nitroalkanes are more acidic than corresponding hydrocarbons

(Hexamine reacts with a concentrated HCl solution in a slightly different disproportionation reaction. It is not as hazardous to handle as tetranitromethane because of its low volatility. Always keep the solution out of direct sunlight. beginning with glyoxime O=CHCH=O, the di-nitrolate of this was made, first by condensation with NH2OH, then reaction with NO2 and KNO2. It should be used soon after it is made, or be kept cold. heating is discontinued when the distillation flow slackens considerably, and the crude nitroethane is washed with an equal amount of water, dried over CaCl2, The nitroethane is then re-distilled, collecting the fraction between 114-116°C. The proportion of the nitrocompound was very small. When all the nitroethane dissolved, the solution was cooled to 5°-7° in an ice-water bath.The sodium salt of nitroethane was prepared as above. The crude product was distilled to give 4.2 g (52% yield) of 1,1-dinitroethane, b.p. 75.1g Nitroethane, 0.3g calcium hydroxide and 80g 40% formaldehyde solution was dissolved in 75ml ethanol with stirring and was allowed to stand for 48h at room temperature. 4. 1,1,1-trinitro ethaneAn idea for making 1,1,1-trinitro ethane.NO2 is known to react with an oxime (R2C=NOH) to make R2C(NO)(NO2). Patent 4910322 32.5 grams of ethyl bromide (0.3 moles) was poured into a stirred solution of 600ml dimethylformamide and 36 grams dry NaNO2 (0.52 mole) in a beaker standing in a water bath keeping the solution at room temperature as the reaction is slightly exothermic. Trinitromethane is somewhat poisonous: 800 mg/m3/2 hour Inhalation Mouse LC50,compare this with 1230ppm (for 36min, LC50) for tetranitromethane.It can be seen that tetranitromethane is far more toxic (it is highly recommended that the synthesis of this compound never be attempted), but nitroform should still be assumed to give off toxic vapor, and so should be handled outdoors or behind a windowed fumehood.Trinitromethane oxidizes ferrous ions (Fe+2) to ferric (Fe+3). Perhaps using dinitromethane instead of dinitroethane would form the desired 1,3,3-trinitropropane.7.3g CH2=CHNO2 was dripped over 30min into 48g of CH3CH(NO2)2 in 35mL methanol. To a stirred solution of 2.66 g (66.5 mmoles) of sodium hydroxide in 15 ml of water at 20° was added 5.0 g (66.5 mmoles) of nitroethane. 2,2-dinitro propane has a melting point of 51.5degC, and is thermally unstable when warmed. This is because acetone is a ketone and there is a double bond between carbons in equilibrium. Acetone does indeed react with nitrogen dioxideNitrogen dioxide on an alkene will form the nitroalkene. Finally, 16.0 g of solid sodium persulfate (67 mmoles) was added all at once. The one with EtNO2 is somewhat more powerful, but it also requires a higher ratio of HC(NO2)3, so if nitromethane is easily available in large quantities it may be preferable. The flask is cooled and the product decanted from the solids. I do not know which particular reaction in the synthesis is in doubt. The α-carbon of nitroalkanes is somewhat acidic. (1963)Hexanitroethane. One unique feature of nitroalkanes is their high degree of acidity (1). The double bond makes one of the hydrogen atoms come off easier. Mixtures with divinyl ketone can explode at 4°C. As the gaseous nitrite remains only momentarily in contact with the heated asbestos, the yield of the nitro-compound is small, the greater portion of the nitrite escaping conversion. Bubble in nitrogen dioxide into a solution of this salt, and trinitromethane can be obtained, because the intermediate aci- form of nitromethane, which is vulnerable to oxidation, is formed. A third way to prepare nitroethane is from ethyl nitrite. 1,1,1,3-tetranitropropane is an energetic compound with slight plasticity and a melting point around 50 degC. The formed K2C2(NO2)4, which is the same thing as the potassium salt of 1,1,2,2-tetranitro ethane (if this is acidified it leaves free tetranitroethane which is oil-soluble). It was found that when surcharged with moisture the nitrite dissociated more rapidly, yielding larger quantities of alcohols, aldehydes and acids without any appreciable increase in the yield of the nitro-compound. This reaction is somewhat slow, unless the pH is lowered, but in this case that would ruin the reaction. However, the toxicity between the two compounds is otherwise similar for a given concentration in air. Hexanitroethane has a vapor pressure of 0.8 millibar at 30C. Distillation at 100-105°C/13 mmHg (85-86°C/6 mmHg, 99°C/10 mmHg) gave 48g 2-nitropropanol (46%) and 14.3g of 2-nitro-2-methyl- 1,3-propanediol, the latter remained as a crystalline residue in the distillation flask after distillation of the 2-nitropropanol. The remaining organic phase was dried over magnesium sulfate, filtered, and the petroleum ether was removed by distillation under reduced pressure on a water bath, which temperature was allowed to slowly rise to about 65°C. The mixture is then heated to 125-130°C, at which temperature the nitroethane distills over as formed. It is commonly known that gem-dinitro compounds are easily derived from oximes. many of the reactions used are rather esoteric and not commonly known of. Diluted with water again, then saturated with NaCl, (presumably to salt out the trinitopropane). natrium nitrit, sulfurik acid och isopropanol, reaktionen kanna också bli gjort med HCl och etanol. The petroleum ether layer was poured off and saved, and the aqueous phase was extracted four more times with 100 ml of petroleum ether each, whereafter the organic extracts were pooled, and in turn was washed with 4x75ml of water. You would be well advised to avoid ever preparing tetranitromethane, which was once considered for use as a chemical weapon.

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