Thermal stability and isomerization mechanism of exo- tetrahydrodicyclopentadiene: Experimental study and molecular modeling

Sun Hee Park, Cheong Hoon Kwon, Joongyeon Kim, Byung Hee Chun, Jeong Won Kang, Jeong Sik Han, Byung Hun Jeong, Sung Hyun Kim

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Thermal stability and the primary initiation mechanism of exo-tetrahydrodicyclopentadiene (exo-THDCP, C10H16) were investigated in a batch-type reactor. The catalytic role of the stainless steel inside the reactor was eliminated by inserting a quartz flask. exo-THDCP decomposed at temperatures over 623 K and 1-cyclopentylcyclopentene (1-CPCP, C10H16) and 4-methyl-2,3,4,5,6,7-hexahydro-1H-indene (4-MHI, C10H16) were the primary decomposition products of exo-THDCP. C10 hydrocarbons were determined to be the major products. The amount of C5-C7 hydrocarbons, such as cyclopentene, benzene, and toluene, were relatively small. We performed the molecular modeling (MM) on some of the compounds, including 1-CPCP and 4-MHI produced from exo-THDCP to evaluate the activation energy and molecular structure of the intermediates. The experimental and MM results showed that 1-CPCP and 4-MHI were independently formed from exo-THDCP. The experimental results closely corresponded with the MM result; the products that were only minimally produced after the reaction had qualitatively higher activation energies than the other products.

Original languageEnglish
Pages (from-to)8319-8324
Number of pages6
JournalIndustrial and Engineering Chemistry Research
Volume49
Issue number18
DOIs
Publication statusPublished - 2010 Sep 15

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Molecular modeling
Isomerization
Thermodynamic stability
Hydrocarbons
Activation energy
Cyclopentanes
Quartz
Stainless Steel
Toluene
Benzene
Molecular structure
Stainless steel
Decomposition
Temperature

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)
  • Industrial and Manufacturing Engineering

Cite this

Thermal stability and isomerization mechanism of exo- tetrahydrodicyclopentadiene : Experimental study and molecular modeling. / Park, Sun Hee; Kwon, Cheong Hoon; Kim, Joongyeon; Chun, Byung Hee; Kang, Jeong Won; Han, Jeong Sik; Jeong, Byung Hun; Kim, Sung Hyun.

In: Industrial and Engineering Chemistry Research, Vol. 49, No. 18, 15.09.2010, p. 8319-8324.

Research output: Contribution to journalArticle

Park, Sun Hee ; Kwon, Cheong Hoon ; Kim, Joongyeon ; Chun, Byung Hee ; Kang, Jeong Won ; Han, Jeong Sik ; Jeong, Byung Hun ; Kim, Sung Hyun. / Thermal stability and isomerization mechanism of exo- tetrahydrodicyclopentadiene : Experimental study and molecular modeling. In: Industrial and Engineering Chemistry Research. 2010 ; Vol. 49, No. 18. pp. 8319-8324.
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