Comparison of activity and selectivity of weakly basic anion-exchange catalysts for the aldolization of butyraldehyde with formaldehyde

Citation
V. Serra-holm et al., Comparison of activity and selectivity of weakly basic anion-exchange catalysts for the aldolization of butyraldehyde with formaldehyde, ORG PROC R, 5(4), 2001, pp. 368-375
Citations number
5
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC PROCESS RESEARCH & DEVELOPMENT
ISSN journal
10836160 → ACNP
Volume
5
Issue
4
Year of publication
2001
Pages
368 - 375
Database
ISI
SICI code
1083-6160(200107/08)5:4<368:COAASO>2.0.ZU;2-D
Abstract
Aldols are important intermediates in the production of polyols, which are raw material for lubricants, surface coatings, and synthetic resins. The ac tivities and selectivities of gel-type and macroporous anion-exchange resin catalysts in the aldolization of butyraldehyde with formaldehyde in an aqu eous environment were investigated at 60 degreesC. The experiments were car ried out batchwise in a stirred glass reactor, and the reaction products we re analyzed with high performance liquid chromatography. Two main products were observed, 2-ethyl-3-hydroxy-2-hydroxy-methylpropanal (trimethylolpropa ne aldol) and 2-ethylpropenal (ethylacrolein). The product ratio was strong ly dependent on the catalyst. The selectivity with respect to trimethylolpr opane aldol varied within the range 2.7-7.3 for the catalysts investigated. Systematic kinetic experiments were carried out at 50-70 degreesC with the gel-type resin catalyst displaying the highest aldol selectivity. A kineti c model based on molecular mechanisms was able to describe the product dist ribution.