Nitroethane
| Names | |
|---|---|
| IUPAC name
Nitroethane
| |
| Other names
1-Nitroethane
| |
| Properties | |
| C2H5NO2 | |
| Molar mass | 75.07 g/mol |
| Appearance | Colorless liquid |
| Odor | Mildy, fruity |
| Density | 1.054 g/cm3 |
| Melting point | −90 °C (−130 °F; 183 K) |
| Boiling point | 114–115 °C (237–239 °F; 387–388 K) |
| 4.6 g/100 ml (20 °C) | |
| Solubility | Miscible with acetone, chloroform, diethyl ether, ethanol, isopropanol, methanol, nitromethane |
| Vapor pressure | 21 mmHg (25 °C) |
| Acidity (pKa) | 16.7 |
| Thermochemistry | |
| Std enthalpy of
formation (ΔfH |
144,026 kJ/kmol |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 28 °C (82 °F; 301 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
1,100 mg/kg (rat, oral) |
| LC50 (Median concentration)
|
5,000 ppm (rabbit, 2 hr) |
| Related compounds | |
| Related compounds
|
Nitromethane Nitropropane |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Nitroethane is an organic compound having the chemical formula C2H5NO2.
Contents
Properties
Chemical
Nitroethane reacts with an aldehyde or ketone in the presence of a base to form β-nitro alcohols, which can be further dehydrated to yield nitroalkenes, nitroketones or β-amino alcohols, process known as Henry reaction (or Nitroaldol reaction).
Physical
Nitroethane is a colorless liquid, with a fruity odor, slightly soluble in water, but miscible in organic solvents.
Availability
Certain superglue removers contain nitroethane, though the amount is small.
Nitroethane is sold by chemical suppliers, however, since it's a drug precursor, it's extremely difficult for the amateur chemist to acquire this compound. In US nitroethane is a DEA List I chemical and individuals cannot purchase this compound.
Preparation
Nitroethane is produced industrially by treating propane with nitric acid at 350–450 °C. The reaction produces 4 main products: 1-nitropropane (25%), 2-nitropropane (40%), nitroethane (10%) and nitromethane (25%).
- C3H8 + HNO3 → CH3CH2CH2NO2 + CH3CH(NO2)CH3 + CH3CH2NO2 + CH3NO2
Nitroethane is separated from the mixture via fractional distillation.
Dinitrogen tetroxide can also be used instead of nitric acid, though the temperature required for the reaction to work is higher than the previous, between 790 - 795 °C.[1]
More accessible, nitroethane can be produced by the reaction between haloethanes like ethyl chloride, ethyl bromide, or ethyl iodide with silver nitrite in diethyl ether or THF.
- CH3-CH2-X + AgNO2 → CH3-CH2-NO2 + AgX
If silver nitrite is unavailable, sodium nitrite can be used, and instead of diethyl ether, dimethyl sulfoxide or dimethylformamide are used as solvents instead.[2] One paper claims that acetone can also be used as solvent, with sonication. No yields are given.[3]
Reaction of sodium or potassium ethyl sulfate with a nitrite salt will also give ethyl nitrite. A more dangerous route uses diethyl sulfate.
Oxidation of ethylamine with peroxymonosulfuric acid will give nitroethane.[4] DMDO can also be used to oxidize amines to nitro compounds.
Projects
- Make various compounds via the Henry reaction
- Dissolve superglue
- Fuel additive
- Make various energetic materials
Handling
Safety
Nitroethane is suspected to cause genetic damage and be harmful to the nervous system. Skin contact causes dermatitis in humans. In animal studies, nitroethane exposure was observed to cause lacrimation, dyspnea, pulmonary rales, edema, liver and kidney injury, and narcosis.
Storage
Nitroethane should be kept in glass bottles, in a special cupboard, away from ammonia, amines and other bases.
Disposal
Nitromethane should be mixed with another solvent, like ethanol and burned. Do this outside.
References
- ↑ Hass; Hodge; Vanderbilt; Industrial and Engineering Chemistry; vol. 28; (1936); p. 341
- ↑ Shao, Yi-Ming; Yang, Wen-Bin; Kuo, Tun-Hsun; Tsai, Keng-Chang; Lin, Chun-Hung; Yang, An-Suei; Liang, Po-Huang; Wong, Chi-Huey; Bioorganic and Medicinal Chemistry; vol. 16; nb. 8; (2008); p. 4652 - 466
- ↑ Kundrat, Ondrej; Eigner, Vaclav; Dvorakova, Hana; Lhotak, Pavel; Organic Letters; vol. 13; nb. 15; (2011); p. 4032 - 4035
- ↑ Bamberger; Chemische Berichte; vol. 35; (1902); p. 4294; Chemische Berichte; vol. 36; (1903); p. 711
