Journal
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
Volume 88, Issue 7, Pages 996-1002Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/bcsj.20150080
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Funding
- Japan Society for the Promotion of Science (JSPS)
- Grants-in-Aid for Scientific Research [14J01171, 25106010] Funding Source: KAKEN
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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(N)2 reaction on primary C1 of sorbitol attacked by OH of secondary C4.
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