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Brønsted 酸性功能离子液体催化合成抗氧剂330
Thesis Advisor赵文军
Degree Grantor中国科学院研究生院
Place of Conferral北京
Degree Discipline有机化学
KeywordBrønsted 酸性离子液体 绿色化学 抗氧剂330

本论文结合抗氧剂330的传统合成技术和现代绿色化学思想和手段,基于离子液体的特殊优点如无挥发性,无污染,性质可调等优点,制备了N-烷基磺酸吡啶型酸性离子液体[N-C4H8SO3HPy]﹢X﹣,并尝试取代现有的工业无机酸催化剂,应用于抗氧剂330的合成中。实验方面,我们主要完成了以下4个方面的研究:(1)[N-C4H8SO3HPy]﹢X﹣离子液体和[N-C4H8SO3HPy]﹢X﹣离子液体制备:以吡啶,DMAP和1,4-丁烷磺酸内酯为原料,丙酮为溶剂,50℃下反应8~12 h,制备了4种Brønsted 酸性功能离子液体。系统研究了反应时间和温度对此反应的影响。结果表明,以丙酮为辅助溶剂,n(Py):n(C4H8SO3):n(酸)=1:1:1,反应8~12 h,收率分别达87.2%、93.7%、90.0%、92.1%;n(DMAP):n(C4H8SO3):n(酸)=1:1:1,反应8~12 h,收率分别为92.7%、91.1%、87.2%、94.5%。(2)3,5-二叔丁基-4-羟基苄甲醚的制备:探讨了包括反应机理、催化剂的选择(二乙基胺、二甲基胺、NaOH、KOH、叔丁醇钠)、反应温度、反应时间对3,5-二叔丁基-4-羟基苄甲醚收率的影响等因素对反应的影响。120℃下,n(2,6-二叔丁基苯酚):n(甲醛)=1:1.2,适量二甲胺水溶液的催化下反应3 h,收率达90.4%。(3)利用上述制备的两个系列,8种酸性离子液体催化合成抗氧剂330。系统研究了催化剂用量、反应温度、反应时间、催化剂重复使用对收率的影响。结果表明,在 0 ℃下,以CH2Cl2为辅助溶剂,n([N-C4H8SO3HPy]+HSO4-):n(1,3,5-三甲苯):n(3,5-二叔丁基-4-羟基苄甲醚)=1:3:10,反应3 h,收率达89.6%。离子液体表现出良好的催化性能和重复使用性能。反应条件温和,后处理简单,获得了比硫酸更高的收率。

Other Abstract

The antioxidant was prepared by 1, 3, 5-trimethylbenzene and 3,5-di-tertbutyl-4-hydroxybenzylmethylether with the catalysis of Brønsted acidic functional ionic liquids, which is an attempt of Green Chemistry and meaningful in Chemical Industry. We have accomplished four aspects of research experimentally as follow: Preparation of [N-C4H8SO3HPy]﹢X﹣(X: HSO4﹣, p-TSA﹣, Cl﹣, H2PO4﹣) and [N-C4H8SO3HDMAP]﹢X﹣. The result shows that on the condition of n(pyridine): n(C4H8SO3):n (acid)=1: 1: 1, reacted in acetone in 50℃ for 8~12 h, the yields were 87.2%, 93.7%, 90.0%, 92.1%. P.S. The acids are H2SO4, Hp-TSA, H3PO4, HCl. On the condition of n(DMAP): n(C4H8SO3): n(acid)=1: 1: 1, reacted in acetone in 50℃ for 8~12 h, the yields were 92.7%, 91.1%, 87.2%, 94.5%. Preparation of 3, 5-di-tertbutyl-4-hydroxybenzyl methylether: the effects of mechanism of different catalysts, the election of catalysts ((CH3)2NH, (CH2CH3)2NH, KOH, NaOH, t-BuONa.), reaction time, reaction temperature were investigated. 3, 5-di-tertbutyl-4-hydroxybenzylmethylether were prepared by 2,6-ditertbutylbenzene and formaldehyde in the mass ratio of 1:1.2 by 3h reaction for a yield of 90.4%. Synthesis of Antioxidant 330: 8 kinds of Brønsted acidic functional ionic liquids were employed to catalyze an electrophilic substituted reaction to synthesize antioxidant 330: 1, 3, 5-trimethyl-2, 4, 6-tris(3,5-di-tertbutyl-4-hydroxybenzyl)benzene. The optimal reaction condition is : n([N-C4H8SO3HPyridine]﹢HSO4﹣):n(1,3,5-trimethylbenzene): n(3,5-di-tertbutyl-4-hydroxybenzylmethylether)=1: 3: 10, CH2Cl2 as co-solvent, and temperature is 0 ℃ for 3 h, the yield is 89.6%.

Document Type学位论文
Recommended Citation
GB/T 7714
陈阳. Brønsted 酸性功能离子液体催化合成抗氧剂330[D]. 北京. 中国科学院研究生院,2008.
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