Journal of The Japan Petroleum Institute
Print ISSN : 0582-4664
Hydrodenitrogenation of Aniline Derivatives (Part 2)
Analysis of Mass Spectra of Addition Products
Yasuo MIKIYoshikazu SUGIMOTO
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1998 Volume 41 Issue 2 Pages 92-97

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Abstract
The mass spectra of addition products formed in hydrodenitrogenation of 2-propylaniline, N-propylaniline, and 3-phenylpropylamine were analyzed in connection with their structures. Most of the addition compounds were considered to substitute on the nitrogen atom.
The two major compounds from 2-propylaniline were characterized by MW of 259 and ions of m/z 174 and 146. These compounds were assigned as N-(2-propylcyclohexyl)-2-propylanilines (cis- and trans-).
Three major compounds with MW of 175, 181, and 177 were produced in the reaction of N-propylaniline. Of these compounds, two with MW of 175 and 181 were identified as N-cyclohexylaniline and dicyclohexylamine by comparing with the standard compounds. The third with MW of 177 was characterized by ions of m/z 148 and 106 that coincided with the mass spectrum of N, N-dipropylaniline.
One major compound with MW of 253 and one minor compound with MW of 259 were produced in the reaction of 3-phenylpropylamine. The former compound was characterized by ions of m/z 148 and 91 and identified as bis(3-phenylpropyl)amine, and the latter compound was characterized by ions of m/z 148 and 154 and was identified as N-(3-cyclohexylpropyl)-(3-phenylpropyl)amine.
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