Immobilization of Transition-metal Hydroxamates on Polystyrene Resins: Effective Biomimetic Heterogeneous Catalysts for Aerobic Oxidation of Ethylbenzene

doi:10.1007/s40242-015-5072-8

Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (5): 835-840.doi: 10.1007/s40242-015-5072-8

• Articles • Previous Articles Next Articles

Immobilization of Transition-metal Hydroxamates on Polystyrene Resins: Effective Biomimetic Heterogeneous Catalysts for Aerobic Oxidation of Ethylbenzene

WANG Ruixin, WANG Hongjing, WANG Xiaogang, LEI Caiping, SHI Xiaohui

School of Chemical and Environmental Engineering, North University of China, Taiyuan 030051, P. R. China

Received:2015-03-02 Revised:2015-05-07 Online:2015-10-01 Published:2015-07-27
Contact: WANG Ruixin, E-mail: zbdxwrx@nuc.edu.cn E-mail:zbdxwrx@nuc.edu.cn
Supported by:
Supported by the National Young Scientists Fund of China(No.21307116), the Natural Science Foundation of Shanxi Province, China(No.2014011017-5), the Project for the Outstanding Innovative Teams of Higher Learning Institutions of Shanxi Province, China(No.201504) and the Fund Program for the Scientific Activities of Selected Returned Overseas Professionals in Shanxi Province, China(No.20140828).

Abstract

Abstract:

Salicylhydroxamic acid(SHA) was covalently grafted onto chloromethylated crosslinked polystyrene spheres(CMCPS) by the Friedel-Crafts alkylation reaction. The amount of SHA on CPS was found to be mainly dependent on the amount of Lewis acid(SnCl₄) used and the reaction temperature. Under optimized conditions, the amount of SHA attached to CPS could reach up to 0.43 g/g CPS. Transition metal ions[Co(II), Cu(II), Fe(III) or Mn(II)] were then introduced into the resulting SHA-functionalized microspheres(SHA/CPS) through SHA-metal ion chelation. The obtained microspheres MSHA/CPS were explored as biomimetic catalysts for the aerobic oxidation of ethylbenzene(EB) to ethylbenzene hydroperoxide(EBHP). Among the four supported metal catalysts, FeSHA/CPS showed the highest catalytic activity and good reusability, indicating its great potential as an effective heterogeneous catalyst for the aerobic oxidation of hydrocarbons under mild conditions.

Key words: Salicylhydroxamic acid-transition metal complex, Immobilization, Crosslinked polystyrene, Catalytic oxidation, Ethylbenzene

WANG Ruixin, WANG Hongjing, WANG Xiaogang, LEI Caiping, SHI Xiaohui. Immobilization of Transition-metal Hydroxamates on Polystyrene Resins: Effective Biomimetic Heterogeneous Catalysts for Aerobic Oxidation of Ethylbenzene[J]. Chemical Research in Chinese Universities, 2015, 31(5): 835-840.

References

[1] Nam N. H., Huong T. L., Dung D. T. M., Dung P. T. P., Oanh D. T. K., Park S. H., Kim K., Han B. W., Yun J., Kang J. S., Kim Y., Han S. B., J. Enzym. Inhib. Med. Chem., 2014, 29(5), 611
[2] Qin Y., Zhao X. J., Fang Y., Int. J. Gynecol. Cancer, 2014, 24(8), 1373
[3] Xu J., Franklin S. J., Whisenhun D. W. J., Raymond K. N., J. Am. Chem. Soc., 1995, 117, 7245
[4] Zeng W., Zeng G. Y., Qin S. Y., Chin. J. Org. Chem., 2003, 23(11), 1213
[5] Jiao J., Fang H., Wang X. J., Guan P., Yuan Y. M., Xu W. F., Eur. J. Med. Chem., 2009, 44, 4470
[6] Li H. B., Qin C., Liang W., Wang L. P., Hao M. A., Jin B., Liang X. L., Qin S.Y., J. Mol. Catal., 2009, 23(1), 62
[7] Helmick J. S., Martin K. A., Heinrich J. L., J. Am. Chem. Soc., 1991, 113, 3459
[8] Raymond K. N., Coord. Chem. Rev., 1990, 105, 135
[9] Busch D. H., Alcock N. W., Chem. Rev., 1994, 94, 585
[10] Li G. Q., Govind R., Ind. Eng. Chem. Res., 1994, 33, 755
[11] Zhang S. Y., Jiang P. P., Leng Y., Xu Y. C., Mo G. T., Bian G., Chem. J. Chinese Universities, 2013, 34(7), 1703
[12] Mukherjee M., Ray A. R., J. Mol. Catal. A, 2007, 266(1/2), 207
[13] Han Z. J., Zhou H., Chen H. W., Dai H., J. Inorg. Chem., 1992, 8(4), 421
[14] Yang H., Qin S. Y., Lu X. X., Zeng W., Chin. Chem. Lett., 1999, 10, 79
[15] Li H. B., Du Y., Wei X. Y., Qin S. Y., Acta Chim. Sinica, 2002, 60(5), 886
[16] Barlan A. U., Zhang W., Yamamoto H., Tetrahedron, 2007, 63(27), 6075
[17] Gharah N., Chattopadhyay B., Maiti S. K., Mukherjee M., Transition Met. Chem., 2010, 35(5), 531
[18] Sun B., Qin S. Y., Chem. Res. Appl.(China), 2011, 23(1), 92
[19] Li Y. F., Gao B. J., Yu Y. L., J. Mol. Catal.(China), 2013, 27(3), 271
[20] Wang R. X., Zhu H. L., Gao B. J., Reac. Kinet. Mech. Cat., 2011, 103, 431
[21] Barrio L., Toribio P. P., Campos-Martin J. M., Fierro J. L. G., Tetrahedron, 2004, 60, 11527
[22] Lü C. L., Gao B. J., Liu Q., Qi C. S., Colloid Polym. Sci., 2008, 286, 553
[23] Alcántara R., Canoira L., Joao P. G., Santos J. M., Vázquez I., Appl. Catal. A, 2000, 203, 259
[24] Agrawal D. R., Tandon S. G., J. Indian Chem. Soc., 1971, 48, 571
[25] Toribio P. P., Campos-Martin J. M., Fierro J. L. G., J. Mol. Catal. A, 2005, 227, 101
[26] Lu Z. F., Zhan F. T., Qin S. Y., Modern Chemical Industry, 2000, 20(5), 32
[27] Toribio P. P., Campos-Martin J. M., Fierro J. L. G., Appl. Catal. A, 2005, 294, 290
[28] Li H. B., Qin C., Yang W. B., Hu X. P., Qin S. Y., Chin. Chem. Lett., 2007, 18, 103

Immobilization of Transition-metal Hydroxamates on Polystyrene Resins: Effective Biomimetic Heterogeneous Catalysts for Aerobic Oxidation of Ethylbenzene

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	ZHANG Xingcong, ZHONG Yunzhu, CHEN Hongyu, CHENG Yujie, SUN Qingdi, ZHANG Hao, HE Qian, ZHANG Ying, GUO Guanghui, HE Xiaohui, JI Hongbing. Synthesis of Nitrogen-doped Carbon Supported Cerium Single Atom Catalyst by Ball Milling for Selective Oxidation of Ethylbenzene [J]. Chemical Research in Chinese Universities, 2022, 38(5): 1258-1262.
[2]	CHENG Dajun, and MENG Xiangju. Recent Advances of Beta Zeolite in the Volatile Organic Compounds(VOCs) Elimination by the Catalytic Oxidations [J]. Chemical Research in Chinese Universities, 2022, 38(3): 716-722.
[3]	LUO Li, WANG Sen, WU Zhiwei, QIN Zhangfeng, DONG Mei, WANG Jianguo, FAN Weibin. Influence of the ZSM-5 Support Acidity on the Catalytic Performance of Pd/ZSM-5 in Lean Methane Oxidation [J]. Chemical Research in Chinese Universities, 2022, 38(1): 229-236.
[4]	GUO Ruihua, QIAN Fei, AN Shengli, ZHANG Jieyu, CHOU Kuo-Chih, YE Jinyu, ZHOU Zhiyou. Effect of Acid Treatment on Electrocatalytic Performance of PtNi Catalyst [J]. Chemical Research in Chinese Universities, 2021, 37(3): 686-695.
[5]	YU Bowen, LOU Caiyi, ZHANG Wenna, XU Shutao, HAN Jingfeng, YU Zhengxi, WEI Yingxu, LIU Zhongmin. Insight into the Dual Cycle Mechanism of Methanol-to-Olefins Reaction over SAPO-34 Molecular Sieve by Isotopic Tracer Studies [J]. Chemical Research in Chinese Universities, 2020, 36(6): 1203-1208.
[6]	LU Lulu, WANG Chan, WANG Mei, SONG Qijun. Catalytic Oxidation of Trichloroethylene over RuO₂ Supported on Ceria-zirconia Mixed Oxide [J]. Chemical Research in Chinese Universities, 2019, 35(1): 71-78.
[7]	YU Zhihui, LIU Dandan, LI Yunqiao. Facile Route to Enzyme Immobilization: Gloucose Oxidase Entrapped in Titania Under Mild Environmental Conditions and Consequent Electrochemical Sensor Response [J]. Chemical Research in Chinese Universities, 2018, 34(3): 490-494.
[8]	SU Yuhan, QI Xuefei, TIAN Jun, LIN Chenhui, CHEN Ligong, LI Yang, JIN Yuehua, YAN Xilong, WANG Bowei. Wang Resin-supported Enantioselective Catalysts for the Asymmetric Michael Additions ofAcetone to β-Nitroolefins [J]. Chemical Research in Chinese Universities, 2018, 34(1): 84-89.
[9]	GENG Zhi, YU Yang, ZHU Suiyi, YU Hongbin, LIU Jiancong, BIAN Dejun, YANG Xia, HUO Hongliang, HUO Mingxin. Comparing Polyethersulfone and Polyurethane-immobilized Cells of Comamonas testosteroni QYY in Treatment of an Accidental Dye Wastewater [J]. Chemical Research in Chinese Universities, 2017, 33(1): 36-43.
[10]	LIU Lili, TAI Xishi, YU Guanglin, GUO Huanmei, MENG Qingguo. Gold and Silver Nanoparticles Supported on Metal-organic Frameworks: a Highly Active Catalyst for Three-component Coupling Reaction [J]. Chemical Research in Chinese Universities, 2016, 32(3): 443-450.
[11]	GENG Zhi, ZHU Suiyi, YU Yang, LU Ying, LIN Rao, GUO Shujun, BIAN Dejun, YANG Xia, HUO Mingxin, HUO Hongliang. Novel Porous Polyethersulfone Beads as Matrix to Immobilize Comamonas testosteroni sp. bdq06 in Quinoline Biodegradation [J]. Chemical Research in Chinese Universities, 2015, 31(4): 645-650.
[12]	WANG Ruixin, LEI Caiping, WANG Hongjing, SHI Xiaohui. Chelating Properties of Salicylhydroxamic Acid-functionalized Polystyrene Resins and Its Application to Efficient Removal of Heavy Metal Ions from Aqueous Solutions [J]. Chemical Research in Chinese Universities, 2015, 31(3): 471-476.
[13]	LIU Xiao-hong, LI Yong-jin, YANG Wei-jun, GUO Can-cheng. Synthesis of Iron Chlorophyllins and Their Catalytic Performance for Aerobic Oxidation of Cyclohexene [J]. Chemical Research in Chinese Universities, 2013, 29(3): 526-532.
[14]	SUN Hui, CHEN Rui-chao, LIU Shu, XU Guo-zhi. Surface Heparinization of Poly(ether ether ketone) [J]. Chemical Research in Chinese Universities, 2012, 28(3): 542-545.
[15]	SUN Hui, CHEN Rui-chao, LI Ang, XU Guo-zhi. Immobilization of Bovine Serum Albumin on Poly(ether ether ketone) for Surface Biocompatibility Improvement [J]. Chemical Research in Chinese Universities, 2012, 28(2): 353-357 .