Role of acid sites and selectivity correlation in solvent free liquid phase dehydration of sorbitol to isosorbide

Aasif A. Dabbawala; Dinesh K. Mishra; George W. Huber; Jin Soo Hwang

doi:10.1016/j.apcata.2014.12.014

Role of acid sites and selectivity correlation in solvent free liquid phase dehydration of sorbitol to isosorbide

Aasif A. Dabbawala, Dinesh K. Mishra, George W. Huber, Jin Soo Hwang

Research output: Contribution to journal › Article › peer-review

79 Scopus citations

Abstract

A number of Brönsted acids (methanesulfonic acid, p-toluene sulfonic acid, triflic acid, sulfamic acid, citric acid, NaHSO₄, and boric acid) and Lewis acids (metal sulfate/triflates) were employed in solvent free dehydration of sorbitol and their influence on anhydroalcohols selectivity has been investigated. The outcome indicated that all the acid catalysts produced first mono-dehydrated product sorbitan followed by second dehydration of 1,4-sorbitan to isosorbide. However, the formation and yield isosorbide were found to depend on the nature of acid sites and their acidic strength. The Brönsted acids are more efficient to convert sorbitol to isosorbide than Lewis acids. The Brönsted acids having lower pK_a value (i.e. strong acid) exhibited high catalytic activity as well as yield of isosorbide. In the case of Lewis acids, the catalytic activity and selectivity were radically depended on which metal used and their stability during the reaction. The water formed during reaction induced Brönsted acidity on Lewis acid metal site. The Lewis-assisted Brönsted acid site enabled high yield of isosorbide up to 70% at moderate temperature (160°C).

Original language	British English
Pages (from-to)	252-261
Number of pages	10
Journal	Applied Catalysis A: General
Volume	492
Issue number	1
DOIs	https://doi.org/10.1016/j.apcata.2014.12.014
State	Published - 25 Feb 2015

Keywords

Brönsted acid
Dehydration
Lewis acid
Selectivity
Sorbitol

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10.1016/j.apcata.2014.12.014

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title = "Role of acid sites and selectivity correlation in solvent free liquid phase dehydration of sorbitol to isosorbide",

abstract = "A number of Br{\"o}nsted acids (methanesulfonic acid, p-toluene sulfonic acid, triflic acid, sulfamic acid, citric acid, NaHSO4, and boric acid) and Lewis acids (metal sulfate/triflates) were employed in solvent free dehydration of sorbitol and their influence on anhydroalcohols selectivity has been investigated. The outcome indicated that all the acid catalysts produced first mono-dehydrated product sorbitan followed by second dehydration of 1,4-sorbitan to isosorbide. However, the formation and yield isosorbide were found to depend on the nature of acid sites and their acidic strength. The Br{\"o}nsted acids are more efficient to convert sorbitol to isosorbide than Lewis acids. The Br{\"o}nsted acids having lower pKa value (i.e. strong acid) exhibited high catalytic activity as well as yield of isosorbide. In the case of Lewis acids, the catalytic activity and selectivity were radically depended on which metal used and their stability during the reaction. The water formed during reaction induced Br{\"o}nsted acidity on Lewis acid metal site. The Lewis-assisted Br{\"o}nsted acid site enabled high yield of isosorbide up to 70% at moderate temperature (160°C).",

keywords = "Br{\"o}nsted acid, Dehydration, Lewis acid, Selectivity, Sorbitol",

author = "Dabbawala, {Aasif A.} and Mishra, {Dinesh K.} and Huber, {George W.} and Hwang, {Jin Soo}",

note = "Funding Information: We would like to acknowledge the financial support from the R&D Convergence Program of MSIP (Ministry of Science, ICT and Future Planning) and Institutional Research Program of KRICT funded by the Korea Research Council Industrial Science and Technology, Republic of Korea (Grant no. SI-1401 and B551179-10-03-00 ). Publisher Copyright: {\textcopyright} 2014 Elsevier B.V. All rights reserved.",

year = "2015",

month = feb,

day = "25",

doi = "10.1016/j.apcata.2014.12.014",

language = "British English",

volume = "492",

pages = "252--261",

journal = "Applied Catalysis A: General",

issn = "0926-860X",

publisher = "Elsevier B.V.",

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TY - JOUR

T1 - Role of acid sites and selectivity correlation in solvent free liquid phase dehydration of sorbitol to isosorbide

AU - Dabbawala, Aasif A.

AU - Mishra, Dinesh K.

AU - Huber, George W.

AU - Hwang, Jin Soo

N1 - Funding Information: We would like to acknowledge the financial support from the R&D Convergence Program of MSIP (Ministry of Science, ICT and Future Planning) and Institutional Research Program of KRICT funded by the Korea Research Council Industrial Science and Technology, Republic of Korea (Grant no. SI-1401 and B551179-10-03-00 ). Publisher Copyright: © 2014 Elsevier B.V. All rights reserved.

PY - 2015/2/25

Y1 - 2015/2/25

N2 - A number of Brönsted acids (methanesulfonic acid, p-toluene sulfonic acid, triflic acid, sulfamic acid, citric acid, NaHSO4, and boric acid) and Lewis acids (metal sulfate/triflates) were employed in solvent free dehydration of sorbitol and their influence on anhydroalcohols selectivity has been investigated. The outcome indicated that all the acid catalysts produced first mono-dehydrated product sorbitan followed by second dehydration of 1,4-sorbitan to isosorbide. However, the formation and yield isosorbide were found to depend on the nature of acid sites and their acidic strength. The Brönsted acids are more efficient to convert sorbitol to isosorbide than Lewis acids. The Brönsted acids having lower pKa value (i.e. strong acid) exhibited high catalytic activity as well as yield of isosorbide. In the case of Lewis acids, the catalytic activity and selectivity were radically depended on which metal used and their stability during the reaction. The water formed during reaction induced Brönsted acidity on Lewis acid metal site. The Lewis-assisted Brönsted acid site enabled high yield of isosorbide up to 70% at moderate temperature (160°C).

AB - A number of Brönsted acids (methanesulfonic acid, p-toluene sulfonic acid, triflic acid, sulfamic acid, citric acid, NaHSO4, and boric acid) and Lewis acids (metal sulfate/triflates) were employed in solvent free dehydration of sorbitol and their influence on anhydroalcohols selectivity has been investigated. The outcome indicated that all the acid catalysts produced first mono-dehydrated product sorbitan followed by second dehydration of 1,4-sorbitan to isosorbide. However, the formation and yield isosorbide were found to depend on the nature of acid sites and their acidic strength. The Brönsted acids are more efficient to convert sorbitol to isosorbide than Lewis acids. The Brönsted acids having lower pKa value (i.e. strong acid) exhibited high catalytic activity as well as yield of isosorbide. In the case of Lewis acids, the catalytic activity and selectivity were radically depended on which metal used and their stability during the reaction. The water formed during reaction induced Brönsted acidity on Lewis acid metal site. The Lewis-assisted Brönsted acid site enabled high yield of isosorbide up to 70% at moderate temperature (160°C).

KW - Brönsted acid

KW - Dehydration

KW - Lewis acid

KW - Selectivity

KW - Sorbitol

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U2 - 10.1016/j.apcata.2014.12.014

DO - 10.1016/j.apcata.2014.12.014

M3 - Article

AN - SCOPUS:84949115931

SN - 0926-860X

VL - 492

SP - 252

EP - 261

JO - Applied Catalysis A: General

JF - Applied Catalysis A: General

IS - 1

ER -

Role of acid sites and selectivity correlation in solvent free liquid phase dehydration of sorbitol to isosorbide

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