Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation
SiO<sub>2</sub>–SO<sub>3</sub>H, with a surface area of 115 m<sup>2</sup>/g and pore volume of 0.38 cm<sup>3</sup>g<sup>−1</sup>, and 1.32 mmol H<sup>+</sup>/g was used as a 20% <i>w</i>/<i>w</i> catalyst...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/15/4767 |
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| author | Sandro L. Barbosa David Lee Nelson Milton de S. Freitas Wallans Torres Pio dos Santos Stanlei I. Klein Giuliano C. Clososki Franco J. Caires Alexandre P. Wentz |
| author_facet | Sandro L. Barbosa David Lee Nelson Milton de S. Freitas Wallans Torres Pio dos Santos Stanlei I. Klein Giuliano C. Clososki Franco J. Caires Alexandre P. Wentz |
| author_sort | Sandro L. Barbosa |
| collection | DOAJ |
| description | SiO<sub>2</sub>–SO<sub>3</sub>H, with a surface area of 115 m<sup>2</sup>/g and pore volume of 0.38 cm<sup>3</sup>g<sup>−1</sup>, and 1.32 mmol H<sup>+</sup>/g was used as a 20% <i>w</i>/<i>w</i> 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. |
| first_indexed | 2024-03-09T05:10:48Z |
| format | Article |
| id | doaj.art-2fe4f21285db4cbd86a650f080532293 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T05:10:48Z |
| publishDate | 2022-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-2fe4f21285db4cbd86a650f0805322932023-12-03T12:49:35ZengMDPI AGMolecules1420-30492022-07-012715476710.3390/molecules27154767Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave IrradiationSandro L. Barbosa0David Lee Nelson1Milton de S. Freitas2Wallans Torres Pio dos Santos3Stanlei I. Klein4Giuliano C. Clososki5Franco J. Caires6Alexandre P. Wentz7Department of Pharmacy, Universidade Federal dos Vales do Jequitinhonha e Mucuri-UFVJM, Campus JK, Rodovia MGT 367—Km 583, n<sup>o</sup> 5.000, Alto da Jacuba, Diamantina 39100-000, BrazilDepartment of Pharmacy, Universidade Federal dos Vales do Jequitinhonha e Mucuri-UFVJM, Campus JK, Rodovia MGT 367—Km 583, n<sup>o</sup> 5.000, Alto da Jacuba, Diamantina 39100-000, BrazilDepartment of Pharmacy, Universidade Federal dos Vales do Jequitinhonha e Mucuri-UFVJM, Campus JK, Rodovia MGT 367—Km 583, n<sup>o</sup> 5.000, Alto da Jacuba, Diamantina 39100-000, BrazilDepartment of Pharmacy, Universidade Federal dos Vales do Jequitinhonha e Mucuri-UFVJM, Campus JK, Rodovia MGT 367—Km 583, n<sup>o</sup> 5.000, Alto da Jacuba, Diamantina 39100-000, BrazilDepartment of General and Inorganic Chemistry, Institute of Chemistry, São Paulo State University-Unesp, R. Prof. Francisco Degni 55, Quitandinha, Araraquara 14800-900, BrazilDepartment of Physics and Chemistry, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, São Paulo University-USP, Av. do Café s/n, Ribeirão Preto 14040-903, BrazilDepartment of Physics and Chemistry, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, São Paulo University-USP, Av. do Café s/n, Ribeirão Preto 14040-903, BrazilCentro Universitário SENAI-CIMATEC, Av. Orlando Gomes, 1845, Piatã, Salvador 41650-010, BrazilSiO<sub>2</sub>–SO<sub>3</sub>H, with a surface area of 115 m<sup>2</sup>/g and pore volume of 0.38 cm<sup>3</sup>g<sup>−1</sup>, and 1.32 mmol H<sup>+</sup>/g was used as a 20% <i>w</i>/<i>w</i> 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.https://www.mdpi.com/1420-3049/27/15/4767sulfonated silica catalyst (SiO<sub>2</sub>–SO<sub>3</sub>H)methyl salicylategreen chemistrymethylating agentdeacetylation (acyl nucleophilic substitution)solid acid catalyst |
| spellingShingle | Sandro L. Barbosa David Lee Nelson Milton de S. Freitas Wallans Torres Pio dos Santos Stanlei I. Klein Giuliano C. Clososki Franco J. Caires Alexandre P. Wentz Tandem Transesterification–Esterification Reactions Using a Hydrophilic Sulfonated Silica Catalyst for the Synthesis of Wintergreen Oil from Acetylsalicylic Acid Promoted by Microwave Irradiation Molecules sulfonated silica catalyst (SiO<sub>2</sub>–SO<sub>3</sub>H) methyl salicylate green chemistry methylating agent deacetylation (acyl nucleophilic substitution) solid acid catalyst |
| title | 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_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_sort | tandem transesterification esterification reactions using a hydrophilic sulfonated silica catalyst for the synthesis of wintergreen oil from acetylsalicylic acid promoted by microwave irradiation |
| topic | sulfonated silica catalyst (SiO<sub>2</sub>–SO<sub>3</sub>H) methyl salicylate green chemistry methylating agent deacetylation (acyl nucleophilic substitution) solid acid catalyst |
| url | https://www.mdpi.com/1420-3049/27/15/4767 |
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