Sn(II)-catalyzed β-citronellol esterification: a Brønsted acid-free process for synthesis of fragrances at room temperature

Detalhes bibliográficos
Autor(a) principal: Silva, M. J. da
Data de Publicação: 2015
Outros Autores: Julio, A. A., Santos, K. T. dos
Tipo de documento: Artigo
Idioma: eng
Título da fonte: LOCUS Repositório Institucional da UFV
Texto Completo: https://doi.org/10.1039/C4CY01069H
http://www.locus.ufv.br/handle/123456789/24065
Resumo: Simple SnCl2·2H2O was demonstrated to be able to catalyze β-citronellol esterification with acetic acid at room temperature under solvent-free conditions, achieving high conversion and ester selectivity (ca. 88% and 99%, respectively). Tin(II) chloride is a stable and water-tolerant Lewis acid that is commercially available and less corrosive than Brønsted acid catalysts. This selective process is an attractive alternative to the mineral acid-catalyzed process because it avoids product neutralization common in those reactions. The effects of main reaction parameters such as reactant stoichiometry, temperature, solvent, and catalyst concentration were assessed. Among the tin catalysts evaluated, SnCl2 was the most active and selective. Moreover, SnCl2 was as active as sulfuric and p-toluenesulfonic acid catalysts, the Brønsted acids investigated herein, with additional advantages of being a solid and less corrosive catalyst.
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spelling Silva, M. J. daJulio, A. A.Santos, K. T. dos2019-03-21T14:44:43Z2019-03-21T14:44:43Z20152044-4761https://doi.org/10.1039/C4CY01069Hhttp://www.locus.ufv.br/handle/123456789/24065Simple SnCl2·2H2O was demonstrated to be able to catalyze β-citronellol esterification with acetic acid at room temperature under solvent-free conditions, achieving high conversion and ester selectivity (ca. 88% and 99%, respectively). Tin(II) chloride is a stable and water-tolerant Lewis acid that is commercially available and less corrosive than Brønsted acid catalysts. This selective process is an attractive alternative to the mineral acid-catalyzed process because it avoids product neutralization common in those reactions. The effects of main reaction parameters such as reactant stoichiometry, temperature, solvent, and catalyst concentration were assessed. Among the tin catalysts evaluated, SnCl2 was the most active and selective. Moreover, SnCl2 was as active as sulfuric and p-toluenesulfonic acid catalysts, the Brønsted acids investigated herein, with additional advantages of being a solid and less corrosive catalyst.engCatalysis Science & TechnologyVolume 5, Issue 2, Pages 1261–1266, 2015Royal Society of Chemistryinfo:eu-repo/semantics/openAccessSn(II)-catalyzedβ-citronellol esterificationBrønsted acid-free processSn(II)-catalyzed β-citronellol esterification: a Brønsted acid-free process for synthesis of fragrances at room temperatureinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfreponame:LOCUS Repositório Institucional da UFVinstname:Universidade Federal de Viçosa (UFV)instacron:UFVORIGINALartigo.pdfartigo.pdfTexto completoapplication/pdf311829https://locus.ufv.br//bitstream/123456789/24065/1/artigo.pdfdfd9ac91291a57d4bf7f02906448cfefMD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://locus.ufv.br//bitstream/123456789/24065/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52123456789/240652019-03-21 11:47:34.95oai:locus.ufv.br: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Repositório InstitucionalPUBhttps://www.locus.ufv.br/oai/requestfabiojreis@ufv.bropendoar:21452019-03-21T14:47:34LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)false
dc.title.en.fl_str_mv Sn(II)-catalyzed β-citronellol esterification: a Brønsted acid-free process for synthesis of fragrances at room temperature
title Sn(II)-catalyzed β-citronellol esterification: a Brønsted acid-free process for synthesis of fragrances at room temperature
spellingShingle Sn(II)-catalyzed β-citronellol esterification: a Brønsted acid-free process for synthesis of fragrances at room temperature
Silva, M. J. da
Sn(II)-catalyzed
β-citronellol esterification
Brønsted acid-free process
title_short Sn(II)-catalyzed β-citronellol esterification: a Brønsted acid-free process for synthesis of fragrances at room temperature
title_full Sn(II)-catalyzed β-citronellol esterification: a Brønsted acid-free process for synthesis of fragrances at room temperature
title_fullStr Sn(II)-catalyzed β-citronellol esterification: a Brønsted acid-free process for synthesis of fragrances at room temperature
title_full_unstemmed Sn(II)-catalyzed β-citronellol esterification: a Brønsted acid-free process for synthesis of fragrances at room temperature
title_sort Sn(II)-catalyzed β-citronellol esterification: a Brønsted acid-free process for synthesis of fragrances at room temperature
author Silva, M. J. da
author_facet Silva, M. J. da
Julio, A. A.
Santos, K. T. dos
author_role author
author2 Julio, A. A.
Santos, K. T. dos
author2_role author
author
dc.contributor.author.fl_str_mv Silva, M. J. da
Julio, A. A.
Santos, K. T. dos
dc.subject.pt-BR.fl_str_mv Sn(II)-catalyzed
β-citronellol esterification
Brønsted acid-free process
topic Sn(II)-catalyzed
β-citronellol esterification
Brønsted acid-free process
description Simple SnCl2·2H2O was demonstrated to be able to catalyze β-citronellol esterification with acetic acid at room temperature under solvent-free conditions, achieving high conversion and ester selectivity (ca. 88% and 99%, respectively). Tin(II) chloride is a stable and water-tolerant Lewis acid that is commercially available and less corrosive than Brønsted acid catalysts. This selective process is an attractive alternative to the mineral acid-catalyzed process because it avoids product neutralization common in those reactions. The effects of main reaction parameters such as reactant stoichiometry, temperature, solvent, and catalyst concentration were assessed. Among the tin catalysts evaluated, SnCl2 was the most active and selective. Moreover, SnCl2 was as active as sulfuric and p-toluenesulfonic acid catalysts, the Brønsted acids investigated herein, with additional advantages of being a solid and less corrosive catalyst.
publishDate 2015
dc.date.issued.fl_str_mv 2015
dc.date.accessioned.fl_str_mv 2019-03-21T14:44:43Z
dc.date.available.fl_str_mv 2019-03-21T14:44:43Z
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 https://doi.org/10.1039/C4CY01069H
http://www.locus.ufv.br/handle/123456789/24065
dc.identifier.issn.none.fl_str_mv 2044-4761
identifier_str_mv 2044-4761
url https://doi.org/10.1039/C4CY01069H
http://www.locus.ufv.br/handle/123456789/24065
dc.language.iso.fl_str_mv eng
language eng
dc.relation.ispartofseries.pt-BR.fl_str_mv Volume 5, Issue 2, Pages 1261–1266, 2015
dc.rights.driver.fl_str_mv Royal Society of Chemistry
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Royal Society of Chemistry
eu_rights_str_mv openAccess
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dc.publisher.none.fl_str_mv Catalysis Science & Technology
publisher.none.fl_str_mv Catalysis Science & Technology
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reponame_str LOCUS Repositório Institucional da UFV
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