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Synthesis of 14 C‐labeled perfluorooctanoic and perfluorodecanoic acids; purification of perfluorodecanoic acid
Author(s) -
Reich Ieva L.,
Reich Hans J.,
Menahan Lawrence A.,
Peterson Richard E.
Publication year - 1987
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.2580241011
Subject(s) - chemistry , perfluorooctanoic acid , potassium hydroxide , yield (engineering) , potassium carbonate , decanoic acid , carbonation , hydroxide , nuclear chemistry , organic chemistry , radiochemistry , environmental chemistry , metallurgy , materials science
Perfluoro‐ n ‐octaboic acid (PFOA) and perfluoro‐ n ‐decanoic acid (PFDA), two widely used industrial products, have been synthesized with 14 C‐labeling in the C‐1 position. The carboxyl labeled materials were prepared in 48% and 53% yield by carbonation of perfluoroheptyllithium and perfluorononyllithium at −100°C. An efficient chemical method for purification of PFDA was also developed. Treatment of commercial PFDA with refluxing potassium hydroxide solution resulted in removal of the mono and diprotio impurities to give 99% pure PFDA.