Nitroethane is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

having the chemical formula C₂H₅NO₂. Similar in many regards to

nitromethane Nitromethane, sometimes shortened to simply "nitro", is an organic compound with the chemical formula . It is the simplest organic nitro compound. It is a polar liquid commonly used as a solvent in a variety of industrial applications such as in ...

, 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 Propane () is a three-carbon chain alkane with the molecular formula . It is a gas at standard temperature and pressure, but becomes liquid when compressed for transportation and storage. A by-product of natural gas processing and petroleum ref ...

with

nitric acid Nitric acid is an inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into nitrogen oxide, oxides of nitrogen. Most com ...

at 350–450 °C. This

exothermic In thermodynamics, an exothermic process () is a thermodynamic process or reaction that releases energy from the system to its surroundings, usually in the form of heat, but also in a form of light (e.g. a spark, flame, or flash), electricity (e ...

reaction produces four industrially significant nitroalkanes:

, nitroethane, 1-nitropropane, and

2-nitropropane 2-Nitropropane (2-NP) is an organic compound with the formula . It is used as 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 pro ...

. 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 acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

. 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 Viktor Meyer (8 September 18488 August 1897) was a German chemist and significant contributor to both organic chemistry, organic and inorganic chemistry. He is best known for inventing an apparatus for determining vapour densities, the Viktor Meye ...

reaction of haloethanes such as

chloroethane Chloroethane, commonly known as ethyl chloride, is a chemical compound with chemical formula CH3CH2Cl, once widely used in producing tetraethyllead, a gasoline additive. It is a colorless, flammable gas or refrigerated liquid with a faintly sweet ...

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. Prepara ...

, or

iodoethane Ethyl iodide (also iodoethane) is a colorless flammable chemical compound. It has the chemical formula C2H5I and is prepared by heating ethanol with iodine and phosphorus.''Merck Index of Chemicals and Drugs'', 9th ed., monograph 3753 On contact ...

with silver nitrite in

diethyl ether Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...

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 . 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 sa ...

in either a

dimethyl sulfoxide Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula . This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is ...

dimethylformamide Dimethylformamide, DMF is an organic compound with the chemical formula . Its structure is . Commonly abbreviated as DMF (although this initialism is sometimes used for 2,5-dimethylfuran, dimethylfuran, or dimethyl fumarate), this colourless liqui ...

solvent.

Uses

Via condensations like the

Henry reaction The Henry reaction is a classic carbon–carbon bond formation reaction in organic chemistry. Discovered in 1895 by the Belgian chemist Louis Henry (1834–1913), it is the combination of a nitroalkane and an aldehyde or ketone in the presence ...

, nitroethane converts to several compounds of commercial interest. Condensation with

3,4-dimethoxybenzaldehyde Veratraldehyde (3,4-dimethoxybenzaldehyde) is an organic compound with the formula . Several isomers are known. The compound is widely used as a flavorant and odorant. The compound is structurally related to benzaldehyde, with two methoxy groups ...

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, heart failure, kidney failure and myocardial infa ...

drug

methyldopa Methyldopa, also known as α-methyl-L-DOPA and 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 blo ...

; condensation with unsubstituted benzaldehyde yields

phenyl-2-nitropropene 1-Phenyl-2-nitropropene, or simply phenyl-2-nitropropene, or P2NP, as it is commonly referred to, is a chemical compound from the Aromatic compound, aromatic group of compounds, with the formula C9H9NO2. It is a light-yellow crystalline solid with ...

, a precursor for amphetamine drugs. Nitroethane condenses with two equivalents of

formaldehyde Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...

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 redox, reduce or Saturated ...

, 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 Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...

. Like some other nitrated organic compounds, nitroethane is also used as a

fuel additive Gasoline additives may increase gasoline's octane rating, thus allowing the use of higher compression ratios for greater efficiency and power, or act as corrosion inhibitors or lubricants. Other additives include metal deactivators, oxygenates an ...

and Nitroethane is a useful solvent for polymers such as

polystyrene Polystyrene (PS) is a synthetic polymer made from monomers of the aromatic hydrocarbon styrene. Polystyrene can be solid or foamed. General-purpose polystyrene is clear, hard, and brittle. It is an inexpensive resin per unit weight. It i ...

and is particularly useful for dissolving

cyanoacrylate Cyanoacrylates are a family of strong fast-acting adhesives with industrial, medical, and household uses. They are derived from ethyl cyanoacrylate and related esters. The cyanoacrylate group in the monomer rapidly polymerizes in the presence ...

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 (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug use, recreational or Performance-enhancing substance, performance-enhancing drug and less commonly as a secon ...

(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

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

s, including medications such as Pervitin and the

racemic In chemistry, a racemic mixture or racemate () is a mixture that has equal amounts (50:50) of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as r ...

compound

Benzedrine Amphetamine (contracted from alpha- methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity; it is also used to treat binge e ...

(amphetamine), used as an

anorectic An anorectic is a drug that reduces appetite, resulting in lower food consumption, leading to weight loss. These substances work by affecting the central nervous system or certain neurotransmitters to create a feeling of fullness or reduce the desi ...

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 complex system, highly complex part of an animal that coordinates its behavior, actions and sense, sensory information by transmitting action potential, signals to and from different parts of its body. Th ...

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

dermatitis Dermatitis is a term used for different types of skin inflammation, 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 ...

in humans. In animal studies, nitroethane exposure was observed to cause

lacrimation Tears are a clear liquid secreted by the lacrimal glands (tear gland) found in the eyes of all land mammals. Tears are made up of water, electrolytes, proteins, lipids, and mucins that form layers on the surface of eyes. The different types of ...

dyspnea Shortness of breath (SOB), known as dyspnea (in AmE) or dyspnoea (in BrE), is an uncomfortable feeling of not being able to breathe well enough. The American Thoracic Society defines it as "a subjective experience of breathing discomfort that ...

, pulmonary rales,

edema Edema (American English), also spelled oedema (British English), and also known as fluid retention, swelling, dropsy and hydropsy, is the build-up of fluid in the body's tissue (biology), tissue. Most commonly, the legs or arms are affected. S ...

, 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