GB715947A - Manufacture of fluorinated carbocyclic compounds and derivatives thereof - Google Patents

Abstract

Heptafluoroadipic acid and derived fluoroamines or fluoroalcohols can produce highly fluorinated polymers. Products with alternating fluorine-containing and hydrogen-containing residues may be obtained by condensing the acid with hexamethylene diamine, and ethylene glycol.ALSO:Benzene is fluorinated to produce a mixture of partially fluorinated cyclohexanes by heating in the vapour phase with a reactive metal fluoride not above 300 DEG C. and the products are fractionally distilled. The products may, without separation, be treated with an oxidizing agent to give a partially fluorinated aliphatic dicarboxylic acid, or the individual fluorocyclohexanes may be heated with aqueous alkali to give fluorinated cyclohexenes which on oxidation give fluorinated aliphatic dicarboxylic acids. In an example, benzene is treated with cobalt trifluoride at 150 DEG C. and the products distilled; the products are refluxed with permanganate and acidified to give heptafluoroadipic acid, which can be converted into various derivatives; the fractional separation of the initial products gives undecafluorocyclohexane, decafluorocyclohexane, nona- and octa fluorocyclohexanes; undecafluorocyclohexane refluxed with alkali gives perfluorocyclohexene; the deca product gives nonafluorocyclohexene with alkali; an isomeric deca-product gives perfluorocyclohexadiene; perfluorocyclohexene on oxidation with permanganate gives perfluoroadipic acid; nonfluorocyclohexene on oxidation gives heptafluoroadipic acid; perfluorocyclohexadiene oxidized to perfluorosuccinic acid. Derivatives of the aliphatic dibasic acids referred to include the bis-aniline salts, diethyl esters and diamides, fluoroamines, fluoroalcohols and products by condensation of the acids with hexamethylene diamine, and ethylene glycol.