Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 10, Issue 31, Pages 10192-10202Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.2c01727
Keywords
biocatalysis; solvent-free; transesterification; glycolipid; lipase; biosurfactants
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Funding
- European Regional Development Fund
- Ministry of Science, Research and the Arts of the State of Baden-Wurttemberg within the research center ZAFH InSeL [32-7545.24-20/6/3]
- Helmholtz-Society
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In this study, the combination of biocatalysis and mechanochemistry was used to synthesize glycolipid surfactants, resulting in higher yields using unconventional dissolved reaction systems and bead mill apparatus.
Mechanochemical and biocatalytic approaches in modern research are two major assets to develop greener processes. In the present study, these modular tools of sustainability are pointed toward the production of versatile and daily employed compounds such as surfactants. Toward this aim, glycolipids, a class of nonionic surfactants composed of ubiquitous and primary metabolites such as sugar and fatty acid moieties, represent a promising alternative to petroleum-derived surface-active agents. Therefore, the combination of biocatalysis with mechanochemistry aiming at glycolipid synthesis seemed a logical step that was taken in this study for the first time. The monoacylated model compound glucose-6-O-decanoate was synthesized with the help of a bead mill apparatus using two different unconventional dissolved reaction systems, namely, menthol-based hydrophobic deep eutectic solvents and 2-methyl-2-butanol, thus reaching up to 12% yield in the latter based on the conversion of vinyl decanoate, after only 90 min of reaction. In addition, a neat reaction system using an excess of vinylated fatty ester as an adjuvant allowed a 27 mM/h space-time yield. The overall significant increase in productivities, up to 6 times, compared to standard heating and shaking methods, shows the tremendous potential of mechanoenzymatic synthesis.
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