2-Butene

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2-Butene
cis
trans
Cis-but-2-ene-3D-balls.png
cis
Trans-but-2-ene-3D-balls.png
trans
Names
IUPAC name
But-2-ene
Other names
β-Butylene
Identifiers
107-01-7 YesY
590-18-1 (cis) YesY
624-64-6 (trans) YesY
ChEBI CHEBI:48363 YesY
ChemSpider 11719 YesY
4449912 (cis) N
56442 (trans) N
EC Number 203-452-9
Jmol 3D model Interactive image
(cis): Interactive image
(trans): Interactive image
PubChem 5287573 (cis)
62695 (trans)
RTECS number EM2932000
UNII S1SK37516R YesY
  • InChI=1S/C4H8/c1-3-4-2/h3-4H,1-2H3 YesY
    Key: IAQRGUVFOMOMEM-UHFFFAOYSA-N YesY
  • InChI=1/C4H8/c1-3-4-2/h3-4H,1-2H3
    Key: IAQRGUVFOMOMEM-UHFFFAOYAW
  • (cis): InChI=1/C4H8/c1-3-4-2/h3-4H,1-2H3/b4-3-
    Key: IAQRGUVFOMOMEM-ARJAWSKDBO
  • (trans): InChI=1/C4H8/c1-3-4-2/h3-4H,1-2H3/b4-3+
    Key: IAQRGUVFOMOMEM-ONEGZZNKBD
  • (cis): InChI=1S/C4H8/c1-3-4-2/h3-4H,1-2H3/b4-3-
    Key: IAQRGUVFOMOMEM-ARJAWSKDSA-N
  • (trans): InChI=1S/C4H8/c1-3-4-2/h3-4H,1-2H3/b4-3+
    Key: IAQRGUVFOMOMEM-ONEGZZNKSA-N
  • C(=CC)C
  • (cis): C/C=C\C
  • (trans): C/C=C/C
Properties
C4H8
Molar mass 56.106 g/mol
Density 0.641 g/mL (cis, at 3.7 °C)[1]
0.626 g/mL (trans, at 0.9 °C)[2]
Melting point -138.9 ºC (cis)[1]
-105.5 °C (trans)[2]
Boiling point 3.7 ºC (cis)[1]
0.9 °C (trans)[2]
Vapor pressure {{{value}}}
Related compounds
Related butenes
1-Butene
cis-2-Butene
trans-2-Butene
Isobutene
Related compounds
Butane
Butyne
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

2-Butene is an acyclic alkene with four carbon atoms. It is the simplest alkene exhibiting cis/trans-isomerism (also known as (E/Z)-isomerism); that is, it exists as two geometric isomers cis-2-butene ((Z)-2-butene) and trans-2-butene ((E)-2-butene).

It is a petrochemical, produced by the catalytic cracking of crude oil or the dimerization of ethylene. Its main uses are in the production of gasoline (petrol) and butadiene,[3] although some 2-butene is also used to produce the solvent butanone via hydration to 2-butanol followed by oxidation.

The two isomers are extremely difficult to separate by distillation because of the proximity of their boiling points (~4 °C for cis and ~1 °C for trans[4]). However, separation is unnecessary in most industrial settings, as both isomers behave similarly in most of the desired reactions. A typical industrial 2-butene mixture is 70% (Z)-2-butene (cis-isomer) and 30% (E)-2-butene (trans-isomer). Butane and 1-butene are common impurities, present at 1% or more in industrial mixtures, which also contain smaller amounts of isobutene, butadiene and butyne.[3]

References

  1. 1.0 1.1 1.2 Record in the GESTIS Substance Database of the IFA
  2. 2.0 2.1 2.2 Record in the GESTIS Substance Database of the IFA
  3. 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found..
  4. Chemical Safety Information from Intergovernmental Organizations Archived December 9, 2009 at the Wayback Machine

External links