Applied Chemistry for Engineering (공업화학)

The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
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A Study on the Reaction Pathway for Isomerization of Tetrahydrotricyclopentadiene Using Ionic Liquid Catalyst

이온성 액체 촉매를 이용한 Tetrahydrotricyclopentadiene의 이성화 반응 경로에 관한 연구

  • Kim, Dae Hyun (Division of Advanced material Engineering, Kongju National University) ;
  • Han, Jeong-Sik (Agency for Defense Development) ;
  • Jeon, Jong-Ki (Department of Chemical engineering, Kongju National University) ;
  • Yim, Jin-Heong (Division of Advanced material Engineering, Kongju National University)
  • Received : 2015.04.21
  • Accepted : 2015.04.29
  • Published : 2015.06.10
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Abstract

The kinetic behavior of tetrahydrotricyclopentadiene (THTCPD) isomerization was studied by using two kinds of chloroaluminate ionic liquid (IL) catalyst with different Lewis acidity. THTCPD isomerization pathway was discussed under the different temperature and time as reaction parameters using IL catalysts consisting of 1-butyl-3-methylimidazolun chloride $(BMIC)/AlCl_3$ with low acidity and pyridine hydrochloride $(PHC)/AlCl_3$ with high acidity. The conversion of THTCPD isomerization increased with increasing Lewis acidity of IL catalyst. The THTCPD isomerization pathway changed as a function of reaction temperature and catalyst acidity. In the case of $BMIC/AlCl_3$ IL catalyst, THTCPD isomerization pathway was similar to that of using conventional $AlCl_3$ catalyst. However, two different types of additional pathways (endo, exo, endo-NB ${\rightarrow}$ exo, exo, endo-NB ${\rightarrow}$ exo, exo, exo-NB and endo, exo, endo-NB ${\rightarrow}$ exo, exo, endo-NB ${\rightarrow}$ exo, exo, exo-CP) were appeared when using $PHC/AlCl_3$ IL catalyst.

루이스 산도가 다른 두 종류의 클로로알루미네이트계 이온성 액체(IL) 촉매를 사용하여 tetrahydrotricyclopentadiene (THTCPD) 이성화 반응 거동에 관하여 연구하였다. 루이스 산도가 낮은 1-butyl-3-methylimidazolun chloride $(BMIC)/AlCl_3$와 높은 pyridine hydrochloride $(PHC)/AlCl_3$계 IL 촉매를 이용하고 온도와 시간을 반응 인자로 하여 THTCPD의 이성화 반응 경로를 고찰하였다. IL 촉매의 루이스 산도 증가에 따라 THTCPD 이성화 전환율을 증가시킬 수 있었다. 반응온도 및 IL 촉매의 산도에 따라 THTCPD 이성화 반응경로가 바뀌었다. 산도가 낮은 $BMIC/AlCl_3$ IL 촉매의 경우에는 기존에 사용되어오던 $AlCl_3$ 촉매와 유사한 반응 경로를 보이지만, 반응온도가 높아짐에 따라 endo, exo, endo-(norbornene; NB) ${\rightarrow}$ exo, exo, endo-NB ${\rightarrow}$ diamondoid로의 골격 재배열화 반응이 일어났다. 하지만, 산도가 높은 $PHC/AlCl_3$ IL 촉매의 경우에는 $TEAC/AlCl_3$ IL 촉매와는 다른 새로운 두 가지 경로(endo, exo, endo-NB ${\rightarrow}$ exo, exo, endo- NB ${\rightarrow}$ exo, exo, exo-NB 및 endo, exo, endo-NB ${\rightarrow}$ exo, exo, endo-NB ${\rightarrow}$ exo, exo, exo-(cyclopentadiene; CP))가 추가로 관찰되었다.

Keywords

References

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