1-Butene

Last updated
1-Butene
1-butene.svg
1-Butene.svg
But-1-ene-3D-balls.png
Names
Preferred IUPAC name
But-1-ene [1]
Other names
Ethylethylene
1-Butylene
α-Butylene
Identifiers
3D model (JSmol)
1098262
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.137 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-449-2
25205
PubChem CID
UNII
UN number 1012
  • InChI=1S/C4H8/c1-3-4-2/h3H,1,4H2,2H3 Yes check.svgY
    Key: VXNZUUAINFGPBY-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H8/c1-3-4-2/h3H,1,4H2,2H3
    Key: VXNZUUAINFGPBY-UHFFFAOYAZ
  • C=CCC
  • CCC=C
Properties
C4H8
Molar mass 56.108 g·mol−1
AppearanceColorless Gas
Odor slightly aromatic
Density 0.62 g/cm3
Melting point −185.3 °C (−301.5 °F; 87.8 K)
Boiling point −6.47 °C (20.35 °F; 266.68 K)
0.221 g/100 mL
Solubility soluble in alcohol, ether, benzene
1.3962
Viscosity 7.76 Pa
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-bottle.svg
Danger
H220, H221, H280
P210, P377, P381, P403, P410+P403
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
4
0
Flash point −79 °C; −110 °F; 194 K
385 °C (725 °F; 658 K)
Explosive limits 1.6-10%
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

1-Butene (IUPAC name: But-1-ene, also known as 1-butylene) is the organic compound with the formula CH3CH2CH=CH2. It is a colorless gas. But-1-ene is an alkene easily condensed to give a colorless liquid. It is classified as a linear alpha-olefin (terminal alkene). [2] It is one of the isomers of butene (butylene). It is a precursor to diverse products.

Contents

Reactions

Polymerization of but-1-ene gives polybutylene, which is used to make piping for domestic plumbing. [3] Another application is as a comonomer in the production of certain kinds of polyethylene, such as linear low-density polyethylene (LLDPE). [4] It has also been used as a precursor to polypropylene resins, butylene oxide, and butanone. [5]

Manufacturing

But-1-ene is produced by separation from crude C4 refinery streams and by ethylene dimerization. The former affords a mixture of 1-and 2-butenes, while the latter affords only the terminal alkene. [6] It is distilled to give a very high purity product. An estimated 12 billion kilograms were produced in 2011. [7]

Related Research Articles

<span class="mw-page-title-main">Alkene</span> Hydrocarbon compound containing one or more C=C bonds

In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins.

<span class="mw-page-title-main">Ethylene</span> Hydrocarbon compound (H₂C=CH₂)

Ethylene is a hydrocarbon which has the formula C2H4 or H2C=CH2. It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene.

<span class="mw-page-title-main">Pentaerythritol</span> Chemical compound

Pentaerythritol is an organic compound with the formula C(CH2OH)4. Classified as a polyol, it is a white solid. Pentaerythritol is a building block for the synthesis and production of explosives, plastics, paints, appliances, cosmetics, and many other commercial products.

<span class="mw-page-title-main">Cumene process</span> Industrial process

The cumene process is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene, the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR), and independently by Heinrich Hock in 1944.

In chemistry, isomerization or isomerisation is the process in which a molecule, polyatomic ion or molecular fragment is transformed into an isomer with a different chemical structure. Enolization is an example of isomerization, as is tautomerization. When the isomerization occurs intramolecularly it may be called a rearrangement reaction.

<span class="mw-page-title-main">Epoxide</span> Organic compounds with a carbon-carbon-oxygen ring

In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.

Butene, also known as butylene, is an alkene with the formula C4H8. The word butene may refer to any of the individual compounds. They are colourless gases that are present in crude oil as a minor constituent in quantities that are too small for viable extraction. Butene is therefore obtained by catalytic cracking of long-chain hydrocarbons left during refining of crude oil. Cracking produces a mixture of products, and the butene is extracted from this by fractional distillation.

<span class="mw-page-title-main">Isobutylene</span> Unsaturated hydrocarbon compound (H2C=C(CH3)2)

Isobutylene is a hydrocarbon with the chemical formula (CH3)2C=CH2. 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.

Octene is an alkene with the formula C
8
H
16
. Several isomers of octene are known, depending on the position and the geometry of the double bond in the carbon chain.

A polyolefin is a type of polymer with the general formula (CH2CHR)n where R is an alkyl group. They are usually derived from a small set of simple olefins (alkenes). Dominant in a commercial sense are polyethylene and polypropylene. More specialized polyolefins include polyisobutylene and polymethylpentene. They are all colorless or white oils or solids. Many copolymers are known, such as polybutene, which derives from a mixture of different butene isomers. The name of each polyolefin indicates the olefin from which it is prepared; for example, polyethylene is derived from ethylene, and polymethylpentene is derived from 4-methyl-1-pentene. Polyolefins are not olefins themselves because the double bond of each olefin monomer is opened in order to form the polymer. Monomers having more than one double bond such as butadiene and isoprene yield polymers that contain double bonds (polybutadiene and polyisoprene) and are usually not considered polyolefins. Polyolefins are the foundations of many chemical industries.

<span class="mw-page-title-main">Terminal alkene</span> Hydrocarbon compounds with a C=C bond at the alpha carbon

In organic chemistry, terminal alkenes are a family of organic compounds which are alkenes with a chemical formula CxH2x, distinguished by having a double bond at the primary, alpha (α), or 1- position. This location of a double bond enhances the reactivity of the compound and makes it useful for a number of applications.

<span class="mw-page-title-main">Enol ether</span> Class of chemical compounds

In organic chemistry an enol ether is an alkene with an alkoxy substituent. The general structure is R2C=CR-OR where R = H, alkyl or aryl. A common subfamily of enol ethers are vinyl ethers, with the formula ROCH=CH2. Important enol ethers include the reagent 3,4-dihydropyran and the monomers methyl vinyl ether and ethyl vinyl ether.

2,6-Di-<i>tert</i>-butylphenol Chemical compound

2,6-Di-tert-butylphenol is an organic compound with the structural formula 2,6-((CH3)3C)2C6H3OH. This colorless solid alkylated phenol and its derivatives are used industrially as UV stabilizers and antioxidants for hydrocarbon-based products ranging from petrochemicals to plastics. Illustrative of its usefulness, it prevents gumming in aviation fuels.

<span class="mw-page-title-main">Methacrylic acid</span> Chemical compound

Methacrylic acid, abbreviated MAA, is an organic compound with the formula CH2=C(CH3)CO2H. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA), and to poly(methyl methacrylate) (PMMA).

<span class="mw-page-title-main">Methyl vinyl ketone</span> Chemical compound

Methyl vinyl ketone (MVK, IUPAC name: butenone) is the organic compound with the formula CH3C(O)CH=CH2. It is a reactive compound classified as an enone, in fact the simplest example thereof. It is a colorless, flammable, highly toxic liquid with a pungent odor. It is soluble in water and polar organic solvents. It is a useful intermediate in the synthesis of other compounds.

Synthetic resins are industrially produced resins, typically viscous substances that convert into rigid polymers by the process of curing. In order to undergo curing, resins typically contain reactive end groups, such as acrylates or epoxides. Some synthetic resins have properties similar to natural plant resins, but many do not.

In inorganic chemistry, sulfonyl halide groups occur when a sulfonyl functional group is singly bonded to a halogen atom. They have the general formula RSO2X, where X is a halogen. The stability of sulfonyl halides decreases in the order fluorides > chlorides > bromides > iodides, all four types being well known. The sulfonyl chlorides and fluorides are of dominant importance in this series.

<span class="mw-page-title-main">Pentanal</span> Chemical compound

Pentanal is the organic compound with molecular formula C4H9CHO. Classified as an alkyl aldehyde, it is a colorless volatile liquid. Its odor is described as fermented, bready, fruity, nutty, berry.

<span class="mw-page-title-main">1,3-Butanediol</span> Chemical compound

1,3-Butanediol is an organic compound with the formula CH3CH(OH)CH2CH2OH. With two alcohol functional groups, the molecule is classified as a diol. The compound is also chiral, but most studies do not distinguish the enantiomers. The compound is a colorless, bittersweet, water-soluble liquid. It is one of four common structural isomers of butanediol. It is used in flavoring.

In polymer chemistry, a comonomer refers to a polymerizable precursor to a copolymer aside from the principal monomer. In some cases, only small amounts of a comonomer are employed, in other cases substantial amounts of comonomers are used. Furthermore, in some cases, the comonomers are statistically incorporated within the polymer chain, whereas in other cases, they aggregate. The distribution of comonomers is referred to as the "blockiness" of a copolymer.

References

  1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 17, 61, 374. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4.
  2. "1-BUTENE". chemicalland21.com. Retrieved 22 April 2018.
  3. Whiteley, Kenneth S.; Heggs, T. Geoffrey; Koch, Hartmut; Mawer, Ralph L.; Immel, Wolfgang (2000). "Polyolefins". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a21_487. ISBN   978-3527306732.
  4. Chum, P. Steve; Swogger, Kurt W. (2008). "Olefin polymer technologies—History and Recent Progress at the Dow Chemical Company". Progress in Polymer Science. 33 (8): 797–819. doi:10.1016/j.progpolymsci.2008.05.003.
  5. "1-Butene product overview". shell.com. Archived from the original on 2012-02-10. Retrieved 22 April 2018.
  6. "Alphabutol process - Big Chemical Encyclopedia". chempedia.info. Archived from the original on 2017-12-08. Retrieved 22 April 2018.
  7. Geilen, Frank M.A.; Stochniol, Guido; Peitz, Stephan; Schulte-Koerne, Ekkehard (2014). "Butenes". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_483.pub3. ISBN   978-3527306732.