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

Detalhes bibliográficos
Autor(a) principal: Barbosa, Sandro L.
Data de Publicação: 2022
Outros Autores: Nelson, David Lee, Freitas, Milton de S., dos Santos, Wallans Torres Pio, Klein, Stanlei I. [UNESP], Clososki, Giuliano C., Caires, Franco J., Wentz, Alexandre P.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.3390/molecules27154767
http://hdl.handle.net/11449/241460
Resumo: SiO2–SO3H, with a surface area of 115 m2/g and 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 over 40 min at 120 °C in MeOH. The resulting crude product was purified by flash chromatography. The catalyst could be reused three times.
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spelling Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiationdeacetylation (acyl nucleophilic substitution)green chemistrymethyl salicylatemethylating agentsolid acid catalystsulfonated silica catalyst (SiO2–SO3H)SiO2–SO3H, with a surface area of 115 m2/g and 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 over 40 min at 120 °C in MeOH. The resulting crude product was purified by flash chromatography. The catalyst could be reused three times.SENAI CIMATECDepartment of Pharmacy Universidade Federal dos Vales do Jequitinhonha e Mucuri-UFVJM, Campus JK, Rodovia MGT 367—Km 583, no 5.000, Alto da JacubaDepartment of General and Inorganic Chemistry Institute of Chemistry São Paulo State University-Unesp, R. Prof, Francisco Degni 55, QuitandinhaDepartment of Physics and Chemistry Faculdade de Ciências Farmacêuticas de Ribeirão Preto São Paulo University-USP, Av. do Café s/nCentro Universitário SENAI-CIMATEC, Av. Orlando Gomes, 1845, PiatãDepartment of General and Inorganic Chemistry Institute of Chemistry São Paulo State University-Unesp, R. Prof, Francisco Degni 55, QuitandinhaUniversidade Federal de Viçosa (UFV)Universidade Estadual Paulista (UNESP)Universidade de São Paulo (USP)Centro Universitário SENAI-CIMATECBarbosa, Sandro L.Nelson, David LeeFreitas, Milton de S.dos Santos, Wallans Torres PioKlein, Stanlei I. [UNESP]Clososki, Giuliano C.Caires, Franco J.Wentz, Alexandre P.2023-03-01T21:04:21Z2023-03-01T21:04:21Z2022-08-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.3390/molecules27154767Molecules, v. 27, n. 15, 2022.1420-3049http://hdl.handle.net/11449/24146010.3390/molecules271547672-s2.0-85135371341Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengMoleculesinfo:eu-repo/semantics/openAccess2023-03-01T21:04:22Zoai:repositorio.unesp.br:11449/241460Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T14:50:10.689180Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation
title Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation
spellingShingle Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation
Barbosa, Sandro L.
deacetylation (acyl nucleophilic substitution)
green chemistry
methyl salicylate
methylating agent
solid acid catalyst
sulfonated silica catalyst (SiO2–SO3H)
title_short Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation
title_full Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation
title_fullStr Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation
title_full_unstemmed Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation
title_sort Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation
author Barbosa, Sandro L.
author_facet Barbosa, Sandro L.
Nelson, David Lee
Freitas, Milton de S.
dos Santos, Wallans Torres Pio
Klein, Stanlei I. [UNESP]
Clososki, Giuliano C.
Caires, Franco J.
Wentz, Alexandre P.
author_role author
author2 Nelson, David Lee
Freitas, Milton de S.
dos Santos, Wallans Torres Pio
Klein, Stanlei I. [UNESP]
Clososki, Giuliano C.
Caires, Franco J.
Wentz, Alexandre P.
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade Federal de Viçosa (UFV)
Universidade Estadual Paulista (UNESP)
Universidade de São Paulo (USP)
Centro Universitário SENAI-CIMATEC
dc.contributor.author.fl_str_mv Barbosa, Sandro L.
Nelson, David Lee
Freitas, Milton de S.
dos Santos, Wallans Torres Pio
Klein, Stanlei I. [UNESP]
Clososki, Giuliano C.
Caires, Franco J.
Wentz, Alexandre P.
dc.subject.por.fl_str_mv deacetylation (acyl nucleophilic substitution)
green chemistry
methyl salicylate
methylating agent
solid acid catalyst
sulfonated silica catalyst (SiO2–SO3H)
topic deacetylation (acyl nucleophilic substitution)
green chemistry
methyl salicylate
methylating agent
solid acid catalyst
sulfonated silica catalyst (SiO2–SO3H)
description SiO2–SO3H, with a surface area of 115 m2/g and 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 over 40 min at 120 °C in MeOH. The resulting crude product was purified by flash chromatography. The catalyst could be reused three times.
publishDate 2022
dc.date.none.fl_str_mv 2022-08-01
2023-03-01T21:04:21Z
2023-03-01T21:04:21Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.3390/molecules27154767
Molecules, v. 27, n. 15, 2022.
1420-3049
http://hdl.handle.net/11449/241460
10.3390/molecules27154767
2-s2.0-85135371341
url http://dx.doi.org/10.3390/molecules27154767
http://hdl.handle.net/11449/241460
identifier_str_mv Molecules, v. 27, n. 15, 2022.
1420-3049
10.3390/molecules27154767
2-s2.0-85135371341
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Molecules
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.source.none.fl_str_mv Scopus
reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
repository.mail.fl_str_mv
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