Decahydroquinolines, from quinoline

HDN of Quinoline. Satterfield et al.(8) proposed that there are two pathways for the HDN of the coal liquid model compound quinoline using a NiHMocatalyst. One pathway involves the successive formation from quinoline of 1,2,3,4-tetrahydroquino-line, o-propylaniline and then ammonia plus n-propylbenzene. A second pathway involves the successive formation of 5,6,7,8-tetrahydroquinoline, decahydroquinoline, propylcyclohexylamine... 

Table I gives the results from the experiments with [M(PC)] supported on Si02 The conversion of quinoline is almost exclusively to 1,2,3,4-tetrahydroquinoline with only traces of other products (<1%). No propylaniline, propylbenzene, propyl-cyclohexane, 5,6,7,8-tetrahydroquinoline or decahydroquinoline were noted. No change is noted in the conversions when the SiC>2 is activated in vacuo at 400°C prior to supporting the complex. When the hydrogenations are run at 200°C only low conversions are...

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