Citation: LU Chun-Li, FU Zai-Hui, LIU Ya-Chun, LIU Feng-Lan, QIN Jin-Wei, HE Xiang-Ling, YIN Du-Lin. Selective Oxidation of Ethylbenzene with Hydrogen Peroxide Catalyzed by 5,7-Dibromo-8-quinolinolato Manganese Complexes[J]. Acta Physico-Chimica Sinica, ;2010, 26(10): 2705-2710. doi: 10.3866/PKU.WHXB20100936 shu

Selective Oxidation of Ethylbenzene with Hydrogen Peroxide Catalyzed by 5,7-Dibromo-8-quinolinolato Manganese Complexes

1.
Key Laboratory of Resource Fine-Processing and Advanced Materials of Hunan Province, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research of Ministry of Education of China, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, P. R. China

Received Date: 17 February 2010
Available Online: 27 September 2010
Fund Project: 国家自然科学基金(20873040, 20573035)资助项目 (20873040, 20573035)

Two 5,7-dibromo-8-quinolinolato manganese complexes in tetradentate (Q₂Mn^II) and hexadentate (Q₃Mn^III) modes were prepared and then characterized by Fourier transform infrared (FT-IR) spectrometry. We found that both Mn complexes, together with NH₄OAC and HOAc, efficiently catalyzed the oxidation of ethylbenzene to acetophenone by hydrogen peroxide in an acetone -water medium at 20 ^oC. Q₃Mn^IIIshowed much higher catalytic activity for this reaction thanQ₂Mn^II, affordinga 27% ethylbenzene conversion and more than 95% selectivity for acetophenone under optimum conditions.Q₃Mn^IIIwas reused three times without significant deactivation, indicating od stability.
- 5,7-Dibromo-8-guinolinolato Mn(III) complex,
- Hexadentate mode,
- Ethylbenzene,
- Acetophenone,
- Selective oxidation
1. [1]
  
  1. Yang, G. Y.; Ma, Y. F.; Xu, J. J. Am. Chem. Soc., 2004, 126: 10542
2. [2]
  2. Wang, R. M.; Chai, C. P.; He, Y. F.; Wang, Y. P.; Li, S. B. Eur. Polym. J., 1999, 35: 2051
3. [3]
  3. Colin, E.; Michael, S. S.; Raymond, W. W. Combust. Flame, 2003, 132: 291
4. [4]
  4. Yasuhiko, K. J. Inorg. Organomet. Polym., 2000, 10: 127
5. [5]
  5. Ma, H.; Xu, J.; Chen, C.; Zhang, Q. H.; Ning, J. B.; Miao, H.; Zhou, L. P.; Li, X. Q. Catal. Lett., 2007, 113: 104
6. [6]
  6. Chisem, I. C.; Martin, K.; Shieh, T.; Chisem, J.; Clark, J. H.; Jachuck, R.; MacQuarrie, D. J.; Rafelt, J.; Ramshaw, C.; Scott, K. Org. Proc. Res. Dev., 1997, 1: 365
7. [7]
  7. Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Chem. Rev., 2005, 105: 2329
8. [8]
  8. Ma, H.; Xu, J.; Chen, C.; Zhang, Q. H.; Ning, J. B.; Miao, H.; Zhou, L. P.; Li, X. Q. Catal. Lett., 2007, 113: 3
9. [9]
  9. Yoshino, Y. S.; Hayashi, Y.; Iwahama, T. J. Org. Chem., 1997, 62: 6810
10. [10]
  10. Recupero, F.; Punta, C. Chem. Rev., 2007, 107: 3800
11. [11]
  11. Xu, H. F.; Tang, R. R.; ng, N. H. Progress in Chemistry, 2007, 19: 1736 [许海峰, 唐瑞仁,龚年华.化学进展, 2007, 19: 1736]
12. [12]
  12. Ishii, Y.; Nakayama, K.; Takeno, M. J. Org. Chem., 1995, 60: 3934
13. [13]
  13. Masui, M.; Ueshima, T.; Ozaki, S. S. J. Chem. Soc., 1983, 8: 479
14. [14]
  14. Einhom, C.; Einhom, J.; Marcada1-Abbadi, C. Chem. Commun., 1997, (13): 447
15. [15]
  15. Maurya, M.; Kumar, M.; Kumar, U. J. Mol. Catal. A, 2007, 273: 133
16. [16]
  16. Maurya, M.; Arya, A.; Adao, P. Appl. Catal. A, 2008, 351: 239
17. [17]
  17. Balland, V.; Mathieu, D. J. Mol. Catal. A, 2004, 215: 81
18. [18]
  18. Mal, N. K.; Ramaswamy, A. V. Appl. Catal. A, 1996, 143: 75
19. [19]
  19. Xavier, K. O.; Chacko, J.; Mohammed, Y. K. K. Appl. Catal. A, 2004, 258: 251
20. [20]
  20. Mal, N. K.; Ramaswamy, A. V. Appl. Catal. A, 1996, 143: 75
21. [21]
  21. Qiao, J. D.; Li, Q.; Xing, Y. Fine Chemicals, 2001, 8: 475 [乔庆东,李琪, 刑宇. 精细化工, 2001, 8: 475]
22. [22]
  22. Ronny, N.; Mauricio, D. V. J. Mol. Catal. A-Chem., 1993, 84: 93
23. [23]
  23. Zhong, S.; Tan, Y. M.; Fu, Z. H. J. Catal., 2008, 256: 154
24. [24]
  24. Zhong, S.; Tan, Y. M.; Fu, Z. H. Adv. Synth. Catal., 2008, 350: 802
25. [25]
  25. Ye, Z. P.; Fu, Z. H.; Zhong, S. J. Catal., 2009, 261: 110
26. [26]
  26. Xie, F.; Fu, Z. H.; Zhong, S. J. Mol. Catal. A, 2009, 307: 93
27. [27]
  27. Xie, F.; Fu, Z. H.; Zhong, S. Chinese Journal of Catalysis, 2009, 10: 981 [谢芳, 伏再辉, 衷晟.催化学报, 2009, 10: 981]
28. [28]
  28. Chisem, I. C.; Martin, K.; Shieh, M. T. Org. Process Res. Dev., 1997, 1: 365
29. [29]
  29. Hubin, T. J.; McCormick, J. M.; Alcock, N. W.; Busch, D. H. Inorg. Chem., 2001, 40: 435
30. [30]
  30. Zhao, G. D.; L俟, Y.; Xi, Z. W. Chemistry, 2004, 67(11): w089 [赵公大,吕迎, 奚祖威. 化学通报, 2004, 67(11): w089]
1. [1]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
2. [2]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
3. [3]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
4. [4]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
5. [5]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
6. [6]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
7. [7]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
8. [8]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
9. [9]
  Qilu DU , Li ZHAO , Peng NIE , Bo 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
10. [10]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
11. [11]
  Wei Li , Ze Chang , Meihui Yu , Ying Zhang . Curriculum Ideological and Political Design of Piezoelectricity Measurement Experiments of Coordination Compounds. University Chemistry, 2024, 39(2): 77-82. doi: 10.3866/PKU.DXHX202308004
12. [12]
  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
13. [13]
  Cunling Ye , Xitong Zhao , Hongfang Wang , Zhike Wang . A Formula for the Calculation of Complex Concentrations Arising from Side Reactions and Its Applications. University Chemistry, 2024, 39(4): 382-386. doi: 10.3866/PKU.DXHX202310043
14. [14]
  Keweiyang Zhang , Zihan Fan , Liyuan Xiao , Haitao Long , Jing Jing . Unveiling Crystal Field Theory: Preparation, Characterization, and Performance Assessment of Nickel Macrocyclic Complexes. University Chemistry, 2024, 39(5): 163-171. doi: 10.3866/PKU.DXHX202310084
15. [15]
  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
16. [16]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang 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
17. [17]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
18. [18]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
19. [19]
  Jinfeng Chu , Yicheng Wang , Ji Qi , Yulin Liu , Yan Li , Lan Jin , Lei He , Yufei Song . Comprehensive Chemical Experiment Design: Convenient Preparation and Characterization of an Oxygen-Bridged Trinuclear Iron(III) Complex. University Chemistry, 2024, 39(7): 299-306. doi: 10.3866/PKU.DXHX202310105
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(1191)
Abstract views(2768)
HTML views(5)

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