1.3- Propanediol dinitrate—

Propanediol (1,2-Propylene glycol, 1,2-Dihydroxy propane, Methyl glycol). CH3.CHOH.CH2OH mw 76.09 colorl, viscous, stable, hygr liq bp 187.3°, d 1.0381g/cc at 20/20° RI 1.4293 at 27° fl pt (open cup) 210°F autoignition temp 780°F. Misc with w, ales, and many org solvents in all proportions. Can be prepd by hydration of propylene oxide. On nitration it yields the exp] 1,2-Propanediol Dinitrate (see below)... 

As early as 1904, 1,2-Propanediol Dinitrate was proposed (Ref 3) as an additive to lower the freezing temp of NG, but its practical application on a large scale was hindered by lack of the raw material, propane-1,2-diol. It is only recently that the synthesis of glycol from ethylene led to the development of a method for producing methyl glycol from propylene via cnioro-hydrin. Even so, propylene-1,2-glycol is somewhat more expensive than glycols derived from ethylene (Ref 9)... 

Note A mixt consisting chiefly of 1,2-Propanediol Dinitrate, but contg varying amts of ethylene glycol dinitrate and butylene glycol dinitrate was marketed under the trade name Nitro-byronel (Ref 8)... 

In many cases almost quantitative yields are reported for the formation of v/c-dinitrate esters from the reaction of simple alkyl and dialkyl epoxides with dinitrogen pentoxide (Table 3.2). Some of the products formed include ethylene glycol dinitrate (2) (96%), 1,2-propanediol dinitrate (8) (96 %), 2,3-butanediol dinitrate (94 %) and 1,2-butanediol dinitrate (96 %). Reaction times are of the order of 5-15 minutes. 

Canfield and Rohrback ° reported on the reaction of some electron-deficient difluo-roaminoalkenes with dinitrogen pentoxide in chloroform at subambient temperatures. Contrary to previous work that the /3-nitro-nitrate ester should be the main product, the corresponding vtc-dinitrate esters were isolated from these reactions l,4-bis(iV,iV-difiuoroamino)-2,3-butanediol dinitrate (55), 3,4-bis(iV,iV-difluoroamino)-l,2-butanediol dinitrate (56) and 3-(iV,iV-difluoroamino)-1,2-propanediol dinitrate (57) were isolated in 30 %, 27 %, and 55 % yields respectively, from the parent alkenes. 

Propyleneimine is reported to react with a solution of absolute nitric acid in methylene chloride to yield 1,2-propanediol dinitrate, presumably via the intermediate primary... 

As shown, NO3 radical leads to different chemistry than does HO radical the peroxy radical can decompose to yield several products, including acetaldehyde, formaldehyde, 1,2-propanediol dinitrate (PDDN), nitroxyperoxypropyl nitrate (NPPN), and a-nitrooxyacetone. The reactions of the peroxy radicals with NO , species can lead to highly functionalized (and oxidized) organic compounds. 

Trinitrophenyi-nitromino). 1,2-dinitroxy-propone or 3-(2, 4, 6 -Trinitro-phenylnitramino)- 1.2-propanediol Dinitrate. 

According to de Kreuk the difference between the viscosity values of similar compounds (e.g. 1,3- and 1,2-propanediol dinitrates, 1,3- and 2,3-butanediol dinitrates) may be attributed to rotational isomerism. Free rotation makes possible the formation of trans isomers which according to this author should possess a higher viscosity. This would explain the relatively high viscosities of 1,3-propanediol and 1,3-butanediol dinitrates. 

The difference between the dipole moments of the pure substance and their value in benzene solution is (according to de Kreuk) due to the possible formation of a certain amount of trans rotation isomer in benzene. High values for pure 1,2-propanediol dinitrate and 2,3-butanediol dinitrate are due to the presence of a high proportion of the cis form in the pure liquids. 

Methyl glycol dinitrate (propylene-1,2-glycol dinitrate or 1,2-propanediol dinitrate) is an oily liquid, boiling at 92°C at 10 mm Hg. Its spedfic gravity is 1.368 (at 20°Q. The liquid does not freeze at a temperature of —20°C. It is more volatile thfcn the isomeric propylene-1,3-glycol dinitrate. 

F autoignition temp 780°F. Misc with w, ales, and many org solvents in aU proportions. Can be prepd by hydration of propylene oxide. On nitration it yields the expl 1,2-Propanediol Dinitrate (see below)... 

C3H4CI20 trans-1,3-dichloropropene oxide 66826-73-1 391.30 33.546 2 1675 C3H5CIN206 3-chloro-1,2-propanediol dinitrate 2612-33-1 465.65 40.594 1,2... 

Propylene glycol dinitrate is the explosive part of Otto Fuel II. It is a colorless liquid with an unpleasant odor. Other names for propylene glycol dinitrate are PGDN, 1,2-propylene glycol dinitrate, and 1,2-propanediol dinitrate. 

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