US2023142757A1PendingUtilityA1

Compositions and processes for producing chlorofluoroalkenes

83
Assignee: CHEMOURS CO FC LLCPriority: Aug 13, 2018Filed: Jan 3, 2023Published: May 11, 2023
Est. expiryAug 13, 2038(~12 yrs left)· nominal 20-yr term from priority
Inventors:Xuehui Sun
C08J 9/146C09K 2205/126C07C 17/206C11D 7/30C07C 2523/26C09K 2205/22C07C 17/25C09K 3/30C09K 5/044C08J 2203/162C11D 7/5018
83
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Claims

Abstract

A method of making chlorofluorohydrocarbons including, contacting, a fluorinated hydrocarbon reagent in the vapor phase, with hydrogen chloride (HCl). The reaction is conducted in the presence of an effective amount of a catalyst, at an elevated temperature sufficient to effect hydrochlorination to form a reaction mixture including a chlorofluorohydrocarbon.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . A composition comprising (Z)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(Z)), (a) at least one member selected from one of (E)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(E)), (Z)-1,2,3,3,3-pentafluoropropene (HFO-1225ye(Z)), (E)-1,2,3,3,3-pentafluoropropene (HFO-1225ye(E)), (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)), and (E)-1-chloro-3,3,3-trifluoropropene (1233zd(E)), and (b) at least additional member selected from one of 1,1,2,3,3-hexafluoropropane (HFC-236ea), 1,1,1,2,2,3-hexafluoropropane (HFC-236cb), 1-chloro-2,3,3,3-tetrafluoropropane (HCFC-244eb) and 1,1,1,2,3-pentafluoropropane (HFC-245eb). 
     
     
         2 . The composition of  claim 1  wherein the at least one member comprises (E)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(E)), (Z)-1,2,3,3,3-pentafluoropropene (HFO-1225ye(Z)), and (E)-1,2,3,3,3-pentafluoropropene (HFO-1225ye(E)). 
     
     
         3 . The composition of  claim 2 , wherein the additional member comprises 1,1,1,2,3,3-hexafluoropropane (HFC-236ea). 
     
     
         4 . The composition of  claim 2 , wherein the additional member comprises 1,1,1,2,2,3-hexafluoropropane (HFC-236cb). 
     
     
         5 . The composition of  claim 2 , wherein the additional member comprises 1,1,1,2,3-pentafluoropropane (HFC-245eb). 
     
     
         6 . The composition of  claim 2  further comprising 1,1,1,3,3-pentafluoropropane (HFC-245fa) or 1-chloro-1,3,3,3-tetrafluoropropane (HCFC-244fa). 
     
     
         7 . The composition of  claim 2 , containing from at least about 40 mole percent HCFO-1224(yd)(Z). 
     
     
         8 . A composition comprising (Z)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(Z)), at least one member selected from one of (E)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(E)), (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)), and (E)-1-chloro-3,3,3-trifluoropropene (1233zd(E)), and (b) at least one additional member selected from 3-chloro-1,1,1,2,2-pentafluoropropane (HFC-235cb), 1,1,2,3,3-hexafluoropropane (HFC-236ea), 1,1,1,2,2,3-hexafluoropropane (HFC-236cb), 1-chloro-2,3,3,3-tetrafluoropropane (HCFC-244eb), 1-chloro-1,3,3,3-tetrafluoropropane (HCFC-244fa), and 1,1,1,2,3-pentafluoropropane (HFC-245eb). 
     
     
         9 . The composition of  claim 8 , wherein the composition comprises (Z)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(Z)), (E)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(E)), (Z)-1,2,3,3,3-pentafluoropropene (HFO-1225ye(Z)), and (E)-1,2,3,3,3-pentafluoropropene (HFO-1225ye(E)), and 3-chloro-1,1,1,2,2-pentafluoropropane (HFC-235cb). 
     
     
         10 . The composition of  claim 8 , wherein the composition comprises (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and (E)-1-chloro-3,3,3-trifluoropropene (1233zd(E)), and at least one of 1-chloro-2,3,3,3-tetrafluoropropane (HCFC-244eb), 1-chloro-1,3,3,3-tetrafluoropropane (HCFC-244fa), 1,1,1,3,3-pentafluoropropane (HFC-245fa), and 1,1,1,2,3-pentafluoropropane (HFC-245eb), and 1,1,2-trichloro-2,3,3,3-tetrafluoropropane (HCFC-224ba). 
     
     
         11 . A composition comprises one of 1,2,3,3,4,4,4-heptafluoro-1-butene. (HFC-1327cye) or 1,2,3,3,3-pentafluoropropene (HFO-1225ye), and at least one of (Z)-1-chloro-2,3,3,4,4,4-hexafluoro-1-butene (HCFC-1326yd(Z)), (E)-1-chloro-2,3,3,4,4,4-hexafluoro-1-butene (HCFC-1326yd(E)), (Z)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(Z)), or (E)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(E)). 
     
     
         12 . The composition of  claim 11 , wherein the composition comprises (Z)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(Z)), (E)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(E)), (Z)-1,2,3,3,3-pentafluoropropene (HFO-1225ye(Z)), and (E)-1,2,3,3,3-pentafluoropropene (HFO-1225ye(E)). 
     
     
         13 . The composition of  claim 11 , wherein the composition comprises (Z)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(Z)), (E)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(E)), (Z)-1,2,3,3,3-pentafluoropropene (HFO-1225ye(Z)), (E)-1,2,3,3,3-pentafluoropropene (HFO-1225ye(E)), (Z)-1,2-dichloro-3,3,3-trifluoropropene (1223xd(Z)), and (E)-1,2-dichloro-3,3,3-trifluoropropene (1223xd(E)). 
     
     
         14 . A composition of  claim 11  comprises (Z)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(Z)), (E)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(E)), (Z)-1,2,3,3,3-pentafluoropropene (HFO-1225ye(Z)), (E)-1,2,3,3,3-pentafluoropropene (HFO-1225ye(E)), and at least one of 1,2,2-trichloro-3,3,3-trifluoropropane (HCFC-233da), 3-chloro-1,1,1,2,2-pentafluoropropane (HFC-235cb), 2-chloro-1,1,1,3,3-pentafluoropropane (HFC-235da), and 1,1,1,2,2,3-hexafluoropropane (HFC-236cb). 
     
     
         15 . The composition of  claim 11  comprises (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)), (E)-1-chloro-3,3,3-trifluoropropene (1233zd(E)), and 1,1,1,3,3-pentafluoropropane (HFC-245fa). 
     
     
         16 . The composition of  claim 11  comprises 1,1,1,2,2,3-heptafluoropropane (HFC-236cb), 3-chloro-1,1,1,2,2-pentafluoropropane (HFC-235cb), (Z)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(Z)), and (E)-1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd(E)). 
     
     
         17 . The composition comprises 1,3,3,3-tetrafluoropropene (HFC-1234ze), (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)), (E)-1-chloro-3,3,3-trifluoropropene (1233zd(E)), 1-chloro-2,3,3,3-tetrafluoropropane (HCFC-244eb), and 1,1,1,2,3-pentafluoropropane (HFC-245eb). 
     
     
         18 . A fluid comprising one of a refrigerant, a solvent, a blowing agent, a heat transfer agent, or an aerosol comprising the composition of any of  claims 1 ,  8 ,  11  or  17 . 
     
     
         19 . The composition according to  claim 1  containing from about 7 to about 95 percent HCFO-1224(yd)(Z). 
     
     
         20 . The composition according to  claim 20  containing about 40 to about 90 mole percent HCFO-1224(yd)(Z). 
     
     
         21 . The composition containing from about 7 to about 95 percent HCFO-1224(yd)(Z), HCFO-1225ye(Z), HCFO-1225ye(E) and HFC-236cb. 
     
     
         22 . The composition according to  claim 22  containing about 40 to about 90 mole percent HCFO-1224(yd)(Z). 
     
     
         23 . A material comprising one of a refrigerant, a solvent, a blowing agent, a heat transfer agent, or an aerosol comprising the composition of any of  claims 19 - 22 . 
     
     
         24 . A composition of 1224yd-Z, 1224yd-E, 1223xd-Z, and at least additional compounds selection from 1223xd(E), HFC-236ea, HFC-236cb, HFC-245eb, HFC-244eb, HCFO-1225ye, HCFC-233da, HFC-235da, and HFC-243db

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