Promoting di-isobutene selectivity over ZnO/ZrO2-SO4 in isobutene oligomerization

doi:10.1016/j.cjche.2020.08.039

中国化学工程学报 ›› 2021, Vol. 38 ›› Issue (10): 165-171.DOI: 10.1016/j.cjche.2020.08.039

• Catalysis, Kinetics and Reaction Engineering • 上一篇下一篇

Promoting di-isobutene selectivity over ZnO/ZrO₂-SO₄ in isobutene oligomerization

Jiyuan Li¹, Mifen Cui¹, Zhuxiu Zhang¹, Xian Chen¹, Qing Liu¹, Zhaoyang Fei¹, Jihai Tang^1,2, Xu Qiao^1,2

1. State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing 210009, China;
2. Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing 210009, China

收稿日期:2020-06-10 修回日期:2020-08-04 出版日期:2021-10-28 发布日期:2021-12-02
通讯作者: Zhuxiu Zhang, Jihai Tang
基金资助:
This work was supported by the National Natural Science Foundation of China (21676141, 21808104), the National Key Research and Development Program of China (2017YFB0307304), the Natural Science Foundation of Jiangsu Province (BK20170989), the Natural Science Foundation of Jiangsu Higher Education Institutions of China (17KJB530005), the Project “333” of Jiangsu Province (BRA2016418) and the Six Major Talent Peak Project of Jiangsu Province (XCL-017).

Promoting di-isobutene selectivity over ZnO/ZrO₂-SO₄ in isobutene oligomerization

Jiyuan Li¹, Mifen Cui¹, Zhuxiu Zhang¹, Xian Chen¹, Qing Liu¹, Zhaoyang Fei¹, Jihai Tang^1,2, Xu Qiao^1,2

1. State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing 210009, China;
2. Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing 210009, China

Received:2020-06-10 Revised:2020-08-04 Online:2021-10-28 Published:2021-12-02
Contact: Zhuxiu Zhang, Jihai Tang
Supported by:
This work was supported by the National Natural Science Foundation of China (21676141, 21808104), the National Key Research and Development Program of China (2017YFB0307304), the Natural Science Foundation of Jiangsu Province (BK20170989), the Natural Science Foundation of Jiangsu Higher Education Institutions of China (17KJB530005), the Project “333” of Jiangsu Province (BRA2016418) and the Six Major Talent Peak Project of Jiangsu Province (XCL-017).

摘要/Abstract

摘要： Isooctane attracts great interest in recent years because of its promising potential as friendly-environmental gasoline, which is obtained by dimerization of isobutene with a hydrogenation step. Herein, a solid acid catalyst sulfated zirconia modified by ZnO was prepared. The oligomerization of isobutene had been investigated over ZrO₂-SO₄ and ZnO(X)/ZrO₂-SO₄ catalyst in order to find efficient catalysts for the production of isobutene oligomers. The presence of ZnO obviously enhanced the dimerization of isobutene and ZnO(X)/ZrO₂-SO₄ exhibited the highest di-isobutene yield of 60%. Kinetic studies showed the higher trimerization-to-dimerization activation energy ratios of ZnO(X)/ZrO₂-SO₄ than those of ZrO₂-SO₄ from 353 to 393 K. In addition, reaction rate of dimerization was higher than trimerization over ZnO(X)/ZrO₂-SO₄. The high L/B ratio manifested the capability to enhance the selectivity of C₈ in isobutene dimerization. Furthermore, ZnO(X)/ZrO₂-SO₄ exhibited stable conversion for the dimerization of isobutene.

关键词: Sulfated zirconia, Zinc oxide, Isobutene, Selectivity, Chemical reaction, Catalysis

Abstract: Isooctane attracts great interest in recent years because of its promising potential as friendly-environmental gasoline, which is obtained by dimerization of isobutene with a hydrogenation step. Herein, a solid acid catalyst sulfated zirconia modified by ZnO was prepared. The oligomerization of isobutene had been investigated over ZrO₂-SO₄ and ZnO(X)/ZrO₂-SO₄ catalyst in order to find efficient catalysts for the production of isobutene oligomers. The presence of ZnO obviously enhanced the dimerization of isobutene and ZnO(X)/ZrO₂-SO₄ exhibited the highest di-isobutene yield of 60%. Kinetic studies showed the higher trimerization-to-dimerization activation energy ratios of ZnO(X)/ZrO₂-SO₄ than those of ZrO₂-SO₄ from 353 to 393 K. In addition, reaction rate of dimerization was higher than trimerization over ZnO(X)/ZrO₂-SO₄. The high L/B ratio manifested the capability to enhance the selectivity of C₈ in isobutene dimerization. Furthermore, ZnO(X)/ZrO₂-SO₄ exhibited stable conversion for the dimerization of isobutene.

Key words: Sulfated zirconia, Zinc oxide, Isobutene, Selectivity, Chemical reaction, Catalysis

Jiyuan Li, Mifen Cui, Zhuxiu Zhang, Xian Chen, Qing Liu, Zhaoyang Fei, Jihai Tang, Xu Qiao. Promoting di-isobutene selectivity over ZnO/ZrO₂-SO₄ in isobutene oligomerization[J]. 中国化学工程学报, 2021, 38(10): 165-171.

参考文献

[1] M. DiGirolamo, M. Lami, M. Marchionna, E. Pescarollo, L. Tagliabue, F. Ancillotti, Liquid-phase etherification/dimerization of isobutene over sulfonic acid resins, Ind. Eng. Chem. Res. 36 (11) (1997) 4452-4458
[2] A. Mantilla, F. Tzompantzi, G. Ferrat, A. Lopez-Ortega, S. Alfaro, R. Gomez, M. Torres, Oligomerization of isobutene on sulfated titania: effect of reaction conditions on selectivity, Catal. Today 107-08 (2005) 707-712
[3] M. Marchionna, M. Di Girolamo, R. Patrini, Light olefins dimerization to high quality gasoline components, Catal. Today 65 (2-4) (2001) 397-403
[4] New York City Market immense CAGR value to be 2.1% by 2026, https://www.gurufocus.com/news/950652Isooctane, 2019.
[5] E. Kocaman, O. Akarcay, N. Baglar, S. Celebi, A. Uzun, Isobutene oligomerization on MCM-41-supported tungstophosphoric acid, Mol. Catal. 457 (2018) 41-50
[6] A. Malaika, P. Rechnia-Goracy, M. Kot, M. Kozlowski, Selective and efficient dimerization of isobutene over H₃PO₄/activated carbon catalysts, Catal. Today 301 (2018) 266-273
[7] H.I. Mahdi, O. Muraza, Conversion of isobutylene to octane-booster compounds after methyl tert-butyl ether phaseout: the role of heterogeneous catalysis, Ind. Eng. Chem. Res. 55 (43) (2016) 11193-11210
[8] L. Tong, L. Chen, Y. Ye, Z. Qi, Kinetic studies on the dimerization of isobutene with Ni/Al₂O₃ as a catalyst for reactive distillation process, Chin. J. Chem. Eng. 23 (3) (2015) 520-527
[9] C.A. Trickett, T.M.O. Popp, J. Su, C. Yan, J. Weisberg, A. Huq, P. Urban, J. Jiang, M.J. Kalmutzki, Q. Liu, Identification of the strong Brönsted acid site in a metal-organic framework solid acid catalyst, Nat. Chem. 11 (2) (2019) 170-176
[10] M.J.D. Mahboub, J.L. Dubois, F. Cavani, M. Rostamizadeh, G.S. Patience, Catalysis for the synthesis of methacrylic acid and methyl methacrylate, Chem. Soc. Rev. 47 (20) (2018) 7703-7738
[11] P. Liu, E. Redekop, X. Gao, W.C. Liu, U. Olsbye, G.A. Somorjai, Oligomerization of light olefins catalyzed by Brönsted-acidic metal-organic framework-808, J. Am. Chem. Soc. 141 (29) (2019) 11557-11564
[12] S. Moon, H.J. Chae, M.B. Park, Oligomerization of light olefins over ZSM-5 and beta zeolite catalysts by modifying textural properties, Appl. Catal. A: Gen. 553 (2018) 15-23
[13] J.H. Coetzee, T.N. Mashapa, N.M. Prinsloo, J.D. Rademan, An improved solid phosphoric acid catalyst for alkene oligomerization in a Fischer-Tropsch refinery, Appl. Catal. A: Gen. 308 (2006) 204-209
[14] K. Hauge, E. Bergene, D. Chen, G.R. Fredriksen, A. Holmen, Oligomerization of isobutene over solid acid catalysts, Catal. Today 100 (3-4) (2005) 463-466
[15] S. Talwalkar, M. Chauhan, P. Aghalayam, Z.W. Qi, K. Sundmacher, S. Mahajani, Kinetic studies on the dimerization of isobutene with ion-exchange resin in the presence of water as a selectivity enhancer, Ind. Eng. Chem. Res. 45 (4) (2006) 1312-1323
[16] J.S. Lee, J.W. Yoon, S.B. Halligudi, J.S. Chang, S.H. Jhung, Trimerization of isobutene over WOx/ZrO₂ catalysts, Appl. Catal. A: Gen. 366 (2) (2009) 299-303
[17] R.S. Kamath, Z.W. Qi, K. Sundmacher, P. Aghalayam, S.M. Mahajani, Process analysis for dimerization of isobutene by reactive distillation, Ind. Eng. Chem. Res. 45 (5) (2006) 1575-1582
[18] B.M. Goortani, A. Gaurav, A. Deshpande, F.T.T. Ng, G.L. Rempel, Production of isooctane from isobutene: energy integration and carbon dioxide abatement via catalytic distillation, Ind. Eng. Chem. Res. 54 (14) (2015) 3570-3581
[19] M.L. Honkela, A. Root, M. Lindblad, A.O.I. Krause, Comparison of ion-exchange resin catalysts in the dimerisation of isobutene, Appl. Catal. A: Gen. 295 (2) (2005) 216-223
[20] X. Yu, Y. Liu, H. Wang, W. Cheng, Y. Wu, S. Zhang, Brøsted acidic pyridinium-based ILs catalyzed the selective dimerization of isobutene: performance and in-situ NMR study, Mol. Catal. (2019) 110636
[21] J. Zhang, R. Ohnishi, T. Okuhara, Y. Kamiya, Preferential oligomerization of isobutene in mixtures of isobutene and 1-butene over 12-tungstosilicic acid supported on silica, Appl. Catal. A: Gen. 353 (1) (2009) 68-73
[22] J. Zhang, M. Kanno, J. Zhang, R. Ohnishi, K. Toriyabe, H. Matsuhashi, Y. Kamiya, Preferential oligomerization of isobutene in a mixture of isobutene and 1-butene over sodium-modified 12-tungstosilicic acid supported on silica, J. Mol. Catal. A: Chem. 326 (1-2) (2010) 107-112
[23] A. Behr, N. Rentmeister, T. Seidensticker, J. Vosberg, S. Peitz, D. Maschmeyer, Highly selective dimerization and trimerization of isobutene to linearly linked products by using nickel catalysts, Chem. - Asian J. 9 (2) (2014) 596-601
[24] H. Wang, X. Meng, G. Zhao, S. Zhang, Isobutane/butene alkylation catalyzed by ionic liquids: a more sustainable process for clean oil production, Green Chem. 19 (6) (2017) 1462-1489
[25] M. Ghashghaee, S. Shirvani, Catalytic transformation of ethylene to propylene and butene over an acidic Ca-incorporated composite nanocatalyst, Appl. Catal. A: Gen. 569 (2019) 20-27
[26] A. Silva, K. Wilson, A.F. Lee, V.C. dos Santos, A.C. Cons Bacilla, K.M. Mantovani, S. Nakagaki, Nb₂O₅/SBA-15 catalyzed propanoic acid esterification, Appl. Catal. B: Environ. 205 (2017) 498-504
[27] F.J. Tzornpantzi, M.E. Manriquez, J.M. Padilla, G. Del Angel, R. Gomez, A. Mantilla, One pot preparation of NiO/ZrO₂ sulfated catalysts and its evaluation for the isobutene oligomerization, Catal. Today 133 (2008) 154-159
[28] C. Temvuttirojn, N. Chuasomboon, T. Numpilai, K. Faungnawakij, M. Chareonpanich, J. Limtrakul, T. Witoon, Development of SO₄^2--ZrO₂ acid catalysts admixed with a CuO-ZnO-ZrO₂ catalyst for CO₂ hydrogenation to dimethyl ether, Fuel 241 (2019) 695-703
[29] C.A. Emeis, Determination of integrated molar extinction coefficients for infrared-absorption bands of pyridine adsorbed on solid acid catalysts, J. Catal. 141 (2) (1993) 347-354
[30] H.J.M. Bosman, A.P. Pijpers, A.W.M.A. Jaspers, An X-ray photoelectron spectroscopy study of the acidity of SiO₂-ZrO₂ mixed oxides, J. Catal. 161 (2) (1996) 551-559
[31] H. Li, J. He, A. Riisager, S. Saravanamurugan, B.A. Song, S. Yang, Acid-base bifunctional zirconium N-alkyltriphosphate nanohybrid for hydrogen transfer of biomass-derived carboxides, ACS Catal. 6 (11) (2016) 7722-7727

Promoting di-isobutene selectivity over ZnO/ZrO₂-SO₄ in isobutene oligomerization

Promoting di-isobutene selectivity over ZnO/ZrO₂-SO₄ in isobutene oligomerization

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