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Synthesis

Greener Methylations

Dimethyl carbonate is a top methylating reagent for a high-yield, supercritical CO2 synthesis of methyl ethers

by Stephen K. Ritter
February 15, 2010 | A version of this story appeared in Volume 88, Issue 7

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Credit: Courtesy of Richard Bourne
Nottingham graduate student Andrew J. Parrott adjusts thesupercritical reactor used for continuous methylations.
Credit: Courtesy of Richard Bourne
Nottingham graduate student Andrew J. Parrott adjusts thesupercritical reactor used for continuous methylations.

Dimethyl carbonate is a “superior” meth­yl­ating reagent in a high-yield synthesis of industrially important methyl ethers, according to a research team led by Derek J. Irvine and Martyn Poliakoff of the University of Nottingham, in England (Org. Process Res. Dev., DOI: 10.1021/op900307w). Ethers are traditionally made via the Williamson ether synthesis, which employs an alcohol and sodium hydroxide to form an alkoxide that subsequently couples with an alkyl halide. But that method requires toxic alkyl halides as reagents and generates undesirable inorganic salts as by-products. Building on their expertise in continuous-flow supercritical CO2 reactor technology, the Nottingham researchers showed that solid-acid catalysts, such as γ-alumina, mediate the selective reaction of nontoxic dimethyl carbonate with 1-octanol and other primary alcohols to form methyl ethers in supercritical CO2 solvent (170–270 °C, 100 bar). The research was sponsored by specialty chemical manufacturer Croda as part of its effort to identify greener technologies for making ingredients that go into cosmetics, toiletries, and other consumer products.

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