ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
Trimerization of aldehydes with one α-hydrogen catalyzed by sodium hydroxide
Yu-Gang Li, Chen-Xi Luo, Chao Qian, and Xin-Zhi Chen
Key Laboratory of Biomass Chemical Engineering of Ministry of Education, Zhejiang University, 310027, Hangzhou, China
Abstract: Trimerization of 2-methylpropanal (isobutyraldehyde) is a simple and effective method to synthesize 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate and 2,2,4-trimethyl-1,3-pentanediol-3-monoisobutyrate which are often used as film forming auxiliaries in paints. The use of solid sodium hydroxide as a catalyst provides an excellent yield of above 85 % after the optimization of the reaction time and the catalyst dosage. Furthermore, trimerization of four other aldehydes with one α-hydrogen catalyzed by solid sodium hydroxide can also take place and the yield of 1,3-diol monoesters reaches 50–70 %. Trimerization of aldehydes with one α-hydrogen can be explained by a three-step reaction mechanism: (i) aldol condensation of aldehyde; (ii) crossed Cannizzaro reaction; and (iii) esterification of carboxylic acid and alcohol.
Keywords: trimerization – isobutyraldehyde – aldehydes – sodium hydroxide
Full paper is available at www.springerlink.com.
Chemical Papers 68 (3) 422–426 (2014)
Saturday, August 08, 2020