A process is provided comprising contacting and reacting the compound CF.sub.3CF.sub.2CHXCl, wherein X is H or Cl, or the compound CF.sub.3CF═CXCl, wherein X is H or Cl, with hydrogen in the presence of a catalyst consisting essentially of Cu, Ru, Cu—Pd, Ni—Cu, and Ni—Pd, to obtain as a result thereof reaction product comprising hydrofluoropropenes or intermediates convertible to said hydrofluoropropenes, notably CF.sub.3CF═CH.sub.2 and CF.sub.3CH═CHF.

A process is provided comprising contacting and reacting the compound CF.sub.3CF.sub.2CHXCl, wherein X is H or Cl, or the compound CF.sub.3CF═CXCl, wherein X is H or Cl, with hydrogen in the presence of a catalyst consisting essentially of Cu, Ru, Cu—Pd, Ni—Cu, and Ni—Pd, to obtain as a result thereof reaction product comprising hydrofluoropropenes or intermediates convertible to said hydrofluoropropenes, notably CF.sub.3CF═CH.sub.2 and CF.sub.3CH═CHF.

The present invention relates to a novel method for producing fluorinated cycloaliphatic compounds from the analogous aromatic compounds by hydrogenation with an Rh-carbene catalyst system.

The present invention relates to a novel method for producing fluorinated cycloaliphatic compounds from the analogous aromatic compounds by hydrogenation with an Rh-carbene catalyst system.

The present invention relates to a novel method for producing fluorinated cycloaliphatic compounds from the analogous aromatic compounds by hydrogenation with an Rh-carbene catalyst system.

Provided is a method for purifying a phosphorus-containing olefin compound salt as a raw material or an intermediate that is useful to increase the purity of a target product in a method for producing an olefin compound and that can be applied to the production method, and a method for producing an olefin compound using a purified product obtained thereby.

Specifically, provided is a method for purifying a phosphorus-containing olefin compound salt, comprising reprecipitating and/or recrystallizing a solid comprising at least one phosphorus-containing olefin compound salt selected from the group consisting of: a phosphorus-containing olefin compound salt A represented by the following formula (1):

##STR00001##

wherein X.sub.1 and X.sub.2 are each independently F, Cl, Br, I, or H; W.sup.+s are the same or different and each is a monovalent cation comprising PR.sub.3 or P(OR).sub.3, provided that Rs are groups having a saturated or unsaturated structure containing C and H, are optionally bonded together to form a ring, and optionally contain an atom other than C and H; three Rs included in R.sub.3 and (OR).sub.3 are optionally the same or different; and M.sup.− is a monovalent anion comprising an atom or a compound; and a phosphorus-containing olefin compound salt B represented by the following formula (2):

##STR00002##

wherein X.sub.1, X.sub.2, W.sup.+, and M.sup.− are as defined above, and Y is F, Cl, Br, I, H, an alkyl group, an alkyl ether group, a fluoroalkyl group, or a fluoroalkyl ether group; in a solvent, thereby obtaining a purified product of the phosphorus-containing olefin compound salt.

Provided is a method for purifying a phosphorus-containing olefin compound salt as a raw material or an intermediate that is useful to increase the purity of a target product in a method for producing an olefin compound and that can be applied to the production method, and a method for producing an olefin compound using a purified product obtained thereby.

Specifically, provided is a method for purifying a phosphorus-containing olefin compound salt, comprising reprecipitating and/or recrystallizing a solid comprising at least one phosphorus-containing olefin compound salt selected from the group consisting of: a phosphorus-containing olefin compound salt A represented by the following formula (1):

##STR00001##

wherein X.sub.1 and X.sub.2 are each independently F, Cl, Br, I, or H; W.sup.+s are the same or different and each is a monovalent cation comprising PR.sub.3 or P(OR).sub.3, provided that Rs are groups having a saturated or unsaturated structure containing C and H, are optionally bonded together to form a ring, and optionally contain an atom other than C and H; three Rs included in R.sub.3 and (OR).sub.3 are optionally the same or different; and M.sup.− is a monovalent anion comprising an atom or a compound; and a phosphorus-containing olefin compound salt B represented by the following formula (2):

##STR00002##

wherein X.sub.1, X.sub.2, W.sup.+, and M.sup.− are as defined above, and Y is F, Cl, Br, I, H, an alkyl group, an alkyl ether group, a fluoroalkyl group, or a fluoroalkyl ether group; in a solvent, thereby obtaining a purified product of the phosphorus-containing olefin compound salt.

A halogenated cycloalkane compound is obtained at a high conversion rate by reacting a halogenated cycloalkene compound and a hydrogen-containing gas in the presence of a hydrogenated catalyst or a catalyst having a hydrogen content of 0.1 to 1.5 mass %.

A halogenated cycloalkane compound is obtained at a high conversion rate by reacting a halogenated cycloalkene compound and a hydrogen-containing gas in the presence of a hydrogenated catalyst or a catalyst having a hydrogen content of 0.1 to 1.5 mass %.

A halogenated cycloalkane compound is obtained at a high conversion rate by reacting a halogenated cycloalkene compound and a hydrogen-containing gas in the presence of a hydrogenated catalyst or a catalyst having a hydrogen content of 0.1 to 1.5 mass %.