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化学学报
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化学学报 ›› 2004, Vol. 62 ›› Issue (9): 895-900. 上一篇    下一篇

研究论文

N-硬脂酰-L-谷氨酸及其乙酯衍生物的合成与成胶性质研究

高鹏1,2, 刘立柱1, 詹传郎2, 周延彪2, 刘鸣华2   

  1. 1. 哈尔滨理工大学,材料科学与工程学院,哈尔滨,150080;
    2. 中国科学院化学研究所,分子科学中心胶体与界面科学重点实验室,北京,100080
  • 投稿日期:2003-09-15 修回日期:2004-01-15 发布日期:2014-02-17
  • 通讯作者: 詹传郎,E-mail:clzhan@iccas.ac.cn;Tel:86-10-82615803;Fax:86-10-62559373 E-mail:clzhan@iccas.ac.cn
  • 基金资助:
    国家自然科学基金(Nos.29992593,50172049),中国科学院分子科学中心创新基金(No.CMS-CX200203),国家"973"规划(No.G2000078103)资助项目.

Synthesis and Gelation of N-Stearoyl-L-glutamic Acid and N-Stearoyl-L-glutamic Diethyl Ester

GAO Peng1,2, LIU Li-Zhu1, ZHAN Chuan-Lang2, ZHOU Yan-Biao2, LIU Ming-Hua2   

  1. 1. College of Material Science and Engineering, Harbin University of Science and Technology, Harbin 150080;
    2. CAS Key Laboratory of Colloid and Interface Science, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080
  • Received:2003-09-15 Revised:2004-01-15 Published:2014-02-17

PDF

543

被引次数

14

研究了N-硬脂酰-L-谷氨酸(C18-Glu)--一个具有多个氢键位点的有机胶凝剂分子及其乙酯(C18-Glu-2ES)衍生物的合成与成胶性质.文献报道的合成方法是将硬脂酰氯滴加到L-谷氨酸钠的丙酮与水的混合溶液中,但我们的多次实验结果表明该合成方法的可操作性比较差,究其原因主要在于:反应的副产物之一盐酸的强酸性容易导致反应液的局部强酸性环境,而使反应产生的C18-Glu分子继续与L-谷氨酸反应,这大大增加了产物的后处理难度,很难得到高纯度的产物.因此,我们改用L-谷氨酸二乙酯为原料,在二环己基碳酰亚胺催化下或通过硬脂酰氯得到所需的高纯度产物.在此基础上,研究了合成的C18-Glu及C18-Glu-2ES的成胶性质,结果表明C18-Glu-2ES具有比C18-Glu更广的成胶范围和更小的成胶浓度.

关键词: 有机凝胶, 硬脂酰谷氨酸, 自组装, 微结构

Synthesis of N stearoyl-L-glutamic acid (C18-Glu), a new gelator with multi H bonding sites, and N stearoyl-L-glutamic diethyl ester (C18-Glu-2ES) were reported.The previously reported synthetic route of C18-Glu is that stearoyl chloride was dropwise added into disodium L glutamate solution in a mixture of acetone and water ( J.Am.Oil Chem.Soc .1972, 49, 157 and Langmiur , 2001, 17, 1317).However, our experimental results indicated that one of the by product HCl, could catalyze the yielded C18-Glu to react further with L glutamate to give more side-products.Therefore, the further workup became more difficult and the pure C18-Glu was difficult to be obtained.Here, we synthesized C18-Glu by the following two routes.One is from L-glutamic diethyl ester and stearic acid using dicyclohexylcarbodiimide (DCC) as a catalyzer.The other is from stearoyl chloride and L-glutamic diethyl ester.These two synthetic routes can all give out C18-Glu with satisfactory characteristic data.Moreover, The gelating properties of C18-Glu and C18-Glu-2ES were also investigated.C18-Glu can gel chloroform and 1:1 mixed ethanol/water, while C18-Glu-2ES can form organogels in more solvents such as petroleum ether, hexane, acetone, ethanol, and 3:7 mixed ethanol/water.AFM images indicated that C18-Glu self-assembled into nanowires in chloroform, while C18-Glu-2ES into lamellar-like microstructures in 3:7 mixed ethanol/water.

Key words: organogel, N-stearoyl-L-glutamic acid, self-assembly, microstrutcure