Styrene → 4-Vinylphenol

HRID 1865145Notes

Reaction equation

S(OOS([O-])(=O)=O)([O-])(=O)=[O:2].[K+].[K+].[CH2:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[OH-].[K+]>[CH2:13]=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([OH:2])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 65 °C

Procedure

50.0 g of 20 percent poly(4-vinylpyridine) methanol solution from Ex. 1 (˜10.0 g of polymer) was placed in a 500 ml single neck flask and stripped of solvent on a rotary evaporator. To the dried polymer was then added 110 g of RO water and 10.0 g of con. hydrochloric acid. The mixture was stirred until a uniform pale yellow aqueous solution was obtained. This solution was then charged into a 500 ml three-necked round bottom flask equipped with a mechanical paddle stirrer, a nitrogen inlet, a pot thermometer, heating mantle and condenser. 0.6 g of potassium persulfate was then added followed by 30.0 g (˜0.288 moles) of styrene. The biphasic stirred mixture was then rapidly heated to 65° C. under nitrogen for 8 hrs. The final latex solids were determined to be 26.7 percent (theory 27.1 percent) or 98.5 percent conversion. A small portion of the final latex was coagulated in dilute potassium hydroxide solution for analysis. NMR indicated a composition of 25.8 percent poly(4-VP) and 74.2 percent polystyrene (theory 25 percent poly(4-VP) and 75 percent PS). Latex particle size was ˜182 nm.

Workup

customstripped of solvent on a rotary evaporator
additionTo the dried polymer was then added 110 g of RO water and 10.0 g of con
customwas obtained
additionThis solution was then charged into a 500 ml three-necked round bottom flask
customequipped with a mechanical paddle stirrer, a nitrogen inlet
temperaturea pot thermometer, heating mantle and condenser
stirringThe biphasic stirred mixture

Sources & evidence

ORD record: ord-ae9820109b274941a618135e3a536272
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625985B1

Reaction notes

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