Patent GB-1094376-A (GB)
Title: Halogenated polyethers
IPC: C07C43/29
Filed: 1964-12-04
Abstract: Liquid partially fluorinated polyphenyl ethers of the general formula <FORM:1094376/C4-C5/1> in which R is a monocyclic aryl group free from olefinic and acetylenic unsaturation and having 6 to 12 carbon atoms, R1 is a monocyclic arylene group free from olefinic and acetylenic unsaturation and having 6 to 12 carbon atoms, n is an integer not exceeding 5, at least one of X1, X2, X3, X4 and X5 is a fluorine atom, the remainder being fluorine or hydrogen atoms or groups having the general formula -OR1OR, in which R and R1 are as above defined, not more than two of X1, X2, X3, X4 and X5 being ROR1O-groups, are used as lubricants, hydraulic fluids, or heat transfer media.ALSO:The invention relates to a partially fluorinated aromatic ether in which the fluorine atom or atoms are all present as nuclear substituents in one aryl group containing at least 6 but not more than 12 carbon atoms and which may also contain an alkyl group as substituent, the aryl group being free from olefinic and acetylenic unsaturation and having at least one but not more than three substituents therein having one of the formulae RO- or R(OR1)nO- in which R is an aryl group which is free from olefinic and acetylenic unsaturation and has 6-12 carbon atoms, R1 is an arylene group which is free from olefinic and acetylenic unsaturation and has 6-12 carbon atoms and n is an integer not exceeding 5 and the total number of fluorine and oxygen atoms in the ether is at least 3.  The invention also relates to fluorinated aromatic polyethers having the general formula <FORM:1094376/C2/1> in which R is a monocyclic aryl group free from olefinic and acetylenic unsaturation and having 6-12 carbon atoms, R1 is a monocyclic arylene group free from olefinic and acetylenic unsaturation and having 6-12 carbon atoms, n is an integer not exceeding 5, at least one of X1, X2, X3, X4 and X5 is a fluorine atom, the remainder being fluorine or hydrogen atoms or groups having the general formula -OR1OR, in which R and R1 are as above defined, not more than two of X1, X2, X3, X4 and X5 being RORO- groups. Polyethers claimed per se are meta - (meta - fluorophenoxy)phenyl metaphenoxyphenyl ether, meta - (para - fluorophenoxy)phenyl meta - phenoxyphenyl ether, 1 - [meta - (pentafluorophenoxy)phenoxyl]-3-) meta - phenoxyphenoxy)benzene, 1,3,5-tris-(meta - phenoxyphenoxy)trifluorobenzene, pentafluorophenyl meta - phenoxyphenyl ether, meta - (pentafluorophenoxy)phenyl meta-phenoxyphenyl ether.  The partially fluorinated aromatic ethers may be prepared by reacting a polyfluorinated aryl hydrocarbon, e.g. hexafluorobenzene or decafluorodiphenyl which is free from olefinic and acetylenic unsaturation and has 6-12 carbon atoms to 5-10 fluorine atoms with an alkali metal salt of a phenol having one of the formulae ROX and R(OR1)nOX in which R is an aryl group which is free from olefinic and acetylenic unsaturation and has 6-12 carbon atoms, R1 is an arylene group which is free from olefinic and acetylenic unsaturation and has 6-12 carbon atoms, n is an integer not exceeding 5 and X is an alkali metal atom,  the latter being supplied in an amount sufficient to replace 1 to 3 fluorine atoms. The monofluorinated aromatic ethers may be prepared by reacting a monofluorinated aryl hydrocarbon containing one fluorine atom in the nucleus and one chlorine, bromine or iodine atom with an alkali metal salt of a phenol having one of the formulae R(OR1)nOX in which R, R1, X and n are defined as above under the conditions of the Ullmann reaction. Several examples are given.