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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

 

E-mail: chemtec@163.com

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.

DOI: 10.2478/s11696-013-0450-5

 

Chemical Papers 68 (3) 422–426 (2014)

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