The Chemistry of Powder and Explosives - Sciencemadness Dot Org

244 NITRIC ESTERS
d-a-Glucoheptose hexanitrate, C7H8O(ONO2)6, from the nitration
of d-a-glucoheptose, 69 crystallizes from alcohol in transparent
needles which melt at 100°. It reduces Fehling's solution
on warming.
Trehalose octonitrate, CioHuCMONO^s, from the nitration of
trehalose, 69 crystallizes from alcohol in birefringent pearly leaflets
which melt at '124° and decompose at 136°. It reduces
Fehling's solution on warming.
Raffinose hendecanitrate, Ci8H2iO5(ONO2)ii, from the nitration
of raffinose, 69 exists in the form of amorphous aggregates
which melt at 55-65° and decompose at 136°. It reduces Fehling's
solution on warming. It decomposes rapidly when kept at 50°.
ot-Tetraamylose octonitrate, [CeH8O3(ONO2)2]4, from a-tetraamylose,
76 crystallizes from acetic acid in fine glistening needles
which decompose at 204°. It is readily soluble in ethyl acetate,
amyl acetate, pyridine, and nitrobenzene, and sparingly soluble
or insoluble in alcohol, ether, benzene, and water. a-Diamylose
hexanitrate, 79 [C6H7O2(ONO2)3]2, prepared from a-diamylose or
as the final product of the nitration of tetraamylose, crystallizes
from acetone in plates which puff off at 206-207°. It is difficultly
soluble in acetic acid, and is reported to be but little stable. The
alcohol extract of the crude hexanitrate yields a certain amount
of the amorphous tetranitrateJ 6 ji-Triamylose hexanitrate, 7 *
[C6H8O3(ONO2)2]3, is procured by dissolving either /3-triamylose
or /3-hexaamylose in strong nitric acid at 0° and adding concentrated
sulfuric acid drop by drop, and extracting the crude
product with alcohol. It crystallizes from the alcoholic extract
in aggregates of microscopic cubes, m.p. 203°. The residue
which is insoluble in hot alcohol is recrystallized from acetic
acid and yields crystalline crusts of fi-triamylose enneanitrate, 7 *
[C6H7O2(ONO2)3]3, m.p. 198°.
Early History of Nitrated Carbohydrates
The history of modern explosives commenced with the discoveries
of nitroglycerin and of nitrocellulose. At about the time
that Sobrero first prepared nitroglycerin, Schonbein at Basel and
Bottger at Frankfort-on-the-Main independently of each other
nitrated cotton, perceived the possibilities in the product, and
78 Leibowitz and Silmann, Ber., 58, 1889 (1925).