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A method for preparing sodium acrylate‐ d 3 , a useful and stable precursor for deuterated acrylic monomers
Author(s) -
Yang Jun,
Hong Kunlun,
Bonnesen Peter V.
Publication year - 2011
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.1915
Subject(s) - chemistry , acrylate , sodium , yield (engineering) , acrylic acid , monomer , catalysis , deuterium , alkyne , polymer chemistry , nuclear chemistry , organic chemistry , polymer , materials science , metallurgy , physics , quantum mechanics
A convenient and economical method for converting propiolic acid to sodium acrylate‐ d 3 is described. Successive D/H exchange of the alkyne proton of sodium propiolate (prepared from propiolic acid) using D 2 O affords sodium propiolate‐ d having up to 99 at.% D. Sodium propiolate‐ d can be partially reduced to sodium acrylate‐ d 3 with 90% conversion and 89% yield using D 2 and the Lindlar catalyst, with control of reaction parameters to maximize conversion while minimizing over‐reduction. Copyright © 2011 John Wiley & Sons, Ltd.