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Synthesis of 14C-labelled propanesulphonates - application to surfactants and hydrophilic polymers

✍ Scribed by Philip K. G. Hodgson; Edward J. Tinley

Publisher: John Wiley and Sons
Year: 1985
Tongue: French
Weight: 293 KB
Volume: 22
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580220202

No coin nor oath required. For personal study only.

✦ Synopsis

1,3-[2-14C]Propanesultone was identified as a versatile reagent for the preparation of a wide range of 14C-labelled surfactant and hydrophilic polymer propanesulphonates in a convenient, efficient, one-step reaction. A surfactant, sodium dinonylphenylhexaethoxy[2-14C]propanesulphonate was prepared by the reaction of the corresponding ethoxyalcohol with L,3-[2-~4C)propanesultone in xylene at 140' for 2.5h using sodium hydride as base. Conversion, as measured by High Performance Liquid Chromatography, was 77%. Pure sulphonate was obtained after silica gel column chromatography at specific activity 31.5 PCi/g in 52% yield. Structure was confirmed by lH and 13C NMR spectroscopy. A low molecular weight hydrophilic polymer sulphonate has been prepared in radiolabelled form by the reaction of poly(vinylalcoho1) MW 14,000 with 1,3-[2-14C]propanesultone in dimethylsulphoxide with potassium carbonate as base at 85" for 18h.

sulphonate so formed had specific activity 8.0 pCi/g and was obtained in 96% yield.

The I4C-labelled poly( vinylalcohol) potassium propane-The degree of propanesulphonation of polymer was 19.5%.

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