Greening the esterification between isosorbide and acetic acid

Alexandra Inayat; Alexandre van Assche; James Hanley Clark; Thomas James Farmer

doi:10.1016/j.scp.2017.10.004

Greening the esterification between isosorbide and acetic acid

Alexandra Inayat, Alexandre van Assche, James Hanley Clark, Thomas James Farmer

Chemistry

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

Abstract

This contribution deals with the investigation of greener conditions for the preparation of 2,5-diacetyl-isosorbide from the bio-based substances isosorbide and acetic acid. The influence of solvent, catalyst and reactant ratio on the course of the isosorbide conversion and selectivity to 2,5-diacetyl-isosorbide as well as to the intermediate 2-acetyl-isosorbide is examined. It was found that the conventionally used solvent toluene can be substituted by the greener solvent n-propyl acetate. Additionally, the homogeneous acid catalyst p-toluene sulfonic acid can be replaced by the heterogeneous catalyst Amberlyst-15, resulting in an easier isolation of the desired 2,5-diacetyl-isosorbide, this being an important precursor for the vasodilatory drug isosorbide-5-nitrate.

Original language	English
Pages (from-to)	41-49
Number of pages	9
Journal	Sustainable Chemistry and Pharmacy
Volume	7
Early online date	6 Nov 2017
DOIs	https://doi.org/10.1016/j.scp.2017.10.004
Publication status	Published - Mar 2018

Bibliographical note

Keywords

isosorbide
2,5-diacetyl-isosorbide
2-acetyl-isosorbide
green synthesis
esterification

Access to Document

10.1016/j.scp.2017.10.004Licence: CC BY-NC-ND

Manuscript-EsterificationIsosorbide-SusChemPharm_revised
© 2017 Published by Elsevier B.V.
Accepted author manuscript, 2.01 MBLicence: CC BY-NC-ND

Sustainable Polymers
Clark, J. H. (Principal investigator), Farmer, T. J. (Co-investigator) & North, M. (Co-investigator)
EPSRC
1/03/14 → 28/05/19
Project: Research project (funded) › Research

Data supporting the publication "Greening the esterification of isosorbide with acetic acid"
Farmer, T. J. (Creator), Clark, J. H. (Contributor), Inayat, A. (Creator) & van Assche, A. (Contributor), University of York, Sept 2017
DOI: 10.15124/89e39495-492e-45ef-aafe-352d1cd3a8ff
Dataset

Cite this

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title = "Greening the esterification between isosorbide and acetic acid",

abstract = "This contribution deals with the investigation of greener conditions for the preparation of 2,5-diacetyl-isosorbide from the bio-based substances isosorbide and acetic acid. The influence of solvent, catalyst and reactant ratio on the course of the isosorbide conversion and selectivity to 2,5-diacetyl-isosorbide as well as to the intermediate 2-acetyl-isosorbide is examined. It was found that the conventionally used solvent toluene can be substituted by the greener solvent n-propyl acetate. Additionally, the homogeneous acid catalyst p-toluene sulfonic acid can be replaced by the heterogeneous catalyst Amberlyst-15, resulting in an easier isolation of the desired 2,5-diacetyl-isosorbide, this being an important precursor for the vasodilatory drug isosorbide-5-nitrate.",

keywords = "isosorbide, 2,5-diacetyl-isosorbide, 2-acetyl-isosorbide, green synthesis, esterification",

author = "Alexandra Inayat and {van Assche}, Alexandre and Clark, {James Hanley} and Farmer, {Thomas James}",

note = "{\textcopyright} 2017 Published by Elsevier B.V. ",

year = "2018",

month = mar,

doi = "10.1016/j.scp.2017.10.004",

language = "English",

volume = "7",

pages = "41--49",

journal = "Sustainable Chemistry and Pharmacy",

issn = "2352-5541",

publisher = "Elsevier",

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TY - JOUR

T1 - Greening the esterification between isosorbide and acetic acid

AU - Inayat, Alexandra

AU - van Assche, Alexandre

AU - Clark, James Hanley

AU - Farmer, Thomas James

PY - 2018/3

Y1 - 2018/3

N2 - This contribution deals with the investigation of greener conditions for the preparation of 2,5-diacetyl-isosorbide from the bio-based substances isosorbide and acetic acid. The influence of solvent, catalyst and reactant ratio on the course of the isosorbide conversion and selectivity to 2,5-diacetyl-isosorbide as well as to the intermediate 2-acetyl-isosorbide is examined. It was found that the conventionally used solvent toluene can be substituted by the greener solvent n-propyl acetate. Additionally, the homogeneous acid catalyst p-toluene sulfonic acid can be replaced by the heterogeneous catalyst Amberlyst-15, resulting in an easier isolation of the desired 2,5-diacetyl-isosorbide, this being an important precursor for the vasodilatory drug isosorbide-5-nitrate.

AB - This contribution deals with the investigation of greener conditions for the preparation of 2,5-diacetyl-isosorbide from the bio-based substances isosorbide and acetic acid. The influence of solvent, catalyst and reactant ratio on the course of the isosorbide conversion and selectivity to 2,5-diacetyl-isosorbide as well as to the intermediate 2-acetyl-isosorbide is examined. It was found that the conventionally used solvent toluene can be substituted by the greener solvent n-propyl acetate. Additionally, the homogeneous acid catalyst p-toluene sulfonic acid can be replaced by the heterogeneous catalyst Amberlyst-15, resulting in an easier isolation of the desired 2,5-diacetyl-isosorbide, this being an important precursor for the vasodilatory drug isosorbide-5-nitrate.

KW - isosorbide

KW - 2,5-diacetyl-isosorbide

KW - 2-acetyl-isosorbide

KW - green synthesis

KW - esterification

U2 - 10.1016/j.scp.2017.10.004

DO - 10.1016/j.scp.2017.10.004

M3 - Article

SN - 2352-5541

VL - 7

SP - 41

EP - 49

JO - Sustainable Chemistry and Pharmacy

JF - Sustainable Chemistry and Pharmacy

ER -

Greening the esterification between isosorbide and acetic acid

Abstract

Bibliographical note

Keywords

Access to Document

Projects

Sustainable Polymers

Datasets

Data supporting the publication "Greening the esterification of isosorbide with acetic acid"

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