Propylamine → HCID 91725325, compound

HRID 1391272Notes

Reaction equation

HRID 1391272 reaction equation
[C:1]1([N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([NH2:20])[CH2:18][CH3:19].[OH-].[Na+]>>[C:1]1([N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](=[O:9])[NH:20][CH2:17][CH2:18][CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 7852PropylamineHCID 14798Sodium HydroxideHCID 65741N,N-Diphenylcarbamic chloride

Product 1

HCID 91725325HCID 91725325, compound

Procedure

By way of illustration, one mole of diphenylamine is reacted with a 10% molar excess of phosgene in a suitable solvent such as monochlorobenzene, to yield diphenylcarbamyl chloride. The carbamyl chloride thus produced is reacted further with n-propyl amine in stoichiometric amounts, in the presence of a mole of caustic soda. Diphenyl propyl urea (DPPU) is formed in essentially stoichiometric amounts. The DPPU formed may be either separated from the solvent or, if desired, supplied as a solution in its reaction solvent. DPPU pyrolyzes at 210°-220° C. to yield n-propyl isocyanate of 99% purity and greater than 90% yield. The diphenylamine remaining may be returned easily in tankcars or tankwagons for reprocessing.

Sources & evidence

ORD record
ord-952b6511f1c14015861602ecb3853be6
Source dataset
uspto-grants-1979_02
Patent number
US04141913

Reaction notes

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