Nitrates of sugars

Pel Her Resine Explosible. A Fr expl invented in 1886, with a brownish color, resembling a resin in appearance. It was prepd by the nitration of sugar with mixed nitric-sulfuric acids Ref Daniel (1902), 603... 

The nitration of sugars was also studied by Hlasiewetz and Pfaundler [4], Lea [5], Colley [6], Elliott [7], Ge [8], E. J. Hoffinan and Hawse [9], Pictet et cd. [10, 11], and a number of authors whose studies are mentioned later. The most noteworthy of the earlier results, mainly those of Will and Lenze [1], are collected in Table 109. 

According to the recent experiments of Fleury, Brissaud and Lhoste [12J, the nitration of sugars can be carried out at a temperature of about 0°C by means of a mixture prepared from 2 parts anhydrous nitric add, 1 part acetic anhydride and 1 part acetic acid. A quantitive yield is thus achieved. Further, crystallization of the products is achieved more easily than with esters obtained by nitration with nitric and sulphuric acid. 

A new series of organic nitrates was discovered during the late 1930s. Among these, nitrates of sugar alcohols and their anhydrides (e.g., isosorbide dinitrate ... 

The use by T. B. Clark of dinitrogen pentoxide in dry chloroform to prepare nitrates of sugar derivatives was reported in 1934, but the method was in common use in the St. Andrews laboratories before then and was really introduced by J. W. H. Oldham. With this reagent, 1,2 4,5-di-0-isopropylidene-D-fructose is converted into its 3-nitrate, and methyl... 

Nitroline. An expl prepd by the nitration of stearin (12p) and sugar syrup (15p) with nitric (80p) and sulfuric (170p) acids. It was used in compound expls called Vigorine of Vigor ite, patented in Engl in 1875 ... 

Polyhydric Alcohols. (Polyols). An alcohol with three or more hydroxyl groups, each attached to a different carbon atom. They are w-sol and of sweetish taste, which tends to intensify with increasing hydroxyl content. Examples of polyols of ordn interest are listed below. Polyvinyl alcohol is considered in a separate entry as a polymer although it is defined as a polyhydric alcohol. Polyols, when nitrated, make excellent expls, proplnt binders, plasticizers, etc. Prepn can follow the procedure of Lenth DuPuis (Ref 3) which uses a methanol suspension of either sucrose or dextrose and a special Cu-Al oxide catalyst to yield 60-65% distillable polyols at 240° and 1500psi Refs 1) Beil — refs found under individual compds 2) CA, under Alcohols, Polyhydric for compds of current ordn interest 3) C.W. Lenth R.N. DuPuis, "Polyhydric Alcohol Production by Hydrogenolysis of Sugars in the Presence of Copper-Aluminum Oxide , IEC 37, 152-57 (1945) CA 39, 1391 (1945)... 

Howden Dynamite. A mixture compounded in 1870 in San Francisco by J. Howden and consisting of NG 75 absorbed in a mixture of sugar, magnesium carbonate and potassium nitrate. This Dynamite was stronger and better than Nobel s Kieselguhr Dynamite Ref Blasters Handbook (1952), p 5 (1958)... 

Kolf in 1890 for use as a smokeless proplnt, but also suitable as a blasting expl. It was prepd by nitration of residues from flour mills, starch and sugar plants, distilleries, breweries, etc. Oil cakes, moss, and pine needles were also nitrated. The resulting nitrated substances were treated under 5 atm press with sulfides or polysulfides, and then mixed with saltpeter previously saturated with Nitrobenzene Refs 1) Daniel (1902), 394 2) Fedoroff... 

Glucosides, Nitration Studies were conducted during WWII by MX. Wolfrom. and described in OSRD 147 or PBA 31201(1941), entitled "The Preparation of Sugar Alcohols and Glucosides for Nitration Studies ... 

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). 

Eisler (Poudre). A mining explosive consisting of Na nitrate, sulfur sugar Refs 1) Daniel (190 2), 238 2) Molina... 

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