Abstract
An attempt has been made to elucidate the extremely complex chemical changes that take place when gas oils (middle distillates such as high speed diesel) are subjected to liquid phase homogeneous oxidative processing in the presence of the redox couple Co(III)/Co(II). For this purpose dilute solutions of gas oil in wet acetic acid have been treated with air under carefully controlled conditions of temperature, pressure and air flow rate. Reaction products are extracted in chloroform from an ice cold aqueous solution of the reaction mixture. Both instrumental (FTIR) and kinetic analyses endorse each other and thereby prove the sequential nature of the reaction resulting in the formation of diverse products through decomposition of the intermediate hydroperoxides, which are unstable in the presence of the catalytic redox couple Co(III)/Co(II).
References
Hodnett BK. Heterogeneous Catalytic Oxidations. John Wiley & Sons 2000.
Liu Z, Liu Z, Zong Z, Wei X, Wang J, Lee CW. Energy & Fuels 2003; 17: 424. http://dx.doi.org/10.1021/ef020071e
McCutcheon AL, Wilson MA. Energy & Fuels 2003; 17: 929. http://dx.doi.org/10.1021/ef0202788
Wang T, Zhu X. Energy & Fuels 2004; 18: 1569. http://dx.doi.org/10.1021/ef0499123
Boraha D, Baruah MK, Haque I. Fuel Proc Tech 2005; 86: 959. http://dx.doi.org/10.1016/j.fuproc.2004.11.015
Quddus MA, Khan F. Fuel 1990; 69: 509. http://dx.doi.org/10.1016/0016-2361(90)90323-I
Quddus MA, Sarwar SN, Khan F. Pet Sci Tech 2003; 21: 1335. http://dx.doi.org/10.1081/LFT-120018179
Li L, Wang G, Meng X, Xu C, Gao J. Ind Eng Chem Res 2008; 47: 710. http://dx.doi.org/10.1021/ie070781d
Simanzhenkov V, Oballa MC, Kim G. Ind Eng Chem Res 2010; 49: 953. http://dx.doi.org/10.1021/ie900609d
Murugan P, Mani T, Mahinpey N, Asghari K. Fuel Processing Technology 2011; 92: 1056. http://dx.doi.org/10.1016/j.fuproc.2010.12.032
Kumar S, Agrawal KM, Khan HU, Nautiyal SP. Pet Sci Tech 2007; 25: 1367. http://dx.doi.org/10.1080/10916460500528755
Zannikos F, Lois E, Stournas S. Fuel Proc Tech 1995; 42: 35. http://dx.doi.org/10.1016/0378-3820(94)00104-2
Collins FM, Lucy AR, Sharp CJ. Mol Catal A: Chem 1997; 117: 397. http://dx.doi.org/10.1016/S1381-1169(96)00251-8
Yazu K, Yamamoto Y, Furuya T, Miki K, Ukegawa K. Energy & Fuels 2001; 15: 1535. http://dx.doi.org/10.1021/ef0101412
Te M, Fairbridge C, Ring Z. App Catal A: General 2001; 219: 267.
Murata S, Murata K, Kidena K, Nomura M. Energy & Fuels 2004; 18: 116. http://dx.doi.org/10.1021/ef034001z
Naqvi SMD, Khan F. Ind Eng Chem Res 2009; 48: 5642. http://dx.doi.org/10.1021/ie900364w
Naqvi SMD, Kamal MA, Khan F. Ind Eng Chem Res 2010; 49: 7210. http://dx.doi.org/10.1021/ie100327m
Naqvi SMD. Catalytic oxidation of gas oil: Kinetic analyses and simulation, Scholars Press 2012.
Schrauzer GN. Transition Metals in Homogeneous Catalysis, Marcel Dekker 1971.
Parshall GW. Homogeneous Catalysis, second ed.; Wiley: New York 1980.
Parshall GW, Ittel SD. Homogeneous Catalysis: The Applications and Chemistry of Catalysis by Soluble Transition Metal Complexes, Wiley: New York 1992.
Raghavendrachar P, Ramachandran S. Ind Eng Chem Res 1992; 31: 453. http://dx.doi.org/10.1021/ie00002a001
Shilov AE, Shul’pin GB. Chem Rev 1997; 97: 2879. http://dx.doi.org/10.1021/cr9411886
Bhaduri S, Mukesh D. Homogeneous Catalysis: Mechanisms and Industrial Applications, Wiley: New York 2000. http://dx.doi.org/10.1002/0471220388
Crabtree RH. Dalton Trans 2001; 2437. http://dx.doi.org/10.1039/b103147n
Brégeault JM. Dalton Trans 2003; 3289. http://dx.doi.org/10.1039/b303073n
Cole-Hamilton DJ. Science 2003; 299: 1702. http://dx.doi.org/10.1126/science.1081881
Mijs WJ, De Jonge CR, HI. Organic Synthesis by Oxidation with Metal Compounds; Plenum Press 1986. http://dx.doi.org/10.1007/978-1-4613-2109-5
Onopchenko A, Schulz JGD. Electron Transfer with Aliphatic Substrates. Oxidation of Cyclohexane with Cobalt(III) Ions Alone and in the Presence of Oxygen. J Org Chem 1973; 38: 3729. http://dx.doi.org/10.1021/jo00961a016
Heiba EI, Dessau RM, Koehl Jr. WJ. Oxidation by Metal Salts. V. Cobaltic Acetate Oxidation of Alkylbenzenes. J Am Chem Soc 1969; 91: 6830. http://dx.doi.org/10.1021/ja01052a049
Kamiya Y, Kashima M. The Autoxidation of Aromatic Hydrocarbons Catalyzed with Cobaltic Acetate in Acetic Acid Solution: I. The Oxidation of Toluene. J Catal 1972; 25: 326. http://dx.doi.org/10.1016/0021-9517(72)90234-5
Smith JM. Chemical Engineering Kinetics, 3rd ed.; McGraw-Hill 1987.
Hiatt R, Mill T, Mayo FR. J Org Chem 1968; 33: 1416. http://dx.doi.org/10.1021/jo01268a022
Kochi JK, Mains HE. J Org Chem 1965; 30: 1862. http://dx.doi.org/10.1021/jo01017a036
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
Copyright (c) 2015 Syed Mumtaz Danish Naqvi, Muhammad Ashraf Kamal, Syed Mohib Raza Kazmi, Kashif Riaz , Fasihullah Khan