Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1984-09-11
1988-04-05
Sutto, Anton H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549428, 549504, 549511, 568615, 568683, C07D31912, C07D30748, C07C 4311, C07C 4312
Patent
active
047360453
DESCRIPTION:
BRIEF SUMMARY
This invention relates to certain fluorinated ethers and to the use of the fluorinated ethers in a number of diverse fields, especially as inert fluids, for example the working fluid of a heat pump.
The invention relates to novel fluorinated ethers which are the product of a fluorination reaction of an adduct formed by the free-radical addition of a fluoro-olefin and a hydrogen-containing ether. The fluorinated ether may be partially or fully fluorinated during the fluorination reaction. The hydrogen-containing ether is preferably of the formula R--O--R' wherein R and R' are hydrocarbon groups optionally substituted by chlorine or fluorine or together form a single hydrocarbon group and the total number of carbon atoms in the groups R and R' is preferably less than 10; specifically groups R and R' may be the same or different and maybe selected from alkyl, cycloalkyl, aralkyl and aryl, provided that both groups are not aryl. The preferred alkyl groups are methyl, ethyl and propyl but may also be butyl or larger groups.
Among the preferred hydrogen-containing ethers which may be used in accordance with the present invention are dimethyl ether, diethyl ether, dipropyl ether, tetrahydrofuran, dioxane, tetrahydropyran, trimethylene oxide, or ethylene glycol dimethyl ether.
The preferred fluoro-olefin is tetrafluoro-ethylene. Other fluoro-olefins which may be used are difluoroethylene, chlorotrifluoroethylene,perfluorcyclobutene, trifluroethylene and hexafluoropropene. The mole ratio of the fluoro-olefin and the hydrogen-containing ether in the adduct may be from 6:1 to 1:1, but in certain instances may involve a larger amount of fluoro-olefin. For many working fluid applications, particularly for heat pump applications, it is preferred that the ratio of fluoro-olefin to the hydrogen-containing ether in the adduct is 2:1 or 1:1. The fluorinated ether according to the present invention may be one of the following compounds: ##STR1##
In the above formulae the symbol F in the centre of the rings depicted indicates that all unmarked bonds are to fluorine atoms. This designation is used throughout the specification.
The present invention also includes a process for making fluorinated ethers as described above wherein the fluorination of the adduct is effected by the use of a high valency metal fluoride as a fluorinating agent at a temperature above 200.degree. C. A fluorination procedure of this general kind is described in "Advances in Fluorine Chemistry" Vol. 1. Butterworth, 1960 P 166. Cobalt trifluoride alone or in association with alkali or alkaline earth metal fluorides such as potassium fluoride or calcium fluoride are the preferred fluorinating agents. In the process of this invention, the fluorination is preferably effected in the temperature range 300.degree. C. to 600.degree. C. eg. at temperatures between 400.degree. C. to 500.degree. C.
The present invention is concerned with compounds which have good stability and by suitable selection compounds are provided for use as inert fluids and in particular for the working fluid of a heat pump. Furthermore, compounds may be selected which are particularly useful as heat pipe fluids, as coolants, as heat absorption media eg. for geothermal heat recovery, as lubricants, in vapour phase soldering, as solvents, especially in the separation of ethyl alcohol from aqueous mixtures, or as dielectrics. Several of these uses require the fluorinated ether to have particularly high stability, which is a feature of the compounds of this invention. Furthermore, the use of partly fluorinated compounds as starting materials for the fluorination reaction in some cases substantially avoids, and not merely inhibits fragmentation of the adducts: additionally the fluorine containing adducts used in accordance with this invention permit controlled yields to be obtained with respect to various fluorinated ethers. It is known (see Journal of Fluorine Chemistry 1975 5 p 521-Brandwood, Coe, Ely and Tatlow) that the usual experience with fluorination of hydrocarbon material containing n
REFERENCES:
patent: 2644823 (1953-07-01), Kauck et al.
patent: 3816286 (1974-06-01), Haszeldine et al.
Chambers et al., J. Fluorine Chemistry, 16(4), pp. 351-364 (1980).
Chambers Richard D.
Drakesmith Frederick G.
Grievson Brian
Powell Richard L.
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