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Butanone

Butanone

Overview
Butanone, also known as methyl ethyl ketone or MEK, is an organic compound
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...

 with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 CH3C(O)CH2CH3. This colorless liquid ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...

 has a sharp, sweet odor reminiscent of butterscotch
Butterscotch
Butterscotch is a type of confectionery whose primary ingredients are brown sugar and butter, although other ingredients such as corn syrup, cream, vanilla, and salt are part of some recipes...

 and acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...

. It is produced industrially on a large scale, and also occurs in trace amounts in nature. It is soluble in water and is commonly used as an industrial solvent.

Oxidation of 2-butanol
2-Butanol
2-Butanol, or sec-butanol, is an organic compound with formula CH3CHCH2CH3. This secondary alcohol is a flammable, colorless liquid that is soluble in 12 parts water and completely miscible with polar organic solvents such as ethers and other alcohols. It is produced on a large scale, primarily as...

 is one way to produce butanone.
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Encyclopedia
Butanone, also known as methyl ethyl ketone or MEK, is an organic compound
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...

 with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 CH3C(O)CH2CH3. This colorless liquid ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...

 has a sharp, sweet odor reminiscent of butterscotch
Butterscotch
Butterscotch is a type of confectionery whose primary ingredients are brown sugar and butter, although other ingredients such as corn syrup, cream, vanilla, and salt are part of some recipes...

 and acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...

. It is produced industrially on a large scale, and also occurs in trace amounts in nature. It is soluble in water and is commonly used as an industrial solvent.

Production


Oxidation of 2-butanol
2-Butanol
2-Butanol, or sec-butanol, is an organic compound with formula CH3CHCH2CH3. This secondary alcohol is a flammable, colorless liquid that is soluble in 12 parts water and completely miscible with polar organic solvents such as ethers and other alcohols. It is produced on a large scale, primarily as...

 is one way to produce butanone. Butanone is produced by the dehydrogenation
Dehydrogenation
Dehydrogenation is a chemical reaction that involves the elimination of hydrogen . It is the reverse process of hydrogenation. Dehydrogenation reactions may be either large scale industrial processes or smaller scale laboratory procedures....

 of 2-butanol using a catalyst based on copper
Copper
Copper is a chemical element with the symbol Cu and atomic number 29. It is a ductile metal with very high thermal and electrical conductivity. Pure copper is soft and malleable; an exposed surface has a reddish-orange tarnish...

, zinc
Zinc
Zinc , or spelter , is a metallic chemical element; it has the symbol Zn and atomic number 30. It is the first element in group 12 of the periodic table. Zinc is, in some respects, chemically similar to magnesium, because its ion is of similar size and its only common oxidation state is +2...

, or bronze
Bronze
Bronze is a metal alloy consisting primarily of copper, usually with tin as the main additive. It is hard and brittle, and it was particularly significant in antiquity, so much so that the Bronze Age was named after the metal...

:
CH3CH(OH)CH2CH3 → CH3C(O)CH2CH3 + H2

In this way, approximately 700M kg are produced yearly. Other routes that have been examined but not implemented include Wacker oxidation of 2-butene
2-Butene
2-Butene is an acyclic alkene with four carbon atoms. It is the simplest alkene exhibiting cis/trans-isomerism ; that is, it exists as two geometrical isomers cis-2-butene , shown at the right, and trans-2-butene , not shown.It is a petrochemical, produced by the catalytic cracking of crude oil...

 and oxidation of isobutylbenzene (analogous to the industrial route to acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...

).

Both liquid-phase oxidation of heavy naphtha
Naphtha
Naphtha normally refers to a number of different flammable liquid mixtures of hydrocarbons, i.e., a component of natural gas condensate or a distillation product from petroleum, coal tar or peat boiling in a certain range and containing certain hydrocarbons. It is a broad term covering among the...

 and the Fischer-Tropsch reaction produce mixed oxygenate streams, from which 2-butanone is extracted by fractionation.

Butanone is biosynthesized
Biosynthesis
Biosynthesis is an enzyme-catalyzed process in cells of living organisms by which substrates are converted to more complex products. The biosynthesis process often consists of several enzymatic steps in which the product of one step is used as substrate in the following step...

 by some trees and found in some fruits and vegetables in small amounts. It is released to the air from car
Automobile
An automobile, autocar, motor car or car is a wheeled motor vehicle used for transporting passengers, which also carries its own engine or motor...

 and truck
Truck
A truck or lorry is a motor vehicle designed to transport cargo. Trucks vary greatly in size, power, and configuration, with the smallest being mechanically similar to an automobile...

 exhausts
Exhaust gas
Exhaust gas or flue gas is emitted as a result of the combustion of fuels such as natural gas, gasoline/petrol, diesel fuel, fuel oil or coal. According to the type of engine, it is discharged into the atmosphere through an exhaust pipe, flue gas stack or propelling nozzle.It often disperses...

.

As a solvent


Butanone is an effective and common solvent and is used in processes involving gum
Natural gum
Natural gums are polysaccharides of natural origin, capable of causing a large viscosity increase in solution, even at small concentrations. In the food industry they are used as thickening agents, gelling agents, emulsifying agents, and stabilizers...

s, resin
Resin
Resin in the most specific use of the term is a hydrocarbon secretion of many plants, particularly coniferous trees. Resins are valued for their chemical properties and associated uses, such as the production of varnishes, adhesives, and food glazing agents; as an important source of raw materials...

s, cellulose acetate
Cellulose acetate
Cellulose acetate , first prepared in 1865, is the acetate ester of cellulose. Cellulose acetate is used as a film base in photography, as a component in some adhesives, and as a frame material for eyeglasses; it is also used as a synthetic fiber and in the manufacture of cigarette filters and...

 and nitrocellulose
Nitrocellulose
Nitrocellulose is a highly flammable compound formed by nitrating cellulose through exposure to nitric acid or another powerful nitrating agent. When used as a propellant or low-order explosive, it is also known as guncotton...

 coatings and in vinyl films. For this reason it finds use in the manufacture of plastics, textiles, in the production of paraffin wax, and in household products such as lacquer
Lacquer
In a general sense, lacquer is a somewhat imprecise term for a clear or coloured varnish that dries by solvent evaporation and often a curing process as well that produces a hard, durable finish, in any sheen level from ultra matte to high gloss and that can be further polished as required...

, varnish
Varnish
Varnish is a transparent, hard, protective finish or film primarily used in wood finishing but also for other materials. Varnish is traditionally a combination of a drying oil, a resin, and a thinner or solvent. Varnish finishes are usually glossy but may be designed to produce satin or semi-gloss...

es, paint remover, a denaturing
Denaturation (biochemistry)
Denaturation is a process in which proteins or nucleic acids lose their tertiary structure and secondary structure by application of some external stress or compound, such as a strong acid or base, a concentrated inorganic salt, an organic solvent , or heat...

 agent for denatured alcohol, glues
Adhesive
An adhesive, or glue, is a mixture in a liquid or semi-liquid state that adheres or bonds items together. Adhesives may come from either natural or synthetic sources. The types of materials that can be bonded are vast but they are especially useful for bonding thin materials...

, and as a cleaning agent. It has similar solvent properties to acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...

 but has a significantly slower evaporation rate.
Butanone is also used in dry erase markers as the solvent of the erasable dye.

As a welding agent


As butanone dissolves 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...

, it is sold as "polystyrene cement" for use in connecting together parts of scale model
Scale model
A scale model is a physical model, a representation or copy of an object that is larger or smaller than the actual size of the object, which seeks to maintain the relative proportions of the physical size of the original object. Very often the scale model is used as a guide to making the object in...

 kits. Though often considered an adhesive
Adhesive
An adhesive, or glue, is a mixture in a liquid or semi-liquid state that adheres or bonds items together. Adhesives may come from either natural or synthetic sources. The types of materials that can be bonded are vast but they are especially useful for bonding thin materials...

, it is actually functioning as a welding
Welding
Welding is a fabrication or sculptural process that joins materials, usually metals or thermoplastics, by causing coalescence. This is often done by melting the workpieces and adding a filler material to form a pool of molten material that cools to become a strong joint, with pressure sometimes...

 agent in this context.

Other uses


Butanone is the precursor
Precursor (chemistry)
In chemistry, a precursor is a compound that participates in the chemical reaction that produces another compound. In biochemistry, the term "precursor" is used more specifically to refer to a chemical compound preceding another in a metabolic pathway....

 to methyl ethyl ketone peroxide
Methyl ethyl ketone peroxide
Methyl ethyl ketone peroxide is an organic peroxide, a high explosive similar to acetone peroxide. MEKP is a colorless, oily liquid whereas acetone peroxide is a white powder at STP; MEKP is slightly less sensitive to shock and temperature, and more stable in storage.Dilute solutions of 30 to 60%...

, a catalyst for some polymerization
Polymerization
In polymer chemistry, polymerization is a process of reacting monomer molecules together in a chemical reaction to form three-dimensional networks or polymer chains...

 reactions. It can also initiate crosslinking of unsaturated polyester resins.

Flammability


Butanone can react with most oxidizing materials, and can produce fires. It is moderately explosive; it requires only a small flame or spark to cause a vigorous reaction. Butanone fires should be extinguished with carbon dioxide
Carbon dioxide
Carbon dioxide is a naturally occurring chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom...

, dry chemicals or alcohol foam. Concentrations in the air high enough to be flammable are also intolerable to humans due to the irritating nature of the vapour.

Health effects


Butanone is an irritant
Irritation
Irritation or exacerbation, in biology and physiology, is a state of inflammation or painful reaction to allergy or cell-lining damage. A stimulus or agent which induces the state of irritation is an irritant...

, causing irritation to the eyes and nose of humans, but serious health effects in animals have been seen only at very high levels. When inhaled, these effects included birth defects.

Butanone is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances
United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances
The United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances of 1988 is one of three major drug control treaties currently in force. It provides additional legal mechanisms for enforcing the 1961 Single Convention on Narcotic Drugs and the 1971 Convention on...

.

On December 19, 2005, the U. S. Environmental Protection Agency removed butanone from the list of hazardous air pollutants (HAPs). After technical review and consideration of public comments, EPA concluded that potential exposures to butanone emitted from industrial processes may not reasonably be anticipated to cause human health or environmental problems. Emissions of butanone will continue to be regulated as a volatile organic compound because of its contribution to the formation of tropospheric (ground-level) ozone
Ozone
Ozone , or trioxygen, is a triatomic molecule, consisting of three oxygen atoms. It is an allotrope of oxygen that is much less stable than the diatomic allotrope...

.

External links