Hydrophobic Perfluoroalkylsulfonyl Imide Solid Acid as Catalyst of Esterification and Pechmann Condensation

doi:10.6023/cjoc201406027

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (11): 2255-2261.DOI: 10.6023/cjoc201406027 Previous Articles Next Articles

疏水性全氟烷基磺酰亚胺固体酸催化酯化与Pechmann缩合

马忠华, 贺梦丽, 张海娟, 马敬中, 原弘

华中农业大学理学院化学系武汉 430070

收稿日期:2014-06-19 修回日期:2014-07-13 发布日期:2014-07-17
通讯作者: 原弘,yuanhong@mail.hzau.edu.cn E-mail:yuanhong@mail.hzau.edu.cn
基金资助:
国家自然科学基金(Nos.21172083, 21277055)资助项目.

Hydrophobic Perfluoroalkylsulfonyl Imide Solid Acid as Catalyst of Esterification and Pechmann Condensation

Ma Zhonghua, He Mengli, Zhang Haijuan, Ma Jingzhong, Yuan Hong

Department of Chemistry, College of Sciences, Huazhong Agricultural University, Wuhan 430070

Received:2014-06-19 Revised:2014-07-13 Published:2014-07-17
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.21172083, 21277055).

Polydivinylbene-bound perfluoroalkylsulfonyl imide polymers with excellent acidity and hydrophobicity were prepared by copolymerization under solvothermal conditions (noted as H-PDVB-x-SSFAI). H-PDVB-x-SSFAI catalyzed the esterification of long chain fatty acid with methanol/ethanol in water, affording 88% conversion, which increased to 95% without additional water within 5~6 h. The catalytic esterification of short chain fatty acid with both primary alcohol and secondary alcohol was carried out smoothly, for example, 87%~92% of conversion was gave for cyclohexanol within 4 h. H-PDVB-x-SSFAI was cycled for at least seven runs with stable catalysis efficiency. On the other hand, H-PDVB-x-SSFAI was used to catalyze Pechmann condensation to give 7-hydroxyl coumarin under 140 ℃, affording ca. 90% of average isolated yield, and the catalyst could be cycled for 4 runs. Furthermore, the excellent catalytic performance is attributed to combination of excellent acidity and hydrophobicity.

Key words: perfluoroalkylsulfonyl imide, heterogeneous catalysis, esterification, Pechmann condensation

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Ma Zhonghua, He Mengli, Zhang Haijuan, Ma Jingzhong, Yuan Hong. Hydrophobic Perfluoroalkylsulfonyl Imide Solid Acid as Catalyst of Esterification and Pechmann Condensation[J]. Chin. J. Org. Chem., 2014, 34(11): 2255-2261.

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疏水性全氟烷基磺酰亚胺固体酸催化酯化与Pechmann缩合

Hydrophobic Perfluoroalkylsulfonyl Imide Solid Acid as Catalyst of Esterification and Pechmann Condensation

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