Acrylamide → Acrylic acid n-decylacrylate acrylamide
Reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[CH2:6]([O:16][C:17](=[O:20])[CH:18]=[CH2:19])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[C:21]([NH2:25])(=[O:24])[CH:22]=[CH2:23]>O1CCOCC1>[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[CH2:6]([O:16][C:17](=[O:20])[CH:18]=[CH2:19])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[C:21]([NH2:25])(=[O:24])[CH:22]=[CH2:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A solution was prepared of acrylic acid (10.0 g, 133 mmol), n-decylacrylate (3.0 g, 14.2 mmol) and acrylamide (3.0 g, 42.2 mmol) in dioxane (200 mL). After the solution was degassed with a rapid stream of nitrogen, AIBN (1.3 g) was added. The solution was degassed for a further thirty minutes and the reaction was then heated to 70° C. for 17 h. The polymer precipitated as a fibrous white solid as the reaction proceeded. The solution was cooled and the dioxane decanted. The residue was washed with ethyl acetate (600 mL) and the ethyl acetate was discarded. The polymer was finally washed with hexanes (300 mL) and dried in vacuo.
Workup
- customAfter the solution was degassed with a rapid stream of nitrogen, AIBN (1.3 g)
- additionwas added
- customThe solution was degassed for a further thirty minutes
- customThe polymer precipitated as a fibrous white solid as the reaction
- temperatureThe solution was cooled
- customthe dioxane decanted
- washThe residue was washed with ethyl acetate (600 mL)
- washThe polymer was finally washed with hexanes (300 mL)
- customdried in vacuo
Sources & evidence
- ORD record
- ord-af141b3ecc5a4834a4476325c275f287
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06890523B2
Reaction notes
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