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.

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.

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.

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.

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.

There are provided a solvent composition which is excellent in solubility of various organic substances and excellent in detergency and a drying property, and has no adverse effect on a global environment and is excellent in stability; a cleaning method using the solvent composition; a method of forming a coating film; a heat transfer fluid including the solvent composition; and a heat cycle system using the heat transfer fluid. A solvent composition including 1-chloro-2,3,3-trifluoro-1-propene and 1-chloro-3,3-difluoro-1-propyne, a cleaning method of bringing the solvent composition and an article into contact with each other, a method of dissolving a nonvolatile organic compound in the solvent composition to produce a coating film-forming composition and evaporating the solvent composition after applying the coating film-forming composition on an article to be coated, to form a coating film, a heat transfer fluid including the solvent composition, and a heat cycle system using the heat transfer fluid.

There are provided a solvent composition which is excellent in solubility of various organic substances and excellent in detergency and a drying property, and has no adverse effect on a global environment and is excellent in stability; a cleaning method using the solvent composition; a method of forming a coating film; a heat transfer fluid including the solvent composition; and a heat cycle system using the heat transfer fluid. A solvent composition including 1-chloro-2,3,3-trifluoro-1-propene and 1-chloro-3,3-difluoro-1-propyne, a cleaning method of bringing the solvent composition and an article into contact with each other, a method of dissolving a nonvolatile organic compound in the solvent composition to produce a coating film-forming composition and evaporating the solvent composition after applying the coating film-forming composition on an article to be coated, to form a coating film, a heat transfer fluid including the solvent composition, and a heat cycle system using the heat transfer fluid.

A plasma etching method according to an embodiment is a method for etching a silicon-containing film by using plasma of a fluorocarbon gas. The fluorocarbon gas includes at least one selected from a first fluorocarbon which has a main chain of six or more carbons bonded in a linear manner, the main chain having a structure of single bond and double bond alternately joined, a second fluorocarbon which has a main chain of six or more carbons bonded in a linear manner, the main chain having a structure of single bond and triple bond alternately joined, and a third fluorocarbon which has a main chain of five or more carbons bonded in a linear manner, the main chain having a structure which includes double bond and triple bond.

A plasma etching method according to an embodiment is a method for etching a silicon-containing film by using plasma of a fluorocarbon gas. The fluorocarbon gas includes at least one selected from a first fluorocarbon which has a main chain of six or more carbons bonded in a linear manner, the main chain having a structure of single bond and double bond alternately joined, a second fluorocarbon which has a main chain of six or more carbons bonded in a linear manner, the main chain having a structure of single bond and triple bond alternately joined, and a third fluorocarbon which has a main chain of five or more carbons bonded in a linear manner, the main chain having a structure which includes double bond and triple bond.

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 %.