GB1314700A - Method of preparing amine derivatives - Google Patents

Abstract

1314700 Forminino esters; thioforminino esters; amidines CHEVRON RESEARCH CO 4 Dec 1970 [12 Dec 1969] 57832/70 Headings C2C and C2U [Also in Divisions C3 and C5] Compounds of the formula R<SP>1</SP>(N=CH.XR) n , where X is 0 or 5, R is a hydrocarbon group of 1-300 carbon atoms, n is 1-50, R<SP>1</SP> is a mono- or polyvalent hydrocarbon radical having saturated aliphatic carbon atoms attached to the nitrogen atom(s), and contains 2-300 carbon atoms when n is 1, and 5-7150 carbon atoms when n is 2-50, are prepared by reacting a non-conjugated hydrocarbon olefin of molecular weight 28 to 500,000, and having 1-50 sites of olefinic unsaturation, and which is either a mono-olefin of 2-300 carbon atoms or a polyolefin of 5-7150 carbon atoms, with HF, HCN and RXH, R being bonded to X, when oxygen, by means of an aromatic carbon atom or by an aliphatic carbon atom which is itself bonded to at least one hydrogen atom and not to an aryl group; the molar ratio of HCN to olefin being 0À5-20 : 1, the molar ratio of RXH to olefin being 0À9-10 : 1, and the molar ratio of HF to HCN being 1-10 : 1. Inert solvents may be used. Specified olefins are ethylene, propylene, butene-1, butene-2, isobutylene, octene-1, 1,5-hexadiene, 1,7-octadiene, decene-1, decene-2, octadecene-1, tripropylene, tetrapropylene, diisobutylene, triisobutylene, tetraisobutylene, polyisobutylene of from about 420 to 5000 molecular weight, polypropylene of for example from about 300 to 5000 molecular weight, allylbenzene, allylnaphthalene, 4- methylpentene-1, eicosene, triacontene, tetracontene, cyclohexene, menthene, octahydronaphthalene, cyclooctene, vinyleyclohexane, methylenecyclopentane, vinylcyclohexane, copolymer of isoprene and stryrene, and 3- cholestene. Specified compounds RXH are methanol, ethanol, propanol, isopropanol, hexanol, fusel oil alcohols, octanol, dodecanol, eicosanol, cholesterol, cyclohexanol, cyclopentanol, cyclooctanol, phenol, tert.-butylphenol, cresol, xylenol, naphthol, phenylethanol, methyl thiol, ethyl thiol, thiophenol, thionaphthol, cyclohexane thiol and benzyl thiol. The products form amidines when reacted with amines; specified amines are methylamine, diethylamine, stearylamine, abietylamine, aniline, benzylamine, ethylene diamine, triethylene tetramine, tetraethylene pentamine, piperazine, morpholine, N,N<SP>1</SP>-diethyl ethylene diamine, N-octadecyl propylene diamine, N-oleyl ethylene diamine and cholesterylamine. The amidines may be used as lubricant additives.