Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Tandem Transesterification-Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Micro-wave Irradiation

Sandro Luiz Barbosa Dos Santos
* ORCID logo ,
David Lee Nelson
ORCID logo ,
Milton Souza Freita
,
Wallans Torres Pio Dos Santos
,
Stanlei Ivair Klein
,
Giuliano Cesar Clososki
,
Franco Jazon Caires
,
Alexandre Pereira Wentz
Version 1 : Received: 29 May 2022 / Approved: 6 June 2022 / Online: 6 June 2022 (03:45:09 CEST)

A peer-reviewed article of this Preprint also exists.

Barbosa, S.L.; Nelson, D.L.; Freitas, M.S.; dos Santos, W.T.P.; Klein, S.I.; Clososki, G.C.; Caires, F.J.; Wentz, A.P. Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation. Molecules 2022, 27, 4767. Barbosa, S.L.; Nelson, D.L.; Freitas, M.S.; dos Santos, W.T.P.; Klein, S.I.; Clososki, G.C.; Caires, F.J.; Wentz, A.P. Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation. Molecules 2022, 27, 4767.

DOI: 10.3390/molecules27154767

Abstract

SiO2-SO3H, with a surface area of 115 m2/g, pore volume of 0.38 cm3g-1 and 1.32 mmol H+/g, was used as a 20% w/w catalyst for the preparation of methyl salicylate (Wintergreen oil or MS) from acetylsalicylic acid (ASA). A 94% conversion was achieved in a microwave reactor during 40.0 minutes at 120 oC in MeOH. The resulting crude product was purified by flash chromatography. The catalyst could be re-used three times.

Keywords

Sulfonated silica catalyst (SiO2-SO3H); methyl salicylate; green chemistry; methylating agent; deacetylation (acyl nucleophilic substitution); solid acid catalyst

Subject

CHEMISTRY, Organic Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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