GB1043507A - Cyclo-aliphatic diols and process for their preparation - Google Patents

Abstract

Dimer glycols containing 36, 40 or 44 carbon atoms in the molecule, esterified with, e.g., saturated dicarboxylic acids such as adipic or sebacic are stated to be suitable as lubricants.ALSO:Novel cycloaliphatic diols of the formula <FORM:1043507/C2/1> wherein R1 to R4 have a total of 30, 34 or 38 C atoms and are each a straight chain having at least 5 C atoms with two of these alkyl groups reacting a "dimer acid" having 36, 40 or 44 C atoms or an ester thereof, with hydrogen, at at least 100 ats. in the presence of a high pressure hydrogenation catalyst, especially copper chromite. Dimer acids are condensation products of poly-unsaturated fatty acids heated in the presence of alkaline or mildly acid catalysts, apparently by a Diels-Alder reaction, i.e. starting from C18, 20 or 22 carboxylic acids. Non-dimerized starting acids or esters thereof may be removed prior to hydrogenation by forming the urea inclusion complex, or the monohydric alcohol in a product may also be similarly removed from the hydrogenated product. Other suitable catalysts are stated to be copper/zinc oxides, copper and aluminium Raney nickel, palladium and platinum. The examples describe the use as starting material methyl esters and a polyester using the product as the glycol component. Named products include 1,2 - bis - (81 - hydroxy) octyl - 3 - octyl-4 - hexyl cyclohexane; 1,3 - bis - (81 - hydroxy) octyl - 2 - octyl - 4 - hexyl - cyclohexane; 1-(81-hydroxy) octyl - 2(101 - hydroxy) decyl - 3,4-dihexyl cyclohexane; 1 - (81 - hydroxy) octyl-2,4 - dihexyl - 3 - (101 - hydroxy) decyl - cyclo - hexane.ALSO:In Example 5 a "dimer acid" is reacted with a dimer diol, each having 36 to 44 carbon atoms in the molecule, the dimer diol having been prepared by hydrogenolysis of the dimer acid.