Homogeneous catalytic systems for selective oxidation of methane: state of the art

Sylwia Balcer

doi:10.1515/pjct-2015-0050

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Homogeneous catalytic systems for selective oxidation of methane: state of the art

Green Sciences

Volume 17 (2015): Issue 3 (September 2015)

By: Sylwia Balcer

Open Access

|Sep 2015

Abstract

Homogeneous catalysts for methane oxidation are of a particular interest from scientific and economic points of view. The results show a great potential for activation and functionalization of CH bonds of unreactive methane. There are still gaps in the knowledge of how to rationally design catalysts for this process. In this paper state-of-the-art. in methane oxidation homogenous catalysis is presented.

References

1. Energy Information Administration, Natural Gas Reserves (2013), http://www.eia.gov/naturalgas/
Search in Google Scholar
2. Michalkiewicz, B., Sreńscek-Nazzal, J. & Ziebro, J. (2009). Optimization of synthesis gas formation in methane reforming with carbon dioxide. Catal. Lett. 129, 142–148. DOI: 10.1007/s10562-008-9797-6.10.1007/s10562-008-9797-6
Search in Google Scholar
3. Rynkowski, J.M., Paryjczak, T. & Lenik, M. (1993). On the nature of oxidic nickel phase in NiO/γ-Al2O3 catalysts. Appl Catal A. 106, 73. DOI: 10.1016/0926-860X(93)80156-K.10.1016/0926-860X(93)80156-K
Search in Google Scholar
4. Ziebro, J., Łukasiewicz, I., Grzmil, B., Borowiak-Palen, E. & Michalkiewicz, B. (2009). Synthesis of nickel nanocapsules and carbon nanotubes via methane CVD. J. Alloys Compd. 485, 695–700. DOI: 10.1016/j.jallcom.2009.06.039.10.1016/j.jallcom.2009.06.039
Search in Google Scholar
5. Ziebro, J., Łukasiewicz, I., Borowiak-Palen, E. & Michalkiewicz, B. (2010). Low temperature growth of carbon nanotubes from methane catalytic decomposition over nickel supported on a zeolite, Nanotechnology 21, 145308. DOI: 10.1088/0957-4484/21/14/145308.10.1088/0957-4484/21/14/14530820234080
Search in Google Scholar
6. Ziebro, J., Skorupińska, B., Kądziołka, G. & Michalkiewicz, B. (2013). Synthesizing multi-walled carbon nanotubes over supported-nickel catalyst. Fuller. Nanotub. Car. N. 21, 333–345. DOI: 10.1080/1536383X.2011.613543.10.1080/1536383X.2011.613543
Search in Google Scholar
7. Michalkiewicz, B. & Majewska, J. (2013). Low temperature one-step synthesis of cobalt nanowires encapsulated in carbon. Appl. Phys. A 111, 1013–1016. DOI: 10.1007/s00339-013-7698-z.10.1007/s00339-013-7698-z
Search in Google Scholar
8. Ziebro, J., Łukasiewicz, I., Borowiak-Palen, E. & Michalkiewicz, B. (2010). Low temperature growth of carbon nanotubes from methane catalytic decomposition over nickel supported on a zeolite. Nanotechnology 21, 145308. DOI: 10.1088/0957-4484/21/14/145308.10.1088/0957-4484/21/14/145308
Search in Google Scholar
9. Sen, A. & Lin, M. (2003). Catalytic partial oxidation of methane to methanol and formaldehyde, Am. Chem. Soc., 48, 2, 827. DOI: 10.1007/s11244-005-2888-3.10.1007/s11244-005-2888-3
Search in Google Scholar
10. Dreisbach, F., Losch, H.W. & Harting, P. (2002). Highest pressure adsorption equilibrium data: measurement with magnetic suspension balance and analysis with a new adsorbent/adsorbate-volume. Adsorption 8, 95. DOI: 10.1023/A:1020431616093.10.1023/A:1020431616093
Search in Google Scholar
11. Srenscek-Nazzal, J., Kaminska, W., Michalkiewicz, B. & Koren, Z.C. (2013). Production, characterization and methane storage potential of KOH-activated carbon from sugarcane molasses, Industrial Crops And Products 47, 153–159. DOI: 10.1016/j.indcrop.2013.03.004.10.1016/j.indcrop.2013.03.004
Search in Google Scholar
12. Azevedo, D.C.S., Cassia, J., Araujo, S., Bastos-Neto, M., Eurico, A., Torres, B. & Jaguaribe E.F. (2007). Microporous activated carbon prepared from coconut shells using chemical activation with zinc chloride. Microporous Mesoporous Mater. Cavalcante C.L. 100, 361–364. DOI: 10.1016/j.micromeso.2006.11.024.10.1016/j.micromeso.2006.11.024
Search in Google Scholar
13. Sreńscek-Nazzal, J. & Michalkiewicz, B. (2011). The simplex optimization for high porous carbons preparation, Pol. J. Chem. Tech. 13(4), 63–70. DOI: 10.2478/v10026-011-0051-4.10.2478/v10026-011-0051-4
Search in Google Scholar
14. Lin, M. & Sen, A. (1992). A highly catalytic system for the direct oxidation of lower alkanes by dioxygen in aqueous medium. A formal heterogeneous analog of alkane monooxygenases, J. Am. Chem. Soc. 114, 7307. DOI: 10.1021/ja00044a059.10.1021/ja00044a059
Search in Google Scholar
15. Hammond, C., Forde, M.M, Rahim, M.H.A., Thetford, A., He, Q., Jenkins, R.L., Dimitratos, N. & Lopez-Sanchez, J.A. (2012). Direct catalytic conversion of methane to methanol in an aqueous medium by using copper-promoted Fe-ZSM-5, Chemistry – A European Journal 18, 49, 15735–15745. DOI: 10.1002/anie.201108706.10.1002/anie.201108706
Search in Google Scholar
16. Gang, X., Birch, H., Zhu, Y., Hjuler, H.A., Bjerrum N. J. (2000). Direct Oxidation of Methane to Methanol by Mercuric Sulfate Catalyst, Journal of Catalysis, 196, 2, 287–292. DOI: 10.1006/jcat.2000.3051.10.1006/jcat.2000.3051
Search in Google Scholar
17. Yamada, Y., Ueda, A., Shioyama, H. & Kobayashi, T. (2003). High – throughput experiments on methane partial oxidations using molecular oxygen over silica doped with various elements, Appl. Catal. A. 254, 45. DOI: 10.1016/S0926-860X(03)00262-X.10.1016/S0926-860X(03)00262-X
Search in Google Scholar
18. Otsuka, K. & Hatano, M. (1987). The catalysts for the synthesis of formaldehyde by partial oxidation of methane, J. Catal. 108, 252. DOI: 10.1016/0021-9517(87)90172-2.10.1016/0021-9517(87)90172-2
Search in Google Scholar
19. Parmaliana, A., Frusteri, F., Mezzapica, A., Scurrel, M. S. & Giordano, N. (1993). Novel high activity catalyst for partial oxidation of methane to formaldehyde, J. Chem. Soc. Chem. Commun. 751. DOI: 10.1039/C39930000751.10.1039/c39930000751
Search in Google Scholar
20. Weng, T. & Wolf, E.E. (1993). Partial oxidation of methane on mo/sn/p silica supported catalysts, Appl. Catal., 96, 383 DOI: 10.1016/0926-860X(90)80024-9.10.1016/0926-860X(90)80024-9
Search in Google Scholar
21. Otsuka, K. & Wang, Y. (2001). Direct conversion of methane into oxygenates, Appl. Catal., 222, 145. DOI: 10.1016/S0926-860X(01)00837-7.10.1016/S0926-860X(01)00837-7
Search in Google Scholar
22. Spencer, N.D. (1988). Partial oxidation of methane to formaldehyde by means of molecular oxygen, J. Catal., 109, 143. DOI: 10.1016/0021-9517(88)90197-2.10.1016/0021-9517(88)90197-2
Search in Google Scholar
23. Otsuka, K., Komatsu, T., Jinno, K., Uragami, Y. & Morikawa, A. (1988). Proceedings of the 9^th International Congress on Catalysis, The Chemical Institute of Canada, Ottawa, 915.
Search in Google Scholar
24. Kastsnas, G.N., Tsigdios, G.A. & Schwank, J. (1988). Selective oxidation of methane over vycor glass, quartz glass and various silica, magnesia and alumina surfaces, Appl. Catal. A., 44, 33–51. DOI: 10.1016/S0166-9834(00)80043-3.10.1016/S0166-9834(00)80043-3
Search in Google Scholar
25. Alptakin, G.O., Herring, A.M., Williamson, D.L., Ohno, T.R. & McCormick, R.L. (1999). Methane Partial Oxidation by Unsupported and Silica Supported Iron Phosphate Catalysts: Influence of Reaction Conditions and Co-Feeding of Water on Activity and Selectivity, J. Catal., 181, 104–112. DOI: 10.1006/jcat.1998.2297.10.1006/jcat.1998.2297
Search in Google Scholar
26. Sinev. M.Y., Setiadi, S. & Otsuka, K. (1993). Selectivity Control by Oxygen Pressure in Methane Oxidation over Phosphate Catalysts, Mendeleev Commun., 10. DOI: 10.1016/S0167-2991(08)63427-8.10.1016/S0167-2991(08)63427-8
Search in Google Scholar
27. Hargreaves, J.S.J., Hutchings, G.J. & Joyner, R.W. (1990). Control of product selectivity in the partial oxidation of Methane, Nature, 348, 428. DOI: 10.1038/348428a0.10.1038/348428a0
Search in Google Scholar
28. Michalkiewicz, B., Srenscek-Nazzal, J., Tabero, P., Grzmil, B. & Narkiewicz, U. (2008). Chemical Papers, 62, 1, 106–113. DOI: 10.2478/s11696-007-0086-4.10.2478/s11696-007-0086-4
Search in Google Scholar
29. Kałucki, K. & Michalkiewicz, B. (2001). The effect of boron and magnesium additives on catalytic perform of Mo-0/Si02 in the partial oxidation of methane, Pol. J. Chem. Tech., 3, 16–19.
Search in Google Scholar
30. Parmaliana, A., Frusteri, F., Arena, F., Mezzapica, A. & Sokolovskii, V. (1998). Synthesis of methyl formate via two-step methane partial oxidation, Catal. Today, 46, 117–125. DOI: 10.1016/S0920-5861(98)00333-2.10.1016/S0920-5861(98)00333-2
Search in Google Scholar
31. Durante, V. & Walker, D. (1990). EP 0393895.
Search in Google Scholar
32. Labinger, J.A. (1995). Methane activation in homogeneous systems, Fuel Process. Technol., 42, 325–338. DOI: 10.1016/0378-3820(94)00107-5.10.1016/0378-3820(94)00107-5
Search in Google Scholar
33. Kaleńczuk, R.J. & Ciarka, A. (2005). Materialy XXXVII Ogolnopolskiego Kolokwium Katalitycznego, 88.
Search in Google Scholar
34. Kudo, H. & Ono, T. (1997). Partial oxidation of CH₄ over ZSM-5 catalysts, Appl. Sci., 121/122, 413–416. DOI: 10.1016/S0169-4332(97)00348-6.10.1016/S0169-4332(97)00348-6
Search in Google Scholar
35. Michalkiewicz, B. (2004). Partial oxidation of methane to formaldehyde and methanol using molecular oxygen over Fe-ZSM-5, Appl. Catal. A, 277, 147–153 DOI: 10.1016/j.apcata.2004.09.005.10.1016/j.apcata.2004.09.005
Search in Google Scholar
36. Michalkiewicz, B. (2005) Kinetics of Partial Methane Oxidation Process over the Fe-ZMS-5 Catalysts, Chem. Pap., 59, 403–408 DOI: 10.1016/j.apcata.2004.09.005.10.1016/j.apcata.2004.09.005
Search in Google Scholar
37. Hunter, N.R., Gesser, H.D., Morton, L.A. & Fung, D.P.C., Prepr. 35 th Can. Chem. Eng. Conf., Calgary 6–9 Oct 1985.
Search in Google Scholar
38. Rytz, D.W. & Baiker, A. (1991). Partial oxidation of methane to methanol in a flow reactor an elevated pressure, Ind. Eng. Chem. Res., 30, 2287–2292. DOI: 10.1021/ie00058a007.10.1021/ie00058a007
Search in Google Scholar
39. Shilov, A.E. & Shul’pin, G.B. (1997). Activation of C-H Bonds by Metal Complexes, Chem. Rev., 97, 2879–2932. DOI:10.1021/cr9411886.10.1021/cr9411886
Search in Google Scholar
40. Fu, G. & Xu, X. Mechanistic Insights into Selective Oxidation of Light Alkanes by Transition Metal Compounds/Complexes. In Computational Organometallic Chemistry; Wiest, O., Wu, Y., Eds.; Springer-Verlag: Berlin Heidelberg, Germany, 2012.10.1007/978-3-642-25258-7_5
Search in Google Scholar
41. Gol’dshleger, N.F., Es’kova, V.V., Shilov, A.E. & Steinman, A.A. (1972). Zh.Fiz. Khim., 46, 1353.
Search in Google Scholar
42. Lin, M., Hogan, T. & Sen, A. (1997). A Highly Catalytic Bimetallic System for the Low-Temperature Selective Oxidation of Methane and Lower Alkane with Dioxygen as the Oxidant, J. Am. Chem. Soc., 119, 6048–6053. DOI: 10.1021/ja964371k.10.1021/ja964371k
Search in Google Scholar
43. Lin, M. & Sen, A. (1996) US 5, 510, 525.
Search in Google Scholar
44. Lin, M., Hogan, T. & Sen, A. (1996). Catalytic Carbon–Carbon and Carbon–Hydrogen Bond Cleavage in Lower Alkanes. Low-Temperature Hydroxylations and Hydroxycarbonylations with Dioxygen as the Oxidant, J. Am. Chem. Soc., 118, 4574–4580. DOI: 10.1021/ja953670r.10.1021/ja953670r
Search in Google Scholar
45. Park, E.D., Choi, S.H. & Lee, J.S. (2000). Characterization of Pd/C and Cu catalysts for the oxidation of methane to a methanol derivative, J. Catal., 194, 1, 33–34. DOI: 10.1006/jcat.2000.2907.10.1006/jcat.2000.2907
Search in Google Scholar
46. Park, E.D., Hwang, Y.S. & Lee, J.S. (2001). Direct conversion of methane into oxygenates by H₂O₂ generated in situ from dihydrogen and dioxygen, Catalysis Com.,187–190, DOI: 10.1016/S1566-7367(01)00030-9.10.1016/S1566-7367(01)00030-9
Search in Google Scholar
47. Ellis, P.E. & Lyons, J.E. (1990), EP 0 471 561.
Search in Google Scholar
48. Ellis, P.E. & Lyons, J.E. (1992), EP 0 532 327.10.1007/978-1-349-09924-5_9
Search in Google Scholar
49. Nizova, G.V., Süss-Fink, G. & Shul’pin, G.B. (1997). Catalytic oxidation of methane to methyl hydroperoxide and other oxygenates under mild conditions, Chem. Commun., 397–398. DOI: 10.1039/A607765J.10.1039/a607765j
Search in Google Scholar
50. Nizova, G.V., Süss-Fink, G., Stanislas, S. & Shul’pin, G.B. (1998). xidations by the reagent O₂–H₂O₂ – vanadate anion – pyrazine-2-carboxylic acid’.: Part 10. Oxygenation of methane in acetonitrile and water, J. Mol. Catal. A. Chem., 130, 1–2, 163–170 DOI: 10.1016/S1381-1169(97)00210-0.10.1016/S1381-1169(97)00210-0
Search in Google Scholar
51. Lee, B-J., Kitsukawa, S., Nakagawa, H., Asakura, S. & Fukuda, K. (1998). The Partial Oxidation of Methane to Methanol with Nitrite and Nitrate Melts, Z. Naturforsch., 679.10.1515/znb-1998-0705
Search in Google Scholar
52. Peng, J. & Deng, Y. (2000). Direct catalytic conversion of methane in molten salt medium system under mild conditions, Appl. Catal. A, 201, 2, 155–157. DOI: 10.1016/S0926-860X(00)00561-5.10.1016/S0926-860X(00)00561-5
Search in Google Scholar
53. Sherman, J.H. (1999). US 5954925.
Search in Google Scholar
54. Stauffer, J.E. (1993). US 5185479.
Search in Google Scholar
55. Seki, Y., Mizuno, N. & Misono, M. (1997). High-yield liquid-phase oxygenation of methane with hydrogen peroxide catalyzed by 12-molybdovanadophosphoric acid catalyst precursor, Appl. Catal. A.,158, 1–2, 47–51. DOI: 10.1016/S0926-860X(97)00177-4.10.1016/S0926-860X(97)00177-4
Search in Google Scholar
56. Seki, Y., Min, J. S., Mizuno, N. & Misono, M. (2000). Reaktion mechanism of oxidation of methane with hydrogen-peroxide catalysed by 1,1 – molybdo – 1 vanadophosphoric acid catalyst precursor, J. Phys. Chem. B.,104, 5940–5944. DOI: 10.1021/jp000406y.10.1021/jp000406y
Search in Google Scholar
57. Periana, R.A., Taube, H. & Evitt, E.R. (1993). US 5, 233, 113.
Search in Google Scholar
58. Periana, R.A., Taube, D.J., Gamble, S., Taube, H., Satoh, T. & Fujii, H. (1998). Platinum Catalysts for the High-Yield Oxidation of Methane to a Methanol Derivative, Science, 280 560–564. DOI: 10.1126/science.280.5363.560.10.1126/science.280.5363.560
Search in Google Scholar
59. Michalkiewicz, B., Kałucki, K. & Sośnicki, J.G. (2003). Catalytic system containing metallic palladium in the process methane partial oxidation, J. Catal., 215, 14–19. DOI: 10.1016/S0021-9517(02)00088-X.10.1016/S0021-9517(02)00088-X
Search in Google Scholar
60. Mukhopadhyay, S. & Bell, A.T. (2003). Direct catalytic sulfonation of methane with SO₂ to methanesulfonic acid (MSA) in the presence of molecular O₂, Chem. Commun, 1590–1591. DOI: 10.1039/B303561A.10.1039/b303561a
Search in Google Scholar
61. Mukhopadhyay, S., Bell, A.T. & Zerella, M. (2005). A High-Yield, Liquid-Phase Approach for the Partial Oxidation of Methane to Methanol using SO₃ as the Oxidant, Adv.Synth. Catal., 347, 1203–1206. DOI: 10.1002/adsc.200404394.10.1002/adsc.200404394
Search in Google Scholar
62. Cheng, J., Li, Z., Haught, M. & Tang, Y. (2006) Direct methane conversion to methanol by ionic liquid-dissolved platinum catalysts, Chem. Commun., 4617–4619. DOI: 10.1039/b610328f.10.1039/b610328f17082861
Search in Google Scholar
63. Periana, R.A., Taube, D.J., Evitt, E.R., Löffler, D.G., Wentrcek, P.R., Voss, G. & Masuda, T. (1993). A Mercury-Catalyzed, High-Yield System for the Oxidation of Methane to Methanol, Science, 259 340–343. DOI: 10.1126/science.259.5093.340.10.1126/science.259.5093.340
Search in Google Scholar
64. Gang, X., Birch, H., Zhu, Y., Hjuler, H.A. & Bjerrum, N.J. (2000). Direct Oxidation of Methane to Methanol by Mercuric Sulfate Catalyst, J. Catal. 196, 2, 287–292. DOI: 10.1006/jcat.2000.3051.10.1006/jcat.2000.3051
Search in Google Scholar
65. Sen, A., Benvenuto, M.A., Lin, M., Hutson, A.C. & Basickes, N. (1994). Activation of Methane and Ethane and Their Selective Oxidation to the Alcohols in Protic Media, J. Am. Chem. Soc. 116, 3, 998–1003 DOI: 10.1021/ja00082a022.10.1021/ja00082a022
Search in Google Scholar
66. Basickes, N., Hogan, T.E. & Sen, A. (1996). Radical-Initiated Functionalization of Methane and Ethane in Fuming Sulfuric Acid, J. Am. Chem. Soc., 118, 51, 13111–13112 DOI: 10.1021/ja9632365.10.1021/ja9632365
Search in Google Scholar
67. Mukhopadhyay, S. & Bell, A.T. (2004). Catalyzed sulfonation of methane to methanesulfonic acid, Journal of Molecular Catalysis, 211,1 – 2, 59–65. DOI: 10.1016/j.molcata.2003.10.015.10.1016/j.molcata.2003.10.015
Search in Google Scholar
68. Fu, G., Xu, X. & Wan, H. (2006). Mechanism of methane oxidation by transition metal oxides: A cluster model study, Catal. Today, 117, 1–3, 133–137. DOI: 10.1016/j.cattod.2006.05.048.10.1016/j.cattod.2006.05.048
Search in Google Scholar
69. Carley A.F., Davies P.R. & Roberts M.W. (2005). Activation of oxygen at metal surfaces, Phil. Trans. R. Soc. A, 363, 829–846. DOI:10.1098/rsta.2004.1544.10.1098/rsta.2004.1544
Search in Google Scholar
70. Catlow, C.R.A., French, S.A., Sokol, A.A. & Thomas, J.M. (2005). Computational approaches to the determination of active site structures and reaction mechanisms in heterogeneous catalysts, Phil. Trans. R. Soc. A, 363, 913–936. DOI:10.1098/rsta.2004.1529.10.1098/rsta.2004.1529
Search in Google Scholar
71. Sun, M., Zhang, J., Putaj, P., Caps, V., Lefebvre, F., Pelletier, J. & Basset, J.M. (2013). Catalytic Oxidation of Light Alkanes (C1–C4) by Heteropoly Compounds, Chem. Rev. 2014, 114, 981–1019. DOI.org/10.1021/cr300302b.
Search in Google Scholar
72. Kao, L.C., Hutson, A.C. & Sen, A. (1991). Low-Temperature, Palladium(I1)-Catalyzed, Solution-Phase Oxidation of Methane to a Methanol Derivative, J. Am. Chem. Soc. 113, 2, 700–701 DOI: 10.1021/ja00002a063.10.1021/ja00002a063
Search in Google Scholar
73. Taylor, Ch.E., Anderson, R.R. & Noceti, R.P. (1997). Activation of methane with organopalladium complexes, Catalysis Today, 35, 4, 407–413. DOI: 10.1016/S0920-5861(96)00213-1.10.1016/S0920-5861(96)00213-1
Search in Google Scholar
74. Michalkiewicz, B. (2003). Methane Conversion to Methanol in Condensed Phase, Kinet. Catal., 44, 6, 801–805. DOI: 10.1023/B:KICA.0000009057.79026.0b.10.1023/B:KICA.0000009057.79026.0b
Search in Google Scholar
75. Michalkiewicz, B. & Kałucki, K. (2003). The Role of Pressure in the Partial Methane Oxidation Process in the Pd-Oleum Environment, Chem. Pap., 57, 6, 393–396.
Search in Google Scholar
76. Michalkiewicz, B. (2006). Methane esterification in oleum, Chem. Pap., 602, 5, 371–374. DOI: 10.2478/s11696-006-0067-z.10.2478/s11696-006-0067-z
Search in Google Scholar
77. Michalkiewicz, B., Ziebro, J. & Tomaszewska, M. (2006). Preliminary investigation of low pressure membrane distillation of methyl bisulphate from its solutions in fuming sulphuric acid combined with hydrolysis to methanol, J. Membrane Sci., 286, 1–2, 223–227. DOI: 10.1016/j.memsci.2006.09.039.10.1016/j.memsci.2006.09.039
Search in Google Scholar
78. Periana, R.A., Mironov, O., Taube, D.J., Bhalla, G. & Jones, C.J. (2003). Catalytic, Oxidative Condensation of CH₄ to CH₃COOH in One Step via CH Activation, Science, 301, 5634, 814–818. DOI: 10.1126/science.1086466.10.1126/science.108646612907796
Search in Google Scholar
79. Michalkiewicz, B. (2006). The kinetics of homogeneous catalytic methane oxidation, Appl. Catal. A, 307, 2, 270–274. DOI: 10.1016/j.apcata.2006.04.006.10.1016/j.apcata.2006.04.006
Search in Google Scholar
80. Michalkiewicz, B. & Kosowski, P. (2007). The selective catalytic oxidation of methane to methyl bisulfate at ambient pressure, Catal. Commun.,8, 12, 1939–1942. DOI: 10.1016/j.catcom.2007.03.014.10.1016/j.catcom.2007.03.014
Search in Google Scholar
81. Gang, X., Zhu, Y., Birch, H., Aage, H., Hjuler, A. & Bjerrum, N. (2004). Iodine as catalyst for the direct oxidation of methane to methyl sulfates in oleum, Appl. Catal. A., 261, 1, 91–98. DOI: 10.1016/j.apcata.2003.10.039.10.1016/j.apcata.2003.10.039
Search in Google Scholar
82. Periana, R.A., Mironov, O., Taube, D.J., Bhalla, G., Gamble, S. (2002). High Yield Conversion of Methane to Methyl bisulfate Catalyzed by Iodine Cations, Chem. Commun., 2376–2377. DOI: 10.1039/B205366G.10.1039/b205366g12430448
Search in Google Scholar
83. Zerella, M., Bell, A.T. (2006). Pt-catalyzed oxidative carbonylation of methane to acetic acid in sulfuric acid, Journal of Molecular Catalysis, 259, 1–2, 296–301. DOI: 10.1016/j.molcata.2006.06.059.10.1016/j.molcata.2006.06.059
Search in Google Scholar
84. Michalkiewicz, B., Jarosińska, M. & Łukasiewicz, I. (2009). Kinetic study on catalytic methane esterification in oleum catalyzed by iodine, Chem. Engineer. J., 154, 1–3, 156–161. DOI: 10.1016/j.cej.2009.03.046.10.1016/j.cej.2009.03.046
Search in Google Scholar
85. Michalkiewicz, B. (2011) Methane oxidation to methylbisulfate in oleum at ambient pressure in the presence of iodine as a catalyst, Appl. Catal. A., 394, 1–2, 266–268. DOI: 10.1016/j.apcata.2011.01.014.10.1016/j.apcata.2011.01.014
Search in Google Scholar
86. Vargaftik, M.N., Stolarov, I.P. & Moiseev, I.L. (1990). Highly selective partial oxidation of methane to methyl trifluoroacetate, J. Chem. Soc., Chem. Commun., 1049–1050 DOI: 10.1039/C39900001049.10.1039/c39900001049
Search in Google Scholar
87. Yamanaka, I., Soma, M. & Otsuka, K. (1995). Oxidation of methane to methanol with oxygen catalyzed by europium trichloride at room-temperature, J.Chem. Soc., Chem. Commun., 2235–2236. DOI: 10.1039/C39950002235.10.1039/c39950002235
Search in Google Scholar
88. Yamanaka, I., Soma, M. & Otsuka, K. (1996). Enhancing effect of titanium (II) for the oxidation of methane with O – 2 by an EuCL3 – Zn –CF3CO2H – catalytic system at 40°, Chem. Lett., 565. DOI: 10.1246/cl.1996.565.10.1246/cl.1996.565
Search in Google Scholar
89. Mukhopadhyay, S. & Bell, A. (2004). Direct sulfonation of methane to methanesulfonic acid by sulfur trioxide catalyzed by cerium(IV) sulfate in the presence of molecular oxygen, Advanced Synthesis & Catalysis, 348, 913–916. DOI: 10.1002/adsc.200404060.10.1002/adsc.200404060
Search in Google Scholar
90. Mukhopadhyay, S. & Bell, A. (2003). Direct liquid-phase sulfonation of methane to methanesulfonic acid by SO₃ in the presence of a metal peroxide, Angew. Chem. Internat. Edition, 42, 9, 1019–1021. DOI: 10.1002/anie.200390260.10.1002/anie.20039026012616554
Search in Google Scholar
91. Mukhopadhyay, S. & Bell, A. (2003) Direct sulfonation of methane at low pressure to methanesulfonic acid in the presence of potassium peroxydiphosphate as the initiator, Organic Process Research & Development, 7, 2, 161–163, DOI: 10.1021/op020079n.10.1021/op020079n
Search in Google Scholar
92. Jones, C.J., Taube, D., Periana, R.A., Nielsen, R.J., Oxgaard, J. & Goddard, W.A. (2004). Selective oxidation of methane to methanol catalyzed, with C-H activation, by homogeneous, cationic gold, Angewandte Chemie, International Edition, 116, 35, 4626–4629. DOI: 10.1002/ange.200461055.10.1002/ange.200461055
Search in Google Scholar
93. Lobree, L.J. & Bell, A.T. (2001). K₂S₂O₈-initiated sulfonation of methane to methanesulfonic acid, Ind. Eng. Chem. Res., 40, 3, 736–742. DOI: 10.1021/ie000725b.10.1021/ie000725b
Search in Google Scholar
94. Periana, R.A., Hashiguchi, B.G., Konnick, M., Bischof, S.M., Gustafson, S.J. Devarajan, D., Gunsalus, N. & Ess, D.H. (2014). Main group compounds selectively oxidize mixtures of methane, ethane, and propane to alcohol esters, Science, 343, 6176, 1232–1237. DOI: 10.1126/science.1249357.10.1126/science.124935724626925
Search in Google Scholar
95. Wang, K.X., Xu, H.F., Li, W.S., Au, C.T. & Zhou, X.P. (2006). The synthesis of acetic acid from methane via oxidative bromination, carbonylation, and hydrolysis, Applied Catalysis A, 304, 10, 168–177. DOI: 10.1016/j.apcata.2006.02.035.10.1016/j.apcata.2006.02.035
Search in Google Scholar
96. Fengbo, L., Guoqing, Y., Fang, Y. & Fengwen, Y. (2008). Bromine-mediated conversion of methane to C1 oxygenates over Zn-MCM-41 supported mercuric oxide, Appl. Catal. A: General 335, 1, 82–87. DOI: 10.1016/j.apcata.2007.11.014.10.1016/j.apcata.2007.11.014
Search in Google Scholar
97. Chan, S.I., Nagababu, P., Yu, S.S.F., Maji, S. & Ramu, R. (2014). Developing an efficient catalyst for controlled oxidation of small alkanes under ambient conditions, Catal. Sci. Technol., 4, 930–935. DOI: 10.1039/C3CY00884C.10.1039/C3CY00884C
Search in Google Scholar
98. Jarosińska, M., Lubkowski, K., Sośnicki, J.G., Michalkiewicz, B. (2008). Application of halogens as catalysts of CH₄ esterification, Catal. Lett., 126, 3–4, 407–412. DOI: 0.1007/s10562-008-9645-8.
Search in Google Scholar
99. Michalkiewicz, B. & Balcer, S. (2012). Bromine catalyst for the methane to methyl bisulfate reaction, Pol. J. Chem. Technol., 14, 4, 19–21. DOI: 10.2478/v10026-012-0096-z.10.2478/v10026-012-0096-z
Search in Google Scholar
100. Couderc, R. & Baratti, J. (1980). Oxidations of hydrocarbons by methane by the yeast Pichia pastoris. Purification and properties of the alcohol oxidase, Adv. Appl. Microbiol., 44, 2279–2289.
Search in Google Scholar
101. Droege, M.W., Satcher, J.H., Reibold, R.A., Weakely’, T.J.R., Chauffe, L. & Watkins, B.E. (1992). Application of coordinating Complexes containing an asymmetric coordinating ligand, 1534.
Search in Google Scholar
102. Woodland, M.P. & Dalton, H.J. (1984). Purification and characterization of component A of the methane monooxygenase from Methylococcus capsulatus (Bath), Biol. Chem., 259, 53–59.
Search in Google Scholar
103. Green, J. & Dalton, H.J. (1985). Protein B of soluble methane monooxygenase from Methylococcus capsulatus (Bath). A novel regulatory protein of enzyme activity, Biol. Chem., 260, 29, 15795–15801.
Search in Google Scholar
104. Woodland, M.P., Patil, D.S., Cammack, R. & Dalton, H. (1986). ESR Studies of protein A of the soluble methane monooxygenase from Methylococcus capsulatus (Bath), Biochim. Biophys. Acta, 873, 237–242.
Search in Google Scholar
105. Fox, B.G., Surerus, K.K., Munck, E. & Lipscomb, J.D.J. (1988). Evidence for a mu-oxo-bridged binuclear iron cluster in the hydroxylase component of methane monooxygenase Mössbauer and EPR studies, J. Biol. Chem., 263, 10553–10556.10.1016/S0021-9258(18)38005-0
Search in Google Scholar
106. Prince, R.C., George, G.N., Savas, J.C., Cramer, S.P., Patel, R.N. (1988). Spectroscopic properties of the hydroxylase of methane monooxygenase, Biochim. Biophys. Acta, 952, 220–229.
Search in Google Scholar
107. DeWitt, J.G., Benhen, J.G., Rosenzweig, A.C., Hedman, B., Green, J., Pilkington, S., Papaefthymiou, G.C., Dalton, H., Hodgson, K.O. & Lippard, S.J.J. (1992). Biomimetic catalysts application of coordinating complexes containing an asymmetric coordinating ligand, Am. Chem. Soc., 113, 9219–9235.10.1021/ja00024a031
Search in Google Scholar
108. Fox, B.G., Froland, W.A., Dege, J.E. & Lipscomb, J.D.J. (1989). Methane monooxygenase from Methylosinus trichosporium OB3b. Purification and properties of a three-component system with a high specific activity from a type II methanotrophs, Biol. Chem., 264, 10023–10033.
Search in Google Scholar
109. Merkx, M., Kopp, D.A., Sazinsky, M.H., Blazyk, J.L., Muller, J. & Lippard, S.J. (2001). Dioxygen Activation and Methane Hydroxylation by Soluble Methane Monooxygenase: A Tale of Two Irons and Three Proteins A list of abbreviations can be found in Section 7, Angew.Chem., Int. Ed., 40, 2782–2807. DOI: 10.1002/1521-3773(20010803)40:153.3.CO;2-G.
Search in Google Scholar
110. Markowska, A. & Michalkiewicz, B. (2009). Biosynthesis of methanol from methane by Methylosinus trichosporium OB3, Chemical Papers, 63, 2, 105–110. DOI: 10.2478/s11696-008-0100-5.10.2478/s11696-008-0100-5
Search in Google Scholar
111. Vanelderen, P., Hadt, R.G., Smeets, P.J., Solomon,, E.I., Schoonheydt R.A. & Sels, B.F. (2011). Cu-ZSM-5: A biomimetic inorganic model for methane oxidation, J. Catal., 284, 2, 157–164. DOI: 10.1016/j.jcat.2011.10.009.10.1016/j.jcat.2011.10.009359394623487537
Search in Google Scholar
112. Chan, S.I., Lu, Y.J., Nagababu, P., Maji, S., Hung, M.Ch., Lee, M.M., Hsu, I.J., Minh, P.D., Lai, J.C.H., Kok, Y.N., Sridevi, R., Steve, S.F. Yu, Michael K. Chan. (2013). Efficient oxidation of methane to methanol by dioxygen mediated by tricopper clusters, Angew. Chem.Int. Ed., 52, 3731–3735. DOI: 10.1002/anie.201209846.10.1002/anie.20120984623418110
Search in Google Scholar
113. Shilov, A.E. & Shteinman, A.A. (2012). Methane hydroxylation: a biomimetic approach, Russ. Chem.Rev., 81, 4, 291. DOI: 10.1070/RC2012v081n04ABEH004271.10.1070/RC2012v081n04ABEH004271
Search in Google Scholar

Articles in this issue

DOI: https://doi.org/10.1515/pjct-2015-0050 | Journal eISSN: 3072-0389

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Language: English

Page range: 52 - 61

Published on: Sep 19, 2015

Published by: West Pomeranian University of Technology, Szczecin

In partnership with: Paradigm Publishing Services

Publication frequency: Volume open

Keywords:

alkane functionalization,

methane,

methanol,

catalytic systems,

homogeneous catalytic systems

Related subjects:

Industrial chemistry,

Biotechnology,

Chemical engineering,

Process engineering

© 2015 Sylwia Balcer, published by West Pomeranian University of Technology, Szczecin
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Volume 17 (2015): Issue 3 (September 2015)