Sorbitol hexanitrate

Sorbitol hexanitrate, or nitrosorbitol, is an isomer of nitromannitol. In normal conditions it is a crystalline material melting at 55°C. It has been obtained by Berg-heim [25] and by Tettamanzi and Amaldi [26]. 

Davis [27] has described its physical state as an oily liquid, which was used in the United States as an additive to nitroglycerine in low-freezing dynamites. 

The discrepancy has been explained by the experiments of T. Urbanski and Kwiatkowska [28] who found that by dissolving sorbitol in a five-fold quantity of concentrated nitric acid (d = 1.52) at 0°C followed by precipitating the product with the help of a ten-fold amount of 20% oleum at +5°C, hexanitrate only slightly contaminated with pentanitrate was formed. When, however, the temperature of nitration and precipitation is -10°C an oily mixture of sorbitol hexa- and pen-tanitrates was produced. Most probably it was a mixture of this kind that Davis described, as sorbitol pentanitrate exists under normal conditions in the form of an oil. The explosive properties of nitrosorbitol resemble those of nitromannitol. 

Sorbitol is at present manufactured commercially by catalytic reduction of D-glucose. Hence the nitrated product may attain greater practical importance. 

5-Dinitrates of l,4 3,6-dianhydrohexitols have been prepared by Formann, Carr and Krantz [29] in an attempt to obtain vasodilatory substances. Jackson and Hayward [30] studied their chemical properties. 

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Hexanitrosorbitol. See Sorbitol Hexanitrate under Sorbitol and Derivatives... 

Sorbitol hexanitrate Monomethyl cyclohexanepentanitrate l-Methyl-3,5-dinitro-1,2,4-triazole N-Methyl gluconamide pentanitrate... 

D-Glucitol (Sorbitol or Hexanhexol), HOCH2(CHaOH)4CH2OH raw 182.17, ndls (with lA or 1 w), tnp about ll0°(dry), -100° or less (with w), very hygr when dry sol in w hot ale. Found in various fruits prepd by sodium amalgam reduction of d-sorbose or by pressure hydrogenation of dextrose with Ni catalyst. Used far prepn of ascorbic acid (Vitamin C), for synthesis of resins, surface-active agents, varnishes, syrups, cosmetic creams aod for explosive Sorbitol Hexanitrate... 

S.D. Lewis, USP 3316132(1967) CA 67, 45711g(1967) (Stable expl compn An intimate mixt of sorbitol hexanitrate 90.73... 

Na salicylate 9.27%, both.materials having a max particle size not more than 595jx, after 52 days storage at RT lost 0.19% by wt. A-nother sample of Sorbitol hexanitrate without stabilizer, similarly tested, lost 18% of its wt)... 

Nitrosorbite (Sorbitol hexanitrate) d-Sorbite occurs in the berries of the mountain ash, but is more readily procured by the electrolytic reduction of d-glucose. It crystallizes with one molecule of water in small crystals which lose their water when heated and melt at about 110°. Nitrosorbite, isomeric with nitromannite, exists as a viscous liquid and has never been obtained in the crystalline state. It is used in non-freezing dynamites. 

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),... 

Hexanitroinositol. See under Inositol and Derivatives in this Vol Hexanitrosorbitol. See Sorbitol Hexanitrate under Sorbitol and Derivatives... 

Duldtol hexanitrate ("Nitrodulcitor ) D-Sorbitol hexanitrate Dinitrates of dianhydrohexitols Polyvinyl nitrate Literature... 

Property and Preparation of Other Nitrate Esters [1, 3] 5.5.1 Property and Preparation D-Sorbitol Hexanitrate... 

Sorbitol hexanitrate, or nitro sorbitol, is one of the isomers of nitro mannitol. It is a crystalline chemical at normal condition and molten at 55 °C. It used to be an additive of nitroglycerine in the United States to prepare dynamites with a low freezing point. 

Sorbitol is dissolved to five times volume of concentrated nitric acid (d = 1.52 at 0 °C). The product can be precipitated by 10 times volume of 20 % finned sulfuric acid (5 °C). In the product, there is a small amount of impurity of pentanitrate. At 0-10 °C of nitration and precipitation temperamre, an oily mixture of sorbitol hexanitrate and sorbitol pentanitrate will be obtained. The explosion property of nitro sorbitol is similar with that of nitro mannitol. 

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