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Alkaline cleavage of hydroxy unsaturated fatty acids and derivatives. II 10‐hydroxydecanoic acid from ricinoleates and 1,10‐decanediol from ricmoleyl alcohol
Author(s) -
Diamond M. J.,
Applewhite T. H.
Publication year - 1967
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02680037
Subject(s) - sebacic acid , alcohol , organic chemistry , chemistry , azelaic acid , boiling point , solvent , cleavage (geology) , ethanol , primary (astronomy) , yield (engineering) , fatty alcohol , methanol , materials science , metallurgy , physics , astronomy , fracture (geology) , composite material
The 10‐hydroxydecanoic acid is formed in good yield when raw castor oil or methyl ricinoleate is fused with alkali in the presence of a high‐boiling unhindered primary or secondary alcohol at 185–195C bath temperature. When non‐reducing solvents or hindered alcohols are used, large amounts of sebacic acid form. Iso‐octanol (mixed isomers) is a suitable and potentially economical medium for producing high yields of 10‐hydroxydecanoic acid. Cleavage of ricinoleyl alcohol produces 1,10‐decanediol.