1-Dodecene

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1-Dodecene is an alkene with the formula C10H21CH=CH2, consisting of a chain of twelve carbon atoms ending with a double bond. While there are many isomers of dodecene depending on which carbon the double bond is placed, this isomer is of greater commercial importance. It is classified as an alpha-olefin. Alpha-olefins are distinguished by having a double bond at the primary or alpha (α) position. This location of a double bond enhances the reactivity of the compound and makes it useful for a number of applications, especially for the production of detergents.[4]

1-Dodecene
Names
Preferred IUPAC name
Dodec-1-ene
Other names
1-Dodecene
α-Dodecene
Dodecene-1
Adacene 12
Dodecylene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.608 Edit this at Wikidata
EC Number
  • 203-968-4
UNII
  • InChI=1S/C12H24/c1-3-5-7-9-11-12-10-8-6-4-2/h3H,1,4-12H2,2H3
  • CCCCCCCCCCC=C
Properties
C12H24
Molar mass 168.324 g·mol−1
Appearance colorless liquid with a mild, pleasant odor.[1]
Density 0.7584 g/cm3 [2]
Melting point −35.2 °C (−31.4 °F; 238.0 K)[2]
Boiling point 213.8˚C[2]
Insoluble
Solubility Soluble in ethanol, ethyl ether, and acetone
Vapor pressure 0.0159 mm Hg at 25 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Irritates skin and eyes, harmful if swallowed, wear safety glasses and have adequate ventilation [3]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
2
0
Flash point 77 °C (171 °F; 350 K)
Related compounds
Related Alkenes
Octene
Nonene
Undecene
Dodecene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Production and reactions

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1-Dodecene is commercially produced by oligomerization of ethylene via a number of processes. In the Shell Higher Olefin Process (SHOP), a nickel catalyst is employed. In processes developed by Gulf and by Ethyl Corporations, triethylaluminium is the catalyst. Similar to the SHOP method, these processes rely on ethylene insertion into an Al-alkyl bond competitively with beta-hydride elimination to give the alpha-olefin, regenerating an aluminium hydride. Other processes have been developed.[5][6]

References

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  1. ^ "1-DODECENE | CAMEO Chemicals | NOAA".
  2. ^ a b c "1-Dodecene".
  3. ^ "Dodecene | C12H24 | ChemSpider".
  4. ^ Kurt Kosswig,"Surfactants" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2005, Weinheim. doi:10.1002/14356007.a25_747
  5. ^ Schmidt, Roland; Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2014). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–74. doi:10.1002/14356007.a13_227.pub3. ISBN 9783527306732.
  6. ^ "ChemSystems: Return on Analysis for Investment in the Petrochemical Industry: Markets, Technology, Profitability and Prices". Archived from the original on 2011-08-31. Retrieved 2012-10-19.