N-Phenyl-p-phenylenediamine → n-(1-Methyldecyl)-n'-phenyl-p-phenylenediamine

HRID 558005

Reaction equation

HRID 558005 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[CH3:15][C:16](=O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[H][H]>[Pt]=S>[CH3:25][CH:24]([NH:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)=[CH:9][CH:10]=1)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15]

Participants

5

Reactant 3

HCID 7564N-Phenyl-p-phenylenediamineHCID 81632-UndecanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 20559829n-(1-Methyldecyl)-n'-phenyl-p-phenylenediamine

Reagents, catalysts & solvents 1

HCID 82861Platinum sulfide (PtS)Catalyst

Conditions

Temperature
120 °C

Procedure

Para-aminodiphenylamine (184 grams, 1.00 mole), 2-undecanone (221 grams, 1.30 moles) and 6.0 grams (dry weight) of carbon supported platinum sulfide catalyst were charged to a one-liter stirred autoclave. The vessel was sealed, pressurized first with nitrogen and then with hydrogen gas, stirred, and heated to 120° C. until the reaction was completed, as indicated by the cessation of hydrogen absorption. The vessel was cooled, vented, and the contents removed. The catalyst was removed by filtration and the water was separated. The excess ketone reactant was removed by heating in vacuo.

Workup

  1. additionwere charged to a one-liter stirred autoclave
  2. customThe vessel was sealed
  3. customas indicated by the cessation of hydrogen absorption
  4. temperatureThe vessel was cooled
  5. customthe contents removed
  6. customThe catalyst was removed by filtration
  7. customthe water was separated
  8. customThe excess ketone reactant was removed
  9. temperatureby heating in vacuo

Sources & evidence

ORD record
ord-43d9bddf10d24c5db0ee86af93745b2c
Source dataset
uspto-grants-2011_11
Patent number
US08062551B2

Linked notes

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