2-Ethylhexyl acrylate → MAU 2-ethylhexyl acrylate

HRID 405654Notes

Reaction equation

HRID 405654 reaction equation
[C:1]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:20]([O:24][CH2:25][CH:26]([CH2:31][CH3:32])[CH2:27][CH2:28][CH2:29][CH3:30])(=[O:23])[CH:21]=[CH2:22].C(OCC)(=O)C>CO.N(C(C)(C)C#N)=NC(C)(C)C#N>[C:1]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:20]([O:24][CH2:25][CH:26]([CH2:31][CH3:32])[CH2:27][CH2:28][CH2:29][CH3:30])(=[O:23])[CH:21]=[CH2:22]

Participants

6

Reactant 3

HCID 76362-Ethylhexyl acrylateHCID 8857Ethyl AcetateHCID 276418511-(Methacryloylamino)undecanoic acid

Product 1

HCID 131731613MAU 2-ethylhexyl acrylateYield 373.9%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

In 59.69 g of methanol were dissolved 18.59 g (69.02 mmol) of 11-methacrylamidoundecanoic acid (MAU), 1.41 g (7.67 mmol) of 2-ethylhexyl acrylate (Sigma-Aldrich Japan K.K.), and 0.31 g (1.89 mmol) of azobisisobutyronitrile (Nacalai Tesque, Inc.). The solution was deaerated by bubbling nitrogen for 60 minutes. The container was covered with a septum, and the polymerization was conducted by heating at 60° C. for 20 hours. After the completion of the polymerization reaction, yellow candy-like material was obtained. To this was added 80 g of methanol, and the material was dissolved. The obtained solution was dropwise added into a large excess of ethyl acetate, and the resulting precipitate was collected by filtration under suction. After drying under reduced pressure, 13.01 g of random MAU/2-ethylhexyl acrylate copolymer (90/10) was obtained (yield: 65.0%). The weight average molecular weight was 560000.

Workup

  1. customby bubbling nitrogen for 60 minutes
  2. customAfter the completion of the polymerization reaction
  3. customyellow candy-like material was obtained
  4. dissolutionthe material was dissolved
  5. filtrationthe resulting precipitate was collected by filtration under suction
  6. customAfter drying under reduced pressure

Sources & evidence

ORD record
ord-a6b97ae5384542c0a22d1ec678ef1b79
Source dataset
uspto-grants-2014_06
Patent number
US08753686B2

Reaction notes

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