Hydrazine hydrate (1:1) → Styrene

HRID 1284286Notes

Reaction equation

HRID 1284286 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[CH2:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.NN>C(O)C>[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[CH2:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22731677HCID 22731677, compound

Product 2

HCID 7294Methyl AcrylateYield 22%HCID 7501StyreneYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 500-ml three-necked round-bottomed flask equipped with a magnetic stirrer, condenser, and nitrogen sweep were placed the methyl acrylate-styrene copolymer (50.0 g), ethanol (200 ml), and 85% hydrazine hydrate (100 ml). The reaction mixture was stirred and heated at reflux for 48 hours. The cooled reaction mixture was poured slowly into distilled water (200 ml) being agitated in an air-driven blender. The white precipitate was collected on a Buchner funnel, sucked dry, and vacuum-dried at 50°C. This procedure yields a poly(hydrazide) containing 28% hydrazide, 22% methyl acrylate, and 50% styrene when starting with the 50/50 copolymer. The proportion of hydrazide can be increased by using longer reaction times. The reaction time can be halved by substituting dimethyl sulfoxide for ethanol but the recovery step takes more time.

Workup

  1. customIn a 500-ml three-necked round-bottomed flask equipped with a magnetic stirrer, condenser
  2. temperatureheated
  3. temperatureat reflux for 48 hours
  4. customThe cooled reaction mixture
  5. additionwas poured slowly
  6. distillationinto distilled water (200 ml)
  7. stirringbeing agitated in an air-driven blender
  8. customThe white precipitate was collected on a Buchner funnel
  9. customsucked dry
  10. customvacuum-dried at 50°C

Sources & evidence

ORD record
ord-a3cef5c8a84c4597906dbd468590e5f8
Source dataset
uspto-grants-1976_08
Patent number
US03978156

Reaction notes

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