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采用亲水磺酸化硅胶催化剂的串联酯交换-酯化反应,在微波辐射促进下,从乙酰水杨酸合成冬青油。

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

机构信息

Department of Pharmacy, Universidade Federal dos Vales do Jequitinhonha e Mucuri-UFVJM, Campus JK, Rodovia MGT 367-Km 583, no 5.000, Alto da Jacuba, Diamantina 39100-000, Brazil.

Department of General and Inorganic Chemistry, Institute of Chemistry, São Paulo State University-Unesp, R. Prof. Francisco Degni 55, Quitandinha, Araraquara 14800-900, Brazil.

出版信息

Molecules. 2022 Jul 26;27(15):4767. doi: 10.3390/molecules27154767.

DOI:10.3390/molecules27154767
PMID:35897943
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9330306/
Abstract

SiO-SOH, with a surface area of 115 m/g and pore volume of 0.38 cmg, and 1.32 mmol H/g was used as a 20% / 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.

摘要

SiO-SOH,比表面积为 115 m²/g,孔体积为 0.38 cm³/g,氢量为 1.32 mmol/g,用作乙酰水杨酸(ASA)制备水杨酸甲酯(冬青油或 MS)的 20% /催化剂。在甲醇中于 120°C 下在微波反应器中反应 40 分钟即可实现 94%的转化率。所得粗产物通过快速色谱法纯化。催化剂可重复使用三次。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d462/9330306/46e0fdcda386/molecules-27-04767-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d462/9330306/a906322cd09b/molecules-27-04767-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d462/9330306/8b5cd6b59fd4/molecules-27-04767-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d462/9330306/ff4ab3c5a54a/molecules-27-04767-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d462/9330306/46e0fdcda386/molecules-27-04767-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d462/9330306/a906322cd09b/molecules-27-04767-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d462/9330306/8b5cd6b59fd4/molecules-27-04767-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d462/9330306/ff4ab3c5a54a/molecules-27-04767-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d462/9330306/46e0fdcda386/molecules-27-04767-g004.jpg

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本文引用的文献

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Volatile Constituent Analysis of Wintergreen Essential Oil and Comparison with Synthetic Methyl Salicylate for Authentication.冬青精油的挥发性成分分析及其与合成水杨酸甲酯的鉴别比较
Plants (Basel). 2022 Apr 17;11(8):1090. doi: 10.3390/plants11081090.
2
Catalytic Transformation of Triglycerides to Biodiesel with SiO-SOH and Quaternary Ammonium Salts in Toluene or DMSO.甲苯或 DMSO 中 SiO-SOH 和季铵盐催化甘油三酯转化为生物柴油。
Molecules. 2022 Jan 30;27(3):953. doi: 10.3390/molecules27030953.
3
Dehydration of D-fructose to 5-hydroxymethyl-2-furfural in DMSO using a hydrophilic sulfonated silica catalyst in a process promoted by microwave irradiation.
在微波辐射促进的过程中,使用亲水性磺化硅胶催化剂将 D-果糖脱水为 5-羟甲基糠醛在 DMSO 中。
Sci Rep. 2021 Jan 21;11(1):1919. doi: 10.1038/s41598-020-80285-2.
4
Using wintergreen oil for mounting mosquito larvae: a safer alternative to xylene.使用冬青油固定蚊虫幼虫:一种比二甲苯更安全的替代品。
Biotech Histochem. 2016;91(1):63-70. doi: 10.3109/10520295.2015.1074286. Epub 2015 Nov 3.
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Green chemistry: principles and practice.绿色化学:原理与实践。
Chem Soc Rev. 2010 Jan;39(1):301-12. doi: 10.1039/b918763b. Epub 2009 Nov 20.
6
Use of a synthetic salicylic acid analog to investigate the roles of methyl salicylate and its esterases in plant disease resistance.使用一种合成水杨酸类似物来研究水杨酸甲酯及其酯酶在植物抗病性中的作用。
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7
Field-testing of methyl salicylate for recruitment and retention of beneficial insects in grapes and hops.用于葡萄和啤酒花中有益昆虫招募与留存的水杨酸甲酯田间试验。
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