Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (03): 439-443. Previous Articles     Next Articles

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2,6-二(5-烷基水杨基)-4-烷基苯酚的合成

刘荣,黎钢*,杨芳,祁健,徐念
张松梅 王中旭   

  1. (河北工业大学化工学院 天津 300130)
  • 收稿日期:2009-03-18 修回日期:2009-07-03 发布日期:2010-03-28
  • 通讯作者: 刘荣 E-mail:ligang@hebut.edu.cn; shangsuijun@163.com

Synthesis of 2,6-Bis(5-alkylsalicyl)-4-alkylphenol

Liu Rong,Li Gang*,Yang Fang,Qi Jian,Xu Nian
Zhang Songmei,Wang Zhongxu   

  1. (School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130)
  • Received:2009-03-18 Revised:2009-07-03 Published:2010-03-28

Five intermediates for preparing long chain n-alkylphenol trimeric surfactants, 2,6-bis(5-alkylsalicyl)-4-alkylphenol, were synthesized from fatty acid, phenol, and paraformaldehyde through Friedel-Crafts acylation, esterification, Fries rearrangement, Huang Minlon reduction, alkaline catalytic reaction, and condensation reaction by virtue of solid superacid, and their molecular structures were confirmed by NMR, IR techniques and elemental analysis. According to this synthetic route of 2,6-bis(5-alkylsalicyl)-4-alkylphenol, 2,6-bis(5-nonylsalicyl)-4-nonylphenol has also been synthesized by using isononylphenol (industrial product) and paraformaldehyde successfully. It was showed that when 2,6-bis(hydroxymethyl)-4-alkylphenol and alkylphenol were reacted at a molar ratio of 1∶2 at 140 ℃ for 2 h, the product yield could reach 95%.

Key words: solid superacid, alkylphenol, paraformaldehyde, catalysis, synthesis