Tartaric acid dinitrate

Nitro-toluol, n. nitrotoluene. -verbindung, /. nitro compound, -weinsaure, /. nitrotar-taric acid (tartaric acid dinitrate, also the mononitrate), -zelluloselack, m. nitrocellulose lacquer or dope. 

N, N -Dinitro -N, N -dime thy 1 diamin o tartaric acid dinitrate 5 D1334... 

Lg-Tartaric Acid Dinitrate (Nitrotartaric acid or Dinitrotartaric acid. H02C.CH(0.N02)-CH(0.N02).C02H mw 192.06 N 14.59% OB to C02 0% v unstable and hygr silk-like ndles,... 

While the neutralization is in progress, a solution of hexamethylenetetramine (Note 8) is prepared by the cautious addition of 520 cc. of formalin (sp. gr. 1.08 approximately 7 moles) to 500 cc. of ammonium hydroxide (sp. gr. 0.90 approximately 7.5 moles). The temperature must be maintained below 20° by external cooling with ice water. The solution is finally chilled to 0° and added dropwise to the cold ammoniacal solution of tartaric acid dinitrate the temperature should not exceed 2°. The addition requires half an hour. Stirring is then discontinued, and the mixture is allowed to stand overnight. During this period the cooling bath and the reaction mixture come to room temperature. 

In a 2-1. three-necked, round-bottomed flask fitted with a thermometer, mechanical stirrer, and 1-1. dropping funnel is placed 200 g. (1.33 moles) of powdered d-tartaric acid (Note 1). To this are added, successively, 432 cc. of nitric acid (sp. gr. 1.42) and 432 cc. of fuming nitric acid (sp. gr. 1.50). The mixture is stirred until the tartaric acid is all, or nearly all, in solution (five to ten minutes) (Note 2). Then 800 cc. of concentrated sulfuric acid (sp. gr. 1.84) is slowly added from the dropping funnel. As soon as the temperature of the reaction mixture reaches 38°, the flask is surrounded by a vessel of ice water, and the rate of addition of acid is regulated so that the temperature is maintained at 38-43° (Note 3). Near the end of the addition (about fifteen minutes), tartaric acid dinitrate sometimes begins to crystallize. After all the sulfuric acid has been added the mixture is allowed to stand in a cool (20-25°) place for three hours. 

At lower temperatures tartaric acid dinitrate separates during the addition of the sulfuric acid. Under these conditions, it forms very fine crystals that are not easily filtered. 

The old Maquenne synthesis of imidazoles [64] is seldom used nowadays. It was originally used to make imidazole-4,5-dicarboxylic acids from tartaric acid dinitrate and either an aliphatic aldehyde or formaldehyde precursor in the presence of ammonium ions at pH 3.5-6.5. The procedure is not an entirely pleasant experience, and has been happily superseded by other approaches, but it may be useful on occasion to make compounds such as vinyl-, hydroxy-and methoxy-substituted 2-arylimidazole-4,5-dicarboxylic acids [65]. Use of dialkyltartrate dinitrates gives the corresponding imidazole-4,5-dicarboxylates in 45-65% yields [31]. 

Gibson reported that dinitrogen pentoxide is useful for esterifying carbohydrates and similar compounds. By keeping a mixture of tartaric acid and the pentoxide in a vacuum desiccator over sodium hydroxide, tartaric acid dinitrate was obtained. Similarly, galactaric (mucic) acid was converted into its tetranitrate, whereas, during treatment with mixed nitric and sulfuric acids, unreacted mucic acid separated from the reaction solution. 

Cyclization—Cunlinued tartaric acid dinitrate to imidazolc-... 

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