Biomass-derived carbohydrates convert to alkenes using a one-pot technique that could lead to biomass refinery processes, say scientists in the US.
Alkenes are extensively used in industry, but at present they are derived almost exclusively from petroleum resources. The petrochemical industry makes a wide variety of products from fossil resources such as fuels, plastics and commodity chemicals. Biomass could theoretically be used to make the same or similar products, however the high oxygen content of biomass-derived raw materials prevents their direct use as fuels or chemicals.
Robert Bergman and colleagues at the University of California, Berkeley, have developed a selective one-pot, formic acid-mediated deoxygenation technique for converting polyhdroxy compounds, such as biomass-derived carbohydrates, to alkenes in high yields.
Significantly, Bergmans’ studies revealed an unexpected mechanism for this transformation, involving a cyclic intermediate bearing a positively charged carbon atom. ‘This mild one-step and inexpensive procedure is a promising tool for the development of biomass refinery processes,’ says Bergman.
Industries such as biofuel manufacturers, sugar refineries and plastics and resin manufacturers, are interested in the transformation of naturally occurring highly oxygenated compounds into less oxygenated materials. Bergmans’ transformation would provide access to intermediates with high industrial potential that could be performed on a large scale.
In the future, biomass-derived alkene feedstocks could ultimately replace petrochemical-based monomers in polymer and oligomer production, explains Bergman. However, ‘a combined effort of companies and academic laboratories is needed to make biomass competitive with fossil raw materials,’ he says.
Original article: Arceo et. al.; Chem. Commun. 2009