In 1981, toxic oil syndrome, a progressive multi-system disease caused by c
onsumption of rapeseed oil denatured with aniline occurred in Spain. To dat
e, the causal toxic agent or agents remain unknown. Measures of acidity, mo
isture, impurities, phosphorous, soaps, and spectrophotometric determinatio
ns of color at 409 nm were performed. Since fatty acid anilide concentratio
ns in these oils are associated with risk of disease, we studied the format
ion of aniline-derived compounds over time after oil denaturation and by oi
l deodorization temperatures (200 degreesC, 215 degreesC, 230 degreesC, 245
degreesC, 260 degreesC, y 270 degreesC) and times (3, 4, 4.5, 5, 5.5 and 6
hours). Formation of fatty acid anilide compounds increased with storage t
ime. Deodorization led to a reduction of total anilides in all the samples,
particularly at temperatures above 245 degreesC. Esters of 3-(N-phenylamin
o)-1,2-propanediol were not detected.