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Methylation of indole during catalytic tests for hydrodenitrogenation (HDN) reactions

✍ Scribed by Marc Callant; Keith A. Holder; Heinz G. Viehe; Paul Grange; Bernard Delmon


Book ID
103997439
Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
721 KB
Volume
97
Category
Article
ISSN
1381-1169

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✦ Synopsis


Hydrodenitrogenation

(HDN) is a catalytic process aimed at reducing the nitrogen content of petroleum crudes. We studied the reactivity of organic nitrogen compounds, aniline and indole, representative of those present in the crudes. The catalytic tests were carried out in the presence of H,S in the reacting gas phase. It was generated in situ by adding sulphur compounds which decomposed easily to H2S and hydrocarbon. The use of CS, as H,S precursor led to the occurrence of side reactions: two methylindole isomers were identified in the indole reaction products. These side reactions were not observed with other H,S precursors like dimethyldisulphide or diethyldisulphide. We established that the formation of the methylindole isomers results from a reaction between (undecomposed) CS2 and the five-membered hetero-ring of indole or indoline and we proposed a twostep reaction mechanism.