Conversion of chlorofluororopanes and chlorofluropropenes to more desirable fluoropropanes and fluororopenes

{
  "publication_number": "US10584082B2",
  "country": "US",
  "kind": "B2",
  "title": "Conversion of chlorofluororopanes and chlorofluropropenes to more desirable fluoropropanes and fluororopenes",
  "abstract": "A process is provided comprising contacting and reacting the compound CF 3 CF 2 CHXCl, wherein X is H or Cl, or the compound CF 3 CF═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 3 CF═CH 2 and CF 3 CH═CHF.",
  "claims": [
    "1. A reaction product comprising HCFC-235da (CF 3 CHClCHF 2), HCFC-234db (CF 3 CHClCH 2 F) and at least one of HFO-1234yf (CF 3 CF═CH 2), HFO-1234ze (CF 3 CH═CHF), HCFO-1224yd (CF 3 CF═CHCl), and HFO-1225zc (CF 3 CH═CF 2).",
    "2. The reaction product of claim 1 wherein the hydrofluoropropene comprises at least one of HFO-1234yf and HFO-1234ze.",
    "3. The reaction product of claim 2 wherein the hydrofluoropropene comprises HFO-1234yf.",
    "4. The reaction product of claim 2 wherein the hydrofluoropropene comprises HFO-1234ze.",
    "5. A composition comprising a reaction product and at least one intermediate convertible to the reaction product wherein the reaction product comprises at least one of HFO-1234yf (CF 3 CF═CH 2) and HFO-1234ze (CF 3 CH═CHF), and the intermediate comprises at least one of HCFC-234db (CF 3 CHClCH 2 F) and HCFC-235da (CF 3 CHClCHF 2).",
    "6. The composition of claim 5 wherein the reaction product comprises HFO-1234yf.",
    "7. The composition of claim 5 wherein the reaction product comprises HFO-1234ze.",
    "8. A composition comprising HCFC-235da (CF 3 CHClCHF 2), HCFC-234db (CF 3 CHClCH 2 F), HFO-1234yf (CF 3 CF═CH 2), and HFO-1234ze (CF 3 CH═CHF).",
    "9. A composition consisting essentially of HCFC-235da (CF 3 CHClCHF 2), HCFC-234db (CF 3 CHClCH 2 F), and HFO-1234yf (CF 3 CF═CH 2).",
    "10. A composition consisting essentially of HCFC-235da (CF 3 CHClCHF 2), HCFC-234db (CF 3 CHClCH 2 F), and HFO-1234ze (CF 3 CH═CHF).",
    "11. The reaction product of claim 1 wherein the hydrofluoropropene comprises at least one of HCFO-1224yd (CF 3 CF═CHCl), and HFO-1225zc (CF 3 CH═CF 2)."
  ],
  "description_excerpt": "The present invention relates to chemical processes for converting chlorofluoropropanes (HCFC) and chlorofluoropropenes (CFO) to more desirable fluoropropanes and fluoropropenes, especially propenes that are hydrofluoroolefins (HFO), i.e. free of Cl, and to intermediates from which these HFOs can be obtained.\n\nU.S. Pat. No. 8,399,722 discloses the hydrogenation of at least one of 1,1-dichloro-2,3,3,3-tetrafluoropropene (CF 3 CF═Cl 2, 1214ya) and 1-chloro-2,3,3,3-tetrafluoropropene (CF 3 CF═CHCl, 1224yd) in the presence of catalyst composed of Pd supported on a carbon carrier to obtain 2,3,3,3,-tetrafluoropropene (CF 3 CF═CH 2, 1234yf), which is free of chlorine and which has promise at least as a refrigerant exhibiting both low ozone depletion potential and low global warming potential. Example 2 discloses the conversion rate 1214ya to 1234yf to be 75%, which can also be considered the selectivity of the process. In Example 3 the selectivity dropped to 69%.\n\nProcesses are desired to obtain better results in the production of HFO-1234yf, and/or to obtain HFO-1234ze (CF3CH═CHF), 1,3,3,3-tetrafluoropropene), which is also free of chlorine and has refrigerant application, and/or which opens up new routes for obtaining desirable HFOs such as HFO-1234yf or HFO-1234ze.",
  "cpc": [
    "C07C 17/354",
    "C07C 17/23",
    "C07C 17/25",
    "C07C 19/08",
    "C07C 19/10",
    "C07C 21/18",
    "Y02P 20/582"
  ],
  "ipc": [
    "C07C 17/23",
    "C07C 17/25",
    "C07C 17/354",
    "C07C 19/10",
    "C07C 21/18"
  ],
  "assignees": [
    "Chemours Co FC LLC"
  ],
  "inventors": [
    "Xuehui Sun"
  ],
  "filing_date": "2019-06-10",
  "publication_date": "2020-03-10",
  "grant_date": "2020-03-10",
  "priority_date": "2014-04-16",
  "application_number": "US-201916435615-A",
  "family_id": "52823904",
  "cited_by_count": 11,
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}