Hydrochloric Acid → Aniline

HRID 2372935Notes

Reaction equation

HRID 2372935 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-:10])=[O:9].[CH2:17]([OH:19])C.[C:20]1([CH3:26])C=CC=CC=1.Cl>>[C:2]1([NH:1][C:17](=[O:19])[O:9][CH2:20][CH3:26])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:8][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1140TolueneHCID 6115AnilineHCID 7416Nitrobenzene

Product 3

HCID 6115AnilineHCID 7416NitrobenzeneHCID 7591Ethyl N-phenylcarbamate

Procedure

Into a 100 ml capacity SUS 316 stainless autoclave were fed the above catalyst (61.9 mg) (0.020 mmol in terms of Pd), aniline (0.931 g, 0.010 mol), nitrobenzene (1.23 g, 0.010 mol), ethanol (4.61 g, 0.10 mol), toluene (10.6 g, 0.11 mol) and 35% hydrochloric acid aqueous solution (0.071 g, HCl=0.68 mmol, H2O=0.067 mmol), followed by introducing CO gas up to 28 Kg/cm2 at room temperature without purging the air inside the system, reacting them at a reaction temperature of 190° C. for 3 hours, cooling the reaction mixture down to room temperature after the reaction, returning the pressure inside the system to the atmospheric pressure and analyzing the reaction product according to gas chromatography. As a result, ethyl N-phenylcarbamate (NPU) (2.97 g) was formed (NPU yield: 90%), and aniline (0.093 g, 0.001 mol) and nitrobenzene (0.123 g, 0.001 mol) remained unreacted.

Workup

  1. additionby introducing CO gas up to 28 Kg/cm2 at room temperature
  2. customwithout purging the air inside the system
  3. customat a reaction temperature of 190° C.
  4. customfor 3 hours
  5. customafter the reaction

Sources & evidence

ORD record
ord-8c96a7765e944936a2797f939ffac46c
Source dataset
uspto-grants-1992_03
Patent number
US05101062

Reaction notes

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