氧气催化氧化环己烷

佘远斌; 邓金辉; 张龙; 沈海民*

doi:10.7536/PC171102

化学进展 ›› 2018, Vol. 30 ›› Issue (1) :124-136 DOI: 10.7536/PC171102

综述

扫码查看或转发全文

氧气催化氧化环己烷

佘远斌, 邓金辉, 张龙, 沈海民*

作者信息 +

Catalytic Oxidation of Cyclohexane by O₂ as an Oxidant

Yuanbin She, Jinhui Deng, Long Zhang, Haimin Shen*

Author information +

文章历史 +

摘要

本文系统综述了O₂氧化剂用于环己烷催化氧化体系的研究进展，包括金属配合物催化、金属纳米粒子催化、金属氧化物粒子催化、分子筛催化、碳材料催化、光促进催化、杂多酸催化、金属-有机骨架材料催化等。本文认为研究、开发以O₂为氧化剂，高活性高选择性的非均相环己烷催化氧化体系将成为今后环己烷催化氧化研究的主要方向，尤其是多金属甚至多元素复合体系。本综述不仅对开发高催化活性高选择性的环己烷催化氧化体系，改进目前工业上的环己醇环己酮制备工艺具有重要的参考价值，而且还对其他烃类C-H键和C-C键高效催化氧化体系甚至其他氧化体系的研究与开发也具有重要的参考价值。

Abstract

Recent progress in catalytic oxidation of cyclohexane employing O₂ as an oxidant have been reviewed, including the metal complex catalysis, metal nanoparticle catalysis, metal oxide particle catalysis, molecular sieve catalysis, carbon material catalysis, photo-promotion catalysis, polyoxometalates catalysis, metal-organic framework material catalysis and so on. It is pointed out that the research and development of heterogeneous catalytic system by O₂ as an oxidant with high activity and selectivity will be the focus of catalytic oxidation of cyclohexane in the future, especially for the multi-metal composite system, even the multi-element composite system. This paper will not only act as an important reference in the research and development of catalytic system of cyclohexane with high activity and selectivity, and to improve the preparation process of cyclohexanol and cyclohexanone in industry, but also act as an important reference in the research and development of catalytic system for other hydrocarbon oxidation and non-hydrocarbon oxidation.
Contents
1 Introduction
2 Metal complex catalysis
2.1 Non metalloporphyrin catalysis
2.2 Metalloporphyrin catalysis
3 Metal nanoparticle catalysis
4 Metal oxide particle catalysis
5 Molecular sieve catalysis
6 Carbon material catalysis
7 Photo-promotion catalysis
8 Other catalysis
9 Conclusion

Graphical abstract

关键词

环己烷 / 氧化 / 氧气 / 环己醇 / 环己酮

Key words

cyclohexane / oxidation / oxygen / cyclohexanol / cyclohexanone

引用本文

引用格式 ▾

佘远斌, 邓金辉, 张龙, 沈海民*. 氧气催化氧化环己烷[J]. 化学进展, 2018, 30(1): 124-136 DOI:10.7536/PC171102

Yuanbin She, Jinhui Deng, Long Zhang, Haimin Shen*. Catalytic Oxidation of Cyclohexane by O₂ as an Oxidant[J]. Progress in Chemistry, 2018, 30(1): 124-136 DOI:10.7536/PC171102

登录浏览全文

4963

注册一个新账户忘记密码

参考文献

原文顺序 | 出版日期 | 本文引用

[1] Hitomi Y, Arakawa K, Funabiki T, Kodera M. Angew. Chem. Int. Ed., 2012, 51:3448.
[2] Perraud O, Sorokin A B, Dutasta J P, Martinez A. Chem. Commun., 2013, 49:1288.
[3] Garcia-Bosch I, Siegler M A. Angew. Chem. Int. Ed., 2016, 55:12873.
[4] Wang B, Lee Y M, Clemancey M, Seo M S, Sarangi R, Latour J M, Nam W. J. Am. Chem. Soc., 2016, 138:2426.
[5] Xie Y J, Zhang F Y, Liu P L, Hao F, Luo H A. Ind. Eng. Chem. Res., 2015, 54:2425.
[6] Huang G, Liu Y, Cai J L, Chen X F, Zhao S K, Guo Y A, Wei S J, Li X. Appl. Surf. Sci., 2017, 402:436.
[7] Machado G S, de Lima O J, Ciuffi K J, Wypych F, Nakagaki S. Catal. Sci. Technol., 2013, 3:1094.
[8] Ucoski G M, Castro K A D D, Ciuffi K J, Ricci G P, Marques J A, Nunes F S, Nakagaki S. Appl. Catal. A-Gen., 2011, 404:120.
[9] Machado G S, Wypych F, Nakagaki S. Appl. Catal. A-Gen., 2012, 413:94.
[10] Ferreira G K B, Castro K A D D, Machado G S, Ribeiro R R, Ciuffi K J, Ricci G P, Marques J A, Nakagaki S. J. Mol. Catal. A-Chem., 2013, 378:263.
[11] Barbosa I A, de Sousa P C, da Silva D L, Zanardi F B, Zanatta L D, de Oliveira A J A, Serra O A, Iamamoto Y. J. Colloid Interface Sci., 2016, 469:296.
[12] Da Silva V S, Teixeira L I, do Nascimento E, Idemori Y M, DeFreitas-Silva G. Appl. Catal. A-Gen., 2014, 469:124.
[13] Da Silva V S, Meireles A M, Martins D C D, Reboucas J S, DeFreitas-Silva G, Idemori Y M. Appl. Catal. A-Gen., 2015, 491:17.
[14] Da Silva V S, dos Santos Vieira W C, Meireles A M, Ucoski G M, Nakagaki S, Idemori Y M, DeFreitas-Silva G. New J. Chem., 2017, 41:997.
[15] Singha S, Parida K M, Dash A C. J. Porous Mater., 2011, 18:707.
[16] Feng D W, Jiang H L, Chen Y P, Gu Z Y, Wei Z W, Zhou H C. Inorg. Chem., 2013, 52:12661.
[17] Sharbatdaran M, Farzaneh F, Larijani M M, Salimi A, Ghiasi M, Ghandi M. Polyhedron, 2016, 115:264.
[18] Khomane S B, Doke D S, Dongare M K, Halligudi S B, Umbarkar S B. Appl. Catal. A-Gen., 2017, 531:45.
[19] Zhang Y C, Zhao L Y, Zhang H Y, Huang R, Zhao J Q. Appl. Organomet. Chem., 2017, 31:3709.
[20] Bose S, Pariyar A, Biswas A N, Das P, Bandyopadhyay P. Catal. Commun., 2011, 12:1193.
[21] Balamurugan M, Mayilmurugan R, Suresh E, Palaniandavar M. Dalton Trans., 2011, 40:9413.
[22] Sankaralingam M, Vadivelu P, Suresh E, Palaniandavar M. Inorg. Chim. Acta, 2013, 407:98.
[23] Zhang S B, Wang H, Li M, Han J Y, Liu X, Gong J L. Chem. Sci., 2017, 8:4489.
[24] Zadehahmadi F, Tangestaninejad S, Moghadam M, Mirkhani V, Mohammadpoor-Baltork I, Khosropour A R, Kardanpour R. Appl. Catal. A-Gen., 2014, 477:34.
[25] Pires B M, Silva D M, Visentin L C, Drago V, Carvalho N M F, Faria R B, Antunes O A C. Inorg. Chim. Acta, 2013, 407:69.
[26] Grau M, Kyriacou A, Martinez F C, de Wispelaere I M, White A J P, Britovsek G J P. Dalton Trans., 2014, 43:17108.
[27] Kirillova M V, de Paiva P T, Carvalho W A, Mandelli D, Kirillov A M. Pure Appl. Chem., 2017, 89:61.
[28] Chand S S, Sinha S. J. Appl. Polym. Sci., 2013, 130:2127.
[29] Rodionova L I, Smirnov A V, Borisova N E, Khrustalev V N, Moiseeva A A, Grunert W. Inorg. Chim. Acta, 2012, 392:221.
[30] Machado K, Mishra J, Suzuki S, Mishra G S. Dalton Trans., 2014, 43:17475.
[31] Liu C C, Ramu R, Chan S I, Mou C Y, Yu S S F. Catal. Sci. Technol., 2016, 6:7623.
[32] Huang G, Wang W L, Ning X X, Liu Y, Zhao S K, Guo Y A, Wei S J, Zhou H. Ind. Eng. Chem. Res., 2016, 55:2959.
[33] Wu P P, Xiong Z G, Loh K P, Zhao X S. Catal. Sci. Technol., 2011, 1:285.
[34] Zhou J C, Yang X F, Wang Y Q, Chen W J. Catal. Commun., 2014, 46:228.
[35] Alshammari A, Kalevaru V N, Martin A. Catalysts, 2016, 6:97.
[36] Song X F, Hao J M, Bai Y J, Han L M, Yan G F, Lian X, Liu J S. New J. Chem., 2017, 41:4031.
[37] Liu X, Conte M, Weng W H, He Q, Jenkins R L, Watanabe M, Morgan D J, Knight D W, Murphy D M, Whiston K, Kiely C J, Hutchings G J. Catal. Sci. Technol., 2015, 5:217.
[38] Conte M, Liu X, Murphy D M, Taylor S H, Whiston K, Hutchings G J. Catal. Lett., 2016, 146:126.
[39] Li J, Shi Y, Xu L, Lu G Z. Ind. Eng. Chem. Res., 2010, 49:5392.
[40] Duan X G, Liu W M, Yue L M, Fu W, Ha M N, Li J, Lu G Z. Dalton Trans., 2015, 44:17381.
[41] Cao Y H, Luo X Y, Yu H, Peng F, Wang H J, Ning G Q. Catal. Sci. Technol., 2013, 3:2654.
[42] Ide Y, Iwata M, Yagenji Y, Tsunoji N, Sohmiya M, Komaguchi K, Sano T, Sugahara Y. J. Mater. Chem. A, 2016, 4:15829.
[43] Wang H, Zhang Y, Guo Y Y, Zhang L M, Han Y, Zhao X X. RSC Adv., 2016, 6:38176.
[44] Tsukamoto D, Shiro A, Shiraishi Y, Hirai T. J. Phys. Chem. C, 2011, 115:19782.
[45] Tang S P, Wu W F, Fu Z H, Zou S, Liu Y C, Zhao H H, Kirk S R, Yin D L. ChemCatChem, 2015, 7:2637.
[46] Lu H Y, Ren W Z, Liu P F, Qi S X, Wang W H, Feng Y M, Sun F X, Wang Y W. Appl. Catal. A-Gen., 2012, 441:136.
[47] Maksimchuk N V, Kovalenko K A, Fedin V P, Kholdeeva O A. Chem. Commun., 2012, 48:6812.
[48] Long J L, Wang L M, Gao X F, Bai C H, Jiang H F, Li Y W. Chem. Commun., 2012, 48:12109.
[49] Silva A R, Mourao T, Rocha J. Catal. Today, 2013, 203:81.
[50] Rana S, Jonnalagadda S B. Chemistryselect, 2017, 2:2277.
[51] Martins L M D R D, Carabineiro S A C, Wang J W, Rocha B G M, Maldonado-Hodar F J, Pombeiro A J L D. ChemCatChem, 2017, 9:1211.
[52] Liu X, Conte M, He Q, Knight D W, Murphy D M, Taylor S H, Whiston K, Kiely C J, Hutchings G J. Chem. -Eur. J., 2017, 23:11834.
[53] Xiao Y P, Liu J C, Lin Y T, Lin W J, Fang Y X. J. Alloys Compd., 2017, 698:170.
[54] Martins L M D R S, de Almeida M P, Carabineiro S A C, Figueiredo J L, Pombeiro A J L. ChemCatChem, 2013, 5:3847.
[55] Denicourt-Nowicki A, Lebedeva A, Bellini C, Roucoux A. ChemCatChem, 2016, 8:357.
[56] Yuan Y, Ji H B, Chen Y X, Han Y, Song X F, She Y B, Zhong R G. Org. Process Res. Dev., 2004, 8:418.
[57] Chen Y, She Y B, Xu J, Li Y. Front. Chem. Eng. China, 2007, 1:155.
[58] Li H, She Y B, Wang T. Front. Chem. Sci. Eng., 2012, 6:356.
[59] Wang T, She Y B, Fu H Y, Li H. Catal. Today, 2016, 264:185.
[60] Li H, She Y B, Fu H Y, Cao M J, Wang J, Wang T. Can. J. Chem., 2015, 93:696.
[61] Cao M J, She Y B, Fu H Y, Yu Y M, Li H, Wang T. Mol. Simulat., 2015, 41:262.
[62] Zhu X H, Chen Y Z, Zhang F W, Niu J R, Xie M, Ma J T. RSC Adv., 2014, 4:2509.
[63] Machado K, Mukhopadhyay S, Mishra G S. J. Mol. Catal. A-Chem., 2015, 400:139.
[64] Yuan X, Shan G F, Li L X, Wu J, Luo H A. Catal. Lett., 2015, 145:868.
[65] Mishra G S, Kumar A, Mukhopadhyay S, Tavares P B. Appl. Catal. A-Gen., 2010, 384:136.
[66] Tabor E, Poltowicz J, Pamin K, Basag S, Kubiak W. Polyhedron, 2016, 119:342.
[67] Huang G, Guo C C, Tang S S. J. Mol. Catal. A-Chem., 2007, 261:125.
[68] Fu B, Yu H C, Huang J W, Zhao P, Liu J, Ji L N. J. Mol. Catal. A-Chem., 2009, 298:74.
[69] Huang G, Liu S Y, Guo Y A, Wang A P, Luo J, Cai C C. Appl. Catal. A-Gen., 2009, 358:173.
[70] Huang G, Li T M, Liu S Y, Fan M G, Jiang Y X, Guo Y A. Appl. Catal. A-Gen., 2009, 371:161.
[71] Huang G, Luo Z C, Hu Y D, Guo Y A, Jiang Y X, Wei S J. Chem. Eng. J., 2012, 195:165.
[72] Fan M G, Luo Z C, Huang G, Xiang F, Guo Y A, Zhou H. J. Exp. Nanosci., 2013, 8:640.
[73] Huang G, Shen L, Luo Z C, Hu Y D, Guo Y A, Wei S J. Catal. Commun., 2013, 32:108.
[74] Huang G, Wang P, Shen L, Wei Y X, Zeng K, Wei S J. Mater. Sci. Eng. C-Mater., 2015, 49:844.
[75] Xie Y J, Zhang F Y, Liu P L, Hao F, Luo H A. J. Mol. Catal. A-Chem., 2014, 386:95.
[76] Liu Y M, Tsunoyama H, Akita T, Xie S H, Tsukuda T. ACS Catal., 2011, 1:2.
[77] Gui Z Y, Cao W R, Chen L F, Qi Z W. Catal. Commun., 2015, 64:58.
[78] Chen L F, Zhou Y Y, Gui Z Y, Cheng H Y, Qi Z W. J. Mater. Sci., 2017, 52:7186.
[79] Yang X X, Li Y H, Yu H, Gui X C, Wang H J, Huang H Y, Peng F. Aust. J. Chem., 2016, 69:689.
[80] Wang L B, Zhao S T, Liu C X, Li C, Li X, Li H L, Wang Y C, Ma C, Li Z Y, Zeng J. Nano Lett., 2015, 15:2875.
[81] Huang C L, Zhang H Y, Sun Z Y, Liu Z M. Sci. China Chem., 2010, 53:1502.
[82] Qadir M I, Scholten J D, Dupont J. J. Mol. Catal. A-Chem., 2014, 383:225.
[83] Wu M Z, Zhan W C, Guo Y, Wang Y S, Guo Y L, Gong X Q, Wang L, Lu G Z. Chinese J. Catal., 2016, 37:184.
[84] Wu M Z, Zhan W C, Guo Y L, Guo Y, Wang Y S, Wang L, Lu G Z. Appl. Catal. A-Gen., 2016, 523:97.
[85] Unnarkat A P, Sridhar T, Wang H T, Mahajani S, Suresh A K. AIChE J., 2016, 62:4384.
[86] Xiao Z, Zhan W C, Guo Y, Guo Y L, Gong X Q, Lu G Z. Chinese J. Catal., 2016, 37:273.
[87] Fu Y, Zhan W C, Guo Y L, Wang Y Q, Liu X H, Guo Y, Wang Y S, Lu G Z. Micropor. Mesopor. Mater., 2015, 214:101.
[88] Li J, Li X, Shi Y, Mao D S, Lu G Z. Catal. Lett., 2010, 137:180.
[89] Zhou L, Xu J, Chen C, Wang F, Li X. J. Porous. Mater., 2008, 15:7.
[90] Zou G Q, Zhong W Z, Xu Q, Xiao J F, Liu C, Li Y Q, Mao L Q, Kirk S, Yin D L. Catal. Commun., 2015, 58:46.
[91] Yu H, Peng F, Tan J, Hu X W, Wang H J, Yang J A, Zheng W X. Angew. Chem. Int. Ed., 2011, 50:3978.
[92] Chen K, Chai Z G, Li C, Shi L R, Liu M X, Xie Q, Zhang Y F, Xu D S, Manivannan A, Liu Z F. ACS Nano, 2016, 10:3665.
[93] Wang X, Li Y W. J. Mater. Chem. A, 2016, 4:5247.
[94] Li X H, Chen J S, Wang X C, Sun J H, Antonietti M. J. Am. Chem. Soc., 2011, 133:8074.
[95] Yang X X, Wang H J, Li J, Zheng W X, Xiang R, Tang Z K, Yu H, Peng F. Chem. -Eur. J., 2013, 19:9818.
[96] Shiraishi Y, Sugano Y, Ichikawa S, Hirai T. Catal. Sci. Technol., 2012, 2:400.
[97] Ide Y, Kawamoto N, Bando Y, Hattori H, Sadakane M, Sano T. Chem. Commun., 2013, 49:3652.
[98] Yang D X, Wu T B, Chen C J, Guo W W, Liu H Z, Han B X. Green Chem., 2017, 19:311.
[99] Zhong W Z, Qiao T, Dai J, Mao L Q, Xu Q, Zou G Q, Liu X X, Yin D L, Zhao F P. J. Catal., 2015, 330:208.
[100] Shiraishi Y, Shiota S, Hirakawa H, Tanaka S, Ichikawa S, Hirai T. ACS Catal., 2017, 7:293.
[101] Zhang Y L, Hu L L, Zhu C, Liu J, Huang H, Liu Y, Kang Z H. Catal. Sci. Technol., 2016, 6:7252.
[102] Hayashi Y, Komiya N, Suzuki K, Murahashi S I. Tetrahedron Lett., 2013, 54:2706.
[103] Guha S K, Obora Y, Ishihara D, Matsubara H, Ryu I, Ishii Y. Adv. Synth. Catal., 2008, 350:1323.
[104] Sadiq M, Ali M, Iqbal R, Saeed K, Khan A, Umar M N, Rashid H U. J. Chem. Sci., 2015, 127:1167.
[105] Szymańska A, Nitek W, Oszajca M, ?asocha W, Pamin K, Po?towicz J. Catal. Lett., 2016, 146:998.