Frontiers of Chemical Science and Engineering >
Advances and perspectives in catalysts for liquid-phase oxidation of cyclohexane
Received date: 10 Jan 2012
Accepted date: 20 Apr 2012
Published date: 05 Sep 2012
Copyright
The latest progress and developments in catalysts for the oxidation of cyclohexane are reviewed. Catalytic systems for the oxidation of cyclohexane including metal supported, metal oxides, molecular sieves, metal substituted polyoxometalates, photocatalysts, organocatalysts, Gif systems, metal-organic catalysts and metalloporphyrins are discussed with a particular emphasis on metalloporphyrin catalytic systems. The advantages and disadvantages of these methods are summarized and analyzed. Finally, the development trends in the oxidation technology of cyclohexane are examined.
Key words: cyclohexane; liquid-phase oxidation; catalysis
Hui LI , Yuanbin SHE , Tao WANG . Advances and perspectives in catalysts for liquid-phase oxidation of cyclohexane[J]. Frontiers of Chemical Science and Engineering, 2012 , 6(3) : 356 -368 . DOI: 10.1007/s11705-012-0903-3
1 |
Labinger J A, Bercaw J E. Understanding and exploiting C–H bond activation. Nature, 2002, 417(6888): 507–514
|
2 |
Newhouse T, Baran P S. If C–H bonds could talk: selective C–H bond oxidation. Angewandte Chemie International Edition, 2011, 50(15): 3362–3374
|
3 |
Neuenschwander U, Turra N, Aellig C, Mania P, Hermans I. Understanding selective oxidations. Chimia, 2010, 64(4): 225–230
|
4 |
Jevtic R, Ramachandran P A, Dudukovic M P. Effect of oxygen on cyclohexane oxidation: a stirred tank study. Industrial & Engineering Chemistry Research, 2009, 48(17): 7986–7993
|
5 |
Guha S K, Obora Y, Ishihara D, Matsubara H, Ryu I, Ishii Y. Aerobic oxidation of cyclohexane using N-hydroxyphthalimide bearing fluoroalkyl chains. Advanced Synthesis & Catalysis, 2008, 350(9): 1323–1330
|
6 |
Yuan Y, Ji H B, Chen Y X, Han Y, Song X F, She Y B, Zhong R G. Study on reaction conditions of biomimetic synthesis of adipic acid from cyclohexane by catalytic oxidation with oxygen. Modern Chemical Industry, 2004, 24(6): 40–42 (in Chinese)
|
7 |
Yuan Y, Ji H B, Chen Y X, Han Y, Song X F, She Y B, Zhong R G. Oxidation of cyclohexane to adipic acid using Fe-porphyrin as a biomimetic catalyst. Organic Process Research & Development, 2004, 8(3): 418–420
|
8 |
Borah P, Datta A. Exfoliated VOPO4·2H2O dispersed on alumina as a novel catalyst for the selective oxidation of cyclohexane. Applied Catalysis A: General, 2010, 376(1-2): 19–24
|
9 |
Borah P, Ramesh A, Datta A. Dispersion of VOPO4·2H2O on different supports through exfoliation and their catalytic activity for the selective oxidation of cyclohexane. Catalysis Communications, 2010, 12(2): 110–115
|
10 |
Zhou L P, Xu J, Miao H, Wang F, Li X Q. Catalytic oxidation of cyclohexane to cyclohexanol and cyclohexanone over Co3O4 nanocrystals with molecular oxygen. Applied Catalysis A: General, 2005, 292: 223–228
|
11 |
Yuan W W, Guo Z W, Jin H B. Synthesis of nanostructured iron oxide and its effect on the cyclohexane oxidation reaction. Journal of Beijing University of Chemical Technology, 2008, 35(4): 6–10 (in Chinese)
|
12 |
Tong J, Bo L, Li Z, Lei Z, Xia C. Magnetic CoFe2O4 nanocrystal: a novel and efficient heterogeneous catalyst for aerobic oxidation of cyclohexane. Journal of Molecular Catalysis A Chemical, 2009, 307(1-2): 58–63
|
13 |
Zhou L P, Yang G Y, Zhang W, Sun Z Q, Gao J, Miao H, Chen C, Ma H, Li X Q, Zhang Q H, Wang F, Tong X L, Xu J. Advances and perspectives in catalytic oxidation of hydrocarbons in liquid phase. Progress in Natural Science, 2007, 17(9): 1003–1011
|
14 |
Li L, Ji W J, Au C T. Gold nanoparticles supported on mesoporous silica and their catalytic application. Progress in Chemistry, 2009, 21(9): 1742–1749 (in Chinese)
|
15 |
Zhao R, Ji D, Lv G M, Qian G, Yan L, Wang X L, Suo J S. A highly efficient oxidation of cyclohexane over Au/ZSM-5 molecular sieve catalyst with oxygen as oxidant. Chemical Communications, 2004, (7): 904–905
|
16 |
Lu G M, Zhao R, Qian G, Qi Y X, Wang X L, Suo J S. A highly efficient catalyst Au/MCM-41 for selective oxidation cyclohexane using oxygen. Catalysis Letters, 2004, 97(3-4): 115–118
|
17 |
Gui J Z, Du J L, Liu D, Song L J, Zhang X T, Sun Z L. Synthesis and catalytic properties of Au-SBA-15 mesoporous zeolite. Industrial Catalysis, 2006, 14(5): 56–60 (in Chinese)
|
18 |
Xu L X, He C H, Zhu M Q, Wu K J, Lai Y L. Surface stabilization of gold by sol-gel post-modification of alumina support with silica for cyclohexane oxidation. Catalysis Communications, 2008, 9(5): 816–820
|
19 |
Xu L X, He C H, Zhu M Q, Fang S. A highly active Au/Al2O3 catalyst for cyclohexane oxidation using molecular oxygen. Catalysis Letters, 2007, 114(3-4): 202–205
|
20 |
Xu L X, He C H, Zhu M Q, Wu K J, Lai Y L. Silica-supported gold catalyst modified by doping with titania for cyclohexane oxidation. Catalysis Letters, 2007, 118(3-4): 248–253
|
21 |
Xu L X, He C H, Zhu M Q, Wu K J, Xu Y L, Zhao J. Cyclohexane oxidation over nano gold catalysts supported on zirconia-modified alumina. Journal of Chemical Engineering of Chinese Universities, 2009, 23(2): 309–313 (in Chinese)
|
22 |
Wang J Y, Zhao H, Zhang X J, Liu R J, Hu Y Q. Oxidation of cyclohexane catalyzed by TS-1 in ionic liquid with tert-butyl-hydroperoxide. Chinese Journal of Chemical Engineering, 2008, 16(3): 373–375
|
23 |
Selvam P, Paulose T A P. Transition-metal (Ti, V, Cr, Mn, Fe, Co, Cu) containing ordered nanoporous materials: novel heterogeneous catalysts for selective oxidation reactions. Journal of Nanoscience and Nanotechnology, 2006, 6(6): 1758–1764
|
24 |
Li J, Li X, Shi Y, Mao D, Lu G. Selective oxidation of cyclohexane by oxygen in a solvent-free system over lanthanide-containing AlPO-5. Catalysis Letters, 2010, 137(3-4): 180–189
|
25 |
Arends I, Sheldon R A. Activities and stabilities of heterogeneous catalysts in selective liquid phase oxidations: recent developments. Applied Catalysis A, General, 2001, 212(1-2): 175–187
|
26 |
Sheldon R A, Wallau M, Arends I, Schuchardt U. Heterogeneous catalysts for liquid-phase oxidations: philosophers’ stones or trojan horses? Accounts of Chemical Research, 1998, 31(8): 485–493
|
27 |
Lee J K, Melsheimer J, Berndt S, Mestl G, Schlogl R, Kohler K. Transient responses of the local electronic and geometric structures of vanado-molybdo-phoshate catalysts H3+nPVnMo12-nO40 in selective oxidation. Applied Catalysis A, General, 2001, 214(1): 125–148
|
28 |
Simões M M Q, Conceição C M M, Gamelas J A F, Domingues P M D N, Cavaleiro A M V, Cavaleiro J A S, Ferrer-Correia A J V, Johnstone R A W. Keggin-type polyoxotungstates as catalysts in the oxidation of cyclohexane by dilute aqueous hydrogen peroxide. Journal of Molecular Catalysis A Chemical, 1999, 144(3): 461–468
|
29 |
Jing S B, Guan J Q, Wang Z L, Zhu W C, Wang G J. Application of dawson-type molybdovanadophosphoric heteropolyacid to oxidation of cyclohexane. Journal of Jilin University, 2008, 46(2): 336–340 (Science Edition) (in Chinese)
|
30 |
Maldotti A, Molinari A, Amadelli R. Photocatalysis with organized systems for the oxofunctionalization of hydrocarbons by O2. Chemical Reviews, 2002, 102(10): 3811–3836
|
31 |
Brusa M A, Grela M A. Photon flux and wavelength effects on the selectivity and product yields of the photocatalytic air oxidation of neat cyclohexane on TiO2 particles. Journal of Physical Chemistry B, 2005, 109(5): 1914–1918
|
32 |
Shimizu K, Murata Y, Satsuma A. Dicopper(II)-dioxygen complexes in Y zeolite for selective catalytic oxidation of cyclohexane under photoirradiation. Journal of Physical Chemistry C, 2007, 111(51): 19043–19051
|
33 |
Ishii Y, Sakaguchi S. A new strategy for alkane oxidation with O2 using N-hydroxyphthalimide (NHPI) as a radical catalyst. Catalysis Surveys from Japan, 1999, 3(1): 27–35
|
34 |
Ishii Y, Sakaguchi S, Iwahama T. Innovation of hydrocarbon oxidation with molecular oxygen and related reactions. Advanced Synthesis & Catalysis, 2001, 343(5): 393–427
|
35 |
Sawatari N, Yokota T, Sakaguchi S, Ishii Y. Alkane oxidation with air catalyzed by lipophilic N-hydroxyphthalimides without any solvent. Journal of Organic Chemistry, 2001, 66(23): 7889–7891
|
36 |
Baucherel X, Gonsalvi L, Arends I W C E, Ellwood S, Sheldon R A. Aerobic oxidation of cycloalkanes, alcohols and ethylbenzene catalyzed by the novel carbon radical chain promoter NHS (N-hydroxysaccharin). Advanced Synthesis & Catalysis, 2004, 346(2-3): 286–296
|
37 |
Yang G Y, Zhang Q H, Miao H, Tong X L, Xu J. Selective organocatalytic oxygenation of hydrocarbons by dioxygen using anthraquinones and N-hydroxyphthalimide. Organic Letters, 2005, 7(2): 263–266
|
38 |
Yang G Y, Ma Y F, Xu J. Biomimetic catalytic system driven by electron transfer for selective oxygenation of hydrocarbon. Journal of the American Chemical Society, 2004, 126(34): 10542–10543
|
39 |
Tong X, Xu J, Miao H. Highly efficient and metal-free aerobic hydrocarbons oxidation process by an o-phenanthroline-mediated organocatalytic system. Advanced Synthesis & Catalysis, 2005, 347(15): 1953–1957
|
40 |
Detoni C, Carvalho N M F, Aranda D A G, Louis B, Antunes O A C. Cyclohexane and toluene oxidation catalyzed by 1,10-phenanthroline Cu(II) complexes. Applied Catalysis A, General, 2009, 365(2): 281–286
|
41 |
Ison A, Xu C, Weakley G K, Richardson D E. Catalytic autoxidations using tris-diimine iron(II) coordination complexes. Journal of Molecular Catalysis A Chemical, 2008, 293(1-2): 1–7
|
42 |
Suzuki Y, Harada E, Nakamaru K, Takeda Y, Sano M, Hashimoto K, Miyake T. Direct oxidation of cycloalkanes with molecular oxygen to dicarboxylic acids using isoamyl nitrite. Journal of Molecular Catalysis A Chemical, 2007, 276(1-2): 1–7
|
43 |
Bonnet D, Ireland T, Fache E, Simonato J. Innovative direct synthesis of adipic acid by air oxidation of cyclohexane. Green Chemistry, 2006, 8(6): 556–559
|
44 |
Barton D, Lee K W, Mehl W, Ozbalik N, Zhang L. Functionalization of saturated-hydrocarbons. 17. Reactivity of carbon carbon double-bonds. Tetrahedron, 1990, 46(11): 3753–3768
|
45 |
Sun X L, Jin H. Catalytic oxidation of cyclohexane to cyclohexanone by GoAggII system. Chinese Journal of Synthetic Chemistry, 2008, 16(4): 451–453(in Chinese)
|
46 |
Nayak S, Gamez P, Kozlevcar B, Pevec A, Roubeau O, Dehnen S, Reedijk J. Coordination compounds from the planar tridentate Schiff-base ligand 2-methoxy-6-((quinolin-8-ylimino)methyl)phenol (mqmpH) with several transition metal ions: use of [FeIII(mqmp)(CH3OH)Cl2] in the catalytic oxidation of alkanes and alkenes. Polyhedron, 2010, 29(11): 2291–2296
|
47 |
Hitomi Y, Furukawa S, Higuchi M, Shishido T, Tanaka T. Alkane hydroxylation catalyzed by a series of mononuclear nonheme iron complexes containing 4-nitropyridine ligands. Journal of Molecular Catalysis A Chemical, 2008, 288(1-2): 83–86
|
48 |
Mansuy D. A brief history of the contribution of metalloporphyrin models to cytochrome P-450 chemistry and oxidation catalysis. Comptes Rendus. Chimie, 2007, 10(4-5): 392–413
|
49 |
Bagchi V, Bandyopadhyay D. The porphyrin complex catalyzed dioxygen activation in presence of solid inorganic phosphates and small quantities of t-BuOOH. Polyhedron, 2008, 27(5): 1387–1392
|
50 |
Guo C C, Chu M F, Liu Q, Liu Y, Guo D C, Liu X Q. Effective catalysis of simple metalloporphyrins for cyclohexane oxidation with air in the absence of additives and solvents. Applied Catalysis A, General, 2003, 246(2): 303–309
|
51 |
Haranaka M, Hara A, Ando W, Akasaka T. Oxygen atom transfer from carbonyl oxide to alkane catalyzed by metalloporphyrin. Tetrahedron Letters, 2009, 50(26): 3585–3587
|
52 |
Poltowicz J, Pamin K, Haber J. Influence of manganese tetraarylporphyrins substituents on the selectivity of cycloalkanes oxidation with magnesium monoperoxyphthalate. Journal of Molecular Catalysis A Chemical, 2006, 257(1-2): 154–157
|
53 |
Chen Y X, She Y B, Xu J, Li Y. Studies on QSAR of metalloporphyrin catalysts in the oxidation of cyclohexane to adipic acid. Frontiers of Chemical Engineering in China, 2007, 1(2): 155–161
|
54 |
Hu B Y, Yuan Y J, Xiao J, Guo C C, Liu Q, Tan Z, Li Q H. Rational oxidation of cyclohexane to cyclohexanol, cyclohexanone and adipic acid with air over metalloporphyrin and cobalt salt. Journal of Porphyrins and Phthalocyanines, 2008, 12(1): 27–34
|
55 |
Carvalho Da Silva D, De Freitas-Silva G, Do Nascimento E, Reboucas J S, Barbeira P J S, Dai De Carvalho M E M, Idemori Y M. Spectral, electrochemical, and catalytic properties of a homologous series of manganese porphyrins as cytochrome P450 model: the effect of the degree of β-bromination. Journal of Inorganic Biochemistry, 2008, 102(10): 1932–1941
|
56 |
Rutkowska-Zbik D, Witko M. Following nature-theoretical studies on factors modulating catalytic activity of porphyrins. Journal of Molecular Catalysis A Chemical, 2006, 258(1-2): 376–380
|
57 |
Ma D S, Hu B C, Lu C X. Selective aerobic oxidation of cyclohexane catalyzed by metallodeuteroporphyrin-IX-dimethylester. Catalysis Communications, 2009, 10(6): 781–783
|
58 |
Hu B C, Zhou W Y, Ma D S, Liu Z L. Metallo-deuteroporphyrins as catalysts for the oxidation of cyclohexane with air in the absence of additives and solvents. Catalysis Communications, 2008, 10(1): 83–85
|
59 |
Zhou W Y, Hu B C, Xu S C, Sun C G, Liu Z L. Catalysis of metallo-deuteroporphyrins for cyclohexane oxidation with air. Chemical Journal of Chinese Universities, 2010, 31(4): 723–726 (in Chinese)
|
60 |
Zhou W Y, Hu B C, Liu Z L. Selective oxidation of cyclohexane catalyzed by metallo-deuteroporphyrins in homogeneous solution. Chinese Journal of Applied Chemistry, 2010, 27(4): 424–427 (in Chinese)
|
61 |
Zhang R, Yu W Y, Che C M. Catalytic enantioselective oxidation of aromatic hydrocarbons with D4-symmetric chiral ruthenium porphyrin catalysts. Tetrahedron, Asymmetry, 2005, 16(21): 3520–3526
|
62 |
Monfared H H, Aghapoor V, Ghorbanloo M, Mayer P. Highly selective olefin epoxidation with the bicarbonate activation of hydrogen peroxide in the presence of manganese(III) meso-tetraphenylporphyrin complex: optimization of effective parameters using the Taguchi method. Applied Catalysis A, General, 2010, 372(2): 209–216
|
63 |
Xie J, Wang Y J, Wei Y. Immobilization of manganese tetraphenylporphyrin on Au/SiO2 as new catalyst for cyclohexane oxidation with air. Catalysis Communications, 2009, 11(2): 110–113
|
64 |
Fu B, Yu H C, Huang J W, Zhao P, Liu J, Ji L N. Mn(III) porphyrins immobilized on magnetic polymer nanospheres as biomimetic catalysts hydroxylating cyclohexane with molecular oxygen. Journal of Molecular Catalysis A Chemical, 2009, 298(1-2): 74–80
|
65 |
Cai J H, Huang J W, Zhao P, Ye Y J, Yu H C, Ji L N. Silica-metalloporphyrins hybrid materials: preparation and catalysis to hydroxylate cyclohexane with molecular oxygen. Journal of Sol-Gel Science and Technology, 2009, 50(3): 430–436
|
66 |
Wang X T, Chu M F, Guo C C. Catalysis of manganeseporphyrin supported on imidazole-modified silica gel for cyclohexane oxidation with air. Chemical Journal of Chinese Universities, 2005, 26(1): 64–67(in Chinese)
|
67 |
Liu C X, Liu Q, Guo C C, Tan Z. Preparation and characterization of novel magnetic nanocomposite-bonded metalloporphyrins as biomimetic nanocatalysts. Journal of Porphyrins and Phthalocyanines, 2010, 14(9): 825–831
|
68 |
Liu C X, Liu Q, Guo C C. Synthesis and catalytic abilities of silica-coated Fe3O4 nanoparticle bonded metalloporphyrins with different saturation magnetization. Catalysis Letters, 2010, 138(1-2): 96–103
|
69 |
Machado G S, Castro K, de Lima O J, Nassar E J, Ciuffi K J, Nakagaki S. Aluminosilicate obtained by sol-gel process as support for an anionic iron porphyrin: development of a selective and reusable catalyst for oxidation reactions. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2009, 349(1-3): 162–169
|
70 |
Moghadam M, Mirkhani V, Tangestaninejad S, Mohammdpoor-Baltork I, Kargar H. Silica supported Mn(Br8TPP)Cl and Mn(TPP)Cl as efficient and reusable catalysts for selective hydrocarbon oxidation under various reaction conditions: the effect of substituted bromines on the catalytic activity and reusability. Journal of Molecular Catalysis A Chemical, 2008, 288(1-2): 116–124
|
71 |
Matachowski L, Pamin K, Poltowicz J, Serwicka E M, Jones W, Mokaya R. Oxidation of cyclooctane over metalloporphyrin-exchanged Al, Si-mesoporous molecular sieves of HMS (MMS) type. Applied Catalysis A, General, 2006, 313(1): 106–111
|
72 |
Farzaneh F, Poorkhosravani M, Ghandi M. Utilization of immobilized biomimetic iron complexes within nanoreactors of Al-MCM-41 as cyclohexane oxidation catalyst. Journal of Molecular Catalysis A Chemical, 2009, 308(1-2): 108–113
|
73 |
Raja R, Ratnasamy P. Oxidation of cyclohexane over copper phthalocyanines encapsulated in zeolites. Catalysis Letters, 1997, 48(1-2): 1–10
|
74 |
Ratnasamy P, Srinivas D. Selective oxidations over zeolite- and mesoporous silica-based catalysts: selected examples. Catalysis Today, 2009, 141(1-2): 3–11
|
75 |
Mirkhani V, Moghadam M, Tangestaninejad S, Kargar H. Mn(Br8TPP)Cl supported on poly styrene-bound imidazole: an efficient and reusable catalyst for biomimetic alkene epoxidation and alkane hydroxylation with sodium periodate under various reaction conditions. Applied Catalysis A, General, 2006, 303(2): 221–229
|
76 |
Huang G, Guo C C, Tang S S. Catalysis of cyclohexane oxidation with air using various chitosan-supported metallotetraphenylporphyrin complexes. Journal of Molecular Catalysis A Chemical, 2007, 261(1): 125–130
|
77 |
Tangestaninejad S, Habibi M H, Mirkhani V, Moghadam M. Mn(Br8TPPS) supported on amberlite IRA-400 as a robust and efficient catalyst for alkene epoxidation and alkane hydroxylation. Molecules (Basel, Switzerland), 2002, 7(2): 264–270
|
78 |
Tangestaninejad S, Habib M H, Mirkhani V, Moghadam M. Preparation of an insoluble polymer-supported Mn(III) porphyrin and its use as a new alkene epoxidation and alkane hydroxylation catalyst. Journal of Chemical Research: S, 2001, (10): 444–445
|
79 |
Castro K A D D, Bail A, Groszewicz P B, Machado G S, Schreiner W H, Wypych F, Nakagaki S. New oxidation catalysts based on iron(III) porphyrins immobilized on Mg-Al layered double hydroxides modified with triethanolamine. Applied Catalysis A, General, 2010, 386(1-2): 51–59
|
80 |
Halma M, Castro K A D D, Prevot V, Forano C, Wypych F, Nakagaki S. Immobilization of anionic iron(III) porphyrins into ordered macroporous layered double hydroxides and investigation of catalytic activity in oxidation reactions. Journal of Molecular Catalysis A Chemical, 2009, 310(1-2): 42–50
|
81 |
Huang G, Liu S Y, Guo Y A, Wang A P, Luo J, Cai C C. Immobilization of manganese tetraphenylporphyrin on boehmite and its catalysis for aerobic oxidation of cyclohexane. Applied Catalysis A, General, 2009, 358(2): 173–179
|
82 |
Guo C C, Xu J B, Long M J, Huang Z M, Liang B X. Study on catalysis of sepiolite-supported metalloporphyrins for cyclohexane oxidation with PhIO. Journal of Hunan University, 1999, 26(3): 18–21 (Natural Sciences Edition) (in Chinese)
|
83 |
Lyons J E, Ellis P E, Myers H K. Halogenated metalloporphyrin complexes as catalysts for selective reactions of acyclic alkanes with molecular oxygen. Journal of Catalysis, 1995, 155(1): 59–73
|
84 |
Guo C C, Liu X Q, Liu Q, Liu Y, Chu M F, Lin W Y. First industrial-scale biomimetic oxidation of hydrocarbon with air over metalloporphyrins as cytochrome P-450 monooxygenase model and its mechanistic studies. Journal of Porphyrins and Phthalocyanines, 2009, 13(12): 1250–1254
|
85 |
Noack H, Georgiev V, Blomberg M, Siegbahn P, Johansson A J. Theoretical insights into heme-catalyzed oxidation of cyclohexane to adipic acid. Inorganic Chemistry, 2011, 50(4): 1194–1202
|
/
〈 | 〉 |