Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1997-10-20
1998-09-22
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C07C 4100
Patent
active
058115960
DESCRIPTION:
BRIEF SUMMARY
TECHNOLOGICAL FIELD
The present invention relates to a method of producing fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether, which is widely used as pharmaceutical and agrichemical products or intermediates thereof.
BACKGROUND TECHNOLOGY
As methods of producing fluoromethyl 1,1,1,3,3,3- hexafluoroisopropyl ether, there are known a method in which a mixture of concentrated sulfuric acid, hydrogen fluoride, paraformaldehyde and 1,1,1,3,3,3-hexafluoroisopropyl alcohol (hereinafter referred to as "HFIPA") is heated, and then the generated gas is trapped (U.S. Pat. No. 4,469,898), and another method in which trioxane is added to hydrogen fluoride, and then HFIPA is added thereto (JP-T-7-502037), and other methods. However, various kinds of polyethers are produced as by-products, or their yields are very low. These polyethers are separated from fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether by distillation, and then are discarded.
Furthermore, there is also known a method in which chloromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether is fluorinated by potassium fluoride at high temperature and high pressure. However, the reaction conditions are severe, and furthermore the yield is merely 60%.
DISCLOSURE OF THE INVENTION
The present inventors have examined a method of producing fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether from formaldehyde or its polymer in high yield. With this, we found that it is possible to produce fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether from a polyether represented by the general formula (1): alkyl or haloalkyl groups (halogen is fluorine, chlorine or bromine), n is an integer of from 1 to 10, and both of R.sup.1 and R.sup.2 are not hydrogen at the same time). Thus, we achieved the present invention.
That is, the present invention provides a method of producing fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether by bringing a polyether represented by the general formula (1) into contact with a medium comprising hydrogen fluoride and an accelerant,
Furthermore, the present invention provides a method of producing fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether by bringing a polyether represented by the general formula (1) and optionally 1,1,1,3,3,3-hexafluoroisopropyl alcohol into contact with a medium comprising hydrogen fluoride, an accelerant and optionally formaldehyde.
Concrete examples of R.sup.1 and R.sup.2 are alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, t-butyl, pentyl, hexyl, heptyl and octyl, and residues which are isomers thereof, although they are not exemplified.
Furthermore, examples of the haloalkyl groups, in which fluorine and/or chlorine has been substituted for at least one hydrogen of these alkyl groups, are fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, 1-fluoroisopropyl, 1,1- difluoroisopropyl, 1,1,1-trifluoroisopropyl, 1,1,1,2-tetrafluoro-isopropyl, pentafluoroisopropyl, hexafluoroisopropyl, and the like.
It is particularly preferable that at least one of R.sup.1 and R.sup.2 is fluoromethyl group or hexafluoroisopropyl group.
Polyoxymethylene group is represented by a straight chain in the general formula, but it may be in the form of ring. It is not necessary to particularly limit the unit number (n) of oxymethylene group. However, if it is too large, its behavior will become substantially similar to that of formaldehyde polymer in case that the present invention's method is applied. Thus, it becomes necessary to increase the amount of the after-mentioned HFIPA to be added. With this, the use of a polyether of the general formula (1) does not make sense very much.
Concrete examples of polyethers of the general formula (1), which are preferably applied to the present invention's method, are: integer of from 1 to 10, from 1 to 10, and from 1 to 10. integer of from 1 to 7, from 1 to 6, and from 1 to 4.
The method of producing polyether of the general formula (1) is not limited, and its production method is nonlimitatively exemplified, as follows. R.sup.3 is a C.sub.1 -C.sub.10 alkyl o
Kawai Toshikazu
Watanabe Mineo
Central Glass Co. Ltd.
Geist Gary
Puttlitz, Jr. Karl J.
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