CELLULOSE 2 i 5 



four hydroxyl groups, whereas it is known that the highest 

 nitrate obtained from a cellulose molecule containing six 

 carbon atoms is a trinitrate. By the nitration of cellulose, it 

 is possible to obtain a whole series of esters representing 

 different degrees of nitration. These various compounds may 

 be described as mono-, di-, tri, etc., up to deca- or possibly 

 dodeka-nitrates of a cellulose molecule containing twenty-four 

 carbon atoms. What is commonly called cellulose hexa- 

 nitrate, the substance employed in the manufacture of gun- 

 cotton, is calculated on a C12 molecule which, therefore, corre- 

 sponds to a trinitrate of a Cg molecule. 



Formulae such as Green's or Vignon's receive some support 

 from the behaviour of cellulose on distillation, and from the 

 ease with which cellulose gives rise to brommethylfurfural 

 on heating with hydrobromic acid. 



On the other hand, the formula suggested by Hibbert * 

 for the cellulose nucleus brings out clearly the relationship of 

 cellulose to glucose as may be seen from a comparison of the 

 two formulae : — 



CH„OH 6CH2OH 



I I. 



CH 



CHOH 



I 

 CHOH O 



CHOH 



CHOH — 



5CH- 



-c'h 



CHOH 



O 



3 



I 

 2CHOH 



I 

 -CH 



Glucose CgH^^Ofi Hibbert's formula CgHjoOs 



Denham and Woodhouse, by exhaustive methylation of 

 cellulose and subsequent hydrolysis, were able to show that 

 2:3:6 trimethylglucose resulted, from which it would appear 

 that carbon atoms i and 5 are occupied in the original cellulose 

 molecule in uniting together the various unit groups. 



The fact that the acetolysis of cellulose gives rise to 

 cellobiose and glucose caused Irvine f and co-workers to sug- 

 gest a trisaccharide constitution for cellulose as represented 

 by the formula — 



* Hibbert : " J. Ind. Eng. Chem.," 1921, 13, 256, 334. 



t Irvine and Robertson : " J. Chem. Soc," 1926, 129, 1488. 



