Citation: LI Yuhan, WU Qiang, KANG Chuanqing, GUO Haiquan, JIN Rizhe, GAO Lianxun. Synthesis of 2,3,3',4'-Biphenyltetracarboxylic Dianhydride[J]. Chinese Journal of Applied Chemistry, ;2016, 33(8): 900-904. doi: 10.11944/j.issn.1000-0518.2016.08.150401 shu

Synthesis of 2,3,3',4'-Biphenyltetracarboxylic Dianhydride

  • Corresponding author: JIN Rizhe, 
  • Received Date: 16 November 2015
    Available Online: 2 March 2016

    Fund Project:

  • A facile synthesis of 2,3,3',4'-biphenyltetracarboxylic dianhydride through cross-coupling of halo-substituted orthoxylene and liquid-phase oxidation of the resulted tetramethylbiphenyl. 2,3,3',4'-Tetramethylbiphenyl(3,4'-TMDP) was synthesized by cross-coupling of 4-bromo-1,2-dimethylbenzene and 3,4-dimethylphenylmagnesium bromide with NiF2-PPh3(PPh3:triphenylphosphine) as the catalyst and which was then converted to 2,3,3',4'-biphenyltetracarboxylic dianhydride(3,4'-BPDA) by the oxidation and dehydration procedures. The overall yield reached to 74%. In comparison with the preparations of 3,4'-BPDA from dimethyl phthalate or chlorinated dimethyl phthalate mixture, the method exhibits advantages in the separation and environmental benign because of the avoidance of the tedious hydrolysis step and the separation of isomers.
  • 加载中
    1. [1]

      [1] DING Mengxian. Polyimide-Relationship of Chemistry, Structure and Properties and Thier Matiaral[M]. Beijing:Science Press,2006:590-646(in Chinese).丁孟贤. 聚酰亚胺—化学、结构与性能关系及材料[M]. 北京:科学出版社,2006:590-646.

    2. [2]

      [2] Dine Hart R A,Wright W W. Preparation and Fabrication of Aromatic Polyimides[J]. J Appl Polym Sci,1967,11(5):609-627.

    3. [3]

      [3] Boyd J,James P. Partially Fluorinated Polyimide Resins and Composites[M]//Nicolas L,Borzacchiello A. Wiley Encyclopedia of Composites. Hoboken:John Wiley & Sons Lmt,2012:1-30.

    4. [4]

      [4] Imai Y. Recent Advances in Synthesis of High-Temperature Aromatic Polymers[J]. React Funct Polym,1996,30(1):3-15.

    5. [5]

      [5] Zhang M,Wang Z,Gao L X,et al. Polyimides from Isomeric Diphenylthioether Dianhydrides[J]. J Polm Sci Polym Chem,2006,44(2): 959-967.

    6. [6]

      [6] Smith J J G,Connell J W,Hergenrother P. M,et al. Transfer Molding Imide Resins Based on 2,3,3',4'-Biphenyltetracarboxylic Dianhydride[J]. Macromol Symp,2003,199(1):401-418.

    7. [7]

      [7] Ding M X. Isomeric Polyimides[J]. Prog Polym Sci,2007,32(6):623-668.

    8. [8]

      [8] Hasegawa M,Sensui N,Shindo Y,et al. Structure and Properties of Novel Asymmetric Biphenyl Type Polyimides. Homo- and Copolymers and Blends[J]. Macromolecules,1999,32(2):387-396.

    9. [9]

      [9] Kochi M,Chen C H,Youota R,et al. Isomeric Biphenyl Polyimides.(Ⅱ)Glass Transitions and Secandary Relaxation Processes[J]. High Perf Polym,2005,17(3):335-347.

    10. [10]

      [10] Fang X Z,Wang Z,Yang Z H,et al. Novel Polyimides Derived from 2,3,3',4'-Benzophenonetetracarboxylic Dianhydride[J]. Polymer,2003,44(9):2641-2646.

    11. [11]

      [11] Wang H Y,Zhu D M,Zhou W C,et al. Effect of Multiwalled Carbon Nanotubes on the Electromagnetic Interference Shielding Properties of Polyimide/Carbonyl Iron Composites[J]. Ind Eng Chem Res,2015,54(25):6589-6595.

    12. [12]

      [12] Pan L Y,Zhan M S,Wang K. Preparation and Characterization of High-TemperatureResistance Polyimide Foams[J]. Polym Eng Sci,2010,50(6):1261-1267.

    13. [13]

      [13] Itanani H,Kashimoto M,Yoshimoto H. Progress for Producing Biphebyltetacarboxylic Dianhydrides:US,3940426[P],1976.

    14. [14]

      [14] Itanani H,Yoshimoto H. Palladium-Catalyzed Syntheses of Aromatic Coupling Compounds[J]. J Org Chem,1973,38(1):76-79.

    15. [15]

      [15] WANG Zhen,WU Xue'e,GAO Changlu,et al. Synthetic Method of 2,3,3',4'-Biphenyltetracarboxylic Dianhydride and Its Derivetives:CN,03105026.3[P],2003-03-03(in Chinese).王震,吴雪娥,高昌录,等. 2,3,3',4'-联苯四甲酸二酐及其衍生物的制备方法:中国,03105026.3[P],2003-03-03.

    16. [16]

      [16] GUO Haiquan,YAO Haibo,QIU Xuepeng,et al. A Synthetic Method of Biphenyltetracarboxylic Dianhydride:CN,201110202366.3[P],2011-07-19(in Chinese).郭海泉,姚海波,邱雪鹏,等. 一种联苯二酐的制备方法:中国,201110202366.3[P],2011-07-19.

    17. [17]

      [17] Fagnou K,Lautens M. Halide Effects in Transition Metal Catalysis[J]. Angew Chem Int Ed,2002,41(1):26-47.

  • 加载中
    1. [1]

      Lifang HEWenjie TANGYaoze LUOMingsheng LIANGJianxin TANGYuxuan WUFuxing ZHANGXiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012

    2. [2]

      Yuting BaiCenqi YanZhen LiJiaqiang QinPei Cheng . Preparation of High-Strength Polyimide Porous Films with Thermally Closed Pore Property by In Situ Pore Formation Method. Acta Physico-Chimica Sinica, 2024, 40(9): 2306010-0. doi: 10.3866/PKU.WHXB202306010

    3. [3]

      Feng Zheng Ruxun Yuan Xiaogang Wang . “Research-Oriented” Comprehensive Experimental Design in Polymer Chemistry: the Case of Polyimide Aerogels. University Chemistry, 2024, 39(10): 210-218. doi: 10.12461/PKU.DXHX202404027

    4. [4]

      Chunling QinShuang ChenHassanien GomaaMohamed A. ShenashenSherif A. El-SaftyQian LiuCuihua AnXijun LiuQibo DengNing Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059

    5. [5]

      Lixing ZHANGYaowen WANGXu HANJunhong ZHOUJinghui WANGLiping LIGuangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007

    6. [6]

      Jing WUPuzhen HUIHuilin ZHENGPingchuan YUANChunfei WANGHui WANGXiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278

    7. [7]

      Ying Chen Ronghua Yan Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066

    8. [8]

      Xinting XIONGZhiqiang XIONGPanlei XIAOXuliang NIEXiuying SONGXiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145

    9. [9]

      Bin SUNHeyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428

    10. [10]

      Jiaming Xu Yu Xiang Weisheng Lin Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093

    11. [11]

      Xinyi ZhangKai RenYanning LiuZhenyi GuZhixiong HuangShuohang ZhengXiaotong WangJinzhi GuoIgor V. ZatovskyJunming CaoXinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057

    12. [12]

      Lei FengZe-Min ZhuYing YangZongbin HeJiafeng ZouMan-Bo LiYan ZhaoZhikun Wu . Long-Pursued Structure of Au23(S-Adm)16 and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029

    13. [13]

      Wenjuan SHIYuke LUXiuyuan LILei HOUYaoyu WANG . Mg(Ⅱ) metal-organic frameworks based on biphenyltetracarboxylic acid: Synthesis and CO2 adsorption and catalytic conversion performance. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2455-2463. doi: 10.11862/CJIC.20250220

    14. [14]

      Lirui Shen Kun Liu Ying Yang Dongwan Li Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035

    15. [15]

      Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065

    16. [16]

      Lili Jiang Shaoyu Zheng Xuejiao Liu Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004

    17. [17]

      Qilu DULi ZHAOPeng NIEBo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006

    18. [18]

      Jichao XUMing HUXichang CHENChunhui WANGLeichen WANGLingyi ZHOUXing HEXiamin CHENGSu JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144

    19. [19]

      Ling Liu Haibin Wang Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080

    20. [20]

      Zhiwen HUWeixia DONGQifu BAOPing LI . Low-temperature synthesis of tetragonal BaTiO3 for piezocatalysis. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 857-866. doi: 10.11862/CJIC.20230462

Metrics
  • PDF Downloads(0)
  • Abstract views(645)
  • HTML views(136)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return