Dicyclopentadiene → Dicyclopentadiene
Reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[CH2:6]1[CH:10]2[CH:11]3[CH:15]=[CH:14][CH:13]([CH:9]2[CH:8]=[CH:7]1)[CH2:12]3>>[CH2:7]1[CH2:6][C@H:10]2[C@H:9]([C@H:13]3[CH2:12][C@@H:11]2[CH2:15][CH2:14]3)[CH2:8]1.[CH2:2]1[CH:1]2[CH:8]3[CH:7]=[CH:6][CH:10]([CH:5]2[CH:4]=[CH:3]1)[CH2:9]3Participants
Procedure
In the prior art, JP-10 is prepared by first completely hydrogenating extra-high purity cyclopentadiene (CPD) dimer, namely dicyclopentadiene (DCPD, freezing point of 33.6° C.), as a precursor to yield the solid endo-isomer of the hydrogenated derivative, namely endo-THDCPD (freezing point of 77° C.), wherein the hydrogenation of DCPD is carried out in two stages (the first stage and the second stage). In the first stage, the dihydro derivative, namely dihydrodicyclopentadiene (DHDCPD, freezing point of 51° C.) was obtained by selective hydrogenation of DCPD in the presence of nickel or palladium catalyst at the temperature of 50-120° C. In the second stage, the solid endo-THDCPD (freezing point of 77° C.) was obtained by hydrogenation of DHDCPD in the presence of metal catalyst at the temperature of 130-220° C. Finally, the solid endo-THDCPD is isomerized to the liquid exo-THDCPD, namely JP-10 (freezing point <−79° C.), in an amount of more than 98.5% of the total product weight in the presence of an acidic catalyst. JP-10 is very expensive because it is obtained by chemical synthesis from extra-high purity DCPD using a batch reactor (referring to U.S. Pat. Nos. 3,381,046, 4,086,284, 4,107,223, and 4,270,014).
Sources & evidence
- ORD record
- ord-d5596b9932fc426a829877546970da16
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450544B2
Reaction notes
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