Hexa nitration

Di (hydroxyphenyl)-anthranone and its hexa-nitrate see Bis (hydroxyphenylanthranone and derivs 2 B147... 

H0.H2C.C=C(CHs0H)- (CH20H) HO.H2C.C=C(CH2OH)-C(CH2OH). This compd, prepd by Backer(Ref 2) and called Hexahydroxy-methyl-benzene, is a parent compd of its hexa-nitrate... 

Refs l)Beil- not found 2)H.J.Backer,Rec 54, 834(1935) CA 30,1367(1936) Benzenehexamethanol Hexanitrate (called Hexa-nitrate de Hexa-hydroxymethyl-benzene by Backer), C12Hi2NeOie mw 528.14, N 15-91%, OB to C02 -36.3%. Col crysts(from acet), mp 176.4° with de-compn expl on further heating or on impact(Ref 3). Its Q, Qe, power and temp of expln are given, in conf Ref 3- Was prepd by heating benzenehexamethanol in abs nitric acid until complete dissolution, followed by cooling... 

Sorbitol Penta nit rate (or Penta-o-nitro-D-gluci-tol). CsHeNsO 6 mw 407.20 N 17.20% OB to 0O2 — i,96% oily liq. Sol in ethanol Prepn is by adding dropwise a mixt of Sg sorbitol in 25g of coned nitric acid (d 1.52g/cc) at —10° to 50g of coned sulfuric add at —10 to —70°. The yield is 7.5g of a mixt which consists mostly of the Pentanitrate mixed with some Hexanitrate. This oily mixt which is reported erroneously as Sorbitol Hexanitrate by Davis (Ref 2) and correctly as a mixt of Penta and Hexa nitrates by Urbanski (Ref 4) is used as an additive to NG in low-freezing Dynamites Refs 1) Beil 1, <2840) 2) Davis (1943),... 

Other than those of the carboxylic type for example, a mixture of p-toluene-sulfonic acid and triduoroacetic anhydride forms sulfones by reaction with suitably activated aromatic compounds. By the same technique, the hexa-nitrate esters of o-mannitol and D-glucitol were obtained by use of solutions of fuming nitric acid in trifluoroacetic anhydride at 0°. The probable reaction mechanisms of these and other examples of the conversion of oxy acids into reactive entities have been briefly considered. ... 

Hexanitraies of hexitols show strong accepting properties 1 mole of hexa-nitrates w itli 2 nudes of TM PI), in agreement with the rule 3 ONOj groups t >r I mole of TMPD. 

It should be observed that the groups immediately surrounding the central carbon atoms in the above formula are the same, that is to say, the radicals with which they are combined are either identical such as H, and OH, or they differ but slightly in their most remote parts if then the similar groupings give rise to rotatory power in contrary directions, we see that they will compensate one another, or nearly so so that the rotatory power of the whole molecule will be nothing, or very slight. This is perhaps the explanation of the fact that the rotatory power of mannite, dulcite, and their hexa-nitrate, and hexa-acetate is so much reduced. 

Another class, the nitro-celluloses, are formed from cellulose, C 6 H 10 O 5, which forms the groundwork of all vegetable tissues. Cellulose has some of the properties of the alcohols, and forms ethereal salts when treated with nitric and sulphuric acids. The hexa-nitrate, or gun-cotton, has the formula, C 12 H 14 0 4 (0N0 2 ) 6 and collodion-cotton, pyroxylin, c., form the lower nitrates, i.e., the tetra- and penta-nitrates. These last are soluble in various solvents, such as ether-alcohol and nitro-glycerine, in which the hexa-nitrate is insoluble. They all dissolve, however, in acetone and acetic ether. 

The nitrate which goes under the name of gun-cotton is generally supposed to be the hexa-nitrate, and to contain 14.14 per cent, of nitrogen but a higher percentage than 13.7 has not been obtained from any sample. It is almost impossible (at any rate upon the manufacturing scale) to make pure hexa-nitro-cellulose or gun-cotton it is certain to contain several per cents, of the soluble forms, i.e., lower nitrates. It often contains as much as 15 or 16 per cent., and only from 13.07[A] to 13.6 per cent, of nitrogen. 

A whole series of nitrates of cellulose are supposed to exist, the highest member being the hexa-nitrate, and the lowest the mono-nitrate. Gun-cotton was at one time regarded as the tri-nitrate, and collodion-cotton as the di-nitrate and mono-nitrate, their respective formula being given as follows —... 

The penta-nitrate may be obtained in a pure state by the following process, devised by Eder —The gun-cotton is dissolved in concentrated nitric acid at 90° C., and reprecipitated by the addition of concentrated sulphuric acid. After cooling to 0° C., and mixing with a larger volume of water, the precipitated nitrate is washed with water, then with alcohol, dissolved in ether-alcohol, and again precipitated with water, when it is obtained pure. This nitrate is soluble in ether-alcohol, and slightly in acetic acid, easily in acetone, acetic ether, and methyl-alcohol, insoluble in alcohol. Strong potash (KOH) solution converts into the di-nitrate C 12 H 18 0 8 (N0 3 ) 2. The hexa-nitrate is not soluble in acetic acid or methyl-alcohol. 

As far as the manufacture of explosive bodies is concerned, the two forms of nitro-cellulose used and manufactured are gun-cotton or the hexa- nitrate (once regarded as tri-nitro-cellulose), which is also known as... 

The soluble cotton, which is a mixture of the tetra- and penta-nitrates, is soluble in ether-alcohol, and also in nitro-glycerine, and many other solvents, whereas the hexa-nitrate (gun-cotton),... 

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