Tricyclodecane Explained

Tricyclodecane (TCD) is an organic compound with the formula C10H16. It is classed as a hydrocarbon. It has two main stereoisomers–the endo and exo forms.[1] Its primary use in the exo form is as a component of jet fuel.[2] It is used here primarily because of its high energy density. The exo isomer also has a low freezing point.[3] [4] Because of this, its properties have been studied extensively.[5] [6] [7] [8] [9] It is often called tetrahydrodicyclopentadiene.

Reactions

Its reactions with other materials has been studied,[10] [11] as have various production methods.[12] [13] The two isomers can interconvert in the presence of aluminum chloride as catalyst absorbed on substrates such as silicon dioxide or zeolites,[14] [15] [16] [17] with preference for forming the exo as the major product.[18]

References

  1. Web site: Exo-tricyclo[5.2.1.0(2.6)]decane ]. 2023-10-03 . webbook.nist.gov . en.
  2. Hudzik . Jason M. . Asatryan . Rubik . Bozzelli . Joseph W. . 2010-09-09 . Thermochemical Properties of exo -Tricyclo[5.2.1.0 2,6 ]decane (JP-10 Jet Fuel) and Derived Tricyclodecyl Radicals ]. The Journal of Physical Chemistry A . en . 114 . 35 . 9545–9553 . 10.1021/jp1049556 . 20712369 . 2010JPCA..114.9545H . 1089-5639.
  3. Herbinet . Olivier . Sirjean . Baptiste . Bounaceur . Roda . Fournet . René . Battin-Leclerc . Frédérique . Scacchi . Gérard . Marquaire . Paul-Marie . 2006-10-01 . Primary Mechanism of the Thermal Decomposition of Tricyclodecane . The Journal of Physical Chemistry A . en . 110 . 39 . 11298–11314 . 10.1021/jp0623802 . 17004739 . 2006JPCA..11011298H . 1089-5639.
  4. Wu . Junjun . Gao . Lu Gem . Ning . Hongbo . Ren . Wei . Truhlar . Donald G. . 2020-06-01 . Direct dynamics of a large complex hydrocarbon reaction system: The reaction of OH with exo-tricyclodecane (the main component of Jet Propellant-10) . Combustion and Flame . 216 . 82–91 . 10.1016/j.combustflame.2020.02.019 . 216384271 . 0010-2180. free . 2020CoFl..216...82W .
  5. Web site: Exo-tricyclo[5.2.1.0(2.6)]decane ]. 2023-10-03 . Cheméo . en.
  6. Seiser . R. . Niemann . U. . Seshadri . K. . 2011-01-01 . Experimental study of combustion of n-decane and JP-10 in non-premixed flows . Proceedings of the Combustion Institute . 33 . 1 . 1045–1052 . 10.1016/j.proci.2010.06.078 . 1540-7489.
  7. Tao . Yujie . Xu . Rui . Wang . Kun . Shao . Jiankun . Johnson . Sarah E. . Movaghar . Ashkan . Han . Xu . Park . Ji-Woong . Lu . Tianfeng . Brezinsky . Kenneth . Egolfopoulos . Fokion N. . Davidson . David F. . Hanson . Ronald K. . Bowman . Craig T. . Wang . Hai . 2018-12-01 . A Physics based approach to modeling real fuel combustion chemistry III Reaction kinetic model of JP10 . Combustion and Flame . 198 . 466–476 . 10.1016/j.combustflame.2018.08.022 . 2018CoFl..198..466T . 104745782 . 0010-2180.
  8. Li . Heng . Liu . Guozhu . Jiang . Rongpei . Wang . Li . Zhang . Xiangwen . 2015-05-01 . Experimental and kinetic modeling study of exo-TCD pyrolysis under low pressure . Combustion and Flame . 162 . 5 . 2177–2190 . 10.1016/j.combustflame.2015.01.015 . 2015CoFl..162.2177L . 0010-2180.
  9. Goh . K. H. H. . Geipel . P. . Hampp . F. . Lindstedt . R. P. . 2013-01-01 . Regime transition from premixed to flameless oxidation in turbulent JP-10 flames . Proceedings of the Combustion Institute . 34 . 2 . 3311–3318 . 10.1016/j.proci.2012.06.173 . 1540-7489.
  10. Web site: STTR Navy FY09A - Characterization of the High Temperature Decomposition Products of JP-10 . 2023-10-03 . www.navysbir.com.
  11. Wu . Junjun . Gao . Lu Gem . Ning . Hongbo . Ren . Wei . Truhlar . Donald G. . 2020-06-01 . Direct dynamics of a large complex hydrocarbon reaction system: The reaction of OH with exo-tricyclodecane (the main component of Jet Propellant-10) . Combustion and Flame . 216 . 82–91 . 10.1016/j.combustflame.2020.02.019 . 216384271 . 0010-2180. free . 2020CoFl..216...82W .
  12. 2766301. Production of tricyclodecane. US. 1956-10-09. Ruhrchemie AG. Büchner. Karl. Roelen. Otto. Meis. Josef.
  13. Web site: Baptiste . Sirjean . Theoretical Study of the Thermal Decomposition of a Jet Fuel Surrogate .
  14. Sun . Cong-ming . Li . Gang . 2011-07-31 . Vapor-phase isomerization of endo-tetrahydrodicyclopentadiene to its exo isomer over zeolite catalysts . Applied Catalysis A: General . 402 . 1 . 196–200 . 10.1016/j.apcata.2011.06.008 . 0926-860X.
  15. Campo . Pablo del . Martínez . Cristina . Corma . Avelino . 2021-08-02 . Activation and conversion of alkanes in the confined space of zeolite-type materials . Chemical Society Reviews . en . 50 . 15 . 8511–8595 . 10.1039/D0CS01459A . 34128513 . 10251/183985 . 235437726 . 1460-4744. free .
  16. Navrátilová . Markéta . Sporka . Karel . 2000-09-18 . Synthesis of adamantane on commercially available zeolitic catalysts . Applied Catalysis A: General . 203 . 1 . 127–132 . 10.1016/S0926-860X(00)00477-4 . 0926-860X.
  17. Gallego . Eva María . Portilla . M. Teresa . Paris . Cecilia . León-Escamilla . Alejandro . Boronat . Mercedes . Moliner . Manuel . Corma . Avelino . 2017-03-10 . "Ab initio" synthesis of zeolites for preestablished catalytic reactions . Science . en . 355 . 6329 . 1051–1054 . 10.1126/science.aal0121 . 28280200 . 2017Sci...355.1051G . 10251/105508 . 206654251 . 0036-8075. free .
  18. Lili . Q. I. . Min* . J. I. . Xinkui . Wang . Min . H. E. . Tianxi . C. a. I. . 2010-04-25 . AlCl3/MCM-41 as a Catalyst for Isomerization of Endo-tricyclodecane . Chinese Journal of Catalysis . en . 31 . 4 . 383 . 0253-9837.

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