Hydrogenation of aldehydes and ketones catalyzed by zeolite-supported polyvinyl alcohol–amino acid–platinum complex

✍ Scribed by Li Liu; Ding Xia; Quan Zhang; Mei-Yu Huang; Ying-Yan Jiang

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 94 KB
• Volume: 10
• Category: Article
• ISSN: 1042-7147
• DOI: 10.1002/(sici)1099-1581(199901/02)10:1/2<103::aid-pat777>3.0.co;2-t

✦ Synopsis

Zeolite-supported polyvinyl alcohol±amino acid (alanine, proline, glutamine, leucine or lysine)±platinum complexes (Zeo-PVA-AA-Pt) have been prepared by a very simple method and have been found to catalyze the hydrogenation of some aldehydes and ketones such as hexanal, benzaldehyde, cyclohexanone, 2-pentanone, methyl acetoacetate, ethyl acetoacetate, 2,4-pentandione to 1-hexanol, cyclohexylmethanol, cyclohexanol, 2-pentanol, methyl 3-hydroxybutyrate, ethyl 3-hydroxybutyrate and 2,4-pentandiol, respectively, at 55°C and under an atmospheric hydrogen pressure. In several cases, the yield or selectivity amounted to 100%. Such catalysts were very stable in the hydrogenation, and could be reused several times without any remarkable change in the catalytic activity. The catalytic activity was greatly affected by molar ratios of monomer unit of polyvinyl alcohol to amino acid, amino acid to Pt in the complex, and the nature of the amino acids and solvent used in hydrogenation.

In the hydrogenation of methyl acetoacetate to methyl 3-hydroxybutyrate, a small amount of optical active product was obtained. This result suggested that more effective catalysts for asymmetric hydrogenation may be found from such simple polymer±amino acid±metal complexes by selecting the proper amino acid and polymer.