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Greening the esterification between isosorbide and acetic acid

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JournalSustainable Chemistry and Pharmacy
DateAccepted/In press - 15 Oct 2017
DateE-pub ahead of print - 6 Nov 2017
DatePublished (current) - Mar 2018
Volume7
Number of pages9
Pages (from-to)41-49
Early online date6/11/17
Original languageEnglish

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.

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© 2017 Published by Elsevier B.V.

    Research areas

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

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