Processes for the production of fluoropropanes and halopropenes and azeotropic compositions of 2-chloro-3,3,3-trifluoro-1-propene with HF and of 1,1,1,2,2-pentafluoropropane with HF
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C09K-005/04
C07C-021/18
출원번호
US-0444470
(2007-10-31)
등록번호
US-8398882
(2013-03-19)
국제출원번호
PCT/US2007/022994
(2007-10-31)
§371/§102 date
20090406
(20090406)
국제공개번호
WO2008/054781
(2008-05-08)
발명자
/ 주소
Rao, Velliyur Nott Mallikarjuna
Sievert, Allen Capron
출원인 / 주소
E I du Pont de Nemours and Company
인용정보
피인용 횟수 :
25인용 특허 :
18
초록▼
A process is disclosed for making CF3CF2CH3, CF3CF═CH2 and/or CF3CCl═CH2. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CHClCH2X, halopropenes of the formula CClX2CCl═CH2 and halopropenes of the formula CX2═CClCH2X,
A process is disclosed for making CF3CF2CH3, CF3CF═CH2 and/or CF3CCl═CH2. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CHClCH2X, halopropenes of the formula CClX2CCl═CH2 and halopropenes of the formula CX2═CClCH2X, wherein each X is independently F or Cl, with HF in a reaction zone to produce a product mixture comprising HF, HCl, CF3CF2CH3, CF3CF═CH2 and CF3CCl═CH2; and recovering the CF3CF2CH3, CF3CF═CH2 and/or CF3CCl═CH2 from the product mixture.
대표청구항▼
1. A vapor-phase process for making at least one product compound selected from the group consisting of CF3CF2CH3, CF3CF═CH2 and CF3CCl═CH2, comprising: reacting a halopropane of the formula CX3CHClCH2X wherein each X is independently selected from the group consisting of F and Cl, with HF in a reac
1. A vapor-phase process for making at least one product compound selected from the group consisting of CF3CF2CH3, CF3CF═CH2 and CF3CCl═CH2, comprising: reacting a halopropane of the formula CX3CHClCH2X wherein each X is independently selected from the group consisting of F and Cl, with HF in a reaction zone, optionally in the presence of a fluorination catalyst, to produce a product mixture comprising HF, HCl, CF3CF2CH3, CF3CF═CH2 and CF3CCI═CH2, wherein the molar ratio of HF to total amount of starting material fed to the reaction zone is from about 10:1 to about 30:1; andrecovering said at least one product compound from the product mixture. 2. The process of claim 1 wherein CF3CF═CH2 is recovered. 3. The process of claim 2 wherein CF3CF2CH3 from the product mixture is dehydrofluorinated to produce additional CF3CF═CH2. 4. The process of claim 1 wherein CF3CCI═CH2 from the product mixture is fluorinated to produce at least one of CF3CF═CH2 and CF3CF2CH3. 5. The process of claim 1 wherein the product mixture further comprises CF3CH2CHF2; and wherein CF3CH2CHF2 from the product mixture is dehydrofluorinated to produce CF3CH═CHF. 6. The process of claim 1 wherein the product mixture further comprises CF3CH═CHF; and wherein a mixture of CF3CF2CH3 and CF3CH═CHF is recovered and further reacted under dehydrofluorination conditions in the presence of a dehydrofluorination catalyst to produce a mixture comprising CF3CH═CHF and CF3CF═CH2. 7. The process of claim 1 wherein the product mixture further comprises CF3CH2CHF2 and CF3CH═CHCl, and wherein the CF3CCl═CH2, CF3CH2CHF2 and CF3CH═CHCl from the product mixture are further reacted with HF in the liquid phase under fluorination conditions in the presence of a fluorination catalyst to produce a mixture comprising CF3CH2CHF2 and CF3CF2CH3. 8. The process of claim 1 wherein the starting material is reacted in the presence of a fluorination catalyst. 9. The process of claim 8 wherein the fluorination catalyst comprises at least one chromium-containing component selected from the group consisting of crystalline alpha-chromium oxide where from about 0.05 atom % to about 6 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by trivalent cobalt atoms, and crystalline alpha-chromium oxide where from about 0.05 atom % to about 6 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by trivalent cobalt atoms which has been treated with a fluorinating agent. 10. The process of claim 1 wherein the product mixture further comprises CF3CH═CHF; and wherein a mixture of CF3CF2CH3 and CF3CH═CHF is recovered and further reacted with HF in the liquid phase under fluorination conditions in the presence of a fluorination catalyst to produce a mixture comprising CF3CH2CHF2 and CF3CF2CH3. 11. The process of claim 1 wherein CF3CF2CH3, CF3CF═CH2, and CF3CCl═CH2 from the product mixture together with CF3CH2CHF2, CF3CH═CHF, and CF3CH═CHCl from the product mixture, if present, are further reacted with HF in the liquid phase under fluorination conditions in the presence of a fluorination catalyst to produce a mixture comprising CF3CH2CHF2 and CF3CF2CH3. 12. The process of claim 11 wherein CF3CH2CHF2 and CF3CF2CH3 from the mixture is dehydrofluorinated to produce both CF3CH═CHF and CF3CF═CH2; and wherein both CF3CH═CHF and CF3CF═CH2 are recovered. 13. The process of claim 1 wherein the reaction zone temperature is from about 150° C. to about 275° C. and wherein CF3CCl═CH2 is the major product. 14. The process of claim 1 wherein the halopropane is CF3CHClCH2Cl, the reaction zone temperature is from about 275° C. to about 400° C., and the total yield of CF3CF═CH2 and CF3CCl═CH2 is at least about 54.2% 50%. 15. A liquid-phase process for making at least one product compound selected from the group consisting of CF3CF2CH3, CF3CF═CH2 and CF3CCl═CH2, comprising: reacting a halopropane of the formula CX3CHClCH2X wherein each X is independently selected from the group consisting of F and Cl, with HF in a reaction zone, optionally in the presence of a fluorination catalyst, to produce a product mixture comprising HF, HCl, CF3CF2CH3, CF3CF═CH2 and CF3CCl═CH2, wherein the molar ratio of HF to total amount of starting material fed to the reaction zone is from about 8:1 to about 50:1; andrecovering said at least one product compound from the product mixture. 16. The process of claim 15 wherein CF3CF═CH2 is recovered. 17. The process of claim 16 wherein CF3CF2CH3 from the product mixture is dehydrofluorinated to produce additional CF3CF═CH2. 18. The process of claim 15 wherein CF3CCl═CH2 from the product mixture is fluorinated to produce at least one of CF3CF═CH2 and CF3CF2CH3. 19. The process of claim 15 wherein the product mixture further comprises CF3CH2CHF2; and wherein CF3CH2CHF2 from the product mixture is dehydrofluorinated to produce CF3CH═CHF. 20. The process of claim 15 wherein the product mixture further comprises CF3CH═CHF; and wherein a mixture of CF3CF2CH3 and CF3CH═CHF is recovered and further reacted under dehydrofluorination conditions in the presence of a dehydrofluorination catalyst to produce a mixture comprising CF3CH═CHF and CF3CF═CH2. 21. The process of claim 15 wherein the product mixture further comprises CF3CH2CHF2 and CF3CH═CHCl, and wherein the CF3CCl═CH2, CF3CH2CHF2 and CF3CH═CHCl from the product mixture are further reacted with HF in the liquid phase under fluorination conditions in the presence of a fluorination catalyst to produce a mixture comprising CF3CH2CHF2 and CF3CF2CH3. 22. The process of claim 15 wherein the starting material is reacted in the presence of a fluorination catalyst. 23. The process of claim 15 wherein the product mixture further comprises CF3CH═CHF; and wherein a mixture of CF3CF2CH3 and CF3CH═CHF is recovered and further reacted with HF in the liquid phase under fluorination conditions in the presence of a fluorination catalyst to produce a mixture comprising CF3CH2CHF2 and CF3CF2CH3. 24. The process of claim 15 wherein CF3CF2CH3, CF3CF═CH2, and CF3CCl═CH2 from the product mixture together with CF3CH2CHF2, CF3CH═CHF, and CF3CH═CHCl from the product mixture, if present, are further reacted with HF in the liquid phase under fluorination conditions in the presence of a fluorination catalyst to produce a mixture comprising CF3CH2CHF2 and CF3CF2CH3. 25. The process of claim 24 wherein CF3CH2CHF2 and CF3CF2CH3 from the mixture is dehydrofluorinated to produce both CF3CH═CHF and CF3CF═CH2; and wherein both CF3CH═CHF and CF3CF═CH2 are recovered.
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