Method for producing fluoroiodoalkane and device for producing fluoroiodoalkane

Abstract

To provide a novel industrial production method for fluoroiodoalkanes characterized by its simplicity and minimal production equipment constraints.SOLUTION: A method for producing a fluoroiodoalkane includes reacting perfluoroalkyl iodide with ethylene in the presence of an amine through light irradiation within an organic solvent.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] The present invention relates to a novel method for producing fluoroiodoalkanes and an apparatus using said method. [Background technology]

[0002] Fluoroiodoalkanes are widely used, for example, to make liquid compositions such as solvents, cleaning agents, and refrigerants flame retardant, or to synthesize intermediates for pharmaceuticals and agricultural chemicals (see, for example, Patent Document 1).

[0003] As a method for producing fluoroiodoalkanes, Patent Document 2 discloses a method for obtaining fluoroiodoalkanes by iodinating fluorine-containing alkyl-substituted ethyl halides obtained by reducing fluorine-containing alkyl-substituted vinyl halides. However, this reaction requires multiple steps, resulting in poor production efficiency, and furthermore, the reduction step requires a high-pressure reaction at a gauge pressure of 2 MPa, which requires specific equipment under the High Pressure Gas Safety Act, resulting in problems with restrictions on production equipment.

[0004] Non-Patent Document 1 discloses a method for producing fluoroiodoalkanes by reacting perfluoroalkyl iodides with unsaturated hydrocarbons. However, this method requires a large excess of expensive trifluoroiodomethane, and the reaction temperature is 200° C., so the reaction system is expected to be at high pressure, and sufficient void ratio is required in the reaction vessel, resulting in poor production efficiency and making it an unsuitable method for industrial mass production.

[0005] Non-Patent Document 2 discloses a method for producing fluoroiodoalkanes by reacting perfluoroalkyl iodides with unsaturated hydrocarbons through a photoreaction. However, the reaction efficiency is poor, requiring a long time, and there are problems with the selectivity decreasing due to the overreaction of the produced fluoroiodoalkanes.

[0006] Non-Patent Document 3 discloses a method for producing fluoroiodoalkanes by reacting a perfluoroalkyl iodide with an unsaturated hydrocarbon through a photoreaction. However, this reaction has a problem in that it requires a large excess of an expensive perfluoroalkyl iodide, and the unsaturated hydrocarbon is limited to a substrate having a high boiling point and a carbon number of 3 or more.

[0007] Furthermore, a method for producing fluoroiodoalkanes by using a radical initiator to radically add a perfluoroalkyl iodide to an unsaturated hydrocarbon under heating is well known. However, this method has problems such as the possibility that the substrate or product used may be thermally decomposed or that side reactions such as telomerization, in which the product undergoes further radical addition, may occur.

[0008] Here, gauge pressure is a relative pressure notation when atmospheric pressure is set to 0, and indicates the pressure relative to the ambient pressure. [Prior art documents] [Patent documents]

[0009] [Patent Document 1] JP 2022-113658 A [Patent Document 2] JP 2010-1272 A [Non-patent literature]

[0010] [Non-Patent Document 1] Journal of the Chemical Society C: Organic,1970,3,414-421 [Non-Patent Document 2] Journal of the Chemical Society (Resumed), 1949, pp. 2856-2861 [Non-Patent Document 3] Organic LETTERS, 2017, Volume 19, Pages 1442-1445 Summary of the Invention [Problem to be solved by the invention]

[0011] In view of the above-mentioned background art, an object of the present invention is to provide a novel production method which is simple and has few restrictions on production equipment, and which can provide fluoroiodoalkanes in good yield, and an apparatus using this production method. [Means for solving the problem]

[0012] As a result of intensive research to solve the above-mentioned problems, the inventors discovered that by reacting a perfluoroalkyl iodide with ethylene in the presence of amines in an organic solvent by irradiating it with light, fluoroiodoalkanes can be produced in a short time without requiring specific equipment under the High Pressure Gas Safety Act because the reaction pressure is low, and thus, they have completed the present invention.

[0013] That is, the present invention relates to the following inventions. [1] The following general formula (1) Rf-I (1) (In the general formula (1), Rf represents a linear, branched or cyclic perfluoroalkyl group having 1 to 6 carbon atoms.) and ethylene in the presence of an amine in an organic solvent by light irradiation to form a compound represented by the following general formula (2): Rf-CH2CH2-I (2) (In the general formula (2), Rf represents a linear, branched or cyclic perfluoroalkyl group having 1 to 6 carbon atoms.) A method for producing a fluoroiodoalkane represented by the following formula: [2] The organic solvent is at least one selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, diethyl ketone, diisobutyl ketone, 2-pentanone, 2-hexanone, cyclopentanone, cyclohexanone, dimethyl sulfoxide and acetonitrile. The method according to [1]. [3] The amines are represented by the following general formula (3): [ka] (In formula (3), R 1 , R 2 and R 3 each independently represents a hydrogen atom or a linear, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms; R 1 , R 2 and R 3 Any two or all of R may be bonded to each other to form a ring. 1 , R 2 and R 3 are not all hydrogen atoms.) The manufacturing method according to item [1], having a structure represented by the formula: [4] The manufacturing method according to item [1], wherein the wavelength of the light used for irradiation is 250 nm to 450 nm. [5] The method according to any one of items [1] to [4], wherein the amine is a tertiary amine. [6] The method according to any one of items [1] to [4], wherein the perfluoroalkyl iodide is trifluoroiodomethane. [7] The method according to any one of items [1] to [4], wherein the organic solvent is acetone and the amine is triethylamine. [8] The method according to any one of items [1] to [4], wherein the perfluoroalkyl iodide is trifluoroiodomethane, the organic solvent is acetone, and the amine is triethylamine. [9] The method according to any one of items [1] to [4], wherein a flow reactor is used for the reaction.

[10] A container for storing a mixed solution of a perfluoroalkyl iodide, an amine, and an organic solvent; A pump that delivers the mixed solution through a pipe; a vessel equipped with a mass flow controller and configured to store ethylene; a mixer for mixing the mixed solution and the ethylene; a light irradiation unit to which the mixed solution and ethylene are fed through a pipe and which irradiates the mixed solution with light to initiate a reaction between the mixed solution and ethylene; a retention time unit in which the mixed solution and ethylene are delivered from the light irradiation unit through a pipe and the mixed solution and ethylene are retained for a predetermined time to allow the reaction to proceed; a back pressure valve for adjusting the pressure when the perfluoroalkyl iodide is in a gaseous state at room temperature; Equipped with The mass flow controller can supply the ethylene through a pipe and control the amount of the ethylene. Fluoroiodoalkane manufacturing equipment.

[11] A container for storing a mixed solution 1 containing an amine and an organic solvent; A pump that delivers the mixed solution 1 through a pipe; A container for storing a mixed solution 2 containing a perfluoroalkyl iodide and an organic solvent; A pump that delivers the mixed solution 2 through a pipe; a mixer for mixing the mixed solution 1 and the mixed solution 2 to obtain a mixed solution 3; a vessel equipped with a mass flow controller and configured to store ethylene; a mixer for mixing the mixed solution 3 and the ethylene; a light irradiation unit to which the mixed solution 3 and ethylene are delivered via a pipe and which is irradiated with light to initiate a reaction between the mixed solution and ethylene; a retention time unit in which the mixed solution 3 and ethylene are sent from the light irradiation unit through a pipe and the mixed solution and ethylene are retained for a predetermined time to allow the reaction to proceed; a back pressure valve for adjusting the pressure when the perfluoroalkyl iodide is in a gaseous state at room temperature; Equipped with The mass flow controller can supply the ethylene through a pipe and control the amount of the ethylene. Fluoroiodoalkane manufacturing equipment. Effect of the Invention

[0014] According to the present invention, there are provided a novel and simple industrial method for producing fluoroiodoalkanes which requires fewer restrictions on production equipment, and an apparatus using this production method. [Brief description of the drawings]

[0015] [Figure 1] FIG. 1 is a diagram showing the configuration of a flow reactor which is an embodiment of the method for producing fluoroiodoalkanes of the present invention. [Diagram 2] FIG. 1 is a diagram showing the configuration of a multi-stage flow reactor which is an embodiment of the method for producing fluoroiodoalkanes of the present invention.

[0016] The present invention will be described in detail below.

[0017] The present invention relates to a compound represented by the following general formula (1): Rf-I (1) (wherein Rf represents a linear, branched or cyclic perfluoroalkyl group having 1 to 6 carbon atoms) is reacted with ethylene in the presence of an amine by irradiation with light in an organic solvent to obtain a compound represented by the following general formula (2): Rf-CH2CH2-I (2) (In the general formula (2), Rf represents a linear, branched or cyclic perfluoroalkyl group having 1 to 6 carbon atoms.)

[0018] In the perfluoroalkyl iodide represented by the above general formula (1), Rf is a linear, branched or cyclic perfluoroalkyl group having 1 to 6 carbon atoms, of which a linear perfluoroalkyl group having 1 to 3 carbon atoms is preferred, and a perfluoroalkyl group having 1 to 2 carbon atoms is particularly preferred.

[0019] The organic solvent used in the reaction in the present invention is not particularly limited as long as it does not inhibit the reaction, and examples thereof include acetone, methyl ethyl ketone, methyl isobutyl ketone, diethyl ketone, diisobutyl ketone, 2-pentanone, 2-hexanone, cyclopentanone, cyclohexanone, dimethyl sulfoxide, and acetonitrile, among which acetone is preferably used. These can be used alone, or two or more types can be mixed and used.

[0020] In the present invention, the amines used in the reaction are represented by the following general formula (3): [ka] (In formula (3), R 1 , R 2 and R 3 each independently represents a hydrogen atom or a linear, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms; R 1 , R 2 and R 3 Any two or all of the above may be bonded together to form a ring, such as 1-Azabicyclo[1.1.1]pentane (CAS: 34743-91-4). 1 , R 2 and R 3 are not all hydrogen atoms.

[0021] The amines that can be used include primary amines, secondary amines, and tertiary amines. Examples of primary amines include normal propylamine, isopropylamine, methylamine, normal butylamine, and ethylenediamine. Examples of the secondary amine include diethylamine, diisopropylamine, pyrrolidine, N,N'-dimethylethylenediamine, and proline. Examples of tertiary amines include triethylamine, diisopropylethylamine, N-methylmorpholine, N-ethylmorpholine, N-methylpiperidine, N-ethylpiperidine, N-methylpiperazine, N-ethylpiperazine, 1,4-diazabicyclo[2,2,2]octane, N,N,N',N'',N''-pentamethyldiethylenetriamine, N,N,N',N'-tetraethylethylenediamine, N,N,N',N'-tetramethyl-1,3-propanediamine, pyridine, 1,8-diazabicyclo[5.4.0]undec-7-ene, phenanthroline, and N,N,N',N'-tetramethylethylenediamine. Among these, tertiary amines are preferred, and triethylamine is particularly preferred. These amines can be used alone or in combination of two or more.

[0022] The amount of the amine used in the reaction of the present invention is preferably 0.01 mol to 2.0 mol, more preferably 0.01 mol to 1.0 mol, and particularly preferably 0.01 mol to 0.5 mol, per mol of the perfluoroalkyl iodide used in the reaction.

[0023] The perfluoroalkyl iodide used in the reaction in the present invention is represented by the following general formula (1): Rf-I (1) (In general formula (1), Rf represents a linear, branched or cyclic perfluoroalkyl group having 1 to 6 carbon atoms.) is preferable, more preferably in general formula (1), Rf represents a linear perfluoroalkyl group having 1 to 3 carbon atoms, and particularly preferably trifluoroiodomethane.

[0024] The light source applicable to the reaction of the present invention is not particularly limited as long as the wavelength of light emitted is 100 nm to 500 nm, preferably 250 nm to 450 nm. For example, ordinary external light (sunlight) or a commercially available light-emitting diode (LED) for chemical experiments can be used as long as it does not deviate from the intended purpose.

[0025] When using an LED as a light source, a white LED, UV LED, or the like can be used as appropriate as long as it can cover wavelengths of, for example, about 365 nm or about 405 nm. It is also preferable to control the light intensity during light irradiation, and when using an LED, it is sufficient to use one with an appropriate wattage (W).

[0026] The reaction of the present invention can be suitably carried out in either a batch reactor or a flow reactor. In the case of a flow system, a light source device such as an LED with an intensity of 30 W (watts), 60 W, 120 W, 240 W, or 480 W within these ranges can be used, and can be appropriately determined taking into consideration various factors such as the type of reaction, the amount of raw materials, flow rate, and residence time in the light irradiation area. In the case of a batch system, light may be constantly irradiated during a given reaction, and the intensity may be varied over time. For example, a light source device such as an LED having an intensity of 10 W (watts), 20 W, 40 W, or 60 W or within these ranges may be used.

[0027] In the present invention, either a batch reactor or a flow reactor can be used, and the wavelength, irradiation intensity, etc. can be appropriately changed depending on the reaction system, scale, etc. to be applied. Furthermore, a photosensitizer can be appropriately used to increase the intensity of light irradiation. Any photosensitizer can be used as long as it does not affect the reaction and has a sensitizing effect that can cover the required wavelengths.

[0028] When the reaction of the present invention is carried out using a batch reactor, it is desirable for the apparatus to satisfy the following requirements: it should be a container of a size appropriate to the amounts of various materials used in the production, it should not cause reactions other than the intended purpose, such as reactions with the various materials used in the production, it should be made of a material that does not block light irradiation into the container if it has an external light source, and if it is sealed, it should be a pressure-resistant container appropriate to the pressure level during production.

[0029] When the reaction of the present invention is carried out using a flow reactor (1), the apparatus may be one consisting of a liquid delivery pump (4), a mixer (5), a light irradiation unit (8), and a residence time unit (9) as shown in FIG. 1. If the perfluoroalkyl iodide is a gas at room temperature, the reaction can be carried out without vaporization by providing a back pressure valve (10). A mixed solution of perfluoroalkyl iodide, an organic solvent, and amines is delivered by a pump (4) and mixed with ethylene supplied from a cylinder (6) equipped with a mass flow controller (7) in a mixer (5). The mixture is then passed through the light irradiation unit (8) and the residence time unit (9) in that order. At this time, the reaction is initiated by the light irradiation unit (8), and the reaction proceeds during the process of passing through the residence time unit (9).

[0030] The method of delivering the mixed solution is not particularly limited, and examples thereof include a method in which a multi-stage flow reactor (11) is assembled as shown in Fig. 2, and the mixed solution of an organic solvent and amines and perfluoroalkyl iodide are supplied from cylinders (2a, 2b) equipped with two pumps (4) or one pump (4) and a mass flow controller (7), mixed in the first mixer (5), and then mixed with ethylene supplied from a cylinder (6) equipped with a mass flow controller (7) in the second mixer (5). When the perfluoroalkyl iodide is a gas, examples of the method include a method in which the perfluoroalkyl iodide is cooled to a temperature at which it does not vaporize before being delivered.

[0031] When the reaction of the present invention is carried out using a flow reactor, the mixer used may be an α-type micromixer (manufactured by MiChS Co., Ltd. (registered trademark)), a T-shaped mixer such as a Union T, or a turbulent mixer such as a β-type mixer (manufactured by MiChS Co., Ltd.). The inner diameter (flow path width) of the mixer is appropriately selected depending on the reaction scale, and a mixer in the range of 70 μm to 1 / 8 inch (3.175 mm) is preferably used.

[0032] When the reaction of the present invention is carried out using a flow reactor, the inner diameter of the residence time unit is preferably 0.5 mm to 5 mm, more preferably 2 mm to 4 mm. The length of the residence time unit is preferably 2 m to 4 m. The flow rate of the flow treatment can be set arbitrarily depending on the charge ratio (molar ratio) of the chemical solution and ethylene to be fed, the residence time, and the length and inner diameter of the residence time unit. For example, the length of the residence time unit can be set to be 1 to 10 times the residence time of the light irradiation unit.

[0033] The amount of ethylene used in the reaction of the present invention is preferably 1.0 mol to 2.0 mol, more preferably 1.0 mol to 1.5 mol, and particularly preferably 1.0 mol to 1.2 mol, per mol of perfluoroalkyl iodide used in the reaction.

[0034] The reaction temperature in the present invention is usually preferably in the range of -20°C to 40°C, more preferably in the range of 0°C to 30°C, in either a batch reactor or a flow reactor.

[0035] As described above, when the method for producing fluoroiodoalkanes of the present invention is carried out using a flow reactor, the apparatus exemplified in Figures 1 and 2 can be used. Examples of this apparatus include the following aspects.

[0036] 1) When a mixed solution of a perfluoroalkyl iodide, an amine, and an organic solvent capable of dissolving them is used for the reaction, a container for storing a mixed solution of a perfluoroalkyl iodide, an amine, and an organic solvent; A pump that delivers the mixed solution through a pipe; a vessel equipped with a mass flow controller and configured to store ethylene; a mixer for mixing the mixed solution and the ethylene; a light irradiation unit to which the mixed solution and ethylene are fed through a pipe and which irradiates the mixed solution with light to initiate a reaction between the mixed solution and ethylene; a retention time unit in which the mixed solution and ethylene are delivered from the light irradiation unit through a pipe and the mixed solution and ethylene are retained for a predetermined time to allow the reaction to proceed; a back pressure valve for adjusting the pressure when the perfluoroalkyl iodide is in a gaseous state at room temperature; Equipped with The mass flow controller can supply the ethylene through a pipe and control the amount of the ethylene. Fluoroiodoalkane manufacturing equipment.

[0037] 2) In the case where a perfluoroalkyl iodide and an organic solvent capable of dissolving the perfluoroalkyl iodide are used as mixed solvent 1, and an amine and an organic solvent capable of dissolving the amine are used as mixed solution 2, the mixture is subjected to the reaction. A container for storing a mixed solution 1 containing an amine and an organic solvent; A pump that delivers the mixed solution 1 through a pipe; A container for storing a mixed solution 2 containing a perfluoroalkyl iodide and an organic solvent; A pump that delivers the mixed solution 2 through a pipe; a mixer for mixing the mixed solution 1 and the mixed solution 2 to obtain a mixed solution 3; a vessel equipped with a mass flow controller and configured to store ethylene; a mixer for mixing the mixed solution 3 and the ethylene; a light irradiation unit to which the mixed solution 3 and ethylene are delivered via a pipe and which is irradiated with light to initiate a reaction between the mixed solution and ethylene; a retention time unit in which the mixed solution 3 and ethylene are sent from the light irradiation unit through a pipe and the mixed solution and ethylene are retained for a predetermined time to allow the reaction to proceed; a back pressure valve for adjusting the pressure when the perfluoroalkyl iodide is in a gaseous state at room temperature; Equipped with The mass flow controller can supply the ethylene through a pipe and control the amount of the ethylene. Fluoroiodoalkane manufacturing equipment.

[0038] The post-treatment after the reaction of the present invention can be carried out by a known method, and the reaction product can be purified directly or after washing with water. It can be isolated or purified by distillation under normal pressure or reduced pressure to obtain fluoroiodoalkanes, which are the target compounds of the present invention. For example, after obtaining a crude product by simple distillation, it may be further purified by precision distillation as necessary. EXAMPLES

[0039] Examples of the present invention are shown below, but the present invention is not limited to these examples.

[0040] The following instruments were used for the analysis: <nmr> 1 H-NMR (400MHz), 19 F-NMR (376MHz): Bruker AVANCE II 400 <gc> SHIMADZU GC-2014

[0041] Example 1 Production of trifluoroiodopropane in a batch reactor 7.8g of acetone (0.13mol, Mitsui Chemicals) and 0.03g of triethylamine (0.3mmol, Fujifilm Wako Pure Chemical Industries) were added to a 40mL pressure-resistant tube (ACE GLASS). After bubbling 0.54g of trifluoroiodomethane (2.8mmol, Tosoh Finechem Co., Ltd.) with ice cooling, 0.1g of ethylene (0.04mol, Air Water Inc.) was bubbled in, and 405nm UV irradiation was performed for 60 minutes using an LED light (Contec Co., Ltd., output 11W) at room temperature. Then, 0.02g of triethylamine (0.2mmol) was added, and after bubbling 0.1g of ethylene (0.04mol) with ice cooling, 405nm UV irradiation was performed for 60 minutes using an LED light, and the same operation was repeated once more. After that, 7.57g of brown transparent liquid was obtained. Benzotrifluoride is used as an internal standard 19 F-NMR analysis showed that the brown transparent liquid contained 5.2% by weight of trifluoroiodopropane (yield 63%). The yield of the by-product in which one molecule of ethylene was further inserted into trifluoroiodopropane was 3% ( 19 F-NMR). The yield was based on the starting material trifluoroiodomethane (molar yield).

[0042] The analysis results were as follows: 1 H-NMR (solvent: deuterated chloroform, internal standard: chloroform) δ (ppm): 2.46 (qt, 2H, CH2), 2.95 (t, 2H, CH2). 19 F-NMR (solvent: deuterated chloroform, internal standard: benzotrifluoride) δ (ppm): -67.6 (s, 3F, CF3).

[0043] Example 2 Production of pentafluoroiodobutane in a batch reactor A 40mL pressure-resistant tube (ACE GLASS) was charged with 7.6g of acetone (0.13mol, Mitsui Chemicals) and 0.014g of triethylamine (0.14mmol, Fujifilm Wako Pure Chemicals). After bubbling with 0.35g of pentafluoroiodoethane (1.4mmol, Tosoh Finechem), 0.1g of ethylene (0.04mol, Air Water Inc.) was added under ice cooling, and 405nm UV irradiation was performed for 60 minutes using an LED light (Contec Co., Ltd., output 11W) at room temperature. Then, 0.014g of triethylamine (0.14mmol) was added, and after bubbling with 0.1g of ethylene (0.04mol) under ice cooling, 405nm UV irradiation was performed for 60 minutes using an LED light. The same operation was repeated once more. After that, 7.42g of brown transparent liquid was obtained. Benzotrifluoride is used as an internal standard 19 F-NMR analysis showed that the brown transparent liquid contained 4.8% by weight of trifluoroiodopropane (yield 92%). The yield of the by-product in which one molecule of ethylene was further inserted into trifluoroiodopropane was 2% ( 19 F-NMR). The yield was based on the starting material pentafluoroiodoethane (molar yield).

[0044] The analysis results were as follows: 1 H-NMR (solvent: deuterated chloroform, internal standard: chloroform) δ (ppm): 2.36 (tdd, 2H, CH2), 2.89 (dd, 2H, CH2). 19 F-NMR (solvent: deuterated chloroform, internal standard: benzotrifluoride) δ (ppm): -86.27 (s, 3F, CF3), -119.51 (s, 2F, CF2).

[0045] Example 3 Production of trifluoroiodopropane in a flow reactor Photochemical synthesis of trifluoroiodopropane was carried out using trifluoroiodomethane and ethylene. Trifluoroiodomethane (24.8g, 127mmol, Tosoh Finechem) was dissolved in degassed acetone (37mL, 0.50mol, Nacalai Tesque) (2.5M), and triethylamine (634mg, 6.26mmol, 5mol%, Tokyo Chemical Industry Co., Ltd.) and benzotrifluoride (1.82g, 12.5mmol, 1mol%, Tokyo Chemical Industry Co., Ltd.) were added as an internal standard to prepare a raw material solution. The raw material solution was transferred to a container filled with nitrogen gas, connected to a nitrogen balloon, sealed, and then immersed in an ice bath. The raw material solution was pumped at 0.1 mL / min. Meanwhile, ethylene (Sumitomo Seika Chemicals Co., Ltd.) was pumped at 6.1 mL / min via a mass flow controller, and each was mixed in a T-shaped mixer with an inner diameter of 200 μm. The resulting slug-like reaction solution was introduced into a tube reactor (1 / 16 PFA tube, length 4 m, diameter 1 mm) immersed in a water bath at 20°C, and light irradiation was performed using a UV-LED (wavelength = 365 nm, output = 60 W) while the solution was being pumped. A back pressure regulator (gauge pressure 40 psi) was connected to the end of the tube reactor to control the pressure in the reaction system. The reaction solution was collected from the reactor outlet and analyzed by gas chromatography (GC). 19 Analysis by F-NMR revealed that the yield of trifluoroiodopropane was 91% (GC) and the recovery rate of trifluoroiodomethane was 4% ( 19 F-NMR), the yield of the by-product in which one more molecule of ethylene was inserted into trifluoroiodopropane was 2% ( 19 F-NMR). The yield and recovery rate were both based on the starting material trifluoroiodomethane (molar yield). [Industrial Applicability]

[0046] According to the present invention, fluoroiodoalkanes can be industrially produced easily and in good yield with fewer restrictions on production equipment. [Explanation of symbols]

[0047] 1: Flow reactor 2: Mixture of perfluoroalkyl iodide, organic solvent, and amines 2a: Mixture of organic solvent and amines 2b: Perfluoroalkyl iodide, organic solvent mixture 3: Nitrogen cylinder 4: Liquid delivery pump 5: Mixer 6: Ethylene cylinder 7: Mass flow controller 8: Light irradiation unit 9: Residence time unit 10: Back pressure valve 11: Multi-stage flow reactor< / gc> < / nmr>

Claims

1. The following general formula (1) Rf-I (1) (In the general formula (1), Rf represents a linear, branched or cyclic perfluoroalkyl group having 1 to 6 carbon atoms.) and ethylene in the presence of an amine in an organic solvent by light irradiation to form a compound represented by the following general formula (2): Rf-CH ２ CH ２ -I (2) (In the general formula (2), Rf represents a linear, branched or cyclic perfluoroalkyl group having 1 to 6 carbon atoms.) A method for producing a fluoroiodoalkane represented by the following formula:

2. The method according to claim 1, wherein the organic solvent is at least one selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, diethyl ketone, diisobutyl ketone, 2-pentanone, 2-hexanone, cyclopentanone, cyclohexanone, dimethyl sulfoxide, and acetonitrile.

3. The amines used in the reaction of the present invention are represented by the following general formula (3): 【Chemistry 3】 (In formula (3), R １ , R ２ and R ３ each independently represents a hydrogen atom or a linear, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms, and may be bonded to each other to form a ring, １ , R ２ and R ３ are not all hydrogen atoms.) The method according to claim 1, wherein the compound is at least one selected from the group represented by the formula:

4. The method according to claim 1, wherein the wavelength of the light to be irradiated is from 250 nm to 450 nm.

5. The method according to any one of claims 1 to 4, wherein the amine is at least one selected from the group consisting of tertiary amines.

6. The method according to any one of claims 1 to 4, wherein the perfluoroalkyl iodide is trifluoroiodomethane.

7. The process according to any one of claims 1 to 4, wherein the organic solvent is acetone and the amine is triethylamine.

8. The method according to any one of claims 1 to 4, wherein the perfluoroalkyl iodide is trifluoroiodomethane, the organic solvent is acetone, and the amine is triethylamine.

9. The method according to any one of claims 1 to 4, wherein a flow reactor is used for the reaction.

10. a container for storing a mixed solution of a perfluoroalkyl iodide, an amine, and an organic solvent; A pump that delivers the mixed solution through a pipe; a vessel equipped with a mass flow controller and configured to store ethylene; a mixer for mixing the mixed solution and the ethylene; a light irradiation unit to which the mixed solution and ethylene are fed through a pipe and which irradiates the mixed solution with light to initiate a reaction between the mixed solution and ethylene; a retention time unit in which the mixed solution and ethylene are delivered from the light irradiation unit through a pipe and the mixed solution and ethylene are retained for a predetermined time to allow the reaction to proceed; a back pressure valve for adjusting the pressure when the perfluoroalkyl iodide is in a gaseous state at room temperature; Equipped with The mass flow controller can supply the ethylene through a pipe and control the amount of the ethylene. Fluoroiodoalkane manufacturing equipment.

11. A container for storing a mixed solution 1 containing an amine and an organic solvent; A pump that delivers the mixed solution 1 through a pipe; A container for storing a mixed solution 2 containing a perfluoroalkyl iodide and an organic solvent; A pump that delivers the mixed solution 2 through a pipe; a mixer for mixing the mixed solution 1 and the mixed solution 2 to obtain a mixed solution 3; a vessel equipped with a mass flow controller and configured to store ethylene; a mixer for mixing the mixed solution 3 and the ethylene; a light irradiation unit to which the mixed solution 3 and ethylene are fed through a pipe and irradiated with light to initiate a reaction between the mixed solution and ethylene; a retention time unit in which the mixed solution 3 and ethylene are sent from the light irradiation unit through a pipe and the mixed solution and ethylene are retained for a predetermined time to allow the reaction to proceed; a back pressure valve for adjusting the pressure when the perfluoroalkyl iodide is in a gaseous state at room temperature; Equipped with The mass flow controller can supply the ethylene through a pipe and control the amount of the ethylene. Fluoroiodoalkane manufacturing equipment.

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