Citation: YU Wei-Feng, MENG Xiang-Guang, LIU Ying, LI Xiao-Hong. Selective Oxidation of 4-Methoxymandelic Acid Catalyzed by Mononucleonic and Binucleonic Metal Complexes[J]. Acta Physico-Chimica Sinica, ;2013, 29(09): 2041-2046. doi: 10.3866/PKU.WHXB201306282 shu

Selective Oxidation of 4-Methoxymandelic Acid Catalyzed by Mononucleonic and Binucleonic Metal Complexes

1.
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China

Received Date: 26 April 2013
Available Online: 28 June 2013
Fund Project: 国家自然科学基金(21073126, 21273156)资助项目 (21073126, 21273156)

Three kinds of mononucleonic metal complexes of L¹Cu, L¹Co, and L¹Mn (L¹=N,N'-bis-(2-hydroxyethyl)-malondiamide), and three kinds of binucleonic metal complexes of L²Cu, L²Co, and L²Mn (L²= N,N'-bis{2-(2-hydroxyethylamino)ethyl}-malondiamide) were prepared. These complexes exhibited od catalytic performance for the selective oxidation of 4-methoxymandelic acid (4-MMA) by H₂O₂ in buffer solution, with >96% selectivity to anisaldehyde (AAD) and a small percentage to 4-methoxybenzoic acid (4-MBA). However, the reaction rates were quite different for these catalytic systems, in which the copper complex was the best candidate as the catalyst for the oxidation of 4-MMA. The binucleonic complexes displayed obviously better catalytic performance than the mononucleonic complexes. The effect of the applied buffers (tartaric acid (TA), H₃O₄, HAc) on the catalytic performance in terms of activities and selectivities for the oxidation of 4-MMA by H₂O₂ were investigated. The reaction kinetics of 4-MMA oxidation catalyzed by six complexes was studied in detail. The apparent first-order rate constants (k_obs) were obtained in the pH range of 2.5 to 4.5. The pHeffect on the catalytic oxidation was discussed in this paper.
- 4-Methoxymandelic acid,
- Metal complex,
- Selective oxidation,
- Decarboxylation,
- Lignin
1. [1]
  
  (1) Chen, C. L.; Capanema, E. A.; Gracz, H. S. J. Agric. Food Chem. 2003, 51, 6223. doi: 10.1021/jf034507f
2. [2]
  (2) Cotrim, A. R.; Ferraz, A.; nqalves, A. R.; Silva, F. T.; Bruns,R. E. Bioresource Technol. 1999, 68, 29. doi: 10.1016/S0960-8524(98)00082-0
3. [3]
  (3) Santos, R. B.; Capanema, E. A.; Balakshin, M. Y.; Chang, H.;Jameel, H. J. Agric. Food Chem. 2012, 60, 4923. doi: 10.1021/jf301276a
4. [4]
  (4) Sarkanen, K. V.; Hergert, H. L. Lignins: Occurrence, Formation, Structure and Reactions; Sarkanen, K. V., Ludwig,C. H. Eds.; Wiley-Interscience: NewYork, 1971; p 43.
5. [5]
  (5) Kobayashi, H.; Ohta, H.; Fukuoka, A. Catal. Sci. Technol. 2012,2, 869. doi: 10.1039/c2cy00500j
6. [6]
  (6) Sathitsuksanoh, N.; George, A.; Zhang, Y. H. P. J. Chem. Technol. Biotechnol. 2013, 88, 169. doi: 10.1002/jctb.2013.88.issue-2
7. [7]
  (7) Yuan, T. Q.; Xu, F.; Sun, R. C. J. Chem. Technol. Biotechnol.2013, 88, 346. doi: 10.1002/jctb.2013.88.issue-3
8. [8]
  (8) Have, R. T.; Teunissen, P. J. M. Chem. Rev. 2001, 101, 3397.doi: 10.1021/cr000115l
9. [9]
  (9) Renganathan, V.; ld, M. H. Biochemistry 1986, 25, 1626. doi: 10.1021/bi00355a027
10. [10]
  (10) Collins, P. J.; Kotterman, M. J. J.; Field, J. A.; Dobson, A. D. W.Appl. Environ. Microbiol. 1996, 62, 4563.
11. [11]
  (11) Tien, M.; Kirk, T. K. Science 1983, 221, 661.
12. [12]
  (12) Barsberg, S.; Elder, T.; Felby, C. Chem. Mater. 2003, 15, 649.doi: 10.1021/cm021162s
13. [13]
  (13) Tien, M.; Ma, D. J. Biol. Chem. 1997, 272, 8912. doi: 10.1074/jbc.272.14.8912
14. [14]
  (14) Baciocchi, E.; Gerini, M. F.; Lanzalunga, O.; Mancinelli, S.Tetrahedron 2002, 58, 8087. doi: 10.1016/S0040-4020(02)00997-3
15. [15]
  (15) Brown, M. E.; Barros, T.; Chang, M. C. Y. ACS Chem. Biol.2012, 7, 2074. doi: 10.1021/cb300383y
16. [16]
  (16) Ferapontova, E. E.; Castillo, J.; rton, L. BBA.-Gen. Subjects2006, 1760, 1343. doi: 10.1016/j.bbagen.2006.04.003
17. [17]
  (17) Favier, I.; Dunach, E. Tetrahedron 2003, 59, 1823. doi: 10.1016/S0040-4020(03)00083-8
18. [18]
  (18) Zeng, W. P.; Li, X. H.; Du, J.; Li, J. M.; Zhang, P.; Hu, C. W.;Meng, X. G. Acta Chim. Sin. 2010, 68, 27. [曾伟鹏, 李小红,杜娟,李建梅,张平,胡常伟,孟祥光.化学学报, 2010, 68,27.]
19. [19]
  (19) Liu, B.; Meng, X. G.; Li, W. Y.; Zhou, L. C.; Hu, C. W. J. Phys. Chem. A 2012, 116, 2920. doi: 10.1021/jp212489k
20. [20]
  (20) Toki, T.; Mikuriya, M.; Okawa, H.; Murase, I.; Kida, S. Bull. Chem. Soc. Jpn. 1984, 57, 2098.
21. [21]
  (21) Hill, H. A. O.; Raspin, K. A. J. Chem. Soc. A 1968, 3036.
22. [22]
  (22) Feng, M. F.; Hu, W.; Jiang, W. D.; Xie, J. Q. Journal of Sichuan University of Science& Engineering 2004, 17, 140. [冯发美,胡伟,蒋维东,谢家庆.四川理工学院学报, 2004, 17, 140.]
23. [23]
  (23) Li, J. M.; Meng, X. G.; Hu, C. W.; Du, J.; Zeng, X. C. J. Mol. Catal. A: Chem. 2009, 299, 102. doi: 10.1016/j.molcata.2008.10.026
24. [24]
  (24) Lin, T. Y.; Wu, C. H. J. Catal. 2005, 232, 117. doi: 10.1016/j.jcat.2005.01.038
25. [25]
  (25) Kadiiska, M. B.; Maples, K. R.; Mason, R. P. Arch. Biochem. Biophys. 1989, 275, 98. doi: 10.1016/0003-9861(89)90354-8
26. [26]
  (26) Frelon, S.; Douki, T.; Favier, A.; Cadet, J. Chem. Res. Toxicol.2003, 16, 191. doi: 10.1021/tx025650q
1. [1]
  Hong Wu , Yuxi Wang , Hongyan Feng , Xiaokui Wang , Bangkun Jin , Xuan Lei , Qianghua Wu , Hongchun Li . Application of Computational Chemistry in the Determination of Magnetic Susceptibility of Metal Complexes. University Chemistry, 2025, 40(3): 116-123. doi: 10.12461/PKU.DXHX202405141
2. [2]
  Jiali Lei , Juan Wang , Wenhui Zhang , Guohong Wang , Zihui Liang , Jinmao Li . TiO₂/CdIn₂S₄ S-scheme heterojunction photocatalyst promotes photocatalytic hydrogen evolution coupled vanillyl alcohol oxidation. Acta Physico-Chimica Sinica, 2025, 41(12): 100174-0. doi: 10.1016/j.actphy.2025.100174
3. [3]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
4. [4]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
5. [5]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
6. [6]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
7. [7]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
8. [8]
  Qishen Wang , Changzhao Chen , Mengqing Li , Lingmin Wu , Kai Dai . Lignin derived carbon quantum dots and oxygen vacancies coregulated S-scheme LCQDs/Bi₂WO₆ heterojunction for photocatalytic H₂O₂ production. Acta Physico-Chimica Sinica, 2025, 41(11): 100147-0. doi: 10.1016/j.actphy.2025.100147
9. [9]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
10. [10]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
11. [11]
  Zhi Chai , Huashan Huang , Xukai Shi , Yujing Lan , Zhentao Yuan , Hong Yan . Wittig反应的立体选择性. University Chemistry, 2025, 40(8): 192-201. doi: 10.12461/PKU.DXHX202410046
12. [12]
  Jing Zhang , Su Zhang , Qiqi Li , Linken Ji , Yutong Li , Yukang Ren , Xiaobei Zang , Ning Cao , Han Hu , Peng Liang , Zhuangjun Fan . Integrating high surface area and electric conductivity in activated carbon by in situ formation of the less-defective carbon network during selective chemical etching. Acta Physico-Chimica Sinica, 2025, 41(10): 100114-0. doi: 10.1016/j.actphy.2025.100114
13. [13]
  .
  CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
  . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.
14. [14]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
15. [15]
  Xinyu Xu , Jiale Lu , Bo Su , Jiayi Chen , Xiong Chen , Sibo Wang . Steering charge dynamics and surface reactivity for photocatalytic selective methane oxidation to ethane over Au/Ti-CeO₂. Acta Physico-Chimica Sinica, 2025, 41(11): 100153-0. doi: 10.1016/j.actphy.2025.100153
16. [16]
  Ji Qi , Jianan Zhu , Yanxu Zhang , Jiahao Yang , Chunting Zhang . Visible Color Change of Copper (II) Complexes in Reversible SCSC Transformation: The Effect of Structure on Color. University Chemistry, 2024, 39(3): 43-57. doi: 10.3866/PKU.DXHX202307050
17. [17]
  Lijun Yue , Siya Liu , Peng Liu . 不同晶相纳米MnO₂的制备及其对生物乙醇选择性氧化催化性能的测试——一个科研转化的综合化学实验. University Chemistry, 2025, 40(8): 225-232. doi: 10.12461/PKU.DXHX202410005
18. [18]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
19. [19]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
20. [20]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017

Get Citation

PDF

XML

Metrics

PDF Downloads(483)
Abstract views(909)
HTML views(21)

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