N-Methylolacrylamide → N-hydroxymethyl acrylamide dodecyl acrylate

HRID 65656

Reaction equation

[OH:1][CH2:2][NH:3][C:4](=[O:7])[CH:5]=[CH2:6].[C:8]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:11])[CH:9]=[CH2:10]>C(C(C)=O)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[OH:1][CH2:2][NH:3][C:4](=[O:7])[CH:5]=[CH2:6].[C:8]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:11])[CH:9]=[CH2:10]

Participants

Conditions

Temperature: 80 °C

Procedure

10.1 gm (0.1 mole) of N-hydroxymethyl acrylamide and 144 gm (0.6 mole) of dodecyl acrylate were dissolved in 360 gm of methyl ethyl ketone. To the solution obtained were added 3.1 gm of dibenzoyl peroxide as a catalyst. The reaction mixture was maintained for 5 hours under stirring at a temperature of 80° C. After the reaction was completed, the solvent was distilled off and the reaction product washed several times with methanol. 147 gm (95% of theory) of N-hydroxymethyl acrylamide/dodecyl acrylate copolymer (1:6 molar ratio) were obtained.

Workup

customTo the solution obtained
temperatureThe reaction mixture was maintained for 5 hours
distillationthe solvent was distilled off
washthe reaction product washed several times with methanol

Sources & evidence

ORD record: ord-c9f8f0cc0f7d41979aea8df5c5aeb86b
Source dataset: uspto-grants-1978_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04128634

Linked notes

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