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氧气直接氧化苯制备苯酚
Direct Oxidation of Liquid Benzene to Phenol with Molecular Oxygen
苯酚是重要的化工原料，其工业生产主要是通过异丙苯氧化法制备，该方法存在制备流程长、消耗丙烯多以及产生大量副产物等不足。苯直接氧化制备苯酚，特别是氧气直接氧化苯制备苯酚，因其步骤少、操作成本低、环境友好等特点已成为苯酚绿色制备的研究热点。本文较为系统地总结了氧气氧化苯液相法合成苯酚的研究工作，综述了该反应体系下的反应机理以及所使用的催化剂、还原剂等；归纳了反应温度、反应压力、还原剂用量及反应溶剂等反应条件对苯酚产率的影响；分析了目前氧气直接氧化苯液相法制苯酚研究中存在的问题，并总结了未来的研究方向。
Phenol is a kind of important chemical materials, which is mainly produced from isopropylbenzene oxidation process. The drawbacks of the process include long synthesis process, consuming propylene and forming byproducts. Directly oxidation of benzene to phenol with molecular oxygen, possessing the advantages of less steps, low cost and environmental friendly, has become the research hotspot in green preparation of phenol. In this review, the progress of oxidation of liquid benzene to phenol with oxygen is summarized systematically. The reaction system, including the reaction mechanism, catalysts, and reductant is reviewed. The effects of reaction temperature, oxygen pressure, reductant and solvent on the yields of phenol are also discussed. Furthermore, the current research problems and future research perspectives are also suggested.
Contents
1 Introduction
2 Reaction mechanism
3 Catalysts
3.1 Vanadium-based catalysts
3.2 Copper-based catalysts
3.3 Heteropolyacids-based catalysts
3.4 Other catalysts
4 Reductants
5 The effects of reaction conditions
5.1 Reaction temperature
5.2 Reaction pressure
5.3 The account of reductant
5.4 Solvents
6 Conclusion and outlook
benzene
[1] 伯仁(Bo R). 精细化工原料及中间体(Fine Chemical Industrial Raw Materials & Intermediates), 2012, 8 (144): 30.
[2] 刘洁(Liu J), 梅来宝(Mei L B). 精细石油化工进展(Advances in Fine Petrochemicals), 2007, 8 (8): 41.
[3] Lücke B, Narayana K V, Martin A, Jähnisch K. Adv. Synth. Catal., 2004, 346 (12): 1407.
[4] 任永利(Ren Y L), 王莅(Wang L), 张香文(Zhang X W). 化学进展(Progress in Chemistry), 2003, 15 (5): 420.
[5] 尹双凤(Yin S F), 伍水生(Wu S S), 代威力(Dai W L), 李文生(Li W S), 黄孟光(Huang M G), 周小平(Zhou X P). 化学进展(Progress in Chemistry), 2007, 19 (5): 735.
[6] Jiang T, Wang W T, Han B X. New J. Chem., 2013, 37: 1654.
[7] Bianchi D, Bortolo R, Tassinari R, Ricci M, Vignola R. Angew. Chem. Int. Ed., 2000, 112 (23): 4491.
[8] Borah P, Ma X, Nguyen K T, Zhao Y L. Angew. Chem. Int. Ed., 2012, 51 (31): 7756.
[9] Kamata K, Yamaura T, Mizuno N. Angew. Chem. Int. Ed., 2012, 51 (29): 7275.
[10] Tang D Y, Zhu L F, Hu C W. RSC Adv., 2012, 2 (6): 2329.
[11] Xia H A, Sun K Q, Sun K J, Feng Z C, Li W X, Li C. J. Phys. Chem. C, 2008, 112 (24): 9001.
[12] Yamanaka H, Hamada R, Nibuta H, Nishiyama S, Tsuruya S. J. Mol. Catal. A: Chem., 2002, 178 (1): 89.
[13] Kato C N, Hasegawa M, Sato T, Yoshizawa A, Inoue T, Mori W. J. Catal., 2005, 230 (1): 226.
[14] Kharitonov A S, Sobolev V I, Panov G I. Russ. Chem. Rev., 1992, 61: 1130.
[15] 高肖汉(Gao X H), 吕雪川(Lv X C), 徐杰(Xu J). 分子催化(Journal of Molecular Catalysis (China)), 2008, 22 (4): 379.
[16] 陈练洪(Chen L H), 李稳宏(Li W H), 李冬(Li D), 韩枫(Han F). 化工进展(Chemical Industry and Engineering Progress), 2005, 24 (3): 236.
[17] Roduner E, Kaim W, Sarkar B, Urlacher V B, Pleiss J, Gläser R, Einicke W D, Sprenger G A, Beifuß U, Klemm E, Liebner C, Hieronymus H, Hsu S F, Plietker B, Laschat S. Chem. Cat. Chem., 2013, 5 (1): 82.
[18] Kubacka A, Wang Z, Sulikowski B, Cortés Corberán V. J. Catal., 2007, 250 (1): 184.
[19] Bal R, Tada M, Sasaki T, Iwasawa Y. Angew. Chem. Int. Ed., 2005, 45 (3): 448.
[20] Masumoto Y K, Hamada R, Yokota K, Nishiyama S, Tsuruya S. J. Mol. Catal. A: Chem., 2002, 184 (1/2): 215.
[21] Ishida M A, Masumoto Y, Hamada R, Nishiyama S, Tsuruya S, Masai M. J. Chem. Soc., Perkin Trans. 2, 1999, (4): 847.
[22] Miyahara T, Kanzaki H, Hamada R, Kuroiwa S, Nishiyama S, Tsuruya S. J. Mol. Catal. A: Chem., 2001, 176 (1): 141.
[23] Chen J Q, Gao S, Li J, Lv Y. Chin. J. Catal., 2011, 32 (9/10): 1446.
[24] Gao X H, Lv X C, Xu J. Chin. J. Chem., 2009, 27 (11): 2155.
[25] Gu Y Y, Zhao X H, Zhang G R, Ding H M, Shan Y K. Appl. Catal. A: Gen., 2007, 328 (2): 150.
[26] Gao X H, Xu J. Catal. Lett., 2006, 111 (3): 203.
[27] Gao X H, Lv X C, Xu J. Kinet. Catal., 2010, 51 (3): 394.
[28] Zhao L N, Dong Y L, Zhan X L, Cheng Y, Zhu Y J, Yuan F L, Fu H G. Catal. Lett., 2012, 142: 619.
[29] Wang W T, Ding G D, Jiang T, Zhang P, Wu T B, Han B X. Green Chem., 2013, 15 (5): 1150.
[30] Ohtani T, Nishiyama S, Tsuruya S, Masai M. J. Catal., 1995, 155 (1): 158.
[31] Okamura J, Nishiyama S, Tsuruya S, Masai M. J. Mol. Catal. A: Chem., 1998, 135 (2): 133.
[32] Kitamura T, Kanzaki H, Hamada R, Nishiyama S, Tsuruya S. Can. J. Chem., 2004, 82 (11): 1597.
[33] Tani M, Sakamoto T, Mita S, Sakaguchi S, Ishii Y. Angew. Chem. Int. Ed., 2005, 44 (17): 2586.
[34] Liu Y Y, Murata K, Inaba M. Catal. Commun., 2005, 6 (10): 679.
[35] Ge H Q, Leng Y, Zhang F M, Zhou C J, Wang J. Catal. Lett., 2008, 124 (3): 250.
[36] Ge H Q, Leng Y, Zhou C J, Wang J. Catal. Lett., 2008, 124 (3): 324.
[37] Ge H Q, Leng Y, Zhang F M, Piao J R, Zhou C J, Wang J. Sci. China B, 2009, 52 (8): 1264.
[38] Zhou C J, Wang J, Leng Y, Ge H Q. Catal. Lett., 2010, 135 (1): 120.
[39] Zhou C J, Ge H Q, Leng Y, Wang J. Chin. J. Catal., 2010, 31 (6): 623.
[40] Long Z Y, Zhou Y, Chen G J, Zhao P P, Wang J. Chem. Eng. J., 2014, 239: 19.
[41] Wu Q, Yang H, Cheng H W, Liu Z G, You W S, Gao S. J. Mol. Struct., 2012, 1030: 83.
[42] Yang H, Li J, Wang L Y, Dai W, Lv Y, Gao S. Catal. Commun., 2013, 35: 101.
[43] Ichihashi Y, Taniguchi T, Amano H, Atsumi T, Nishiyama S, Tsuruya S. Top. Catal., 2008, 47 (3): 98.
[44] Laufer W, Niederer J P M, Hoelderich W F. Adv. Synth. Catal., 2002, 344 (10): 1084.
[45] Orita H, Hayakawa T, Shimizu M, Takehira K. J. Mol. Catal., 1987, 42 (1): 99.
[46] Liu Y Y, Murata K, Inaba M. J. Mol. Catal. A: Chem., 2006, 256 (1/2): 247.
[47] Burton H A, Kozhevnikov I V. J. Mol. Catal. A: Chem., 2002, 185 (1/2): 285.
[48] Sumimoto S, Tanaka C, Yamaguchi S, Ichihashi Y, Nishiyama S, Tsuruya S. Ind. Eng. Chem. Res., 2006, 45 (22): 7444.
[49] Yang H, Chen J Q, Li J, Lv Y, Gao S. Appl. Catal. A: Gen., 2012, 415/416: 22.
[50] Guo C, Du W D, Chen G, Shi L, Sun Q. Catal. Commun., 2013, 37: 19.
[51] Bortolotto L, Dittmeyer R. Sep. Purif. Technol., 2010, 73 (1): 51.
[52] Ehrich H, Berndt H, Pohl M M, Jähnisch K, Baerns M. Appl. Catal. A: Gen., 2002, 230 (1): 271.
[53] Sakamoto T, Takagaki T, Sakakura A, Obora Y, Sakaguchi S, Ishii Y. J. Mol. Catal. A: Chem., 2008, 288 (1): 19.
[54] Yamaguchi S, Sumimoto S, Ichihashi Y, Nishiyama S, Tsuruya S. Ind. Eng. Chem. Res., 2005, 44 (1): 1.
[55] Kanzaki H, Kitamura T, Hamada R, Nishiyama S, Tsuruya S. J. Mol. Catal. A: Chem., 2004, 208 (1): 203.
[56] Balducci L, Bianchi D, Bortolo R, D'Aloisio R, Ricci M, Tassinari R, Ungarelli R. Angew. Chem. Int. Ed., 2003, 115 (40): 5087.
[57] Peng J J, Shi F, Gu Y L, Deng Y Y. Green Chem., 2003, 5(2): 224.
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