Advertisement

If you have an ACS member number, please enter it here so we can link this account to your membership. (optional)

ACS values your privacy. By submitting your information, you are gaining access to C&EN and subscribing to our weekly newsletter. We use the information you provide to make your reading experience better, and we will never sell your data to third party members.

ENJOY UNLIMITED ACCES TO C&EN

Synthesis

Spinning Sugar Into Hydrocarbons

Oxorhenium catalyst strips sugars and sugar alcohols of their oxygen atoms

by Bethany Halford
July 30, 2012 | A version of this story appeared in Volume 90, Issue 31

In some sweet synthetic work, chemists at the University of California, Berkeley, have found a mild method for converting sugars and sugar alcohols into aromatic compounds and polyenes, respectively (Angew. Chem. Int. Ed., DOI: 10.1002/anie.201203877). The deoxydehydration reaction, developed by F. Dean Toste and Mika Shiramizu, could be used to convert saccharides, the major component of cellulosic biomass, into commodity chemicals and fuels. Although the deoxydehydration reaction has been used to pluck oxygen atoms off of diols and epoxides, getting the reaction to strip down polyols had been problematic. Toste and Shiramizu discovered that a methyltrioxorhenium catalyst could do the job efficiently when an alcohol, such as 3-pentanol, was used as a reductant. For example, using this protocol, they transformed the six-carbon sugar alcohol d-sorbitol into hexatriene—a possible feedstock for polymers. And when the chemists used sugars in the reaction, followed by dehydration, they were able to generate aromatic compounds, such as furan, benzene, and phenol. Future plans include boosting the reaction’s efficiency, applying the transformation to polysaccharides, and immobilizing and recycling the catalyst.

Article:

This article has been sent to the following recipient:

0 /1 FREE ARTICLES LEFT THIS MONTH Remaining
Chemistry matters. Join us to get the news you need.