Nitroethane

General information

Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colourless, and has a fruity odor. In clandestine synthesis nitroethane is used as precursor for Phenyl-2-nitropropene in Henry reaction.

Physical properties

• CAS Number: 79-24-3;
• Chemical formula: C2H5NO2;
• Molar mass: 75.067 g/mol;
• Density: 1.0448 g/cm3 at 25 °C;
• Melting Point: -89.5 °C;
• Boiling point: 114 — 115 °C (237 °F; 387 K) ;
• Appearance: oily liquid;

Chemical properties

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 nitroaldol reaction (or Henry reaction).

Nitroethane is a colorless liquid, with a fruity odor, slightly soluble in water, but miscible in organic solvents.

Solubility: Miscible with acetone, chloroform, diethyl ether, ethanol, isopropanol, methanol, nitromethane;

UPAC name: Nitroethane;

Other names: 1-Nitroethane; Ethane, nitro-; NSC 8800;

Synthesis ways

Nitroethane can be produced by the Victor Meyer reaction of haloethanes such as chloroethane, bromoethane, or iodoethane with silver nitrite in diethyl ether or THF.

The Kornblum modification of this reaction uses sodium nitrite in either a dimethyl sulfoxide or dimethylformamide solvent.

Also Nitroethane can be obtained from sodium ethyl sulfate and a metal nitrite. These syntheses methods and video tutorials can be learned by links above.

Purification

89 ml Of crude nitroethane was obtained. An equal volume of water is added to this nitroethane and the mixture is distilled with a 25 cm vigreux distilling column at a rate of 1 drop per 2-3 seconds.

The following fractions were obtained:

1. Up to 74 °C - 7 ml (8% by volume) - the fraction was discarded;
2. 74-80 °C - 4.5 ml (5% vol.) - the fraction was retained;
3. 80-88 °C - 58.5 ml (66% vol.) ) - the main fraction (saturated with salt and separated from water, has a light yellow color);
4. 88-95 °C - 3 ml (3% vol.) - the fraction was retained;
5. A cloudy water with orange drops at the bottom, which, it seems, can even crystallize by morning, was remained in the flask 89-7-4.5-58.5-3=16 ml (18% vol.);

In total, from 89 ml of a broth 58.5 ml of the main fraction + 7.5 ml of tops and tails were obtained, which should also contain a lot of nitroethane and can be further distilled.

Magnesium sulfate is added to the main fraction (58.5 ml) for drying. It dries for about 30 minutes, it took so much to disassemble, wash and dry the device. Dried nitroethane is filtered and distilled from a 100 ml flask with the same reflux condenser (and with the addition of 15 ml of vaseline oil) at a rate of 1 drop in 3-5 seconds (the main fraction is 1 drop in 1-2 seconds).

The following fractions were obtained:

1. Up to 65 °C - the nasty pong from condenser;
2. 65-110 °C - 6 ml (10% vol.) - the fraction was thrown away;
3. 110-112 °C - 7.5 ml (13% vol.) - yellow-green color (fraction retained);
4. 112-113.5 °C - 38 ml (65% vol.) - the main fraction, colorless;
5. There were no tails, i.e. if a high-boiling liquid (Vaseline oil) had not been specially added, then it would have been distilled off dry;

The main fraction (38 ml) is a colorless liquid with a pleasant smell reminiscent of ethyl alcohol, distilled in the range of 1.5 degrees. Perhaps it is a very pure nitroethane. From 89 ml of "nitroethane from sodium ethyl sulfate" 38 ml of nitroethane were obtained, 15 ml of other fractions which is possible to obtain an additional ~5 ml of nitroethane. In conclusion, Nitroethane in the raw product is only 40-50%

Legal status

Certain superglue removers (OTC) 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 [1] chemical and individuals cannot purchase this compound. Isn't controlled in European union [2].

Legal application

Nitroethane is most commonly used as a solvent for artificial polymers such as styrene, and particularly for dissolving cyanoacrylate adhesives. It has been used as a component in artificial nail remover and in overhead ceiling sealant sprays, although it is not common in such applications. Nitroethane is also used as a fuel additive for increasing the octane rating of gasoline, as a pure fuel in certain drag racing vehicles, and as a propellant. In addition, nitroethane finds use as a reagent in various chemical syntheses, primarily in the production of pharmaceutical compounds.

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.

Toxicity and rules for handling the substance

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. The LD50 for rats is reported as 1100 mg/kg.

[1] DEA Drug Scheduling.

[2] European Chemicals Agency List – Substances restricted under REACH.