Patent GB-1278072-A (GB)
Title: A process for preparing organosilicon compounds
IPC: C07F7/14
Filed: 1969-08-14
Abstract: 1278072 Hydrosilation of olefins TORAY INDUSTRIES Inc 14 Aug 1969 [26 Aug 1968 21 Sept 1968 26 Sept 1968] 40592/69 Headings C3P C3S and C3T [Also in Division C2] Organosilicon compounds are prepared by hydrosilating an olefinic double bond with a hydrosilane compound in the presence of a palladium catalyst in the zerovalent state having a trivalent phosphorus, arsenic or antimony compound as a ligand. Preferred ligands are those in which the P, As or Sb atom is attached to a halogen atom or to an amino, alkyl, cycloalkyl, aryl, alkoxy, cycloalkoxy or aryloxy group. The palladium source is preferably metallic palladium but may also be any palladium compound yielding metallic palladium under the reaction conditions. In addition to the preparation of monomeric silanes and siloxanes the process is also applicable to the preparation of polymeric compounds by reaction between a dihydrosilane and a polyolefin, or by reaction between an organosilicon polymer having a Si-H bond and an olefin monomer or polymer. Examples describe the preparation of 1 - (trichlorosilyl) - hexane, 1 - (trimethoxysilyl) - hexane, 1 - (triethylsilyl) - hexane, alpha- (trichlorosilyl) - propionitrile, alpha - (trichlorosilyl) - ethylbenzene, 1 - (triethoxysilyl)- hexane, alpha - (trimethylsilyl) - propionitrile, trichlorosilyl - ethane, 1 - (triethylsilyl) - octane, 1 - (trichlorosilyl) - 2 - butene, 1 - (trichlorosilyl) - 2 - methyl - 2 - butene, 1 - (trichlorosilyl) - propane, 1 - (trichlorosilyl) - butane, 1- (trichlorosilyl) - 2 - methylpropane, 1 - (trichlorosilyl) - pentane, 1 - (trichlorosilyl) - 2- methylpentane, 1 - (trichlorosilyl) - octane, 1- (trichlorosilyl) - decane, trichlorosilylcyclooctane, 1 - trichlorosilyl - 2 - (3 - cyclohexenyl)- ethane, 1 - chloro - 2 - (trichlorosilyl) - ethane, 1 - (trichlorosilyl) - 2 - acetoxyethane, 1 - (trichlorosilyl) - 2 - ethoxyethane, 1 - (trichlorosilyl) - 3 - ethoxypropane, allyltrichlorosilane, 1 - (dichloromethylsilyl) - hexane, 1 - (chlorodimethylsilyl) - hexane, tetramethyldiethyldisiloxane, dichlorodiethylsilane, dichlorohexylsilane, chlorotriethylsilane, chlorohexylsilane, dihexyltetramethyldisiloxane, dichlorodihexylsilane, chlorotrihexylsilane, 1 - (trichlorosilyl) - 2,3 - dimethyl - 2 - butene, 2- (trichlorosilyl) - 3 - pentene, 5 - (trichlorosilyl)- 1,6 - octadiene, 1 - (dichloromethylsilyl)- 2- butene, 1 - (chlorodimethylsilyl)- 2 - butene, 1- (dichloromethoxysilyl)- 2 - butene, 1 - (chlorodimethoxysilyl) - 2 - butene, 1 - (trimethoxysilyl) - 2 - butene, 1 - (dichlorosilyl) - 2 - butene, 1 - (chlorosilyl) - 2 - butene, 3 - (trichlorosilyl)- cyclooctene, resinous or glass polymers from 1,3,5,7 - tetramethyl - 1,3,5,7 - tetravinylcyclotetrasiloxane and 1,3,5,7-tetramethyl-1,3,5,7- tetrahydrocyclotetrasiloxane, 1,5 - dihydro- 1,3,3,5,7,7 - hexamethyl - cyclotetrasiloxane, or 1,5 - dimethyl - 1,5 - dihydro - 3,3,7,7 - tetraphenylcyclotetrasiloxane, a glassy polymer from 1,3,5,7 - tetramethyl - 1,3,5,7 - tetraallylcyclotetrasiloxane and 1,5 - diphenyl - 3,7- dimethyl - 1,3,5,7 - tetrahydrocyclotetrasiloxane, a glassy polymer from 1,5 - diallyl- 1,3,3,5,7,7 -hexamethyl - cyclotetrasiloxane and 1,3,5,7 - tetramethyl - 1,3,5,7 - tetrahydrocyclotetrasiloxane, a rubbery polymer from methylvinylpolysiloxane (consisting of 1 mol. per cent methylvinylsiloxane, 1 mol. per cent dimethyl vinylsiloxane and 98 mol. per cent dimethylsiloxane) and 1,1,3,3-tetramethyldisiloxane, a resinous polyadduct of molecular weight 1500 from diphenylsilane and diallyl malonate, a resinous adduct of molecular weight 1450 from diphenylsilane and diallyl succinate, a resinous polyadduct of molecular weight 1000 from diphenylsilane and diallyl adipate, a resinous polyadduct of molecular weight 1100 from diphenylsilane and diallyl sebacate, a resinous polyadduct of molecular weight 2800 from diphenylsilane and diallyl phthalate, a resinous polyadduct of molecular weight 1500 from diphenylsilane and divinyl adipate, a transparent gel from dimethylpolysiloxane containing 1 mol. per cent methylhydrosiloxane units and 1,5- hexadiene, and a gel-like adduct from 1,2-polybutadiene and trichlorosilane.