Sulfuric acid-catalyzed dehydration of sorbitol: Mechanistic study on preferential formation of 1,4-sorbitan

Mizuho Yabushita, Hirokazu Kobayashi, Abhijit Shrotri, Kenji Hara, Shogo Ito, Atsushi Fukuoka

研究成果: Article査読

18 被引用数 (Scopus)

抄録

1,4-Sorbitan is a precursor to environmentally benign surfactants, which can be produced from biomass via sorbitol. Currently, sulfuric acid-catalyzed dehydration of sorbitol is the most widely used route for industrial synthesis of 1,4-sorbitan. In this work, we have studied the mechanism of the sorbitol dehydration by sulfuric acid. Our results show that both thermodynamic and kinetic parameters play significant roles to determine the yield of 1,4-sorbitan. Sorbitol preferentially forms an adduct with sulfuric acid, thereby inhibiting the subsequent dehydration of 1,4-sorbitan to isosorbide. Furthermore, a reaction mechanism is proposed for the dehydration reaction, which involves an SN2 reaction on primary C1 of sorbitol attacked by OH of secondary C4.

本文言語English
ページ(範囲)996-1002
ページ数7
ジャーナルBulletin of the Chemical Society of Japan
88
7
DOI
出版ステータスPublished - 2015
外部発表はい

ASJC Scopus subject areas

  • Chemistry(all)

フィンガープリント 「Sulfuric acid-catalyzed dehydration of sorbitol: Mechanistic study on preferential formation of 1,4-sorbitan」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル