Catalytic hydrogenation of dicyclopentadiene to dicyclopentene in the liquid phase

Antonova, T. N.; Абрамов, И. А.; Fel'dblyum, V. Sh.; Абрамов, И. Г.; Danilova, A. S.

doi:10.1134/s0965544109050041

Cited by 16 publications

(6 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…When the reaction temperature increased to 15°C, the reaction conversion went up to 85 % ( Table 2, entry 2). Further increase temperature to 25 and 45°C, the equilibrium conversion is dramatically lowered ( Table 2, entries [3][4]. This is because the equilibrium constant of the exothermic reaction decreases with rising temperature.…”

Section: Isomerization Of Thtcpd To Exo-thtcpdmentioning

confidence: 94%

See 1 more Smart Citation

One-Pot Catalytic Transformation of Dicyclopentadiene to High Energy Density Fuel Exo-tetrahydrotricyclopentadiene

Wang

Chen

et al. 2015

Top Catal

View full text Add to dashboard Cite

Energy density of fuel is an important issue for advanced aircrafts and spacecrafts. Exo-tetrahydrotricyclopentadiene (exo-THTCPD) is a promising high-energy density fuel candidate with many desirable properties, including high volumetric energy content (43.2 MJ/L), high density (1.04 g/mL) and low freezing point (\-40°C). In this work, we demonstrated the first example of one-pot catalytic synthesis of exo-THTCPD directly from dicyclopentadiene (DCPD). The whole procedure was fulfilled in one-pot by three steps. First, tricyclopentadiene (TCPD) was prepared directly from the dissociation-recombination of DCPD at 200°C. Then the reaction mixture (the majority is TCPD, mixed with small amount of DCPD and tetracyclopentadiene) was saturated using supported noble metal catalysts at 150°C under 4.0 MPa H 2 . Finally, the hydrogenated mixture was treated by AlCl 3 -catalytic isomerization at 15°C. Like most synthesis processes, fractional distillation was needed to obtain the final product of exo-THTCPD. Compared with previous routes, the new protocol has many advantages such as one-pot, high concentration, less solvents, low catalyst loading, short reaction time, etc, and therefore showed great potential for industrial applications. Graphical Abstract one-potPd/C, AlCl 3

show abstract

Section: Isomerization Of Thtcpd To Exo-thtcpdmentioning

confidence: 94%

“…It has been widely used in land-, ship-and air-launched missiles [3][4][5][6][7]. Recently, researchers are exploring fuels with higher volumetric energy content [8][9][10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

One-Pot Catalytic Transformation of Dicyclopentadiene to High Energy Density Fuel Exo-tetrahydrotricyclopentadiene

Wang

Chen

et al. 2015

Top Catal

View full text Add to dashboard Cite

show abstract

“…Cyclopentadiene and its derivative dicyclopentadiene (DCPD) with highly active norborane and cyclopentadiene units are the byproducts of pyrolysis of petroleum feedstocks. [1][2][3] It has two isomers, endo-dicyclopentadiene and exo-dicyclopentadiene. Most of the chemical and physical properties of these isomers are similar.…”

Section: Introductionmentioning

confidence: 99%

Single-step catalytic liquid-phase hydroconversion of DCPD into high energy density fuel exo-THDCPD

et al. 2012

View full text Add to dashboard Cite

Hydroconversion of dicyclopentadiene (DCPD) into high energy density jet propellant JP-10 has been successfully achieved with a greener single-step route over supported gold catalyst. The physicochemical properties of the catalysts were studied with XRD, SEM, TEM, N 2 -adsorption, NH 3 -TPD. The influence of reaction conditions like temperature, pressure, time etc. were studied in detail. The studies reveal that pressure and temperature play crucial roles in the reaction. Moderate acid sites in the catalysts are chiefly involved in isomerization and gold catalyzes hydrogenation of the intermediates. Analysis of the product stream at different intervals indicates a dissociation-recombination mechanism for the reaction. Reusability of the catalyst was tested by conducting five runs with the same catalyst. Even after the fifth run, the catalyst retains relatively high conversion and selectivity to exo-tetrahydrodicyclopentadiene (exo-THDCPD). † Electronic supplementary information (ESI) available. See

show abstract

“…Furthermore, oxygen containing dicyclo pentene derivatives are of interest for the fabrication of polymers, liquid crystals, and other materials [1][2][3][4].…”

mentioning

confidence: 99%

“…At the same time, it was found [1] that in the case of dicyclopentadiene hydrogenation under atmo spheric pressure over supported palladium catalysts, either finely divided or shaped, the yield of target dicy clopentene can be as high as 92 mol % and the dihyd rodicyclopentadiene) (dicyclopentene) to tetrahyd rodicyclopentadiene (dicyclopentane) ratio is 11.5 : 1. Finely divided catalysts are convenient for practical implementation of the process.…”

mentioning

confidence: 99%

Features of dicyclopentene formation during hydrogenation of dicyclopentadiene

et al. 2016

Self Cite

View full text Add to dashboard Cite

Abstracts-General trends and specific features of the reaction of dicyclopentadiene (tricyclo[5.2.1.0 2.6 ]dec adiene 3,8) hydrogenation to dicyclopentene (tricycle[5.2.1.0 2.6 ]decene 3) with hydrogen in the liquid phase under mild conditions at atmospheric pressure over a finely divided 1% Pd/C catalyst have been studied. The kinetic parameters that characterize the effect of the solvent nature, catalyst concentration, and temperature on the rate of hydrogen uptake in the hydrogenation process have been determined. To substantiate the con clusion of the sequence of saturation of the dicyclopentadiene double bonds in terms of the mechanism of heterogeneous catalysis, their reactivity has been compared. It has been shown that in the presence of a num ber of functionalized aromatic compounds as a stabilizing additive, the yield of desired dicyclopentene increases to 98.5-99 mol % with the complete conversion of dicyclopentadiene. The structure of dicyclopen tadiene and its hydrogenation product dicyclopentene has been confirmed using spectroscopic methods.

show abstract

Catalytic hydrogenation of dicyclopentadiene to dicyclopentene in the liquid phase

Cited by 16 publications

References 0 publications

One-Pot Catalytic Transformation of Dicyclopentadiene to High Energy Density Fuel Exo-tetrahydrotricyclopentadiene

One-Pot Catalytic Transformation of Dicyclopentadiene to High Energy Density Fuel Exo-tetrahydrotricyclopentadiene

Single-step catalytic liquid-phase hydroconversion of DCPD into high energy density fuel exo-THDCPD

Features of dicyclopentene formation during hydrogenation of dicyclopentadiene

Contact Info

Product

Resources

About