Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

Optimization of Effective Parameters on 1-Hexene Production from Ethylene Using Chromium/tris 2-Ethylhexanoate Catalyst

Document Type : Research Article

Authors
Zahra Mohamadnia 1
Ebrahim Ahmadi 2
Atefeh Sadat Farandpour 2
1 Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Zanjan, I.R. IRAN
2 Department of Chemistry, University of Zanjan, Zanjan, I.R. IRAN
Abstract
Linear alpha-olefins are one of the most important products of the petrochemical industry, which are widely used in the preparation of detergents, lubricants, plasticizers and also as co-monomer in the production of Linear Low-Density PolyEthylene (LLDPE). Ethylene oligomerization, especially ethylene trimerization (1-hexene production), is one of the most important methods used to produce these high-consumption materials, in which different catalysts are used in the presence of ethylene gas. In this regard, ethylene trimerization catalyst based on four-component system {2,5-dimethylpyrrole (DMP)/Cr(III)/Triethyl Aluminum (TEA)/hexachloroethane (HCE)} was prepared with high purity and the prepared catalyst was characterized using different analysis such as FT-IR, UV-Visible, CHNS, and ICP. The effect of ethylene pressure, the molar ratio of Al/Cr, ligand and solvent types and different injection methods on activity and selectivity was studied. Also, with increasing the ethylene pressure, the productivity of 1-hexane increased. The use of hexachloroethane as an accelerator in the presence of n-heptane aliphatic solvent increased the yield of the catalyst. The best way to perform the trimerization reaction was the production of dual catalyst-ligand and cocatalyst-hexachloroethane solutions separately and adding them to the reactor. Ethylene trimerization using this catalytic system at 27 °C, 90 °C, normal heptane solvent and Al/Cr ratio of 40 resulted in selective production of 1-hexene with a yield of 193850 (g L-C6/g Cr.h) and selectivity of 91.8 percent.
Keywords
Alpha Olefin
Ethylene trimerization
Chromium 2-ethylhexanoate
Triethylaluminum
Pyrrole
1-Hexene

Subjects

[1] Stephan P.S., Normen P., Bhaskar R.A., Sven H., Bernd H.M., Anke S., Uwe R., Mohammed H., A Selective Chromium Catalyst System for the Trimerization of Ethene and Its Coordination Chemistry, European Journal of Inorganic Chemistry, 8: 1167-1171 (2010).
[2] Rozhko E., Bavykina A., Osadchii D., Makkee M., Gascon J., Covalent Organic Frameworks as Supports for a Molecular Ni Based Ethylene Oligomerization Catalyst for the Synthesis of Long Chain Olefins, Journal of Catalysis, 345: 270-280 (2017).
[3] Belov G.P., Matkovsky P.E., Processes for the Production of Higher Linear Alpha Oefins, Petroleum Chemistry, 50(4): 283-289 (2009).
[4] Lappin G.R., Nemec L.H., Sauer J.D., Wagner J.D., "Higher Olefins; Kirk-Othmer Encyclopedia of Chemical Technology", John Wiley & Sons, Inc., New York, USA, 17:709-728 (2000).
[5] Kissin Y.V., "Polymers of Higher Olefins. Kirk-Othmer Encyclopedia of Chemical Technology", John Wiley & Sons, Inc., New York (2005).
[6] Elowe P.R., McCann C., Pringle P.G., Spitzmesser S.K., Bercaw J. E., Nitrogen-Linked Diphosphine Ligands with Ethers Attached to Nitrogen for Chromium-Catalyzed Ethylene Tri- and Tetramerizations, Journal of Organometallic, 25(22): 5255-5260 (2006).
[7] Baralt E.J., Carney M.J., Cole J.B., Chevron Chemical Company, Olefin Oligomerization Catalyst and Process Employing and Preparing Same, U.S. Patent 5,780,698 (1998).
[8] عابدی، ص؛ حدادی اصل، و،  پلی­اولفین‌ها، انتشارات شرکت ملی صنایع پتروشیمی، ص. 313  (1390).
[9] N. Syed, SRI Consulting, “Process Economics Program Report 12E, Linear Alpha Olefins December”, (2008).
[10] ممیز, فروغ؛ توفیقی داریان, جعفر؛ علیزاده, علی محمد،   اثر بارگذاری فلزهای سریم و زیرکونیم بر پایه HZSM-5 برای تولید الفین های سبک از نفتا، نشریه شیمی و مهندسی شیمی ایران، (1)33: 37 تا 47 (1393).
[11] Vilms A.I., Babenko I.A., Bezborodov V.A., Ivanov A.V., Belov, G.P., Ethylene Oligomerization over Chromium (III) Complexes with Pyrrole Derivatives, Petroleum Chemistry, 57(3): 244-250 (2017).
[12] Connor D.S., The Procter & Gamble Company, Surfactant Manufacture, U.S. Patent 6,166,262 (2000).
[13] Zahoor M.A., Al-Sherehy F., Olabisi O., Abdillahi M.M., Saeed M.R., Saudi Basic Industries Corporation, Catalyst and Process for Ethylene Oligomerization, U.S. Patent 6,184,428 (2001).
[14] Hedrich L.W., Kresge A.N., Williamson R.C., Chevron Chemical Company, Saturate Reduction in Normal Alpha Olefins Using a Cobalt-Containing Transalkylation Catalyst, U.S. Patent 5,510,556 (1996).
[15] Plaksunov T.K., Belov G.P., Potapov S.S., “Higher Linear α. Olefins and Ethylene Copolymers on Their Basis: Production and Application”, IPCP RAS, Chernogolovk,  (2008).
[16] Britovsek G.J., Cohen S.A., Gibson V.C., Maddox P.J., van Meurs M., Iron‐Catalyzed Polyethylene Chain Growth on Zinc: Linear α‐Olefins with a Poisson Distribution. Angewandte Chemie International Edition, 41(3): 489-491 (2002).
[17] Mohamadnia Z., Ahmadi E., Nekoomanesh Haghighi M., Salehi-Mobarake H., Synthesis and Optimization of Ethylene Trimerization using [bis-(2-dodecylsulfanyl-ethyl)-amine]CrCl3 Catalyst, Catalysis Letters, 141(3): 474–480, (2011).
[18] Mohamadnia Z., Ahmadi E., Nekoomanesh Haghighi M., High Productive Ethylene Trimerization Catalyst Based on CrCl3/SNS Ligands, Catalysis Letters, 141(8), 1191-1198, (2011).
[19] Mohamadnia Z., Ahmadi E., Nekoomanesh Haghighi M., farandpour A., Rezazade Z., Fallahi M., Preparation of LLDPE Through Tandem Ethylene Polymerization Using Chromium and zirconium catalysts, Iranian Polymer Journal, 24(8):621, (2015).
[20] Luo H.K., Li D.G., Li S.,The Effect of Halide and the Coordination Geometry of Chromium Center in Homogeneous Catalyst System for Ethylene Trimerization, Journal of Molecular Catalysis A: Chemical, 221(1):9-17 (2004).
[21] Web of science, 2017
[22] Manyik R. M., Walker W. E., Wilson T. P., Union Carbide Corporation, Continuous Processes for the Production of Ethylene Polymers and Catalysts Suitable Therefor, U.S. Patent 3,300,458 (1967).
[23] Reagan W.K., Phillips Petroleum Company, Process for Olefin Polymerization, E.P. Patent 0,417,477 (1991).
[24] Reagan W.K., Symp. Prepr. Conv. Light Olefins, Div. Pet. Chem., Am. Chem. Soc., 34: 583 (1989).
[25] Tanaka E., Urata H., Oshiki T., Aoshima T., Kawashima R., Iwade S., Nakamura H., Katsuki S., Okanu T., Process for Producing alpha-Olefin Oligomer Compositions, U.S. Patent 5,750,817 (1998).
[26] Araki Y., Nakamura H., Nanba Y., Okano T., Mitsubishi Chemical Corporation, Process for Producing α-Olefin Oligomer, U.S. Patent 5,856,612 (1999).
[27] Dennett J.N., Gillon A.L., Heslop K., Hyett D.J., Fleming J.S., Lloyd-Jones C.E., Orpen A.G., Pringle P.G., Wass D.F., Scutt J.N., Weatherhead R.H., Diphosphine Complexes of Nickel (II) are Efficient Catalysts for the Polymerization and Oligomerization of Ethylene: Steric Activation and Ligand Backbone Effects, Organometallics, 23(26): 6077-6079 (2004).
[28] Wass D.F., Chromium-Catalysed Ethene Trimerisation and Tetramerisation—Breaking the Rules in Olefin Oligomerisation, Dalton Transactions, 8: 816-819 (2007).
[29] Carter A., Cohen S.A., Cooley N.A., Murphy A., Scutt J., Wass D.F., High Activity Ethylene Trimerisation Catalysts Based on Diphosphine Ligands, Chemical Communications, 8: 858-859 (2002).
[30] McGuinness D.S., Wasserscheid P., Keim W., Hu C., Englert U., Dixon J.T., Grove C., Novel Cr-PNP Complexes as Catalysts for the Trimerisation of Ethylene, Chemical Communications, 3: 334-335 (2003).
[31] McGuinness D.S., Wasserscheid P., Keim W., Morgan D., Dixon J.T., Bollmann A., Maumela H., Hess F., Englert U., First Cr(III)−SNS Complexes and Their Use as Highly Efficient Catalysts for the Trimerization of Ethylene to 1-Hexene, Journal of the American Chemical Society, 125(18): 5272-5273 (2003).
[32] Wöhl A., Müller W., Peitz S., Peulecke N., Aluri B.R., Müller B.H., Heller D., Rosenthal U., Al‐Hazmi M.H., Mosa F.M., Influence of Process Parameters on the Reaction Kinetics of the Chromium‐Catalyzed Trimerization of Ethylene, Chemistry-A European Journal, 16(26): 7833-7842 (2010).
[33] Temple C.N., Gambarotta S., Korobkov I., Duchateau R., New Insight Into the Role of the Metal Oxidation State in Controlling the Selectivity of the Cr-(SNS) Ethylene Trimerization Catalyst, Organometallics, 26(18): 4598-4603 (2007).
[34] Albahily K., Shaikh Y., Ahmed Z., Korobkov I., Gambarotta S., Duchateau R., Isolation of a Self-Activating Ethylene Trimerization Catalyst of a Cr-SNS System, Organometallics, 30(15): 4159-4164 (2011).
[35] Luo W., Li A., Liu S., Ye H., Li Z., 2-Benzimidazol-6-pyrazol-pyridine Chromium (III) Trichlorides: Synthesis, Characterization, and Application for Ethylene Oligomerization and Polymerization, Organometallics, 35(17): 3045-3050 (2016).
[36] Freeman J.W., Buster J.L., Knudsen R.D., Phillips Petroleum Company, Olefin production, U.S. Patent 5,856,257 (1999).
[37] Freeman J.W., Ewert W.M., Kreischer B.E., Knudsen R.D., Cowan G.D., Chevron Phillips Chemical Company Lp, Olefin production, U.S. Patent 6,455,648 (2002).
[38] Yang Y., Kim H., Lee J., Paik H., Jang H.G., Roles of Chloro Compound in Homogeneous [Cr (2-ethylhexanoate)3/2,5-dimethylpyrrole/triethylaluminum/chloro compound] Catalyst System for Ethylene Trimerization, Applied Catalysis A: General, 193(1): 29-38 (2000).
[39] Jiang T., Ji R., Chen H., Cao C., Mao G., Ning Y., Effect of Alkylaluminum Activators on Ethylene Trimerization Based on 2,5‐DMP/Cr(III)/TCE Catalyst System, Chinese Journal of Chemistry, 29(6): 1149-1153 (2011).
[40] Briggs J.R., The Selective Trimerization of Ethylene to hex-1-ene,Chemical Communications, 11: 674-675 (1989).
[41] Werner J.R., Grova C., Steynberg J.P., Stark K.B, Huyser J.J., Steynberg P.J., A DFT Study Toward the Mechanism of Chromium-Catalyzed Ethylene Trimerization,Organomettalic, 23: 1207 (2004).
[42] Emrich R., Heinemann O., Jolly P.W., Kruger C., Verhovnik G.P., The Role of Metallacycles in the Chromium-Catalyzed Trimerization of Ethylene, Organometallics, 16(8):1511-1513 (1997).
[43] M. Heravi M., Sadjadi S., Hekmatshoar R., Abdi Oskooie H., Bamoharram F., Keggin-Type Heteropolyacids-Catalyzed One Pot Oxidation-Trimerization of Alcohols into 2,4,6-Trisubstituted-1,3,5-Trioxanes, Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 28(2):131-136 (2009).