Nitrogen bases from California gas-oil pressure distillate



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A review of the literature of bases from coal, bones, shale, petroleum, and protein pyrolysis is presented to signally demonstrate the paucity of present information as regards the nature of the complex parent nitrogen compounds which yield bases on heating. A comparison of bases from the several sources has indicated the importance of temperature of pyrolysis on the structure of the products formed; higher temperatures tend to give aromatic nuclei, and low temperatures yield hydrogenated nuclei. Optimum conditions for solvent extraction of acid solutions of bases have been assigned: 50-volume-percent CHCl₃ extraction of bases in 4N HCl at 25-35° is appropriate in most cases. Application of the useful method of amplified distillation has made possible (1) the isolation of pyridine, 2-methylpyridine, and 2,6-dimethylpyridine from a forerun obtained on destructively distilling cottonseed meal, and (2) the segregation from 130 cc. of tertiary bases from California gas-oil pressure distillate the following products: 2- and 4-methylpyridine, 2,4-, 2,5-, 2,6-, and 3,5-dimethylpyridine, 2,4,6- trimethylpyridine, quinoline, and 2-methylquinoline