Mannitol D-, hexanitrate

D-Mannitol hexanitrate, nitromannitol or nitromannite was obtained by Sobrero [10] by nitrating D-mannitol. In view of its high sensitiveness to impact and great ease of detonation Sobrero suggested that it could act as an initiator. However, experiments carried out in the arsenal at Torino, Italy, have not confirmed this. Nitromannitol has also been obtained by Domonte and Menard [11]. 

D-Mannitol hexanitrate crystallizes from ethyl alcohol in the form of needles melting at 112-113°C. Its specific gravity is 1.604. It is immiscible with water, dissolves readily in ether and hot ethanol and with difficulty in cold ethyl alcohol. With aromatic mononitro compounds, e.g. nitrobenzene, p-nitrotoluene, p-nitroanisole, a-nitronaphthalene, mannitol hexanitrate forms addition compounds melting in a non-homogeneous way, as shown by T. Urbanski [5, 6, 7, 17]. 

Selective denitration is illustrated in the reaction of pyridine and D-mannitol hexanitrate (LXXXVII). The product of this reaction was... 

D-Mannitol hexanitrate and galactitol hexanitrate are, however, converted readily and exothermically by pyridine, or by ammonium carbonate in aqueous acetone, into 1,2,3,5,6-pentanitrates. In the denitration by pyridine, nitric and nitrous oxides and nitrogen are evolved. Moisture is required in the pyridine in order to provide the proton which replaces the nitronium ion (NOj ). The use of rigorously dried pyridine greatly reduced the yield, but, as the water content was increased, the yield rose to a maximum of 75 %. 

The ability of certain nitrates, especially glycerol trinitrate, to lower the blood pressure has been used clinically in the treatment of hypertension and angina pectoris. A correlation was established between the rate of alkaline hydrolysis and the effectiveness of the nitrate in lowering the blood pressure D-mannitol hexanitrate, hydrolyzed more rapidly than glycerol... 

The charge transfer between D-mannitol hexanitrate and T.VIPD is best presented on Fig. 40 according to T. Urbanski et al. (15). Curs c I shows a CT colourless complex at ca. 1030 tim which disappears after 5 min, and two maxima of Wurster cation (570 and 620 nrn) appear. The intensity of the latter increased in the course of 15 miiuitcs (curve II). 

With a cold mixture of nitric and sulfuric acids, styracitol gives a crystalline, explosive tetranitrate 99). With the same reagent, 1,4 3,6-dianhydro-D-glucitol and 1,4 3,6-dianhydro-D-mannitol give crystalline dinitrates, whereas 1,4-anhydro-D-glucitol and 1,4-anhydro-D-mannitol yield sirupy products. These anhydride nitrates show depressor action, similar to that of glycerol trinitrate and D-mannitol hexanitrate 100). 

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