Linseed oil that has been hydrogenated to a plastic consistency is subject to a type of deterioration termed "flavour reversion" when heated to temperatures used in baking or frying. Investigation of the course of hydrogenation of linseed oil by the spectral method of Mitchell, Kraybill, and Zscheile (11) has indicated that linolenic acid is converted to an isomeric linoleic acid; this acid differs from naturally occurring linoleic acid in that the double bonds are in such positions that diene conjugation is not produced by high-temperature saponification. In a typical hydrogenation, the concentration of the isomeric acid increased to a maximum, at about iodine number 120, of 18% of the total fatty acids, and at iodine number 80, at which point the plasticity was similar to that of a commercial shortening, the concentration of the isomer was 13%. Evidence is presented that the isomeric linoleic acid in partially hydrogenated linseed oil is responsible for the unpleasant flavour that develops when the oil is heated.
Reactive molecular dynamics simulation of the high-temperature pyrolysis of 2,2′,2′′,4,4′,4′′,6,6′,6′′-nonanitro-1,1′:3′,1′′-terphenyl (NONA)
