Premium
Hyperchlorinated fatty acids: I. Tentative methods of synthesis
Author(s) -
Chals M.,
Perron R.
Publication year - 1971
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/bf02544570
Subject(s) - stearic acid , chemistry , chlorine , yield (engineering) , solvent , mole , halogen , fatty acid , chlorine atom , organic chemistry , medicinal chemistry , materials science , alkyl , metallurgy
The hyperchlorination of fatty acids was studied by four methods using mainly stearic acid. This acid was first submitted to the action of nascent chlorine from NaCl electrolysis, for which the best results never exceeded 43% of fixed chlorine (about 6 Cl atoms per mole of acid), with a yield of 30% based on the acid. Stearic acid was also submitted to electric discharges in CCl 4 , and so transformed into various chlorinated and unsaturated compounds, which indicate a near simultaneity of chlorination and dehydrochlorination. However, when the time of contact of the acid with the reactive solution was reduced, formation of only saturated chlorinated compounds occurred, of which the chlorine content, in the best case, was 54% (9 Cl/mole). Direct photochlorination of acid without solvent gave a product containing a maximum of 8 Cl atoms per mole (about 50%). Finally, direct photochlorination of the fatty acid in CCl 4 led to a hyperchlorinated acid containing 68.3% Cl (16–17 Cl/mole), and minor, more or less polymerized products. Although the second and third methods readily afford stearic acid chlorinated to the extent of about 50%, this value, corresponding to an average of 0.5 Cl/C atom, appears to be a barrier that can only be overcome by employing photochlorination in an inert solvent, such as CCl 4 .