Styrene → Styrene 4-vinylbenzenesulfonic acid cyclohexyl ester

HRID 495331Notes

Reaction equation

[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:9]1([O:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[CH2:26])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.N(C(C)(CC(C)C)C#N)=NC(C)(CC(C)C)C#N>C(C(C)=O)C>[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:9]1([O:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[CH2:26])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

Conditions

Temperature: 65 °C

Procedure

A three-necked flask having a capacity of 500 ml was charged with 240 g of methyl ethyl ketone and the content was stirred at 65° C. in a nitrogen gas stream. A mixture of 93.74. g of styrene, 26.64 g of 4-vinylbenzenesulfonic acid cyclohexyl ester and 1.99 g of 2,2′-azobis(2,4-dimethylvaleronitrile) was dropwise added thereto over 2 hours. After completion of the dropwise addition, 0.5 g of 2,2′-azobis(2,4-dimethylvaleronitrile) was further added, followed by stirring for further 2 hours, thereby a styrene-4-vinylbenzenesulfonic acid cyclohexyl ester copolymer was obtained. After the reaction mixture was poured into an egg-plant type flask having a capacity of 1 liter and concentrated, 300 g of MFG was added thereto, the reaction mixture was heated for 3 hours with refluxing MFG, thereby sulfonic acid cyclohexyl ester was decomposed to obtain a sulfonic acid. The obtained reaction mixture was cooled to room temperature and poured into a beaker containing 3 liters of water, thus an aqueous solution of a high molecular compound was prepared.

Workup

customA three-necked flask having
additionwas further added
stirringby stirring for further 2 hours

Sources & evidence

ORD record: ord-7f56976afb524574b67fe6ae1edfd931
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06939658B2

Reaction notes

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