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Journal articles on the topic 'Tetrahydrodicyclopentadiene'

Author: Grafiati

Published: 5 June 2025

Last updated: 2 August 2025

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1

Wang, Wenke, Jie Zhao, Dandan Jia, et al. "Highly Efficient Hydroisomerization of Endo-Tetrahydrodicyclopentadiene to Exo-Tetrahydrodicyclopentadiene over Pt/HY." ACS Omega 6, no. 27 (2021): 17173–82. http://dx.doi.org/10.1021/acsomega.1c00212.

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2

Bui Anh Thuc, Nguyen Duc Long, Pham Van Toai, Nguyen Ngoc Hai, and Pham Quang Hieu. "Research on optimization of the synthesis endo-tetrahydrodicyclopentadiene from dicyclopentadiene." Journal of Military Science and Technology, IPE (October 14, 2024): 189–96. http://dx.doi.org/10.54939/1859-1043.j.mst.ipe.2024.189-196.

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Endo-tetrahydrodicyclopentadiene (endo-THDCPD) serves as a crucial precursor in the synthesis of exo-tetrahydrodicyclopentadiene (exo-THDCPD), the primary component of JP-10 , a single-component hydrocarbon fuel utilized for high-performance cruise missiles, rockets, and supersonic aircraft propulsion. Endo-THDCPD was synthesized through the hydrogenation reaction of dicyclopentadiene (DCPD) using a Pd/C catalyst. In this study, optimal conditions for the hydrogenation process have been thoroughly investigated. Specifically, the reaction is carried out in n-hexane solvent at a reaction tempera

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3

Cheng, Sheng-San, Kou-Fu Liou, and Yih-Tsung Lin. "High Energy Fuels I: A Novel Preparation of Exo-Tetrahydrodicyclopentadiene by Isomerization of Endo-Tetrahydrodicyclopentadiene." Journal of the Chinese Chemical Society 33, no. 4 (1986): 335–40. http://dx.doi.org/10.1002/jccs.198600048.

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4

Gasanov, A. H., I. H. Ayyubov, S. S. Aliyev, and E. R. Babayev. "Fuel hydrocarbons based on dicyclopentadiene: a short review." SOCAR Proceedings, no. 3 (September 30, 2024): 98–106. https://doi.org/10.5510/ogp20240300998.

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Dicyclopentadiene (tricyclo[5.2.1.02,6]-deca-3,8-diene) is one of the most important products of petrochemical and organic synthesis and is widely used in various fields of industrial activity. At normal room temperature, it is a clear, light yellow liquid with a pungent odor and a high energy density of 10975 W ∙ h/L. Dicyclopentadiene is produced by steam cracking naphtha and gas oil to ethylene. The C5 fraction of liquid pyrolysis products formed as a by-product of ethylene-propylene production is a key raw material for its production. At the same time, dicyclopentadiene is a key compound i

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5

Kolomitsin, I. V., N. A. Sidorenko, P. A. Krasutskii, A. G. Yurchenko, and A. A. Fokin. "ChemInform Abstract: Oxidative Fragmentation of Tetrahydrodicyclopentadiene Skeleton." ChemInform 31, no. 50 (2000): no. http://dx.doi.org/10.1002/chin.200050043.

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6

Wei, Hui, Yongsheng Guo, Fengjun Yang, Wenjun Fang, and Ruisen Lin. "Densities and Viscosities ofexo-Tetrahydrodicyclopentadiene +n-Butanol andexo-Tetrahydrodicyclopentadiene +n-Pentanol at Temperatures of (293.15 to 313.15) K." Journal of Chemical & Engineering Data 55, no. 2 (2010): 1049–52. http://dx.doi.org/10.1021/je9005129.

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7

Kim, Jinhan, Ji-Yun Kim, Eunseo Park, et al. "Isomerization of Endo-tetrahydrodicyclopentadiene over Y Zeolite Catalysts." Applied Chemistry for Engineering 25, no. 1 (2014): 66–71. http://dx.doi.org/10.14478/ace.2013.1107.

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8

Krasutsky, Pavel A., Igor R. Likhotvorik, Tat'lana V. Dubinina, Vitalii V. Nesterenko, and Maitland Jones. "On the mechanism of nitroxylation of endo-tetrahydrodicyclopentadiene." Tetrahedron Letters 36, no. 18 (1995): 3079–82. http://dx.doi.org/10.1016/0040-4039(95)00468-r.

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9

Park, Sun Hee, Cheong Hoon Kwon, Joongyeon Kim, et al. "Mechanistic Insights into Oxidative Decomposition of exo-Tetrahydrodicyclopentadiene." Journal of Physical Chemistry C 117, no. 31 (2013): 15933–39. http://dx.doi.org/10.1021/jp404730g.

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10

Zarezin, Danil P., Marina A. Rudakova, Victor I. Bykov, and Maxim V. Bermeshev. "Metal chlorides supported on silica as efficient catalysts for selective isomerization of endo-tetrahydrodicyclopentadiene to exo-tetrahydrodicyclopentadiene for JP-10 producing." Fuel 288 (March 2021): 119579. http://dx.doi.org/10.1016/j.fuel.2020.119579.

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11

Park, Sun Hee, Joongyeon Kim, Jeong Hwan Chun, et al. "Metal Effects on the Thermal Decomposition of exo-Tetrahydrodicyclopentadiene." Industrial & Engineering Chemistry Research 52, no. 12 (2013): 4395–400. http://dx.doi.org/10.1021/ie302573n.

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12

Honna, Kosaku, Michio Sugimoto, Nobuaki Shimizu, and Konomu Kurisaki. "CATALYTIC REARRANGEMENT OF TETRAHYDRODICYCLOPENTADIENE TO ADAMANTANE OVER Y-ZEOLITE." Chemistry Letters 15, no. 3 (1986): 315–18. http://dx.doi.org/10.1246/cl.1986.315.

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13

Mi, Ji, Pengfei Jiang, Yitong Dai, et al. "Mechanistic study on oxidative degradation and deposition of exo-tetrahydrodicyclopentadiene." Fuel 317 (June 2022): 123533. http://dx.doi.org/10.1016/j.fuel.2022.123533.

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14

Lucas, Michael, Stephen J. Brotton, Ahreum Min, Michelle L. Pantoya, and Ralf I. Kaiser. "Oxidation of Levitated exo-Tetrahydrodicyclopentadiene Droplets Doped with Aluminum Nanoparticles." Journal of Physical Chemistry Letters 10, no. 19 (2019): 5756–63. http://dx.doi.org/10.1021/acs.jpclett.9b02241.

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15

KRASUTSKII, P. A., I. R. LIKHOTVORIK, A. L. LITVIN, and A. G. YURCHENKO. "ChemInform Abstract: Novel Synthetic Pathway to 2-Substituted endo- Tetrahydrodicyclopentadiene." ChemInform 22, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199137111.

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16

Xing, Enhui, Zhentao Mi, Chengwei Xin, Li Wang, and Xiangwen Zhang. "Endo- to exo-isomerization of tetrahydrodicyclopentadiene catalyzed by commercially available zeolites." Journal of Molecular Catalysis A: Chemical 231, no. 1-2 (2005): 161–67. http://dx.doi.org/10.1016/j.molcata.2005.01.015.

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17

Huang, Ming-Yu, Jung-Chung Wu, Fuh-Sheng Shieu, and Jiang-Jen Lin. "Isomerization of endo-tetrahydrodicyclopentadiene over clay-supported chloroaluminate ionic liquid catalysts." Journal of Molecular Catalysis A: Chemical 315, no. 1 (2010): 69–75. http://dx.doi.org/10.1016/j.molcata.2009.09.002.

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18

Xing, Enhui, Xiangwen Zhang, Li Wang, and Zhentao Mi. "Molecular dimensions of tetrahydrodicyclopentadiene isomers and shape selectivity of zeolitic catalysts." Catalysis Communications 6, no. 11 (2005): 737–41. http://dx.doi.org/10.1016/j.catcom.2005.07.010.

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19

Rijal, Dilip, Vladislav Vasilyev, Yunxia Yang, and Feng Wang. "Insights of Density Functional Theory into JP-10 Tetrahydrodicyclopentadiene Fuel Properties." Processes 13, no. 2 (2025): 543. https://doi.org/10.3390/pr13020543.

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This study aims to investigate the structural, spectroscopic, and electronic properties of the synthetic missile fuel exo- and endo-tetrahydrodicyclopentadiene (THDCPD, JP-10) using density functional theory (DFT). It is to understand the dominance of the liquid exo-isomer (96%) of the jet fuel from the subtle differences between the isomers. The present DFT calculations reveal that the exo-isomer is 15.51 kJ/mol more stable than the endo-isomer, attributed to the flipping of the triangular ΔC8-C10-C9 ring in its norbornane skeleton. Calculated nuclear magnetic resonance (13C-NMR) and infrared

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20

Kirchen, Roger P., Ted S. Sorensen, and Steven M. Whitworth. "A mechanistic study of the carbocation route from tetrahydrodicyclopentadiene to the adamantane ring." Canadian Journal of Chemistry 71, no. 12 (1993): 2016–27. http://dx.doi.org/10.1139/v93-251.

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The energy profile for the transformation of the endo-tetrahydrodicyclopentadienyl cation A into the 1-adamantyl cation R has been probed by means of six separate experiments employing superacid techniques. Of the approximately 14 cations between A and R, required as intermediates for the above transformation, it can be shown that only one of these is capable of direct observation. This cation, the tricyclo[5.2.1.03.8]dec-3-yl (homobrendyl) cation J, is characterized in detail in one of the six experiments. The rate of the rearrangement of J into the 1-adamantyl cation has been measured. Catio

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21

Park, Sun Hee, Cheong Hoon Kwon, Joongyeon Kim, et al. "Thermal Stability Improvement of exo-Tetrahydrodicyclopentadiene by 1,2,3,4-Tetrahydroquinoxaline: Mechanism and Kinetics." Journal of Physical Chemistry C 117, no. 15 (2013): 7399–407. http://dx.doi.org/10.1021/jp3113599.

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22

Park, Sun Hee, Joongyeon Kim, Jeong Hwan Chun, et al. "Mechanistic Insights into Thermal Stability Improvement of exo-Tetrahydrodicyclopentadiene by 1,2,3,4-Tetrahydroquinoline." Industrial & Engineering Chemistry Research 51, no. 46 (2012): 14949–57. http://dx.doi.org/10.1021/ie301199t.

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23

Park, Sun Hee, Cheong Hoon Kwon, Joongyeon Kim, et al. "Thermal Stability and Isomerization Mechanism ofexo-Tetrahydrodicyclopentadiene: Experimental Study and Molecular Modeling." Industrial & Engineering Chemistry Research 49, no. 18 (2010): 8319–24. http://dx.doi.org/10.1021/ie100065m.

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24

Liu, Guozhu, Zhentao Mi, Li Wang, Xiangwen Zhang, and Shuting Zhang. "Hydrogenation of Dicyclopentadiene intoendo-Tetrahydrodicyclopentadiene in Trickle-Bed Reactor: Experiments and Modeling." Industrial & Engineering Chemistry Research 45, no. 26 (2006): 8807–14. http://dx.doi.org/10.1021/ie060660y.

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25

Zhao, Lu, Dengfeng Ye, Yongsheng Guo, and Wenjun Fang. "Density and Viscosity of Ternary Mixture of Cyclopentanol + exo-Tetrahydrodicyclopentadiene + 1,3-Dimethyladamantane." Journal of Chemical & Engineering Data 64, no. 6 (2019): 2558–67. http://dx.doi.org/10.1021/acs.jced.9b00074.

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26

Zhao, Long, Weiye Chen, Huaijiang Su, Jiuzhong Yang, and Ralf I. Kaiser. "A vacuum ultraviolet photoionization study on oxidation of JP-10 (exo-Tetrahydrodicyclopentadiene)." Chemical Physics Letters 754 (September 2020): 137490. http://dx.doi.org/10.1016/j.cplett.2020.137490.

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27

Sun, Cong-ming, and Gang Li. "Vapor-phase isomerization of endo-tetrahydrodicyclopentadiene to its exo isomer over zeolite catalysts." Applied Catalysis A: General 402, no. 1-2 (2011): 196–200. http://dx.doi.org/10.1016/j.apcata.2011.06.008.

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28

Li, Dan, Qian Wu, Li Liu, Meng Guo, and Huiqin Wang. "Density, Viscosity and Volatility of Binary Mixtures of Isopropyl Ether and exo-Tetrahydrodicyclopentadiene." Journal of Solution Chemistry 47, no. 3 (2018): 544–59. http://dx.doi.org/10.1007/s10953-018-0736-x.

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29

Huang, Ming-Yu, Jung-Chung Wu, Fuh Sheng Shieu, and Jiang-Jen Lin. "Isomerization of exo-tetrahydrodicyclopentadiene to adamantane using an acidity-adjustable chloroaluminate ionic liquid." Catalysis Communications 10, no. 13 (2009): 1747–51. http://dx.doi.org/10.1016/j.catcom.2009.05.030.

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30

He, Maogang, Qian Zhang, and Xiangyang Liu. "Fouling formed on SS316L tube surface from thermal oxidative degradation of exo -tetrahydrodicyclopentadiene." Applied Thermal Engineering 118 (May 2017): 464–70. http://dx.doi.org/10.1016/j.applthermaleng.2017.02.118.

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31

Kim, Joongyeon, Dong Hun Hyeon, Sun Hee Park, et al. "Catalytic endothermic reactions of exo-tetrahydrodicyclopentadiene with zeolites and improvement of heat of reactions." Catalysis Today 232 (September 2014): 63–68. http://dx.doi.org/10.1016/j.cattod.2013.10.045.

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32

Zhao, Long, Tao Yang, Ralf I. Kaiser, et al. "A vacuum ultraviolet photoionization study on high-temperature decomposition of JP-10 (exo-tetrahydrodicyclopentadiene)." Physical Chemistry Chemical Physics 19, no. 24 (2017): 15780–807. http://dx.doi.org/10.1039/c7cp01571b.

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33

Wang, Lei, Ji-Jun Zou, Xiangwen Zhang, and Li Wang. "Isomerization of tetrahydrodicyclopentadiene using ionic liquid: Green alternative for Jet Propellant-10 and adamantane." Fuel 91, no. 1 (2012): 164–69. http://dx.doi.org/10.1016/j.fuel.2011.07.038.

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34

Gray, Jake T., Derek Burnett, Matthew D. Sundheim, John R. Izzo, and Su Ha. "Steam Reforming of Tetrahydrodicyclopentadiene over Socketed Nickel Perovskite Catalysts with an Applied Electric Field." Energy Technology 8, no. 7 (2020): 2000172. http://dx.doi.org/10.1002/ente.202000172.

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35

Jiao, Charles Q., Biswa N. Ganguly, and Alan Garscadden. "Mass spectrometry study of decomposition of exo-tetrahydrodicyclopentadiene by low-power, low-pressure rf plasma." Journal of Applied Physics 105, no. 3 (2009): 033305. http://dx.doi.org/10.1063/1.3074103.

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36

Ji, Min, Yiyong Zhou, Qunxing Luo, Sang-Eon Park, and Tianxi Cai. "AlCl3 Supported Catalysts for the Isomerization of <i>Endo</i>-Tetrahydrodicyclopentadiene." Green and Sustainable Chemistry 03, no. 02 (2013): 43–47. http://dx.doi.org/10.4236/gsc.2013.32008.

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37

Khan, Azeem, Venkata Pramod Chodimella, Ankita Sharma, et al. "Conversion of dicyclopentadiene into high energy density fuel exo-tetrahydrodicyclopentadiene: An experimental and computational study." Fuel 334 (February 2023): 126605. http://dx.doi.org/10.1016/j.fuel.2022.126605.

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38

Lucas, Michael, Stephen J. Brotton, Ahreum Min, Connor Woodruff, Michelle L. Pantoya, and Ralf I. Kaiser. "Effects of Size and Prestressing of Aluminum Particles on the Oxidation of Levitated exo-Tetrahydrodicyclopentadiene Droplets." Journal of Physical Chemistry A 124, no. 8 (2020): 1489–507. http://dx.doi.org/10.1021/acs.jpca.9b10697.

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39

Morozov, Alexander N., Alexander M. Mebel, and Ralf I. Kaiser. "A Theoretical Study of Pyrolysis of exo-Tetrahydrodicyclopentadiene and Its Primary and Secondary Unimolecular Decomposition Products." Journal of Physical Chemistry A 122, no. 22 (2018): 4920–34. http://dx.doi.org/10.1021/acs.jpca.8b02934.

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40

Olah, George A., and Omar Farooq. "Chemistry in superacids. 7. Superacid-catalyzed isomerization of endo- to exo-trimethylenenorbornane (tetrahydrodicyclopentadiene) and to adamantane." Journal of Organic Chemistry 51, no. 26 (1986): 5410–13. http://dx.doi.org/10.1021/jo00376a067.

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41

Zhang, Lingling, Yongsheng Guo, Hui Wei, Fengjun Yang, Wenjun Fang, and Ruisen Lin. "Densities and Viscosities of Binary Mixtures ofexo-Tetrahydrodicyclopentadiene withN-Undecane orN-Tetradecane atT= (293.15 to 313.15) K." Journal of Chemical & Engineering Data 55, no. 9 (2010): 4108–13. http://dx.doi.org/10.1021/je100313a.

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42

Brotton, Stephen J., and Ralf I. Kaiser. "Effects of Nitrogen Dioxide on the Oxidation of Levitated exo-Tetrahydrodicyclopentadiene (JP-10) Droplets Doped with Aluminum Nanoparticles." Journal of Physical Chemistry A 125, no. 13 (2021): 2727–42. http://dx.doi.org/10.1021/acs.jpca.0c10155.

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43

Khan, Nizamuddin, A. C. Abhyankar, Tandra Nandi, and N. Eswara Prasad. "Nickel Nanocatalyst Supported Single-Step Hydroconversion of Dicyclopentadiene (DCPD) into High Energy-Density Fuel, Exo-Tetrahydrodicyclopentadiene (Exo-THDCPD)." Journal of Nanoscience and Nanotechnology 19, no. 12 (2019): 7982–92. http://dx.doi.org/10.1166/jnn.2019.16870.

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44

Park, Sun Hee, Yumi Park, Jeong Sik Han, Byung Hun Jeong, Hogyu Han, and Sung Hyun Kim. "Mechanistic Insights into Thermal Stability Improvement of exo-Tetrahydrodicyclopentadiene by a New Hydrogen Donor: 5,6,7,8-Tetrafluoro-1,2,3,4-tetrahydroquinoxaline." Energy & Fuels 29, no. 1 (2014): 16–20. http://dx.doi.org/10.1021/ef5016445.

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45

Гасанов, А. Г. о., И. Г. о. Аюбов, С. С. о. Алиев, М. М. г. Гурбанова та Ч. К. г. Салманова. "ИЗУЧЕНИЕ РЕАКЦИИ КАТАЛИТИЧЕСКОГО ГИДРИРОВАНИЯ ДИЦИКЛОПЕНТАДИЕНА". Вестник КНИИ РАН. Серия Естественные и технические науки, № 2(21) (17 липня 2025): 102–15. https://doi.org/10.69537/vkniiran.2025.21.2.009.

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Гидрирование дициклопентадиена (трицикло[5.2.1.02,6]-дека-3,8-диена) в при-сутствии гомо- и гетерогенных катализаторов является одной из ключевых реакций нефтехимиче-ского синтеза, приводящая к образованию смеси эндо- и экзо-изомеров тетрагидродициклопента-диена, являющегося основным компонентом реактивных топлив. В этой связи актуальность этой реакции не ослабевает и по сегодняшний день, а количество работ в направлении поиска новых оптимальных катализаторов для этой реакции, а также усовершенствования оптимальных режим-ных параметров процесса ежегодно возрастает. В представленной работе нами

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46

Zhao, Wenqi, Yitong Dai, Haiyun Sun, Yongsheng Guo, and Wenjun Fang. "Densities and Viscosities for the Ternary Mixtures of exo-Tetrahydrodicyclopentadiene (1) + Isopropylcyclohexane (2) + Methyl Laurate (3) and Corresponding Binaries." Journal of Chemical & Engineering Data 64, no. 9 (2019): 4013–23. http://dx.doi.org/10.1021/acs.jced.9b00397.

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47

Han, Kyu-Jin, In-Chan Hwang, So-Jin Park, Myung-Jae Choi, Sang-Bong Lee, and Jeong-Sik Han. "Vapor–liquid equilibrium, densities and viscosities for the binary system exo- and endo-tetrahydrodicyclopentadiene and pure component vapor pressures." Fluid Phase Equilibria 249, no. 1-2 (2006): 187–91. http://dx.doi.org/10.1016/j.fluid.2006.09.024.

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48

Brotton, Stephen J., Marc J. Malek, Scott L. Anderson, and Ralf I. Kaiser. "Effects of acetonitrile-assisted ball-milled aluminum nanoparticles on the ignition of acoustically levitated exo-tetrahydrodicyclopentadiene (JP-10) droplets." Chemical Physics Letters 754 (September 2020): 137679. http://dx.doi.org/10.1016/j.cplett.2020.137679.

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49

Perera, Sahan D., Stephen J. Brotton, Haylie Shinsato, Ralf I. Kaiser, Yuyeol Choi, and Kyungsu Na. "Catalytic Effects of Zeolite Socony Mobil-5 (ZSM-5) on the Oxidation of Acoustically Levitated exo-Tetrahydrodicyclopentadiene (JP-10) Droplets." Journal of Physical Chemistry A 125, no. 22 (2021): 4896–909. http://dx.doi.org/10.1021/acs.jpca.1c02892.

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50

Zhang, Lingling, Yongsheng Guo, Juan Xiao, Xianjie Gong, and Wenjun Fang. "Density, Refractive Index, Viscosity, and Surface Tension of Binary Mixtures ofexo-Tetrahydrodicyclopentadiene with Somen-Alkanes from (293.15 to 313.15) K." Journal of Chemical & Engineering Data 56, no. 11 (2011): 4268–73. http://dx.doi.org/10.1021/je200757a.

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