View source for 1-Hexene

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477207844
| Name = 1-Hexene
| ImageFile = 1-hexene.svg
| ImageSize = 
| ImageName = 1-Hexene
| ImageFile1 = 1-Hexene-3D-balls.png
| ImageAlt1 = 1-Hexene molecule
| PIN = Hex-1-ene
| OtherNames = Hexene, Hexylene, Butyl ethylene
|Section1={{Chembox Identifiers
| SMILES = C=CCCCC
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 11109
| ChEBI_Ref = {{ebicite|correct|EBI}} 
| ChEBI = 24579
| PubChem = 11597
| EINECS = 209-753-1
| RTECS = MP6670000
| UNNumber = 2370
| UNII = B38ZZ8C206
| ChEMBL = 1548726
| InChI = 1/C6H12/c1-3-5-6-4-2/h3H,1,4-6H2,2H3
| InChIKey = LIKMAJRDDDTEIG-UHFFFAOYAY
| SMILES1 = CCCCC=C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H12/c1-3-5-6-4-2/h3H,1,4-6H2,2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LIKMAJRDDDTEIG-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 592-41-6
  }}
|Section2={{Chembox Properties
| C=6|H=12
| Appearance = Colorless liquid
| Density = 0.673 g/cm<sup>3</sup>
| Solubility = Insoluble
| MeltingPtC = −139.8
| MeltingPt_notes =
| BoilingPtC = 63
| Viscosity = 0.51 [[Poise (unit)|cP]] (0.51 mPa·s) at 28°C
  }}
|Section3={{Chembox Structure
| Dipole =
  }}
|Section7={{Chembox Hazards
| ExternalSDS =[http://hazard.com/msds/mf/baker/baker/files/h2740.htm External MSDS]
| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|225|304|319}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|264|280|301+310|303+361+353|305+351+338|331|337+313|370+378|403+235|405|501}}
  }}
}}

'''1-Hexene''' ('''hex-1-ene''') is an [[organic compound]] with the formula C<sub>6</sub>H<sub>12</sub>.  It is an [[alkene]] that is classified in industry as higher [[olefin]] and an [[alpha-olefin]], the latter term meaning that the double bond is located at the alpha (primary) position, endowing the compound with higher reactivity and thus useful chemical properties. 1-Hexene is an industrially significant [[linear alpha olefin]].  It is a colourless liquid.

==Production==
1-Hexene is commonly manufactured by two general routes: (i) full-range processes via the [[oligomerization]] of [[ethylene]] and (ii) on-purpose technology. A minor route to 1-hexene, used commercially on smaller scales, is the [[Dehydration reaction|dehydration]] of [[hexanol]].  Prior to the 1970s, 1-hexene was also manufactured by the thermal cracking of waxes. Linear internal hexenes were manufactured by [[halogenation|chlorination]]/[[dehydrochlorination]] of [[linear paraffins]].<ref> Lappin, George (Editor), Alpha Olefins Applications Handbook, Marcel Dekker Inc., {{ISBN|978-0-8247-7895-8}}</ref>

"Ethylene [[oligomerization]]" combines ethylene molecules to produce linear alpha-olefins of various chain lengths with an even number of carbon atoms.  This approach result in a distribution or “full range” of alpha-olefins. The [[Shell higher olefin process]] (SHOP) employs this approach. [[The Linde Group|Linde]] and [[SABIC]] have developed the α-SABLIN technology using the oligomerization of ethylene to produce 21 percent 1-hexene. CP Chemicals and Innovene also have full-range processes. Typically, 1-hexene content ranges from about twenty percent distribution in the Ethyl (Innovene) process, whereas only twelve percent of distribution in the CP Chemicals and [[Idemitsu]] processes.

An on purpose route to 1-hexene using ethylene trimerization was first brought on stream in Qatar in 2003 by Chevron-Phillips. A second plant was scheduled to start in 2011 in Saudi Arabia and a third planned for 2014 in the US.<ref>(18 October 2010) [http://www.plastinfo.net/information/news/2544_18.10.2010/ Chevron Phillips Chemical announces plans for world-scale 1-hexene plant] {{Webarchive|url=https://web.archive.org/web/20141129125304/http://www.plastinfo.net/information/news/2544_18.10.2010/ |date=2014-11-29 }} Plastinfo, Plastics Industry Directory, Retrieved 30 September 2011</ref> The [[Sasol]] process is also considered an on-purpose route to 1-hexene. Sasol commercially employs [[Fischer–Tropsch]] synthesis to make fuels from [[synthesis gas]] derived from coal. The synthesis recovers 1-hexene from the aforementioned fuel streams, where the initial 1-hexene concentration cut may be 60% in a narrow distillation, with the remainder being [[vinylidenes]], linear and branched internal olefins, linear and branched paraffins, [[Alcohol (chemistry)|alcohol]]s, [[aldehyde]]s, [[carboxylic acid]]s, and [[aromatic compound]]s.  The trimerization of ethylene by homogeneous catalysts has been demonstrated.<ref>David S. McGuinness, Peter Wasserscheid, Wilhelm Keim, David Morgan, John T. Dixon, Annette Bollmann, Hulisani Maumela, Fiona Hess, and Ulli Englert "First Cr(III)−SNS Complexes and Their Use as Highly Efficient Catalysts for the Trimerization of Ethylene to 1-Hexene" J. Am. Chem. Soc., 2003, volume 125, pp 5272–5273.
{{doi|10.1021/ja034752f}}.</ref> An alternative on-purpose route has been reported by Lummus Technology.<ref>{{Cite web|url=http://www.ihs.com/products/chemical/technology/pep/reviews/lummus-cb-i-hexene-from-c4.aspx|title = To make better decisions, you need to see the big picture}}</ref>

==Applications==
The primary use of 1-hexene is as a [[comonomer]] in production of [[polyethylene]]. [[High-density polyethylene]] (HDPE) and [[linear low-density polyethylene]] (LLDPE) use approximately 2–4% and 8–10% of comonomers, respectively.

Another significant use of 1-hexene is the production of the linear aldehyde [[heptanal]] via [[hydroformylation]] ([[oxo synthesis]]).  Heptanal can be converted to the short-chain [[fatty acid]] [[heptanoic acid]] or the alcohol heptanol.

The chemical is used in the synthesis of flavors, perfumes, dyes and resins.

==Hazards==
1-Hexene is considered dangerous because in liquid and vapor form it is highly flammable and may be fatal if swallowed and enters airways.

The widespread use of 1-hexene may result in its release to the environment through various waste streams. The substance is toxic to aquatic organisms.<ref>{{cite web |title=1-Hexene |url=https://pubchem.ncbi.nlm.nih.gov/compound/1-hexene |website=PubChem |publisher=National Institutes of Health |access-date=21 January 2019}}</ref>

==References==
{{Reflist}}

==External links==
*[http://ull.chemistry.uakron.edu/erd/chemicals/1000/71.html Chemical Database, 1-Hexene]{{Dead link|date=August 2018 |bot=InternetArchiveBot |fix-attempted=yes }}

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[[Category:Alkenes]]