Study on the oligomerization of cyclopentadiene and dicyclopentadiene to tricyclopentadiene through diels-alder reaction

Abstract

The oligomerization of cyclopentadiene (CPD) and its dimer, dicyclopentadiene (DCPD), to tricyclopentadiene (TCPD) through Diels-Alder reaction at temperatures between 120 and 150°C was investigated. The results show that reaction temperature, pressure and solvent influence the product yield; at 150°C up to 50% yield of TCPD was obtained in the absence of solvents. The ratios of isomers A to B in the product can be adjusted by using different solvents. The kinetics indicate that the rate is more sensitive to the concentration of CPD than to that of DCPD.

Preparation of Pd-B/γ-Al2O3 amorphous catalyst for the hydrogenation of tricyclopentadiene

“…TCPD used for the hydrogenation reaction was prepared by the oligomeraiztion of cyclopentadiene and then distillation to remove the un-reacted feedstock according to previous work [4]. The purity of obtained TCPD was >96% as determined by GC.…”

“…High energy density fuel with high density and volumetric energy content (or heating value) can provide more propulsive energy than traditional aviation fuels obtained from refinery [1][2][3][4][5]. Since it can significantly promote the flight distance and loading of aircrafts, the synthesis of high energy density fuel has attracted increasing interests.…”

“…Generally, these fuels are liquid hydrocarbons with three to five rings. Tetrahydrotricyclopentadiene (THTCPD, tetracyclo [9.2.1.1 3,9 .0 4,8 ] pentadecane) has been regarded as a potential high energy fuel because of its high density and low viscosity [1][2][3][4]. THTCPD is prepared through the hydrogenation of tricyclopentadiene (TCPD, trimer of cyclopentadiene).…”

Synthesis of Tricyclopentadiene Using Ionic Liquid Supported Mesoporous Silica Catalysts

“…그중 Tetrahydrotricyclopentadiene (THTCPD)는 높은 밀도(1.08 g/mL)와 체적당 에너지(44.9 MJ/L)를 가지고 있어서 주목을 받고 있다 [2]. THTCPD는 Dicycloentadiene (DCPD)와 Cyclopentadiene (CPD) 간의 고리화 반응으로 만들 어진 TCPD를 수소화 하여 얻을 수 있다 [3][4][5][6]. 하지만 CPD와 DCPD 가 반응할 때 TCPD 뿐만 아니라 Tetracyclopentadiene (TeCPD), Pentacyclopentadiene (PeCPD) 등 소중합화가 동시에 진행되기 때문 에 TCPD의 선택도를 높이는 것이 중요하다 [4].…”

“…Reaction condition : reaction temperature = 160 ℃, time = 20 hrs, rpm = 500, pressure = 9 bar (2) Reaction condition : catalyst contents of CuCl = 20 wt%, ionic-liquid mole fraction x = 0.67 (3) Reaction condition : catalyst contents of FeCl3 = 10 wt%, ionic-liquid mole fraction x = 0.67 (4) Reaction condition : catalyst contents of the supported = 10 wt%, IL/MCM-41 = 100%, ionic-liquid mole fraction x = 0.67 …”