Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, 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 ...
with the
formula
In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
CH
3C(O)CH
2CH
3. This colorless liquid
ketone
In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...
has a sharp, sweet odor reminiscent of
acetone
Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...
. It is produced industrially on a large scale, but occurs in nature only in trace amounts.
[Wilhelm Neier, Guenter Strehlke "2-Butanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002.] It is partially soluble in water, and is commonly used as an industrial solvent.
It is an
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...
of another solvent,
tetrahydrofuran
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 ...
.
Production
Butanone may be produced by oxidation of
2-butanol. The
dehydrogenation of 2-butanol is
catalysed by
copper
Copper is a chemical element; it has symbol Cu (from Latin ) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pinkish-orang ...
,
zinc
Zinc is a chemical element; it has symbol Zn and atomic number 30. It is a slightly brittle metal at room temperature and has a shiny-greyish appearance when oxidation is removed. It is the first element in group 12 (IIB) of the periodic tabl ...
, or
bronze
Bronze is an alloy consisting primarily of copper, commonly with about 12–12.5% tin and often with the addition of other metals (including aluminium, manganese, nickel, or zinc) and sometimes non-metals (such as phosphorus) or metalloid ...
:
:CH
3CH(OH)CH
2CH
3 → CH
3C(O)CH
2CH
3 + H
2
This is used to produce approximately 700 million kilograms yearly. Other syntheses that have been examined but not implemented include
Wacker oxidation of
2-butene and oxidation of
isobutylbenzene, which is analogous to the industrial production of
acetone
Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...
.
[ The ]cumene process
The cumene process (cumene-phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene (isopropyl benzene), the intermediate material during the process. It ...
can be modified to produce phenol and a mixture of acetone and butanone instead of only phenol and acetone in the original.
Both liquid-phase oxidation of heavy naphtha
Naphtha (, recorded as less common or nonstandard in all dictionaries: ) is a flammable liquid hydrocarbon mixture. Generally, it is a fraction of crude oil, but it can also be produced from natural-gas condensates, petroleum distillates, and ...
and the Fischer–Tropsch reaction produce mixed oxygenate streams, from which 2-butanone is extracted by fractionation.
Applications
Solvent
Butanone is an effective and common solvent and is used in processes involving gums, resin
A resin is a solid or highly viscous liquid that can be converted into a polymer. Resins may be biological or synthetic in origin, but are typically harvested from plants. Resins are mixtures of organic compounds, predominantly terpenes. Commo ...
s, cellulose acetate
In biochemistry, cellulose acetate refers to any acetate ester of cellulose, usually cellulose diacetate. It was first prepared in 1865. A bioplastic, cellulose acetate is used as a film base in photography, as a component in some coatings, and ...
and nitrocellulose
Nitrocellulose (also known as cellulose nitrate, flash paper, flash cotton, guncotton, pyroxylin and flash string, depending on form) is a highly flammable compound formed by nitrating cellulose through exposure to a mixture of nitric acid and ...
coatings and in vinyl films. For this reason it finds use in the manufacture of plastics, textiles, in the production of paraffin wax
Paraffin wax (or petroleum wax) is a soft colorless solid derived from petroleum, coal, or oil shale that consists of a mixture of hydrocarbon molecules containing between 20 and 40 carbon atoms. It is solid at room temperature and melting poi ...
, and in household products such as lacquer
Lacquer is a type of hard and usually shiny coating or finish applied to materials such as wood or metal. It is most often made from resin extracted from trees and waxes and has been in use since antiquity.
Asian lacquerware, which may be c ...
, varnish
Varnish is a clear Transparency (optics), transparent hard protective coating or film. It is not to be confused with wood stain. It usually has a yellowish shade due to the manufacturing process and materials used, but it may also be pigmente ...
es, paint remover, a denaturing agent for denatured alcohol
Denatured alcohol, also known as methylated spirits, metho, or meths in Australia, Ireland, New Zealand, South Africa, and the United Kingdom, and as Rectified spirit, denatured rectified spirit, is ethanol that has additives to make it poisonou ...
, glues, and as a cleaning agent. It is a prime component of plumbers' priming fluid, used to clean PVC materials. It has similar solvent properties to acetone
Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...
but boils at a higher temperature and has a significantly slower evaporation rate. Unlike acetone, it forms an azeotrope
An azeotrope () or a constant heating point mixture is a mixture of two or more liquids whose proportions cannot be changed by simple distillation.Moore, Walter J. ''Physical Chemistry'', 3rd e Prentice-Hall 1962, pp. 140–142 This happens beca ...
with water,[''Lange's Handbook of Chemistry'', 10th ed. pp1496-1505][''CRC Handbook of Chemistry and Physics'', 44th ed. pp 2143-2184] making it useful for azeotropic distillation of moisture in certain applications. Butanone is also used in dry erase markers as the solvent of the erasable dye.
The hydroxylamine derivative of butanone is methylethyl ketone oxime
Methylethyl ketone oxime is the organic compound with the formula C2H5C(NOH)CH3. This colourless liquid is the oxime derivative of methyl ethyl ketone. MEKO, as it is called in the paint industry, is used to suppress "skinning" of paints: the for ...
(MEKO), which also find use in paints and varnishes as an anti-skinning agent.
Plastic welding
As butanone dissolves 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 many other plastics, it is sold as "model cement" for use in connecting parts of scale model
A scale model is a physical model that is geometrically similar to an object (known as the ''prototype''). Scale models are generally smaller than large prototypes such as vehicles, buildings, or people; but may be larger than small protot ...
kits. Though often considered an adhesive
Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation.
The use of adhesives offers certain advantage ...
, it is functioning as a welding
Welding is a fabrication (metal), fabrication process that joins materials, usually metals or thermoplastics, primarily by using high temperature to melting, melt the parts together and allow them to cool, causing Fusion welding, fusion. Co ...
agent in this context.
Other uses
Butanone is the precursor to methyl ethyl ketone peroxide, which is a catalyst for some polymerization
In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many fo ...
reactions such as crosslinking of unsaturated polyester resins. Dimethylglyoxime can be prepared from butanone first by reaction with ethyl nitrite to give diacetyl monoxime followed by conversion to the dioxime:
:
In the peroxide process
The peroxide process is a method for the industrial production of hydrazine.
In this process hydrogen peroxide is used as an oxidant instead of sodium hypochlorite, which is traditionally used to generate hydrazine. The main advantage of the pero ...
on producing hydrazine
Hydrazine is an inorganic compound with the chemical formula . It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly hazardous unless handled in solution as, for example, hydraz ...
, the starting chemical ammonia is bonded to butanone, oxidized by hydrogen peroxide, bonded to another ammonia molecule.
:
In the final step of the process, hydrolysis produces the desired product, hydrazine, and regenerates the butanone.
:Me(Et)C=NN=C(Et)Me + 2 H2O → 2 Me(Et)C=O + N2H4
Safety
Flammability
Butanone can react with most oxidizing materials and can produce fires. It is moderately explosive, requiring only a small flame or spark to cause a vigorous reaction. The vapor is heavier than air, so it can accumulate at low points. It is explosive at concentrations between 1.4 and 11.4%.[ Concentrations in the air high enough to be flammable are intolerable to humans due to the irritating nature of the vapor.] Butanone fires should be extinguished with carbon dioxide
Carbon dioxide is a chemical compound with the chemical formula . It is made up of molecules that each have one carbon atom covalent bond, covalently double bonded to two oxygen atoms. It is found in a gas state at room temperature and at norma ...
, dry agents, or alcohol-resistant foam.
The ignition of butanone vapor was the proximate cause
In law and insurance, a proximate cause is an event sufficiently related to an injury that the courts deem the event to be the cause of that injury. There are two types of causation in the law: cause-in-fact, and proximate (or legal) cause. Ca ...
of the 2007 Xcel Energy Cabin Creek fire, resulting in the deaths of five workers in a hydroelectric penstock. After the incident, the U.S. Chemical Safety and Hazard Investigation Board specifically noted the danger posed by butanone in confined spaces, and suggested 1,1,1-trichloroethane
1,1,1-Trichloroethane, also known as methyl chloroform and chlorothene, is a chloroalkane with the chemical formula CH3CCl3. It is an isomer of 1,1,2-trichloroethane. A colourless and sweet-smelling liquid, it was once produced industrially i ...
or limonene
Limonene () is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the essential oil of citrus fruit peels. The (+)-isomer, occurring more commonly in nature as the fragrance of oranges, ...
as safer alternatives.
Health effects
Butanone is a constituent of tobacco smoke. It is an irritant, causing irritation to the eyes and nose of humans. Serious animal health effects have been seen only at very high levels. There are no long-term studies with animals breathing or drinking it, and no studies for carcinogenicity in animals breathing or drinking it.
There is some evidence that butanone can potentiate the toxicity of other solvents, in contrast to the calculation of mixed solvent exposures by simply adding exposures.
, the United States Environmental Protection Agency (EPA) listed butanone as a toxic chemical. There are reports of neuropsychological effects. It is rapidly absorbed through undamaged skin and lungs. It contributes to the formation of ground-level ozone
Ground-level ozone (), also known as surface-level ozone and tropospheric ozone, is a trace gas in the troposphere (the lowest level of the atmosphere of Earth, Earth's atmosphere), with an average concentration of 20–30 parts per billion by vo ...
, which is toxic in low concentrations.
Regulation
Butanone is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.
Emission of butanone was regulated in the US as a hazardous air pollutant, because it is a volatile organic compound
Volatile organic compounds (VOCs) are organic compounds that have a high vapor pressure at room temperature. They are common and exist in a variety of settings and products, not limited to Indoor mold, house mold, Upholstery, upholstered furnitur ...
contributing to the formation of tropospheric (ground-level) ozone
Ozone () (or trioxygen) is an Inorganic compound, inorganic molecule with the chemical formula . It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope , break ...
. In 2005, the US Environmental Protection Agency
The Environmental Protection Agency (EPA) is an independent agency of the United States government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it began operation on De ...
removed butanone from the list of hazardous air pollutants (HAPs).
See also
* Butyraldehyde
Butyraldehyde, also known as butanal, is an organic compound with the formula CH3(CH2)2CHO. This compound is the aldehyde derivative of butane. It is a colorless flammable liquid with an unpleasant smell. It is miscible with most organic solvents. ...
* Butane
Butane () is an alkane with the formula C4H10. Butane exists as two isomers, ''n''-butane with connectivity and iso-butane with the formula . Both isomers are highly flammable, colorless, easily liquefied gases that quickly vaporize at ro ...
* ''n''-Butanol
* 2-Butanol
Notes
References
External links
International Chemical Safety Card 0179
* ttps://www.cdc.gov/niosh/npg/npgd0069.html NIOSH Pocket Guide to Chemical Hazardsbr>US EPA Datasheet
*
{{Authority control
Alkanones
Ketone solvents
Pollutants
Commodity chemicals
Sweet-smelling chemicals