Inasmuch as microscopic and X-ray examinations of the alumina catalyst showed that the laboratory-prepared alumina was more crystalline than the commercial alumina tested, it may be that the greater catalytic activity of the former is connected with its higher degree of crystallinity.The ferric chloride-Filtrol catalyst was tested at 200°( expt. 28) and at 300°( expt. 29). Hydrogen chloride was evolved initially at both temperatures but no toluene was produced. The iron in the used catalysts was at least 95% in the ferrous state. Reduction of ferric chloride catalyst in the Friedel-Crafts reaction has been previously observed. 6 The ferrous chloride-activated carbon catalyst was tested at 300°( expt.30) and at 400°( expt. 31). Toluene was not produced at either temperature. Hydrogen chloride was absent in the exit gas from the 300°e xperiment, but it was present in the 400°e xperiment.The "solid" phosphoric acid catalyst showed no activity at approximately ten seconds contact time at 300, 350, 400 and 450°. Aluminum chloride adsorbed on activated carbon was active as would be expected, but three consecutive eight-hour periods (expts. 36-A, 36-B, 36-C) at 150°showed that the activity dropped off rapidly. The higher temperatures used with the other catalysts could not be employed with the -aluminum chloride-activated carbon catalyst because of the sublimation of aluminum chloride.
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