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山东大学学报（理学版） ›› 2018, Vol. 53 ›› Issue (3): 88-94.doi: 10.6040/j.issn.1671-9352.0.2017.377

• • 上一篇    

1,3,5-均三嗪三醇与二乙烯三胺的催化胺化反应

孟丽1,王倩2,柴树1,朱维群1*   

  1. 1.山东大学化学与化工学院, 山东 济南 250100;2.山东大学国家胶体材料工程技术研究中心, 山东 济南 250100
  • 收稿日期:2017-07-31 出版日期:2018-03-20 发布日期:2018-03-13
  • 通讯作者: 朱维群(1961— ),男,教授,硕士生导师,研究方向为CO2封存利用及脱硫脱硝理论和技术开发应用研究.E-mail:zhuwq@sdu.edu.cn E-mail:mengli0621@163.com
  • 作者简介:孟丽(1992— ),女,硕士,研究方向为CO2封存利用及1,3,5-均三嗪三醇的应用研究.E-mail:mengli0621@163.com
  • 基金资助:
    山东省重点研发计划资助项目(2017CXGC1008)

Catalytic amination of sym-triazinetriol with diethylenetriamine

MENG Li1, WANG Qian2, CHAI Shu1, ZHU Wei-qun1*   

  1. 1. School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, Shandong, China;
    2. Institute of National Engineering Research Center for Colloidal Materials, Shandong University, Jinan 250100, Shandong, China
  • Received:2017-07-31 Online:2018-03-20 Published:2018-03-13

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摘要： CO2作为一种碳资源,对其进行化学利用以达到减排目的,已成为目前科学研究热点之一。1,3,5-均三嗪三醇是一种CO2封存产品,开发其下游产品具有广阔前景。以1,3,5-均三嗪三醇(sym-triazinetriol, CA)与二乙烯三胺(diethylenetriamine, DETA)为原料,合成6-二乙烯三胺基-1,3,5-三嗪-2,4(1H,3H)-二酮。采用单因素法探讨了反应物摩尔比、反应时间、反应温度以及催化剂对产率的影响,由FT-IR、1H NMR与13C NMR等表征产物。反应最佳条件:CA与DETA摩尔比为1∶4,反应温度210 ℃,反应时间为4 h,催化剂为5A分子筛,产率为70.9%。

关键词: 固碳产品, 1,3,5-均三嗪三醇, 二乙烯三胺, 合成

Abstract: As a carbon resource, it has become one of the hot spots at present through the chemical utilization of CO2 to achieve emission reduction purposes. Sym-triazinetriol is kind of CO2 sequestration products, and it has broad prospects to develop its downstream products. In this paper, synthesis of 6-divinyl three amine-1,3,5-triazine base-2,4(1H,3H)-diketone by diethylenetriamine(DETA)and Sym-triazinetriol(CA)was studied. The effects of molar ratio, reaction time, reaction temperature and catalyst on the yields were investigated by single-factor method. Then, the product was characterized by IR, 1H NMR and 13C NMR. The optimum conditions were as follows: the molar ratio of CA to DETA was 1∶4, the reaction temperature was 210 ℃, the reaction time was 4 h, the catalyst was 5A molecular sieve. The yield of product can reach 70.9%.

Key words: sym-triazinetriol, diethylenetriamine, synthesis, carbon sequestration product

中图分类号: 

  • TQ9
[1] 曹宏源. 国际能源署: 去年全球二氧化碳排放量未增加[N]. 中国电力报, 2015-03-20(002). CAO Hongyuan. IEA: Global carbon dioxide emissions didnt increase Last year[N]. China Electric Power News, 2015-03-20(002).
[2] COMPSTON H, BAILEY I. Climate policy strength compared: China, the US, the EU, India, Russia, and Japan[J]. Climate Policy, 2016, 16(2):145-164.
[3] PEARSON P N, FOSTER G L, WADE B S. Atmospheric carbon dioxide through the eocene-oligocene climate transition[J]. Nature, 2009, 461(7267): 1110-1113.
[4] OCHIAI B, ENDO T. Carbon dioxide and carbon disulfide as resources for functional polymers[J]. Progress in Polymer Science, 2005, 30(2): 183-215.
[5] PRENTICE I C, FARQUHAR G D, FASHAM M J R, et al. The carbon cycle and atmospheric carbon dioxide[J]. Cambridge University Press, 2001, 41(3): 159-165.
[6] 朱维群, 齐情情, 王倩, 等. 化石燃料环境友好工业路线开发[J]. 山东大学学报(理学版), 2017, 52(5): 25-30. ZHU Weiqun, QI Qingqing, WANG Qian, et al. The development of fossil fuel environment-friendly industrial route[J]. Journal of Shandong University(Natural Science), 2017, 52(5):25-30.
[7] 王付燕, 孙洪志, 宋名秀, 等.二氧化碳的氨化反应研究进展[J]. 化工进展, 2014, 33(1): 209-218. WANG Fuyan, SUN Hongzhi, SONG Mingxiu, et al. Research progress of ammonization reaction of carbon dioxide[J]. Journal of Chemical Industry and Engineering Progress, 2014, 33(1): 209-218.
[8] 宋名秀, 孙洪志, 阿布都拉江·那斯尔, 等.二氧化碳减排技术路线探讨[J]. 现代化工, 2013, 33(8): 5-8. SONG Mingxiu, SUN Hongzhi, Abudoulajiang·Nasier, et al. Discussion on carbon dioxide emission reduction technologies[J]. Journal of Modern Chemical Industry, 2013, 33(8): 5-8.
[9] 朱维群, 王倩, 阿不都拉江·那斯尔, 等. 利用氨气和二氧化碳合成三聚氰酸或三聚氰胺的方法: CN102633736A[P]. 2012-08-15. ZHU Weiqun, WANG Qian, Abudoulajiang·Nasier, et al. Process for synthesizing cyanuric acid or melamine by using ammonia gas and carbon dioxide: CN102633736A[P]. 2012-08-15.
[10] 罗胜铁, 孟丽军. 氯代异氰脲酸类产品的制备和应用[J]. 化工进展, 2002, 21(9): 693-696. LUO Shengtie, MENG Lijun. Preparation and application of isocyanuric acid chloride products[J]. Journal of Chemical Industry and Engineering Progress, 2002, 21(9): 693-696.
[11] KLUGE R, SCHULZ M, LIEBSCH S. Diastereoselective epoxidation of olefins by organo sulfonic peracids, II[J]. Tetrahedron, 1996, 52(8): 2957-2976.
[12] ERMAKOV A S, BULATOV P V, VINOGRADOV D B, et al. Synthesis of nitroesters based on methylol derivatives of parabanic and isocyanuric acids[J]. Russian Journal of Organic Chemistry, 2005, 41(2): 255-256.
[13] 彭敏, 单文伟, 曾光明,等. 三(环氧丙基)异氰尿酸酯的合成[J]. 热固性树脂, 2004, 19(6): 12-14. PENG Min, SHAN Wenwei, ZENG Guangming, et al. Synthesis of triglycidyl isocyanurate[J]. Thermosetting Resin, 2004, 19(6): 12-14.
[14] 朱维群. 一种低温合成三聚氰胺的新方法[C] //全国化工合成氨设计技术中心站2011年技术交流会论文集. 长沙:全国化工合成氨设计技术中心站2011年技术交流会. 2011. ZHU Weiqun. A new method for synthesis of melamine at low temperature[C] //Proceedings of National Chemical Ammonia Synthesis Design Technology Center Station 2011 Technical Exchange Meeting. Changsha:National Chemical Ammonia Synthesis Design Technology Center Station 2011 Technical Exchange Meeting. 2011.
[15] 林休休,刘小红,徐冬梅,等. 一种含三嗪环的四臂引发核的合成与表征[J]. 精细化工,2007, 24(2): 194-198. LIN Xiuxiu, LIU Xiaohong, XU Dongmei, et al. Synthesis and characterization of a four-arm initiating core containing 1,3,5-triazine[J]. Fine Chemicals, 2007, 24(2):194-198.
[16] 杨贵宝. 三聚氯氰与脂肪族多胺的反应研究及树枝状多臂引发核的制备[D]. 苏州: 苏州大学, 2009. YANG Guibao. Study on the reaction between aliphatic polyamines and cyanuric chloride and synthesis of multi-arm dendritic initial cores[D]. Suzhou: Soochow University, 2009.
[17] 王婉秦, 张秀成, 陈立宇, 等. 氨化法合成 3,5-二甲基苯胺的工艺研究[J]. 染料与染色,2001, 38(3): 35-36. WANG Wanqin, ZHANG Xiucheng, CHEN Liyu, et al. A study on the synthesis of 3,5-dimethylaniline by amination[J]. Dyestuff Industry, 2001, 38(3): 35-36.
[18] 文明. 高活性负载金属镍催化剂上醇的催化胺化研究[D]. 南京: 南京大学, 2016. WEN Ming. A study of amination of alcohols to amines over supported nickel cahlysts[D]. Nanjing: Nanjing University, 2016.
[19] MANOHAR B, GANESH I, REDDY B M. Aniline synthesis from cyclohexanol and ammonia over mixed oxide catalysts[J]. Journal of Molecular Catalysis A Chemical,1998, 129(1):L5-L8.
[20] 封超, 陈立宇, 应晓有, 等. 2,6-二甲基苯酚在超临界氨中的催化氨化工艺研究[J]. 高校化学工程学报,2012, 26(6): 977-982. FENG Chao, CHEN Liyu, YING Xiaoyou, et al. Catalytic amination of 2,6-dimethylphenol in supercritical ammonia[J]. Journal of Chemical Engineering of Chinese Universities, 2012, 26(6): 977-982.
[21] 钱超. 醇羟基及酚羟基化合物的催化胺化[D].杭州: 浙江大学, 2004. QIAN Chao. Study on catalytic amination of alcohols and phenols[D]. Hangzhou: Zhejiang University, 2016.
[22] LIAO Y W, ZHOU Q J, CHEN M J, et al. Standard test methods of amine value and preliminary investigation of spraying pure polyurea used in beijing-shanghai high-speed railway[J]. Shanghai Coatings, 2010, 48(5): 38-40.
[23] 孙曼灵, 郑高锋. 胺类环氧固化剂胺值测定方法的探讨[J]. 热固性树脂,2006, 21(2): 30-32. SUN Manling, ZHENG Gaofeng. Study on measurement method of amine value of amine epoxy hardener[J]. Thermosetting Resin, 2006, 21(2): 30-32.
[24] 余秦伟, 李亚妮, 梅苏宁, 等. 改性HZSM-5催化胺化异丙醇胺合成1,2-丙二胺[J]. 化工进展,2014, 33(8): 2060-2065. YU Qinwei, LI Yani, MEI Suning, et al. Synthesis of 1,2-propanediamine by amination of isopropanolamine on modified HZSM-5[J]. Journal of Chemical Industry and Engineering Progress, 2014, 33(8): 2060-2065.
[25] 化工百科全书编委会. 化工百科全书[M].北京: 化学工业出版社, 1990: 150. Encyclopedia of chemical technology editorial society. Encyclopedia of chemical technology[M].Beijing:Chemical Industry Press, 1990: 150.
[26] KEN Motokura, NOBUAKI Nakagiri, TOMOO Mizugaki, et al. Nucleophilic substitution reactions of alcohols with use of montmorillonite catalysts as solid brønsted acids[J]. Journal of Organic Chemistry, 2007, 72(16):6006-6015.
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