Hydrochloric Acid → 2,2'-Azobis(2,4-dimethylvaleronitrile)

HRID 1578483Notes

Reaction equation

HRID 1578483 reaction equation
Cl[O-].[Ca+2].Cl[O-].[NH2:6][C:7]([CH3:16])([CH2:10][C:11](OC)([CH3:13])[CH3:12])[C:8]#[N:9].S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>O.CO>[N:6]([C:7]([CH3:16])([CH2:10][CH:11]([CH3:13])[CH3:12])[C:8]#[N:9])=[N:6][C:7]([CH3:16])([CH2:10][CH:11]([CH3:13])[CH3:12])[C:8]#[N:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24477Sodium ThiosulfateHCID 24504Calcium hypochloriteHCID 92081Pentanenitrile, 2-amino-4-methoxy-2,4-dimethyl-

Product 1

HCID 915372,2'-Azobis(2,4-dimethylvaleronitrile)

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a mixture of 276 parts of methanol and 129 parts of 10% aqueous calcium hypochlorite at -10°C. are added with agitation 15.6 parts of 2-amino-4-methoxy-2,4-dimethylpentanonitrile. The mixture was stirred for approximately 45 minutes while the temperature was allowed to rise to 10°C. At this point in the reaction methanol constitutes 75 volume percent of the aqueous solvent. Titration with sodium thiosulfate as described in Example 1 showed 0.045 equivalent of oxidizing agents in the reaction mixture. The reaction mixture was then acidified to a pH of 3 with 10% hydrochloric acid and 2.16 grams (.0675 equivalent) of SO2 gas were added to the mixture, followed by 232 parts of water. The precipitated 2,2'-azobis (2,4-dimethylvaleronitrile), isolated by filtration, was found to be white and free-flowing and had a purity of 97.7%.

Workup

  1. customto rise to 10°C
  2. additionwere added to the mixture

Sources & evidence

ORD record
ord-2ef3c8ab5a1b444193f9e58f42a9101f
Source dataset
uspto-grants-1976_02
Patent number
US03937696

Reaction notes

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