroalkane compound is performed to produce a stream A in which the content of the diiodofluoroalkane compound is greater than 90%, preferably greater than 92%, preferably greater than 94%, more preferably greater than 96%, particularly greater than 98%, and more precisely greater than 99%. This stream A is then used in step b).

[0300] When step a) is carried out using a mixture of fluoroolefins, purification will yield a mixture of diiodofluoroalkane compounds or a specific diiodofluoroalkane compound, depending on the conditions used for purification.

[0301] The dried diiodofluoroalkane compound may be purified as described above or used as is in step b). For example, if step a) is carried out with a high conversion rate and selectivity, such as over 90%, preferably over 95%, the dried diiodofluoroalkane compound is used as is in step b) without being purified after the drying step. Since the purification step can incur considerable costs, the absence of purification between steps a) and b) may be advantageous from the viewpoint of the overall productivity of this method.

[0302] The diiodofluoroalkane compound used in step b) is preferably anhydrous, that is, the stream containing the diiodofluoroalkane compound used in step b) is anhydrous. The term “anhydrous” here means that the amount of water in the stream containing the diiodofluoroalkane compound and used in step b) is less than 500 ppm by mass, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, more precisely less than 10 ppm, more preferably less than 5 ppm, and preferentially, the diiodofluoroalkane compound or the stream containing it for carrying out step b) is water-free.

[0303] Step b) of this method Step b) of this method involves the deiodation reaction of the diiodofluoroalkane compound of formula (II) obtained in step a), resulting in formula (III)(R 1 )(R 2 )C=C(I)(R 3 This is a step of forming a flow B containing the iodofluoroolefin.

[0304] The iodofluoroolefin obtained in step b) is of formula (III)(R 1 )(R2 )C=C(I)(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These C1-C atoms may be independently substituted with H, F, I, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing at least one fluorine atom.

[0305] The iodofluoroolefin is preferably of formula (III)(R 1 )(R 2 )C=C(I)(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3At least one of them is F or a group as described above containing at least one fluorine atom.

[0306] Preferably, the iodofluoroolefin is of formula (III)(R 1 )(R 2 )C=C(I)(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, I, and 1 to 10 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0307] Preferably, the iodofluoroolefin is of formula (III)(R 1 )(R 2 )C=C(I)(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, and 1 to 10 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0308] Preferably, the iodofluoroolefin is of formula (III)(R 1 )(R 2 )C=C(I)(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 The C1-C atoms may be independently substituted with H, F, I, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0309] Preferably, the iodofluoroolefin is of formula (III)(R 1 )(R 2 )C=C(I)(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are C1-C atoms that may be independently substituted with H, F, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 or R 3 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0310] Preferably, the iodofluoroolefin is of formula (III)(R 1 )(R 2 )C=C(I)(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, I, C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 or R 3 At least one of them is either F or a perfluoro group as described above.

[0311] Preferably, the iodofluoroolefin is of formula (III)(R 1 )(R 2 )C=C(I)(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, and C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl groups, C2-C 10Perfluoroalkenyl group, C3-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 or R 3 At least one of them is either F or a perfluoro group as described above.

[0312] Preferably, the iodofluoroolefin is of formula (III)(R 1 )(R 2 )C=C(I)(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 or R 3 At least one of them is either F or a perfluoro group as described above.

[0313] Preferably, the iodofluoroolefin is of formula (III)(R 1 )(R 2 )C=C(I)(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 or R 3At least one of them is either F or a perfluoro group as described above.

[0314] Alternatively, the iodofluoroolefin is of formula (III)(R 1 )(R 2 )C=C(I)(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F, where n is an integer from 1 to 10. 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0315] Preferably, the iodofluoroolefin is of formula (III)(R 1 )(R 2 )C=C(I)(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F (where n is an integer from 1 to 5), however, the substituent R 1 , R 2 , R 3 , Y 1 , Y 2or Y 3 The condition is that at least one of them is F.

[0316] Preferably, the iodofluoroolefin is of formula (III)(R 1 )(R 2 )C=C(I)(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 10, but the substituent R 1 , R 2 , R 3 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0317] Preferably, the iodofluoroolefin is of formula (III)(R 1 )(R 2 )C=C(I)(R 3 ) is of the same type, and in the formula, R 1 , R 2 and R 3 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , Y 1 , Y 2 or Y3 The condition is that at least one of them is F.

[0318] In particular, the iodofluoroolefins are CFI=CH2, CHF=CHI, CF2=CHI, CFI=CHF, CF2=CFI, CH2=CF-CH2I, CH3-CF=CHI, CH2=CH-CHFI, CH3-CI=CHF, CH3-CH=CFI, CHF=CH- CH2I, CH2F-CI=CH2, CH2F-CH=CHI, CH2=CF-CHFI, CH3-CF=CFI, CHF=CF-CH2I, CH2F-CF=CHI, CH2=CH-CF2I, CH3-CI=CF2, CHF=CH-CHFI, CH2F-CI=CHF, CH2F-CH=CFI, CF2=CH-CH2I, CHF2-CI=CH2, CHF2-CH=CHI, CH2=CF-CF2I, CHF=CF-CHFI, CH2F-CF=CFI, CF2=CF-CH2I, CHF2-CF=CHI, CHF=CH-CF2I, CH2 F-CI=CF2, CF2=CH-CHFI, CHF2-CI=CHF, CHF2-CH=CFI, CF3-CI=CH2, CF3-CH=CHI, CHF=CF-CF2I, CF2=CF-CHFI, CHF2-CF=CFI, CF3-CF=CHI, CF2=CH-CF2 I, CHF2-CI=CF2, CF3-CI=CHF, CF3-CH=CFI, CF2=CF-CF2I, CF3-CF=CFI, CF3-CI=CF2; Preferably, the iodofluoroolefin is selected from the group consisting of CHI=CHF, CF2=CHI, CFI=CHF, CF2=CFI, CH3-CF=CHI, CH3-CI=CHF, CH2F-CI=CH2, CH2=CF-CHFI, CH2F-CF=CHI, CH3-CI=CF2, CH2F-CI=CHF, CHF2-CI=CH2, CH2=CF-CF2I, CHF=CF -Selected from the group consisting of CHFI, CHF2-CF=CHI, CH2F-CI=CF2, CHF2-CI=CHF, CF3-CI=CH2, CHF=CF-CF2I, CHF2-CF=CFI, CF3-CF=CHI, CHF2-CI=CF2, CF3-CI=CHF, CF2=CF-CF2I, CF3-CF=CFI, CF3-CI=CF2; in particular, the iodofluoroolefin is selected from the group consisting of CF2=CHI, CF2=CFI, CF3-CI=CH2, CF3-CF=CHI, CF3-CI=CHF, CF3-CF=CFI.

[0319] Preferably, step b) allows at least one of the following reactions: - The reaction that converts CHFI-CH2I to CHI=CHF; - The reaction that converts CF2I-CH2I to CF2=CHI; - The reaction that converts CHFI-CHFI to CFI=CHF; - The reaction that converts CF2I-CHFI to CF2=CFI; - The reaction that converts CH3-CFI-CH2I to CH3-CF=CHI; - The reaction that converts CH3-CHI-CHFI to CH3-CI=CHF; - A reaction that converts CH2F-CHI-CH2I to CH2F-CI=CH2; - A reaction that converts CH3-CFI-CHFI to CH2=CF-CHFI; - The reaction that converts CH2F-CFI-CH2I to CH2F-CF=CHI; - A reaction that converts CH3-CHI-CF2I to CH3-CI=CF2; - The reaction that converts CH2F-CHI-CHFI to CH2F-CI=CHF; - A reaction that converts CHF2-CHI-CH2I to CHF2-CI=CH2; - A reaction that converts CH3-CFI-CF2I to CH2=CF-CF2I; - The reaction that converts CH2F-CFI-CHFI to CHF=CF-CHFI; - The reaction that converts CHF2-CFI-CH2I to CHF2-CF=CHI; - A reaction that converts CH2F-CHI-CF2I to CH2F-CI=CF2; - The reaction that converts CHF2-CHI-CHFI to CHF2-CI=CHF; - The reaction that converts CF3-CHI-CH2I to CF3-CI=CH2; - The reaction that converts CH2F-CFI-CF2I to CHF=CF-CF2I; - The reaction that converts CHF2-CFI-CHFI to CHF2-CF=CFI; - The reaction that converts CF3-CFI-CH2I to CF3-CF=CHI; - The reaction that converts CHF2-CHI-CF2I to CHF2-CI=CF2; The reaction that converts -CF3-CHI-CHFI to CF3-CI=CHF; - A reaction that converts CHF2-CFI-CF2I to CF2=CF-CF2I; - The reaction that converts CF3-CFI-CHFI to CF3-CF=CFI; - A reaction that converts CF3-CHI-CF2I to CF3-CI=CF2.

[0320] gas phase process b) Step b) may be carried out in the gas phase.

[0321] Step b) can be carried out in the gas phase, in or without the catalyst.

[0322] Preferably, the deiodide catalyst is selected from the group consisting of oxides, oxyhalides, or halides of metals or metalloids from Group 4 to Group 15 of the periodic table, or oxides, oxyhalides, or halides of metals selected from Li, Na, K, Cs, Mg, Ca, Al, and Sb.

[0323] In particular, the deiodide catalyst is selected from the group consisting of aluminum, iron, or chromium oxides, oxyhalides, or halides. Preferably, the catalyst is chromium oxide, chromium oxyfluoride, or chromium fluoride. Chromium oxyfluoride preferably has a fluorine content of 10% to 50% by weight, preferably 20% to 50% by weight, and particularly 30% to 50% by weight. The fluorine content is measured by ion measurement, by the weight change of the catalyst, or by any other quantitative method known to those skilled in the art. The chromium oxyfluoride or chromium fluoride catalyst is preferably 15m 2 / g to 100m 2 It has a specific surface area of ​​ / g. The chromium oxide catalyst is preferably 100m 2 / g to 300m 2It has a specific surface area of ​​ / g. The specific surface area is measured using a Micromeritics Gemini 2360 instrument with a standard 5-point method (BET method). When the catalyst is chromium oxide, chromium oxyfluoride, or chromium fluoride, it may contain 0.5% to 10% by weight of a co-catalyst relative to the total weight of the catalyst. The co-catalyst is selected from Cr, Ni, Zn, Ti, V, Zr, Mo, Ge, Sn, Pb, and Mg.

[0324] If the catalyst is selected from the group consisting of oxides, oxyhalides, or halides of metals or metalloids from groups 4 to 15 of the periodic table, the catalyst may be activated before use in step b). For example, the catalyst may be activated in the presence of oxygen, air, hydrogen iodide or HF, or a mixture thereof. The catalyst may also be regenerated after the method has been carried out. The regeneration step may include contacting the catalyst with a flow of oxygen or air at a temperature of 200°C to 700°C. The catalyst may also be deactivated over time. Therefore, step b) may be carried out in the presence of oxygen or air or an oxygen-nitrogen mixture. If oxygen is used in step b), the oxygen is present in an amount of 0.005 mol% to 10 mol% relative to the molar amount of fluoroolefin.

[0325] When the metal is selected from Li, Na, K, Cs, Mg, Ca, Al, and Sb, the anion that associates with that metal is F - Cl - , I - or CO3 2- Preferably, the catalyst is NaI, KI, SbF5, AlF3, or SbCl5. The catalyst is preferably 20m 2 / g to 1000m 2 Specific surface area between / g, especially 20m² 2 / g to 300m 2 It has a specific surface area between / g. When the metal of the catalyst is selected from Li, Na, K, Cs, Mg, Ca, Al, and Sb, the catalyst content is 1% to 30% by weight relative to the fluoroolefin.

[0326] The catalyst may be deposited on a porous support. The porous support may be selected from activated carbon, graphite, alumina, and alumina fluoride.

[0327] According to a preferred embodiment, step b) is carried out in the gas phase, in or without the catalyst, at a pressure of 1 bar to 20 bar (absolute pressure), preferably 3 bar to 15 bar (absolute pressure).

[0328] According to a preferred embodiment, step b) is carried out in the gas phase, in or without the catalyst, at a temperature of 150°C to 700°C, preferably 250°C to 600°C.

[0329] According to a preferred embodiment, flow B also includes HI. Therefore, the method includes a step of separating the iodofluoroolefin from HI.

[0330] Step b) in the non-aqueous liquid phase Step b) can be carried out in a non-aqueous liquid phase, with or without the catalyst. Preferably, step b) is carried out in a non-aqueous liquid phase, in the presence of solvent S2. Preferably, solvent S2 is anhydrous. The term “anhydrous” here means solvent S2 containing less than 500 ppm of water, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, more precisely less than 10 ppm, preferably less than 5 ppm, and preferentially, solvent S2 does not contain water. Solvent S2 has a boiling point from 0°C to 250°C, preferably from 20°C to 250°C, particularly from 20°C to 200°C. The solvent S2 is selected from the group consisting of acetic acid, CCl4, chloroform, dichloromethane, sulfolane, tetramethylene sulfone, N,N-dimethylformamide, dimethyl sulfoxide, N,N-dimethylacetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone, and mixtures thereof.

[0331] Preferably, step b) is carried out in a non-aqueous liquid phase in the presence of a catalyst selected from alkali metal salts or alkaline earth metal salts. Preferably, the catalyst is an alkali metal salt. Any alkali metal iodide may be used, but preferably sodium iodide or potassium iodide is used. The ratio of the catalyst to the fluoroolefin is between 1 and 20, preferably between 1 and 10. The catalyst is preferably 20 ml 2 / g to 1000m 2 Specific surface area between / g, especially 20m² 2 / g to 300m 2 It has a specific surface area between / g. The catalyst may be deposited on a porous support. The porous support may be selected from activated carbon, graphite, alumina, and alumina fluoride.

[0332] When step b) is carried out in a non-aqueous liquid phase, the temperature is 50°C to 280°C, preferably 50°C to 250°C.

[0333] According to a preferred embodiment, flow B also includes HI. Therefore, the method includes a step of separating the iodofluoroolefin from HI.

[0334] Aqueous phase step b) Step b) may be carried out using a basic aqueous mixture. The basic aqueous mixture is a liquid (e.g., a solution, dispersion, emulsion, or suspension) having a pH of at least 7, preferably at least 8, and more preferably at least 10. A pH of 10 or higher is favorable for the deiodide reaction. The basic aqueous mixture contains a base selected from the group consisting of hydroxides, oxides, carbonates, or phosphates of alkali metals or alkaline earth metals. Preferably, the base is selected from lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate, sodium phosphate, potassium phosphate, or mixtures thereof. In particular, the base is selected from the group consisting of hydroxides of alkali metals or alkaline earth metals and mixtures thereof. More specifically, the base is selected from the group consisting of sodium hydroxide, potassium hydroxide, or calcium hydroxide and mixtures thereof.

[0335] Advantageously, the basic aqueous mixture contains the base in an amount of 20% to 80% by weight, preferably 30% to 75% by weight, relative to the total weight of the mixture, regardless of the base.

[0336] In this embodiment, step b) is carried out at a temperature of 25°C to 250°C, preferably 25°C to 150°C, and more preferably 25°C to 100°C.

[0337] In this particular embodiment, step b) may be carried out in the presence of a non-aqueous, non-alcoholic solvent in addition to the basic aqueous mixture. A phase transfer catalyst may also be used. The non-aqueous and non-alcoholic solvents are selected from the group consisting of acetonitrile, propionitrile, butyronitrile, methylglutalonitrile, adiponitrile, benzonitrile, ethylene carbonate, propylene carbonate, methyl ethyl ketone, methyl isoamyl ketone, diisobutyl ketone, anisole, 2-methyltetrahydrofuran, tetrahydrofuran, dioxane, diglyme, triglyceride, tetraglyceride, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidinone, sulfolane, dimethyl sulfoxide, perfluoro-N-methylmorpholine, perfluorotetrahydrofuran, and mixtures thereof. Preferably, the non-aqueous and non-alcoholic solvents are selected from acetonitrile, adiponitrile, 2-methyltetrahydrofuran, tetrahydrofuran, dioxane, diglyme, and tetraglyceride.

[0338] A phase transfer catalyst is a substance that facilitates the transfer of ionic compounds from the aqueous phase to the organic phase. The phase transfer catalyst is preferably selected from the group consisting of crown ethers, onium salts, cryptands, polyalkylene glycol ethers, and mixtures thereof. The amount of the phase transfer catalyst is 0.001 mol% to 10 mol%, advantageously 0.01 mol% to 5 mol%, and preferably 0.05 mol% to 5 mol%, relative to the amount of base in the liquid phase.

[0339] Crown ethers are cyclic molecules in which ether groups are linked via dimethylene groups, and the above compounds form molecular structures capable of capturing alkali metal ions. Crown ethers include 18-crown-6 for use with KOH-containing basic aqueous mixtures, 15-crown-5 for use with NaOH-containing basic aqueous mixtures, and 12-crown-4 for use with LiOH-containing basic aqueous mixtures. Onium salts include those of formula R a R b R c Rd P (+) X - or R a R b R c R d N (+) X - This includes quaternary phosphonium salts and quaternary ammonium salts, where R a , R b , R c and R d Independently, C1-C 40 Alkyl, C6-C 40 Aryl or C6-C 40 The aralkyl group is selected, and X is selected from the group consisting of F, Cl, Br, I, OH, CO3, HCO3, SO4, HSO4, H2PO4, HPO4, and PO4. For example, onium salts include tetramethylammonium chloride, tetramethylammonium bromide, benzyltriethylammonium chloride, methyltrioctylammonium chloride, tetra-n-butylammonium chloride, tetra-n-butylammonium bromide, tetra-n-butylphosphonium chloride, tetraphenylphosphonium bromide, tetraphenylphosphonium chloride, triphenylmethylphosphonium bromide, and triphenylmethylphosphonium chloride. Polyalkylene glycol ethers include those with formula R f O(R e O) t R g The compound contains, in the formula, R e This is an alkylene group containing two or more carbon atoms, and each R f and R gt is independently H, alkyl, aryl, or aralkyl, and t is an integer greater than 2. Polyalkylene glycol ethers include, for example, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, hexaethylene glycol, diisopropylene glycol, dipropylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, tetramethylene glycol ether, and their monoalkyl ethers, their dialkyl ethers, and polyalkylene glycols such as polyethylene glycol dimethyl ether and polyethylene glycol dibutyl ether. Among cryptands, 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo-(8.8.8)hexacosan(cryptand) TM 222 and Cryptofix TM 222) is one example.

[0340] According to a preferred embodiment, an iodide salt is formed depending on the base used. This salt may be, for example, KI, CaI2, or NaI.

[0341] According to a preferred embodiment, step b) is carried out at a pressure of 1 bar to 20 bar (absolute pressure), preferably 3 bar to 15 bar (absolute pressure).

[0342] Step c) of this method Preferably, the method includes step c) purifying the stream B obtained in step b) to form stream B1 containing the iodofluoroolefin and stream B2 containing impurities, by-products, or unreacted starting materials. Preferably, after this purification step, the iodofluoroolefin content in stream B1 is more than 90%, advantageously more than 92%, preferably more than 94%, more preferably more than 96%, particularly more than 98%, and more precisely more than 99%. Stream B is preferably purified by distillation, azeotropic distillation, pressurized distillation, extractive distillation, cold separation, absorption into a solvent, or a combination thereof. Stream B may also be separated or purified by contact with an adsorbent. The adsorbent can be a molecular sieve or zeolite having pore openings with an average diameter between 3 angstroms and 11 angstroms, advantageously between 4 angstroms and 10 angstroms, preferably between 5 angstroms and 10 angstroms.

[0343] This method can be carried out continuously, in batches, or in semi-batches. Steps a) and b) may be carried out in two different reactors or in one reactor. If multiple reactors are used, they should be arranged in series.

[0344] To avoid corrosion problems, the reactor used for steps a) and b) is preferably made of a material consisting of a base layer made of material M1 and an inner layer made of material M2.

[0345] Advantageously, material M2 contains at least 40% by weight of nickel relative to the total weight of material M2. Preferably, material M2 contains at least 45% by weight of nickel, more preferably at least 50% by weight of nickel, particularly at least 55% by weight of nickel, especially at least 60% by weight of nickel, preferably at least 65% by weight of nickel, and more preferably at least 70% by weight of nickel relative to the total weight of material M2.

[0346] Material M2 may also contain chromium in an amount of less than 35% by weight, preferably less than 30% by weight, more preferably less than 20% by weight, more preferably less than 15% by weight, particularly less than 10% by weight, and more precisely less than 5% by weight relative to the total weight of Material M2.

[0347] Material M2 may also contain molybdenum in an amount of less than 35% by weight, preferably less than 30% by weight, more preferably less than 20% by weight, more preferably less than 15% by weight, particularly less than 10% by weight, and more precisely less than 5% by weight relative to the total weight of material M2.

[0348] Preferably, material M2 is Monel®, Hastelloy®, Inconel®, or Incoloy®.

[0349] According to a preferred embodiment, material M1 comprises at least 70% by weight of iron, advantageously at least 75% by weight, preferably at least 80% by weight, more preferably at least 85% by weight, particularly at least 90% by weight, and more precisely at least 95% by weight of iron relative to the total weight of material M1.

[0350] Material M1 may also contain less than 2% by weight, advantageously less than 1.5% by weight, preferably less than 1% by weight, more preferably less than 0.75% by weight, particularly less than 0.5% by weight, more precisely less than 0.2% by weight, and preferably less than 0.1% by weight of carbon relative to the total weight of Material M1. More specifically, Material M1 may contain between 0.01% and 0.2% by weight of carbon relative to the total weight of Material M1.

[0351] Preferably, the base layer and the inner layer are arranged to face each other by molten or low-temperature plating, hot or cold rolling, or pressure welding.

[0352] Examples Example 1 Step a): The apparatus used consisted of a 2.0 L Hastelloy C276 autoclave equipped with a pressure indicator, thermal probe, rupture disc, and magnetic bar stirrer. The following were continuously introduced into the autoclave: 140.0 g (0.55 mol) of iodine, 750.0 g of anhydrous ethanol, and 60.0 g (0.52 mol) of CF3-CF=CH2 (HFO-1234yf). The reactor was heated at 85°C for 11 hours, then cooled to room temperature. After degassing, it was flushed with helium, the autoclave was opened, and the reaction mixture was recovered. The organic phase was washed and dried, and then analyzed by gas chromatography (area percentage method). The analysis confirmed the formation of the diiodofluoroalkane compound CF3-CFI-CH2I (selectivity 96.1% and conversion rate 95.3%).

[0353] Step b): A reactor consisting of an Inconel 600 tube with an inner diameter of 28 mm and a length of 640 mm, placed vertically inside a tubular furnace, is used. The catalyst bed consists of a lower 40 mm corundum layer followed by an 85 mm chromium oxyfluoride catalyst layer containing 15% to 20% by weight of pre-activated fluorine. A gas stream and a nitrogen gas stream (volume ratio 1 / 2) consisting of the washed and dried organic phase obtained from step a) are passed over this catalyst at a temperature of 300°C. The gas is washed at the outlet of the reactor and then dried and condensed in a cold trap. A sample is taken and analyzed by gas chromatography (area percentage method). The yield of CF3-CF=CHI, expressed as the ratio of the number of moles of detected CF3-CF=CHI to the number of moles of HFO-1234yf initially introduced, was 83.8%.

[0354] Example 2 Example 1 was repeated using intermediate purification of the diiodofluoroalkane compound by distillation to completely remove excess iodine and impurities. The yield of CF3-CF=CHI after two reaction steps was approximately 78.7%.

[0355] Invention V Summary of Invention V According to a first aspect, the present invention relates to a method for producing an iodofluoroalkane compound, comprising the following steps: a) Contacting an olefin with iodine (I2) in the liquid phase to form a diiodoalkane compound; process b) A step of fluorinating the diiodoalkane compound with hydrogen fluoride to form a flow B containing the iodofluoroalkane compound.

[0356] In a preferred embodiment, the diiodoalkane compound is dried before use in step b).

[0357] According to a preferred embodiment, the diiodoalkane compound is purified before use in step b).

[0358] According to a preferred embodiment, flow B also contains unreacted hydrogen fluoride, and flow B is separated to form flow B1 containing the iodofluoroalkane compound and flow B2 containing the unreacted hydrogen fluoride.

[0359] According to a preferred embodiment, flow B2 is recirculated to process b).

[0360] According to a preferred embodiment, the olefin is a fluoroolefin.

[0361] According to a preferred embodiment, the olefin is of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 )[where R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, Cl, I, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 [A fluoroolefin is provided that at least one of them is F or a group as described above containing at least one fluorine atom.]

[0362] According to another preferred embodiment, the olefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 )[where R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 The fluoroolefin is provided that at least one of the elements is either F or a perfluoro group as described above.

[0363] According to another preferred embodiment, the olefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 )[where R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 It is a fluoroolefin [provided that at least one of them is F].

[0364] According to a preferred embodiment, the diiodoalkane compound obtained in step a) is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, Cl, I, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing at least one fluorine atom.

[0365] According to a preferred embodiment, the diiodoalkane compound obtained in step a) is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0366] According to a preferred embodiment, the diiodoalkane compound is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0367] According to a preferred embodiment, the iodofluoroalkane compound obtained in step b) is of formula (II)(R 1)(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, Cl, I, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing at least one fluorine atom.

[0368] According to a preferred embodiment, the iodofluoroalkane compound obtained in step b) is of formula (II)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4At least one of them is either F or a perfluoro group as described above.

[0369] According to a preferred embodiment, the iodofluoroalkane compound obtained in step b) is of formula (II)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0370] According to a preferred embodiment, the fluoroolefin is CHF=CH2, CF2=CH2, CHF=CHF, CF2=CHF, CF2=CF2, CH3-CF=CH2, CH3-CH=CHF, CH2F-CH=CH2, CH3-CF=CHF, CH2F-CF=CH2, CH3-CH=CF2, CH2F-CH=CHF, CHF2-CH=CH2, CH3-CF=CF2, CH2F-CF=CHF, CHF2-CF=CH2, CH2F-CH=CF2, CHF2-CH=CHF, CF Selected from the group consisting of 3-CH=CH2, CH2F-CF=CF2, CHF2-CF=CHF, CF3-CF=CH2, CHF2-CH=CF2, CF3-CH=CHF, CHF2-CF=CF2, CF3-CF=CHF, CF3-CH=CF2, CF3-CF=CF2, and selected from the group consisting of Tivoli, CF2=CH2, CF2=CHF, CF2=CF2, CF3-CH=CH2, CF3-CF=CH2, CF3-CH=CHF, CF3-CF=CHF, CF3-CF=CF2.

[0371] According to a preferred embodiment, the diiodoalkane compound is CHFI-CH2I, CF2I-CH2I, CHFI-CHFI, CF2I-CHFI, CF2I-CF2I, CH3-CFI-CH2I, CH3-CHI-CHFI, CH2F-CHI-CH2I, CH3-CFI-CHFI, CH2F-CFI-CH2I, CH3-CHI-CF2I, CH2F-CHI-CHFI, CHF2-CHI-CH2I, CH3-CFI-CF2I, CH2F-CFI-CHFI, CHF2-CFI-CH2I, CH2F-CHI-CF2I, CHF2-CHI-CHFI, C Selected from the group consisting of F3-CHI-CH2I, CH2F-CFI-CF2I, CHF2-CFI-CHFI, CF3-CFI-CH2I, CHF2-CHI-CF2I, CF3-CHI-CHFI, CHF2-CFI-CF2I, CF3-CFI-CHFI, CF3-CHI-CF2I, and CF3-CFI-CF2I; preferably selected from the group consisting of CF2I-CH2I, CF2I-CHFI, CF2I-CF2I, CF3-CHI-CH2I, CF3-CFI-CH2I, CF3-CHI-CHFI, CF3-CFI-CHFI, and CF3-CFI-CF2I.

[0372] According to a preferred embodiment, the iodofluoroalkane compound is CHF2-CH2I, CHFI-CH2F, CF3-CH2I, CF2I-CH2F, CHF2-CHFI, CF3-CHFI, CF2I-CHF2, CF3-CF2I, CH3-CF2-CH2I, CH3-CFI-CH2F, CH3-CHF-CHFI, CH3-CHI-CHF2, CH2F-CHF-CH2I, CH2F-CHI-CH2F, CH3-CF2-CHFI, CH3-CFI-CHF2, CH2F-CF2-CH2I, CH2F-CFI-CH2F, CH3-CHF-CF2I, CH3-CHI-CF3, CH2F-CHF-CHFI, CH2F-CHI-CHF2, CHF2-CHF-CH2I, CH3-CF2-CF2I, CH3- CFI-CF3, CH2F-CF2-CHFI, CH2F-CFI-CHF2, CHF2-CF2-CH2I, CH2F-CHF-CF2I, CHF2-CHF-CHFI, CHF 2-CHI-CHF2, CF3-CHF-CH2I, CF3-CHI-CH2F, CH2F-CF2-CF2I, CHF2-CF2-CHFI, CHF2-CFI-CHF2, CF3 -CF2-CH2I, CF3-CFI-CH2F, CHF2-CHF-CF2I, CF3-CHF-CHFI, CF3-CHI-CHF2, CHF2-CF2-CF2I, CF3-C selected from the group consisting of F2-CHFI, CF3-CFI-CHF2, CF3-CHF-CF2I, CF3-CHI-CF3, CF3-CF2-CF2I, CF3-CFI-CF3;Advantageously, the iodofluoroalkane compounds include CHF2-CH2I, CF2I-CH2F, CF3-CH2I, CHF2-CHFI, CF2I-CHF2, CF3-CHFI, CF3-CF2I, CH3-CF2-CH2I, CH3-CHI-CHF2, CH2F-CHI-CH2F, CH3-CF2-CHFI, CH2F-CF2-CH2I, CH3-CHI-CF3, CH2F-CHI-CHF2, CHF2-CHI-CH2F, CH3-CFI-CF3, CH2F-CF2-CHFI, CHF2-CF2-CH2I, CH2F-CHI-CF3, CHF2-CHI-CHF2, CF3-CHI-CH2F, C The iodofluoroalkane compound is selected from the group consisting of H2F-CFI-CF3, CHF2-CF2-CHFI, CF3-CFI-CH2F, CF3-CF2-CH2I, CHF2-CHI-CF3, CF3-CHI-CHF2, CHF2-CFI-CF3, CF3-CFI-CHF2, CF3-CF2-CHFI, CF3-CHI-CF3, and CF3-CFI-CF3; preferably, the iodofluoroalkane compound is selected from the group consisting of CF3-CH2I, CF3-CHFI, CF3-CF2I, CF3-CHI-CH2F, CF3-CF2-CH2I, CF3-CHI-CHF2, CF3-CF2-CHFI, and CF3-CFI-CF3.

[0373] According to a preferred embodiment, the method includes: - In step a), convert CF2=CH2 to CF2I-CH2I, and in step b), fluorinate CF2I-CH2I to CF3-CH2I; or - In step a), convert CF2=CHF to CF2I-CHFI, and in step b), fluorinate CF2I-CHFI to v; or - In step a), convert CF2=CF2 to CF2I-CF2I, and in step b), fluorinate CF2I-CF2I to CF3-CF2I; or - In step a), convert CF3-CH=CH2 to CF3-CHI-CH2I, and in step b), fluorinate CF3-CHI-CH2I to CF3-CHI-CH2F; or - In step a), convert CF3-CF=CH2 to CF3-CFI-CH2I, and in step b), fluorinate CF3-CFI-CH2I to CF3-CF2-CH2I; or - In step a), convert CF3-CH=CHF to CF3-CHI-CHFI, and in step b), fluorinate CF3-CHI-CHFI to CF3-CHI-CHF2; or - In step a), convert CF3-CF=CHF to CF3-CFI-CHFI, and in step b), fluorinate CF3-CFI-CHFI to CF3-CF2-CHFI; or - Step a) converts CF3-CF=CF2 to CF3-CFI-CF2I, and step b) fluorinates CF3-CFI-CF2I to CF3-CFI-CF3.

[0374] According to a preferred embodiment, step b) is carried out in the gas phase at a temperature of 150°C to 700°C, preferably 250°C to 600°C.

[0375] According to a preferred embodiment, step b) is carried out in the presence of a catalyst selected from the group consisting of oxides, oxyhalides, or halides of metals or metalloids from groups 4 to 15 of the periodic table.

[0376] According to a preferred embodiment, step b) is carried out in the gas phase at a temperature of -50°C to 250°C in the presence of a catalyst.

[0377] According to a preferred embodiment, step b) is carried out in the gas phase at a temperature of 20°C to 300°C in the absence of a catalyst.

[0378] According to a preferred embodiment, step a) is carried out in the liquid phase in the presence of a solvent S1 selected from the group consisting of aqueous potassium iodide, ethers, fluorinated ethers, alcohols, fluorinated alcohols, esters, aromatic solvents, fluorinated aromatic solvents, halogenated solvents, and mixtures thereof.

[0379] Detailed description of Invention V According to a first aspect, the present invention relates to a method for producing an iodofluoroalkane compound. Preferably, the method includes a step of contacting an olefin with iodine (I2) in a liquid phase to form a diiodoalkane compound. Preferably, the method also includes a step of fluorinating the diiodoalkane compound obtained in step a) with hydrogen fluoride to form a flow B containing the iodofluoroalkane compound.

[0380] Step a) of this method Step a) of this method requires contacting the olefin with iodine in the liquid phase.

[0381] For example, the olefin is of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) is of R 1 , R 2 , R 3 and R 4 These are H, F, Cl, I, and C1-C, which are independent of each other. 10 Alkyl, C3-C 10 Cycloalkyl groups, C2-C 10 Alkenyl group, C3-C 10 Cycloalkenyl group, and C6-C 10 Selected from the group consisting of aryl groups.

[0382] Preferably, the olefin is a fluoroolefin.

[0383] In particular, the olefin is of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) is a fluoroolefin, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, Cl, I, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that; substituent R 1 , R 2 , R 3 or R 4 The condition is that at least one of them is F or is a group as described above containing at least one fluorine atom.

[0384] The olefin is preferably of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) is a fluoroolefin, in which R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing at least one fluorine atom.

[0385] The term "alkyl" refers to a monovalent group derived from linear or branched alkanes containing a specific number of carbon atoms. The term "cycloalkyl" refers to a monovalent group derived from cycloalkanes containing a specific number of carbon atoms. The term "alkenyl" refers to a monovalent group containing a specific number of carbon atoms and at least one carbon-carbon double bond. The term "cycloalkenyl" refers to a monovalent group derived from cycloalkenes containing a specific number of carbon atoms and at least one carbon-carbon double bond in the cyclic portion. The term "aryl" refers to a monovalent group derived from arenes containing a specific number of carbon atoms.

[0386] Preferably, the alkyl, cycloalkyl, alkenyl, cycloalkenyl, or aryl group is not substituted with a functional group other than fluorine. Nevertheless, the group may contain several fluorine atoms on its carbon chain, for example, 1 to 10 fluorine atoms, preferably 1 to 5 fluorine atoms.

[0387] Preferably, the olefin is of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) is a fluoroolefin, in which R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, I, and 1 to 10 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0388] Preferably, the olefin is of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) is a fluoroolefin, in which R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, and 1 to 10 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0389] Preferably, the olefin is of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) is a fluoroolefin, in which R 1 , R 2 , R 3 and R 4 The C1-C atoms may be independently substituted with H, F, I, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0390] Preferably, the olefin is of formula (I)(R 1 )(R 2 )C=C(R 3 )(R 4 ) is a fluoroolefin, in which R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0391] Preferably, the olefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is a fluoroolefin, in which R 1 , R 2 , R 3and R 4 These are H, F, I, C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0392] Preferably, the olefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is a fluoroolefin, in which R 1 , R 2 , R 3 and R 4 These are H, F, and C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0393] Preferably, the olefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is a fluoroolefin, in which R 1 , R 2 , R 3 and R 4These are H, F, I, C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0394] Preferably, the olefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is a fluoroolefin, in which R 1 , R 2 , R 3 and R 4 These are H, F, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0395] Alternatively, the olefin is formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is a fluoroolefin, in which R 1 , R 2 , R 3 and R 4 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F, where n is an integer from 1 to 10. 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0396] Preferably, the olefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is a fluoroolefin, in which R 1 , R 2 , R 3 and R 4 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F (where n is an integer from 1 to 5), however, the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0397] Preferably, the olefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is a fluoroolefin, in which R 1 , R 2 , R3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 10, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0398] Preferably, the olefin is of formula (I)(R 1) (R 2 )C=C(R 3 )(R 4 ) is a fluoroolefin, in which R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0399] mM, the olefin is CHF=CH2, CF2=CH2, CHF=CHF, CF2=CHF, CF2=CF2, CH3-CF=CH2, CH3-CH=CHF, CH2F-CH=CH2, CH3-CF=CHF, CH2F-CF=CH2, CH3-CH=CF2, CH2F-CH=CHF, CHF2-CH=CH2, CH3-CF=CF2, CH2F-CF=CHF, CHF2-CF=CH2, CH2F-CH=CF2, CHF2-CH=CHF, CF3-CH=CH2, CH2F-C Full olefins selected from the group consisting of F=CF2, CHF2-CF=CHF, CF3-CF=CH2, CHF2-CH=CF2, CF3-CH=CHF, CHF2-CF=CF2, CF3-CF=CHF, CF3-CH=CF2, CF3-CF=CF2; in particular, full olefins selected from the group consisting of CF2=CH2, CF2=CHF, CF2=CF2, CF3-CH=CH2, CF3-CF=CH2, CF3-CH=CHF, CF3-CF=CHF, CF3-CF=CF2.

[0400] The olefin, in particular the fluoroolefin described above, may have a boiling point below 100°C at atmospheric pressure. Advantageously, the olefin, in particular the fluoroolefin described above, may have a boiling point below 75°C at atmospheric pressure. Preferably, the olefin, in particular the fluoroolefin described above, may have a boiling point below 50°C at atmospheric pressure. More preferably, the olefin, in particular the fluoroolefin described above, may have a boiling point below 25°C at atmospheric pressure. In particular, the olefin, in particular the fluoroolefin described above, may have a boiling point below 10°C at atmospheric pressure.

[0401] According to a preferred embodiment, step a) can be carried out in the presence of a mixture of olefins or a mixture of fluoroolefins described above to bring about the co-production of an iodofluoroalkane compound via the corresponding diiodoalkane compound according to the present method.

[0402] Step a) enables the generation of a diiodoalkane compound. Preferably, the diiodoalkane compound obtained in step a) is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ).

[0403] The diiodoalkane compound obtained in step a) is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 ) may be a compound of the same type, where R 1 , R 2 , R 3 and R 4 These are H, F, Cl, I, and C1-C, which are independent of each other. 10 Alkyl, C3-C 10 Cycloalkyl groups, C2-C 10 Alkenyl group, C3-C 10 Cycloalkenyl group, and C6-C 10 Selected from the group consisting of aryl groups.

[0404] Advantageously, the diiodoalkane compound obtained in step a) is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, Cl, I, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing at least one fluorine atom.

[0405] Preferably, the diiodoalkane compound is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing at least one fluorine atom.

[0406] Preferably, the diiodoalkane compound is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, I, and 1 to 10 fluorine atoms. 10Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0407] Preferably, the diiodoalkane compound is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, and 1 to 10 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0408] Preferably, the diiodoalkane compound is of formula (II)(R1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 The C1-C atoms may be independently substituted with H, F, I, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0409] Preferably, the diiodoalkane compound is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0410] Preferably, the diiodoalkane compound is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0411] Preferably, the diiodoalkane compound is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, and C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C 10 Perfluorocycloalkenyl group, C6-C 10Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0412] Preferably, the diiodoalkane compound is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0413] Preferably, the diiodoalkane compound is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0414] Alternatively, the diiodoalkane compound can be expressed using formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F, where n is an integer from 1 to 10. 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0415] Preferably, the diiodoalkane compound is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F (where n is an integer from 1 to 5), however, the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0416] Preferably, the diiodoalkane compound is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and for each n unit from the group consisting of H and F, where n is an integer from 1 to 10, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0417] Preferably, the diiodoalkane compound is of formula (II)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and for each n unit from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0418] In particular, the diiodoalkane compounds include CHFI-CH2I, CF2I-CH2I, CHFI-CHFI, CF2I-CHFI, CF2I-CF2I, CH3-CFI-CH2I, CH3-CHI-CHFI, CH2F-CHI-CH2I, CH3-CFI-CHFI, CH2F- CFI-CH2I, CH3-CHI-CF2I, CH2F-CHI-CHFI, CHF2-CHI-CH2I, CH3-CFI-CF2I, CH2F-CFI-CHFI, CHF2-CFI-CH2I, CH2F-CHI-CF2I, CHF2-CHI-CHFI, CF3-CHI -Selected from the group consisting of CH2I, CH2F-CFI-CF2I, CHF2-CFI-CHFI, CF3-CFI-CH2I, CHF2-CHI-CF2I, CF3-CHI-CHFI, CHF2-CFI-CF2I, CF3-CFI-CHFI, CF3-CHI-CF2I, CF3-CFI-CF2I; more specifically, selected from the group consisting of CF2I-CH2I, CF2I-CHFI, CF2I-CF2I, CF3-CHI-CH2I, CF3-CFI-CH2I, CF3-CHI-CHFI, CF3-CFI-CHFI, CF3-CFI-CF2I.

[0419] More specifically, step a) of this method includes: - Converting CF2=CH2 to CF2I-CH2I; or - Converting CF2=CHF to CF2I-CHFI; or - Converting CF2=CF2 to CF2I-CH2I; or - Converting CF3-CH=CH2 to CF3-CHI-CH2I; or - Converting CF3-CF=CH2 to CF3-CFI-CH2I or - Converting CF3-CH=CHF to CF3-CHI-CHFI; or - Converting CF3-CF=CHF to CF3-CFI-CHFI; or - Convert CF3-CF=CF2 to CF3-CFI-CF2I.

[0420] As described above, step a) can use a mixture of olefins selected from the group consisting of, for example, CF2=CH2, CF2=CHF, CF2=CF2, CF3-CH=CH2, CF3-CF=CH2, CF3-CH=CHF, CF3-CF=CHF, and CF3-CF=CF2 to obtain flow A containing a mixture of diiodoalkane compounds selected from the group consisting of, for example, CF2I-CH2I, CF2I-CHFI, CF2I-CF2I, CF3-CHI-CH2I, CF3-CFI-CH2I, CF3-CHI-CHFI, CF3-CFI-CHFI, and CF3-CFI-CF2I.

[0421] Preferably, step a) may be carried out in the liquid phase. Preferably, step a) is carried out in the absence of a catalyst. Preferably, step a) is carried out in the presence of solvent S1. Preferably, solvent S1 is selected from the group consisting of aqueous potassium iodide, ethers, fluorinated ethers, alcohols, fluorinated alcohols, esters, aromatic solvents, fluorinated aromatic solvents, halogenated solvents, and mixtures thereof. Advantageously, solvent S1 is selected from the group consisting of aqueous potassium iodide, ethyl and methyl ethers, hydrofluoroethers, ethyl and methyl alcohols, ethyl lactate, toluene, xylene, para-chlorotrifluoromethylbenzene, hexafluorobenzene, tetrachloromethane, chloroform, dichloromethane, 1-bromopropane, and mixtures thereof. The use of a solvent in this method makes it possible to avoid clogging problems associated with iodine sublimation and to limit the formation of impurities (reaction by-products, polymers derived from olefins, etc.), which makes it possible to achieve a selectivity that is particularly advantageous from an industrial standpoint.

[0422] Preferably, iodine is brought into contact with the olefin, and in particular with the fluoroolefin described above, in a stoichiometric or greater amount. For example, the molar ratio of I2 / olefin is 0.1 to 50, preferably 0.5 to 25, and particularly 1 to 20.

[0423] Preferably, the oxygen content dissolved in solvent S1 is less than 3000 ppm, advantageously less than 2000 ppm, preferably less than 1000 ppm, more preferably less than 500 ppm, particularly less than 250 ppm, more specifically less than 100 ppm, preferably less than 50 ppm, and preferentially less than 10 ppm. This avoids decomposition of the starting material and the desired product. Solvent S1 preferably has a boiling point of 0°C to 250°C, preferably 20°C to 250°C, and particularly 20°C to 200°C.

[0424] The temperature at which step a) is carried out is 20°C to 280°C, preferably 30°C to 250°C. Step a) can be carried out at a pressure of 0.1 bar to 15 bar, preferably 1 bara to 10 bara (absolute pressure).

[0425] The diiodoalkane compound may be dried before use in step b). This removes any trace amounts of water that may be present. This drying can be carried out by contact with an adsorbent, absorbent, a 3-angstrom to 5-angstrom sieve, or zeolite. The dried diiodoalkane compound may be purified or used as is in step b).

[0426] The diiodoalkane compound may be purified before use in step b). This purification may be performed before or after the drying step. This allows for the removal of certain impurities that are difficult to separate from the iodofluoroalkane compound. This step also allows for an increase in the selectivity of step b). Purification can be carried out by distillation, azeotropic distillation, pressurized distillation, extractive distillation, cold separation, absorption into a solvent, contact with an adsorbent, or a combination thereof. Advantageously, the purification of the diiodoalkane compound is performed to produce a stream A in which the diiodoalkane compound content is greater than 90%, preferably greater than 92%, preferably greater than 94%, more preferably greater than 96%, particularly greater than 98%, and more precisely greater than 99%. This stream A is then used in step b).

[0427] When step a) is carried out using a mixture of olefins, purification will yield a mixture of diiodoalkane compounds or a specific diiodoalkane compound, depending on the conditions used for purification.

[0428] Alternatively, the dried diiodoalkane compound may be used directly in step b) without being purified after the drying step. This can be done, for example, when step a) is carried out with a high conversion rate and selectivity of over 90%, preferably over 95%. Since the purification step can incur considerable costs, the absence of purification between step a) and step b) is advantageous from the viewpoint of the overall productivity of this method.

[0429] The diiodoalkane compound used in step b) is preferably anhydrous, i.e., the stream containing the diiodoalkane compound used in step b) is anhydrous. The term “anhydrous” here means that the water content in the stream containing the diiodoalkane compound used in step b) is less than 500 ppm by mass, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, more precisely less than 10 ppm, more preferably less than 5 ppm, and preferentially, the diiodoalkane compound or the stream containing it for carrying out step b) is water-free.

[0430] Step b) of this method Step b) of this method is a step of fluorinating the diiodoalkane compound with hydrogen fluoride to form a flow B containing the iodofluoroalkane compound. The diiodoalkane compound is as described above in step a) of this method. Advantageously, the diiodoalkane compound obtained in step b) is of formula (III)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, Cl, I, and C1-C, which are independent of each other. 10 Alkyl, C3-C 10 Cycloalkyl groups, C2-C 10 Alkenyl group, C3-C 10 Cycloalkenyl group, and C6-C 10Selected from the group consisting of aryl groups.

[0431] Therefore, the iodofluoroalkane compound is preferably of formula (III)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, Cl, I, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10 The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing at least one fluorine atom.

[0432] Preferably, the iodofluoroalkane compound is of formula (III)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, and at least one fluorine atom. 10 Alkyl groups, which may be substituted with at least one fluorine atom, C3-C 10 Cycloalkyl groups, which may be substituted with at least one fluorine atom, C2-C 10The alkenyl group may be substituted with at least one fluorine atom (C3-C). 10 A cycloalkenyl group and a C6-C which may be substituted with at least one fluorine atom. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing at least one fluorine atom.

[0433] Preferably, the iodofluoroalkane compound is of formula (III)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, I, and 1 to 10 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0434] Preferably, the iodofluoroalkane compound is of formula (III)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1, R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, and 1 to 10 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 10 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 10 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 10 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 10 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 10 fluorine atoms.

[0435] Preferably, the iodofluoroalkane compound is of formula (III)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 The C1-C atoms may be independently substituted with H, F, I, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0436] Preferably, the iodofluoroalkane compound is of formula (III)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are C1-C atoms that may be independently substituted with H, F, and 1 to 5 fluorine atoms. 10 Alkyl groups, C3-C which may be substituted with 1 to 5 fluorine atoms. 10 Cycloalkyl groups, C2-C which may be substituted with 1 to 5 fluorine atoms. 10 Alkenyl group, C3-C which may be substituted with 1 to 5 fluorine atoms 10 A cycloalkenyl group and a C6-C group which may be substituted with 1 to 5 fluorine atoms. 10 Selected from the group consisting of aryl groups, provided that the substituent R 1 , R 2 , R 3 or R 4 At least one of them is F or a group as described above containing 1 to 5 fluorine atoms.

[0437] Preferably, the iodofluoroalkane compound is of formula (III)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C 10 Perfluorocycloalkenyl group, C6-C10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0438] Preferably, the iodofluoroalkane compound is of formula (III)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, and C1-C, which are independent of each other. 10 Perfluoroalkyl groups, C3-C 10 Perfluorocycloalkyl groups, C2-C 10 Perfluoroalkenyl group, C3-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0439] Preferably, the iodofluoroalkane compound is of formula (III)(R 1 )(R 2 )CF-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, I, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0440] Preferably, the iodofluoroalkane compound is of formula (III)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, C1-C5 perfluoroalkyl groups, and C5-C 10 Perfluorocycloalkyl group, C2-C5 perfluoroalkenyl group, C5-C 10 Perfluorocycloalkenyl group, C6-C 10 Selected from the group consisting of perfluoroaryl groups, provided that substituent R 1 , R 2 , R 3 or R 4 At least one of them is either F or a perfluoro group as described above.

[0441] Alternatively, the iodofluoroalkane compound can be expressed using formula (III)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F, where n is an integer from 1 to 10. 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0442] Preferably, the iodofluoroalkane compound is of formula (III)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, I, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and independently of each unit n from the group consisting of H, I, and F (where n is an integer from 1 to 5), however, the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0443] Preferably, the iodofluoroalkane compound is of formula (III)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1-[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and for each n unit from the group consisting of H and F, where n is an integer from 1 to 10, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0444] Preferably, the iodofluoroalkane compound is of formula (III)(R 1 )(R 2 )C(I)-C(I)(R 3 )(R 4 It is a compound of ) and in the formula, R 1 , R 2 , R 3 and R 4 These are H, F, or Y, independently of each other. 1 -[-C(Y 2 )(Y 3 )-] n -(In the formula, Y 1 , Y 2 and Y 3 The substituents R are selected independently of each other and for each n unit from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 The condition is that at least one of them is F.

[0445] Preferably, the iodofluoroalkane compound is CHF2-CH2I, CHFI-CH2F, CF3-CH2I, CF2I-CH2F, CHF2-CHFI, CF3-CHFI, CF2I-CHF2, CF3-CF2I, CH3-CF2-CH2I, CH3-CFI-CH2F, CH3-CHF-CHFI, CH3-BL-CHF2, CH2F-CHF-CH2I, CH2F-BL-CH2F, CH3-CF2-CHFI, CH3-CFI-CHF2, CH2F-CF2-CH2I, CH2F-CFI-CH2F, CH3-CHF-CF2I, CH3-BL-CF3, CH2F-CHF-CHFI, CH2F-BL-CHF2, CHF2-CHF-CH2I, CH3-CF2-CF2I, CH3-CFI- CF3, CH2F-CF2-CHFI, CH2F-CFI-CHF2, CHF2-CF2-CH2I, CH2F-CHF-CF2I, CHF2-CHF-CHFI, CHF2-C HI-CHF2, CF3-CHF-CH2I, CF3-CHI-CH2F, CH2F-CF2-CF2I, CHF2-CF2-CHFI, CHF2-CFI-CHF2, CF3-C F2-CH2I, CF3-CFI-CH2F, CHF2-CHF-CF2I, CF3-CHF-CHFI, CF3-CHI-CHF2, CHF2-CF2-CF2I, CF3-CF selected from the group consisting of 2-CHFI, CF3-CFI-CHF2, CF3-CHF-CF2I, CF3-CHI-CF3, CF3-CF2-CF2I, CF3-CFI-CF3;Advantageously, the iodofluoroalkane compounds include CHF2-CH2I, CF2I-CH2F, CF3-CH2I, CHF2-CHFI, CF2I-CHF2, CF3-CHFI, CF3-CF2I, CH3-CF2-CH2I, CH3-CHI-CHF2, CH2F-CHI-CH2F, CH3-CF2-CHFI, CH2F-CF2-CH2I, CH3-CHI-CF3, CH2F-CHI-CHF2, CHF2-CHI-CH2F, CH3-CFI-CF3, CH2F-CF2-CHFI, CHF2-CF2-CH2I, CH2F-CHI-CF3, CHF2-CHI-CHF2, CF3-CHI-CH2F, C The iodofluoroalkane compound is selected from the group consisting of H2F-CFI-CF3, CHF2-CF2-CHFI, CF3-CFI-CH2F, CF3-CF2-CH2I, CHF2-CHI-CF3, CF3-CHI-CHF2, CHF2-CFI-CF3, CF3-CFI-CHF2, CF3-CF2-CHFI, CF3-CHI-CF3, and CF3-CFI-CF3; preferably, the iodofluoroalkane compound is selected from the group consisting of CF3-CH2I, CF3-CHFI, CF3-CF2I, CF3-CHI-CH2F, CF3-CF2-CH2I, CF3-CHI-CHF2, CF3-CF2-CHFI, and CF3-CFI-CF3.

[0446] Therefore, step b) of this method includes: - Fluorinating CF2I-CH2I to CF3-CH2I; or - Fluorinating CF2I-CHFI to CF3-CHFI; or - Fluorinating CF2I-CF2I to CF3-CF2I; or - Fluorinating CF3-CHI-CH2I to CF3-CHI-CH2F; or - Fluorinating CF3-CFI-CH2I to CF3-CF2-CH2I; or - Fluorinating CF3-CHI-CHFI to CF3-CHI-CHF2; or - Fluorinating CF3-CFI-CHFI to CF3-CF2-CHFI; or - Fluorinating CF3-CFI-CF2I to CF3-CFI-CF3.

[0447] If step a) is carried out using a mixture of olefins, step b) is preferably carried out using a mixture of diiodoalkane compounds to form a mixture of iodofluoroalkane compounds.

[0448] The fluorination in step b) involves a reaction between the diiodoalkane compound and hydrofluoric acid. This makes it possible to replace iodine atoms with fluorine atoms.

[0449] Preferably, the hydrofluoric acid (HF) is anhydrous. Here, "anhydrous" refers to hydrofluoric acid containing less than 500 ppm of water, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, more precisely less than 10 ppm, preferably less than 5 ppm, and preferably, the hydrofluoric acid is water-free. The use of anhydrous hydrofluoric acid in this method avoids the formation of impurities. The use of anhydrous hydrofluoric acid allows for the achievement of a particularly advantageous selectivity from an industrial standpoint. Preferably, the hydrofluoric acid is anhydrous and gaseous.

[0450] Preferably, hydrofluoric acid is brought into contact with the diiodoalkane compound in a stoichiometric amount or slightly more. For example, the HF / diiodoalkane compound molar ratio is 1 to 10, preferably 1 to 5. An excess amount of hydrofluoric acid excessively promotes the fluorination of the diiodoalkane compound. Therefore, in the presence of a molar ratio greater than 15, formula (IV)(R 1 )(R 2 )CF-C(F)(R 3 )(R 4 Compound (IV) is formed in large or predominant amounts. Substituent R in compound (IV) 1 , R 2 , R 3 and R 4 The iodofluoroalkane compounds of formula (III) are as described above.

[0451] Step b) can be carried out in either the liquid or gas phase. Step b) can be carried out in either the presence or absence of the catalyst.

[0452] gas phase process b) In the gas phase, step b) is carried out at a temperature of 150°C to 700°C, preferably 250°C to 600°C.

[0453] Regardless of whether step b) is carried out in the gas phase, in the presence or absence of the catalyst, the pressure in this step is 0.1 bar to 30 bar, preferably 1 bar to 20 bar, and particularly 1 bar to 15 bar.

[0454] When step b) is carried out in the gas phase, step b) can be carried out in the presence of a catalyst. Preferably, the catalyst is selected from the group consisting of oxides, oxyhalides, or halides of metals or metalloids from groups 4 to 15 of the periodic table. Preferably, the catalyst is chromium oxide, chromium oxyfluoride, or chromium fluoride. Chromium oxyfluoride preferably has a fluorine content of 10% to 50% by weight, preferably 20% to 50% by weight, and particularly 30% to 50% by weight. The fluorine content is measured by ion measurement, by the weight change of the catalyst, or by any other quantitative method known to those skilled in the art. The chromium oxyfluoride or chromium fluoride catalyst is preferably 15m 2 / g to 100m 2 It has a specific surface area of ​​ / g. The chromium oxide catalyst is preferably 100m 2 / g to 300m 2It has a specific surface area of ​​1 / g. The specific surface area is measured using a Micromeritics Gemini 2360 instrument with a standard 5-point method (BET method). When the catalyst is chromium oxide, chromium oxyfluoride, or chromium fluoride, it may contain 0.5% to 10% by weight of a co-catalyst relative to the total weight of the catalyst. The co-catalyst is selected from Cr, Ni, Zn, Ti, V, Zr, Mo, Ge, Sn, Pb, and Mg. Other examples of catalysts include AlF3, SbCl5, and SbF5. The catalyst may be deposited on a porous support. The porous support may be selected from activated carbon, graphite, alumina, and alumina fluoride.

[0455] The catalyst may be activated before use in step b). For example, the catalyst may be activated in the presence of oxygen, air, HF, or a mixture thereof.

[0456] The catalyst may become inactive over time. Therefore, step b) may be carried out in the presence of oxygen, air, or an oxygen-nitrogen mixture. If oxygen is used in step b), the oxygen is present in an amount of 0.005 mol% to 10 mol% relative to the molar amount of diiodoalkane.

[0457] The catalyst may also be regenerated after the method has been carried out. The regeneration step may include bringing the catalyst into contact with a flow of oxygen or air at a temperature of 200°C to 700°C.

[0458] Alternatively, step b) may be carried out in the gas phase, in the absence of the catalyst.

[0459] Liquid phase process b) In the liquid phase, step b) can be carried out in the presence or absence of a solvent.

[0460] Step b) may be carried out in the liquid phase in the presence of solvent S2. Preferably, solvent S2 is anhydrous. The term “anhydrous” here means solvent S2 containing less than 500 ppm of water, advantageously less than 250 ppm, preferably less than 100 ppm, more preferably less than 50 ppm, particularly less than 25 ppm, more precisely less than 10 ppm, preferably less than 5 ppm, and preferentially, solvent S2 does not contain water. Solvent S2 has a boiling point from 0°C to 250°C, preferably from 20°C to 250°C, particularly from 20°C to 200°C. The solvent S2 is selected from the group consisting of 1,1,1,2,2,3,4,5,5,5-decafluoropentane, 1,1,1,3,3-pentafluorobutane, 1,1,2-trichloro-2,2-difluoroethane, 1,1,2-trichloro-2-fluoroethane, 1,1,2-trichloro-1,2,2-trifluoroethane, nitromethane, nitrobenzene, sulfolane, tetramethylenesulfone, N,N-dimethylformamide, dimethyl sulfoxide, N,N-dimethylacetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone, and mixtures thereof.

[0461] Step b) may be carried out in the liquid phase, in the absence of a solvent. In this case, the temperature and pressure conditions are set so that the diiodoalkane compound and / or hydrofluoric acid are in liquid state. If a catalyst is present, the temperature and pressure conditions can be adjusted to keep the catalyst in liquid state.

[0462] Preferably, in the liquid phase, step b) is carried out in the presence of a catalyst (regardless of the presence or absence of a solvent). The catalyst may be based on one or more metals selected from metals of groups 1 to 15 of the periodic table and mixtures thereof. Catalysts based on Lewis acids, metal halides, particularly halides of antimony, tin, tantalum, or titanium; transition metal halides such as iron, niobium, molybdenum, or cesium; transition metal oxides; halides of group IVB metals; halides of group VB metals; chromium fluoride halides; chromium fluoride oxides; or mixtures thereof can be used. Metal chlorides and fluorides may be advantageously used. Examples of such catalysts include SbCl5, SbCl3, TiCl4, SnCl4, TaCl5, NbCl5, TiCl4, FeCl3, MoCl6, CsCl, KCl, MgCl2, and their corresponding fluorinated derivatives. Pentavalent metal halides are suitable for use.

[0463] Preferably, the flow B formed in step b) is recovered in gaseous form. This is particularly advantageous when step b) is carried out in the liquid phase. Thus, the reaction product is removed from the reactor in gaseous form, while at the same time, all or part of the reaction mixture (solvent, starting material) is maintained in liquid form.

[0464] Step c) of this method As described above, flow B contains an iodofluoroalkane compound. Preferably, flow B also contains unreacted hydrogen fluoride. Flow B also contains hydrogen iodide resulting from the substitution of iodine atoms with fluorine atoms. In particular, flow B is separated to form flow B1 containing the iodofluoroalkane compound and flow B2 containing unreacted hydrogen fluoride and hydrogen iodide (step c).

[0465] Stream B may also contain the compound of formula (IV) and / or an unreacted diiodoalkane compound. After separation, the compound of formula (IV) may be contained in stream B1, stream B2, or both. In this case, streams B1 and B2 can be purified to remove the compound of formula (IV). The unreacted diiodoalkane compound is preferably contained in stream B2.

[0466] The flows B, B1, and B2 are preferably separated and / or purified by distillation, azeotropic distillation, pressurized distillation, extractive distillation, cold separation, absorption into a solvent, or a combination thereof. The flows B, B1, and B2 may also be separated or purified by contact with an adsorbent. The adsorbent can be a molecular sieve or zeolite having pore openings with an average diameter between 3 angstroms and 11 angstroms, preferably between 4 angstroms and 10 angstroms, and more preferably between 5 angstroms and 10 angstroms.

[0467] Preferably, flow B2 is recycled to step b); preferably, flow B2 without compound (IV) is recycled to step b). This recycling step improves the overall yield of the method (better conversion rate), saves expensive reagents (and catalysts), and minimizes the environmental impact. Without this recycling step, unreacted hydrofluoric acid would have to be incinerated, thus increasing the carbon dioxide emissions of the method.

[0468] This method can be carried out continuously, in batches, or in semi-batches. It may be carried out continuously in at least two reactors, or in a single reactor containing at least two reaction zones.

[0469] Therefore, as described above in this patent application, the method is - In step a), convert CF2=CH2 to CF2I-CH2I, and in step b), fluorinate CF2I-CH2I to CF3-CH2I; or - In step a), convert CF2=CHF to CF2I-CHFI, and in step b), fluorinate CF2I-CHFI to v; or - In step a), convert CF2=CF2 to CF2I-CF2I, and in step b), fluorinate CF2I-CF2I to CF3-CF2I; or - In step a), convert CF3-CH=CH2 to CF3-CHI-CH2I, and in step b), fluorinate CF3-CHI-CH2I to CF3-CHI-CH2F; or - In step a), convert CF3-CF=CH2 to CF3-CFI-CH2I, and in step b), fluorinate CF3-CFI-CH2I to CF3-CF2-CH2I; or - In step a), convert CF3-CH=CHF to CF3-CHI-CHFI, and in step b), fluorinate CF3-CHI-CHFI to CF3-CHI-CHF2; or - In step a), convert CF3-CF=CHF to CF3-CFI-CHFI, and in step b), fluorinate CF3-CFI-CHFI to CF3-CF2-CHFI; or - Step a) converts CF3-CF=CF2 to CF3-CFI-CF2I, and step b) fluorinates CF3-CFI-CF2I to CF3-CFI-CF3.

[0470] To avoid corrosion problems, the reactor in which steps a) and b) are carried out is preferably made of a material consisting of a base layer made of material M1 and an inner layer made of material M2.

[0471] Advantageously, material M2 contains at least 40% by weight of nickel relative to the total weight of material M2. Preferably, material M2 contains at least 45% by weight of nickel, more preferably at least 50% by weight of nickel, particularly at least 55% by weight of nickel, especially at least 60% by weight of nickel, preferably at least 65% by weight of nickel, and more preferably at least 70% by weight of nickel relative to the total weight of material M2.

[0472] Material M2 may also contain chromium in an amount of less than 35% by weight, preferably less than 30% by weight, more preferably less than 20% by weight, more preferably less than 15% by weight, particularly less than 10% by weight, and more precisely less than 5% by weight relative to the total weight of Material M2.

[0473] Material M2 may also contain molybdenum in an amount of less than 35% by weight, preferably less than 30% by weight, more preferably less than 20% by weight, more preferably less than 15% by weight, particularly less than 10% by weight, and more precisely less than 5% by weight relative to the total weight of material M2.

[0474] Preferably, material M2 is Monel®, Hastelloy®, Inconel®, or Incoloy®.

[0475] According to a preferred embodiment, material M1 comprises at least 70% by weight of iron, advantageously at least 75% by weight, preferably at least 80% by weight, more preferably at least 85% by weight, particularly at least 90% by weight, and more precisely at least 95% by weight of iron relative to the total weight of material M1.

[0476] Material M1 may also contain less than 2% by weight, advantageously less than 1.5% by weight, preferably less than 1% by weight, more preferably less than 0.75% by weight, particularly less than 0.5% by weight, more precisely less than 0.2% by weight, and preferably less than 0.1% by weight of carbon relative to the total weight of Material M1. More specifically, Material M1 may contain between 0.01% and 0.2% by weight of carbon relative to the total weight of Material M1.

[0477] Preferably, the base layer and the inner layer are arranged to face each other by molten or low-temperature plating, hot or cold rolling, or pressure welding.

[0478] Examples Example 1 - Synthesis of CF3-CFI-CF3 Step a): The apparatus used consisted of a 1.0 L Hastelloy C276 autoclave equipped with a pressure indicator, thermal measuring probe, rupture disc, and magnetic bar agitator.

[0479] The following substances were continuously introduced into the autoclave: 127.0 g (0.5 mol) of iodine, 83.0 g (0.5 mol) of potassium iodide, 180.0 g of water, and 60.0 g (0.4 mol) of hexafluoropropene (C3F6). The reactor was heated to 100°C. The pressure gradually increased and then decreased, stabilizing after 8 hours of reaction. The reaction system was then cooled to room temperature.

[0480] After degassing, the autoclave was flushed with helium, opened, and the reaction mixture was collected. The organic phase was separated using a separation funnel, washed, dried, and then analyzed by gas chromatography (area percentage method).

[0481] The yield of CF3-CFI-CF2I, expressed as the ratio of moles of detected CF3-CFI-CF2I to moles of initially introduced hexafluoropropene, was 81.3%. The experiment was repeated twice, varying the temperature between 80 and 100°C. Similar yield values ​​were obtained.

[0482] Step b): The apparatus used consisted of a Hastelloy C276 autoclave with a volume of 0.8 L, on which a condenser and a pressure regulating valve were attached.

[0483] The autoclave was immersed in liquid nitrogen, and the following components were sequentially introduced: 60 g (3.0 mol) of hydrofluoric acid (all three washed and dried reaction mixtures from step a) and 13.3 g (0.07 mol) of titanium tetrachloride (TiCl4). The autoclave temperature was then raised to room temperature (25°C). The autoclave was then immersed in an oil bath, and the temperature was raised to 80°C while maintaining the condenser temperature at approximately 17°C.

[0484] During the reaction, volatile products were continuously removed, washed with water, and recovered. After 4 hours of reaction, the autoclave was cooled to room temperature. The reaction products were then degassed, washed, dried, and analyzed by gas chromatography.

[0485] The yield of CF3-CFI-CF3, expressed as the ratio of the number of moles of detected CF3-CFI-CF3 to the number of moles of hexafluoropropene initially introduced, was 76.8%.

[0486] Example 2 - Synthesis of CF3-CF2-CHFI Step a): The apparatus used consisted of a 2.0 L Hastelloy C276 autoclave equipped with a pressure indicator, thermal measuring probe, rupture disc, and magnetic bar agitator.

[0487] The following were continuously introduced into the autoclave: 102.0 g (0.4 mol) of iodine, 600.0 g of anhydrous ethanol, and 53.0 g (0.4 mol) of (Z)-CF3-CF=CHF(HFO-1225ye(Z)). The reactor was heated at 70°C for 8 hours, and then cooled to room temperature.

[0488] After degassing, the autoclave was flushed with helium, and the reaction mixture was collected after opening the autoclave. The organic phase was washed, dried, and analyzed by gas chromatography (area percentage method).

[0489] The yield of CF3-CFI-CHFI, expressed as the ratio of the number of moles of detected CF3-CFI-CHFI to the number of moles of HFO-1225ye(Z) initially introduced, was 67.4%.

[0490] Step b): The apparatus used consisted of a 0.5 L Hastelloy C276 autoclave equipped with a pressure indicator, thermal measuring probe, rupture disc, and magnetic bar agitator.

[0491] The autoclave was immersed in liquid nitrogen, and the following components were sequentially introduced: 20 g (1.0 mol) of hydrofluoric acid, 96.2 g (0.25 mol) of CF3-CFI-CHFI, and 100.0 g of tetramethylene sulfone (sulfolane). The autoclave temperature was then raised to room temperature (25°C), and then gradually heated to 100°C.

[0492] Four hours after the reaction, the autoclave was cooled to room temperature. The reaction products were then degassed, washed, dried, and analyzed by gas chromatography.

[0493] The yield of CF3-CF2-CHFI, expressed as the ratio of the number of moles of detected CF3-CF2-CHFI to the number of moles of initially introduced CF3-CFI-CHFI, was 98.6%.

Claims

1. A method for producing iodofluoroalkane compounds, including the following steps: a) A step of contacting a fluoroolefin with hydrogen iodide to form a flow A containing the iodofluoroalkane compound and unreacted hydrogen iodide, b) A step of separating the flow A into a first flow B1 containing the iodofluoroalkane compound and a flow B2 containing unreacted hydrogen iodide. c) A process to recirculate flow B2 back to process a).

2. The method according to claim 1, characterized in that the hydrogen iodide is anhydrous.

3. The method according to claim 1 or 2, characterized in that the fluoroolefin is anhydrous.

4. The fluorinated olefin is of the formula (I) (R １ , １０ , ４ , １ , １０ , ６ , １０ , ３ , １０ , ２ , １０ , ３ , ３ , ４ , ２ )(R ２ )(R ３ )(R ４ ), wherein R １ , R ２ , R ３ and R<000​​​​​​​​​​​​​​​​​​​​​​​​​​​​​

5. The aforementioned fluoroolefin is of formula (I) (R １） (R ２ ) C = C(R ３ ) (Caution ４ ) is of the same type, and in the formula, R １ , R ２ , R ３ and R ４ These are H, F, I, C, independently of each other. １ -C ５ Perfluoroalkyl groups, C ５ -C １０ Perfluorocycloalkyl group, C ２ -C ５ Perfluoroalkenyl group, C ５ -C １０ Perfluorocycloalkenyl group, C ６ -C １０ Selected from the group consisting of perfluoroaryl groups, provided that substituent R １ , R ２ , R ３ or R ４ The method according to any one of claims 1 to 4, characterized in that at least one of them is F or a perfluoro group as described above.

6. The aforementioned fluoroolefin is of formula (I) (R １） (R ２ ) C = C(R ３ ) (Caution ４ ) is of the same type, and in the formula, R １ , R ２ , R ３ and R ４ These are H, F, or Y, independently of each other. １ -[-C(Y ２ ) (Y ３ ) - ] ｎ - (in the formula, Y １ , Y ２ and Y ３ The substituents R are selected independently of each other and independently of each unit n from the group consisting of H and F, where n is an integer from 1 to 5, but the substituent R １ , R ２ , R ３ , R ４ , Y １ , Y ２ or Y ３ The method according to any one of claims 1 to 4, characterized in that at least one of them is F.

7. The iodofluoroalkane compound is of formula (II) (R １ ) (Caution ２ )CH-C(I)(R ３ ) (Caution ４ A compound of ) in which R １ , R ２ , R ３ and R ４ The method according to claim 4, characterized in that the iodofluoroalkane compound is of formula (II) (R １ ) (Caution ２ )CH-C(I)(R ３ ) (Caution ４ A compound of ) in which R １ , R ２ , R ３ and R ４ The method according to claim 5, characterized in that the iodofluoroalkane compound is of formula (II) (R １ ) (Caution ２ )CH-C(I)(R ３ ) (Caution ４ A compound of ) in which R ２ , R ３ and R ４ The method according to claim 6, characterized in that the part is as described in claim 6.

8. The fluoroolefin is CHF=CH ２ CF ２ =CH ２ CHF=CHF, CF ２ =CHF, CF ２ =CF ２ CH ３ -CF=CH ２ CH ３ -CH=CHF, CH ２ F-CH=CH ２ CH ３ -CF=CHF, CH ２ F-CF=CH ２ CH ３ -CH=CF ２ CH ２ F-CH=CHF, CHF ２ -CH=CH ２ CH ３ -CF=CF ２ CH ２ F-CF=CHF, CHF ２ -CF=CH ２ CH ２ F-CH=CF ２ CHF ２ -CH=CHF, CF ３ -CH=CH ２ CH ２ F-CF=CF ２ CHF ２ -CF=CHF, CF ３ -CF=CH ２ CHF ２ -CH=CF ２ CF ３ -CH=CHF, CHF ２ -CF=CF ２ CF ３ -CF=CHF, CF ３ -CH=CF ２ CF ３ -CF=CF ２ selected from the group consisting of, preferably CF ２ =CH ２ CF ２ =CHF, CF ２ =CF ２ CF ３ -CH=CH ２ CF ３ -CF=CH ２ CF ３ -CH=CHF, CF ３ -CF=CHF, CF ３ -CF = CF ２ The method according to any one of claims 1 to 4, characterized in that it is selected from the group consisting of the following.

9. The iodo fluoroalkane compound is CH ２ F-CH ２ I, CHFI-CH ３ 、CHF ２ -CH ２ I, CF ２ I-CH ３ 、CH ２ F-CHFI, CHF ２ -CHFI, CF ２ I-CH ２ F, CHF ２ -CF ２ I, CH ３ -CHF-CH ２ I, CH ３ -CFI-CH ３ 、CH ３ -CH ２ -CHFI, CH ３ -CHI-CH ２ F, CH ２ F-CH ２ -CH ２ I, CH ３ -CHF-CHFI, CH ３ -CFI-CH ２ F, CH ２ F-CHF-CH ２ I, CH ３ -CH ２ -CF ２ I, CH ３ -CHI-CHF ２ 、CH ２ F-CH ２ -CHFI, CH ２ F-CHI-CH ２ F, CHF ２ -CH ２ -CH ２ I, CH ３ -CHF-CF ２ I, CH ３ -CFI-CHF ２ 、CH ２ F-CHF-CHFI, CH ２ F-CFI-CH ２ F, CHF ２ -CHF-CH ２ I, CH ２ F-CH ２ -CF ２ I, CH ２ F-CHI-CHF ２ 、CHF ２ -CH ２ -CHFI、CF ３ -CH ２ -CH ２ I、CF ３ -CHI-CH ３ 、CH ２ F-CHF-CF ２ I、CH ２ F-CFI-CHF ２ 、CHF ２ -CHF-CHFI、CF ３ -CHF-CH ２ I、CF ３ -CFI-CH ３ 、CHF ２ -CH ２ -CF ２ I、CHF ２ -CHI-CHF ２ 、CF ３ -CH ２ -CHFI、CF ３ -CHI-CH ２ F、CHF ２ -CHF-CF ２ I、CHF ２ -CFI-CHF ２ 、CF ３ -CHF-CHFI、CF ３ -CFI-CH[[ID=~66]] ２ F、CF ３ -CH ２ -CF ２ I、CF ３ -CHI-CHF ２ 、CF ３ -CHF-CF ２ I、CF ３ -CFI-CHF ２ selected from the group consisting of, preferably CHF ２ -CH ２ I、CF ２ I-CH ３ 、CHF ２ -CHFI、CF ２ I-CH ２ F、CHF ２ -CF ２ I、CF ３ -CH<~ ２ -CH ２ I, CF ３ -CHI-CHI ３ CF ３ -CHF-CH ２ I, CF ３ -CFI-CH ３ CF ３ -CH ２ - CHFI, CF ３ -CHI-CHI ２ F, CF ３ -CHF-CHFI, CF ３ -CFI-CH ２ F, CF ３ -CHF-CF ２ I, CF ３ -CFI-CHF ２ The method according to any one of claims 1 to 8, characterized in that it is selected from the group consisting of the following.

10. Step a) is, - CF ２ =CH ２ to CF ２ I-CH ３ Converting to; or - CF ２ = CHF to CF ２ I-CH ２ Convert to F; or - CF ２ =CF ２ to CHF ２ -CF ２ Converting to I; or - CF ３ -CH=CH ２ to CF ３ -CH ２ -CH ２ Converting to; or - CF ３ -CF=CH ２ to CF ３ -CFI-CH ３ Converting to; or - CF ３ -CH=CHF to CF ３ -CH ２ - Converting to CHFI; or - CF ３ -CF = CHF to CF ３ - Converting CHF to CHFI; or - CF ３ -CF = CF ２ to CF ３ -CHF-CF ２ Convert to I The method according to any one of claims 1 to 3, characterized in that it also includes

11. The method according to any one of claims 1 to 10, characterized in that the fluoroolefin has a boiling point below 100°C at atmospheric pressure.

12. The method according to any one of claims 1 to 11, characterized in that step a) is carried out in the gas phase in the presence of a catalyst selected from the group consisting of oxides, oxyhalides, or halides of metals from groups 4 to 12 of the periodic table or metals selected from Li, Na, K, Cs, Mg, Ca, Al, and Sb.

13. The method according to any one of claims 1 to 12, characterized in that step a) is carried out at a temperature of 150°C to 700°C.

14. The method according to any one of claims 1 to 10, wherein step a) is carried out in the liquid phase in the presence of a catalyst selected from alkali metal salts or alkaline earth metal salts and solvent S1.

15. The method according to any one of claims 1 to 14, wherein step a) is carried out in the presence of a solvent S1 having a boiling point of 20°C to 250°C.