Organic compounds -- part of the class 532-570 series – Organic compounds – Halogen containing
Patent
1995-05-19
1996-05-14
Evans, Joseph E.
Organic compounds -- part of the class 532-570 series
Organic compounds
Halogen containing
570153, C07C 17263, C07C 17354, C07C 1908, C07C 2118
Patent
active
055169511
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to a process for preparing 1,1,1,4,4,4-hexafluoro-2-butene and 1,1,1,4,4,4-hexafluorobutane.
1,1,1,4,4,4-Hexafluorobutane (hereinafter referred to as "HFC-356mff") is one of compounds which can substitute for chlorofluorocarbons or hydrochlorofluorocarbons used as coolants, blowing agents, cleaners, etc.
1,1,1,4,4,4-Hexafluoro-2-butene (hereinafter referred to as "HFC-1336") is useful as an intermediate for the production of compounds which can substitute for chlorofluorocarbons or hydrochlorofluorocarbons used as coolants, blowing agents, cleaners, etc., or as a monomer of fluorine-containing polymers.
PRIOR ART
In these years, serious attentions have been paid on preservation of environment, and hydrofluorocarbons, which can substitute for chlorofluorocarbons or hydrochlorofluorocarbons used as coolants, blowing agents, cleaners, etc., have been studied and selected. In connection therewith, a process for easy preparation of such hydrofluorocarbon or an intermediate for its production has been sought.
In general, HFC-356mff is easily prepared by adding hydrogen to HFC-1336. Then, a process for easy and effective preparation of HFC-1336 is required. However, any process for the effective preparation of HFC-1336 has not been proposed.
1,1,1-Trifluoro-2,2-dichloroethane (hereinafter referred to as "HCFC-123") is an easily available cheap raw material. But, no process for preparing HFC-1336 from HCFC-123 has been known.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a process for preparing HFC-1336 from HCFC-123 in a high yield.
Another object of the present invention is to provide a process for preparing HFC-356mff by further reacting HFC-1336 which is obtained by the above process with hydrogen.
According to the present invention, there is provided a process for preparing HFC-1336 comprising reacting HCFC-123 with copper, in particular, metal copper and an amine.
Further, according to the present invention, there is provided a process for preparing HFC-356mff comprising reacting HFC-1336 which is prepared by the above process with hydrogen.
The processes of the present invention are based on the finding that, when HCFC-123 is reacted with metal copper and an amine, unexpectedly, a reductive coupling reaction takes place, and HFC-1336 is readily formed in a good yield.
DETAILED DESCRIPTION OF THE INVENTION
In the process of the present invention, HCFC-123 as the starting material is known to be easily prepared at a low cost.
As the copper to be used in the present invention, metal copper, that is, copper having the valency of 0 (zero) is preferably used. In view of a speed of the reaction, a preferred shape of copper is a flake-shape, a granule, or a powder.
An amount of copper is not critical. Preferably, copper is used in a molar amount equal to, or one to 5 times larger than the amount of HCFC-123.
A kind of the amine to be used in the present invention is not limited and can be selected from a wide variety of amines. Preferred examples of the amine are aliphatic primary amines such as methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, sec.-butylamine, octylamine, etc.; aliphatic secondary amines such as dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, dioctylamine, etc.; aliphatic tertiary amines such as trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, trioctylamine, etc.; cyclic amines such as morpholine, piperazine, piperidine, pyrrolidine, etc.; alkanolamines such as mono-, di- and triethanolamines; and ammonia.
Among them, the aliphatic primary amines such as methylamine, ethylamine, propylamine, butylamine, sec.-butylamine, etc., and the aliphatic secondary amines such as dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, etc. are preferred.
An amount of the amine used in the present invention is not limited. Preferably, the amine is used in a molar amount equal to, or one to 5 times larger
REFERENCES:
patent: 2550953 (1951-05-01), Barrick
patent: 4739123 (1988-04-01), Furutaka et al.
patent: 4760208 (1988-07-01), Saran
patent: 5382720 (1995-01-01), Ikawa et al.
Daikin Industries Ltd.
Evans Joseph E.
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