Catalytic Hydrogenation of Indole in Furnace Oil: Separation and Identification of Reaction Products

Identification of Nitrogen Bases in Heavy Gas Oil; Chromatographic Methods of Separation.

“…This precipitate was of minor quantity and was easily removed by filtration. Based on previous work (10), it is believed that this precipitate contained polymerized indoles. After separation of the layers, the combined aqueous acidic phases were extracted three times with chloroform (3:1) to remove entrained oil; this extraction also removed a moderate quantity (1.148 grams) of soluble hydrochlorides of nitrogen bases (3).…”

“…Mair (7) recently identified 2,6,10-trimethylundecane and 2,6,10-trimethyldodecane in petroleum. Moore and Dunning (10) identified prophyrins in oil shale.…”

“…Reference Standards. Phytane (2,6,10, was prepared by hydrogenating phytyl alcohol (2,6,10,14-tetramethyl-2-hexadecane-l-OL) using chloroplatinic acid and sodium borohydride (4). The resulting dihydrophytol was converted to the p-tolulenesulphonate, then was reduced to phytane using lithium aluminum hydride.…”

“…This paper presents evidence for new types of basic nitrogen compounds recently isolated from a nonhydrogenated, straightrun, heavy gas oil. Earlier studies in this Laboratory (10) have shown that dilute mineral acids extract the basic nitrogen compounds from petroleum distillates. However, methods for the separation and characterization of these isolated bases are still being sought.…”

“…It is interesting that 40.3% of the total nitrogen was removed from the oil, rather than 32.7% attributed to the basic portion. This is partially due to the formation of soluble hydrochlorides of indole polymers (10). The concentrate was found to contain 90 p.p.m.…”