Heterogenous azeotrope or azeotrope-like compositions comprising 3,3,3-trifluoropropyne (TFPY) and hydrogen fluoride (HF) which may include from about 71.5 wt. % to about 98.8 wt. % 3,3,3-trifluoropropyne (TFPY) and from about 1.2 wt. % to about 28.5 wt. % hydrogen fluoride and have a boiling point between about −10.0° C. and about 25.0° C. at a pressure of between about 61 psia and about 171 psia. The azeotrope or azeotrope-like compositions may be used to separate 3,3,3-trifluoropropyne (TFPY) as an impurity from compositions of 2-chloro-3,3,3-trifluoropropene (1233xf), 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb), or 2,3,3,3-tetrafluoropropene (HFO-1234yf).

A method of producing (Z)-1,1,1,4,4,4-hexafluoro-2-butene (Z-1336mzz) is described. The method utilizes readily available halogenated starting materials, including 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) and carbon tetrachloride.

A method of producing (Z)-1,1,1,4,4,4-hexafluoro-2-butene (Z-1336mzz) is described. The method utilizes readily available halogenated starting materials, including 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) and carbon tetrachloride.

Provided are a method for efficiently producing an asymmetric conjugated diyne from an inexpensive and safe alternative compound to hydroxylamine hydrochloride and a method for producing a Z,Z-conjugated diene compound from the asymmetric conjugated diyne compound thus obtained. More specifically, provided is a method for producing an asymmetric conjugated diyne compound comprising a step of subjecting a terminal alkyne compound (1): HC≡C—Z.sup.1—Y.sup.1 to a coupling reaction with an alkynyl halide (2): Y.sup.2—Z.sup.2—C≡C—X by using sodium borohydride in water and an organic solvent in the presence of a copper catalyst and a base to obtain the asymmetric conjugated diyne compound (3): Y.sup.2—Z.sup.2—C≡C—C≡C—Z.sup.1—Y.sup.1. In addition, provided is a method for producing a Z,Z-conjugated diene compound by reducing the resulting asymmetric conjugated diyne compound, or the like.

Provided are a method for efficiently producing an asymmetric conjugated diyne from an inexpensive and safe alternative compound to hydroxylamine hydrochloride and a method for producing a Z,Z-conjugated diene compound from the asymmetric conjugated diyne compound thus obtained. More specifically, provided is a method for producing an asymmetric conjugated diyne compound comprising a step of subjecting a terminal alkyne compound (1): HC≡C—Z.sup.1—Y.sup.1 to a coupling reaction with an alkynyl halide (2): Y.sup.2—Z.sup.2—C≡C—X by using sodium borohydride in water and an organic solvent in the presence of a copper catalyst and a base to obtain the asymmetric conjugated diyne compound (3): Y.sup.2—Z.sup.2—C≡C—C≡C—Z.sup.1—Y.sup.1. In addition, provided is a method for producing a Z,Z-conjugated diene compound by reducing the resulting asymmetric conjugated diyne compound, or the like.

A cleaning method may include: bringing an article to be cleaned into contact with a liquid-phase solvent composition including 1-chloro-2,3,3-trifluoro-1-propene and 1-chloro-2,2,3,3-tetrafluoropropane; and exposing the article to be cleaned to steam generated by evaporating the liquid-phase solvent composition. In the liquid-phase composition, a proportion of a content of 1-chloro-2,2,3,3-tetrafluoropropane to a total of a content of 1-chloro-2,3,3-trifluoro-1-propene and a content of 1-chloro-2,2,3,3-tetrafluoropropane may be 0.0001 to 1 mass %.

A cleaning method may include: bringing an article to be cleaned into contact with a liquid-phase solvent composition including 1-chloro-2,3,3-trifluoro-1-propene and 1-chloro-2,2,3,3-tetrafluoropropane; and exposing the article to be cleaned to steam generated by evaporating the liquid-phase solvent composition. In the liquid-phase composition, a proportion of a content of 1-chloro-2,2,3,3-tetrafluoropropane to a total of a content of 1-chloro-2,3,3-trifluoro-1-propene and a content of 1-chloro-2,2,3,3-tetrafluoropropane may be 0.0001 to 1 mass %.

A process for the joint preparation of 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene, comprising: (a) starting materials comprising at least one compound having the structure of formula I, II or III is reacted with hydrogen fluoride, producing 1,2,3-trichloro-3,3-difluoropropene, 1,2,3-trichloro-1,1,2-trifluoropropane, and 1,2,3-trichloro-1,1,3-trifluoropropane; in the compounds of said formulae CF.sub.2−mCl.sub.m=CCl-CHF.sub.2−nCl.sub.n (Formula I), CF.sub.3−pCl.sub.pCHCl=CH.sub.2Cl (Formula II), and CF.sub.3−xCl.sub.xCF.sub.2−yCl.sub.yCHF.sub.2−zCl.sub.z (Formula III), m=0, 1, 2; n=1, 2; p=2, 3; x=1, 2, 3; y=1, 2; z=1, 2 and 4≦x+y+z≦6; (b) the 1,2,3-trichloro-3,3-difluoropropene, 1,2,3-trichloro-1,1,2-trifluoropropane and 1,2,3-trichloro-1,1,3-trifluoropropane undergo dechlorination, producing 3-chloro-3,3-difluoropropyne, 3-chloro-2,3,3-trifluoropropene and 3-chloro-1,3,3-trifluoropropene; and (c) the 3-chloro-3,3-difluoropropyne, 3-chloro-2,3,3-trifluoropropene and 3-chloro-1,3,3-trifluoropropene are reacted with hydrogen fluoride, simultaneously yielding 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropen.

FIG. 1 is designated as the drawing of the Abstract.

A process for the joint preparation of 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene, comprising: (a) starting materials comprising at least one compound having the structure of formula I, II or III is reacted with hydrogen fluoride, producing 1,2,3-trichloro-3,3-difluoropropene, 1,2,3-trichloro-1,1,2-trifluoropropane, and 1,2,3-trichloro-1,1,3-trifluoropropane; in the compounds of said formulae CF.sub.2−mCl.sub.m=CCl-CHF.sub.2−nCl.sub.n (Formula I), CF.sub.3−pCl.sub.pCHCl=CH.sub.2Cl (Formula II), and CF.sub.3−xCl.sub.xCF.sub.2−yCl.sub.yCHF.sub.2−zCl.sub.z (Formula III), m=0, 1, 2; n=1, 2; p=2, 3; x=1, 2, 3; y=1, 2; z=1, 2 and 4≦x+y+z≦6; (b) the 1,2,3-trichloro-3,3-difluoropropene, 1,2,3-trichloro-1,1,2-trifluoropropane and 1,2,3-trichloro-1,1,3-trifluoropropane undergo dechlorination, producing 3-chloro-3,3-difluoropropyne, 3-chloro-2,3,3-trifluoropropene and 3-chloro-1,3,3-trifluoropropene; and (c) the 3-chloro-3,3-difluoropropyne, 3-chloro-2,3,3-trifluoropropene and 3-chloro-1,3,3-trifluoropropene are reacted with hydrogen fluoride, simultaneously yielding 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropen.

FIG. 1 is designated as the drawing of the Abstract.

A halogenated alkene compound and a fluorinated alkyne compound are obtained at a high conversion rate and high selectivity by employing any of the following methods (1) to (4): (1) a halogenated butane compound represented by CX.sup.1X.sup.2X.sup.3CHX.sup.4CFHCX.sup.5X.sup.6X.sup.7, wherein X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, and X.sup.7 are the same or different and each is a halogen atom, to a dehydrofluorination reaction; (2) a halogenated butene compound represented by CX.sup.1X.sup.2X.sup.3CX.sup.4═CHCX.sup.5X.sup.6X.sup.7, wherein X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, and X.sup.7 are as defined above, to a dehydrohalogenation reaction; (3) a halogenated alkane compound represented by CHX.sup.8A.sup.1CHX.sup.9A.sup.2, wherein A.sup.1 and A.sup.2 are each a fluorine atom or a perfluoroalkyl group, and X.sup.8 and X.sup.9 are the same or different and each is a halogen atom, to a dehydrohalogenation reaction in the presence of a catalyst in a gas phase; and (4) a halogenated alkene compound represented by CX.sup.8A.sup.1=CHA.sup.2, wherein A.sup.1, A.sup.2, and X.sup.8 are as defined above, to a dehydrohalogenation reaction in the presence of a catalyst.