Decene (original) (raw)

From Wikipedia, the free encyclopedia

Organic compound (C10H20)

Decene
Names
Preferred IUPAC name Dec-1-ene
Other namesAlpha Olefin C10; Decylene; α-Decene; 1-decene
Identifiers
CAS Number 872-05-9 checkY
3D model (JSmol) Interactive image
ChEBI CHEBI:87315
ChEMBL ChEMBL3187990
ChemSpider 12809 checkY
ECHA InfoCard 100.011.654 Edit this at Wikidata
EC Number 212-819-2
PubChem CID 13381
RTECS number HE2071401
UNII 7O4U4C718P checkY
UN number 3295, 1993
CompTox Dashboard (EPA) DTXSID8027329 Edit this at Wikidata
InChI InChI=1S/C10H20/c1-3-5-7-9-10-8-6-4-2/h3H,1,4-10H2,2H3 checkYKey: AFFLGGQVNFXPEV-UHFFFAOYSA-N checkYInChI=1/C10H20/c1-3-5-7-9-10-8-6-4-2/h3H,1,4-10H2,2H3Key: AFFLGGQVNFXPEV-UHFFFAOYAO
SMILES CCCCCCCCC=C
Properties
Chemical formula C10H20
Molar mass 140.270 g·mol−1
Density 0.74 g/cm3[1]
Melting point −66.3 °C (−87.3 °F; 206.8 K)[1]
Boiling point 172 °C (342 °F; 445 K)[1]
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H226, H304, H410
Precautionary statements P210, P233, P240, P241, P242, P243, P273, P280, P301+P310, P303+P361+P353, P331, P370+P378, P391, P403+P235, P405, P501
Related compounds
Related Alkenes OcteneNoneneUndeceneDodecene
Related compounds DecaneDecanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). checkY verify (what is checkY☒N ?) Infobox references

Chemical compound

Decene is an organic compound with the chemical formula C10H20. Decene contains a chain of ten carbon atoms with one double bond, making it an alkene. There are many isomers of decene depending on the position and geometry of the double bond. Dec-1-ene is the only isomer of industrial importance. As an alpha olefin, it is used as a comonomer in copolymers and is an intermediate in the production of epoxides, amines, oxo alcohols, synthetic lubricants, synthetic fatty acids and alkylated aromatics.[2]

The industrial processes used in the production of dec-1-ene are oligomerization of ethylene by the Ziegler process or by the cracking of petrochemical waxes.[3]

In ethenolysis, methyl oleate, the methyl ester of oleic acid, converts to 1-decene and methyl 9-decenoate:[4]

CH 3 ( CH 2 ) 7 CH = CH ( CH 2 ) 7 CO 2 Me methyl oleate + CH 2 = CH 2 ⟶ CH 3 ( CH 2 ) 7 CH = CH 2 1-decene + MeO 2 C ( CH 2 ) 7 CH = CH 2 9-decenoate {\displaystyle {\overset {\text{methyl oleate}}{{\ce {CH3(CH2)7CH=CH(CH2)7CO2Me}}}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\overset {\text{1-decene}}{{\ce {CH3(CH2)7CH=}}{\color {red}{\ce {CH2}}}}}+{\overset {\text{9-decenoate}}{{\ce {MeO2C(CH2)7CH=}}{\color {red}{\ce {CH2}}}}}} {\displaystyle {\overset {\text{methyl oleate}}{{\ce {CH3(CH2)7CH=CH(CH2)7CO2Me}}}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\overset {\text{1-decene}}{{\ce {CH3(CH2)7CH=}}{\color {red}{\ce {CH2}}}}}+{\overset {\text{9-decenoate}}{{\ce {MeO2C(CH2)7CH=}}{\color {red}{\ce {CH2}}}}}}

Dec-1-ene has been isolated from the leaves and rhizome of the plant Farfugium japonicum and has been detected as the initial product in the microbial degradation of _n_-decane.

  1. ^ a b c Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ http://www.ineosoligomers.com/media/files/lao/LAO%20C10%20Data%20Sheet.pdf 1-Decene (Alpha Olefin C10)], ineosoligomers.com
  3. ^ Alfa Olefins Archived 2017-05-17 at the Wayback Machine, SIDS Initial Assessment Report
  4. ^ Marinescu, Smaranda C.; Schrock, Richard R.; Müller, Peter; Hoveyda, Amir H. (2009). "Ethenolysis Reactions Catalyzed by Imido Alkylidene Monoaryloxide Monopyrrolide (MAP) Complexes of Molybdenum". J. Am. Chem. Soc. 131 (31): 10840–10841. doi:10.1021/ja904786y. PMID 19618951.