Ethanol → n,n-Di(2-ethylhexyl)-p-phenylenediamine

HRID 581212Notes

Reaction equation

HRID 581212 reaction equation
[OH-].[Na+].C([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH2:22][CH:23]([CH2:28][CH3:29])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:14][CH:15]([CH2:20][CH3:21])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:9][CH:8]=1)(=O)C.C(O)C>O>[CH2:20]([CH:15]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:14][N:13]([CH2:22][CH:23]([CH2:28][CH3:29])[CH2:24][CH2:25][CH2:26][CH3:27])[C:10]1[CH:9]=[CH:8][C:7]([NH2:6])=[CH:12][CH:11]=1)[CH3:21]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 54311391n-Acetyl-n',n'-di(2-ethylhexyl)-p-phenylenediamine

Product 1

HCID 53999179n,n-Di(2-ethylhexyl)-p-phenylenediamineYield 53.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixed solution comprising 8 ml of 30% sodium hydroxide solution, 1.012 g of N-acetyl-N',N'-di(2-ethylhexyl)-p-phenylenediamine and 10 ml of ethanol was allowed to react at 75° C. for a period of 5 hr. After the completion of the reaction, the reacted solution was introduced into water and the product was extracted by ethyl acetate. After ethyl acetate was distilled away, the residue was purified by silica gel column chromatography to obtain 501 mg of oil of N,N-di(2-ethylhexyl)-p-phenylenediamine (yield 53.4%).

Workup

  1. customto react at 75° C. for a period of 5 hr
  2. customAfter the completion of the reaction
  3. extractionthe product was extracted by ethyl acetate
  4. distillationAfter ethyl acetate was distilled away
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3175547f3728479789011190a3d0b141
Source dataset
uspto-grants-1999_07
Patent number
US05919928

Reaction notes

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