Ethylbenzene → 2-Phenylpropionitrile
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[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:2].[H][H].FC1C(F)=C(C#N)C(F)=C(F)C=1[C:14]#[N:15].FC1C(F)=CC(F)=C(F)C=1C#N>[Pd]>[CH3:2][CH:1]([C:14]#[N:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:2].[H][H].FC1C(F)=C(C#N)C(F)=C(F)C=1[C:14]#[N:15].FC1C(F)=CC(F)=C(F)C=1C#N>[Pd]>[CH3:2][CH:1]([C:14]#[N:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1100 g of ethylbenzene and 3.0 g of 5% palladium/activated carbon were added to a 1000 cc stainless steel autoclave. The gas phase was sufficiently replaced with hydrogen gas, then hydrogen gas was used to apply a pressure of 0.3 MPa and make the temperature 100° C. and catalytic pretreatment was carried out for 1 hour. The gas phase was again sufficiently replaced with nitrogen, then 3.0 g of the reaction material, that is, 2,3,5,6-tetrafluoroterephthalonitrile was added. The nitrogen atmosphere was maintained, the autoclave sealed as it was at atmospheric pressure, and the temperature held at 175° C. After 3 hours, the reaction solution was analyzed by gas chromatography, whereupon the conversion of 2,3,5,6-tetrafluoroterephthalonitrile was found to be 100% and the yield of 2,3,5,6-tetrafluorobenzonitrile (based on 2,3,5,6-tetrafluoroterephthalonitrile) was 95%. At the same time, 13.4 mmol of α-methylbenzylcyanide was produced. This corresponded to 0.95 times molar amount relative to the production of 2,3,5,6-tetrafluorobenzonitrile.
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