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Acid-Catalyzed Dehydration of Sorbitol to 1,4-Sorbitan

  • Mizuho YabushitaEmail author
Chapter
Part of the Springer Theses book series (Springer Theses)

Abstract

1,4-Sorbitan is a precursor to environmentally benign surfactants, which can be produced from biomass via sorbitol. Acid catalysts convert sorbitol to 1,4-sorbitan; however, successive dehydration of 1,4-sorbitan to isosorbide readily occurs, hampering the selective synthesis of 1,4-sorbitan. In this chapter, the author has studied the dehydration of sorbitol using a variety of acids including both homo- and heterogeneous ones, and H2SO4 has afforded 1,4-sorbitan with a good yield and selectivity. The kinetic study has revealed that the good yield and selectivity of 1,4-sorbitan are ascribed to both thermodynamics and kinetics. The association of H2SO4 with sorbitol is 4.3 times more favorable than that with 1,4-sorbitan, and thus the further dehydration of 1,4-sorbitan is inhibited in the presence of sorbitol. Furthermore, a reaction mechanism is proposed, based on detailed product identification. The dehydration proceeds through an SN2 mechanism; that is, the reaction occurs at C1 of sorbitol attacked by OH of secondary C4.

Keywords

1,4-Sorbitan Acid catalysts Association Dehydration Sorbitol 

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Copyright information

© Springer Science+Business Media Singapore 2016

Authors and Affiliations

  1. 1.Graduate School of Chemical Sciences and EngineeringHokkaido UniversitySapporoJapan

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