THE STATUS OF SOLID ACID CATALYST ON OLIGOMERIZATION OF LIGHT OLEFINS

Abstract

Abstract: With the continuous optimization of China's refining process and gasoline pool composition, the conversion of C4 olefins into clean gasoline with high octane number by oligomerization reaction has been developed rapidly, with solid acid as most widely used catalyst. The source of raw materials and processing route of olefins were briefly introduced with the applications of various kinds of solid acid catalysts being summarized in this paper, mainly including solid phosphoric acid, acid resin, zeolite, clay, heteropoly acid, sulfonated metal oxide and metal/acid supported catalysts, etc. The mechanism of carbon ion reaction over solid acid catalyst was also summarized. It was found that among these catalysts, zeolites has the advantages of adjustable pore and acidity, easy regeneration, no pollution and high activity, which have more industrial application potentials in the future.

Key words: solid acid catalyst, light olefins oligomerization, carbonium ion mechanism, zeolites

CLC Number:

References

参考文献 [1] Monama W, Mohiuddin E, Thangaraj B, et al. Oligomerization of lower olefins to fuel range hydrocarbons over texturally enhanced ZSM-5 catalyst[J]. Catalysis Today, 2020, 342: 167-177 [2] Malaika A, Rechnia-Gor?cy P, Kot M, et al. Selective and efficient dimerization of isobutene over H3PO4 /activated carbon catalysts[J]. Catalysis Today, 2018, 301: 266-273 [3] 中国石化石油化工科学研究院科研处. 中国石化石油化工科学研究院开发的选择性叠合技术工业应用成功[J]. 石油炼制与化工, 2018, 49(9): 15 [4] Egloff G. Polymer gasoline[J]. Industrial and Engineering Chemistry, 1936, 28(12): 1461-1467 [5] Egloff G, Wilson E. Thermal reactions of gaseous hydrocarbons[J]. Industrial and Engineering Chemistry, 1935, 27(8): 917-933 [6] Ipatieff V N, Schaad R E. Heptenes and heptanes from propylene and butylenes[J]. Industrial and Engineering Chemistry, 1945, 37(4): 362-364 [7] Ipatieff V N, Corson B B, Egloff G. Polymerization, a new source of gasoline[J]. Industrial and Engineering Chemistry, 1935, 27(9): 1077-1081 [8] Chang C D. The New Zealand gas-to-gasoline plant: an engineering tour de force[J]. Catalysis Today, 1992, 13: 103-111 [9] Nicholas C P. Applications of light olefin oligomerization to the production of fuels and chemicals[J]. Applied Catalysis A: General, 2017, 543: 82-97 [10] 何奕工, 舒兴田, 龙军. 正碳离子和相关的反应机理[J]. 石油学报（石油加工）, 2007, 23(4): 1-7 [11] Ipatieff V N. Catalytic polymerization of gaseous olefins by liquid phosphoric acid[J]. Industrial and Engineering Chemistry, 1935, 27(9): 1067-1069 [12] 张然, 李天舒, 张彦,等. FCC汽油降烯烃工艺及催化剂研究进展[J]. 工业催化, 2019, 27(11): 12-19 [13] Dry M E. Present and future applications of the Fischer–Tropsch process[J]. Applied Catalysis A: General, 2004, 276: 1-3 [14] Klerk A d, Leckel D O, Prinsloo N M. Butene oligomerization by phosphoric acid catalysis: separating the effects of temperature and catalyst hydration on product selectivity[J]. Industrial & Engineering Chemistry Research, 2006, 45: 6127-6136 [15] Nicholas C P, Laipert L, Prabhakar S. Oligomerization of light olefins to gasoline: an advanced NMR characterization of liquid products[J]. Industrial & Engineering Chemistry Research, 2016, 55: 9140-9146 [16] Godsmark J S, Mathys G M K, Hamilton P, et al. Oligomerisation of Olefins[P]. US 20110124827 A1, 2011-05-26 [17] Brown S H, Godsmark J S, Mathys G M K. Olefin Oligomerization Process[P]. US008716542B2, 2014-05-06 [18] 李林, 陈允玺. 催化裂化轻汽油醚化技术的工业应用[J]. 炼油技术与工程, 2014, 44(4): 17-20 [19] Honkela M L, Krause A O. Influence of linear butenes in the dimerization of isobutene[J]. Industrial & Engineering Chemistry Research, 2005, 44: 5291-5297 [20] Quann R J, Green L A, Tabak S A, et al. Chemistry of olefin oligomerization over ZSM-5 catalyst[J]. Industrial & Engineering Chemistry Research, 1988, 27: 565-570 [21] Popov A G, Pavlov V S, Ivanova I I. Effect of crystal size on butenes oligomerization over MFI catalysts[J]. Journal of Catalysis, 2016, 335: 155-164 [22] 翟云平, 李明罡, 罗一斌. ZSM-5分子筛催化1-己烯叠合反应的研究[J]. 石油炼制与化工, 2015, 46(9): 7-9 [23] Corma A, Martínez C, Doskocil E. Designing MFI-based catalysts with improved catalyst life for oligomerization to high-quality liquid fuels[J]. Journal of Catalysis, 2013, 300: 183-196 [24] Li C, Du J, Wang H, et al. A hemicellulose modified HZSM-5 and their application in the light olefins oligomerization to high-quality liquid fuels reaction[J]. Catalysis Communications, 2017, 102: 89-92 [25] Mlinar A N, Zimmerman P M, Celik F E, e. al. Effects of Br?nsted-acid site proximity on the oligomerization of propene in H-MFI[J]. Journal of Catalysis, 2012, 288: 65-73 [26] Henry M, Bulut M, Vermandel W, et al. Low temperature conversion of linear C4 olefins with acid ZSM-5 zeolites of homogeneous composition[J]. Applied Catalysis A: General, 2012, 413-414: 62-77 [27] Wilshier K G, Smart P, Western R, et al. Oligomerization of propene over H-ZSM-5 zeolite[J]. Applied Catalysis, 1987, 31: 339-359 [28] Chen C S H, Bridger R F. Shape-selective oligomerization of alkenes to near-linear hydrocarbons by zeolite catalysis[J]. Journal of Catalysis, 1996, 161: 687-693 [29] Borges P, Pinto R R, Lemos M A N D A, et al. Light olefin transformation over ZSM-5 zeolites: a kinetic model for olefin consumption[J]. Applied Catalysis A: General, 2007, 324: 20-29 [30] Bellussi G, Mizia F, Calemma V, et al. Oligomerization of olefins from light cracking naphtha over zeolite-based catalyst for the production of high quality diesel fuel[J]. Microporous and Mesoporous Materials, 2012: 164: 127-134 [31] Schmidt R, Welch M B, Randolph B B. Oligomerization of C5 olefins in light catalytic naphtha[J]. Energy & Fuels, 2008, 22: 1148-1155 [32] Yu Z, Han Y, Zhao L, et al. Intergrown new zeolite beta polymorphs with interconnected 12-ring channels solved by combining electron crystallography and single-crystal X-ray diffraction[J]. Chemistry of Materials, 2012, 24: 3701-3706 [33] Wulfers M J, Lobo R F. Assessment of mass transfer limitations in oligomerization of butene at high pressure on H-beta[J]. Applied Catalysis A: General, 2015, 505: 394-401 [34] Kulkarni A, Kumar A, Goldman A S, et al. Selectivity for dimers in pentene oligomerization over acid zeolites[J]. Catalysis Communications, 2016, 75: 98-102 [35] Martens J A, Ravishankar R, Mishin I E, et al. Tailored alkene oligomerization with H-ZSM-57 zeolite[J]. Angew. Chem. Int. Ed., 2000, 39(23): 4376-4379 [36] Roth W J, Dorset D L, Kennedy G J. Discovery of new MWW family zeolite EMM-10: identification of EMM-10P as the missing MWW precursor with disordered layers[J]. Microporous and Mesoporous Materials, 2011, 142: 168-177 [37] Kojima M, Rautenbach M W, O'Connor C T. Butene oligomerization over ion-exchanged mordenite[J]. Industrial & Engineering Chemistry Research, 1988, 27: 248-252 [38] Kim Y T, Chada J P, Xu Z, et al. Low-temperature oligomerization of 1-butene with H-ferrierite[J]. Journal of Catalysis, 2015, 323: 33-44 [39] Pater J P G, Jacobs P A, Martens J A. Oligomerization of hex-1-ene over acidic aluminosilicate zeolites, MCM-41, and silica-alumina co-gel catalysts: a comparative study[J]. Journal of Catalysis, 1999, 184: 262-267 [40] Nicholas C P, Nemeth L T, Plencner W M, et al. Elucidation of phosphorus interaction in dual component zeolite/matrix catalysts: Selectivity control in olefin oligomerization with MTW/Al2O3[J]. Applied Catalysis A: General, 2017, 536: 75-84 [41] Martens J A, Verrelst W H, Mathys G M, et al. Tailored catalytic propene trimerization over acidic zeolites with tubular pores[J]. Angew. Chem. Int. Ed., 2005, 44: 5687-5690 [42] Pater J P G, Jacobs P A, Martens J A. 1-hexene oligomerization in liquid, vapor, and supercritical phases over beidellite and ultrastable Y zeolite catalysts[J]. Journal of Catalysis, 1998, 179: 477-482 [43] Yadav G D, Doshi N S. Development of a green process for poly-α-olefin based lubricants[J]. Green Chemistry, 2002, 4: 528-540 [44] Occelli M L, Hsu J T, Galya L G. Propylene oligomerization with pillared clays[J]. Journal of molecular Catalysis, 1985, 33: 371-389 [45] Lee J S, Yoon J W, Halligudi S B, et al. Trimerization of isobutene over WOx/ZrO2 catalysts[J]. Applied Catalysis A: General, 2009, 366: 299-303 [46] Zhang J, Ohnishi R, Okuhara T, et al. Preferential oligomerization of isobutene in mixtures of isobutene and 1-butene over 12-tungstosilicic acid supported on silica[J]. Applied Catalysis A: General, 2009, 353: 68-73 [47] Yang S, Liu Z, Meng X. Oligomerization of isobutene catalyzed by iron(III) chloride ionic liquids[J]. Energy & Fuels, 2009, 23: 70-73 [48] Gu Y, Shi F, Deng Y. SO3H-functionalized ionic liquid as efficient, green and reusable acidic catalyst system for oligomerization of olefins[J]. Catalysis Communications, 2003, 4: 597-601 [49] Finiels A, Fajula F, Hulea V. Nickel-based solid catalysts for ethylene oligomerization – a review[J]. Catalysis Science & Technology, 2014, 4: 2412-2426 [50] Andrews J, Bonnifay P. The IFP dimersol process for dimerization of propylene into isohexenes[J]. 1977, 55: 328-340 [51] Nicolaides C P, Scurrell M S, Semano P M. Nickel silica-alumina catalysts for ethene oligomerization—control of the selectivity to 1-alkene products[J]. Applied Catalysis A: General, 2003, 245: 43-53 [52] Krupa S L, Freet C D, Shakur M. Apparatus and process for oligomerizing one or more hydrocarbons[P]. WO 2012/078579 A2, 2010-12-10 [53] Lallemand M, Finiels A, Fajula F, et al. Nature of the active sites in ethylene oligomerization catalyzed by Ni-containing molecular sieves: chemical and IR spectral investigation[J]. Journal of Physical Chemistry C, 2009, 113(47): 20360-20364 [54] Lallemand M, Rusu O A, Dumitriu E, et al. Ni-MCM-36 and Ni-MCM-22 catalysts for the ethylene oligomerization[C]. Zeolites and Related Materials: Trends, Targets, and Challenges Proceedings of 4th International FEZA Conference, 2008. 1139-1142 [55] Martínez A, Arribas M A, Concepción P, et al. New bifunctional Ni–H-beta catalysts for the heterogeneous oligomerization of ethylene[J]. Applied Catalysis A: General, 2013, 467: 509-518 [56] Peng Y, Dong M, Meng X, et al. Light FCC gasoline olefin oligomerization over a magnetic NiSO4/γ-Al2O3 catalyst in a magnetically stabilized bed[J]. AIChE, 2009, 55(3): 717-725 [57] Tzompantzi F, Mantilla A, Angel G D, et al. NiO–W2O3/Al2O3 catalysts for the production of ecological gasoline: effect of both NiO and the preparation method on the isobutene oligomerization selectivity[J]. Catalysis Today, 2009, 143: 132-136