Hydrogen Peroxide → Acrylic acid hydroxyethyl acrylate

HRID 131084Notes

Reaction equation

OO.C(O)[C@@H](O)[C@H]1[O:10][C:8](=[O:9])[C:7](O)=[C:6]1O.C(O)(=O)C=C.[C:20]([O:24][CH2:25][CH2:26][OH:27])(=[O:23])[CH:21]=[CH2:22].SCCO.C(OO)(C)(C)C>O>[C:8]([OH:10])(=[O:9])[CH:7]=[CH2:6].[C:20]([O:24][CH2:25][CH2:26][OH:27])(=[O:23])[CH:21]=[CH2:22]

Participants

Conditions

Temperature: 70 °C

Procedure

An aqueous solution polymer of 70/30 glacial acrylic acid/2-hydroxyethyl acrylate (AA/2-HEA) was prepared by charging 600 g water, 5.6 g 50% hydrogen peroxide, 0.1 g DISSOLVINE 4.5% H-Fe (Akzo Nobel Chem. Inc.), and 0.055 g (based on 0.01% solids) SILQUEST A-171 silane (Crompton Corp., Greenwich, Conn.) to a reaction vessel. Mixtures of 59 g water and 5.5 g 50% hydrogen peroxide, and a mixture of 60 g water and 4 g erythorbic acid were then fed into the reaction vessel. A monomer feed of 364 g glacial acrylic acid, 156 g 2-hydroxyethyl acrylate, and 9.5 g 2-mercaptoethanol was then fed into the reaction vessel. A first mixture of 5.8 g water, 0.7 g 70% tertbutylhydrogen peroxide, 5.8 g water, and 0.48 g erythorbic acid was then added to the reaction vessel, which was maintained at 70° C. A second mixture of 5.8 g water, 0.7 g 70% tertbutylhydrogen peroxide, 5.8 g water, and 0.48 g erythorbic acid was then added to the reaction vessel, which was maintained at 70° C. A third mixture of 5.8 g water, 0.7 g 70% tertbutylhydrogen peroxide, 5.8 g water, and 0.48 g erythorbic acid was then added to the reaction vessel, which was maintained at 70° C.

Workup

additionwas then added to the reaction vessel, which
additionwas then added to the reaction vessel, which
temperaturewas maintained at 70° C
additionwas then added to the reaction vessel, which
temperaturewas maintained at 70° C.

Sources & evidence

ORD record: ord-50e797ded462444a962274b0c4b2f380
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384881B2

Reaction notes

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