发明名称 Preparation of oxygenated products from cyclic mono-olefins by ozonization and oxidation
摘要 Vinyl monomers are polymerized with a catalyst comprising the products obtained by ozonizing a bicyclo (2.2.1)-2 heptene dissolved in a normal C1 to C10 aliphatic alcohol (see Group IV(b)). The ozonization products may be represented by the formula: <FORM:0844825/IV(a)/1> wherein R is hydrogen or a C1 to C4 alkyl group, P and R11 taken together are a cyclizing peroxide group and R111 is OH or OR1 and otherwise P is a hydroperoxide group and R11 and R111 taken together are oxygen and R1 is a normal C1 to C10 alkyl group. Vinyl monomers specified include styrene, methyl acrylate and methacrylate acrylonitrile, vinyl acetate, vinyl halides such as vinyl chloride, vinyl ketones, vinyl sulphonamides, butadiene, chloroprene and mixtures thereof. The polymerization may be carried out as a mass, suspension, solution or emulsion process, The polymerization of methyl methacrylate and styrene in the presence of a mixture obtained by ozonizing norbonnylene in methanol is described.ALSO:A process for preparing a dicarboxylic acid from a bicyclo (2,2.1)-2-heptene comprises reacting the bicyclo (2,2.1)-2-heptene with ozone in the presence of a solvent for the heptene at a temperature of from -100 DEG C. to +30 DEG C. and oxidising the reaction product thus obtained with hydrogen peroxide or molecular oxygen containing a catalytic amount of ozone in the presence of water and/or aliphatic monocarboxylic acids to obtain a dicarboxylic acid. Olefinic starting materials specified include norbornylene, 5-methyl-5-ethyl-, 5-propyl-, 5,5,6-trimethyl and 5,6-dimethyl bicyclo (2,2.1)-2-heptenes. Solvents specified for use in the ozonization step include lower aliphatic acids e.g. formic and acetic acids, esters of C1 to C14 aliphatic alcohols with C1 to C4 monocarboxylic acids e.g. methyl and ethyl formates and acetates and halogenated hydrocarbons such as carbon tetrachloride and chloroform which are inert under the reaction conditions. Alternatively C1 to C10 aliphatic alcohols may be employed as solvents in the first step when alkoxy peroxides of the formula: <FORM:0844825/IV(b)/1> wherein R represents hydrogen or a C1 to C4 alkyl group and P and R11 taken together are a cyclizing peroxide group and R111 is OH or OR1 or otherwise P is a hydroperoxide group and R11 and R111 taken together are oxygen and wherein R1 is a normal C1 to C10 alkyl group, are obtained. The ozonization of norbornylene in the presence of inert solvents and methanol and the subsequent oxidation of the ozonization products to cis-1,3-cyclopentane dicarboxylic acids by means of hydrogen peroxide and aqueous formic acid or a mixture of oxygen and ozone are described. The ozonization products catalize the polymerization of vinyl monomers (see Group IV(a)).
申请公布号 GB844825(A) 申请公布日期 1960.08.17
申请号 GB19580027174 申请日期 1958.08.25
申请人 ESSO RESEARCH AND ENGINEERING COMPANY 发明人 BAILEY PHILIP SIGMON;JR. ROBERT HOOD PERRY,;COHEN CHARLES ANSCHEL;BEACH LELAND KENNETH
分类号 C07C51/285;C07C51/34;C07C409/20;C07D321/10;C07D323/02 主分类号 C07C51/285
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