Nitroethane
Encyclopedia
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.
with nitric acid
at 350–450 °C. This exothermic
reaction produces four industrially significant nitroalkanes: nitromethane
, nitroethane, 1-nitropropane, and 2-nitropropane. The reaction involves free radicals, such as CH3CH2CH2O., which arise via homolysis of the corresponding nitrite ester
. These alkoxy radicals are susceptible to C—C fragmentation reactions, which explains the formation of a mixture of products.
affords the precursor to the antihypertensive
drug methyldopa
; condensation with unsubstituted benzaldehyde yields phenyl-2-nitropropene
. Nitroethane condenses with two equivalents of formaldehyde
to give, after hydrogenation
, 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 and a precursor to explosives.
Nitroethane is a useful solvent for polymers such as polystyrene
and is particularly useful for dissolving cyanoacrylate
adhesives. In niche applications, it has been used as a component in artificial nail
remover and in overhead ceiling sealant sprays.
. Typical TLV/TWA is 100 ppm. Typical STEL is 150 ppm. 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. Children have been poisoned by accidental ingestion of artificial nail remover.
The for rats is reported as 1100 mg/kg.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
having the chemical formula C2H5NO2. Similar in many regards to nitromethane
Nitromethane
Nitromethane is an organic compound with the chemical formula . It is the simplest organic nitro compound. It is a slightly viscous, highly polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a reaction medium, and as a cleaning solvent...
, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colourless and has a fruity odor.
Preparation
Nitroethane is produced industrially by treating propanePropane
Propane is a three-carbon alkane with the molecular formula , normally a gas, but compressible to a transportable liquid. A by-product of natural gas processing and petroleum refining, it is commonly used as a fuel for engines, oxy-gas torches, barbecues, portable stoves, and residential central...
with nitric acid
Nitric acid
Nitric acid , also known as aqua fortis and spirit of nitre, is a highly corrosive and toxic strong acid.Colorless when pure, older samples tend to acquire a yellow cast due to the accumulation of oxides of nitrogen. If the solution contains more than 86% nitric acid, it is referred to as fuming...
at 350–450 °C. This exothermic
Exothermic
In thermodynamics, the term exothermic describes a process or reaction that releases energy from the system, usually in the form of heat, but also in the form of light , electricity , or sound...
reaction produces four industrially significant nitroalkanes: nitromethane
Nitromethane
Nitromethane is an organic compound with the chemical formula . It is the simplest organic nitro compound. It is a slightly viscous, highly polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a reaction medium, and as a cleaning solvent...
, nitroethane, 1-nitropropane, and 2-nitropropane. The reaction involves free radicals, such as CH3CH2CH2O., which arise via homolysis of the corresponding nitrite ester
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
. These alkoxy radicals are susceptible to C—C fragmentation reactions, which explains the formation of a mixture of products.
Uses
Via condensations like the Henry reaction, nitroethane converts to several compounds of commercial interest. Condensation with 3,4-dimethoxybenzaldehydeBenzaldehyde
Benzaldehyde is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful. This colorless liquid has a characteristic pleasant almond-like odor...
affords the precursor to the antihypertensive
Antihypertensive
The antihypertensives are a class of drugs that are used to treat hypertension . Evidence suggests that reduction of the blood pressure by 5 mmHg can decrease the risk of stroke by 34%, of ischaemic heart disease by 21%, and reduce the likelihood of dementia, heart failure, and mortality from...
drug methyldopa
Methyldopa
Methyldopa is an alpha-adrenergic agonist psychoactive drug used as a sympatholytic or antihypertensive. Its use is now mostly deprecated following the introduction of alternative safer classes of agents...
; condensation with unsubstituted benzaldehyde yields phenyl-2-nitropropene
Phenyl-2-nitropropene
Phenyl-2-nitropropene is a chemical compound with the chemical formula is C9H9NO2. It can be produced by the reaction of benzaldehyde and nitroethane in the presence of a basic catalyst. It can be reduced in the presence of a catalyst to produce phenylacetone, which is a controlled precursor of...
. Nitroethane condenses with two equivalents of formaldehyde
Formaldehyde
Formaldehyde is an organic compound with the formula CH2O. It is the simplest aldehyde, hence its systematic name methanal.Formaldehyde is a colorless gas with a characteristic pungent odor. It is an important precursor to many other chemical compounds, especially for polymers...
to give, after hydrogenation
Hydrogenation
Hydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...
, 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
Surfactant
Surfactants are compounds that lower the surface tension of a liquid, the interfacial tension between two liquids, or that between a liquid and a solid...
.
Like some other nitrated organic compounds, nitroethane is also used as a fuel additive and a precursor to explosives.
Nitroethane is a useful solvent for polymers such as polystyrene
Polystyrene
Polystyrene ) also known as Thermocole, abbreviated following ISO Standard PS, is an aromatic polymer made from the monomer styrene, a liquid hydrocarbon that is manufactured from petroleum by the chemical industry...
and is particularly useful for dissolving cyanoacrylate
Cyanoacrylate
Cyanoacrylate is the generic name for cyanoacrylate based fast-acting adhesives such as methyl 2-cyanoacrylate, ethyl-2-cyanoacrylate , and n-butyl cyanoacrylate...
adhesives. In niche applications, it has been used as a component in artificial nail
Manicure
A manicure is a cosmetic beauty treatment for the fingernails and hands performed at home or in a nail salon. A manicure treatment is not only a treatment for the natural nails but also for the hands. A manicure consists of filing, shaping of the free edge, treatments, massage of the hand and the...
remover and in overhead ceiling sealant sprays.
Toxicity
Nitroethane is suspected to cause genetic damage and be harmful to the nervous systemNervous system
The nervous system is an organ system containing a network of specialized cells called neurons that coordinate the actions of an animal and transmit signals between different parts of its body. In most animals the nervous system consists of two parts, central and peripheral. The central nervous...
. Typical TLV/TWA is 100 ppm. Typical STEL is 150 ppm. Skin contact causes dermatitis
Dermatitis
-Etymology:Dermatitis derives from Greek derma "skin" + -itis "inflammation" and genetic disorder.-Terminology:There are several different types of dermatitis. The different kinds usually have in common an allergic reaction to specific allergens. The term may describe eczema, which is also called...
in humans. In animal studies, nitroethane exposure was observed to cause lacrimation, dyspnea
Dyspnea
Dyspnea , shortness of breath , or air hunger, is the subjective symptom of breathlessness.It is a normal symptom of heavy exertion but becomes pathological if it occurs in unexpected situations...
, pulmonary rales, edema
Edema
Edema or oedema ; both words from the Greek , oídēma "swelling"), formerly known as dropsy or hydropsy, is an abnormal accumulation of fluid beneath the skin or in one or more cavities of the body that produces swelling...
, 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.