US 5,621,147 AGranted

Trifluoro-2-(trans-4-substituted cyclohexyl) ethylenes and process for their production

AssigneeAsahi Glass Company, Limited

InventorsOsamu Yokokoji, Tamaki Simizu, Seisaku Kumai

Life of this patent

Estimating the term…

Loading patent…

Abstract

A 1,1,2-trifluoro-2-(trans-4-substituted cyclohexyl)ethylene of the formula (1): R--(A).sub.m --Cy--CF=CF.sub.2 (1) wherein R is a C.sub.1-10 alkyl group, a halogen atom or a cyano group, provided that in the case of the alkyl group, an oxygen atom may be interposed in a carbon-carbon bond of the alkyl group or in a carbon-carbon bond between this alkyl group and A, some of carbon-carbon bonds in the alkyl group may be triple bonds or double bonds, one --CH.sub.2 -- group in the alkyl group may be substituted by a carbonyl group, and some or all of hydrogen atoms in the alkyl group may be substituted by fluorine atoms; Cy is an unsubstituted trans-1,4-cyclohexylene group; A is a trans-1,4-cyclohexylene group, a 1,4-phenylene group or a 1,4-cyclohexenylene group, wherein each of such cyclic groups is unsubstituted or substituted by one or more halogen atoms or cyano groups, one or more =CH-- groups constituting rings of such cyclic groups may be substituted by nitrogen atoms, and one or more --CH.sub.2 -- groups constituting rings of such cyclic groups may be substituted by oxygen atoms or sulfur atoms; and m is 0 or 1.

Claims10

Dependent claims

A 1,1,2-trifluoro-2-(trans-4-substituted cyclohexyl)ethylene of the formula (1):

R--(A).sub.m --Cy--CF=CF.sub.2 ( 1)
wherein R is a halogen atom, a cyano group, a C.sub.1-10 alkyl group, a C.sub.1-10 alkyl group wherein at least one hydrogen atom is replaced with a fluorine atom, a C.sub.1-10 alkoxyl group, a C.sub.1-10 alkoxyl group wherein at least one hydrogen atom is replaced with a fluorine atom, a C.sub.1-10 alkenyl group containing at least one carbon-carbon double bond, a C.sub.1-10 alkenyl group containing at least one carbon-carbon double bond and wherein at least one hydrogen atom is replaced with a fluorine atom, a C.sub.1-10 alkynyl group containing at least one carbon-carbon triple bond, a C.sub.1-10 alkynyl group containing at least one carbon-carbon triple bond and wherein at least one hydrogen atom is replaced with a fluorine atom, a C.sub.1-10 alkyl group containing therein one carbonyl group, or a C.sub.1-10 alkyl group containing therein one carbonyl group and wherein at least one hydrogen atom is replaced with a fluorine atom;
Cy is an unsubstituted trans-1,4-cyclohexylene group;
A is a trans-1,4-cyclohexylene group, a trans-1,4-cyclohexylene group substituted with at least one halogen atom or cyano group, a trans-1,4-cyclohexylene group wherein at least one --CH.sub.2 -- group is replaced by an oxygen or sulfur atom, a trans-1,4-cyclohexylene group wherein at least one =CH-- group is replaced by a nitrogen atom, a trans-1,4cyclohexylene group substituted with at least one halogen atom or cyano group and wherein at least one --CH.sub.2 -- group is replaced with an oxygen or sulfur atom, a trans-1,4-cyclohexylene group substituted with at least one halogen atom or cyano group and wherein at least one =CH-- group is replaced by a nitrogen atom, a 1,4-phenylene group, a 1,4-phenylene group substituted with at least one halogen atom or cyano group, a 1,4-phenylene group wherein at least one =C-- group is replaced with a nitrogen atom, a 1,4-phenylene group substituted with at least one halogen atom or cyano group and wherein at least one =C-- group is replaced with a nitrogen atom, a 1,4-cyclohexenylene group, a 1,4-cyclohexenylene group substituted with at least one halogen atom or cyano group, a 1,4-cyclohexenylene group wherein at least one --CH.sub.2 -- group is replaced with an oxygen or sulfur atom, a 1,4-cyclohexenylene group wherein at least one =CH-- group is replaced with a nitrogen atom, a 1,4-cyclohexenylene group substituted with at least one halogen atom or cyano group and wherein at least one --CH.sub.2 -- group is replaced with an oxygen or sulfur atom, or a 1,4-cyclohexenylene group substituted with at least one halogen atom or cyano group and wherein at least one =CH-- group is replaced with a nitrogen atom;
and
m is 0 or 1.

3 more elements

A process for producing a 1,1,2-trifluoro-2-(trans-4-substituted cyclohexyl)ethylene of the formula (1), which comprises fluorinating a compound of the formula (13) to obtain a compound of the formula (14), and further dehydrofluorinating the compound of the formula (14):

R--(A).sub.m --Cy--CH=CF.sub.2 ( 13)
R--(A).sub.m --Cy--CHFCF.sub.3 ( 14)
R--(A).sub.m --Cy--CF=CF.sub.2 ( 1)
wherein R is a halogen atom, a cyano group, a C.sub.1-10 alkyl group, a C.sub.1-10 alkyl group wherein at least one hydrogen atom is replaced with a fluorine atom, a C.sub.1-10 alkoxyl group, a C.sub.1-10 alkoxyl group wherein at least one hydrogen atom is replaced with a fluorine atom, a C.sub.1-4 alkenyl group containing at least one carbon-carbon double bond, a C.sub.1-10 alkenyl group containing at least one carbon-carbon double bond and wherein at least one hydrogen atom is replaced with a fluorine atom, a C.sub.1-10 alkynyl group containing at least one carbon-carbon triple bond, a C.sub.1-10 alkynyl group containing at least one carbon-carbon triple bond and wherein at least one hydrogen atom is replaced with a fluorine atom, a C.sub.1-10 alkyl group containing therein one carbonyl group, or a C.sub.1-10 alkyl group containing therein one carbonyl group and wherein at least one hydrogen atom is replaced with a fluorine atom;
Cy is an unsubstituted trans-1,4-cyclohexylene group;
A is a trans-1,4-cyclohexylene group, a a trans-1,4-cyclohexylene group substituted with at least one halogen atom or cyano group, a trans-1,4-cyclohexylene group wherein at least one --CH.sub.2 -- group is replaced by an oxygen or sulfur atom, a trans-1,4-cyclohexylene group wherein at least one =CH-- group is replaced by a nitrogen atom, a trans-1,4,-cyclohexylene group substituted with at least one halogen atom or cyano group and wherein at least one --CH.sub.2 -- group is replaced with an oxygen or sulfur atom, a 1,4-phenylene group, a trans-1,4-cyclohexylene group substituted with at least one halogen atom or cyano group and wherein at least one =CH-- group is replaced with a nitrogen atom, a 1,4,-phenylene group, a 1,4-phenylene group substituted with at least one halogen atom or cyano group, a 1,4-phenylene group wherein at least one =C-- group is replaced with a nitrogen atom, a 1,4-phenylene group substituted with at least one halogen atom or cyano group and wherein at least one =C-- group is replaced with a nitrogen atom, a 1,4-cyclohexenylene group, a 1,4-cyclohexenylene group substituted with at least one halogen atom or cyano group, a 1,4-cyclohexenylene group wherein at least one --CH.sub.2 -- group is replaced with an oxygen or sulfur atom, a 1,4-cyclohexenylene group wherein at least one =CH-- group is replaced with a nitrogen atom, a 1,4-cyclohexenylene group substituted with at least one halogen atom or cyano group and wherein at least one --CH.sub.2 -- group is replaced with an oxygen or sulfur atom, or a 1,4-cyclohexenylene group substituted with at least one halogen atom or cyano group and wherein at least one =CH-- is replaced with a nitrogen atom;
and
m is 0 or 1.

5 more elements

Dependencies are inferred from the claim text.