Organic compounds -- part of the class 532-570 series – Organic compounds – Halogen containing
Patent
1995-12-08
1998-02-03
Ivy, C. Warren
Organic compounds -- part of the class 532-570 series
Organic compounds
Halogen containing
570160, 570170, C07C 17087, C07C 1720
Patent
active
057146551
DESCRIPTION:
BRIEF SUMMARY
This application is a 35 USC 371 National Stage filing of PCT/JP94/00867 published as WO94/29252 on Dec. 22, 1994.
INDUSTRIAL USE
This invention pertains to the process of manufacturing 1,1,1,3,3-pentafluoropropane (HFC245fa), a useful compound which may become a substitute compound for CFC and HCFC used as refrigerant, blowing agent and cleaner, in more detail to the process of manufacturing 1,1,1,3,3-pentafluoropropane with 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane (CFC215aa) as an intermediate, to the process of manufacturing 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane (CFC215aa), an intermediate of HFC245fa, and to the process of manufacturing 2,3,3-trichloro-1,1,1-trifluoropropene, an intermediate of CFC215aa.
PRIOR ART
1,1,1,3,3-pentafluoropropane (HFC245fa) is a useful compound as a substitute for freon used as a blowing agent, refrigerant, cleaner, etc.
As the process of manufacturing 1,1,1,3,3-pentafluoropropane (HFC245fa), a method is known under which 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane (CFC215aa) is used as a raw material, which is reduced with a palladium catalyst supported on activated carbon using 1.5 to 4 mols of hydrogen to the raw material (U.S. Pat. No. 2,942,036).
Manufacturing HFC245fa using CFC215aa involves two broad categories of problems. The first problem is how efficiently and economically CFC215aa is manufactured, and the second problem is how efficiently CFC215aa is reduced to obtain HFC245fa.
Regarding the first problem, it is important to select a low-priced starting material and to efficiently convert it into CFC215aa. There have been several reports on techniques of using low-price available compound with carbon number of 3 as a starting material, then chlorine-fluorinating it to obtain CF.sub.3 CFC1CF.sub.3.
Japanese Patent Opening No. 145033/92 discloses a process of manufacturing CF3 CFC1CF3 in which propane and propylene, etc. are chlorofluorinated to generate a perhalogenated C3 chlorofluoro compound, and this compound is fluorinated. Japanese Patent Opening No. 117335/92 discloses a process in which propane and propylene, etc. are chlorine-fluorinated to generate CF.sub.3 CC1=CC1.sub.2, and this compound is further chlorine-fluorinated to form CF.sub.3 CFC1CF.sub.3. Japanese Patent Opening No. 108746/92 discloses a process in which hexachloropropene is chlorofluorinated to generate a perhalogenated C.sub.3 chlorofluoro compound and this compound is fluorinated to form CF.sub.3 CFC1CF.sub.3.
However, these processes are designed to obtain CF.sub.3 CFC1CF.sub.3 (a C.sub.3 compound with 7 fluorine atoms and 1 chlorine atom), and the application of these processes to the manufacture of CF.sub.3 CC1.sub.2 CF.sub.2 C1 (a C.sub.3 compound with 5 fluorine atoms and 3 chlorine atoms) (CFC215aa) produces a large amount of by-product which are too fluorinated, thus not only producing a low yield rate, but also making it impossible to reuse the by-product as a raw material for manufacturing CFC215aa. A method of synthesizing the conditions suitable for the manufacture of CFC215aa therefore needs to be developed.
Regarding the second problem, that is, the reduction of CFC215aa, the above U.S. patented process provides only a maximum 60% yield rate to HFC245fa, the subject-matter, and also produces a large amount of 1,1,3,3,3-pentafluoropropene, which is not suitable for industry. Consequently, an efficient process of reducing CFC215aa into HFC245fa needs to be developed.
OBJECT OF INVENTION
The object of this invention is to provide a process to efficiently and economically manufacture 1,1,1,3,3-pentafluoropropane, especially a process of manufacturing 1,1,1,3,3-pentafluoropropane at a high yield rate in the reductive reaction of 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane.
The other object of this invention is to provide a process to efficiently and economically manufacture 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane and 2,3,3-trichloro-1,1,1-trifluoropropene as intermediates in the manufacture of 1,1,1,3,3-pentafluoropropane.
CONSTITUTION OF INVENTION
REFERENCES:
patent: 2558703 (1951-06-01), Gochenour
patent: 2942036 (1960-06-01), Smith et al.
patent: 5057634 (1991-10-01), Webster et al.
patent: 5068472 (1991-11-01), Webster et al.
patent: 5315048 (1994-05-01), VanDerPuy et al.
patent: 5364992 (1994-11-01), Manogue et al.
patent: 5488189 (1996-01-01), Sievert et al.
Aoyama Hirokazu
Nakada Tatsuo
Seki Eiji
Takubo Seiji
Yamamoto Akinori
Daikin Industries Ltd.
Ivy C. Warren
Smith Lyman H.
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