402 Dr. Harden and Mr. Walpole. Chemical Action of [Dec. 5. 



of the whole amount and has the composition of the diphenylurethane of 

 butyleneglycol (C 4 H 10 O2.2C 6 H 5 NCO) :— 



Analysis. 



Found. Calculated. 



C 6579 65-85 



H 6-21 609 



N 8-57 8-53 



It is sparingly soluble in cold alcohol, ether and benzene, crystallises in 

 rosettes of needles and melts at 197° to 198° (uncorr.). When the methane 

 is boiled with baryta water or caustic soda solution it is decomposed and 

 yields a glycol boiling at about the same temperature as the original material. 

 This glycol has, however, not yet been isolated in the perfectly pure and dry 

 state. A monourethane, CJIioO^CeHsNCO, has also been prepared winch is 

 somewhat more soluble in cold alcohol than the diurethane, and crystallises- 

 in needles, melting at 100°:— 



Analysis. 



Found. Calculated. 

 N 6-89 6-65 



2. Both the crude glycol and that recovered from the diurethane are con- 

 verted by oxidation with bromine in the light* into diacetyl,CH 3 .CO.CO.CH3 

 which was recognised by its extremely characteristic appearance and smell, 

 and by the formation of a phenylosazone melting at 242° to 242 0- 8 (uncorr. 

 The formation of this substance shows conclusively that 2 : 3-butyleneglycol 

 must be present in the fermentation product. 



Detection of Acetyl mcthylcarbi/wl among the Fermentation Products. — It was 

 further found that the distillate from the liquid in which the organism was 

 grown reduced Fehling's solution in the cold and gave with phenylhydrazine 

 the osazone of diacetyl, melting at 243°. These properties point to the- 

 presence in the distillate of acetylmethylcarbinol, CH 3 .CO.CH(OH).CII 3 , 

 which has previously been detected in this way by Grimbert^: and by 

 Desmots§ in the products of the fermentation of glucose by several bacteria :. 

 B. tartricus, B. mcscntcricus vulgatus, B. fuscus, B. flavus, B. nigcr, 

 B. ruber, B. subtilis, and Tyrothrix tenuis. It has also been found in 

 vinegar. 



This compound appears only to be formed in very small amount. Since it 



* v. Pecliniann, ' Ber.,' 1890, vol. 23, p. 2427. 

 t v. Pechmann, ' Ber.,' 1888, vol. 21, p. 2754. 

 % 'Compt. Eend.,' 1901, vol. 132, p. 706. 

 § 'Compt. Eend.,' 1904, vol. 138, p. 581. 



