1-Hexene: Difference between revisions

1-Hexene
Names
	Preferred IUPAC name Hex-1-ene
	Other names Hexene, Hexylene, Butyl ethylene
Identifiers
CAS Number	592-41-6 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:24579 ;
ChEMBL	ChEMBL1548726;
ChemSpider	11109 ;
ECHA InfoCard	100.008.868
EC Number	209-753-1;
PubChem CID	11597;
RTECS number	MP6670000;
UNII	B38ZZ8C206;
UN number	2370
CompTox Dashboard (EPA)	DTXSID4025402 ;
	InChI InChI=1S/C6H12/c1-3-5-6-4-2/h3H,1,4-6H2,2H3 Key: LIKMAJRDDDTEIG-UHFFFAOYSA-N ; InChI=1/C6H12/c1-3-5-6-4-2/h3H,1,4-6H2,2H3 Key: LIKMAJRDDDTEIG-UHFFFAOYAY;
	SMILES C=CCCCC; CCCCC=C;
Properties
Chemical formula	C6H12
Molar mass	84.162 g·mol−1
Appearance	Colorless liquid
Density	0.673 g/cm3
Melting point	−139.8 °C (−219.6 °F; 133.3 K)
Boiling point	63 °C (145 °F; 336 K)
Solubility in water	Insoluble
Viscosity	0.51 cP (0.51 mPa·s) at 28°C
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H225, H304, H319
Precautionary statements	P210, P233, P240, P241, P242, P243, P264, P280, P301+P310, P303+P361+P353, P305+P351+P338, P331, P337+P313, P370+P378, P403+P235, P405, P501
Safety data sheet (SDS)	External MSDS
Supplementary data page
	1-Hexene (data page)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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1-Hexene (hex-1-ene) is an organic compound with the formula C₆H₁₂. 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. 1-Hexene 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 of hexanol. Prior to the 1970s, 1-hexene was also manufactured by the thermal cracking of waxes. Linear internal hexenes were manufactured by chlorination/dehydrochlorination of linear paraffins.^[1]

"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. 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.^[2] 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, alcohols, aldehydes, carboxylic acids, and aromatic compounds. The trimerization of ethylene by homogeneous catalysts has been demonstrated.^[3] An alternative on-purpose route has been reported by Lummus Technology.^[4]

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.^[5]

References

^ Lappin, George (Editor), Alpha Olefins Applications Handbook, Marcel Dekker Inc., ISBN 978-0-8247-7895-8
^ (18 October 2010) Chevron Phillips Chemical announces plans for world-scale 1-hexene plant Archived 2014-11-29 at the Wayback Machine Plastinfo, Plastics Industry Directory, Retrieved 30 September 2011
^ 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.
^ "To make better decisions, you need to see the big picture".
^ "1-Hexene". PubChem. National Institutes of Health. Retrieved 21 January 2019.

External links

Chemical Database, 1-Hexene^{[permanent dead link]}

[1] Lappin, George (Editor), Alpha Olefins Applications Handbook, Marcel Dekker Inc., ISBN 978-0-8247-7895-8

[2] (18 October 2010) Chevron Phillips Chemical announces plans for world-scale 1-hexene plant Archived 2014-11-29 at the Wayback Machine Plastinfo, Plastics Industry Directory, Retrieved 30 September 2011

[3] 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.

[4] "To make better decisions, you need to see the big picture".

[5] "1-Hexene". PubChem. National Institutes of Health. Retrieved 21 January 2019.

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@@ Line 1: / Line 1: @@
 {{Chembox
+| Verifiedfields = changed
+| Watchedfields = changed
 | verifiedrevid = 477207844
 | Name = 1-Hexene
-| ImageFile = 1-Hexene.PNG
+| ImageFile = 1-hexene.svg
 | ImageSize =
 | ImageName = 1-Hexene
+| ImageFile1 = 1-Hexene-3D-balls.png
-| IUPACName = Hex-1-ene
-| OtherNames = Hexene, Hexylene, butyl ethylene
+| ImageAlt1 = 1-Hexene molecule
+| PIN = Hex-1-ene
-| Section1 = {{Chembox Identifiers
+| 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
@@ Line 21: / Line 33: @@
 | CASNo = 592-41-6
   }}
-| Section2 = {{Chembox Properties
+|Section2={{Chembox Properties
+| C=6|H=12
-|   Formula = C<sub>6</sub>H<sub>12
+| Appearance = Colorless liquid
-|   MolarMass = 84.1608 g/mol
+| Density = 0.673 g/cm<sup>3</sup>
-|   Appearance = Colorless liquid
+| Solubility = Insoluble
-|   Density = 0.673 g/cm<sup>3</sup>, liquid
+| MeltingPtC = −139.8
-|   Solubility = insoluble
+| MeltingPt_notes =
-|   MeltingPt = −139.8 °C, 133.4 K, -219.64 °F
-|   BoilingPtC = 63
+| BoilingPtC = 63
-|   Viscosity = 0.51 [[Poise|cP]] (0.51 mPa·s) at 28°C
+| Viscosity = 0.51 [[Poise (unit)|cP]] (0.51 mPa·s) at 28°C
   }}
-| Section3 = {{Chembox Structure
+|Section3={{Chembox Structure
-|   Dipole =
+| Dipole =
   }}
-| Section7 = {{Chembox Hazards
+|Section7={{Chembox Hazards
-|   ExternalMSDS =[http://ptcl.chem.ox.ac.uk/MSDS/HE/1-hexene.html External MSDS]
+| ExternalSDS =[http://hazard.com/msds/mf/baker/baker/files/h2740.htm External MSDS]
+| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}
-|   EUClass = Highly flammable ('''F+'''); Harmful ('''XN''')
+| 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''' 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]].  1-Hexene is a colourless liquid.
+'''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]].  1-Hexene is a colourless liquid.
 ==Production==
--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 [[chlorination]]/[[dehydrochlorination]] of linear paraffins.<ref> Lappin, George (Editor), Alpha Olefins Applications Handbook, Marcel Dekker Inc., ISBN 9780824778958</ref>
+-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. [[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.
+"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] 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, [[alcohols]], [[aldehydes]], [[carboxylic acids]], and [[aromatic compounds]].  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.
+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>
-{{DOI|10.1021/ja034752f}}.</ref>
-Lummus Technology has recently developed a new on purpose route where [[1-butene]] reacts with itself (“autometathesis” or “self-disproportionation”) to produce 1-hexene. A semi-commercial unit has been in operation in [[Tianjin, China]] to demonstrate the Lummus technology.
 ==Applications==
-The primary use of 1-hexene is as a [[comonomer]] in production of [[polyethene]]. [[High-density polyethene]] (HDPE) and [[linear low-density polyethene]] (LLDPE) use approximately 2–4% and 8–10% of comonomers, respectfully.
+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==
+-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}}
-<references />
 ==External links==
-*[http://ull.chemistry.uakron.edu/erd/chemicals/1000/71.html Chemical Database, 1-Hexene]
+*[http://ull.chemistry.uakron.edu/erd/chemicals/1000/71.html Chemical Database, 1-Hexene]{{Dead link|date=August 2018 |bot=InternetArchiveBot |fix-attempted=yes }}
+{{Authority control}}
+{{Hydrides by group}}
 {{DEFAULTSORT:Hexene, 1-}}
 [[Category:Alkenes]]
-[[da:1-Hexen]]
-[[de:1-Hexen]]
-[[fr:Hex-1-ène]]
-[[nl:1-hexeen]]
-[[ja:1-ヘキセン]]