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Progress in Chemistry 2018, Vol. 30 Issue (1): 124-136 DOI: 10.7536/PC171102 Previous Articles   

• Review •

Catalytic Oxidation of Cyclohexane by O2 as an Oxidant

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

  1. College of Chemical Engineering, State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, China
  • Received: Revised: Online: Published:
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No. 21476270, 21306176, 21776259).
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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
Key words: cyclohexane, oxidation, oxygen, cyclohexanol, cyclohexanone

CLC Number: 

[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.
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