Preparing a modified and promoted homogeneous titanium catalyst for ethylene dimerization to butene-1

Document Type : Original research

Authors

1 Chemical Engineering Department, Iran University of Science and Technology, Tehran, I.R. Iran

2 School of chemical engineering oil and gas Iran University of Science and Technology, Tehran, I.R. Iran

3 Research and Development Department of Shazand Petrochemical Co., Arak, Iran

Abstract

Ethylene dimerization is a significant process among the other petrochemical processes due to the production of alpha olefins as the most widely used industrial intermediate. Titanium tetra butoxide/tetrahydrofuran/triethyl aluminum is the main homogeneous catalyst complex in this process. On the other hand, the formation of polymer or oligomerization side reactions are the salient obstacles in the ethylene dimerization process. The effect of various promoters from the group of halo hydrocarbons, along with different modifiers from the group of esters and silane compounds had been investigated to conquer the barriers mentioned above. The reaction conversion, selectivity, and polymer production were the remarkable parameters that were evaluated to study the components’ impacts. The results indicated that the addition of promoters through reaction with Triethyl aluminum (TEA) (co-catalyst) increased the reaction speed and thus increased the conversion of the reaction to 88.26% and reduced the reaction time to 60 min. Among the promoters, the reaction conversion and selectivity of dichloromethane were 88.26% and 78.45%, higher than that of dibromopropane (48.52% and 39.52%), but a higher amount of polymer was produced by dichloromethane. Moreover, Esters strongly decreased the catalyst activity, resulting in a decrease in the conversion to under 25%. On the other hand, silanes showed a significant effect on the control of the polymer chains in Ziegler-Natta homogeneous catalysts. Dicyclopentyldimethoxysilane (DCPDS) modifier brought about an increase of 1.5% in ethylene conversion and a 6% increase in the 1-butene selectivity. At the same time, the polymer formation also prevented a significant amount so the amount of polymer decreased to about 2.1 mg. DCPDS modifier performed better than the Cyclohexylmethyldimethoxysilane (CHMDS) donor.

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Main Subjects

References

  1. Li F, Liu W (2023) Progress in the catalyst for ethylene/α‐olefin copolymerization at high temperature. Canadian J Chem Eng 101: 4992-5019 [CrossRef]
  2. Alzamly A, Bakiro M, Ahmed SH, Siddig LA, Nguyen HL (2022) Linear α-olefin oligomerization and polymerization catalyzed by metal-organic frameworks. Coord Chem Rev 462: 214522 [CrossRef]
  3. Skupinska J (1991) Oligomerization of. alpha.-olefins to higher oligomers. Chem Rev 91: 613-648 [CrossRef]
  4. Corma A, Iborra S (2006) Oligomerization of alkenes. In: Catalysts for Fine Chemical Synthesis: Microporous and Mesoporous Solid Catalysts, Vol 4, ed: Eric G. Derouane, pp.125-140 [CrossRef]
  5. Antunes BM, Rodrigues AE, Lin Z, Portugal I, Silva CM (2015) Alkenes oligomerization with resin catalysts. Fuel Process Technol 138: 86-99 [CrossRef]
  6. Bekmukhamedov GE, Sukhov AV, Kuchkaev AM, Yakhvarov DG (2020) Ni-based complexes in selective ethylene oligomerization processes. Catalysts 10: 498 [CrossRef]
  7. Chen C, Alalouni MR, Dong X, Cao Z, Cheng Q, Zheng L, Meng L, Guan C, Liu L, Abou-Hamad E, Wang J, , Shi Z, Huang K-W, Cavallo L, Han Y (2021) Highly active heterogeneous catalyst for ethylene dimerization prepared by selectively doping Ni on the surface of a zeolitic imidazolate framework. J Am Chem Soc 143: 7144-7153 [CrossRef]
  8. Egger KW, Cocks AT (1971) Reactions of group III metalalkyls in the gas phase. Part 4.—Kinetics of the homogeneous dimerization of ethylene to 1-butene, catalyzed by gaseous triethylaluminium. Trans Faraday Soc 67: 2638-2644 [CrossRef]
  9. Mahdaviani SH, Parvari M, Soudbar D (2012) Ethylene dimerization by a homogeneous Ti-based three-component catalyst system: process evaluation and optimization of parametric performance. Procedia Eng 42: 616-622 [CrossRef]
  10. Albright LF, Smith CS (1968) Reactions of ethylene with triethyl aluminum: Effect of operating variables and kinetics of reaction. AIChE J 14: 325-320 [CrossRef]
  11. Sivalingam G, Natarajan V, Sarma KR, Parasuveera U (2008) Solubility of ethylene in the presence of hydrogen in process solvents under polymerization conditions. Ind Eng Chem Res 47: 8940-8946 [CrossRef]
  12. Reyhan SB, Alavi SM, Soudbar D (2023) Investigation of catalytic reaction of ethylene dimerization to butene-1 by use of DCPDS as a modifier based on response surface methodology. Heliyon 9: e20481 [CrossRef]
  13. Bigdeli P, Abdouss M, Abedi S (2018) Ti alkoxide-based catalyst system in selective ethylene dimerization: High performance through modifying by alkylsilanes. Chem Eng Commun 205: 102-109 [CrossRef]
  14. Xu Z, Chada JP, Xu L, Zhao D, Rosenfeld DC, Rogers JL, Hermans I, Mavrikakis M, Huber GW (2018) Ethylene dimerization and oligomerization to 1-butene and higher olefins with chromium-promoted cobalt on carbon catalyst. Acs Catal 8: 2488-2497 [CrossRef]
  15. Ren F, Ji P (2020) Recent advances in the application of metal–organic frameworks for polymerization and oligomerization reactions. Catalysts 10: 1441 [CrossRef]
  16. Cordier, A (2019) Oligomerization and polymerization of ethylene by phenoxy-imine titanium catalysts, PhD diss., Université de Lyon [CrossRef]
  17. Masoori M, Nekoomanesh M, Posada-Pérez S, Rashedi R, Bahri-Laleh N (2022) A systematic study on the effect of co-catalysts composition on the performance of Ziegler-Natta catalyst in ethylene/1-butene co-polymerizations. Polymer 261: 125423 [CrossRef]
  18. Mahdaviani SH, Soudbar D, Parvari M (2010) Selective ethylene dimerization toward 1-butene by a new highly efficient catalyst system and determination of its optimum operating conditions in a buchi reactor. Int J Chem Eng Appl 1: 276-281 [CrossRef]
  19. Mahdaviani SH, Parvari M, Soudbar D (2012) Production of 1-butene via selective ethylene dimerization by addition of bromoethane as a new promoter to titanium-based catalyst in the presence of tetrahydropyran modifier and triethylaluminum co-catalyst. Iran J Chem Eng 9: 3-13 [CrossRef]
  20. Henrici‐Olive G, Olivé S (1967) The Active Species in Homogeneous Ziegler‐Natta Catalysts for the Polymerization of Ethylene. Angew Chem, Int Ed Engl 6: 790-798 [CrossRef]
  21. Davis-Gilbert ZW, Wen X, Goodpaster JD, Tonks IA (2018) Mechanism of Ti-catalyzed oxidative nitrene transfer in [2+ 2+ 1] pyrrole synthesis from alkynes and azobenzene. J Am Chem Soc 140: 7267-7281 [CrossRef]
  22. Al-Sa'doun AW (1993) Dimerization of ethylene to butene-1 catalyzed by Ti (OR') 4-AlR3. Appl Catal A-Gen105: 1-40 [CrossRef]
  23. Pillai SM, Tembe GL, Ravindranathan M, Sivaram S (1988) Dimerization of ethylene to 1-butene catalyzed by the titanium alkoxide-trialkylaluminum system. Ind Eng Chem Res 27: 1971-1977 [CrossRef]
  24. Trischler H, Schöfberger W, Paulik C (2013) Influence of Alkylaluminum Co‐catalysts on TiCl4 Transalkylation and Formation of Active Centers C* in Ziegler–Natta Catalysts. Macromolecular React Eng 7: 146-154 [CrossRef]
  25. Belov GP, Matkovsky PE (2010) Processes for the production of higher linear α-olefins. Petrol Chem 50: 296-302 [CrossRef]
  26. Bigdeli P, Abdouss M, Abedi S (2017) Alkoxysilane modification of a T i‐based catalyst system for ethylene dimerization: A step forward in enhancing productivity and selectivity. J Appl Polym Sci 134: 44615 [CrossRef]
  27. Mahdaviani SH, Parvari M, Soudbar D (2011) Effect of two halohydrocarbons as new promoters suitable for titanium-catalyzed ethylene dimerization toward 1-butene. In: Proceedings of the World Congress on Engineering and Computer Science, Vol. 2 [CrossRef]
  28. Stangret J, Gampe T (2005) Hydration of tetrahydrofuran derived from FTIR spectroscopy. J Mol Struct 734: 183-190 [CrossRef]
  29. Albanese JA, Staley DL, Rheingold AL, Burmeister JL (1990) Phosphorus ylides as hard donor ligands: synthesis and characterization of MCl4 (ylide-O)(THF) (M= Ti, Zr, Hf; ylide=(acetylmethylene) triphenylphosphorane, (benzoylmethylene) triphenylphosphorane). Molecular structure of trans-((acetylmethylene) triphenylphosphorane-O) (tetrahydrofuran) tetrachlorotitanium-(IV)-tetrahydrofuran. Inorg Chem 29: 2209-2213 [CrossRef]
  30. Koohestani H, Mansouri H, Pirmoradian A, Hassanabadi M (2020) Investigation of Photocatalytic Efficiency of Supported CuO Nanoparticles on Natural Zeolite Particles in Photodegradation of Methyl Orange. J Nanosci Nanotechnol 20: 5964-5969 [CrossRef]
  31. Koohestani H, Hasanabadi M (2023) Production and Investigation of Natural Zeolite-TiO2/CuO Nanoparticles Composite. Mech Adv Compos Struct 10: 205-210 [CrossRef]
  32. Velasco MJ, Rubio F, Rubio J, Oteo JL (1999) Hydrolysis of titanium tetrabutoxide. Study by FT-IR spectroscopy. Spectroscopy Letters 32: 289-304 [CrossRef]
  33. Esmaile F, Koohestani H, Abdollah-Pour H (2020) Characterization and antibacterial activity of silver nanoparticles green synthesized using Ziziphora clinopodioides extract. Environ. Nanotechnol. Monit 14: 100303 [CrossRef]
  34. Jiang T, Ning Y, Zhang B, Li J, Wang G, Yi J, Huang Q (2006) Preparation of 1-octene by the selective tetramerization of ethylene. J Mol Catal A-Chem 259: 161-165 [CrossRef]
  35. Kashiwa N (1983) Transition Metal Catalyzed Polymerization: Alkenes and Dienes, Harwood, New York, p. 379
  36. Ye J, Jiang B, Wang J, Yang Y, Pu Q (2014) Siloxane‐mediated ethylene oligomerization with iron‐based catalysts: Retarding the polymer formation. J Polym Sci Pol Chem 52: 2748-2759 [CrossRef]

 

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History

  • Receive Date: 07 January 2024
  • Revise Date: 28 February 2024
  • Accept Date: 02 March 2024
  • First Publish Date: 03 March 2024

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