Improvement of the selectivity of isophorone hydrogenation by Lewis acids

• Main Authors: Yucui Hou, Shuhang Ren, Muge Niu, Weize Wu
• Format: Article
• Language: English
• Published: The Royal Society 2018-01-01
• Series: Royal Society Open Science
• Subjects: hydrogenation; selectivity; isophorone; lewis acid; mechanism
• Online Access: https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.171523

The selective hydrogenation of isophorone (3,5,5-trimethyl-2- cyclohexen-1-one) to produce 3,3,5-trimethylcyclohexanone (TMCH), an important organic solvent and pharmaceutical intermediate, is of significance in industry. However, the over-hydrogenation to produce the by-product 3,3,5-trimethylcyclohexanol causes issues. Up to now, it is still a challenge to hydrogenate isophorone to TMCH with high selectivity. In this work, we found that Lewis acids could inhibit the hydrogenation of C=O bond on isophorone, thus greatly improving the selectivity towards TMCH. In addition, added solvents like supercritical CO2 also had a positive impact on the selectivity. Both the conversion and selectivity could be increased to more than 99% when suitable Lewis acid and solvent were employed. Nevertheless, Lewis acid also exhibited some inhibition on the hydrogenation of the C=C bond of isophorone. Hence, a relatively weak Lewis acid, ZnCl2, is suitable for the selective hydrogenation.