But-2-ene is an acyclic

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...

with four

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...

atoms. It is the simplest alkene exhibiting ''cis''/''trans''-isomerism (also known as (''E''/''Z'')-isomerism); that is, it exists as two geometric

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...

s ''cis''-but-2-ene ((''Z'')-but-2-ene) and ''trans-''but-2-ene ((''E'')-but-2-ene). It is a

petrochemical Petrochemicals (sometimes abbreviated as petchems) are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sou ...

, produced by the

catalytic cracking Fluid Catalytic Cracking (FCC) is the conversion process used in petroleum refineries to convert the high-boiling point, high-molecular weight hydrocarbon fractions of petroleum (crude oils) into gasoline, olefinic gases, and other petroleum prod ...

crude oil Petroleum, also known as crude oil, or simply oil, is a naturally occurring yellowish-black liquid mixture of mainly hydrocarbons, and is found in geological formations. The name ''petroleum'' covers both naturally occurring unprocessed crude ...

or the dimerization of

ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...

. Its main uses are in the production of

gasoline Gasoline (; ) or petrol (; ) (see ) is a transparent, petroleum-derived flammable liquid that is used primarily as a fuel in most spark-ignited internal combustion engines (also known as petrol engines). It consists mostly of organic co ...

(petrol) and

butadiene 1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two viny ...

,. although some but-2-ene is also used to produce the solvent

butanone Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in n ...

via

hydration Hydration may refer to: * Hydrate, a substance that contains water * Hydration enthalpy, energy released through hydrating a substance * Hydration reaction, a chemical addition reaction where a hydroxyl group and proton are added to a compound * ...

2-butanol 2-Butanol, or ''sec''-butanol, is an organic compound with formula C H3CH( OH)CH2CH3. Its structural isomers are 1-butanol. isobutanol, and ''tert''-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated ...

followed by

oxidation Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...

. The two isomers are extremely difficult to separate by

distillation Distillation, or classical distillation, is the process of separation process, separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distilla ...

because of the proximity of their

boiling point The boiling point of a substance is the temperature at which the vapor pressure of a liquid equals the pressure surrounding the liquid and the liquid changes into a vapor. The boiling point of a liquid varies depending upon the surrounding envir ...

s (~4 °C for ''cis'' and ~1 °C for ''trans''Chemical Safety Information from Intergovernmental Organizations
). However, separation is unnecessary in most industrial settings, as both isomers behave similarly in most of the desired reactions. A typical industrial but-2-ene mixture is 70% (''Z'')-but-2-ene (''cis''-isomer) and 30% (''E'')-but-2-ene (''trans''-isomer).

Butane Butane () or ''n''-butane is an alkane with the formula C4H10. Butane is a gas at room temperature and atmospheric pressure. Butane is a highly flammable, colorless, easily liquefied gas that quickly vaporizes at room temperature. The name but ...

and

but-1-ene 1-Butene (or 1-Butylene) is the organic compound with the formula CH3CH2CH=CH2. It is a colorless gas that is easily condensed to give a colorless liquid. It is classified as a linear alpha-olefin. It is one of the isomers of butene (butylene). ...

are common impurities, present at 1% or more in industrial mixtures, which also contain smaller amounts of

isobutene Isobutylene (or 2-methylpropene) is a hydrocarbon with the chemical formula . It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value. Productio ...

and

butyne Butyne is an alkyne that contains 4 carbon and 6 hydrogen. It contains one triple bond and has two isomeric organic chemical compounds: *1-Butyne (ethylacetylene) *2-Butyne (dimethylacetylene) See also * Butane (C4H10) * Butene Butene, also kn ...

References

External links

* {{DEFAULTSORT:Butene, 2- Alkenes