US2016039729A1PendingUtilityA1

Method for producing fluorinated organic compounds

53
Assignee: HONEYWELL INT INCPriority: Apr 29, 2004Filed: Aug 10, 2015Published: Feb 11, 2016
Est. expiryApr 29, 2024(expired)· nominal 20-yr term from priority
Inventors:Hsueh Sung TungSudip MukhopadhyayMichael Van Der PuyDaniel C. MerkelJing Ji MaCheryl L. BortzBarbara A. LightSteven D. PhillipsKim M. FlemingSusan A. Ferguson
C07C 17/206C07C 17/23C07C 19/08C07C 17/10C07C 17/087C07C 17/21C07C 17/25
53
PatentIndex Score
0
Cited by
0
References
0
Claims

Abstract

Disclosed is a process for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of Formula (I): C(X)3CF2C(X)3  (I) to at least one compound of Formula (II) CF3CF═CHZ  (II) where each X and Z is independently H, F, Cl, I or Br, said process preferably not including any substantial amount of oxygen-containing catalyst in certain embodiments. Preferably Z is H.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . A method for producing fluorinated organic compounds comprising converting at least one compound of Formula (I)
   C(X) 3 CF 2 C(X) 3   (I)
   
       to at least one compound of Formula (II)
   CF 3 CF═CHZ  (II)
 
 
       where each X and Z is independently H, F, Cl, I or Br, said converting step being carried out in the substantial absence of oxygen-containing metal catalyst. 
     
     
         2 . The method of  claim 1  wherein said converting step is a direct converting step. 
     
     
         3 . The method of  claim 1  wherein said converting step is an indirect converting step. 
     
     
         4 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises a compound wherein each X on one terminal carbon is H and wherein each X on the other terminal carbon is independently selected from F, Cl, I or Br. 
     
     
         5 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises a compound Formula (IA):
   C(X) 3 CF 2 CH 3   (IA)
 
 
       wherein each X is independently F, Cl, Br or I. 
     
     
         6 . The method of  claim 5  wherein Z in said compound of Formula (II) is H. 
     
     
         7 . The method of  claim 5  wherein each X is F. 
     
     
         8 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises at least pentahalogenated compound. 
     
     
         9 . The method of  claim 5  wherein said at least one compound of Formula (IA) comprises at least one trichlorinated, difluorinated propane. 
     
     
         10 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises 1,1,1-trichloro-2,2-difluoropropane (HCFC-242bb). 
     
     
         11 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises 1,1,1,2,2-pentafluoropropane (HFC-245cb). 
     
     
         12 . The method of  claim 1  wherein said at least one compound of Formula (I) is selected from the group consisting of HCFC-242bb, HFC-245cb and combinations of these. 
     
     
         13 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises at least a first compound of Formula (IA)
   C(X) 3 CF 2 CH 3   (IA)
 
 
       wherein X is as defined in  claim 1 , wherein said first compound of Formula (IA) is not pentafluorinated, and wherein said converting step comprises converting said first compound of Formula (IA) to a second compound of Formula (IA) wherein said second compound is pentafluorinated. 
     
     
         14 . The method of  claim 13  wherein said first compound of Formula (IA) comprises at least 1,1,1-trichloro-2,2-difluoropropane (HCFC-242bb) and said second compound of Formula (IA) comprises at least 1,1,1,2,2-pentafluoropropane (HFC-245cb). 
     
     
         15 . The method of  claim 13  wherein said at least one compound in accordance with Formula (II) comprises HFO-1234yf. 
     
     
         16 . The method of  claim 13  wherein said exposing step comprises at least one gas phase catalytic reaction. 
     
     
         17 . The method of  claim 1  wherein said converting step comprises at least one gas phase catalytic reaction. 
     
     
         18 . The method of  claim 1  wherein said converting step comprises exposing the compound of Formula (I) to one or more sets of reaction conditions effective to produce at least one compound in accordance with Formula (II). 
     
     
         19 . The method of  claim 18  wherein said exposing step comprises reacting said at least one compound of Formula (I) under conditions effective to produce at least one chlorofluoropropane. 
     
     
         20 . The method of  claim 1  further comprising the step of providing said compound of Formula (I) by converting at least one compound of Formula (III):
   C(X) 2 ═CClC(X) 3   (III)
 
 
       to at least one compound of Formula (I), where each X in Formula III is independently H, F, Cl, I or Br, provided at least one X is Cl, I or Br. 
     
     
         21 . The method of  claim 20  wherein at least one X on the unsaturated carbon of Formula III is Cl, I or Br. 
     
     
         22 . The method of  claim 20  wherein at least one X on the unsaturated carbon of Formula III is Cl. 
     
     
         23 . The method of  claim 20  wherein converting step comprises converting said compound of Formula (III) in the presence of a catalyst. 
     
     
         24 . A method for producing fluorinated organic compounds comprising providing at least one compound of Formula (I)
   C(X) 3 CF 2 C(X) 3   (I)
   
       and exposing said Formula (I) compound to reaction conditions effective to convert at least about 50% of said compound to a compound of Formula (II)
   CF 3 CF═CHZ  (II)
 
 
       where each X is independently F, Cl, I or Br, said converting step being carried out in the substantial absence of oxygen-containing metal catalyst. 
     
     
         25 . The method of  claim 24  wherein said exposing step comprises exposing said Formula (I) compound to reaction conditions effective to convert at least about 75% of said compound to a compound of Formula (II). 
     
     
         26 . The method of  claim 24  wherein said exposing step comprises exposing said Formula (I) compound to reaction conditions effective to convert at least about 90% of said compound to a compound of Formula (II). 
     
     
         27 . The method of  claim 24  wherein said exposing step comprises exposing said Formula (I) compound to reaction conditions effective to convert at least about 97% of said compound to a compound of Formula (II). 
     
     
         28 . The method of  claim 24  wherein said exposing step comprises exposing said Formula (I) compound to reaction conditions effective to produce a Formula (II) selectivity of at least about 45%. 
     
     
         29 . The method of  claim 24  wherein said exposing step comprises exposing said Formula (I) compound to reaction conditions effective to produce a Formula (II) selectivity of at least about 55%. 
     
     
         30 . The method of  claim 24  wherein said exposing step comprises exposing said Formula (I) compound to reaction conditions effective to produce a Formula (II) selectivity of at least about 75%. 
     
     
         31 . The method of  claim 24  wherein said exposing step comprises exposing said Formula (I) compound to reaction conditions effective to produce a Formula (II) selectivity of at least about 75%. 
     
     
         32 . A method for producing fluorinated organic compounds comprising introducing into a first stage of a reactor having at least two reaction stages at least one compound of Formula (I)
   C(X) 3 CF 2 C(X) 3   (I)
   
       under conditions effective to produce to at least one compound of Formula (II)
   CF 3 CF═CHZ  (II)
 
 
       where each X and Z is independently H, F, Cl, I or Br. 
     
     
         33 . The method of  claim 32  wherein said first reaction stage comprises a gas phase catalytic reaction stage and where said compound of Formula (I) comprises a first compound in accordance with Formula (I), said first compound being a chlorinated compound. 
     
     
         34 . The method of  claim 33  wherein in said first reaction stage said first compound of Formula (I) is at least partially converted to a second compound in accordance with Formula (I), said second compound being a non-chlorinated compound in accordance with Formula (I). 
     
     
         35 . The method of  claim 34  wherein said second compound in accordance with Formula (I) comprises a penta-fluorinated compound. 
     
     
         36 . The method of  claim 35  wherein said second compound in accordance with Formula (I) comprises a compound having no halogen substituents other than F. 
     
     
         37 . The method of  claim 35  wherein said second compound in accordance with Formula (I) comprises HFC-245. 
     
     
         38 . The method of  claim 34  further comprising reacting said second compound in accordance with Formula (I) in a second stage of reaction in the presence of a catalyst to produce at least one compound of Formula (II). 
     
     
         39 . The method of  claim 38  wherein said first reaction stage contains at least a first catalyst and said reaction stage contains at least a second catalyst. 
     
     
         40 . The method of  claim 39  wherein said first reaction stage comprises a fluorination reaction stage containing at least a first fluorination catalyst. 
     
     
         41 . The method of  claim 40  wherein said first fluorination catalyst comprises a Sb-based catalyst. 
     
     
         42 . The method of  claim 40  wherein said first fluorination catalyst comprises a Fe-based catalyst. 
     
     
         44 . The method of  claim 40  wherein said second catalyst comprises a metal-based catalyst. 
     
     
         45 . The method of  claim 44  wherein said second catalyst comprises a nickel-based catalyst. 
     
     
         46 . The method of  claim 44  wherein said second catalyst comprises a carbon-based catalyst. 
     
     
         47 . The method of claim  43  wherein said second compound is a penta-fluorinated compound. 
     
     
         48 . The method of claim  43  wherein said second compound is HFC-245. 
     
     
         49 . The method of claim  43  wherein said compound of Formula (II) comprises HFO-1234yf. 
     
     
         50 . The method of  claim 32  wherein said first reaction stage comprises a gas phase catalytic reaction stage and where said compound of Formula (I) comprises a first compound in accordance with Formula (I) containing fluorine and at least one other halogen. 
     
     
         51 . The method of  claim 50  wherein in said first reaction stage said compound of Formula (I) is converted to a second compound in accordance with Formula (I) having no halogen substituents other than fluorine. 
     
     
         52 . The method of  claim 50  wherein said first compound in accordance with Formula (I) comprises a penta-halogenated compound. 
     
     
         53 . The method of  claim 52  wherein said penta-halogenated compound in accordance with Formula (I) comprises a trichlorinated, difluorinated propane. 
     
     
         54 . The method of  claim 53  wherein said penta-halogenated compound in accordance with Formula (I) comprises 1,1,1-trichloro-2,2-difluoropropane (HCFC-242bb). 
     
     
         55 . The method of  claim 51  wherein said second compound in accordance with Formula (I) comprises a penta-fluorinated propane. 
     
     
         56 . The method of  claim 55  wherein said second compound in accordance with Formula (I) comprises 1,1,2,2,2-pentafluoropropane (HFC-245).

Cited by (0)

No later patents cite this yet.

References (0)

No backward citations on record.