Composition containing halogenated alkyne compound

Abstract

The purpose of the present disclosure is to newly provide a composition containing a halogenated alkyne compound. Provided is a composition containing a halogenated alkyne compound.

Description

Composition containing a halogenated alkyne compound

[0001] This disclosure relates to compositions containing alkyne halogen compounds.

[0002] Patent Document 1 discloses a method for producing a perfluoroalkyne compound, which includes the step of reacting a perfluoroalkadiene compound in the presence of a catalyst to obtain a perfluoroalkyne compound; a composition containing a perfluoroalkyne compound and a perfluorocycloalkene compound; a catalyst used for reacting a perfluoroalkadiene compound to obtain a perfluoroalkyne compound; and a method for producing a catalyst used for reacting a perfluoroalkadiene compound to obtain a perfluoroalkyne compound.

[0003] Patent Document 2 discloses a method for producing a halogenated butene compound, which includes a step of dehydrofluorinating a halogenated butene compound; a method for producing a halogenated butyne compound, which includes a step of dehydrofluorinating a halogenated butene compound; and a method for producing a halogenated butyne compound, which includes a step of producing a halogenated butene compound by dehydrofluorinating a halogenated butene compound, and then producing a halogenated butyne compound by dehydrohalogenating the halogenated butene compound.

[0004] Patent Document 3 discloses a method for producing a perfluorocarbon compound, comprising the step of reacting a halogenated hydrocarbon compound in an organic solvent in the presence of an iodine-containing inorganic material and zinc or a zinc alloy to obtain a perfluorocarbon compound, and a method for producing a perfluoroalkyne compound, comprising the step of reacting a halogenated alkene compound in the presence of zinc or a zinc alloy in at least one nitrogen-containing polar organic solvent selected from the group consisting of N,N-dimethylacetamide, N,N-diisopropylformamide, N-methyl-2-pyrrolidone, 1,3-dimethyl-3,4,5,6-tetrahydropyrimidinone, hexamethylphosphate triamide, amine compounds, pyridine compounds, and quinoline compounds to obtain a perfluoroalkyne compound.

[0005] International Publication Number WO2020 / 075728A1 International Publication Number WO2020 / 171011A1 International Publication Number WO2020 / 204146A1

[0006] This disclosure aims to provide a new composition containing a halogenated alkyne compound.

[0007] This disclosure includes the following components:

[0008] Item 1. A composition containing a halogenated alkyne compound, wherein the composition comprises (1) General formula (1): R 1 -C≡CR 2 Alkyne halide compounds represented by (in general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom. ) (2) (2-1) A halogenated ethylene compound represented by general formula (2): CF2=CFX, (wherein general formula (2), X represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom.) (2-2) Oxygen, (2-3) Water, (2-4) Hydrogen fluoride, and (2-5) Hydrogen chloride, wherein, with respect to the total amount of the composition, (2) when the composition contains (2-1) the halogenated ethylene compound represented by general formula (2), the content of the halogenated ethylene compound represented by general formula (2) is 1 ppm by volume or more and 100 ppm by volume, when the composition contains (2-2) the oxygen, the content of the oxygen is 0.1 ppm by volume or more and 100 ppm by volume, and when the composition contains (2-3) the water, the content of the water is 0.1 ppm by volume or more and 200 ppm by volume. A composition in which (2-4) when it contains hydrogen fluoride, the content of hydrogen fluoride is 0.1 ppm by volume or more and 10 ppm by volume or less, or (2-5) when it contains hydrogen chloride, the content of hydrogen chloride is 0.1 ppm by volume or more and 10 ppm by volume or less.

[0009] Item 2. The composition according to Item 1, wherein the content of the halogenated alkyne compound represented by the general formula (1) is 95% to 99.9999% by volume, relative to the total amount of the composition.

[0010] Item 3. A method for preserving a composition containing a halogenated alkyne compound, wherein the composition is (1) General formula (1): R 1 -C≡CR 2 Alkyne halide compounds represented by (in general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom. ) (2) (2-1) A halogenated ethylene compound represented by general formula (2): CF2=CFX, (wherein general formula (2), X represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom.) (2-2) Oxygen, (2-3) Water, (2-4) Hydrogen fluoride, and (2-5) Hydrogen chloride, and the composition contains, with respect to the total amount of the composition, (2) when the composition contains the halogenated ethylene compound represented by general formula (2), the content of the halogenated ethylene compound represented by general formula (2) shall be 1 ppm by volume or more and 100 ppm by volume, when the composition contains the oxygen, the content of the oxygen shall be 0.1 ppm by volume or more and 100 ppm by volume, and when the composition contains the water, the content of the water shall be 0.1 ppm by volume or more and 200 ppm by volume. A method comprising: (2-4) when the composition contains the hydrogen fluoride, the content of the hydrogen fluoride being 0.1 ppm by volume or more and 10 ppm by volume or less; or (2-5) when the composition contains the hydrogen chloride, the content of the hydrogen chloride being 0.1 ppm by volume or more and 10 ppm by volume or less.

[0011] Item 4. The method according to Item 3, wherein the content of the halogenated alkyne compound represented by the general formula (1) is 95% to 99.9999% by volume, relative to the total amount of the composition.

[0012] Item 5. A method for suppressing the decrease in purity of a halogenated alkyne compound in a composition containing the halogenated alkyne compound, wherein the composition comprises: (1) a halogenated alkyne compound represented by the general formula (1): R 1 -C≡C-R 2 (in the general formula (1), R 1 represents a perfluoroalkyl group. In the general formula (1), R 2 represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom.), and (2) at least one component selected from the group consisting of (2-1) a halogenated ethylene compound represented by the general formula (2): CF2=CFX (in the general formula (2), X represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom), (2-2) oxygen, (2-3) water, (2-4) hydrogen fluoride, and (2-5) hydrogen chloride. When the composition contains (2-1) the halogenated ethylene compound represented by the general formula (2), the content of the halogenated ethylene compound represented by the general formula (2) is 1 volume ppm or more and 100 volume ppm or less; when the composition contains (2-2) the oxygen, the content of the oxygen is 0.1 volume ppm or more and 100 volume ppm or less; when the composition contains (2-3) the water, the content of the water is 0.1 volume ppm or more and 200 volume ppm or less; when the composition contains (2-4) the hydrogen fluoride, the content of the hydrogen fluoride is 0.1 volume ppm or more and 10 volume ppm or less; or when the composition contains (2-5) the hydrogen chloride, the content of the hydrogen chloride is 0.1 volume ppm or more and 10 volume ppm or less, based on the total amount of the composition.

[0013] Item 6. The method according to Item 5, wherein the content of the halogenated alkyne compound represented by the general formula (1) is 95 volume % to 99.9999 volume % based on the total amount of the composition.

[0014] This disclosure provides a method for stably transporting compositions containing a halogenated alkyne compound and at least one component selected from the group consisting of halogenated ethylene compounds, oxygen, water, hydrogen fluoride, and hydrogen chloride. According to this disclosure, by adjusting the content (concentration) of at least one component selected from the group consisting of halogenated ethylene compounds, oxygen, water, hydrogen fluoride, and hydrogen chloride in a composition containing a halogenated alkyne compound, polymerization or decomposition of the halogenated alkyne compound can be suppressed when transporting the composition in a cylinder or the like. This suppresses a decrease in the purity of the halogenated alkyne compound and maintains the storage stability of the composition containing the halogenated alkyne compound.

[0015] The compositions containing the halogenated alkyne compounds of this disclosure contain at least one component selected from the group consisting of halogenated ethylene compounds, oxygen, water, hydrogen fluoride, and hydrogen chloride, and have improved storage stability. Even under harsh conditions in maritime transport such as containers (e.g., temperature rise during transport), polymerization or decomposition of the halogenated alkyne compounds is suppressed, thereby enabling the stable transport of compositions containing halogenated alkyne compounds.

[0016] This disclosure provides a new composition containing a halogenated alkyne compound.

[0017] In this specification, "contains" is a concept that encompasses all of "contains," "consist essentially of," and "consist of." In this specification, when a numerical range is indicated as "A to B," it means "greater than or equal to A and less than or equal to B." In this specification, when expressions such as parts and percentages are used, they represent parts by mass, parts by weight, mass%, or weight% (wt%).

[0018] [1] Compositions containing halogenated alkyne compounds: When olefins, oxygen (O2), water, hydrogen fluoride (HF), or hydrogen chloride (HCl) are present in a halogenated alkyne compound (such as butyne), the halogenated alkyne compound or olefin may polymerize (dimerize, etc.), the purity of the halogenated alkyne compound may decrease, or the container may become clogged.

[0019] The compositions containing the halogenated alkyne compounds of this disclosure suppress the decrease in purity during storage by adjusting the concentration of at least one component selected from the group consisting of halogenated ethylene compounds (olefins), oxygen, water, hydrogen fluoride, and hydrogen chloride.

[0020] The compositions containing the halogenated alkyne compounds of this disclosure suppress the decrease in purity of the halogenated alkyne compounds even during storage, and prevent container clogging.

[0021] (1-1) A composition containing the halogenated alkyne compound of the present disclosure is (1) General formula (1): R 1 -C≡CR 2 The composition contains a halogenated alkyne compound represented by (2) General formula (2): CF2=CFX, and the content of the halogenated ethylene compound represented by (2) General formula (2) is 1 ppm or more and 100 ppm or less by volume relative to the total amount of the composition.

[0022] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 X represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom. In general formula (2), X represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom.

[0023] A composition containing the halogenated alkyne compound of the present disclosure preferably contains, with respect to the total amount of the halogenated alkyne compound represented by (1) general formula (1), 95% to 99.9999% by volume.

[0024] (1-2) A composition containing the halogenated alkyne compound of the present disclosure is (1) General formula (1): R1 -C≡CR 2 The composition contains a halogenated alkyne compound represented by (1) and (2) oxygen, wherein the content of (2) oxygen is 0.1 ppm by volume or more and 100 ppm by volume or less relative to the total amount of the composition.

[0025] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom.

[0026] A composition containing the halogenated alkyne compound of the present disclosure preferably contains, with respect to the total amount of the halogenated alkyne compound represented by (1) general formula (1), 95% to 99.9999% by volume.

[0027] (1-3) Compositions containing the halogenated alkyne compounds of this disclosure include: (1) General formula (1): R 1 -C≡CR 2 The composition contains (1) a halogenated alkyne compound represented by (2) and (3) water, wherein the amount of (2) water relative to the total amount of the composition is 0.1 ppm by volume or more and 200 ppm by volume or less.

[0028] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom.

[0029] A composition containing the halogenated alkyne compound of the present disclosure preferably contains, with respect to the total amount of the halogenated alkyne compound represented by (1) general formula (1), 95% to 99.9999% by volume.

[0030] (1-4) The compositions containing the halogenated alkyne compounds of this disclosure suppress the decrease in purity of the halogenated alkyne compounds even during storage, and suppress container clogging.

[0031] The compositions containing the halogenated alkyne compounds of this disclosure include: (1) General formula (1): R 1 -C≡CR 2The composition contains a halogenated alkyne compound represented by (1) and (2) hydrogen fluoride, wherein the content of (2) hydrogen fluoride is 0.1 ppm by volume or more and 10 ppm by volume or less relative to the total amount of the composition.

[0032] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom.

[0033] A composition containing the halogenated alkyne compound of the present disclosure preferably contains, with respect to the total amount of the halogenated alkyne compound represented by (1) general formula (1), 95% to 99.9999% by volume.

[0034] (1-5) Compositions containing the halogenated alkyne compounds of this disclosure include: (1) General formula (1): R 1 -C≡CR 2 The composition contains a halogenated alkyne compound represented by (1) and (2) hydrogen chloride, wherein the content of (2) hydrogen chloride is 0.1 ppm by volume or more and 10 ppm by volume or less relative to the total amount of the composition.

[0035] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom.

[0036] A composition containing the halogenated alkyne compound of the present disclosure preferably contains, with respect to the total amount of the halogenated alkyne compound represented by (1) general formula (1), 95% to 99.9999% by volume.

[0037] This disclosure provides a method for stably transporting compositions containing a halogenated alkyne compound and at least one component selected from the group consisting of halogenated ethylene compounds, oxygen, water, hydrogen fluoride, and hydrogen chloride. According to this disclosure, by adjusting the content (concentration) of at least one component selected from the group consisting of halogenated ethylene compounds, oxygen, water, hydrogen fluoride, and hydrogen chloride in a composition containing a halogenated alkyne compound, polymerization or decomposition of the halogenated alkyne compound can be suppressed when transporting the composition in a cylinder or the like. This suppresses a decrease in the purity of the halogenated alkyne compound and maintains the storage stability of the composition containing the halogenated alkyne compound.

[0038] The compositions containing the halogenated alkyne compounds of this disclosure contain at least one component selected from the group consisting of halogenated ethylene compounds, oxygen, water, hydrogen fluoride, and hydrogen chloride, and have improved storage stability. Even under harsh conditions in maritime transport such as containers (e.g., temperature rise during transport), polymerization or decomposition of the halogenated alkyne compounds is suppressed, thereby enabling the stable transport of compositions containing halogenated alkyne compounds.

[0039] (1) Alkyne halide compounds A composition containing the alkyne halide compounds of this disclosure comprises, as the first component, (1) General formula (1): R 1 -C≡CR 2 It contains a halogenated alkyne compound represented by [formula].

[0040] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom (H), or a fluorine atom (F).

[0041] A perfluoroalkyl group is an alkyl group in which all hydrogen atoms are replaced by fluorine atoms.

[0042] The perfluoroalkyl group is preferably a perfluoroalkyl group having 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, even more preferably 1 to 4 carbon atoms, particularly preferably 1 to 3 carbon atoms, and most preferably 1 to 2 carbon atoms (CF3-, C2F5-).

[0043] The perfluoroalkyl group is preferably a linear or branched perfluoroalkyl group. The perfluoroalkyl group is preferably a trifluoromethyl group (CF3-), a pentafluoroethyl group (C2F5-:CF3-CF2-), a linear heptafluoropropyl group (C3F7-:CF3-CF2-CF2-), a branched heptafluoroisopropyl group (C3F7-:CF3-CF(CF3)-), a linear pentafluoropropenyl group (C3F5-:CF3-CF=CF-), a branched pentafluoroisopropenyl group (C3F5-:CF2=C(CF3)-), a linear nonafluorobutyl group (C4F9-:CF3-CF2-CF2-CF2-), a branched nonafluorosec-butyl group (C4F9-:CF3-CF2-CF(CF3)-), (Branched chain) nonafluoro-tert-butyl group (C4F9-:CF3-C(CF3)2-), etc.

[0044] (1) The number of carbon atoms in the halide alkyne compound is preferably 3 to 8, more preferably 3 to 6, even more preferably 3 to 5, and particularly preferably 4.

[0045] (1) The halide alkyne compound is preferably 1,1,1,4,4,4-hexafluoro-2-butyne (CF3C≡CCF3).

[0046] A composition containing a halogenated alkyne compound may (1) use one halogenated alkyne compound alone, or use two or more types mixed (blended).

[0047] Preferably, the composition containing a halogenated alkyne compound has a content of (1) the halogenated alkyne compound (or the total amount of halogenated alkyne compounds if the composition contains one or more halogenated alkyne compounds) of 95% to 99.9999% by volume, relative to the total volume of the composition.

[0048] A composition containing a halogenated alkyne compound contains the first component (1) a halogenated alkyne compound as the main component.

[0049] In a composition containing a halogenated alkyne compound, from the viewpoint of suppressing the formation of polymers (dimerization, etc.) or decomposition products of the halogenated alkyne compound even during storage of the composition containing the halogenated alkyne compound, the content of the halogenated alkyne compound in relation to the total amount of the composition is preferably, in order, 95% to 99.9999% by volume, 96% to 99.9997% by volume, 97% to 99.9995% by volume, more preferably, 95% to 99.999% by volume, 97% to 99.995% by volume, 97% to 99.9995% by volume, even more preferably, 98% to 99.9990% by volume, 98% to 99.990% by volume, and particularly preferably, 99% to 99.9985% by volume, and 99% to 99.985% by volume.

[0050] (2) At least one component selected from the group consisting of halogenated ethylene compounds, oxygen, water, hydrogen fluoride, and hydrogen chloride.

[0051] (2-1) Halide ethylene compounds A composition containing the halide alkyne compound of the present disclosure contains as a second component (2) a halide ethylene compound represented by general formula (2): CF2=CFX.

[0052] In general formula (2), X represents a hydrogen atom (H), a chlorine atom (Cl), a bromine atom (Br), or an iodine atom (I).

[0053] In a composition containing a halogenated alkyne compound, the content of (2) halogenated ethylene compounds (or the total amount of halogenated ethylene compounds if the composition contains one or more halogenated ethylene compounds) is between 1 volume ppm and 100 volume ppm.

[0054] From the viewpoint of suppressing the formation of polymers (dimerization, etc.) or decomposition products of the alkyne compound even during storage of the composition containing the alkyne compound, the halogenated ethylene compound is more preferably at least one halogenated ethylene compound selected from the group consisting of chlorotrifluoroethylene (CTFE) and bromotrifluoroethylene (BTFE), and even more preferably chlorotrifluoroethylene (CTFE).

[0055] The composition containing the halide alkyne compound may use (2) a halide ethylene compound alone, or a mixture (blend) of two or more types.

[0056] The composition containing a halogenated alkyne compound has a content of (2) a halogenated ethylene compound represented by general formula (2) relative to the total amount of the composition (when the halogenated ethylene compound is one type or two or more types, the total amount of the halogenated ethylene compound) of 1 volume ppm or more and 100 volume ppm or less, more preferably 2 volume ppm to 99 volume ppm, even more preferably 3 volume ppm to 98 volume ppm, and particularly preferably 4 volume ppm to 97 volume ppm.

[0057] The compositions containing the halogenated alkyne compounds of this disclosure can suppress the formation of polymers (dimers, etc.) or decomposition products of the halogenated alkyne compounds even during storage by adjusting the concentration of the halogenated ethylene compound (olefin compound).

[0058] The compositions containing the halogenated alkyne compounds of this disclosure exhibit suppressed degradation of the purity of the halogenated alkyne compounds even during storage, and can prevent clogging of the storage container.

[0059] (2-2) A composition containing the halogenated alkyne compound of the present disclosure contains (2) oxygen (O2) as a second component.

[0060] A composition containing a halogenated alkyne compound has an oxygen content of 0.1 volume ppm or more and 100 volume ppm or less relative to the total amount of the composition.

[0061] The composition containing the halide alkyne compound has an oxygen content of 0.1 volume ppm or more and 100 volume ppm or less relative to the total amount of the composition, more preferably 0.3 volume ppm to 75 volume ppm, even more preferably 0.6 volume ppm to 50 volume ppm, and particularly preferably 1 volume ppm to 15 volume ppm.

[0062] The composition containing the halogenated alkyne compound of this disclosure can suppress the formation of polymers (such as dimers) or decomposition products of the halogenated alkyne compound during storage by adjusting the oxygen concentration.

[0063] The compositions containing the halogenated alkyne compounds of this disclosure exhibit suppressed degradation of the purity of the halogenated alkyne compounds even during storage, and can prevent clogging of the storage container.

[0064] (2-3) Water A composition containing the halogenated alkyne compound disclosed herein contains (2) water as a second component.

[0065] A composition containing a halogenated alkyne compound shall have a water content of 0.1 volume ppm or more and 200 volume ppm or less relative to the total amount of the composition.

[0066] The composition containing the halide alkyne compound has a water content of 0.1 volume ppm or more and 200 volume ppm or less relative to the total amount of the composition, more preferably 0.3 volume ppm to 170 volume ppm, even more preferably 0.5 volume ppm to 150 volume ppm, and particularly preferably 1 volume ppm to 100 volume ppm.

[0067] The composition containing the halogenated alkyne compound of this disclosure can suppress the formation of polymers (such as dimers) or decomposition products of the halogenated alkyne compound during storage by adjusting the concentration of water.

[0068] The compositions containing the halogenated alkyne compounds of this disclosure exhibit suppressed degradation of the purity of the halogenated alkyne compounds even during storage, and can prevent clogging of the storage container.

[0069] (2-4) Hydrogen fluoride A composition containing the halogenated alkyne compound of the present disclosure contains (2) hydrogen fluoride (HF) as a second component.

[0070] The composition containing the halide alkyne compound has a hydrogen fluoride content of 0.1 volume ppm or more and 10 volume ppm or less relative to the total amount of the composition.

[0071] The composition containing the halide alkyne compound has a hydrogen fluoride content of 0.1 volume ppm or more and 10 volume ppm or less relative to the total amount of the composition, more preferably 0.3 volume ppm to 7.5 volume ppm, even more preferably 0.5 volume ppm to 6 volume ppm, and particularly preferably 1 volume ppm to 4 volume ppm.

[0072] The composition containing the halogenated alkyne compound of this disclosure can suppress the formation of polymers (such as dimers) or decomposition products of the halogenated alkyne compound even during storage by adjusting the concentration of hydrogen fluoride.

[0073] The compositions containing the halogenated alkyne compounds of this disclosure exhibit suppressed degradation of the purity of the halogenated alkyne compounds even during storage, and can prevent clogging of the storage container.

[0074] (2-5) Hydrogen chloride A composition containing the halogenated alkyne compound of this disclosure contains (2) hydrogen chloride (HCl) as a second component.

[0075] The composition containing the halide alkyne compound has a hydrogen chloride content of 0.1 volume ppm or more and 10 volume ppm or less relative to the total amount of the composition.

[0076] The composition containing the halogenated alkyne compound has a hydrogen chloride content of 0.1 volume ppm or more and 10 volume ppm or less relative to the total amount of the composition, more preferably 0.3 volume ppm to 7.5 volume ppm, even more preferably 0.5 volume ppm to 6 volume ppm, and particularly preferably 1 volume ppm to 4 volume ppm.

[0077] The composition containing the halogenated alkyne compound of this disclosure can suppress the formation of polymers (such as dimers) or decomposition products of the halogenated alkyne compound during storage by adjusting the concentration of hydrogen chloride.

[0078] The compositions containing the halogenated alkyne compounds of this disclosure exhibit suppressed degradation of the purity of the halogenated alkyne compounds even during storage, and can prevent clogging of the storage container.

[0079] [2] Method for preserving a composition containing a halogenated alkyne compound The method for preserving a composition containing a halogenated alkyne compound according to the present disclosure is as follows: (2-1a) The composition is (1) General formula (1): R 1 -C≡CR 2The composition contains a halogenated alkyne compound represented by (2) General formula (2): CF2=CFX, and the content of the halogenated ethylene compound represented by (2) General formula (2) is 1 ppm or more and 100 ppm or less by volume relative to the total amount of the composition.

[0080] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 X represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom. In general formula (2), X represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom.

[0081] A method for storing a composition containing the halogenated alkyne compound of this disclosure is preferably such that the content of the halogenated alkyne compound represented by (1) general formula (1) is 95% to 99.9999% by volume relative to the total amount of the composition.

[0082] In a composition containing a halogenated alkyne compound according to the present disclosure, a method for suppressing the decrease in purity of the halogenated alkyne compound is (2-1b) the composition is (1) General formula (1): R 1 -C≡CR 2 The composition contains a halogenated alkyne compound represented by (2) General formula (2): CF2=CFX, and the content of the halogenated ethylene compound represented by (2) General formula (2) is 1 ppm or more and 100 ppm or less by volume relative to the total amount of the composition.

[0083] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 X represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom. In general formula (2), X represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom.

[0084] In a composition containing the halogenated alkyne compound of this disclosure, a method for suppressing a decrease in the purity of the halogenated alkyne compound is preferably such that the content of the halogenated alkyne compound represented by (1) general formula (1) is 95% to 99.9999% by volume relative to the total amount of the composition.

[0085] In a method for preserving a composition containing a halogenated alkyne compound according to the present disclosure, (2-2a) the composition is (1) General formula (1): R 1 -C≡CR 2 The composition contains a halogenated alkyne compound represented by (1) and (2) oxygen, with the content of (2) oxygen being 0.1 ppm by volume or more and 100 ppm by volume or less relative to the total amount of the composition.

[0086] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom.

[0087] A method for storing a composition containing the halogenated alkyne compound of this disclosure is preferably such that the content of the halogenated alkyne compound represented by (1) general formula (1) is 95% to 99.9999% by volume relative to the total amount of the composition.

[0088] In a composition containing a halogenated alkyne compound of the present disclosure, a method for suppressing the decrease in purity of the halogenated alkyne compound is (2-2b) the composition is (1) General formula (1): R 1 -C≡CR 2 The composition contains a halogenated alkyne compound represented by (1) and (2) oxygen, with the content of (2) oxygen being 0.1 ppm by volume or more and 100 ppm by volume or less relative to the total amount of the composition.

[0089] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom.

[0090] In a composition containing the halogenated alkyne compound of this disclosure, a method for suppressing a decrease in the purity of the halogenated alkyne compound is preferably such that the content of the halogenated alkyne compound represented by (1) general formula (1) is 95% to 99.9999% by volume relative to the total amount of the composition.

[0091] In a method for preserving a composition containing a halogenated alkyne compound according to the present disclosure, (2-3a) the composition is (1) General formula (1): R 1 -C≡CR 2 The composition contains (1) a halogenated alkyne compound represented by (2) and (3) water, wherein the amount of (2) water relative to the total amount of the composition is 0.1 volume ppm or more and 200 volume ppm or less.

[0092] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom.

[0093] A method for storing a composition containing the halogenated alkyne compound of this disclosure is preferably such that the content of the halogenated alkyne compound represented by (1) general formula (1) is 95% to 99.9999% by volume relative to the total amount of the composition.

[0094] In a composition containing a halogenated alkyne compound of the present disclosure, a method for suppressing the decrease in purity of the halogenated alkyne compound is (2-3b) The composition is (1) General formula (1): R 1 -C≡CR 2 A method comprising (1) a halogenated alkyne compound represented by (2) and (3) water, wherein the content of (2) water is 0.1 volume ppm or more and 200 volume ppm or less relative to the total amount of the composition.

[0095] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom.

[0096] In a composition containing the halogenated alkyne compound of this disclosure, a method for suppressing a decrease in the purity of the halogenated alkyne compound is preferably such that the content of the halogenated alkyne compound represented by (1) general formula (1) is 95% to 99.9999% by volume relative to the total amount of the composition.

[0097] In a method for preserving a composition containing a halogenated alkyne compound according to the present disclosure, (2-4a) the composition is (1) General formula (1): R 1 -C≡CR 2 The composition contains a halogenated alkyne compound represented by (1) and (2) hydrogen fluoride, with the content of (2) hydrogen fluoride being 0.1 ppm by volume or more and 10 ppm by volume or less relative to the total amount of the composition.

[0098] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom.

[0099] A method for storing a composition containing the halogenated alkyne compound of this disclosure is preferably such that the content of the halogenated alkyne compound represented by (1) general formula (1) is 95% to 99.9999% by volume relative to the total amount of the composition.

[0100] In a composition containing a halogenated alkyne compound of the present disclosure, a method for suppressing the decrease in purity of the halogenated alkyne compound is (2-4b) The composition is (1) General formula (1): R 1 -C≡CR 2 The composition contains a halogenated alkyne compound represented by (1) and (2) hydrogen fluoride, with the content of (2) hydrogen fluoride being 0.1 ppm by volume or more and 10 ppm by volume or less relative to the total amount of the composition.

[0101] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom.

[0102] In a composition containing the halogenated alkyne compound of this disclosure, a method for suppressing a decrease in the purity of the halogenated alkyne compound is preferably such that the content of the halogenated alkyne compound represented by (1) general formula (1) is 95% to 99.9999% by volume relative to the total amount of the composition.

[0103] In a method for preserving a composition containing a halogenated alkyne compound according to the present disclosure, (2-5a) the composition is (1) General formula (1): R 1 -C≡CR 2 The composition contains a halogenated alkyne compound represented by (1) and (2) hydrogen chloride, with the content of (2) hydrogen chloride being 0.1 ppm by volume or more and 10 ppm by volume or less relative to the total amount of the composition.

[0104] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom.

[0105] A method for storing a composition containing the halogenated alkyne compound of this disclosure is preferably such that the content of the halogenated alkyne compound represented by (1) general formula (1) is 95% to 99.9999% by volume relative to the total amount of the composition.

[0106] In a composition containing a halogenated alkyne compound of the present disclosure, a method for suppressing the decrease in purity of the halogenated alkyne compound is (2-5b) the composition is (1) General formula (1): R 1 -C≡CR 2 The composition contains a halogenated alkyne compound represented by (1) and (2) hydrogen chloride, with the content of (2) hydrogen chloride being 0.1 ppm by volume or more and 10 ppm by volume or less relative to the total amount of the composition.

[0107] In general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom.

[0108] In a composition containing the halogenated alkyne compound of this disclosure, a method for suppressing a decrease in the purity of the halogenated alkyne compound is preferably such that the content of the halogenated alkyne compound represented by (1) general formula (1) is 95% to 99.9999% by volume relative to the total amount of the composition.

[0109] In the method for preserving a composition containing a halogenated alkyne compound of this disclosure, and in the method for suppressing a decrease in the purity of a halogenated alkyne compound in a composition containing a halogenated alkyne compound, the details of the components, content, etc. of the composition containing the halogenated alkyne compound are as described above in [1] Composition containing a halogenated alkyne compound.

[0110] A method for storing a composition containing a halogenated alkyne compound according to this disclosure, and a method for suppressing the decrease in purity of a halogenated alkyne compound in a composition containing a halogenated alkyne compound, involves adjusting the concentration of at least one component selected from the group consisting of halogenated ethylene compounds (olefin compounds), oxygen (O2), water, hydrogen fluoride (HF), and hydrogen chloride (HCl) in the composition containing the halogenated alkyne compound, thereby suppressing the formation of polymers (dimers, etc.) or decomposition products of the halogenated alkyne compound even during storage.

[0111] By the method for storing a composition containing a halogenated alkyne compound and the method for suppressing the decrease in purity of the halogenated alkyne compound in a composition containing a halogenated alkyne compound, the decrease in purity of the halogenated alkyne compound is suppressed even during storage, and the blockage of the storage container can be suppressed.

[0112] The compositions containing the halogenated alkyne compounds of this disclosure exhibit good storage stability when transported in cylinders or the like.

[0113] The compositions containing the halogenated alkyne compounds of this disclosure have improved storage stability, and even under harsh conditions in maritime transport such as containers (e.g., temperature increases during transport), polymerization or decomposition of the halogenated alkyne compounds is suppressed, thereby enabling the stable transport of compositions containing halogenated alkyne compounds.

[0114] [3] Uses of compositions containing halogenated alkyne compounds The compositions containing halogenated alkyne compounds of this disclosure are preferably used as etching gases, refrigerants, heat transfer media, deposit gases, building blocks for organic synthesis, or cleaning gases.

[0115] The compositions containing the halogenated alkyne compounds of this disclosure are preferably used as etching gases, refrigerants, heat transfer media, etc., for forming cutting-edge microstructures such as semiconductors and liquid crystals. The compositions can preferably be effectively used in various applications such as deposit gases, building blocks for organic synthesis, and cleaning gases.

[0116] Deposit gas is a gas used to deposit an etching-resistant polymer layer.

[0117] Building blocks for organic synthesis refer to substances that can serve as precursors for compounds with highly reactive skeletons. (1) General formula (1): R 1 -C≡CR 2 When a composition containing a halogenated alkyne compound represented by [the formula shown] is reacted with a fluorine-containing organosilicon compound such as CF3Si(CH3)3, it is possible to introduce fluoroalkyl groups such as CF3 groups and convert it into a substance that can be used as a detergent or a fluorine-containing pharmaceutical intermediate.

[0118] Etching can be performed on a semiconductor manufacturing substrate using a composition containing the halide alkyne compound of this disclosure as an etching gas, which is supplied as a gas to generate plasma.

[0119] A gas plasma containing a halide alkyne compound (etching gas) can be used to etch silicon-based materials on which a silicon oxide film (SiO2 film) or silicon nitride film (SiN film) has been formed. The silicon-based material to be etched is preferably a semiconductor manufacturing substrate.

[0120] By using a composition containing a halide alkyne compound, hole etching can be performed on silicon-based materials containing a silicon oxide film (SiO2 film) or a silicon nitride film (SiN film) using the generated gas plasma, resulting in etching that maintains the processed shape of the holes well. The etching method (especially the dry etching method) can be the same as that of conventional methods.

[0121] The present invention will be described in detail below using examples and comparative examples. However, the present invention is not limited to these.

[0122] [1] Storage stability of compositions containing halogenated alkyne compounds (Example 1) Second component: halogenated ethylene compound (1) Storage stability test Composition containing halogenated alkyne compound (1) General formula (1): R 1 -C≡CR 2 In the general formula (1) of the halide alkyne compound represented by R, 1 is, and R 2 These are listed in Table 1. (2) General formula (2): Halogenated ethylene compounds represented by CF2=CFX: Chlorotrifluoroethylene (CTFE) Bromotrifluoroethylene (BTFE)

[0123] A composition containing a halogenated alkyne compound was prepared by mixing (1) a halogenated alkyne compound with (2) a halogenated ethylene compound adjusted to a predetermined concentration using a conventional method.

[0124] The compositions containing the halogenated alkyne compounds of the examples contain (2) halogenated ethylene compounds in an amount of 1 volume ppm or more and 100 volume ppm or less, relative to the total amount of the composition.

[0125] In the composition containing the halide alkyne compound, the concentration (volume ppm) of the halide ethylene compound was analyzed by gas chromatography (GC analysis).

[0126] A composition containing a halogenated alkyne compound was stored at a constant temperature (25°C), and after a certain period (1 month), the gas phase was extracted, and (1) the halogenated alkyne compound and / or (2) polymers and / or decomposition products derived from the halogenated ethylene compound were subjected to GC analysis (volume ppm).

[0127]

[0128] (1) Alkyne halide compounds: R 1 -C≡CR 2 R 1 CF3-: Trifluoromethyl group, C2F5-: Pentafluoroethyl group R 2 CF3-: Trifluoromethyl group, C2F5-: Pentafluoroethyl group H: Hydrogen atom, F: Fluorine atom (2) Halide ethylene compounds CTFE: Chlorotrifluoroethylene BTFE: Bromotrifluoroethylene ND: Not detected

[0129] (2) Evaluation results of storage stability The compositions containing halogenated alkyne compounds in the examples were able to suppress the formation of polymers (dimers, etc.) or decomposition products of the halogenated alkyne compounds within an acceptable range during storage (25°C, 1 month) compared to the comparative example where the concentration deviated from the norm, by adjusting the concentration of halogenated ethylene compounds (olefin compounds) to 100 ppm or less by volume relative to the total amount of the composition.

[0130] The compositions containing the halogenated alkyne compounds of the examples exhibit suppressed degradation of the purity of the halogenated alkyne compounds even during storage, and can prevent clogging of the storage container.

[0131] (Example 2) Second component: Oxygen (O2) (1) Storage stability test Composition containing a halogenated alkyne compound (1) General formula (1): R 1 -C≡CR 2An alkyne halide compound represented by R 1 CF3-: Trifluoromethyl group R 2 CF3-: Trifluoromethyl group 1,1,1,4,4,4-hexafluoro-2-butyne (CF3C≡CCF3)

[0132] According to a conventional method, (1) an alkyne halide compound and (2) oxygen adjusted to a predetermined concentration were mixed to prepare a composition containing the alkyne halide compound.

[0133] The composition containing the alkyne halide compound of the example contains (2) oxygen at 0.1 volume ppm or more and 100 volume ppm or less based on the total amount of the composition.

[0134] In the composition containing the alkyne halide compound, the concentration (volume ppm) of (2) oxygen was analyzed by gas chromatography (GC analysis).

[0135] The composition containing the alkyne halide compound was stored at a constant temperature (25 °C or 50 °C), and after a certain period (1 month) had elapsed, the gas phase was extracted, and (1) polymers and / or decomposition products derived from the alkyne halide compound, and hydrogen fluoride (HF) generated during the formation of these polymers and / or decomposition products were analyzed by GC (volume ppm).

[0136]

[0137] ND: Not Detected

[0138] (2) Evaluation results of storage stability The composition containing the alkyne halide compound of the example was able to suppress the formation of polymers (dimerization, etc.) or decomposition products of the alkyne halide compound within an acceptable range during storage (25 °C, or 50 °C, 1 month) by adjusting the concentration of oxygen to 0.1 volume ppm or more and 100 volume ppm or less.

[0139] The composition containing the alkyne halide compound of the example also suppresses the decrease in the purity of the alkyne halide compound during storage and can suppress the clogging of the container during storage.

[0140] (Example 3) Second component: Water (1) Storage stability test Composition containing a halogenated alkyne compound (1) General formula (1): R 1 -C≡CR 2 Alkyne halogen compounds represented by R 1 CF3-: Trifluoromethyl group R 2 CF3-: Trifluoromethyl group 1,1,1,4,4,4-Hexafluoro-2-butyne (CF3C≡CCF3)

[0141] A composition containing a halogenated alkyne compound was prepared by mixing (1) a halogenated alkyne compound with (2) water adjusted to a predetermined concentration using a conventional method.

[0142] The compositions containing the halogenated alkyne compounds of the examples contain (2) water in an amount of 0.1 volume ppm or more and 200 volume ppm or less, relative to the total amount of the composition.

[0143] In the composition containing the halide alkyne compound, (2) the concentration of water (volume ppm) was analyzed by gas chromatography (GC analysis).

[0144] A composition containing a halogenated alkyne compound was stored at a constant temperature (25°C, 40°C, or 60°C), and after a certain period (1 month), the gas phase was extracted, and (1) polymers and / or decomposition products derived from the halogenated alkyne compound, and hydrogen fluoride (HF) produced during the formation of these polymers and / or decomposition products were subjected to GC analysis (volume ppm).

[0145]

[0146] ND: Not Detected

[0147] (2) Evaluation results of storage stability The compositions containing the halogenated alkyne compound of the example were able to suppress the formation of polymers (dimerization, etc.) or decomposition products of the halogenated alkyne compound within an acceptable range during storage (25°C, 40°C, or 60°C, after 1 month) by adjusting the water concentration to 0.1 volume ppm or more and 200 volume ppm or less relative to the total amount of the composition, compared to the comparative example where the concentration deviated.

[0148] The composition containing the halogenated alkyne compound of the example suppresses the decrease in the purity of the halogenated alkyne compound during storage and can suppress the clogging of the container during storage.

[0149] (Example 4) Second component: hydrogen fluoride (HF) (1) Test of storage stability Composition containing a halogenated alkyne compound (1) General formula (1): R 1 -C≡C-R 2 Halogenated alkyne compound represented by R 1 CF3-: trifluoromethyl group R 2 CF3-: trifluoromethyl group 1,1,1,4,4,4-hexafluoro-2-butyne (CF3C≡CCF3)

[0150] According to a conventional method, (1) a halogenated alkyne compound and (2) hydrogen fluoride adjusted to a predetermined concentration were mixed to prepare a composition containing the halogenated alkyne compound.

[0151] The composition containing the halogenated alkyne compound of the example contains (2) hydrogen fluoride (HF) at 0.1 volume ppm or more and 10 volume ppm or less based on the total amount of the composition.

[0152] In the composition containing the halogenated alkyne compound, the concentration (volume ppm) of (2) hydrogen fluoride was analyzed by Fourier transform infrared spectroscopy (FT-IR analysis).

[0153] The composition containing the halogenated alkyne compound was stored at a constant temperature (25 °C or 50 °C). After a certain period (1 month) elapsed, the gas phase was extracted, and (1) the polymer and / or decomposition product derived from the halogenated alkyne compound was analyzed by GC (volume ppm).

[0154]

[0155] ND: Not Detected

[0156] (2) Evaluation results of storage stability: By adjusting the concentration of hydrogen fluoride in the halogenated alkyne compound compositions of the examples to 0.1 volume ppm or more and 10 volume ppm or less relative to the total amount of the composition, the formation of polymers (dimerization, etc.) or decomposition products of the halogenated alkyne compound during storage was suppressed to an acceptable range compared to the comparative example where the concentration deviated.

[0157] The compositions containing the halogenated alkyne compounds of the examples show suppressed degradation of the purity of the halogenated alkyne compounds even during storage (25°C or 50°C, after 1 month), and can prevent clogging of the storage container.

[0158] (Example 5) Second component: Hydrogen chloride (HCl) (1) Storage stability test Composition containing a halogenated alkyne compound (1) General formula (1): R 1 -C≡CR 2 Alkyne halogen compounds represented by R 1 CF3-: Trifluoromethyl group R 2 CF3-: Trifluoromethyl group 1,1,1,4,4,4-Hexafluoro-2-butyne (CF3C≡CCF3)

[0159] A composition containing a halogenated alkyne compound was prepared by mixing (1) a halogenated alkyne compound with (2) hydrogen chloride adjusted to a predetermined concentration using a conventional method.

[0160] The compositions containing the halogenated alkyne compounds of the examples contain (2) hydrogen chloride (HCl) in an amount of 0.1 volume ppm or more and 10 volume ppm or less, relative to the total amount of the composition.

[0161] In the composition containing the halide alkyne compound, (2) the concentration (volume ppm) of hydrogen chloride was analyzed by gas chromatography (GC analysis).

[0162] A composition containing a halogenated alkyne compound was stored at a constant temperature (25°C or 50°C), and after a certain period (1 month), the gas phase was extracted, and (1) polymers and / or decomposition products derived from the halogenated alkyne compound were subjected to GC analysis (volume ppm).

[0163]

[0164] ND: Not Detected

[0165] (2) Evaluation results of storage stability The compositions containing halogenated alkyne compounds in the examples were able to suppress the formation of polymers (dimerization, etc.) or decomposition products of the halogenated alkyne compounds within an acceptable range during storage (25°C or 50°C, 1 month) by adjusting the concentration of hydrogen chloride to 0.1 volume ppm or more and 10 volume ppm or less relative to the total amount of the composition, compared to the comparative example where the concentration deviated.

[0166] The compositions containing the halogenated alkyne compounds of the examples show suppressed degradation of the purity of the halogenated alkyne compounds even during storage (25°C or 50°C, after 1 month), and can prevent clogging of the storage container.

[0167] [2] Industrial applicability Compositions containing the halogenated alkyne compounds of this disclosure can suppress the formation of polymers (dimers, etc.) or decomposition products of the halogenated alkyne compounds even during storage by adjusting the concentration of at least one component selected from the group consisting of halogenated ethylene compounds (olefin compounds), oxygen, water, hydrogen fluoride, and hydrogen chloride.

[0168] The compositions containing the halogenated alkyne compounds of this disclosure exhibit suppressed degradation of the purity of the halogenated alkyne compounds even during storage, and can prevent clogging of the storage container.

[0169] In a composition containing a halogenated alkyne compound according to this disclosure, by adjusting the content (concentration) of at least one component selected from the group consisting of halogenated ethylene compounds, oxygen, water, hydrogen fluoride, and hydrogen chloride, polymerization or decomposition of the halogenated alkyne compound can be suppressed when the composition containing the halogenated alkyne compound is transported in a cylinder or the like. This suppresses a decrease in the purity of the halogenated alkyne compound and maintains the storage stability of the composition containing the halogenated alkyne compound.

[0170] The compositions containing the halogenated alkyne compounds of this disclosure contain at least one component selected from the group consisting of halogenated ethylene compounds, oxygen, water, hydrogen fluoride, and hydrogen chloride, and have improved storage stability. Even under harsh conditions in maritime transport such as containers (e.g., temperature rise during transport), polymerization or decomposition of the halogenated alkyne compounds is suppressed, thereby enabling the stable transport of compositions containing halogenated alkyne compounds.

Claims

1. A composition containing a halogenated alkyne compound, wherein the composition comprises (1) general formula (1): R 1 -C≡CR 2 Alkyne halide compounds represented by (in general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom. ) (2) (2-1) A halogenated ethylene compound represented by general formula (2): CF2=CFX, (wherein general formula (2), X represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom.) (2-2) Oxygen, (2-3) Water, (2-4) Hydrogen fluoride, and (2-5) Hydrogen chloride, wherein, with respect to the total amount of the composition, (2) when the composition contains (2-1) the halogenated ethylene compound represented by general formula (2), the content of the halogenated ethylene compound represented by general formula (2) is 1 ppm by volume or more and 100 ppm by volume, when the composition contains (2-2) the oxygen, the content of the oxygen is 0.1 ppm by volume or more and 100 ppm by volume, and when the composition contains (2-3) the water, the content of the water is 0.1 ppm by volume or more and 200 ppm by volume. A composition in which (2-4) when it contains hydrogen fluoride, the content of hydrogen fluoride is 0.1 ppm by volume or more and 10 ppm by volume or less, or (2-5) when it contains hydrogen chloride, the content of hydrogen chloride is 0.1 ppm by volume or more and 10 ppm by volume or less.

2. The composition according to claim 1, wherein the content of the halogenated alkyne compound represented by general formula (1) is 95% to 99.9999% by volume, relative to the total amount of the composition.

3. A method for preserving a composition containing a halogenated alkyne compound, wherein the composition is (1) General formula (1): R 1 -C≡CR 2 Alkyne halide compounds represented by (in general formula (1), R 1 R represents a perfluoroalkyl group. In general formula (1), R 2 This represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom. ) (2) (2-1) A halogenated ethylene compound represented by general formula (2): CF2=CFX, (wherein general formula (2), X represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom.) (2-2) Oxygen, (2-3) Water, (2-4) Hydrogen fluoride, and (2-5) Hydrogen chloride, and the composition contains, with respect to the total amount of the composition, (2) when the composition contains the halogenated ethylene compound represented by general formula (2), the content of the halogenated ethylene compound represented by general formula (2) shall be 1 ppm by volume or more and 100 ppm by volume, when the composition contains the oxygen, the content of the oxygen shall be 0.1 ppm by volume or more and 100 ppm by volume, and when the composition contains the water, the content of the water shall be 0.1 ppm by volume or more and 200 ppm by volume. A method comprising: (2-4) when the composition contains the hydrogen fluoride, the content of the hydrogen fluoride being 0.1 ppm by volume or more and 10 ppm by volume or less; or (2-5) when the composition contains the hydrogen chloride, the content of the hydrogen chloride being 0.1 ppm by volume or more and 10 ppm by volume or less.

4. The method according to claim 3, wherein the content of the halogenated alkyne compound represented by general formula (1) above is 95% to 99.9999% by volume, relative to the total amount of the composition.

5. A method for suppressing the purity reduction of an alkynyl halide compound in a composition containing an alkynyl halide compound, wherein the composition comprises: (1) an alkynyl halide compound represented by the general formula (1): R 1 -C≡C-R 2 (wherein in the general formula (1), R 1 represents a perfluoroalkyl group; in the general formula (1), R 2 represents a perfluoroalkyl group, a hydrogen atom, or a fluorine atom); (2) at least one component selected from the group consisting of: (2-1) a halogenated ethylene compound represented by the general formula (2): CF2=CFX (wherein in the general formula (2), X represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom); (2-2) oxygen; (2-3) water; (2-4) hydrogen fluoride; and (2-5) hydrogen chloride. When the composition contains (2-1) the halogenated ethylene compound represented by the general formula (2), the content of the halogenated ethylene compound represented by the general formula (2) is 1 volume ppm or more and 100 volume ppm or less; when the composition contains (2-2) the oxygen, the content of the oxygen is 0.1 volume ppm or more and 100 volume ppm or less; when the composition contains (2-3) the water, the content of the water is 0.1 volume ppm or more and 200 volume ppm or less; when the composition contains (2-4) the hydrogen fluoride, the content of the hydrogen fluoride is 0.1 volume ppm or more and 10 volume ppm or less; or when the composition contains (2-5) the hydrogen chloride, the content of the hydrogen chloride is 0.1 volume ppm or more and 10 volume ppm or less, based on the total amount of the composition.

6. The method according to claim 5, wherein the content of the halogenated alkyne compound represented by general formula (1) is 95% to 99.9999% by volume, relative to the total amount of the composition.

Images