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
1. [1]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
2. [2]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
3. [3]
  Zhi Chai , Huashan Huang , Xukai Shi , Yujing Lan , Zhentao Yuan , Hong Yan . Wittig反应的立体选择性. University Chemistry, 2025, 40(8): 192-201. doi: 10.12461/PKU.DXHX202410046
4. [4]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
5. [5]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
6. [6]
  Yongwei ZHANG , Chuang ZHU , Wenbin WU , Yongyong MA , Heng YANG . Efficient hydrogen evolution reaction activity induced by ZnSe@nitrogen doped porous carbon heterojunction. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 650-660. doi: 10.11862/CJIC.20240386
7. [7]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
8. [8]
  Wentao Xu , Xuyan Mo , Yang Zhou , Zuxian Weng , Kunling Mo , Yanhua Wu , Xinlin Jiang , Dan Li , Tangqi Lan , Huan Wen , Fuqin Zheng , Youjun Fan , Wei Chen . Bimetal Leaching Induced Reconstruction of Water Oxidation Electrocatalyst for Enhanced Activity and Stability. Acta Physico-Chimica Sinica, 2024, 40(8): 2308003-0. doi: 10.3866/PKU.WHXB202308003
9. [9]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
10. [10]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
11. [11]
  Bolin Sun , Jie Chen , Ling Zhou . 乙烯型卤代烃的亲核取代反应. University Chemistry, 2025, 40(8): 152-157. doi: 10.12461/PKU.DXHX202410032
12. [12]
  Guowen Xing , Guangjian Liu , Le Chang . Five Types of Reactions of Carbonyl Oxonium Intermediates in University Organic Chemistry Teaching. University Chemistry, 2025, 40(4): 282-290. doi: 10.12461/PKU.DXHX202407058
13. [13]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
14. [14]
  Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172
15. [15]
  Zhaoyu Wen , Na Han , Yanguang Li . Recent Progress towards the Production of H₂O₂ by Electrochemical Two-Electron Oxygen Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(2): 2304001-0. doi: 10.3866/PKU.WHXB202304001
16. [16]
  Qian Huang , Zhaowei Li , Jianing Zhao , Ao Yu . Quantum Chemical Calculations Reveal the Details Below the Experimental Phenomenon. University Chemistry, 2024, 39(3): 395-400. doi: 10.3866/PKU.DXHX202309018
17. [17]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
18. [18]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
19. [19]
  Lancanghong Chen , Xingtai Yu , Tianlei Zhao , Qizhi Yao . Exploration of Abnormal Phenomena in Iodometric Copper Quantitation Experiment. University Chemistry, 2025, 40(7): 315-320. doi: 10.12461/PKU.DXHX202408089
20. [20]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . Sulfide Solid Electrolyte Synthesized by Liquid Phase Approach and Application in All-Solid-State Lithium Batteries. Acta Physico-Chimica Sinica, 2025, 41(1): 100004-0. doi: 10.3866/PKU.WHXB202309019

Get Citation

PDF

XML

Metrics

PDF Downloads(27)
Abstract views(3621)
HTML views(653)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142