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Synthesis of 14 C‐labelled propanesulphonates ‐ application to surfactants and hydrophilic polymers
Author(s) -
Hodgson Philip K. G.,
Tinley Edward J.
Publication year - 1985
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580220202
Subject(s) - chemistry , reagent , polymer , yield (engineering) , potassium carbonate , pulmonary surfactant , sodium hydride , sodium , base (topology) , potassium , nuclear chemistry , sodium carbonate , xylene , polymer chemistry , organic chemistry , toluene , mathematical analysis , biochemistry , materials science , mathematics , metallurgy
1,3‐[2‐ 14 C]Propanesultone was identified as a versatile reagent for the preparation of a wide range of 14 C‐labelled surfactant and hydrophilic polymer propanesulphonates in a convenient, efficient, one‐step reaction. A surfactant, sodium dinonylphenylhexaethoxy [2‐ 14 C] propanesulphonate was prepared by the reaction of the corresponding ethoxyalcohol with 1,3‐[2‐ 14 C]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 μCi/g in 52% yield. Structure was confirmed by 1 H and 13 C NMR spectroscopy. A low molecular weight hydrophilic polymer sulphonate has been prepared in radiolabelled form by the reaction of poly(vinylalcohol) MW 14,000 with 1,3‐[2‐ 14 C]‐propanesultone in dimethylsulphoxide with potassium carbonate as base at 85° for 18h. The 14 C‐labelled poly(vinylalcohol) potassium propane‐sulphonate so formed had specific activity 8.0 μCi/g and was obtained in 96% yield. The degree of propanesulphonation of polymer was 19.5%.