Ethyl Acetate → MAU potassium 3-methacryloxypropanesulfonate

HRID 405653

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:25][CH2:26][CH2:27][CH2:28][S:29]([O-:32])(=[O:31])=[O:30])(=[O:24])[C:21]([CH3:23])=[CH2:22].[K+:33].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:25][CH2:26][CH2:27][CH2:28][S:29]([O-:32])(=[O:30])=[O:31])(=[O:24])[C:21]([CH3:23])=[CH2:22].[K+:33]

Participants

Conditions

Temperature: 60 °C

Procedure

In 59.69 g of methanol were dissolved 18.15 g (67.41 mmol) of 11-methacrylamidoundecanoic acid (MAU), 1.85 g (7.49 mmol) of potassium 3-methacryloxypropanesulfonate (Tokyo Chemical industry Co.), 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, the reaction 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, 18.47 g of random MAU/potassium 3-methacryloxypropanesulfonate copolymer (90/10) was obtained (yield: 92.4%). The weight average molecular weight was 240000.

Workup

customby bubbling nitrogen for 60 minutes
customAfter the completion of the polymerization reaction
filtrationthe resulting precipitate was collected by filtration under suction
customAfter drying under reduced pressure

Sources & evidence

ORD record: ord-afe1d64d88df42dfb71c051d1640df24
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08753686B2

Linked notes

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