Hydroquinone → Bicyclo[2.2.1]hept-2-ene-1-carbonitrile
Reaction equation
C1[CH:5]2[CH:6]3[CH:10]=[CH:9][CH:8]([CH:4]2C=C1)[CH2:7]3.[C:11](#[N:14])C=C.C1(C=CC(O)=CC=1)O>>[C:11]([C:6]12[CH2:7][CH:8]([CH2:4][CH2:5]1)[CH:9]=[CH:10]2)#[N:14]Participants
Procedure
Dicyclopentadiene of 54.2%, acrylonitrile of 45.8% and hydroquinone of 500 ppm as a polymerization inhibitor were mixed, and this mixed solution was continuously fed into a tubular reactor (inner diameter: 8 mm) at a rate of 50 ml/hr, wherein the reaction temperature was controlled to 153° C. in a residence time of the reaction solution of up to 5 hours, 170° C. in a residence time of up to 7 hours and 180° C. in a residence time of up to 9 hours. After this reaction reached a steady state, the reaction was further continued for 20 hours to obtain crude cyanonorbornene of about 1 liter having a purity of 95%. This was concentrated under reduced pressure to distill off unreacted cyclopentadiene and acrylonitrile, whereby cyanonorbornene of 950 g having a purity of 99.6% was obtained.
Workup
- customthis mixed solution was continuously fed into a tubular reactor
- customwas controlled to 153° C. in a residence time of the reaction solution
- customup to 5 hours
- wait180° C. in a residence time of up to 9 hours
- waitthe reaction was further continued for 20 hours
Sources & evidence
- ORD record
- ord-0f6ca26b7f8147c39ce9004dbf451fe4
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05789520
Reaction notes
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