JOURNAL OF SHANDONG UNIVERSITY(NATURAL SCIENCE) ›› 2018, Vol. 53 ›› Issue (3): 88-94.doi: 10.6040/j.issn.1671-9352.0.2017.377

Previous Articles    

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

PDF (PC)

621

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

CLC Number: 

  • 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.
[1] LI Jia-qi, DENG Yu-zhou, LIU Gang, YUE Ren-liang, YANG Jun, CHEN Yun-fa. The application of flame combustion synthesis in the preparation of metal oxide and supported noble metal catalysts [J]. JOURNAL OF SHANDONG UNIVERSITY(NATURAL SCIENCE), 2016, 51(1): 1-13.
[2] ZHANG Yao-jun, WAN Gang-qiang, YAN Lei, MA Qing-chang, LI Dong-xiang, ZHAO Ji-kuan. Assembled nanostructures of ZnO nanorods prepared by seed growth method [J]. JOURNAL OF SHANDONG UNIVERSITY(NATURAL SCIENCE), 2016, 51(1): 14-19.
[3] CHEN Lei, JIN Zhi, LIU Qiang, WANG Ming, WANG Pu*. Novel synthesis of C-terminal polypeptides by ISPPS method [J]. JOURNAL OF SHANDONG UNIVERSITY(NATURAL SCIENCE), 2014, 49(1): 31-35.
[4] SHI Kai-quan. P-information law intelligent fusion and soft information #br# image intelligent generation [J]. JOURNAL OF SHANDONG UNIVERSITY(NATURAL SCIENCE), 2014, 49(04): 1-17.
[5] HAN Lu1, SHENG Dao-peng1, WEI Hui-ying1, YANG Yan-zhao1,2 *. Synthesis and characterization of a novel coordination complex ［Ni(Hpdc)(2,2’-bipy)(H2O)2］·H2O [J]. J4, 2012, 47(5): 9-12.
[6] JIN Zhi, HU Nai-feng, LIU Qiang, WANG Pu*. Application of TbfmocMetOH for solid phase synthesis of ubiquitin [J]. J4, 2011, 46(7): 21-25.
[7] REN Hui-xue1,2, YING Han-jie2, LIU Chang1, JIA Xiang-feng1, YANG Yan-zhao3. Study on the synthesis of Cefuroxime acid with a new phosphoryl active ester [J]. J4, 2011, 46(3): 9-12.
[8] CHENG Dan-Dan, XU Chun-Hua, YIN Zhi-Lei, YUE Qin-Yan, WANG Yan. Removal of Cr (VI) from aqueous solutions by nano β-FeOOH [J]. J4, 2010, 45(1): 31-35.
[9] SUN Yan-lin,ZHOU Chuan-jian* and ZHAO Shi-gui . Systhesis of mesoporous organosilicas using a new kind of carbosilane dendrimers as a silica resource [J]. J4, 2007, 42(5): 38-43 .
[10] XU Fei,GUO Wei-hua,WANG Yu-fang,WANG Wei,DU Ning and WANG Ren-qing* . Photosynthetic fluorescence characteristics of six greening tree species on university campuses in the city of Jinan [J]. J4, 2007, 42(5): 86-94 .
[11] ZHANG Ke-wei,WANG Xian-li,LI Kun-peng and ZHANG Ju-ren . Effect of low-level phosphorus stress on photosynthetic characteristics of maize inbred line seedlings with low-level phosphorus tolerance [J]. J4, 2007, 42(3): 89-94 .
[12] QU Wen,SU Ji-xin*,PAN Qi,NIE Yu-lun . Synthesis and acid catalytic activity of HSO3-functionalized silica [J]. J4, 2007, 42(11): 11-14 .
Viewed
Full text


Abstract

Cited
  Shared   
  Discussed   
No Suggested Reading articles found!
Copyright 2018 © Editorial office of JOURNAL OF SHANDONG UNIVERSITY(NATURAL SCIENCE)
Supported by Beijing Magtech Co.Ltd