Ammonia → Tribenzylamine

HRID 52799Notes

Reaction equation

HRID 52799 reaction equation
N.[CH:2](=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[Pd].O>[CH2:2]([OH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:2]([N:17]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 3

HCID 222AmmoniaHCID 240BenzaldehydeHCID 7656Dibenzylamine

Product 3

HCID 244Benzyl AlcoholYield 0.4%HCID 7504BenzylamineYield 0.9%HCID 24321TribenzylamineYield 2.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Into an inertised Buss loop reactor with a capacity of 50 liters were successively introduced 40.74 kg BALD (0.384 kmol) and 4.1 kg H2O. The circulation pump was then started and 0.0815 kg 4% palladium/carbon (Degussa E196 NN-W; 50% H2O) was added. The trial was further carried out along the same lines as Example X, except that 4.76 kg NH3 (0.280 kmol) was added. Gas chromatography analysis of the organic phase showed that all the benzaldehyde had been converted. The selectivity to dibenzylamine was 92.5%. In addition, small amounts of benzylalcohol (sel. approx. 0.4%), benzylamine (sel. approx. 0.9%), dibenzylimine (sel. approx. 0-1%) and tribenzylamine (sel. approx. 2.4%) were formed.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-38cd10886926448bbb5deb01862826e1
Source dataset
uspto-grants-1997_04
Patent number
US05616804

Reaction notes

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