GB441016A - Process for the manufacture of condensation products - Google Patents

Abstract

Aliphatic dicarboxylic acids or acid anhydrides substituted by residues of saturated aliphatic or alicyclic hydrocarbons or aryl or arylene derivatives thereof are prepared by interacting saturated aliphatic or alicyclic hydrocarbons, ethers or ketones or aryl or arylene derivatives thereof which contain at least one hydrogen atom attached to at least one aliphatic carbon atom and all the aliphatic atoms of which are connected by single bonds with a -b -unsaturated aliphatic dicarboxylic acid anhydrides or compounds which are converted into these anhydrides under the reaction conditions. The reaction may be accelerated by a copper catalyst and by the use of heat and pressure. Suitable starting materials include paraffinic hydrocarbons such as heptane or paraffin oil, completely or partially saturated cyclic hydrocarbons such as cyclohexane, decahydronaphthalene and tetrahydronaphthalene, aromatic hydrocarbons with saturated side chains such as toluene, ethylbenzene and propylbenzene, ethers such as dibenzyl ether and ketones such as 2-methylanthraquinone, and maleic anhydride, citraconic acid anhydride, maleic acid and fumaric acid. In examples: maleic acid is reacted in the presence of copper bronze or in a vessel with a copper lining with (1) ethylbenzene, (4) dibenzylether, (5) heptane, paraffin oil, (6) cyclohexane, and (7) decahydronaphthalene, or fumaric acid is reacted in the presence of copper bronze powder with ethylbenzene. The Specification as open to inspection under Sect. 91 also refers generally to the reaction of organic compounds which contain at least one aliphatic carbon atom combined with at least one hydrogen atom and all the aliphatic atoms of which are connected by single bonds with a -b -unsaturated aliphatic dicarboxylic acid anhydrides or compounds which are converted into these anhydrides under the reaction conditions. An inert solvent or catalysts such as iodine or sulphur may be used. Suitable starting materials include hydrogenated colophony, diethylbenzene, methylnaphthalene, acetophenone and cyclohexanone. In examples there is described the condensation of (1) maleic anhydride and tetrahydronaphthalene or acetophenone in the presence of iodine; (5) maleic anhydride and cyclohexanone; (7) maleic anhydride and heptane in the presence of iodine; (8) decahydronaphthalene and citraconic anhydride in the presence of iodine; (9) hydrogenated colophony and maleic anhydride in the presence of colophony and (10) iso-propylbenzene and maleic anhydride in the presence of quartz. This subject-matter does not appear in the Specification as accepted.