4.6 Article

1,2,3-Trimethoxypropane and Glycerol Ethers as Bio-Sourced Solvents from Glycerol. Synthesis by Solvent-Free Phase-Transfer Catalysis and Utilization as an Alternative Solvent in Chemical Transformations

期刊

CHEMCATCHEM
卷 5, 期 10, 页码 2893-2904

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201300458

关键词

alkylation; CC coupling; glycerol; green chemistry; phase-transfer catalysis; transesterification

资金

  1. Sofiproteol

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1,2,3-Trimethoxypropane (2), 1-alkoxy-2,3-dimethoxy-propanes, and 1-aryloxy-2,3-dimethoxypropanes were prepared in good yields and selectivity by solid-liquid phase-transfer catalysis in the presence of an inorganic base and an ammonium salt as the phase-transfer catalyst with no additional solvent. No heating was required, and the synthesis was easily performed under atmospheric pressure on a 150g scale. For the preparation of 2, the conversion of glycerol was complete and the selectivity for the expected glycerol trimethylether was above 95%. This product was utilized as a solvent in organic reactions such as transesterifications between glycerol and vegetable oil, organometallic reactions (Grignard- and Barbier-type reactions), carbon-carbon coupling reactions (Suzuki, Sonogashira, Heck), and in etherification reactions by dehydrogenative alkylation. The solvent showed interesting properties for the solubilization of polymers.

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