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二-(2-羟基-5-长链烷基苯基)-甲烷的合成
引用本文:徐念,黎钢,户帅帅,祁健,刘荣,杨芳,史凤丽.二-(2-羟基-5-长链烷基苯基)-甲烷的合成[J].有机化学,2008,28(10):1780-1784.
作者姓名:徐念  黎钢  户帅帅  祁健  刘荣  杨芳  史凤丽
作者单位:河北工业大学化工学院,天津,300130
摘    要: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  二-(2-羟基-5-长链烷基苯基)-甲烷  合成
收稿时间:2007-9-7
修稿时间:2008-3-20

Synthesis of Bis(2-hydroxy-5-alkylphenyl)methane
XU,Nian,LI,Gang,HU,Shuai-Shuai,QI,Jian,LIU,Rong,YANG,Fang,SHI,Feng-Li.Synthesis of Bis(2-hydroxy-5-alkylphenyl)methane[J].Chinese Journal of Organic Chemistry,2008,28(10):1780-1784.
Authors:XU  Nian  LI  Gang  HU  Shuai-Shuai  QI  Jian  LIU  Rong  YANG  Fang  SHI  Feng-Li
Institution:(School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130)
Abstract: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.
Keywords:n-alkylphenol  paraformaldehyde  bis(2-hydroxy-5-alkylphenyl)methane  synthesis
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