Patent GB-935534-A (GB)
Title: Method of forming a cyanoalkylsilane and catalyst therefor
IPC: C08G77/00
Filed: 1959-12-07
Abstract: A catalyst composition used in the preparation of beta-cyanoalkylsilanes (see Group IV(a)), comprises (A) a cuprous halide or cuprous oxide, (B) a di- or tri-amine of the formula RR1N(CH2)mN(R1)2 where m is 1 to 6, R is alkyl and R1 is hydrogen, alkyl, aminoalkyl or dialkylaminoalkyl, and preferably (C) a trialkylamine; the total number of nitrogen atoms in the composition being greater than the number of copper atoms.  Examples of component (B) include, inter alia, N,N,N1,N1-tetramethylethylene diamine, N,N-dimethyl-N,N1-diethylethylene diamine, N,N-dimethylethylene diamine, N,N,N1-trimethyl-N1-octylethylene diamine, N,N,N1,N11,N11-pentamethyldiethylene triamine, N,N,N1,N1-tetramethyl-methylene and -propylene diamines, N,N,N1-trimethyldiethylene triamine and N-methylhexamethylene diamine.  Specified trialkylamines (C) are tri-methyl-, -ethyl, -butyl, -amyl, -octyl amines, methyldiethyl-, dimethyl butyl-, methyl butyloctyl- and dimethyl octadecyl-amines.  The preferred proportions are 0,1 to 20 moles each of (A) and (B) and 0 to 20 moles of (C).  In (A) the number of moles is based on the formula CuX or CuO 1/2 , X being halogen.ALSO:Beta-cyanoalkyl silanes containing 1 or 2 cyanoalkyl groups, 1 to 3 silicon-bonded halogen atoms, up to 2 silicon-bonded hydrogen atoms and 0 or 1 silicon-bonded hydrocarbon or substituted hydrocarbon radical, are prepared by reacting the appropriate silicon hydride with an alpha-, beta-unsaturated olefinic nitrile in the presence of a catalyst composition comprising (A) a cuprous halide or cuprous oxide, (B) a di- or tri-amine of the formula RR1N(CH2)mN(R1)2 where m is 1 to 6, R is alkyl and R1 is hydrogen, alkyl, aminoalkyl or dialkylaminoalkyl, and preferably (C) a trialkylamine; the total number of nitrogen atoms in the catalyst composition being greater than the number of copper atoms.  Examples of component (B) include, inter alia, N,N,N1,N1-tetramethylethylene diamine, N,N-dimethyl-N,N1-diethylethylene diamine, N,N-dimethylethylene diamine, N,N,N1-trimethyl-N1-octylethylene diamine, N,N,N1,N11-N11-pentamethyldiethylene triamine, N,N,N1,-N1-tetramethyl-methylene and -propylene diamines, N,N,N1-trimethyldiethylene triamine and N-methylhexamethylene diamine.  Specified trialkylamines (C) are tri-methyl, -ethyl, -butyl, -amyl, -octyl amines, methyldiethyl-, dimethylbutyl-, methylbutyloctyl- and dimethyloctadecylamines. The preferred proportions are 0,1 to 20 moles each of (A) and (B), and 0 to 20 moles of (C).  In (A) the number of moles is based on the formula CuX or <FORM:0935534/IV(a)/1> X being halogen.  Many examples are given describing the preparation of beta-(CN-Et)MeSiCl2, beta-(CN-Pr)MeSiCl2, beta-(CN-Et)PhSiCl2, and beta-(CN-Et)SiCl3.  The difunctional beta-cyanoalkyl silanes may be converted to silicone oils and elastomers; e.g. equal parts of (CN-Et)MeSiCl2 and Me2SiCl2 are cohydrolysed to form an oil which may be converted to a gum by heating with KOH; this gum being milled with silica aerogel and benzoyl peroxide and heated to form a rubber.  The beta-cyanoalkyl trichlorosilanes may also be cohydrolysed with other halosilanes to form oils and resins.  Uses: Lubricants, hydraulic fluids, gaskets.