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]
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| Names | |
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| Preferred IUPAC name
Dodec-1-ene | |
| Other names
1-Dodecene
α-Dodecene Dodecene-1 Adacene 12 Dodecylene | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.003.608 |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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
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Irritates skin and eyes, harmful if swallowed, wear safety glasses and have adequate ventilation [3] |
| NFPA 704 (fire diamond) | |
| Flash point | 77 °C (171 °F; 350 K) |
| Related compounds | |
Related Alkenes
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Octene Nonene Undecene Dodecene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Production and reactions
edit1-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
edit- ^ "1-DODECENE | CAMEO Chemicals | NOAA".
- ^ a b c "1-Dodecene".
- ^ "Dodecene | C12H24 | ChemSpider".
- ^ Kurt Kosswig,"Surfactants" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2005, Weinheim. doi:10.1002/14356007.a25_747
- ^ 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.
- ^ "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.