Citation: YE Yong-Wei, WANG Xi, ZHENG Wan-Fang, LI Mei-Chao, MA Chun-An. Electrooxidation Reaction of 3-Bromobenzoic Acid on Pt Electrode[J]. Acta Physico-Chimica Sinica, ;2013, 29(03): 553-558. doi: 10.3866/PKU.WHXB201301101 shu

Electrooxidation Reaction of 3-Bromobenzoic Acid on Pt Electrode

1.
Research Center of Analysis and Measurement, College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310032, P. R. China

Received Date: 30 October 2012
Available Online: 10 January 2013
Fund Project: 国家重点基础研究发展计划(973)项目(2012CB722604) (973)项目(2012CB722604)国家自然科学基金(21206147)资助 (21206147)

Electrochemical oxidation of 3-bromobenzoic acid (3-BBA) on a Pt electrode in alkali solution was studied by cyclic voltammetry and in situ Fourier transform infrared (FTIR) spectroscopy. The Pt electrode exhibited od performance for the electrooxidation of 3-BBA. At low oxidation potential (1000 mV), one electron was removed from the 3-BBA radical anion and the corresponding free radical was generated. A Bbromobenzene free radical cation and carbon dioxide were obtained after decarboxylation. The bromobenzene cation was then attacked by the hydroxyl radical, which was adsorbed on the anode, and the bromobenzene cation intermediate product was debrominated to form phenol. When the potential shifted to more positive values, phenol was electrooxided to produce dihydroxybenzene and benzoquinone. Maleic acid and fumaric acid were also detected as the reaction products of the ring-opening reaction.
- 3-Bromobenzoic acid,
- In situ Fourier transform infrared spectroscopy,
- Electrooxidation,
- Decarboxylation reaction,
- Debromination reaction
1. [1]
  
  (1) Scialdone, O.; Guarisco, C.; Galia, A.; Lo, C. C.; Bunce, N. J.;Konstantinov, A. D. J. Electroanal. Chem. 2010, 641, 14.doi: 10.1016/j.jelechem.2010.01.018
2. [2]
  (2) Ma, C. A.; Li, M. C.; Liu, Y. N.; Xu, Y. H. Electrochim. Acta2010, 55, 3171. doi: 10.1016/j.electacta.2009.12.086
3. [3]
  (3) Konstantinov, A.; Bejan, D.; Bunce, N.; Chittim, B.; McCrindle,R.; Potter, D.; Tashiro, C. J. Chemosphere 2008, 72, 1159.doi: 10.1016/j.chemosphere.2008.03.046
4. [4]
  (4) Pera-Titus, M.; García-Molina, V.; Baños, M. A.; Giménez, J.;Esplugas, S. Appl. Catal. B: Environ. 2004, 47 (4), 219. doi: 10.1016/j.apcatb.2003.09.010
5. [5]
  (5) Chen, G.;Wang, Z. Y.; Xia, D. G. Electrochem. Commun. 2004,6, 268. doi: 10.1016/j.elecom.2003.12.011
6. [6]
  (6) Benedict, R. T.; Stapleton, H. M.; Letcher, R. J.; Mitchelmore,C. I. Chemosphere 2007, 69 (6), 987. doi: 10.1016/j.chemosphere.2007.05.010
7. [7]
  (7) Zhu, Y. H.; Xu, Y. H.; Ma, H.; Zhao, F. M.; Ma, C. A. ActaPhys. -Chim. Sin. 2009, 25 (6), 1190. [朱英红, 徐颖华,马昊, 赵峰鸣, 马淳安. 物理化学学报, 2009, 25 (6), 1190.]doi: 10.3866/PKU.WHXB20090625
8. [8]
  (8) Zheng, L.; Zhu, C. Z.; Xu, Y.; Lu, X.; Hou, H. Q. Resarch ofEnvironmental Sciences 2004, 17 (6), 54. [郑璐, 朱承驻,徐莺, 卢霄, 侯惠奇. 环境科学研究, 2004, 17 (6), 54.]
9. [9]
  (9) Wang, Y. L.; Cai, N. C.; Huo, Y. D.; Chen, H. Acta Phys. -Chim.Sin. 2001, 17 (7), 609. [王玉玲, 蔡乃才, 霍耀东, 陈浩. 物理化学学报, 2001, 17 (7), 609.] doi: 10.3866/PKU.WHXB20010707
10. [10]
  (10) Fang, L.; Huang, J.; Yu, G.;Wang, L. N. Chemosphere 2008, 71,258. doi: 10.1016/j.chemosphere.2007.09.041
11. [11]
  (11) Sun, S. G.; ng, H. Petrochemical Technology 2001, 30, 806.[孙世刚, 贡辉. 石油化工, 2001, 30, 806.]
12. [12]
  (12) Zhang, X. X.; Zhang, Y. X.; Jiang, J. Z. J. Mol. Struct. 2004,673, 103.
13. [13]
  (13) Miki, A.; Ye, S.; Senzaki, T.; Osawa, M. J. Electroanal. Chem.2004, 563, 23. doi: 10.1016/j.jelechem.2003.09.014
14. [14]
  (14) Trettenhahn, G.; Köberl, A. Electrochim. Acta 2007, 52, 2716.doi: 10.1016/j.electacta.2006.09.028
15. [15]
  (15) Su, K. M.; Pan, T. Y.; Zhang, Y. L. Spectrum Analysis Method;East China University of Science and Technology Press:Shanghai, 2002; pp 106-107. [苏克曼, 潘铁英, 张玉兰. 波谱解析法. 上海: 华东理工大学出版社, 2002: 106-107.]
16. [16]
  (16) Li, M. C.; Bao, D. D.; Ma, C. A. Electrochim. Acta 2011, 56,4100. doi: 10.1016/j.electacta.2011.01.115
17. [17]
  (17) Sundaraganesan, N.; Meganathan, C.; Karthikeyan, B.Spectrochim. Acta A 2008, 70, 430. doi: 10.1016/j.saa.2007.12.022
18. [18]
  (18) Chetty, R.; Christensen, P. A.; lding, B. T.; Scott, K. Appl.Catal. A: Gen. 2004, 271, 185. doi: 10.1016/j.apcata.2004.02.059
19. [19]
  (19) Zhou, M. H.;Wu, Z. C.;Wang, D. H. Chem. J. Chin. Univ.2003, 24 (9), 1637. [周明华, 吴祖成, 汪大翚. 高等学校化学学报, 2003, 24 (9), 1637.]
20. [20]
  (20) Wang, H.;Wang, J. L. Electrochim. Acta 2008, 53, 6402. doi: 10.1016/j.electacta.2008.04.080
21. [21]
  (21) Li, M. C.; Bao, D. D.; Ma, C. A. Chem. J. Chin. Univ. 2011, 32 (1), 129. [李美超, 鲍丹丹, 马淳安. 高等学校化学学报,2011, 32 (1), 129.]
22. [22]
  (22) Swaminathan, J.; Ramalingam, M.; Saleem, H.; Sethuraman, V.;Ameen, M. T. N. Spectrochim. Acta A 2009, 74, 1247. doi: 10.1016/j.saa.2009.09.054
23. [23]
  (23) Johnson, S. K.; Houk, L. L.; Feng, J.; Houk, R. S.; Johnson, D.C. Enviro. Sci. Technol. 1999, 33, 2638. doi: 10.1021/es981045r
24. [24]
  (24) Jin, G. P.; Lin, X. Q.; Ding, Y. F. J. Solid State Electrochem.2006, 10, 987. doi: 10.1007/s10008-005-0068-9
25. [25]
  (25) Tong, S. P.; Ma, C. A.; Fei, H. Acta Phys. -Chim. Sin. 2007, 23 (3), 424. [童少平, 马淳安, 费会. 物理化学学报, 2007, 23 (3), 424.] doi: 10.3866/PKU.WHXB20070327
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