Patent GB-949981-A (GB)
Title: Process for the preparation of substituted succinic acid compounds
IPC: C07C57/13
Filed: 1961-03-06
Abstract: Hydrocarbon-substituted succinic anhydrides are obtained by preparing a mixture of an olefin polymer and maleic anhydride, and contacting said mixture at a temperature above about 140 DEG C., preferably in the range of 160 DEG C. to 250 DEG C., with at least about one mole of chlorine for each mole of maleic anhydride. The olefine polymers include principally homopolymers of ethylene, propene, isobutene, and n-butene and copolymers of such olefins with higher mono- or di-olefines such as hexene, cyclohexene, butadiene, isoprene, chloroprene, styrene, or piperylene. The molecular weight of the polymers vary from 100 to 50,000 or even higher. Polyisobutenes in the range 500 to 3000 are preferred. Examples (3), (4) and (5) describe the use of propylene tetramer to prepare propylene tetramer substituted succinic anhydride. Acylated polyamines may be made by reacting a hydrocarbon-substituted succinic anhydride with an ethylene amine of the formula H2N(CH2CH(R)NH)xH under dehydrating conditions, where X is an integer and R is hydrogen or an alkyl radical. Suitable amines, which may be made by reaction of ethylene dichloride and ammonia, include ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine and cyclic condensation products such as piperazines.  At least one half, and preferably one, equivalent amount of the amine based on the nitrogen content, is used per equivalent of substituted succinic anhydride. Temperatures within the range of 80 DEG  to 200 DEG C. are satisfactory.  Advantageously, the water is removed by azeotropic distillation using toluene.ALSO:Hydrocarbon-substituted succinic anhydrides are obtained by preparing a mixture of an olefin polymer and maleic anhydride, and contacting said mixture at a temperature above about 140 DEG C., preferably in the range of 160 DEG  to 250 DEG C., with at least about one mole of chlorine for each mole of maleic anhydride.  The olefinic polymers include principally homopolymers of ethylene, propene, isobutene, and n-butene and copolymers of such olefines with higher mono- or di-olefines such as hexene, cyclohexene, butadiene, isoprene, chloroprene, styrene or piperylene. The molecular weights of the polymers vary from 100 to 50,000 or even higher. Polyisobutenes in the range 500 to 3,000 are preferred. Examples (1), (2) and (6) describe the use of polyisobutenes of M.W. 900 or 1,000 to form substituted succinic anhydrides. Acylated polyamines may be made by reacting a hydrocarbon-substituted succinic anhydride with an ethylene amine of the formula H2N(CH2CH(RNH)xH under dehydrating conditions, where x is an integer and R is hydrogen or an alkyl radical.  At least one half, and preferably one, equivalent of the amine based on the nitrogen content, is used per equivalent of substituted succinic anhydride.  Temperatures within the range of 80 DEG  to 200 DEG C. are satisfactory. Advantageously, the water is removed by azeotropic distillation using toluene.ALSO:Low molecular weight (e.g. 150-300) hydro-carbon-substituted succinic anhydrides are effective as rust-inhibiting additives in gasolines, fuel oils, cutting oils and engine lubricants, when used in amount of 0.001-0.5% by weight. As an example, 0.02% by weight of a propylene-tetramer-substituted succinic anhydride is added to a catalytically cracked Number 2 light fuel oil.  Metal salts, amides and ammonium salts of higher molecular weight hydrocarbon-substituted succinic anhydrides are useful as dispersing agents in hydrocarbon oil compositions in amounts from 0.5 to 5% by weight of the composition.  In an example, the reaction product of polyisobutenyl succinic anhydride and a mixture of diethylene triamine and triethylene tetramine is added to an S.A.E.20 lubricating oil containing zinc dialkylphosphorodithioate, polyalkylsiloxane, and sulphate ash as a basic barium salt of an organic phosphorus acid prepared by reacting polyisobutene, PCl3 and an alkyl phenol.