1332201 Alkylated diphenylamines CIBAGEIGY (UK) Ltd 25 Jan 1972 [26 Jan 1971] 3159/71 Heading C2C [Also in Division C5] The invention comprises compounds of formula in which R 1 is a C 1 -C 4 alkyl group, R 2 is methyl and R 3 is a cycloalkyl or cycloalkenyl radical having 5-12 carbon atoms being either unsubstituted or substituted with an alkyl group, or in which R 2 and R 3 , together with the carbon atom to which they are attached form a carbocyclic ring system having from 5 to 12 carbon atoms in the ring, the ring being either unsubstituted or substituted with an alkyl group. The compounds are prepared by alkylating diphenylamine with an appropriate olefin, cyclopropane or cyclobutane in the presence of a Friedel Crafts catalyst which may be a Lewis acid (e.g. AlCl 3 or ZnCl 2 ) or a Bronsted acid (acid washed Montmorillonite), the reaction being carried out preferably by heating in the presence of an inert organic solvent. The compounds of the invention are useful as antioxidants for a wide variety of listed organic materials especially synthetic lubricants. Examples of the compounds of the invention are p,pSP1/SP - di - (1 - methylcyclohexyl)diphenylamine, p,pSP1/SP - di - (1 - methyl - 4 - isopropylcyclohex - 1- enyl - 4)diphenylamine, p,pSP1/SP - di - (2 - methyl- 4 - isopropylcyclohex - 1 - enyl - 4)diphenylamine, p,pSP1/SP - di - (2 - methyl - 3 - isopropylcyclohex - 1 - enyl - 3)diphenylamine, p,pSP1/SP - di- (1 - isopropyl - 4 - methylcyclohexyl)diphenylamine, p,pSP1/SP - di - (1 - isopropyl - 3 - methylcyclohexyl)diphenylamine, p,pSP1/SP - di[ - methyl - (1- methylcyclohexen - 1 - yl - 4)ethyl]diphenylamine and p,pSP1/SP - di - (1 - methyl - 4 - isopropenylcyclohexyl)diphenylamine.
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