Post by Anders Hoveland on Feb 7, 2011 16:04:12 GMT -8
In the picture, all three of these compounds have been already been created. The first one is made from nitroethane, the second from nitromethane, and the third from 1,2-dinitroethane.
There exists a nitroalkyl nitrate ester with a lower melting point! -that can be made from nitroethane and formaldehyde. The two are mixed and some NaOH is added, then the mixture is heated and stirred.
........CH2OH
.........l
O2N--C--CH3
.........l
........CH2OH
a compound with the above structure will form, and can then be nitrated. The resulting compound is melt-castable, unlike PETN.
1,2-dinitroethane could be used instead, and after nitration, will result in a very powerful compound with a mp of only 85C. for the structure of this last compound, see
www.analytica-world.com/news/e/88105/
The nitro group does not react in the nitration. CH3NO2, (CH3)CH2NO2, and (CH3)2CHNO2 are all vulnerable to hydrolysis with acids, so the nitro groups can not survive nitric acid, but (CH3)3CNO2 will not react with acids.
The reaction is called a Meyer reaction. Here is an example when nitromethane is heated with sulfuric acid.
CH3NO2 + H2O + H(+) --> HC(=O)OH + NH3OH(+)
formic acid and a hydroxylamine salt are formed. usually if a nitro compound is being nitrated, the hydroxylamine will be oxidized immediately as it is formed.
I am unsure what the condensation between CH2O and actone is.
I actually found a reference for the condensation of nitroethane with CH2O, then nitration:
H.B. Hass, B.M. Vanderbilt, Industrial English Chem. (1940) Volume 32, p34
working on the synthesis preparation for a nitroalkyl-nitrate ester that will be referred to as MCX (melt castable explosive). It is similar to PETN, except more powerful, slightly less sensitive, and with the desirable property of a low melting point, below the boiling point of water.
You will need a container filled with a hose and a lid that can contain gas pressure. You will also need a generator to produce nitrogen dioxide, similarly fitted with a hose. The two hoses should lead into one container that should be sealed to contain gases, but need not be required to withstand any pressure.
First, the acid and isopropanol are refrigerated to 0 degC.
78.6 mL of 98% concentrated sulfuric acid is slowly and cautiously added to 76.4 mL isopropyl alcohol, over several small additions.
After each addition, propylene gas will be produced, and the cap should be immediately placed over the container and the gas fed into
the gas reaction container. After about 10 minutes, the lid can be removed and another addition made. Altogether, about 23.2 L of propylene gas should be produced.
The propylene gas reacts with nitrogen dioxide gas to form 1,2-dinitropropane. Around 130g of this solid should form. It has a melting point between 40-55 degC. This substance is not entirely thermally stable and should be kept cool, and be refrigerated if stored for more than an hour.
The 1,2-dinitropropane is added to 280g of 40% formaldehyde solution, and 0.5g calcium hydroxide is dissolved in 130mL pure alcohol. The mixture is stirred and allowed to stand for one day, then the mixture is slowly heated on an electric hotplate outside, taking care to avoid any spark or flame that could ignite the flammable alcohol vapor. This will leave behind a syrupy liquid, which probably could be optionally dried to a solid using anhydrous magnesium sulfate. A typical nitration, using mixed acids and an ice bath, is then performed on the liquid. This yields
1-methyl-1,2,2,-tri-[nitroxymethylene]-1,2-dinitroethane, with the structure O2NC(CH2ONO2)2C(NO2)(CH2ONO2)CH3. This substance has a melting point below 85 degC, and should be about as powerful as RDX.
Condensing nitroethane with CH2O, then nitration,
would make (O2NOCH2)2C(NO2)CH3
chemical names could be,
bis-nitroxy,tert-nitro isobutane or
2-methyl,2-nitro propane-1,3-nitrate
This compound is a liquid that could potentially find use as an energetic plasticizer.
There exists a nitroalkyl nitrate ester with a lower melting point! -that can be made from nitroethane and formaldehyde. The two are mixed and some NaOH is added, then the mixture is heated and stirred.
........CH2OH
.........l
O2N--C--CH3
.........l
........CH2OH
a compound with the above structure will form, and can then be nitrated. The resulting compound is melt-castable, unlike PETN.
1,2-dinitroethane could be used instead, and after nitration, will result in a very powerful compound with a mp of only 85C. for the structure of this last compound, see
www.analytica-world.com/news/e/88105/
The nitro group does not react in the nitration. CH3NO2, (CH3)CH2NO2, and (CH3)2CHNO2 are all vulnerable to hydrolysis with acids, so the nitro groups can not survive nitric acid, but (CH3)3CNO2 will not react with acids.
The reaction is called a Meyer reaction. Here is an example when nitromethane is heated with sulfuric acid.
CH3NO2 + H2O + H(+) --> HC(=O)OH + NH3OH(+)
formic acid and a hydroxylamine salt are formed. usually if a nitro compound is being nitrated, the hydroxylamine will be oxidized immediately as it is formed.
I am unsure what the condensation between CH2O and actone is.
I actually found a reference for the condensation of nitroethane with CH2O, then nitration:
H.B. Hass, B.M. Vanderbilt, Industrial English Chem. (1940) Volume 32, p34
working on the synthesis preparation for a nitroalkyl-nitrate ester that will be referred to as MCX (melt castable explosive). It is similar to PETN, except more powerful, slightly less sensitive, and with the desirable property of a low melting point, below the boiling point of water.
You will need a container filled with a hose and a lid that can contain gas pressure. You will also need a generator to produce nitrogen dioxide, similarly fitted with a hose. The two hoses should lead into one container that should be sealed to contain gases, but need not be required to withstand any pressure.
First, the acid and isopropanol are refrigerated to 0 degC.
78.6 mL of 98% concentrated sulfuric acid is slowly and cautiously added to 76.4 mL isopropyl alcohol, over several small additions.
After each addition, propylene gas will be produced, and the cap should be immediately placed over the container and the gas fed into
the gas reaction container. After about 10 minutes, the lid can be removed and another addition made. Altogether, about 23.2 L of propylene gas should be produced.
The propylene gas reacts with nitrogen dioxide gas to form 1,2-dinitropropane. Around 130g of this solid should form. It has a melting point between 40-55 degC. This substance is not entirely thermally stable and should be kept cool, and be refrigerated if stored for more than an hour.
The 1,2-dinitropropane is added to 280g of 40% formaldehyde solution, and 0.5g calcium hydroxide is dissolved in 130mL pure alcohol. The mixture is stirred and allowed to stand for one day, then the mixture is slowly heated on an electric hotplate outside, taking care to avoid any spark or flame that could ignite the flammable alcohol vapor. This will leave behind a syrupy liquid, which probably could be optionally dried to a solid using anhydrous magnesium sulfate. A typical nitration, using mixed acids and an ice bath, is then performed on the liquid. This yields
1-methyl-1,2,2,-tri-[nitroxymethylene]-1,2-dinitroethane, with the structure O2NC(CH2ONO2)2C(NO2)(CH2ONO2)CH3. This substance has a melting point below 85 degC, and should be about as powerful as RDX.
Condensing nitroethane with CH2O, then nitration,
would make (O2NOCH2)2C(NO2)CH3
chemical names could be,
bis-nitroxy,tert-nitro isobutane or
2-methyl,2-nitro propane-1,3-nitrate
This compound is a liquid that could potentially find use as an energetic plasticizer.