Hex-1-en là gì

1-Hexene

Hex-1-en là gì
Hex-1-en là gì
Names
Preferred IUPAC name

Hex-1-ene

Other names

Hexene, Hexylene, Butyl ethylene

Identifiers

CAS Number

  • 592-41-6 
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3D model (JSmol)

  • Interactive image
  • Interactive image

ChEBI

  • CHEBI:24579 
    Hex-1-en là gì

ChEMBL

  • ChEMBL1548726

ChemSpider

  • 11109 
    Hex-1-en là gì

ECHA InfoCard 100.008.868
Hex-1-en là gì
EC Number

  • 209-753-1

PubChem CID

  • 11597

RTECS number

  • MP6670000

UNII

  • B38ZZ8C206

UN number 2370

CompTox Dashboard (EPA)

  • DTXSID4025402
    Hex-1-en là gì

InChI

  • InChI=1S/C6H12/c1-3-5-6-4-2/h3H,1,4-6H2,2H3 

    Hex-1-en là gì

    Key: LIKMAJRDDDTEIG-UHFFFAOYSA-N 

    Hex-1-en là gì

  • 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

Hex-1-en là gì
Hex-1-en là gì
Hex-1-en là gì

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).

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Infobox references

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[edit]

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[edit]

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[edit]

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[edit]

  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.

  • Chemical Database, 1-Hexene[permanent dead link]