Toluene → Styrene

HRID 1704780Notes

Reaction equation

[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:8]([C:15](C)(C)[C:16]#[N:17])=N[C:10](C)(C)C#N>CO>[CH:1]([C:7]1[NH:8][CH2:15][CH2:16][N:17]=1)=[CH2:6].[CH2:10]=[CH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 17.0 parts 2-vinyl-2-imidazoline, 43.0 parts of styrene and 140.0 parts of toluene is prepared in a suitable polymerization vessel equipped with means for stirring and deaeration and temperature controls. After deaeration for 1 hour with a stream of nitrogen, the temperature is raised to 60° C. and polymerization is initiated by the addition of 100 ppm (based on total weight of imidazoline) of azobisisobutyronitrile as a 1.0% solution is methanol. After allowing the polymerization to proceed overnight at a temperature of 60°-70° C., the polymer is precipitated from the resulting viscous solution by pouring it into an excess of methanol with vigorous stirring. The resultant yellowish colored polymer is redissolved in toluene and then reprecipitated once more by pouring into methanol. IR and NMR analysis of dried polymer show about 75 mole percent styrene and 25 mole percent 2-vinyl-2-imidazoline incorporated into the copolymer. A sample of the polymer is an effective sizing agent for 50/50 Albacel-Astracel pulp (bleached hardwood-softwood Kraft pulp).

Workup

customequipped with means
custompolymerization
customthe polymerization
waitto proceed overnight at a temperature of 60°-70° C.
customthe polymer is precipitated from the resulting viscous solution
additionby pouring it into an excess of methanol with vigorous stirring
dissolutionThe resultant yellowish colored polymer is redissolved in toluene
customreprecipitated once more
additionby pouring into methanol

Sources & evidence

ORD record: ord-b8d733424c4e420cab496975cde428a6
Source dataset: uspto-grants-1978_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04127719

Reaction notes

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