Organic compounds -- part of the class 532-570 series – Organic compounds – Halogen containing
Patent
1994-08-24
1996-09-17
Evans, Joseph E.
Organic compounds -- part of the class 532-570 series
Organic compounds
Halogen containing
570134, 570172, C07C 17093, C07C 17278, C07C 1901, C07C 1908
Patent
active
055570194
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP93/00214 filed Feb. 22, 1993, and published as WO93/16973 Sep. 2, 1993.
APPLICABLE FIELD TO THE INDUSTRY
The present invention relates to a production method of 1,1,1,2,2,4,4,5,5,5-decafluoropentane (HFC-43-10 mcf) as an alternative compound of CFC and HCFC used for refrigerants, foaming agents, and cleaning agents, and its intermediate product (precursor) for the production method or 3,3-dichloro-1,1,1,2,2,4,4,5,5,5-decafluoropentane (and 2,2-dichloro-1,1,1,3,3,4,4,5,5,5-decafluoropentane) very effective as an intermediate of a monomer during production of macromolecular fluorocompounds and many intermediate products of fluorocompounds.
PRIOR ART
Decafluoropentane can be as an alternative (alternative freon) of CFC and HCFC used for refrigerants, foaming agents, and cleaning agents. In particular, HFC-43-10 mcf, like conventionally used freon, is expected to be applied for foam agents, refrigerants, and cleaning agents, and has an advantage not to destroy the ozone layer in the stratosphere because of no chlorine.
However, a production method of HFC-43-10 mcf has not been completely known in the past. Raw materials to synthesize such decafluoropentane have not been studied.
OBJECT OF THE INVENTION
The object of the invention is to provide a new compound to synthesize the said decafluoropentane and a production method to give the said new product at high yield and high selectivity.
Further object of the invention is to provide a production method of HFC-43-10 mcf at high yield and industrial scale economically.
COMPOSITION OF THE INVENTION
The first invention of the present application relates to 3,3-dichloro-1,1,1,2,2,4,4,5,5,5-decafluoropentane (and 2,2-dichloro-1,1,1,3,3,4,4,5,5,5-decafluoropentane).
The second invention of the present application relates to a production method of 3,3-dichloro-1,1,1,2,2,4,4,5,5,5-decafluoropentane (and 2,2-dichloro-1,1,1,3,3,4,4,5,5,5-decafloropentane) characterized by reaction of tetrafluoroethylene and difluorodichloromethane under Lewis acid catalyst.
In this case, it is desirable to react the reactants contacting Lewis acid at gaseous and liquid phases at -20.degree. to +100.degree. C.
2,2-dichloro-1,1,1,3,3,4,4,5,5,5-decafluoropentane and 3,3-dichloro-1,1,1,2,2,4,4,5,5,5-decafluoropentane related to the above first invention are new products shown by the following chemical formulas: ##STR1##
These new products are very useful, as they are, as intermediates of monomers to produce macromolecular fluorocompounds and many intermediate compounds of fluorocompounds, and they can be converted by reduction into decafluoropentane, as shown by the following formulas, usable for alternatives of CFC and HCFC (alternative freon) applying for refrigerants, foaming agents, and cleaning agents. ##STR2##
Referring to the first invention, 2,2-dichloro-1,1,1,3,3,4,4,5,5,5-decafluoropentane and 3,3-dichloro-1,1,1,2,2,4,4,5,5,5-decafluoropentane are new materials with boiling point of 90.degree. C. and are very useful as described above, but their effective production methods are unknown.
However, the present inventors studied hard the effective production method of 2,2-dichloro-1,1,1,3,3,4,4,5,5,5-decafluoropentane and 3,3-dichloro-1,1,1,2,2,4,4,5,5,5-decafluoropentane and found that tetrafluoroethylene and difluorodichloromethane react under the presence of Lewis acid catalysts as shown below to produce 2,2-dichloro-1,1,1,3,3,4,4,5,5,5,-decafluoropentane and 3,3-dichloro-1,1,1,2,2,4,4,5,5,5-decafluoropentane at high yield to arrive at the production method of the said second invention. ##STR3##
The Lewis acid catalyst used for the invention may be selected from titanium tetrachloride anhydride, zirconium tetrachloride anhydride, tin tetrachloride anhydride, antimony pentachloride anhydride, zinc chloride anhydride, iron chloride anhydride, aluminum bromide anhydride, and boron trifluoride as well as aluminum chloride anhydride.
The catalyst may be selected from metallic chlorofluoride catalyst of aluminum-, zirconium-and titanium-chlorof
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Aoyama Hirokazu
Kohno Satoru
Koyama Satoshi
Daikin Industries Ltd.
Evans Joseph E.
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