Nitroethane is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

having the chemical formula C₂H₅NO₂. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colorless and has a fruity odor.

Preparation

Nitroethane is produced industrially by treating propane with

nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available ni ...

at 350–450 °C. This exothermic reaction produces four industrially significant nitroalkanes: nitromethane, nitroethane,

1-nitropropane 1-Nitropropane (1-NP) is a solvent. It is a colorless liquid, an isomer of 2-nitropropane (2-NP), and classified as a nitro compound. Preparation 1-nitropropane is produced industrially by the reaction of propane and nitric acid. This reaction f ...

, and

2-nitropropane 2-Nitropropane (2-NP) is a solvent. It is a colorless liquid and is classified as a nitro compound. Preparation 2-Nitropropane is produced by the high-temperature vapor-phase nitration of propane, usually with impurities of 1-nitropropane. 2-Ni ...

. The reaction involves free radicals, such as CH₃CH₂CH₂O^., which arise via homolysis of the corresponding nitrite

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

. These alkoxy radicals are susceptible to C—C fragmentation reactions, which explains the formation of a mixture of products.Sheldon B. Markofsky “Nitro Compounds, Aliphatic” in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2002. . Alternatively, nitroethane can be produced by the Victor Meyer reaction of haloethanes such as chloroethane,

bromoethane Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr (which is also used as an abbreviation for ethidium bromide). This volatile compound has an ether-like odor. Prepar ...

, or iodoethane with silver nitrite in

diethyl ether Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable li ...

THF Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is ma ...

. The Kornblum modification of this reaction uses

sodium nitrite Sodium nitrite is an inorganic compound with the chemical formula NaNO2. It is a white to slightly yellowish crystalline powder that is very soluble in water and is hygroscopic. From an industrial perspective, it is the most important nitrite ...

in either a dimethyl sulfoxide or

dimethylformamide Dimethylformamide is an organic compound with the formula ( CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majo ...

solvent.

Uses

Via condensations like the Henry reaction, nitroethane converts to several compounds of commercial interest. Condensation with 3,4-dimethoxybenzaldehyde affords the precursor to the

antihypertensive Antihypertensives are a class of drugs that are used to treat hypertension (high blood pressure). Antihypertensive therapy seeks to prevent the complications of high blood pressure, such as stroke and myocardial infarction. Evidence suggests th ...

drug

methyldopa Methyldopa, sold under the brand name Aldomet among others, is a medication used for high blood pressure. It is one of the preferred treatments for high blood pressure in pregnancy. For other types of high blood pressure including very high bl ...

; condensation with unsubstituted benzaldehyde yields phenyl-2-nitropropene, a precursor for amphetamine drugs. Nitroethane condenses with two equivalents of

formaldehyde Formaldehyde ( , ) ( systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section ...

to give, after

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic ...

, 2-amino-2-methyl-1,3-propanediol, which in turn condenses with oleic acid to give an oxazoline, which protonates to give a cationic surfactant. Like some other nitrated organic compounds, nitroethane is also used as a

fuel additive Petrol additives increase petrol's octane rating or act as corrosion inhibitors or lubricants, thus allowing the use of higher compression ratios for greater efficiency and power. Types of additives include metal deactivators, corrosion inhib ...

and a precursor to Rocket propellants. Nitroethane is a useful solvent for polymers such as polystyrene and is particularly useful for dissolving cyanoacrylate adhesives. In cosmetics applications, it has been used as a component in artificial nail remover and in overhead ceiling sealant sprays. Nitroethane was previously used successfully as a chemical feedstock (precursor ingredient) in laboratories for the synthesis of multitudes of substances and consumer goods. For example, the medicine Pervitin (methamphetamine) was commonly used in the 19th and 20th century, and was especially popular during WWII by troops of both sides for mood elevation, appetite and sleep suppression and increasing focus and alertness). Nitroalkanes were one of many ingredients used in the synthesis of many phenethylamines, including medications such as Pervitin and the racemic compound

Benzedrine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...

(amphetamine), used as an anorectic medicine for obesity.

Toxicity

Nitroethane is suspected to cause genetic damage and be harmful to the

nervous system In biology, the nervous system is the highly complex part of an animal that coordinates its actions and sensory information by transmitting signals to and from different parts of its body. The nervous system detects environmental changes ...

. Typical TLV/TWA is 100 ppm. Typical STEL is 150 ppm. Skin contact causes

dermatitis Dermatitis is inflammation of the skin, typically characterized by itchiness, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become thickened. The area of skin involved c ...

in humans. In animal studies, nitroethane exposure was observed to cause lacrimation, dyspnea, pulmonary rales,

edema Edema, also spelled oedema, and also known as fluid retention, dropsy, hydropsy and swelling, is the build-up of fluid in the body's tissue. Most commonly, the legs or arms are affected. Symptoms may include skin which feels tight, the area ma ...

, liver and kidney injury, and narcosis. Children have been poisoned by accidental ingestion of artificial nail remover. The for rats is reported as 1100 mg/kg.MSDS for nitroethane (revised October 3, 2005), as reported by Fisher Scientific.
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References

External links

WebBook page for C2H5NO2

{{Authority control Nitroalkanes Nitro solvents Fuels Rocket fuels Liquid explosives Drag racing