Conversion of cyclododecane to cyclododecanol is of considerable interest as one of the stages of the synthesis of w-dodecalactam and 1, lo-decanedicarboxylic acid on the basis of butadiene, which is being developed at present.
The authors have worked out a method for obtaining cyclododecanol by liquid-phase oxidation of cyclododecane in the presence of boric acid, the yield of cyclododecanol amounting to about 80 O/O of the hydrocarbon converted.
La conversion du cyclododécane en cyclododé- cano1 présente un grand intérêt comme un des stades de la synthèse en voie d'élaboration de I'm-dodécalactame et du diacide 1, lO-décanoïque à base de butadiène.
Les auteurs ont élaboré une méthode de préparation du cyclododécanol par oxydation en phase liquide du cyclr,. dodécane en présence de l'acide borique; le procédé assure un rendement en cyclododécanol d'environ 80 %, calculé en hydrocarbure transformé.
Higher cyclic alcohols can be used as intermediates in the production of synthetic fibres (polyamides of the Rilsan type), plastics, dicarboxylic acids, plasticizers, synthetic lubricants, in perfumery, etc. Therefore, the development of methods for their synthesis is not only of theoretical, but also practical interest.
At present there is no commercial method for producing higher cyclic alcohols.
This paper presents the basic data obtained in the development of synthesis of higher individual t*yclic alcohols, based on the liquid-phase oxidation with molecular oxygen of naphthenic hydrocarbons having no side-chain substituents.
A number of consequences follow from the concept that the value of the C-H bond energy to a considerable extent predetermines the position of oxygen attached to a hydrocarbon molecule. Oxidation of hydrocarbons having in the molecule a special group, the most reactive one from a standpoint of the minimum C-H bond energy for a given molecule, should result mainly in compounds (monofunctional) with a fixed position of the functional group, provided * Authors' Biographies vide last page the oxidation of this group does not involve additional difficulties (spacial and some others).
Thus, for example, when methylcyclohexane is oxidized, the main product obtained is l-methylcyclohexyl hydroxidel) (the C-H bond energy is 95.3 kcal/mole for the -CH, group, 90 kcal/mole for the > CH, group, 80 kcal/mole for the + CH group).
The oxidation of isopropyl benzene gives predominantly isopropyl benzene hydroxidez), the C-H bond energy in the benzene ring being 99 kcal/mole.
If a hydrocarbon molecule having C-H-bonds of different energy contains several equivalent groups with the minimum C-H bond energy for this molecule, the oxidation of such hydrocarbons should give oxygen-containing compounds w