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Flipping A Switch On Biobased Chemicals

Chemists develop a simple peroxide driven oxidation of levulinic acid that can be switched to make succinic acid or 3-hydroxypropanoic acid

by Stephen K. Ritter
March 16, 2015 | A version of this story appeared in Volume 93, Issue 11

The chemical reaction of levulinic acid to succinic acid using hydrogen peroxide.

Levulinic acid prepared from sugar or other biomass sources has been tagged as a platform chemical of the future for when fossil-fuel supplies dwindle. Chemists have been exploring an array of reactions to convert levulinic acid and related biobased platform chemicals to downstream feedstocks. Many of these processes rely on fermentation using engineered microbes, but researchers are also interested in using chemical methods that could be faster and more cost-effective on a large scale. In one of the latest examples, Mark Mascal, Linglin Wu, and Saikat Dutta of the University of California, Davis, have demonstrated an efficient peroxide-based oxidation of levulinic acid with switchable selectivity. Under acidic conditions, the H2O2 oxidation favors formation of succinic acid (Green Chem. 2015, DOI: 10.1039/c5gc00098j). The same process under basic conditions gives 3-hydroxypropanoic acid (ChemSusChem 2015, DOI: 10.1002/cssc.201500025). Biobased succinic acid is a compound of growing importance for making polymers, 1,4-butanediol, maleic anhydride, and furans, whereas 3-hydroxypropanoic acid serves as a precursor to polymers, acrylic acid, and acrylates. Patents are pending on the new chemistry, and the UC Davis team is exploring commercialization options.


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