Sulfuric Acid → 2,2'-Azobis(2,4-dimethylvaleronitrile)
Reaction equation
[NH2:1][C:2]([CH3:9])([CH2:5][CH:6]([CH3:8])[CH3:7])[C:3]#[N:4].Cl[O-].[Na+].S(=O)(=O)(O)O.S(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C>[N:1]([C:2]([CH3:9])([CH2:5][CH:6]([CH3:8])[CH3:7])[C:3]#[N:4])=[N:1][C:2]([CH3:9])([CH2:5][CH:6]([CH3:8])[CH3:7])[C:3]#[N:4]Participants
Conditions
- Temperature
- 15 °C
Procedure
In the same manner as in Example 1, 2-amino-2,4-dimethylpentanonitrile and sodium hypochlorite were reacted. By iodometry, it was found that the total oxidative compounds in both the water and ethyl acetate phases after reaction was 0.05 equivalent. The reaction mixture was adjusted to a pH of 6 with a dilute sulfuric acid, and a solution of 6.5 g (0.125 equivalent) of sodium bisulfite in 30 ml of water was added thereto. The resulting mixture was stirred at 15° C. for 30 minutes to effect the reduction. Thereafter, the ethyl acetate phase was separated from the water phase, and the ethyl acetate in the organic phase was removed by distillation. Water was added to the residue and precipitated white crystals were filtered, washed with water and dried to obtain 26.0 g of 2,2'-azobis(2,4-dimethylvaleronitrile). Yield was 89 mole %. The product was analyzed by iodometry, and it was found that the amount of oxidative impurities was 100 ppm or less and that the purity of the product was 99.5%.
Workup
- customafter reaction
- customThereafter, the ethyl acetate phase was separated from the water phase
- customthe ethyl acetate in the organic phase was removed by distillation
- additionWater was added to the residue
- customprecipitated white crystals
- filtrationwere filtered
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-84c7bdfa22364d32b0649b190f9ec153
- Source dataset
- uspto-grants-1981_06
- Patent number
- US04272435
Reaction notes
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