D-Sorbitol hexanitrate

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... 

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... 

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),... 

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. 

Mannitol hexanitrate is obtained by nitration of mannitol with mixed nitric and sulfuric acids. Similarly, nitration of sorbitol using mixed acid produces the hexanitrate when the reaction is conducted at 0—3°C and at —10 to —75°C, the main product is sorbitol pentanitrate (117). Xylitol, ribitol, and L-arabinitol are converted to the pentanitrates by fuming nitric acid and acetic anhydride (118). Phosphate esters of sugar alcohols are obtained by the action of phosphorus oxychloride (119) and by alcoholysis of organic phosphates (120). The 1,6-dibenzene sulfonate of D-mannitol is obtained by the action of benzene sulfonyl chloride in pyridine at 0°C (121). To obtain 1,6-dimethanesulfonyl-D-mannitol free from anhydrides and other by-products, after similar sulfonation with methane sulfonyl chloride and pyridine the remaining hydroxyl groups are acetylated with acetic anhydride and the insoluble acetyl derivative is separated, followed by deacetylation with hydrogen chloride in methanol (122). Alkyl sulfate esters of polyhydric alcohols result from the action of sulfur trioxide—trialkyl phosphates as in the reaction of sorbitol at 34—40°C with sulfur trioxide—triethyl phosphate to form sorbitol hexa(ethylsulfate) (123). 

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. 

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