Styrene → 4-Vinylbenzoic acid

HRID 428356

Reaction equation

HRID 428356 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C=C.C=CC1C=CC=CC=1.C(C1C=CC=CC=1[C:23]([OH:25])=[O:24])=C>C(C1C=CC=CC=1S(O)(=O)=O)CCCCCCCCCCC>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([C:23]([OH:25])=[O:24])=[CH:5][CH:4]=1)=[CH2:1]

Participants

5

Reactant 3

HCID 7501StyreneHCID 3015504Vinylbenzoic acidHCID 22558332Ethylene styrene

Product 1

HCID 140984-Vinylbenzoic acidYield 3,062.6%

Reagents, catalysts & solvents 1

HCID 25457Dodecylbenzenesulphonic acidSolvent

Procedure

40 g of an ethylene styrene interpolymer (35 wt percent Copolymer Styrene, 6.0 wt percent a tactic Polystyrene, ESI-2) was added to a Brabender mixer at 190° C. To the polymer melt, 1.2 g (8 mmol) of powdered vinylbenzoic acid was added. Finally, 107 μL of dodecylbenzenesulfonic acid was added and the molten mixture blended at 80 rpm for 5 minutes. After the allotted time, the Brabender was opened and the tan polymer melt was removed to yield 36.3 g of product. A 300 mg portion of the polymer was pressed between teflon sheets into a thin, clear, and creasable film at 210 C with 20,000 lbs of load. Analysis of the film by infrared spectroscopy showed a broad peak at 3500 to 3000 cm−1 due to the carboxylic acid group and a carbonyl stretch at 1695 cm−1. Dissolution of the polymer in warm xylene (15 mL/g of polymer) followed by precipitation into methanol did not change the IR spectrum of the product indicating that the vinylbenzoic acid was indeed grafted to the ethylene styrene copolymer and that the product was not simply a physical mixture of the two components.

Workup

  1. customthe tan polymer melt was removed

Sources & evidence

ORD record
ord-e99f42c641a949578556c87f9f924515
Source dataset
uspto-grants-2001_11
Patent number
US06313252B1

Linked notes

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