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

doi:10.1246/bcsj.20150080

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 journal › Article › peer-review

31 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 S_N2 reaction on primary C1 of sorbitol attacked by OH of secondary C4.

Original language	English
Pages (from-to)	996-1002
Number of pages	7
Journal	Bulletin of the Chemical Society of Japan
Volume	88
Issue number	7
DOIs	https://doi.org/10.1246/bcsj.20150080
Publication status	Published - 2015
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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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.",

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T1 - Sulfuric acid-catalyzed dehydration of sorbitol

T2 - Mechanistic study on preferential formation of 1,4-sorbitan

AU - Yabushita, Mizuho

AU - Kobayashi, Hirokazu

AU - Shrotri, Abhijit

AU - Hara, Kenji

AU - Ito, Shogo

AU - Fukuoka, Atsushi

PY - 2015

Y1 - 2015

N2 - 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.

AB - 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.

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

Abstract

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