42 TroceecUngs of the Royal Irish Academy. 



Distillation of Amylammonium Miicate. 



Like its congeners, this salt is easily prepared by bringing together 

 an aqueous solution of amylamine® and mucic acid. On evaporation, 

 it is obtained as a confusedlj" crystalline mass, exceedingly soluble in 

 A^'ater and alcohol, and difficult to obtain in well-defined crystals. I have 

 therefore not examined it particularly, but have submitted the salt, after 

 thorough drying on the water bath, to distillation. This was conducted 

 as already described, but towards the close of the operation the bath was 

 allowed to attain a temperature of 200° C, although this was by no 

 means necessary for the decomposition, which took place between 160° 

 and 180°. The distillate was chiefly water, holding in solution 

 amylammonium carbonate, on the surface of which floated a small 

 quantity of a very agreeably-smelling oU, which was separated, puri- 

 fied, and dried, as described for ethyl-pyrrol. When distilled, it 

 commenced to boil at 179° C. : the thermometer rose quickly to 

 188° C, when nothing more came over. On cooliug, the residue 

 solidified. The liquid which passed over between 179°-188°C., after 

 standing for some days, deposited a few needles, and on redistillation 

 again gave a residue which solidified. To free it from this crystalline 

 body the rectification had to be many times repeated. Finally I 

 succeeded in isolating a colourless liquid, of a fragrant, but somewhat 

 oppressive odour. Sp. gr. (at 16° C), -8786. It boiled between 

 180° C. and 184°. Analysis yielded results agreeing with the formula 



C4H4(C,Hu)]N\ 



xi • . Calculated for 



Experiment. CiHiCCsHn)^. 



C = 78-83 78-83 



H = 11-28 . . . '. •. . 10-95. 



The yield from 25 grams, of amylamine (the quantity which I 

 employed) only equalled a few cubic centimeters. I did not, therefore, 

 make a nitrogen cletermination, the nature of the liquid being already 

 sufiiciently established. It could be no other than amyl-pyrrol. In 

 its reactions, so far as I have examined them, it resembles the methyl 

 and ethyl derivatives. It is, however, nearly insoluble in water, and 

 retains its freedom from colour for a long time. 



The residue from the distillation of the mucate consisted almost 

 entirely of diamyl-carbo-pyrrol-amide, which was indeed by far the 

 most abundant product. I did not examine it for the amyl analogue 



6 Amylamine may be most advantageously prepared by Wurtz's process from 

 cyanate of silver and amyl iodide, since Grimm has tauglit ns an easy and rapid 

 method of procuring the latter. For the preparation of cyanates, see a process which 

 I have given (" Chemical News,'' vol. xxxii. p. 99). The formation of amyl cyanate 

 and cyanurate (almost a quantitative reaction) takes place in a few hours in sealed 

 tubes at 160° C. I have also found that amyl bromide, contrary to what is usually 

 stated, when digested with alcoholic ammonia for a coiiple of days at 100° C, 

 furnishes a considerable quantity of the primai-y amine. 



