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But-2-ene

(Redirected from Cis-2-Butene)

But-2-ene 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-but-2-ene ((Z)-but-2-ene) and trans-but-2-ene ((E)-but-2-ene).

But-2-ene
cis
trans
cis
trans
Names
Preferred IUPAC name
But-2-ene
Other names
β-Butylene
Identifiers
3D model (JSmol)
1718755 1361341
ChEBI
ChemSpider
ECHA InfoCard 100.003.140 Edit this at Wikidata
EC Number
  • 203-452-9
25196 1140 1141
RTECS number
  • EM2932000 1718756
UNII
  • InChI=1S/C4H8/c1-3-4-2/h3-4H,1-2H3 checkY
    Key: IAQRGUVFOMOMEM-UHFFFAOYSA-N checkY
  • InChI=1/C4H8/c1-3-4-2/h3-4H,1-2H3
    Key: IAQRGUVFOMOMEM-UHFFFAOYAW
  • (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, 3.7 °C)[1]
0.626 g/ml (trans, 0.9 °C)[2]
Melting point −138.9 °C (−218.0 °F; 134.2 K) (cis)[1]
-105.5 °C (trans)[2]
Boiling point 0.8 to 3.7 °C (33.4 to 38.7 °F; 273.9 to 276.8 K) (Z = 3.7 °C)[1]
(E = 0.8 °C)[2]
  • -42.6·10−6 cm3/mol (cis)
  • -43.3·10−6 cm3/mol (trans)
Hazards[3]
GHS labelling:
Flam. Gas 1Press. Gas
Danger
H220
P210, P377, P381, P403
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 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 −72 °C (−98 °F; 201 K)[1][2]
325 °C (617 °F; 598 K)[1][2]
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 checkY☒N ?)

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 high-octane gasoline (petrol) on alkylation units and butadiene,[4] although some but-2-ene is also used to produce the solvent butanone via hydration reaction to butan-2-ol 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[5]). 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 and but-1-ene are common impurities, present at 1% or more in industrial mixtures, which also contain smaller amounts of isobutene, butadiene and butyne.[4]

References

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  1. ^ a b c d e Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ a b c d e Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ^ cis-2-Butene, International Chemical Safety Card 0397, Geneva: International Programme on Chemical Safety, March 1996. trans-2-Butene, International Chemical Safety Card 0398, Geneva: International Programme on Chemical Safety, March 1996.
  4. ^ a b 2-Butene (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, February 1995.
  5. ^ Chemical Safety Information from Intergovernmental Organizations Archived December 9, 2009, at the Wayback Machine
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