Disclosed are compositions comprising HCFC-243db, HCFO-1233xf, HCFC-244db and/or HFO-1234yf and at least one additional compound. For the composition comprising 1234yf, the additional compound is selected from the group consisting of HFO-1234ze, HFO-1243zf, HCFC-243db, HCFC-244db, HFC-245cb, HFC-245fa, HCFO-1233xf, HCFO-1233zd, HCFC-253fb, HCFC-234ab, HCFC-243fa, ethylene, HFC-23, CFC-13, HFC-143a, HFC-152a, HFC-236fa, HCO-1130, HCO-1130a, HFO-1336, HCFC-133a, HCFC-254fb, CHF═CHCl, HFO-1141, HCFO-1242zf, HCFO-1223xd, HCFC-233ab, HCFC-226ba, and HFC-227ca. Compositions comprising HCFC-243db, HCFO-1233xf, and/or HCFC-244db are useful in processes to make HFO-1234yf. Compositions comprising HFO-1234yf are useful, among other uses, as heat transfer compositions for use in refrigeration, air-conditioning and heat pump systems.

Disclosed are compositions comprising HCFC-243db, HCFO-1233xf, HCFC-244db and/or HFO-1234yf and at least one additional compound. For the composition comprising 1234yf, the additional compound is selected from the group consisting of HFO-1234ze, HFO-1243zf, HCFC-243db, HCFC-244db, HFC-245cb, HFC-245fa, HCFO-1233xf, HCFO-1233zd, HCFC-253fb, HCFC-234ab, HCFC-243fa, ethylene, HFC-23, CFC-13, HFC-143a, HFC-152a, HFC-236fa, HCO-1130, HCO-1130a, HFO-1336, HCFC-133a, HCFC-254fb, CHF═CHCl, HFO-1141, HCFO-1242zf, HCFO-1223xd, HCFC-233ab, HCFC-226ba, and HFC-227ca. Compositions comprising HCFC-243db, HCFO-1233xf, and/or HCFC-244db are useful in processes to make HFO-1234yf. Compositions comprising HFO-1234yf are useful, among other uses, as heat transfer compositions for use in refrigeration, air-conditioning and heat pump systems.

Disclosed are compositions comprising HCFC-243db, HCFO-1233xf, HCFC-244db and/or HFO-1234yf and at least one additional compound. For the composition comprising 1234yf, the additional compound is selected from the group consisting of HFO-1234ze, HFO-1243zf, HCFC-243db, HCFC-244db, HFC-245cb, HFC-245fa, HCFO-1233xf, HCFO-1233zd, HCFC-253fb, HCFC-234ab, HCFC-243fa, ethylene, HFC-23, CFC-13, HFC-143a, HFC-152a, HFC-236fa, HCO-1130, HCO-1130a, HFO-1336, HCFC-133a, HCFC-254fb, CHF═CHCl, HFO-1141, HCFO-1242zf, HCFO-1223xd, HCFC-233ab, HCFC-226ba, and HFC-227ca. Compositions comprising HCFC-243db, HCFO-1233xf, and/or HCFC-244db are useful in processes to make HFO-1234yf. Compositions comprising HFO-1234yf are useful, among other uses, as heat transfer compositions for use in refrigeration, air-conditioning and heat pump systems.

Disclosed are compositions comprising HCFC-243db, HCFO-1233xf, HCFC-244db and/or HFO-1234yf and at least one additional compound. For the composition comprising 1234yf, the additional compound is selected from the group consisting of HFO-1234ze, HFO-1243zf, HCFC-243db, HCFC-244db, HFC-245cb, HFC-245fa, HCFO-1233xf, HCFO-1233zd, HCFC-253fb, HCFC-234ab, HCFC-243fa, ethylene, HFC-23, CFC-13, HFC-143a, HFC-152a, HFC-236fa, HCO-1130, HCO-1130a, HFO-1336, HCFC-133a, HCFC-254fb, CHF═CHCl, HFO-1141, HCFO-1242zf, HCFO-1223xd, HCFC-233ab, HCFC-226ba, and HFC-227ca. Compositions comprising HCFC-243db, HCFO-1233xf, and/or HCFC-244db are useful in processes to make HFO-1234yf. Compositions comprising HFO-1234yf are useful, among other uses, as heat transfer compositions for use in refrigeration, air-conditioning and heat pump systems.

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.

The present disclosure relates to a method for producing a fluorinated organic compound comprises reacting a compound represented by formula (1):

##STR00001##

(wherein R.sup.1 and R.sup.2 are each independently a hydrogen atom, a halogen atom, or an organic group, or R.sup.1 and R.sup.2 optionally form a ring together with the two adjacent carbon atoms; n is 1 or 2; and wherein two R.sup.1s are optionally the same or different, two R.sup.2s are optionally the same or different, or two R′s or two R.sup.2s optionally form a ring together with their adjacent carbon atom), with (A) at least one fluorine source selected from the group consisting of hydrogen fluoride, hydrogen fluoride salts, and fluoride salts, and (B) a halogen source other than fluorine represented by the formula: R.sup.3(OX).sub.m (wherein R.sup.3 is a hydrogen atom, a cation, or an organic group, X is a halogen atom other than a fluorine atom, and m is an integer corresponding to the valence of R.sup.3), to add fluorine and a halogen other than fluorine to the double bond or triple bond.

The present disclosure relates to a method for producing a fluorinated organic compound comprises reacting a compound represented by formula (1):

##STR00001##

(wherein R.sup.1 and R.sup.2 are each independently a hydrogen atom, a halogen atom, or an organic group, or R.sup.1 and R.sup.2 optionally form a ring together with the two adjacent carbon atoms; n is 1 or 2; and wherein two R.sup.1s are optionally the same or different, two R.sup.2s are optionally the same or different, or two R′s or two R.sup.2s optionally form a ring together with their adjacent carbon atom), with (A) at least one fluorine source selected from the group consisting of hydrogen fluoride, hydrogen fluoride salts, and fluoride salts, and (B) a halogen source other than fluorine represented by the formula: R.sup.3(OX).sub.m (wherein R.sup.3 is a hydrogen atom, a cation, or an organic group, X is a halogen atom other than a fluorine atom, and m is an integer corresponding to the valence of R.sup.3), to add fluorine and a halogen other than fluorine to the double bond or triple bond.

A process is disclosed for making CF.sub.3CF═CHF. The process involves reacting CF.sub.3CClFCCl.sub.2F with H.sub.2 in a reaction zone in the presence of a catalyst to produce a product mixture comprising CF.sub.3CF═CHF. The catalyst has a catalytically effective amount of palladium supported on a support selected from the group consisting of alumina, fluorided alumina, aluminum fluoride and mixtures thereof and the mole ratio of H.sub.2 to CF.sub.3CClFCCl.sub.2F fed to the reaction zone is between about 1:1 and about 5:1. Also disclosed are azeotropic compositions of CF.sub.3CClFCCl.sub.2F and HF and azeotropic composition of CF.sub.3CHFCH.sub.2F and HF.

A process is disclosed for making CF.sub.3CF═CHF. The process involves reacting CF.sub.3CClFCCl.sub.2F with H.sub.2 in a reaction zone in the presence of a catalyst to produce a product mixture comprising CF.sub.3CF═CHF. The catalyst has a catalytically effective amount of palladium supported on a support selected from the group consisting of alumina, fluorided alumina, aluminum fluoride and mixtures thereof and the mole ratio of H.sub.2 to CF.sub.3CClFCCl.sub.2F fed to the reaction zone is between about 1:1 and about 5:1. Also disclosed are azeotropic compositions of CF.sub.3CClFCCl.sub.2F and HF and azeotropic composition of CF.sub.3CHFCH.sub.2F and HF.