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Tricyclodecane

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(Redirected from Exo-tetrahydrodicyclopentadiene)
Tricyclodecane
endo
exo
Names
IUPAC name tricyclodecane
Other names Tetrahydrodicyclopentadiene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
EC Number
  • 227-851-2
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H16/c1-2-9-7-4-5-8(6-7)10(9)3-1/h7-10H,1-6H2Key: LPSXSORODABQKT-UHFFFAOYSA-N
SMILES
  • C1CC2C3CCC(C3)C2C1
Properties
Chemical formula C10H16
Molar mass 136.238 g·mol
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Signal word Danger
Hazard statements H226, H302, H304, H315, H319, H335
Precautionary statements P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P330, P331, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, P501
Related compounds
Related compounds Twistane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. Its primary use in the exo form is as a component of jet fuel. It is used here primarily because of its high energy density. The exo isomer also has a low freezing point. Because of this, its properties have been studied extensively. It is often called tetrahydrodicyclopentadiene.

Reactions

Its reactions with other materials have been studied, as have various production methods. The two isomers can interconvert in the presence of aluminum chloride as catalyst absorbed on substrates such as silicon dioxide or zeolites, with preference for forming the exo as the major product.

References

  1. "Tetrahydrodicyclopentadiene". pubchem.ncbi.nlm.nih.gov.
  2. "Exo-tricyclo[5.2.1.0(2.6)]decane". webbook.nist.gov. Retrieved 2023-10-03.
  3. 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. 114 (35): 9545–9553. Bibcode:2010JPCA..114.9545H. doi:10.1021/jp1049556. ISSN 1089-5639. PMID 20712369.
  4. 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. 110 (39): 11298–11314. Bibcode:2006JPCA..11011298H. doi:10.1021/jp0623802. ISSN 1089-5639. PMID 17004739.
  5. 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. Bibcode:2020CoFl..216...82W. doi:10.1016/j.combustflame.2020.02.019. ISSN 0010-2180. S2CID 216384271.
  6. "Exo-tricyclo[5.2.1.0(2.6)]decane". Cheméo. Retrieved 2023-10-03.
  7. 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. Bibcode:2011PComI..33.1045S. doi:10.1016/j.proci.2010.06.078. ISSN 1540-7489.
  8. 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. Bibcode:2018CoFl..198..466T. doi:10.1016/j.combustflame.2018.08.022. ISSN 0010-2180. S2CID 104745782.
  9. 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. Bibcode:2015CoFl..162.2177L. doi:10.1016/j.combustflame.2015.01.015. ISSN 0010-2180.
  10. 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. Bibcode:2013PComI..34.3311G. doi:10.1016/j.proci.2012.06.173. ISSN 1540-7489.
  11. "STTR Navy FY09A - Characterization of the High Temperature Decomposition Products of JP-10". www.navysbir.com. Retrieved 2023-10-03.
  12. 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. Bibcode:2020CoFl..216...82W. doi:10.1016/j.combustflame.2020.02.019. ISSN 0010-2180. S2CID 216384271.
  13. US 2766301, Büchner, Karl; Roelen, Otto & Meis, Josef, "Production of tricyclodecane", published 1956-10-09, assigned to Ruhrchemie AG 
  14. Baptiste, Sirjean. "Theoretical Study of the Thermal Decomposition of a Jet Fuel Surrogate".
  15. 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. doi:10.1016/j.apcata.2011.06.008. ISSN 0926-860X.
  16. 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. 50 (15): 8511–8595. doi:10.1039/D0CS01459A. hdl:10251/183985. ISSN 1460-4744. PMID 34128513. S2CID 235437726.
  17. Navrátilová, Markéta; Sporka, Karel (2000-09-18). "Synthesis of adamantane on commercially available zeolitic catalysts". Applied Catalysis A: General. 203 (1): 127–132. doi:10.1016/S0926-860X(00)00477-4. ISSN 0926-860X.
  18. 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. 355 (6329): 1051–1054. Bibcode:2017Sci...355.1051G. doi:10.1126/science.aal0121. hdl:10251/105508. ISSN 0036-8075. PMID 28280200. S2CID 206654251.
  19. 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. 31 (4): 383. ISSN 0253-9837.
  20. Clarke, J. K. A.; Rooney, J. J. (1976-01-01), Eley, D. D.; Pines, Herman; Weisz, Paul B. (eds.), Stereochemical Approaches to Mechanisms of Hydrocarbon Reactions on Metal Catalysts, Advances in Catalysis, vol. 25, Academic Press, pp. 125–183, doi:10.1016/s0360-0564(08)60314-4, ISBN 978-0-12-007825-7, retrieved 2023-11-20
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