Nitroethane

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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
144,026 kJ/kmol
Hazards
Safety data sheet Sigma-Aldrich
Flash point 28 °C (82 °F; 301 K)
Lethal dose or concentration (LD, LC):
1,100 mg/kg (rat, oral)
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.

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

  1. Hass; Hodge; Vanderbilt; Industrial and Engineering Chemistry; vol. 28; (1936); p. 341
  2. 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
  3. Kundrat, Ondrej; Eigner, Vaclav; Dvorakova, Hana; Lhotak, Pavel; Organic Letters; vol. 13; nb. 15; (2011); p. 4032 - 4035
  4. Bamberger; Chemische Berichte; vol. 35; (1902); p. 4294; Chemische Berichte; vol. 36; (1903); p. 711

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