Sulfuric Acid → Sodium styrenesulfonate 2-(amino)ethylmethacrylate

HRID 1193471Notes

Reaction equation

[CH:1]([S:9]([O-:12])(=[O:11])=[O:10])=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Na+:13].[NH2:14][CH2:15][CH2:16][O:17][C:18](=[O:22])[C:19]([CH3:21])=[CH2:20].S(=O)(=O)(O)O.C(ON(OC(=O)C)CCN(OC(=O)C)OC(=O)C)(=O)C.[Na].[Na]>O>[C:18]([O:17][CH2:16][CH2:15][NH2:14])(=[O:22])[C:19]([CH3:21])=[CH2:20].[CH:1]([S:9]([O-:12])(=[O:10])=[O:11])=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Na+:13]

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 35 g of sodium styrenesulfonate and 14 g of 35% 2-(amino)ethylmethacrylate.HC1 solution in 200 ml of water was prepared. The pH was adjusted to 3.5 using 1N sulfuric acid, and 0.1 g disodium ethylenediamine tetraacetate was added to the above solution. The solution was then N2 sparged for 30 minutes and heated to 65° C. 3 g of 4,4'-azobis(4-cyanovaleric acid) were then added, and the solution maintained at 65° C. for 6 hours. The reactants were poured into 1 liter of acetone, the acetone was decanted off, and methanol added. This mixture was allowed to stand overnight, followed by filtration and methanol-washing. Vacuum oven drying gave 40 g of a 11% 2-(amino)ethyl methacrylate/sodium styrenesulfonate copolymer, a white solid.

Workup

additionwas added to the above solution
customN2 sparged for 30 minutes
addition3 g of 4,4'-azobis(4-cyanovaleric acid) were then added
temperaturethe solution maintained at 65° C. for 6 hours
additionThe reactants were poured into 1 liter of acetone
customthe acetone was decanted off
additionmethanol added
filtrationfollowed by filtration and methanol-
washwashing
customVacuum oven drying

Sources & evidence

ORD record: ord-7fcdb642f9d94700980f0d5de5fd7c86
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04810624

Reaction notes

Loading…