Selective Synthesis of 1-O-Alkyl(poly)glycerol Ethers by Catalytic Reductive Alkylation of Carboxylic Acids with a Recyclable Catalytic System

(Poly)glycerol monoethers were synthesized in good yield and selectivity by the catalytic reductive alkylation of glycerol, diglycerol, and triglycerol with readily available, cheap and/or bio‐sourced carboxylic acids. The reaction was catalyzed by 1 mol % of Pd/C under 50 bar H2 using an acid ion‐e...

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Bibliographic Details
Published in:ChemSusChem 2012-12, Vol.5 (12), p.2397-2409
Main Authors: Sutter, Marc, Dayoub, Wissam, Métay, Estelle, Raoul, Yann, Lemaire, Marc
Format: Article
Language:English
Subjects:
Acids
Alkylation
carboxylic acids
Carboxylic Acids - chemistry
Catalysis
Chemical Sciences
Ethers
Glycerol - chemical synthesis
Glycerol - chemistry
Green Chemistry Technology
heterogeneous catalysis
Molecular Structure
Organic chemistry
Oxidation-Reduction
palladium
Polymers - chemical synthesis
Polymers - chemistry
Recycling
reduction
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Summary:(Poly)glycerol monoethers were synthesized in good yield and selectivity by the catalytic reductive alkylation of glycerol, diglycerol, and triglycerol with readily available, cheap and/or bio‐sourced carboxylic acids. The reaction was catalyzed by 1 mol % of Pd/C under 50 bar H2 using an acid ion‐exchange resin as a recyclable cocatalyst. The catalytic system was recycled several times, and a mechanism is proposed for this transformation. Reductive alkylation, a new sensation: Reductive alkylation of (poly)glycerol is realized for the first time with bio‐sourced and/or cheap carboxylic acids under mild conditions by using a recyclable catalytic system. The corresponding 1‐O‐alkyl(poly)glycerol monoethers are obtained in good yield and selectivity, and the catalysts can be recycled three times with no loss of activity, opening a new access to glycerol ethers on a large scale.
ISSN:1864-5631
1864-564X
DOI:10.1002/cssc.201200447