Acetic Acid → Prop-2-enimidic acid--2-(dimethylamino)ethyl 2-methylprop-2-enoate (1/1)

HRID 904276Notes

Reaction equation

HRID 904276 reaction equation
C(O)(=O)C.[C:5]([O:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])(=[O:9])[C:6]([CH3:8])=[CH2:7].[C:16]([NH2:20])(=[O:19])[CH:17]=[CH2:18].CCCCCCCC/C=C\CCCCCCCC(OCC(O)[C@H]1OC[C@H](O)[C@H]1O)=O>O>[C:16]([NH2:20])(=[O:19])[CH:17]=[CH2:18].[CH3:8][C:6]([C:5]([O:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[O:9])=[CH2:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6579AcrylamideHCID 17869(Dimethylamino)ethyl methacrylateHCID 70693544Span #80 (Sorbitan monooleate)

Product 1

HCID 160008Prop-2-enimidic acid--2-(dimethylamino)ethyl 2-methylprop-2-enoate (1/1)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 41.9 grams of glacial acetic acid in 350 grams of tap water is added 109.6 grams of dimethylaminoethyl methacrylate (DMAEMA), followed by 148.7 grams of acrylamide (AM). The monomer solution pH is 7.0. It is added slowly to a rapidly stirred solution of 30 grams of sorbitan monooleate (SMO) in 320 grams of Shellflex 131. The resulting emulsion is sparged with nitrogen, warmed to 50° C. and treated with a solution 0.10 grams of bis azoisobutyronitrile (DuPont VAZO) in 2 milliliters of benzene. The polymerization began after a 30 minute induction period. Samples are withdrawn every hour and the residual monomer content determined by gas-liquid chromatography. After 5 hours the DMAEMA had completely disappeared and 20% of the acrylamide was recovered by GLC. This indicates that ≈ 60% of the DMAEMA has been quaternized by the acrylamide. A small portion of the monomer solution was stored at 25° C. for 24 hours. The NMR spectrum showed that 50% of the DMAEMA had been quaternized.

Workup

  1. customThe resulting emulsion is sparged with nitrogen
  2. additiontreated with a solution 0.10 grams of bis azoisobutyronitrile (DuPont VAZO) in 2 milliliters of benzene
  3. customSamples are withdrawn every hour
  4. waitAfter 5 hours the DMAEMA had completely disappeared
  5. custom20% of the acrylamide was recovered by GLC
  6. waitA small portion of the monomer solution was stored at 25° C. for 24 hours

Sources & evidence

ORD record
ord-7227cd480f58417a9ee3981024f89380
Source dataset
uspto-grants-1980_10
Patent number
US04230839

Reaction notes

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