482 . REPORT—1868. 
31. To illustrate this, let us take the case of malic acid, C,H, 0,. If 
both the basic and typical hydrogen be replaced by sodium, we get a salt, 
C,H, Na, O,, which contains 34-5 per cent. sodium. If the sodium in this 
compound were removed by oxalic acid, and the acid again neutralized, we 
should get the normal salt, C, H, Na, O,, which only contains 25:84 per cent. 
Na. The compound C,H, Na, 0, loses, it will be observed, one-third of its 
sodium when converted into the normal salt, C, H, Na, O,. 
Again, C,H, Na, O,, disodium glycollate, contains 38-33 per cent. Na. If 
converted into. C, H, Na O,, it would lose one-half of its sodium, and then 
contain only 23: 47 per cent. sodium. 
As another example, C, H, Na, O,, trisodium racemate, contains 31-94 per 
cent. Na, but the normal salt, C, ‘H ’ "N a, O,, only contains 23-71 per cent. Na. 
32. Now we found that the liberated ‘acids required for neutralization 
-3059 grm. Na, and the residue on evaporation was 1:2185 grm. Hence the 
residue eontained 25-1 per cent. Na. This residue is, moreover, nearly in- 
soluble in alcohol of 80 per cent. Hence, by liberating the acids from the 
sodium-salts, soluble in 80 per cent. alcohol, and again neutralizing, they 
are converted into salts insoluble in 80 per cent. alcohol, and the percentage 
of sodium is reduced from 33°66 to 25-1. 
33. In the above experiment, the original quantity of sodium in the salts 
was ‘4689, and the loss of sodium, as before stated, was ‘163 grm. 
“4689 
Now, 163 = 
The salts thus lose nearly one-third of their sodium. It does not follow 
from this, however, that the acids are principally dibasic and triatomic acids ; 
for I have found the product of the reaction to be a very complex mixture, and 
therefore the mean loss of more than one-third of the sodium might result in 
a large number of ways from mixtures of sodium-salts of acids having a greater 
atomicity than basicity. 
34. An aqueous solution of the salts soluble in 80 per cent. alcohol ac- 
quires, on evaporation, an alkaline reaction, owing to the formation of caustic 
soda, and the residue is not entirely soluble in 80 per cent. alcohol. Pro- 
bably the whole of the synthetically formed salts are originally soluble in 
80 per cent. alcohol, but, as might be expected from their containing more 
than a normal quantity of sodium, are partially decomposed by evaporation 
into caustic soda and salts insoluble in 80 per cent. alcohol, or into oxalate 
of sodium and the same salts by the addition of more oxalic acid than is 
sufficient to decompose the ethylcarbonate. 
35. In previous Reports to the Association, I showed that formic acid is 
one of the volatile acids. It is not, however, the only one, as the following 
results prove. 
Part of the volatile acids distilled over with the alcohol at 200° F. The 
distillate required for neutralization 8-85 cub. centims. standard caustic soda or 
-2035 grm. Na. ‘The residue, on evaporation, was ‘61 grm., which therefore 
contained 33°36 per cent. Na. This result is confirmed by the following 
analysis: -1614 grm. of the residue gave ‘166 grm. Na, SO,, or -0538 Na. 
The residue therefore contained 33:32 per cent. Na, and was therefore nearly 
pure formiate, which contains 33-82 per cent. sodium, 
The volatile acids which distilled above 200° F. required, for neutralization, 
47-05 cub. centims. caustic soda, or 1082 Na. The residue, on evaporation, 
was 3:466 grms., which therefore contained 31:22 per cent. Na, which is 2-6 
per cent. less than in formiate. 
= 2°88, which is nearly 3. 
