合成N-甲基葡萄糖亚胺的化学反应研究

南京大学学报(自然科学版) ›› 2018, Vol. 54 ›› Issue (3): 622–627.

合成N-甲基葡萄糖亚胺的化学反应研究

朱建新，候秋梅，陈慧，张家友，邓理丹，沈俭一*

出版日期:2018-05-23 发布日期:2018-05-23
作者简介:南京大学化学化工学院，南京，210023
基金资助:
国家自然科学基金面上项目（21773108）

A study on the chemical reaction for the synthesis of N-methylglucosimine

Zhu Jianxin, Hou Qiumei, Chen Hui, Zhang Jiayou, Deng Lidan, Shen Jianyi*

Online:2018-05-23 Published:2018-05-23
About author:School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, China

摘要/Abstract

摘要： 为优化N-甲基葡萄糖亚胺的合成条件，研究了水溶液中葡萄糖与甲胺缩合生成葡萄糖亚胺的动力学和热力学。结果表明，水中葡萄糖与甲胺的缩合反应较快，甲胺的平衡转化率随反应温度的升高而提高，表明该缩合反应为吸热。根据获得的动力学和热力学参数，预测了合成葡萄糖亚胺的较佳条件：在308 K的水溶液中，n(甲胺)/n(葡萄糖)=4及葡萄糖含量为10wt%时，葡萄糖的平衡转化率可达99.9%，达到平衡的时间约为28 min。

Abstract: The kinetics and thermodynamics of the condensation reaction of glucose with methylamine in aqueous solution were studied in order to optimize the conditions for the synthesis of N-methylglucosimine. The results showed that the condensation reaction took place fast in aqueous solution, and the equilibrium conversion of methylamine increased with temperature, revealing the endothermic nature of the condensation reaction. According to the kinetic and thermodynamic parameters obtained in this study, the reaction conditions could be optimized for the synthesis of N-methylglucosimine. Specifically, it is predicted that 99.9% equilibrium conversion of glucose could be reached at 308 K in 28 min when the condensation reaction was carried out in aqueous solution with the concentration of glucose of 10 wt% and the molar ratio of methylamine to glucose of 4.

朱建新，候秋梅，陈慧，张家友，邓理丹，沈俭一*. 合成N-甲基葡萄糖亚胺的化学反应研究[J]. 南京大学学报(自然科学版), 2018, 54(3): 622–627.

Zhu Jianxin, Hou Qiumei, Chen Hui, Zhang Jiayou, Deng Lidan, Shen Jianyi*. A study on the chemical reaction for the synthesis of N-methylglucosimine[J]. Journal of Nanjing University(Natural Sciences), 2018, 54(3): 622–627.

参考文献

[1] 王军, 葛虹. 烷基葡糖酰胺的合成和性能. 日用化学工业, 2002, 32(3): 54-57. (Wang J, Ge H. Synthesis and property of N-alkyl glucamide. China Surfactant Detergent ＆ Cosmetics, 2002, 32(3): 54-57.) [2] 王峰, 张高勇, 李秋小. 新一代绿色表面活性剂——烷基葡萄糖酰胺. 日用化学工业, 2002, 32(1): 43-45. (Wang F, Zhang G Y, Li Q X. A novel green surfactants—N-acyl-N-methyl glucamine. China Surfactant Detergent ＆ Cosmetics, 2002, 32(1): 43-45.) [3] Carnero Ruiz C, Hierrezuelo J M, Aguiar J, et al. Physicochemical studies on the interaction between N-decanoyl-N-methylglucamide and bovine serum albumin. Biomacromolecules, 2007, 8(8): 2497-2503. [4] 闫顺杰, 杨宗锋, 杜斌斌等. 糖基双子表面活性剂的研究进展. 日用化学工业, 2013, 43(3): 217-223. (Yan S J, Yang Z F, Du B B, et al. Progress with respect to research work on sugar-based gemini surfactants. China Surfactant Detergent ＆ Cosmetics, 2013, 43(3): 217-223.) [5] Kao J, Kelly E L, Weber V L, et al. Process for preparing amides of N-alkyl polyhydroxyalkyl amines. U. S. Patent 5777165 A, 1998-07-07. [6] Kao J, Scheibel J J, Shumate R E, et al. Process for preparing N-alkyl polyhydroxyalkyl amines in aqueous/hydroxy solvents. U. S. Patent 5625098 A, 1997-04-29. [7] Connor D S, Scheibel J J, Severson R G. Preparation of polyhydroxy fatty acid amides in the presence of solvents. W. O. Patent 1992006673 A, 1992-09-16. (请核对专利号) [8] 马立萌, 徐宝财. 新型绿色表面活性剂——烷基葡萄糖酰胺. 精细化工, 2005, 22(S): 59-61. (Ma L M, Xu B C. New green surfactant—N-Acyl-methylglucamine. Fine Chemicals, 2005, 22(S): 59-61.) [9] 唐林生, 杨晶巍, 陈恩平. 葡萄糖(基)酰胺类新型表面活性剂. 精细石油化工进展, 2002, 3(7): 32-35. (Tang L S, Yang J W, Chen E P. Novel amide surfactants based on glucose. Advances in Fine Petrochemicals, 2002, 3(7): 32-35.) [10] 徐爱忠, 王建新. N-十二烷基葡萄糖胺型表面活性剂的合成. 精细化工, 2008, 25(5): 454-458. (Xu A Z, Wang J X. Synthesis of N-alkylglucosamine surfactants. Fine Chemicals, 2008, 25(5): 454-458.) [11] 袁航空, 李秋小, 李运玲. N-十二烷基-N-甲基葡萄糖酰胺的合成. 精细化工, 2010, 27(1): 38-42, 56. (Yuan H K, Li Q X, Li Y L. Synthesis of N-lauryl-N-methylglucamide. Fine Chemicals, 2010, 27(1): 38-42, 56.) [12] 冉君花, 李和平. 烷基葡萄糖酰胺的性能与生产工艺. 精细石油化工进展, 2003, 4(3): 1-5. (Ran J H, Li H P. Properties and technology of alkyl polyglucoside amide. Advances in Fine Petrochemicals, 2003, 4(3): 1-5.) [13] 徐宝财, 刘滨. N-甲基葡萄糖胺的合成. 北京轻工业学院学报, 1997, 15(1): 58-60. (Xu B C, Liu B. Synthesis of N-methylglucamine. Journal of Beijing Institute of Light Industry, 1997, 15(1): 58-60.) [14] Melnyk L, Goncharuk V, Butnyk I, et al. Development of the sorption-membrane “green” technology for boron removal from natural and wastewaters. Desalination, 2007, 205(1-3): 206-213. [15] 邸建辉, 李云庆, 王家喜. 活性炭负载纳米镍催化葡萄糖还原胺化反应. 化工进展, 2011, 30(6): 1259-1263. (Di J H, Li Y Q, Wang J X. Catalytic reductive amination of glucose promoted by nano Ni supported on active carbon. Chemical Industry and Engineering Progress, 2011, 30(6): 1259-1263.) [16] Scheibel J J, Connor D S, Shumate R E, et al. Process for preparing N-alkyl polyhydroxy amines. U. S. Patent 5334764 A, 1994-08-02. [17] Taylor J B, Rowlinson J S. The thermodynamic properties of aqueous solutions of glucose. Transactions of the Faraday Society, 1955, 51: 1183-1192.

Metrics

Viewed

Full text

Abstract

Cited

Shared

Discussed