1,3-Butanediol 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. 

Butylene-1,3-glycol dinitrate (1,3-butanediol dinitrate), also called dinitro-butylene glycol , is an oily liquid (at 15°Q which does not freeze at a temperature of —20°C. Its specific gravity is 1.32. Dinitrobutylene glycol is more volatile than nitroglycerine, but less so than nitroglycol. Collodion cotton dissolves in it fairly easily [4,37]. 

The conversion of 1,3-butanediol to 1,3-butanediol dinitrate is high. 100 kg 1,3-butanediol can be nitrated to produce 187 kg 1,3-butanediol dinitrate with yield of 93.7 %. In the writer s study, 100 kg raw material of 1,3-butanediol was directly nitrated. 2-5 % ammonium nitrate was added in the process. The nitration temperature is 17 °C. The product was successively treated by separation, waterwashing, and stability. 197 kg final product of 1,3-butanediol dinitrate was obtained with a yield of 96.71 %. 

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. 

Butanediol and derivs 2 B368—B370 butanediol dinitrate 2 B369 butanediol dinitrite 2 B369... 

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. 

J. Powling, W.A. Smith The Combustion of 2,3- and 1,4- Butanediol Dinitrates and Some Aldehyde-Nitrogen Dioxide Mixtures, Combust. Flame 2 (1958) 157-170. 

Rate coefficients have been measured for the reaction of OH radicals with a number of organic ketonitrates (R-C0-CH(0N02)-R) and dinitrates (R-CH(0N02)-CH(0N02)-R) using a relative kinetic method. The compounds investigated included 1,2-propane-, 1,2-butane-, and 2,3-butanediol dinitrate, a-nitro-oxy acetone, l-nitro-oxy-2-butanone, 3-nitro-oxy-2-butanone, 3,4-dinitro-oxy-1-butene and cw-l,4-dinitro-oxy-2-butene (LACTOZ 90). The rate coefficients are listed in Chapter 2, Table la. and this study represented the first determination of the OH rate coefficients for these compounds. 

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