Cyclopentene

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Cyclopentene
Cyclopentene Cyclopentene-2D-skeletal.png
Cyclopentene
Ball-and-stick model of cyclopentene Cyclopentene-3D-balls.png
Ball-and-stick model of cyclopentene
Cyclopentene-3D-vdW.png
Names
Preferred IUPAC name
Cyclopentene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.030 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C5H8/c1-2-4-5-3-1/h1-2H,3-5H2 Yes check.svgY
    Key: LPIQUOYDBNQMRZ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C5H8/c1-2-4-5-3-1/h1-2H,3-5H2
    Key: LPIQUOYDBNQMRZ-UHFFFAOYAS
  • C1CC=CC1
Properties
C5H8
Molar mass 68.11 g/mol
Density 0.771 g/cm3
Melting point −135 °C (−211 °F; 138 K)
Boiling point 44 to 46 °C (111 to 115 °F; 317 to 319 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
3
1
Flash point −29 °C (−20 °F; 244 K)
Related compounds
Related compounds
Cyclopentadiene
Cyclobutene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclopentene is a chemical compound with the formula (CH2)3(CH)2. It is a colorless liquid with a petrol-like odor. It has few applications, and thus is mainly used as a minor component of gasoline, present in concentrations of less than 1%. [1] [2] It is one of the principal cycloalkenes.

Contents

Production

Cyclopentene is produced industrially in large amounts by steam cracking of naphtha. In the laboratory, it is prepared by dehydration of cyclopentanol. [3]

It can also produced by the catalytic hydrogenation of cyclopentadiene. [4]

Cyclopentadiene hydrogenation.png

Reactions

Cyclopentene can be obtained from vinylcyclopropane in the vinylcyclopropane-cyclopentene rearrangement. [5]

The polymerization of cyclopentene by Ziegler-Natta catalysts yields 1,3-linkages, not the more typical 1,2-linked polymer. [6]

Palladium-catalyzed hydrocarboxylation of cyclopentene gives cyclopentanecarboxylic acid: [7]

C5H8 + CO + H2O → C5H9CO2H

Related Research Articles

<span class="mw-page-title-main">Catalysis</span> Process of increasing the rate of a chemical reaction

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Cyclopentadiene is an organic compound with the formula C5H6. It is often abbreviated CpH because the cyclopentadienyl anion is abbreviated Cp.

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

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<span class="mw-page-title-main">Olefin metathesis</span> Organic reaction involving the breakup and reassembly of alkene double bonds

In organic chemistry, 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 creates fewer undesired by-products and hazardous wastes than alternative organic reactions. For their elucidation of the reaction mechanism and their discovery of a variety of highly active catalysts, Yves Chauvin, Robert H. Grubbs, and Richard R. Schrock were collectively awarded the 2005 Nobel Prize in Chemistry.

Coordination polymerisation is a form of polymerization that is catalyzed by transition metal salts and complexes.

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

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

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

Diethylaluminium chloride, abbreviated DEAC, is an organoaluminium compound. Although usually given the chemical formula (C2H5)2AlCl, it exists as a dimer, [(C2H5)2AlCl]2 It is a precursor to Ziegler-Natta catalysts employed for the production of polyolefins. The compound is also a Lewis acid, useful in organic synthesis. The compound is a colorless waxy solid, but is usually handled as a solution in hydrocarbon solvents. It is highly reactive, even pyrophoric.

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References

  1. Dieter Hönicke; Ringo Födisch; Peter Claus; Michael Olson (2002). "Cyclopentadiene and Cyclopentene". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_227.
  2. "Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks". nepis.epa.gov. United States Environmental Protection Agency. 2011.
  3. B. B. Corson, V. N. Ipatieff (1939). "Cyclohexylbenzene". Organic Syntheses. 19: 36. doi:10.15227/orgsyn.019.0036.
  4. D. Hönicke, R. Födisch, P. Claus, M. Olson: Cyclopentadiene and Cyclopentene, in: Ullmanns Enzyklopädie der Technischen Chemie 2002, Wiley-VCH, Weinheim.
  5. Baldwin, John E. (2003). "Thermal Rearrangements of Vinylcyclopropanes to Cyclopentenes". Chemical Reviews. 103 (4): 1197–212. doi:10.1021/cr010020z. PMID   12683781.
  6. Collins, Scott; Kelly, W. Mark (1992). "The microstructure of poly(cyclopentene) produced by polymerization of cyclopentene with homogeneous Ziegler-Natta catalysts". Macromolecules. 25 (1): 233–7. Bibcode:1992MaMol..25..233C. doi:10.1021/ma00027a039.
  7. Sang, Rui; Kucmierczyk, Peter; Dühren, Ricarda; Razzaq, Rauf; Dong, Kaiwu; Liu, Jie; Franke, Robert; Jackstell, Ralf; Beller, Matthias (2019). "Synthesis of Carboxylic Acids by Palladium‐Catalyzed Hydroxycarbonylation". Angewandte Chemie International Edition. 58 (40): 14365–14373. doi: 10.1002/anie.201908451 . PMID   31390131. S2CID   199466915.