GB1153814A - Process for producing Alkyl Esters of gammaCyano-Acids - Google Patents

Abstract

1,153,814. Alkyl esters of #-cyano acids. RHONE-POULENC S.A. 13 July, 1967 [13 July, 1966], No. 32385/67. Heading C2C. Alkyl #-cyano-valerates and 5-cyano-penten- 4-oates may be obtained by heating a mixture of acrylonitrile and an alkyl acrylate under a hydrogen atmosphere in the presence of a ruthenium compound as catalyst. The reaction may be effected at 50-150‹ C. under a hydrogen pressure of 1 to 50 bars, optionally in the presence of an inert liquid diluent, and the catalyst, which may be employed in an amount of 0À04-1À2% by weight of metallic ruthenium based on the weight of the reactants, may be used in the solid state, in finely divided form, in suspension or solution in the monomers, in water or in an inert organic solvent. The ruthenium catalyst employed may be an organic or inorganic derivative of ruthenium such as a halide, thiocyanate, a salt of an inorganic oxygen-containing acid or an organic acid, an alkali or alkaline earth metal ruthenate, a mixed salt of ruthenium and an alkali metal, a chelate of ruthenium or a complex of a ruthenium derivative with an electron donor which may be prepared by heating a ruthenium halide with an electron donor, optionally in the presence of a solvent which may itself participate in the preparation of the complex. In specific examples methyl #-cyanovalerate and cis and trans methyl 5-cyano-penten-4-oate are prepared; methyl propionate, propionitrile, 1,4- dicyanobutene-1, adiponitrile, methyl adipate and methyl α-dihydromuconate are also formed in varying amounts.