Diethyl Ether → Mad heaa

HRID 405659Notes

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][CH2:17][C:18]([OH:20])=[O:19])(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH:21][CH2:22][CH2:23][NH:24][C:25](=[O:28])[CH:26]=[CH2:27].C(OCC)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][CH2:17][C:18]([OH:20])=[O:19])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:27]=[CH:26][C:25]([NH:24][CH2:23][CH2:22][OH:21])=[O:28]

Participants

Conditions

Temperature: 60 °C

Procedure

In 60.0 g of methanol were dissolved 19.14 g (67.63 mmol) of 12-methacrylamidododecanoic acid (MAD), 0.86 g (7.51 mmol) of N-hydroxyethylacrylamide (HEAA: Kohjin Co., Ltd.), and 0.33 g (1.97 mmol) of azobisisobutyronitrile (Nacalai Tesque, Inc.). Before use, azobisisobutyronitrile was recrystallized from methanol in the usual way. The solution was deaerated by bubbling argon 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 diethyl ether, and the resulting precipitate was collected by filtration under suction. After drying under reduced pressure, 16.90 g of MAD/HEAA copolymer (90/10) was obtained (yield: 84.5%).

Workup

customBefore use, azobisisobutyronitrile was recrystallized from methanol in the usual way
customby bubbling argon 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-edf1b80a6c28444db08016df6342f042
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08753686B2

Reaction notes

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