Acetic Acid → Azobenzene

HRID 267569Notes

Reaction equation

HRID 267569 reaction equation
C(O)(=O)C.OO.S(=O)(=O)(O)O.[C:12]([O:15][OH:16])(=[O:14])[CH3:13].CC(C)=O.N.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:29]1([NH:35]N=C(C)C)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CC(C)=NN=C(C)C>CO>[C:12]([O:15][OH:16])(=[O:14])[CH3:13].[N:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[N:35][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

12

Reactant 9

HCID 176Acetic AcidHCID 180AcetoneHCID 222Ammonia2×HCID 784Hydrogen Peroxide3×HCID 1118Sulfuric AcidHCID 6115AnilineHCID 6585Peracetic AcidHCID 660262-Propanone, 2-phenylhydrazoneHCID 79085Acetazine

Product 2

HCID 2272AzobenzeneYield 80.5%HCID 6585Peracetic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A crude peracetic acid solution was prepared by mixing 17.3 g glacial acetic acid (0.29 mole), 7.2 g of a hydrogen peroxide solution having 68% by weight of H2O2 (0.145 mole of H2O2), and 0.7 g concentrated sulphuric acid, and reacting the mixture for several hours at ambient temperature. A solution was obtained which contained 0.10 mole peracetic acid and 0.033 mole uncoverted hydrogen peroxide, and which was introduced into 200 ml of methanol at 0° C. Within the space of half an hour 34.8 g acetone (0.6 mole), 12.2 g of an ammonia solution having 28% by weight NH3 (0.2 mole), and 18.6 g aniline (0.2 mole) were added, after which the mixture was determined by gas phase chromatography to contain 4.6 g of acetone phenylhydrazone (0.031 mole, which was 31% of the theoretical yield compared to the peracid), 1 g of acetone azine (0.009 mole, which was 9% of the theoretical yield), and 0.025 mole of azobenzene.

Workup

  1. customfor several hours
  2. customat ambient temperature
  3. customA solution was obtained which
  4. additionwere added
  5. customtheoretical yield

Sources & evidence

ORD record
ord-3e1ee578b431452a8f9b2f5c7c58ed6b
Source dataset
uspto-grants-1976_03
Patent number
US03943132

Reaction notes

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