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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (10): 1780-1784. 上一篇    下一篇

研究简报

二-(2-羟基-5-长链烷基苯基)-甲烷的合成

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

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1733

被引次数

33

以脂肪酸、苯酚为原料, 经酰化反应、酯化反应、Fries重排、黄鸣龙还原等步骤, 得到正构长链烷基酚, 再与多聚甲醛在酸性催化剂下进行缩合反应, 生成二-(2-羟基-5-长链烷基苯基)-甲烷, 用核磁共振氢谱和碳谱、红外光谱和元素分析对产物进行了结构鉴定. 据上述反应路线, 以工业品壬基酚和多聚甲醛为原料, 合成出了二-(2-羟基-5-壬基苯基)-甲烷, 并对其工艺条件进行了研究. 结果表明, 选用草酸作催化剂, 烷基酚和甲醛物质的量比为2∶1, 130 ℃反应4 h, 产物产率达到60%, 且反应转化率和选择性分别为63%和95%.

关键词: 正构长链烷基酚, 多聚甲醛, 合成, 二-(2-羟基-5-长链烷基苯基)-甲烷

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