Metal-free transesterification catalyzed by tetramethylammonium methyl carbonate

• Published in: Green chemistry : an international journal and green chemistry resource : GC Vol. 20; no. 6; pp. 1193 - 1198
• Main Authors: Hatano, Manabu, Tabata, Yuji, Yoshida, Yurika, Toh, Kohei, Yamashita, Kenji, Ogura, Yoshihiro, Ishihara, Kazuaki
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 2018; Royal Society of Chemistry
• Subjects: Alcohol; Alcohols; Alkaloids; Alkoxides; Amino acids; Biodiesel fuels; Biofuels; Catalysis; Catalysts; Chelation; Chemistry; Chemistry, Multidisciplinary; Deactivation; Diols; Esters; Green & Sustainable Science & Technology; Green chemistry; Metals; Organic solvents; Physical Sciences; Salts; Science & Technology; Science & Technology - Other Topics; Substrates; Sugar; Transesterification; Triols; DIMETHYL CARBONATE; TERTIARY ALCOHOLS; PHOSPHONIUM SALTS; CHEMOSELECTIVE ACYLATION; ORGANIC-REACTIONS; ESTERS; ALKOXIDE CLUSTERS; N-HETEROCYCLIC CARBENES; SELECTIVE ACYLATION; CARBOXYLIC-ACIDS
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/c7gc03858e

Environmentally benign metal-free tetramethylammonium methyl carbonate is effective as a catalyst for the chemoselective, scalable, and reusable transesterification of various esters and alcohols in common organic solvents. In situ-generated highly active species, tetramethylammonium alkoxides, can greatly avoid selfdecomposition at <= 110 degrees C, and are reusable. In particular, chelating substrates, such as amino alcohols, diols, triols, sugar derivatives, alkaloids, a-amino acid esters, etc., which deactivate conventional metal salt catalysts, can be used. A 100 gram scale biodiesel production was also demonstrated.