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

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)996-1002
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume88
Issue number7
DOIs
Publication statusPublished - 2015
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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