ON PROXIMATE CONSTITUENTS OF COAL. 343 
potassium permanganate, in some cases made alkaline with caustic potash, 
appeared to offer a more promising method of attack. The coal uses up 
very considerable quantities of the permanganate, and dark brown solu- 
tions are obtained. From these solutions it has been attempted, by the 
aid of the formation of insoluble salts, to isolate some of the acids which 
result from the oxidation of the coal in this way. The difficulties met 
with arising from the unsatisfactory properties of many of these salts, 
which are usually obtained in the form of gelatinous, clayey solids, difficult 
to wash and obtain in a state of purity suitable for analysis, have led to 
the abandonment of this reagent. 
More promising results have been obtained by acting upon the coal 
with dilute hydrochloric acid and potassium chlorate. Mr. J. A. Smythe, 
B.Sc. of the Durham College of Science, Newcastle-upon-Tyne, has under- 
taken the investigation of this action for the purposes of this committee. 
When finely divided coal is boiled for several hours with dilute hydro- 
chloric acid, and potassium chlorate added from time to time, the coal 
gradually assumes a brown colour, and a brown solid collects on the 
surface of the yellow liquid. The coal, after lengthened treatment, is 
filtered off, washed, and dried at 100° C. The product is invariably found 
to have increased in weight, and when extracted with alcohol or acetone 
some 30 to 35 per cent. of the material is dissolved out by either of these 
solvents ; of the two, acetone is the more powerful solvent, leaving a coal- 
like insoluble residue. The solution obtained in this manner is next dis- 
tilled, and after removal of the solvent a dark reddish brown resinous 
mass is left, which, when finely ground, forms a dark brown homogeneous 
powder. The finely divided powder was extracted with benzene ; the 
portion insoluble in benzene was treated with alcohol, in which some 
readily dissolved, leaving a residue sparingly soluble in hot alcohol. 
The benzene solution, after removal of the benzene, leaves a dark 
resinous mass, which, when ground, forms a brown powder, which is dis- 
solved not only by benzene and acetone, but also by ether, chloroform, 
glacial acetic acid, phenol, and nitrotoluene, but is insoluble in carbon 
disulphide, petroleum ether, and water. The solutions of this body are 
all dark brown, almost black, and from these it is always deposited in an 
amorphous condition. The analysis of this substance gave the following 
results, from which a formula, C3,H,,Cl,0,9, has been deduced :— 
Weight of Substance 
(a) 0°364 gram gave 0°578 gram CO,, and 0-086 gram H,0. 
07293), » O-411 ,, AgCl=34-67 per cent. Cl. 
(6) 0-357 _,, » 0571 ,, CO,, and 0-087 gram H,0. 
0:322 °.,, » 0448 ,, AgCl=34:29 per cent. Cl. 
Caleulated for 
a b Means C59 Ho2Cls0 19 
C, 43°29 - 43°60 A 43°44 ; 43 64 
H. 2°62 . 2°70 A 2°66 ‘ 3 2°66 
Cl. 34:67 4 34°42 ; 34°54 : : 34:29 
0. 19°42 5 19°28 — f 3 19°41 
TT aes ANGO. Ober weooyp fh =. hae reys glOOr00 
From the alcoholic extraction there was obtained, after removal of the 
alcohol, a brown solid, very similar in appearance to that obtained from 
