Pentenes are

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 ...

s with the

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

. Each contains one

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

within its molecular structure. Six different compounds are in this class, differing from each other by whether the

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 are attached linearly or in a branched structure, and whether the

has a ''cis'' or ''trans'' form.

Straight-chain isomers

1-Pentene is an

alpha-olefin In organic chemistry, alpha-olefins (or α-olefins) are a family of organic compounds which are alkenes (also known as olefins) with a chemical formula , distinguished by having a double bond at the primary or alpha (α) position.''Petrochemical ...

. Most often, 1-pentene is made as a byproduct of

catalytic Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

thermal cracking In petrochemistry, petroleum geology and organic chemistry, cracking is the process whereby complex organic molecules such as kerogens or long-chain hydrocarbons are broken down into simpler molecules such as light hydrocarbons, by the breaking of ...

petroleum 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 crud ...

, or during production 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 ...

and

propylene Propylene, also known as propene, is an unsaturated organic compound with the chemical formula CH3CH=CH2. It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petrole ...

via thermal cracking of hydrocarbon fractions. The only commercial manufacturer of 1-pentene is Sasol Ltd, where it is separated from crude made by the

Fischer–Tropsch process The Fischer–Tropsch process is a collection of chemical reactions that converts a mixture of carbon monoxide and hydrogen, known as syngas, into liquid hydrocarbons. These reactions occur in the presence of metal catalysts, typically at temperat ...

. 2-Pentene has two geometric isomers, ''cis''-2-pentene and ''trans''-2-pentene. ''Cis''-2-Pentene is used in

olefin metathesis Olefin metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins) by the scission and regeneration of carbon-carbon double bonds. Because of the relative simplicity of olefin metathesis, it often create ...

Branched-chain isomers

The branched isomers are 2-methylbut-1-ene, 3-methylbut-1-ene (isopentene), and

2-methylbut-2-ene 2-Methyl-2-butene, 2m2b, 2-methylbut-2-ene, also beta-isoamylene is an alkene hydrocarbon with the molecular formula C5H10. Used as a free radical scavenger in trichloromethane (chloroform) and dichloromethane (methylene chloride). John Snow, th ...

(isoamylene). Isoamylene is one of three main byproducts of

deep catalytic cracking Deep or The Deep may refer to: Places United States * Deep Creek (Appomattox River tributary), Virginia * Deep Creek (Great Salt Lake), Idaho and Utah * Deep Creek (Mahantango Creek tributary), Pennsylvania * Deep Creek (Mojave River tributary), C ...

(DCC), which is very similar to the operation of the

fluid 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 ...

(FCC). The DCC uses

vacuum gas oil Diesel fuel , also called diesel oil, is any liquid fuel specifically designed for use in a diesel engine, a type of internal combustion engine in which fuel ignition takes place without a spark as a result of compression of the inlet air and t ...

(VGO) as a feedstock to produce primarily

isobutylene 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 isoamylene. The rise in demand for

polypropylene Polypropylene (PP), also known as polypropene, is a thermoplastic polymer used in a wide variety of applications. It is produced via chain-growth polymerization from the monomer propylene. Polypropylene belongs to the group of polyolefins and ...

has encouraged the growth of the DCC, which is operated very much like FCC. Isobutylene and isoamylene feedstocks are necessary for the production of the much debated gasoline blending components methyl ''tert''-butyl ether and ''tert''-amyl methyl ether.

Production of fuels

Propylene, isobutene, and amylenes are feedstock in

alkylation unit An alkylation unit (alky) is one of the conversion processes used in petroleum refineries. It is used to convert isobutane and low-molecular-weight alkenes (primarily a mixture of propene and butene) into alkylate, a high octane gasoline componen ...

s of refineries. Using isobutane, blendstocks are generated with high branching for good combustion characteristics. Amylenes are valued as precursors to fuels, especially aviation fuels of relatively low volatility, as required by various regulations.

References

{{Hydrides by group Alkenes