Alkoxylation of coal with α-olefin epoxide

• Published in: Fuel (Guildford) Vol. 67; no. 1; pp. 19 - 23
• Main Authors: Iso, Mamoru, Lee, Yoshitaka, Sato, Kenji, Shirahase, Toru, Omi, Shinzo
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 1988; Elsevier
• Subjects: alkoxylation; Applied sciences; Exact sciences and technology; liquefaction of coal; olefin epoxide; Other techniques and industries; alkoxylation; olefin epoxide; liquefaction of coal
• ISSN: 0016-2361; 1873-7153
• DOI: 10.1016/0016-2361(88)90006-3

Alkoxylation (alkoxyl substitution or addition) or coal was achieved with α-olefin epoxide to give a product with a high yield of tetrahydrofuran- and quinoline-soluble products. Akabira coal was mainly used, and the effect of feed ratio (α-olefin epoxide/coal), reaction time and carbon chain length of α-olefin epoxide to the yield of solvent extraction was studied. The reaction proceeded mildly at 573 K without catalyst and was complete within 10 min. Analyses by 1H nuclear magnetic resonance (n.m.r.) and gel permeation chromatography (g.p.c.) revealed that the coal was alkoxylated by α-olefin epoxide. To investigate the mechanism of this reaction in detail, model compounds containing similar structures as occur in coal were reacted with α-olefin epoxide under the same conditions. It was confirmed that hydroxyl- and nitrogen-containing compounds such as phenol, α-naphthol, pyridine and quinoline reacted easily with α-olefin epoxide and long-chain alkoxyl groups were introduced.