Storage time and deodorization temperature influence the formation of aniline-derived compounds in denatured rapeseed oils.
In 1981 an epidemic, named Toxic Oil Syndrome, occurred in Spain as a result of ingestion of rapeseed oil denatured with 2% aniline, which had been imported for industrial use but was fraudulently diverted and processed for human consumption. Two groups of chemical compounds have been identified in the ingested toxic oil: fatty acid anilides and amino-propanediol derivatives. The objective of this work was to assess the effect of several refining process variables on the formation of 3-(N-phenylamino)-1,2-propanediol (PAP) esters. The amount of PAP esters in aniline-denatured oil increased dramatically when oil was heated from 250 degrees C to 300 degrees C. However, the ones formed when 300 degrees C was reached were lost during processing at that temperature. The level maintained during the operation time at 300 degrees C was higher in denatured samples stored for 3 weeks before refining than in denatured samples stored only for 1 week. Anilides were also analyzed. We found that anilides decreased very little with distillation time. In this paper we discuss the influence of storage time prior to refining and of elevated refining temperature, such as temperatures that might occur in close proximity to a deodorizer coil.
Ruiz-Méndez
M V
MV
Instituto de la Grasa. C.S.I.C.-Avda P. García Tejero, 4-41012, Seville, Spain. mvruiz@cica.es
Posada de la Paz
M
M
Abian
J
J
Calaf
R E
RE
Blount
B
B
Castro-Molero
N
N
Philen
R
R
Gelpí
E
E
D000814:Aniline Compounds / Q000737:chemistry / Q000633:toxicity*; D001937:Brassica; D002273:Carcinogens / Q000032:analysis; D004952:Esters; D005227:Fatty Acids / Q000378:metabolism; D005229:Fatty Acids, Monounsaturated; D005511:Food Handling; D006801:Humans; D010938:Plant Oils / Q000737:chemistry* / Q000633:toxicity; D011409:Propylene Glycols / Q000032:analysis* / Q000737:chemistry; D000074262:Rapeseed Oil; D013030:Spain; D013577:Syndrome; D013696:Temperature
D000814:Aniline Compounds; D002273:Carcinogens; D004952:Esters; D005227:Fatty Acids; D005229:Fatty Acids, Monounsaturated; D010938:Plant Oils; D011409:Propylene Glycols; D000074262:Rapeseed Oil; C092835:3-(N-phenylamino)-1,2-propanediol 1,2-dioleoyl ester