| Revision as of 16:40, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 467149256 of page 1-Hexene for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 01:19, 28 October 2024 edit Groogle (talk | contribs)Extended confirmed users2,027 editsm Phrasing |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 457305280 |
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| verifiedrevid = 477207844 |
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| Name = 1-Hexene |
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| Name = 1-Hexene |
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| ImageFile = 1-Hexene.PNG |
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| ImageFile = 1-hexene.svg |
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| ImageSize = |
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| ImageSize = |
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| ImageName = 1-Hexene |
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| ImageName = 1-Hexene |
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| ImageFile1 = 1-Hexene-3D-balls.png |
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| IUPACName = Hex-1-ene |
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| OtherNames = Hexene, Hexylene, butyl ethylene |
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| ImageAlt1 = 1-Hexene molecule |
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| PIN = Hex-1-ene |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = Hexene, Hexylene, Butyl ethylene |
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|Section1={{Chembox Identifiers |
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| SMILES = C=CCCCC |
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| SMILES = C=CCCCC |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 11109 |
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| ChemSpiderID = 11109 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 24579 |
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| PubChem = 11597 |
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| EINECS = 209-753-1 |
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| RTECS = MP6670000 |
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| UNNumber = 2370 |
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| UNII = B38ZZ8C206 |
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| ChEMBL = 1548726 |
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| InChI = 1/C6H12/c1-3-5-6-4-2/h3H,1,4-6H2,2H3 |
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| InChI = 1/C6H12/c1-3-5-6-4-2/h3H,1,4-6H2,2H3 |
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| InChIKey = LIKMAJRDDDTEIG-UHFFFAOYAY |
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| InChIKey = LIKMAJRDDDTEIG-UHFFFAOYAY |
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| SMILES1 = CCCCC=C |
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| SMILES1 = CCCCC=C |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H12/c1-3-5-6-4-2/h3H,1,4-6H2,2H3 |
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| StdInChI = 1S/C6H12/c1-3-5-6-4-2/h3H,1,4-6H2,2H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LIKMAJRDDDTEIG-UHFFFAOYSA-N |
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| StdInChIKey = LIKMAJRDDDTEIG-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 592-41-6 |
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| CASNo = 592-41-6 |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=6|H=12 |
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| Formula = C<sub>6</sub>H<sub>12 |
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| Appearance = Colorless liquid |
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| MolarMass = 84.1608 g/mol |
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| Density = 0.673 g/cm<sup>3</sup> |
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| Appearance = Colorless liquid |
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| Solubility = Insoluble |
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| Density = 0.673 g/cm<sup>3</sup>, liquid |
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| MeltingPtC = −139.8 |
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| Solubility = insoluble |
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| MeltingPt_notes = |
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| MeltingPt = −139.8 °C, 133.4 K, -219.64 °F |
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| BoilingPtC = 63 |
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| BoilingPtC = 63 |
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| Viscosity = 0.51 ] (0.51 mPa·s) at 28°C |
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| Viscosity = 0.51 ] (0.51 mPa·s) at 28°C |
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| Section3 = {{Chembox Structure |
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|Section3={{Chembox Structure |
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| Dipole = |
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| Dipole = |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}} |
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| EUClass = Highly flammable ('''F+'''); Harmful ('''XN''') |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|225|304|319}} |
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| 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}} |
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'''1-Hexene''' ('''hex-1-ene''') is an ] with the formula C<sub>6</sub>H<sub>12</sub>. It is an ] that is classified in industry as higher ] and an ], 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 ]. It is a colourless liquid. |
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==Production== |
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1-Hexene is commonly manufactured by two general routes: (i) full-range processes via the ] of ] and (ii) on-purpose technology. A minor route to 1-hexene, used commercially on smaller scales, is the ] of ]. Prior to the 1970s, 1-hexene was also manufactured by the thermal cracking of waxes. Linear internal hexenes were manufactured by ]/] of ].<ref> Lappin, George (Editor), Alpha Olefins Applications Handbook, Marcel Dekker Inc., {{ISBN|978-0-8247-7895-8}}</ref> |
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"Ethylene ]" 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 ] (SHOP) employs this approach. ] and ] 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 ] processes. |
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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) {{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 ] process is also considered an on-purpose route to 1-hexene. Sasol commercially employs ] synthesis to make fuels from ] 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 ], linear and branched internal olefins, linear and branched paraffins, ]s, ]s, ]s, and ]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. |
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{{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> |
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==Applications== |
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The primary use of 1-hexene is as a ] in production of ]. ] (HDPE) and ] (LLDPE) use approximately 2–4% and 8–10% of comonomers, respectively. |
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Another significant use of 1-hexene is the production of the linear aldehyde ] via ] (]). Heptanal can be converted to the short-chain ] ] or the alcohol heptanol. |
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The chemical is used in the synthesis of flavors, perfumes, dyes and resins. |
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==Hazards== |
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1-Hexene is considered dangerous because in liquid and vapor form it is highly flammable and may be fatal if swallowed and enters airways. |
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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> |
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==References== |
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{{Reflist}} |
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==External links== |
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*{{Dead link|date=August 2018 |bot=InternetArchiveBot |fix-attempted=yes }} |
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{{Authority control}} |
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{{Hydrides by group}} |
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{{DEFAULTSORT:Hexene, 1-}} |
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] |