| Revision as of 16:44, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475616642 of page 1-Octene for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 15:15, 22 December 2023 edit Nucleus hydro elemon (talk | contribs)Extended confirmed users3,319 edits Added {{More citations needed}} tagTag: Twinkle |
| Line 1: |
Line 1: |
|
|
{{More citations needed|date=December 2023}} |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{chembox |
|
{{Chembox |
|
| Watchedfields = changed |
|
| Watchedfields = changed |
|
| verifiedrevid = 443259510 |
|
| verifiedrevid = 477208427 |
|
| Name = 1-Octene |
|
| Name = 1-Octene |
|
| ImageFile = octene.png |
|
| ImageFile = octene.png |
|
<!-- | ImageSize = 200px --> |
|
| ImageSize = 220px |
|
| ImageName = 1-Octene |
|
| ImageName = 1-Octene |
|
|
| ImageFile1 = 1-Octene-3D-balls.png |
| ⚫ |
| IUPACName = Oct-1-ene |
|
|
|
| ImageSize1 = 220px |
| ⚫ |
| OtherNames = Octene-1, octylene; 1-n-ctene; hexylethylene; oct-1-ene; octene |
|
|
|
| ImageAlt1 = 1-Octene molecule |
| ⚫ |
| Section1 = {{Chembox Identifiers |
|
|
⚫ |
| PIN = Oct-1-ene |
| ⚫ |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
⚫ |
| OtherNames = Octene-1, octylene; 1-n-octene; hexylethylene; oct-1-ene; octene; caprylene |
|
⚫ |
|Section1={{Chembox Identifiers |
|
⚫ |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| ChEBI = 46708 |
|
| ChEBI = 46708 |
| Line 23: |
Line 26: |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo = 111-66-0 |
|
| CASNo = 111-66-0 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
| ⚫ |
| SMILES = C=CCCCCCC |
|
|
|
| UNII = E5VK21B9RC |
|
⚫ |
| SMILES = C=CCCCCCC |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| Formula = C<sub>8</sub>H<sub>16 |
|
| Formula = C<sub>8</sub>H<sub>16</sub> |
|
| MolarMass = 112.24 g/mol |
|
| MolarMass = 112.24 g/mol |
|
| Density = 0.715 g/cm³ |
|
| Density = 0.715 g/cm<sup>3</sup> |
|
|
| MeltingPtC = -101.7 |
|
| MeltingPt = -101.7 °C <ref name="nist">http://webbook.nist.gov/cgi/cbook.cgi?ID=C111660&Units=SI&Mask=1EFF</ref> |
|
| MeltingPt_ref =<ref name="nist">{{Cite web|url=https://webbook.nist.gov/cgi/cbook.cgi?ID=C111660&Units=SI&Mask=1EFF|title = 1-Octene}}</ref> |
| ⚫ |
| BoilingPt = 121 °C <ref name="nist"/> |
|
|
|
| BoilingPtC = 121 |
|
⚫ |
| BoilingPt_ref = <ref name="nist"/> |
|
}} |
|
}} |
|
}} |
|
}} |
|
|
|
|
|
'''1-Octene''' is an ] with a formula CH<sub>2</sub>CHC<sub>6</sub>H<sub>13</sub>. The ] is classified as a higher ] and ], meaning that the ] is located at the alpha (primary) position, endowing this compound with higher reactivity and thus useful chemical properties. 1-Octene is one of the important ]s in industry. It is a colourless liquid. |
|
|
|
|
|
==Synthesis== |
|
|
In industry, 1-octene is commonly manufactured by two main routes: ] of ] and by ] followed by purification. Another route to 1-octene that has been used commercially on a small scale is ] of ]s. Prior to the 1970s, 1-octene was also manufactured by thermal cracking of ]es, whereas linear internal ]s were also manufactured by ]/] of ]s. |
|
|
|
|
|
There are five commercial processes that ] ] to 1-octene. Four of these processes produce 1-octene as a part of a wide distribution of alpha-olefins. In typical circumstances, ] content of the entire distribution of alpha-olefins ranges from about 25% of the distribution in the ] (]) process to about 8% of distribution in some modes of the ] (CP Chemicals) and ] processes. |
|
|
|
|
|
The only commercial process to isolate 1-octene from a wide mixture of C<sub>8</sub> hydrocarbons is practiced by ], a ]n oil and gas and petrochemical company. For commercial purposes, Sasol employs ] to make fuels from ] derived from coal and recovers 1-octene from these fuel streams, where the initial 1-octene concentration in a narrow ] cut may be 60%, with the remainder being vinylidenes, linear and branched internal olefins, linear and branched paraffins, ]s, ]s, ]s, and ]s. |
|
|
|
|
|
Another route to 1-octene involves butadiene ] of butadiene. This technology was commercialized by Dow in a facility in ]. 1-Methoxy- |
|
|
2,7-octadiene is an intermediate in this process.<ref name=Beller>{{cite journal |doi=10.1039/D3IM00009E |title=Industrially applied and relevant transformations of 1,3-butadiene using homogeneous catalysts |date=2023 |last1=Yang |first1=Ji |last2=Wang |first2=Peng |last3=Neumann |first3=Helfried |last4=Jackstell |first4=Ralf |last5=Beller |first5=Matthias |journal=Industrial Chemistry & Materials |volume=1 |issue=2 |pages=155–174 |s2cid=258122761 |doi-access=free }}</ref> |
|
|
|
|
|
Yet another route converts 1-heptene to 1-octene plant based on a Fischer-Tropsch-derived C<sub>7</sub> olefin stream (Sasol, Secunda). |
|
|
|
|
|
Other 1-octene technologies exist based on selective tetramerisation of ethylene.<ref>{{cite journal |last1=Bollmann |first1=Annette |last2=Blann |first2=Kevin |last3=Dixon |first3=John T. |last4=Hess |first4=Fiona M. |last5=Killian |first5=Esna |last6=Maumela |first6=Hulisani |last7=McGuinness |first7=David S. |last8=Morgan |first8=David H. |last9=Neveling |first9=Arno |last10=Otto |first10=Stefanus |last11=Overett |first11=Matthew |last12=Slawin |first12=Alexandra M. Z. |last13=Wasserscheid |first13=Peter |last14=Kuhlmann |first14=Sven |year=2004 |title=Ethylene Tetramerization: A New Route to Produce 1-Octene in Exceptionally High Selectivities |journal=J. Am. Chem. Soc. |volume=126 |issue=45 |pages=14712–14713 |doi=10.1021/ja045602n|pmid=15535683 }}</ref> |
|
|
|
|
|
==Applications== |
|
|
The main use of 1-octene is as a ] in production of polyethylene. ] (HDPE) and ] (LLDPE) use approximately 2–4% and 8–10% of comonomers, respectively. |
|
|
|
|
|
Another significant use of 1-octene is for production of linear ] via oxo synthesis (]) to give the C9 aldehyde (]). Oxidation of this aldehyde gives the short-chain ] ]. Hydrogenation of the same aldehyde gives the ] ], which is used as a ]. |
|
|
|
|
|
==References== |
|
|
{{Reflist}} |
|
|
|
|
|
{{Hydrides by group}} |
|
|
|
|
|
{{DEFAULTSORT:Octene, 1-}} |
|
|
] |