Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (10): 1780-1784. Previous Articles     Next Articles



徐 念 ; 黎 钢*; 户帅帅 ; 祁 健 ; 刘 荣; 杨 芳; 史凤丽   

  1. (河北工业大学化工学院 天津 300130)
  • 收稿日期:2007-09-07 修回日期:2008-03-20 发布日期:2008-10-20
  • 通讯作者: 黎 钢

Synthesis of Bis(2-hydroxy-5-alkylphenyl)methane

XU, Nian ; LI, Gang*; HU, Shuai-Shuai ; QI, Jian; LIU, Rong; YANG, Fang; SHI, Feng-Li

  1. (School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130)
  • Received:2007-09-07 Revised:2008-03-20 Published:2008-10-20
  • Contact: LI, Gang

Five intermediates for preparing long chain n-alkylphenol gemini surfactants, bis(2-hydroxy-5-n- alkylphenyl)methanes, were synthesized from fatty acid, phenol, and paraformaldehyde through Friedel- Crafts acylation, esterification, Fries rearrangement, Huang Minlon reduction, and condensation, and their molecular structures were confirmed by NMR, IR spectra and elemental analysis. According to this synthetic route of bis(2-hydroxy-5-n-alkylphenyl)methane, bis(2-hydroxy-5-nonylphenyl)methane has also been synthe-sized by using isononylphenol (industrial product) and paraformaldehyde successfully. It was showed that when n-alkylphenol and paraformaldehyde at a molar ratio of 2∶1 reacted at 130 ℃ for 4 h, the product yield could reach 60% and the alkylphenol conversion and selectivity of product were 63% and 95% respectively.

Key words: paraformaldehyde, n-alkylphenol, bis(2-hydroxy-5-alkylphenyl)methane, synthesis