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化学进展 2007, Vol. 19 Issue (05): 735-744 前一篇   后一篇

• 综述与评论 •

分子氧催化氧化苯直接合成苯酚*

尹双凤**;伍水生;代威力;李文生;黄孟光;周小平**   

  1. 湖南大学化学化工学院 长沙 410082

  • 收稿日期:2006-08-16 修回日期:1900-01-01 出版日期:2007-05-24 发布日期:2007-05-24
  • 通讯作者: 尹双凤；周小平
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Direct Phenol Synthesis by Catalytic Oxidation of Benzene with Molecular Oxygen

Yin Shuangfeng**;Wu Shuisheng;Dai Weili; Li Wensheng;Huang Mengguang; Zhou Xiaoping**   

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
  • Received:2006-08-16 Revised:1900-01-01 Online:2007-05-24 Published:2007-05-24
苯酚是重要的有机合成中间体,当前主要通过异丙苯法合成苯酚的技术路线存在制备流程长、消耗丙烯、副产丙酮等不足。以分子氧为氧化剂由苯氧化直接合成苯酚则具有潜在重大的经济效益、社会效益和环境效益，已成为催化与有机合成等研究领域中极具挑战性的热点课题之一。本文较为系统地总结了分子氧氧化苯通过一步法合成苯酚的研究工作，着重综述了用于该反应的催化剂如Pd、Cu、V等金属或其化合物，也归纳了影响此反应的主要因素，并介绍相应的反应机理。最后，对分子氧催化氧化苯合成苯酚反应的研究提供了一些建议和展望。
关键词： 苯, 分子氧, 苯酚, 催化氧化
Phenol is an important synthesis intermediate in chemical industry. Currently, phenol is produced from the isopropylbenzene oxidation process, which consumes propylene and forms acetone as by-product. Phenol synthesis from the direct catalytic oxidation of benzene by molecular oxygen is attractive from the standpoint of its potential economical benefit, social benefit as well as environmental benefit. However, the research works in this area are still regarded as one of the most difficult challenges for both catalysis and organic synthesis. This mini-review systematically summarizes the progress of direct phenol synthesis by catalytic oxidation of benzene using molecular oxygen as oxidant, with emphasis on the explored catalysts such as Pd, Cu, V compounds. We also outline the factors affecting phenol synthesis and the possible reaction mechanisms on different catalysts. In addition, some suggestions are given for future investigations on direct phenol synthesis by catalytic oxidation of benzene with molecular oxygen.
Key words: benzene, molecular oxygen, phenol, catalytic oxidation

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[ 1 ] Bal R , Tada M, Sasaki T , Iwasawa Y. Angew. Chem. Int . Ed. ,2006 , 45 (3) : 448 —452
[ 2 ] 季东(Ji D) , 任通( Ren T) , 张小明( Zhagn X M) , 索继栓(Suo J S) , 丁勇(Ding Y) . 化学进展(Progress in Chemistry) ,2003 , 15 (1) : 51 —59
[ 3 ] 党红翌(Dang H L) , 张瑛(Zhang Y) . 齐鲁石油化工(Journal of Qilu Petrochemical Technology) , 1999 , 27(2) : 127 —130
[ 4 ] Moro2oka Y. Catal . Today , 1998 , 45 : 3 —12
[ 5 ] Pirutko L V , Parenago O , Lunina E , et al . React . Kinet . Catal .Lett . , 1994 , 52 : 275 —283
[ 6 ] 李明强(Li M Q) , 蹇锡高(Jian X G) , 韩铁民(Han T M) , 刘炼(Liu L) , 史云龙(Shi YL) . 催化学报(Chinese Journal of Catalysis) , 2004 , 25 (9) : 681 —682
[ 7 ] 兰忠(Lan Z) , 王立秋(Wang L Q) , 张守臣(Zhang S C) , 刘长厚( Liu C H) . 化工进展( Chemical Industry and Engineering) , 2002 , 21 (9) : 621 —625
[ 8 ] 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 —426
[ 9 ] 高飞雪(Gao F X) , 华瑞茂(Hua R M) . 化学进展(Progress in Chemistry) , 2005 , 17 (3) : 437 —450
[10] 陈胜洲(Chen S Z) , 董新法(Dong X F) , 林维明(Lin W M) .工业催化( Industrial Catalysis) , 2003 , 11 (6) : 34 —37
[11] Udenfriend S , Clark C T , Axelrod J , Brodie B B , J . Biol .Chem. , 1954 , 208 (2) : 731 —737
[12] Orita H , Hayakawa Y, Shimizu M, Takehira K. J . Mol . Catal . ,1987 , 42 : 99 —106
[13] Chen Y W, Lu Y H. Ind. Eng. Chem. Res. , 1999 , 38 (5) :1893 —1903
[14] Ohtani T , Nishiyama S , Tsuruya S , Masai M. J . Catal . , 1995 ,155 : 158 —162
[15] Castagnola N B , Kropf A J , Marshall C L. Appl . Catal . A:Gen. , 2005 , 290 (1P2) : 110 —122
[16] Shibata Y, Hamada R , Ueda T , Ichihashi Y, Nishiyama S ,Tsuruya S. Ind. Eng. Chem. Res. , 2005 , 44 (23) : 8765 —8772
[17] Jintoku T , Takaki K, Fujiwara Y, Fuchita Y, Hiraki K. Bull .Chem. Soc. Jpn. , 1990 , 63 (2) : 438 —441
[18] Murata K, Yanyong R , Inaba M. Catal . Lett . , 2005 , 102 (3/4) : 143 —147
[19] Niwa S , Eswaramoorthy M, Nair J , Raj A , Itoh N , Shoji H ,Namba T , Mizukami F A. Science , 2002 , 295 (5552) : 105 —107
[20] Miyake T , Hamada M, Niwa H , Nishizuka M, Oguri M. J . Mol .Catal . A: Chemical , 2002 , 178 (1P2) : 199 —204
[21] Kuznetsova N I , Detusheva L G, Kuznetsova L I , Fedotov M A ,Likholobov V A. J . Mol . Catal . A: Chemical , 1996 , 114(1/3) : 131 —139
[22] Cai R , Song S Q , Ji B F , Yang W S , Xin Q , Sun G Q ,Douvartzides S , Tsiakaras P. Appl . Catal . B Environmental ,2005 , 61 (3/4) : 184 —191
[23] Ishida M A , Masumoto Y, Hamada R , Nishiyama S , Tsuruya S ,Masai M. J . Chem. Soc. , Perkin Trans. , 1999 , 2 (4) : 847 —853
[24] Liu Y Y, Murata K, Inaba M. Catal . Commun. , 2005 , 6 (10) :679 —683
[25] Cornils B , Herrmann WA. J . Catal . , 2003 , 216 (1/2) : 23 —31
[26] Lucke B , Narayana KV , Martin A , et al . Adv. Synth. Catal . ,2004 , 346 : 1407 —1424
[27] Kunai A , Hata S , Ito S , Sasaki K. J . Org. Chem. , 1986 , 51 :3471 —3474
[28] Kunai A , Wani T , Uehara Y, Iwasaki F , Kuroda Y, Ito S ,Sasaki K. Bull Chem. Soc. Jpn. , 1989 , 62 : 2613 —2617
[29] Kitano T , Nakai T , Nitta M, Mori M, Ito S , Sasaki S. Bull Chem. Soc. Jpn. , 1994 , 67 (10) : 2850 —2855
[30] Sakata S , Nakai T , Yahiro H , Shiotani M. Appl . Catal . A:Gen. , 1997 , 165 (1/2) : 467 —472
[31] Hamada R , Shibata Y, Nishiyama S , Tsuruya S. Phys. Chem.Chem. Phys. , 2003 , 5 (5) : 956 —965
[32] Okamura J , Nishiyama S , Tsuruya S , Masai M. J . Mol . Catal .A: Chemical , 1998 , 135 (2) : 133 —142
[33] Kanzaki H , Kitamura T , Hamada R , Nishiyama S , Tsuruya S. J .Mol . Catal . A , 2004 , 208 (1/2) : 203 —211
[34] Miyahara T , Kanzaki H , Hamada R , Kuroiwa S , Nishiyama S ,Tsuruya S. J . Mol . Catal . A: Chemical , 2001 , 176 ( 1/2) :141 —150
[35] Takata K, Yamaguchi S , Nishiyama S , Tsuruya S. J . Mol .Catal . A: Chemical , 2005 , 225 (1) : 125 —130
[36] Yamanaka H , Hamada R , Nibuta H , Nishiyama S , Tsuruya S. J .Mol . Catal . A: Chemical , 2002 , 178 (1/2) : 89 —95
[37] Liptakov B , Bahidsky M, Hronec M. Appl . Catal . A: Gen. ,2004 , 263 (1) : 33 —38
[38] Liptakova B , Hronec M, Cvengrosova Z. Catal . Today , 2000 , 61(1/4) : 143 —148
[39] Bahidsky M, Hronec M. Catal . Today , 2005 , 99 (1/2) : 187 —192
[40] Bahidsky M, Hronec M. Catal . Today , 2004 , 91/92 : 13 —16
[41] Jintoku T , Takaki K, Fujiwara Y. Chem. Lett . , 1987 , 1865 —1867
[42] Schuchardt U , Cruz A T , Passoni L C , Collins C H. Stud. Surf .Sci . Catal . , 1994 , 82 : 551 —559
[43] Passoni L C , Cruz A T , Buffon R , Schuchardt U. J . Mol . Catal .A: Chemical , 1997 , 120 (1/3) : 117 —123
[44] Burton H A , Kozhevnikov I V. J . Mol . Catal . A: Chemical ,2002 , 185 (1/2) : 285 —290
[45] Shimizu K, Akahane H , Kodama T , Kitayama Y. Appl . Catal .A: Gen. , 2004 , 269 (1/2) : 75 —80
[46] 曹声春(Cao S C) , 杨礼嫦( Yang L C) , 黄孟光(Huang M G) . 催化学报, 1996 , 16(1) : 76 —78
[47] Miyaki T , Hamada M, Sasaki Y, Oguri M. Appl . Catal . A:Gen. , 1995 , 131 (1) : 33 —42
[48] Ehrich H , Berndt H , Pohl M M, Jahnisch K, Baerns M. Appl .Catal . A: Gen. , 2002 , 230 (1/2) : 271 —280
[49] Laufer W, Hoelderich W F. Chem. Commun. , 2002 , ( 16) :1684 —1685
[50] Kuznetsova N I , Kuznetsova L I , Likholobov V A , Pez G P.Catal . Today , 2005 , 99 (1/2) : 193 —198 and references therein
[51] Otsuka , K, Yamanaka I. Catal . Today , 2000 , 57 (1/2) : 71 —86
[52] Itoh N , Niwa S , Mizukami F , Inoue T , Igarashi A , Namba T.Catal . Commun. , 2003 , 4 (5) : 243 —246
[53] Orita H , Itoh N. Appl . Catal . A: Gen. , 2004 , 258 (1) : 17 —23
[54] Kusakari T , Sasaki T , Iwasawa Y. Chem. Commun. , 2004 ,992 —993
[55] Battistel E , Tassinari R , Fornaroli M, Bonoldi L. J . Mol . Catal .A: Chemical , 2003 , 202 (1/2) : 107 —115
[56] Masumoto Y K, Hamada R , Yokota K, Nishiyama S , Tsuruya S.J . Mol . Catal . A: Chemical , 2002 , 184 (1/2) : 215 —222
[57] Remias J E , Pavlosky TA , Sen A. J . Mol . Catal . A: Chemical ,2003 , 203 (1/2) : 179 —192
[58] Tani M, Sakamoto T , Mita S , Sakaguchi S , Ishii Y. Angew.Chem. Int . Ed. , 2005 , 44 (17) : 2586 —2588
[59] Yamanaka I , Otsuka K, J . Ectrochem. Soc. , 1991 , 138 (4) :1033 —1038
[60] Otsuka K, Kunieda M, Yamanaka I. J . Ectrochem. Soc. , 1992 ,139 (9) : 2381 —2386
[61] Seo Y J , Mukai Y, Tagawa T , Goto S. J . Mol . Catal . A:Chemical , 1997 , 120 (1/3) : 149 —154
[62] Akasaka R , Mashino T , Hirobe M. J . Chem. Soc. , Perk.Trans. 1 , 1994 , (13) : 1817 —1821
[63] De Visser S P , Shaik S. J . Am. Chem. Soc. , 2003 , 125 (24) :7413 —7424
[64] Dong T , Li J , Huang F , Wang L , Tu J , Torimoto Y, Sadakata M, Li Q X. Chem. Commun. , 2005 , (21) : 2724 —2726
[65] Parker J K, Davis S R. J . Am. Chem. Soc. , 1999 , 121 (17) :4271 —4277
[66] Park H , Choi W. Catal . Today , 2005 , 101 (3/4) : 291 —297
[67] Fukuoka A , Fujishima K, Chiba M, Yamagishi A , Inagaki S ,Fukushima Y, Ichikawa M. Catal . Lett . , 2000 , 68 ( 3/4 ) :241 —244
[68] Dai Q X, Xiao H Y, Li W S , Na Y Q , Zhou X P. J . Comb.Chem. , 2005 , 7 (4) : 539 —545
[69] Dai Q X, Xiao H Y, Li W S , Na Y Q , Zhou X P. Appl . Catal .A: Gen. , 2005 , 290 (1/2) : 25 —35
[70] Xiao H Y, Dai Q X, Li W S , Au C T , Zhou X P. J . Mol .Catal . A , 2006 , 245 (1/2) : 17 —25
[71] Tezuka M, Yajima T. Plasma Chem. Plasma Proc. , 1996 , 16(3) : 329 —340
[72] Lee D W, Lee J H , Chun B H , Lee K Y. Plasma Chem. Plasma Proc. , 2003 , 23 (3) : 519 —539
[73] Sekiguchi H , Ando M. Kagaku Kogaku Ronbunshu , 2004 , 30(2) : 183 —185
[74] Bremner D H , Burgess A E , Li F B. Appl . Catal . A: Gen. ,2000 , 203 (1) : 111 —120
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摘要

分子氧催化氧化苯直接合成苯酚*