1910. ] B. lactis aérogenes on Glucose and Mannitol. 279 
These facts, taken together, indicate that these crystals had the com- 
position 
CisHizON2 + 2(CisHaOu.N2) = CrpHs2NeQo 
Diphenylurea Diphenylurethane Complex 
(m. pt., 235°). of 2: 3-butyleneglycol (m. pt., 187°°5). 
(mjpt:; 1995): 
The formation of the diphenylurea is doubtless partly due to moisture 
gaining access to the reaction mixture and present in the “crude glycol.” 
(3) 2:3-Butyleneglycolmonophenylurethane.—In later preparations, the 
formation of the substance was avoided by using excess of phenylisocyanate 
and continuing the heating for many hours. It resembles the diurethane 
very closely in its solubility relationships, but it is, of course, more soluble 
than this. The melting point of the pure substance recrystallised from 
alcohol was found to be 100° C., and a sample of the material treated 
with phenylisocyanate in benzene solution at its boiling point for eight 
hours gave an almost theoretical yield of the diphenylurethane (melting 
point, 199°). 
00808 grm. gave 0°1876 grm. CO, and 0°0572 grm. H20. 
02558 grm. ,, 15:00 c.c. N (moist) at 16° and 766 mm. 
Found. | Calculated C,,H,,NO3. | 
Genter ges 63 “32 63-16 | 
13 Lee eh a eae 7°86 ews 
Nips caves: 6°89 6°65 
1-2 erm. of material in 57 ¢.c. of benzene gave in a 200-mm. tube a rotation 
of +0°:004. If it is assumed that a rotation of 0°01 is detectable with 
certainty, the specific rotation for this substance in benzene solution cannot 
be greater than + 0°25. | 
Fractionation by means of Benzene and Petrolewm.—tThe alcoholic mother 
liquors from the three substances described were now concentrated and taken 
up in benzene. A collection of a quantity of this material was made, and 
then fractionation effected by precipitation with low boiling-point petroleum 
ether. After a while the mother liquors became thick, and then the 
phenylurethane formed by the reaction of phenylisocyanate and the alcohol 
added was removed by distillation 7 vacuo. The distillate, boiling at about 
120° under reduced pressure, consisted of nearly pure phenylurethane, melting 
after recrystallisation at 49°5. The value given by Paal an@ Otten* is 52°. 
* Paal and Otten, ‘ Ber.,’ vol. 23, p. 2590. 
