The origin of nitriles in shale oil

Because nitriles are unlikely to occur naturally in a geological environment but have been reported as being present in some shale oils their origin was investigated. A careful infrared study could find no trace of the nitriles in the shale but it was shown, by infrared and gas chromatography with a nitrogen sensitive detector, that they do occur in some but not all oils. They are formed in the pyrolysis process by the reaction of carboxylic acids and ammonia liberated from minerals such as ammonium feldspars present in the shale. If both species are not present nitriles are not formed in the product oil. Pyrolysis of a brown coal, Loy Yang, in the presence of ammonia produced nitriles but none were generated when a more mature coal (Metropolitan) was similarly treated.