Citation: Ya-jie LIU, Zhen-hui LIANG, Xing LIU, Li-jing YUAN. Progress of selective ring-opening reaction of decalin[J]. Journal of Fuel Chemistry and Technology, ;2022, 50(5): 576-582. doi: 10.1016/S1872-5813(21)60186-X shu

Progress of selective ring-opening reaction of decalin

Ya-jie LIU ¹ ,
Zhen-hui LIANG ^{2, 3} ,
Xing LIU ^{2, 3} ,
Li-jing YUAN ^2,,

1.
College of Chemistry and Chemical Engineering, Jinzhong University, Jinzhong 030619, China
2.
Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, China
3.
University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Li-jing YUAN, yuanlijing@sxicc.ac.cn
Received Date: 9 October 2021
Revised Date: 7 December 2021
Accepted Date: 7 December 2021
Available Online: 9 June 2022

Figures(7)

As a typical saturated bicyclic compound, decalin is normally used as a probe molecule of saturated cycloalkanes for the mechanism study of selective ring-opening reaction during the hydrogenation of light cycle oil. In this review, the molecular structure and reaction characteristics of cis-decalin and trans-decalin are introduced. The mechanism of the selective ring-opening reaction of decalin based on different catalytic systems is systematically analyzed, including the carbocation mechanism on monofunctional acid catalysts, the hydrogenolysis reaction mechanism on monofunctional metal catalysts, and the bifunctional ring-opening reaction mechanism on acid-metal bifunctional catalysts. In addition, the effect of the process conditions, such as reaction temperature, support acidity and zeolite pore size, on the performance of selective ring-opening reaction of decalin are summarized. Finally, the shortcomings of current research are put forward, and the urgent and deserved research topics are proposed.
- decalin,
- catalyst,
- selective ring opening,
- reaction mechanism
1. [1]
  MCVICKER G B, DAAGE M, TOUVELLE M S, HUDSON C W, KLEIN D P, BAIRD W C, COOK B R, CHEN J G, HANTZER S, VAUGHAN DEW. Selective ring opening of naphthenic molecules[J]. J Catal,2002,210(1):137−148. doi: 10.1006/jcat.2002.3685
2. [2]
  SUN Chen-chen. Study on hydrogenation saturation and selective ring opening of diesel aromatics[D]. Xi'an: Xi'an Shiyou University, 2016.
3. [3]
  WANG Q, FAN H L, WU S X, ZHANG Z F, ZHANG P, HAN B X. Water as an additive to enhance the ring opening of naphthalene[J]. Green Chem,2012,14(4):1152−1158. doi: 10.1039/c2gc16554f
4. [4]
  DO P, ALVAREZ W, RESASCO D. Ring opening of 1, 2- and 1, 3-dimethylcyclohexane on iridium catalysts[J]. J Catal,2006,238(2):477−488. doi: 10.1016/j.jcat.2005.12.021
5. [5]
  MORAES R, THOMAS K, THOMAS S, DONK S V, GRASSO G, GILSON J P, HOUALLA M. Ring opening of decalin and methylcyclohexane over alumina-based monofunctional WO₃/Al₂O₃ and Ir/Al₂O₃ catalysts[J]. J Catal,2012,286:62−77. doi: 10.1016/j.jcat.2011.10.014
6. [6]
  MOSTAD H, RIIS T, ELLESTAD O. Catalytic cracking of naphthenes and naphtheno-aromatics in fixed bed micro reactors[J]. J Catal,1990,1(63):345−364.
7. [7]
  KUBIČKA D, KUMAR N, MÄKI-ARVELA P, TIITTA M, NIEMI V, SALMI T, MURZIN D Y. Ring opening of decalin over zeolites: I. Activity and selectivity of proton-form zeolites[J]. J Catal,2004,222(1):65−79. doi: 10.1016/j.jcat.2003.10.027
8. [8]
  MORAES R, THOMAS K, THOMAS S, DONK S V, GRASSO G, GILSON J P, HOUALLA M. Ring opening of decalin and methylcyclohexane over bifunctional Ir/WO₃/Al₂O₃ catalysts[J]. J Catal,2013,299:30−43. doi: 10.1016/j.jcat.2012.11.017
9. [9]
  KUBIČKA D, KUMAR N, MÄKI-ARVELA P, TIITTA M, NIEMI V, KARHU H, SALMI T, MURZIN D Y. Ring opening of decalin over zeolites: II. Activity and selectivity of platinum-modified zeolites[J]. J Catal,2004,227(2):313−327. doi: 10.1016/j.jcat.2004.07.015
10. [10]
  YUAN L J, GUO S Q, LI Z R, CUI H T, DONG H Y, ZHAO L F, WANG J W. Ring opening of decalin over bifunctional Ni-W carbide/Al₂O₃-USY catalysts and monofunctional acid Ni-W oxide/Al₂O₃-USY[J]. RSC Adv,2017,7(16):9446−9455. doi: 10.1039/C6RA27378E
11. [11]
  SANTIKUNAPORN M, HERRERA J E, JONGPATIWUT S, RESASCO E D, ALVAREZ E W, SUGHRUE E L. Ring opening of decalin and tetralin on HY and Pt/HY zeolite catalysts[J]. J Catal,2004,228(1):100−113. doi: 10.1016/j.jcat.2004.08.030
12. [12]
  SANTANA R, DO P, SANTIKUNAPORN M. Evaluation of different reaction strategies for the improvement of cetane number in diesel fuels[J]. Fuel,2006,85(5/6):643−656. doi: 10.1016/j.fuel.2005.08.028
13. [13]
  GAULT F G. Mechanisms of skeletal isomerization of hydrocarbons on metals[J]. Adv Catal,1981,1(30):1−95.
14. [14]
  KUSTOV L M, FINASHINA E D, AVAEV V I, ERSHOV B G. Decalin ring opening on Pt-Ru/SiO₂ catalysts[J]. Fuel Process Technol,2018,173:270−275. doi: 10.1016/j.fuproc.2018.02.007
15. [15]
  MONTEIRO C A A, COSTA D, ZOTIN J L, CARDOSO D. Effect of metal-acid site balance on hydroconversion of decalin over Pt/Beta zeolite bifunctional catalysts[J]. Fuel,2015,160:71−79. doi: 10.1016/j.fuel.2015.07.054
16. [16]
  KANGAS M, KUBIČKA D, SALMI T, MURZIN D Y. Reaction routes in selective ring opening of naphthenes[J]. Top Catal,2010,53(15/18):1172−1175. doi: 10.1007/s11244-010-9556-y
17. [17]
  D'IPPOLITO S A, PIRAULT-ROY L, ESPECEL C, EPRON F, PIECK L C. Selective ring opening of decalin on Rh-Pd/SiO₂-Al₂O₃ bifunctional systems: Catalytic performance and deactivation[J]. Fuel Process Technol,2018,177:6−15. doi: 10.1016/j.fuproc.2018.04.008
18. [18]
  BENITEZ V M, DE LIMA S P, RANGEL M D C, RUIZ D, REYES P, PIECK C L. Influence of the metallic content on Pt-Ir/Nb₂O₅ catalysts for decalin selective ring opening[J]. Catal Today,2017,289:53−61. doi: 10.1016/j.cattod.2016.10.004
19. [19]
  DI FELICE L, CATHERIN N, PICCOLO L, LAURENTI D, BLANCO E, LECLERC E, GEANTET C, CALEMMA V. Decalin ring opening over NiWS/SiO₂-Al₂O₃ catalysts in the presence of H₂S[J]. Appl Catal A: Gen,2016,512:43−51. doi: 10.1016/j.apcata.2015.12.007
20. [20]
  BLANCO E, DI FELICE L, CATHERIN N, PICCOLO L, LAURENTI D, LORENTZ C, GEANTET C, CALEMMA V. Understanding the mechanisms of decalin hydroprocessing using comprehensive two-dimensional chromatography[J]. Ind Eng Chem Res,2016,55(49):12516−12523. doi: 10.1021/acs.iecr.6b03472
21. [21]
  SUÁREZ N, ARRIBAS M A, MORENO A, MARTINEZ A. High-performing Ir- and Pt-containing catalysts based on mesoporous beta zeolite for the selective ring opening of decalin[J]. Catal Sci Technol,2020,10(4):1073−1085. doi: 10.1039/C9CY01812C
22. [22]
  YANG Hao-tian. Study on the catalyst for selective ring-opening of decalin[D]. Qingdao: China University of Petroleum (East China), 2018.
23. [23]
  SUN Tang-xu. Study on the selective ring opening of decalin [D]. Tianjin: Tianjin University, 2012.
24. [24]
  ZHANG Chuan-chuan, WANG Qing-fa. Influence of acid treatment on the selective ring opening of decalin over Beta zeolite[J]. Chem Ind Eng,2017,34(2):16−20.
25. [25]
  LIU Xin-lin, XU You-hao, CUI Shou-ye. Effect of catalyst particle size distribution on the selectivity of catalytic cracking products[J]. Pet Process Petrochem,2011,2(42):42−46.
26. [26]
  AL-SABAWI M, DE LASA H. Influence of zeolite crystallite size on methyl-cyclohexane catalytic conversion products[J]. Fuel,2012,96:511−523. doi: 10.1016/j.fuel.2012.01.065
27. [27]
  YUAN Shuai,LONG Jun,ZHOU Han,TIAN Hui-ping,ZHAO Yi. Molecular Simulation for the Diffusion Characteristics of Aromatic and Naphthenic Hydrocarbons in the Channel of MF1 and FAU Zeolites[J]. Acta Pet Sin (Pet Process Sect),2011,27(4):508−515.
28. [28]
  SOUSA-AGUIAR E F, MOTA C J A, VALLE M L M, DA SILVA M P, DA SILVA D F. Catalytic cracking of decalin isomers over REHY-zeolites with different crystallite sizes[J]. J Mol Catal A: Chem,1996,104(3):267−271. doi: 10.1016/1381-1169(95)00149-2
29. [29]
  MOSTAD H B, RIIS T U, ELLESTAD O H. Shape selectivity in Y-zeolites: Catalytic cracking of decalin-isomers in fixed bed micro reactors[J]. Appl Catal,1990,58(1):105−117.
30. [30]
  BLANCO E, PICCOLO L, LAURENTI D, DI FELICE LUCA, CATHERIN N, LORENTZ C, GEANTET C, CALEMMA V. Effect of H₂S on the mechanisms of naphthene ring opening and isomerization over Ir/NaY: A comparative study of decalin, perhydroindan and butylcyclohexane hydroconversions[J]. Appl Catal A: Gen,2018,550:274−283. doi: 10.1016/j.apcata.2017.11.020
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