Mechanistic Insight into Methacrolein Formation from Formaldehyde and Propionaldehyde

Aldol condensation is a very important reaction in forming new C = C bond, and is an attractive way to extend the carbon chain of a molecule. In this research, diethylammonium acetate was used as an acid–base bifunctional catalyst to facilitate the formation of methacrolein via cross aldol condensat...

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Bibliographic Details
Published in:Catalysis letters 2022-03, Vol.152 (3), p.799-805
Main Authors: Yan, Ruiyi, Lv, Zhaopo, Tang, Hongguo, Bai, Yinge, Li, Mengyue, Li, Yuchao
Format: Article
Language:English
Subjects:
Acetates
Acids
Aldehydes
Catalysis
Chemical industry
Chemistry
Chemistry and Materials Science
Formaldehyde
Industrial Chemistry/Chemical Engineering
Investigations
Molecular chains
Olefins
Organometallic Chemistry
Physical Chemistry
Reaction intermediates
Reaction mechanisms
Selectivity
Substrates
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Summary:Aldol condensation is a very important reaction in forming new C = C bond, and is an attractive way to extend the carbon chain of a molecule. In this research, diethylammonium acetate was used as an acid–base bifunctional catalyst to facilitate the formation of methacrolein via cross aldol condensation between formaldehyde and propionaldehyde. A conversion of 99.9% of propionaldehyde with a 97.4% selectivity to methacrolein (MAL) was achieved. Isotopic tracing experiments were used to propose a possible reaction mechanism. To verify the reactive pathway, we used isotopically labelled substrates. In addition, we attempted to trap the relevant reaction intermediate by decreasing the reaction temperature. Graphical Abstract
ISSN:1011-372X
1572-879X
DOI:10.1007/s10562-021-03679-5