Ethylene

Source: Wikipedia, the free encyclopedia.
(Redirected from
Ethene
)
"Ethene" redirects here. Not to be confused with
ethyne
.
Ethylene
Names
IUPAC name
Ethene
Preferred IUPAC name
Ethene[1]
Other names
R-1150
Identifiers
3D model (
JSmol
)
1730731
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.000.742 Edit this at Wikidata
EC Number
  • 200-815-3
214
KEGG
RTECS number
  • KU5340000
UNII
UN number 1962 1038
  • InChI=1S/C2H4/c1-2/h1-2H2 checkY
    Key: VGGSQFUCUMXWEO-UHFFFAOYSA-N checkY
  • InChI=1/C2H4/c1-2/h1-2H2
    Key: VGGSQFUCUMXWEO-UHFFFAOYAE
  • C=C
Properties
C
2H
4
Molar mass 28.054 g·mol−1
Appearance colourless gas
Density 1.178 kg/m3 at 15 °C, gas[2]
Melting point −169.2 °C (−272.6 °F; 104.0 K)
Boiling point −103.7 °C (−154.7 °F; 169.5 K)
0.131 mg/mL (25 °C);[citation needed] 2.9 mg/L[3]
Solubility in ethanol 4.22 mg/L[3]
Solubility in diethyl ether good[3]
Acidity (pKa) 44
Conjugate acid
 Ethenium
-15.30·10−6 cm3/mol
Viscosity 10.28 μPa·s[4]
Structure
D2h
zero
Thermochemistry
219.32 J·K−1·mol−1
Std enthalpy of
formation
(ΔfH⦵298)
 +52.47 kJ/mol
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Danger
H220, H336
P210, P261, P271, P304+P340, P312, P377, P381, P403, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
2
4
2
Flash point −136 °C (−213 °F; 137 K)
542.8 °C (1,009.0 °F; 815.9 K)
Safety data sheet (SDS) ICSC 0475
Related compounds
Related compounds
Propene
Supplementary data page
Ethylene (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Ethylene (

flammable gas with a faint "sweet and musky" odour when pure.[6] It is the simplest alkene (a hydrocarbon with carbon–carbon double bonds
).

Ethylene is widely used in the chemical industry, and its worldwide production (over 150 million

feedstock production and carbon dioxide from any non-sustainable energy
used.

Ethylene is also an important natural plant hormone and is used in agriculture to induce ripening of fruits.[10] The hydrate of ethylene is ethanol.

Structure and properties

Orbital description of bonding between ethylene and a transition metal

This

hybridized carbon. The molecule is also relatively weak: rotation about the C-C bond is a very low energy process that requires breaking the π-bond by supplying heat at 50 °C.[citation needed
]

The

electrophiles. Many reactions of ethylene are catalyzed by transition metals, which bind transiently to the ethylene using both the π and π* orbitals.[citation needed
]

Being a simple molecule, ethylene is spectroscopically simple. Its UV-vis spectrum is still used as a test of theoretical methods.[11]

Uses

Diagram of uses of ethene

Major industrial reactions of ethylene include in order of scale: 1)

ethylene dichloride, ethylbenzene and polyethylene.[12] Most of the reactions with ethylene are electrophilic addition.[citation needed
]

ethylene dichloride, precursor to vinyl chloride
.

Polymerization

See also: Ziegler–Natta catalyst and Polyethylene

Polyethylene production uses more than half of the world's ethylene supply. Polyethylene, also called polyethene and polythene, is the world's most widely used plastic. It is primarily used to make films in

synthetic lubricants, additives, and also as co-monomers in the production of polyethylenes.[12]

Oxidation

Ethylene is

oxidized to produce ethylene oxide, a key raw material in the production of surfactants and detergents by ethoxylation. Ethylene oxide is also hydrolyzed to produce ethylene glycol, widely used as an automotive antifreeze as well as higher molecular weight glycols, glycol ethers, and polyethylene terephthalate.[13][14]

Main article: Wacker process

Ethylene oxidation in the presence of a palladium catalyst can form acetaldehyde. This conversion remains a major industrial process (10M kg/y).[15] The process proceeds via the initial complexation of ethylene to a Pd(II) center.[citation needed]

Halogenation and hydrohalogenation

Major intermediates from the

ethyl bromide.[16]

Alkylation

Major chemical intermediates from the alkylation with ethylene is ethylbenzene, precursor to styrene. Styrene is used principally in polystyrene for packaging and insulation, as well as in styrene-butadiene rubber for tires and footwear. On a smaller scale, ethyltoluene, ethylanilines, 1,4-hexadiene, and aluminium alkyls. Products of these intermediates include polystyrene, unsaturated polyesters and ethylene-propylene terpolymers.[16]

Oxo reaction

The

n-propyl alcohol.[16]

Hydration

Ethylene has long represented the major nonfermentative precursor to

solid acid catalysts:[17]

C2H4 + H2O → CH3CH2OH

Dimerization to butenes

Ethylene is

1-butene. 1-Butene is used as a comonomer in the production of certain kinds of polyethylene.[18]

Fruit and flowering

Main article:
Ethylene as a plant hormone

Ethylene is a hormone that affects the ripening and flowering of many plants. It is widely used to control freshness in horticulture and fruits.[19] The scrubbing of naturally occurring ethylene delays ripening.[20]

Niche uses

An example of a niche use is as an anesthetic agent (in an 85% ethylene/15% oxygen ratio).[21] Another use is as a welding gas.[12][22] It is also used as a refrigerant gas for low temperature applications under the name R-1150.[23]

Production

Global ethylene production was 107 million tonnes in 2005,

Mideast and in China.[26] Production emits greenhouse gas, namely significant amounts of carbon dioxide.[27]

Industrial process

Ethylene is produced by several methods in the

methanol-to-olefins (MTO).[29]

Laboratory synthesis

Although of great value industrially, ethylene is rarely synthesized in the laboratory and is ordinarily purchased.[30] It can be produced via dehydration of ethanol with sulfuric acid or in the gas phase with aluminium oxide or activated alumina.[31]

Biosynthesis

Ethylene is produced from methionine in nature. The immediate precursor is 1-aminocyclopropane-1-carboxylic acid.[32]

Ligand

Chlorobis(ethylene)rhodium dimer is a well-studied complex of ethylene.[33]

Ethylene is a fundamental

transition metal alkene complexes. One of the first organometallic compounds, Zeise's salt is a complex of ethylene. Useful reagents containing ethylene include Pt(PPh3)2(C2H4) and Rh2Cl2(C2H4)4. The Rh-catalysed hydroformylation of ethylene is conducted on an industrial scale to provide propionaldehyde.[34]

History

Some geologists and scholars believe that the famous Greek Oracle at Delphi (the Pythia) went into her trance-like state as an effect of ethylene rising from ground faults.[35]

Ethylene appears to have been discovered by Johann Joachim Becher, who obtained it by heating ethanol with sulfuric acid;[36] he mentioned the gas in his Physica Subterranea (1669).[37] Joseph Priestley also mentions the gas in his Experiments and observations relating to the various branches of natural philosophy: with a continuation of the observations on air (1779), where he reports that Jan Ingenhousz saw ethylene synthesized in the same way by a Mr. Enée in Amsterdam in 1777 and that Ingenhousz subsequently produced the gas himself.[38] The properties of ethylene were studied in 1795 by four Dutch chemists, Johann Rudolph Deimann, Adrien Paets van Troostwyck, Anthoni Lauwerenburgh and Nicolas Bondt, who found that it differed from hydrogen gas and that it contained both carbon and hydrogen.[39] This group also discovered that ethylene could be combined with chlorine to produce the Dutch oil, 1,2-dichloroethane; this discovery gave ethylene the name used for it at that time, olefiant gas (oil-making gas.)[40] The term olefiant gas is in turn the etymological origin of the modern word "olefin", the class of hydrocarbons in which ethylene is the first member.[citation needed]

In the mid-19th century, the suffix -ene (an Ancient Greek root added to the end of female names meaning "daughter of") was widely used to refer to a molecule or part thereof that contained one fewer hydrogen atoms than the molecule being modified. Thus, ethylene (C
2H
4) was the "daughter of ethyl" (C
2H
5). The name ethylene was used in this sense as early as 1852.[41]

In 1866, the

IUPAC
nomenclature. However, by that time, the name ethylene was deeply entrenched, and it remains in wide use today, especially in the chemical industry.

Following experimentation by Luckhardt, Crocker, and Carter at the University of Chicago,[43] ethylene was used as an anesthetic.[44][6] It remained in use through the 1940s use even while chloroform was being phased out. Its pungent odor and its explosive nature limit its use today.[45]

Nomenclature

The 1979 IUPAC nomenclature rules made an exception for retaining the non-systematic name ethylene;

divalent group -CH2CH2-. Hence, names like ethylene oxide and ethylene dibromide are permitted, but the use of the name ethylene for the two-carbon alkene is not. Nevertheless, use of the name ethylene for H2C=CH2 (and propylene for H2C=CHCH3) is still prevalent among chemists in North America.[49]

Greenhouse gas emissions

“A key factor affecting petrochemicals life-cycle emissions is the methane intensity of feedstocks, especially in the production segment.”[50] Emissions from cracking of naptha and natural gas(common in the US as gas is cheap there) depend a lot on the source of energy (for example gas burnt to provide high temperatures[51]) but that from naptha is certainly more per kg of feedstock.[52] Both steam cracking and production from natural gas via ethane are estimated to emit 1.8 to 2kg of CO2 per kg ethylene produced,[53] totalling over 260 million tonnes a year.[54] This is more than all other manufactured chemicals except cement and ammonia.[55] According to a 2022 report using renewable or nuclear energy could cut emissions by almost half.[52]

Safety

Like all hydrocarbons, ethylene is a combustible

class 3 carcinogen, since there is no current evidence that it causes cancer in humans.[56]

See also

  • RediRipe, an ethylene detector for fruits.

References

  1. ^ "Ethylene". Archived from the original on 2023-10-08. Retrieved 2021-05-27.
  2. ^ Record of Ethylene in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 25 October 2007.
  3. ^ a b c Neiland, O. Ya. (1990) Органическая химия: Учебник для хим. спец. вузов. Moscow. Vysshaya Shkola. p. 128.
  4. doi:10.1063/1.434048
    .
  5. ^ ETHYLENE | CAMEO Chemicals | NOAA Archived 2015-04-02 at the Wayback Machine. Cameochemicals.noaa.gov. Retrieved on 2016-04-24.
  6. ^
    ISBN 978-3527306732
    .
  7. ^ Research and Markets. "The Ethylene Technology Report 2016 - Research and Markets". www.researchandmarkets.com. Archived from the original on 10 May 2020. Retrieved 19 June 2016.
  8. ^
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    .
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    from the original on 2016-03-04. Retrieved 2012-09-17.
  10. PMID 12045274
    .
  11. ^ "Ethylene:UV/Visible Spectrum". NIST Webbook. Archived from the original on 2017-01-19. Retrieved 2006-09-27.
  12. ^ a b c "OECD SIDS Initial Assessment Profile — Ethylene" (PDF). inchem.org. Archived from the original (PDF) on 2015-09-24. Retrieved 2008-05-21.
  13. ^ "Ethylene Glycol: Systemic Agent". Center for Disease Control. 20 October 2021. Archived from the original on 26 December 2017. Retrieved 20 February 2022.
  14. ^ "Ethylene Glycol". Science Direct. Archived from the original on 2022-02-20. Retrieved 2022-02-20.
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    .
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    ISBN 978-0-8247-6914-7
    .
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    .
  18. ^ "1-Butene - Major Uses". WISER. Archived from the original on Nov 16, 2021. Retrieved 2021-11-16.
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  22. ^ "Informational Bulletin". Vol. 12. California Fresh Market Advisory Board. June 1, 1976.
  23. ^ "R-1150 ETHYLENE Safety Data Sheet" (PDF). Australian Refrigeration Mechanics Association. April 2015. Archived (PDF) from the original on 1 July 2023. Retrieved 1 July 2023.
  24. National Non-Food Crops Centre
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  27. S2CID 248838079
    .
  28. ^ "Ethylene Production and Manufacturing Process". Icis. Archived from the original on 2019-07-29. Retrieved 2019-07-29.
  29. doi:10.1016/J.ENG.2017.02.006
    .
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  35. ^ Roach J (2001-08-14). "Delphic Oracle's Lips May Have Been Loosened by Gas Vapors". National Geographic. Archived from the original on September 24, 2001. Retrieved March 8, 2007.
  36. ^ Roscoe HE, Schorlemmer C (1878). A treatise on chemistry. Vol. 1. D. Appleton. p. 611.
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  38. ^ Appendix, §VIII, pp. 474 ff., Experiments and observations relating to the various branches of natural philosophy: with a continuation of the observations on air, Joseph Priestley, London: printed for J. Johnson, 1779, vol. 1.
  39. ^ Roscoe & Schorlemmer 1878, p. 612
  40. ^ Roscoe & Schorlemmer 1878, p. 613
    Gregory W (1857). Handbook of organic chemistry (4th American ed.). A.S. Barnes & Co. p. 157.
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  47. ^ Footnote to IUPAC nomenclature rule R-9.1, table 19(b) Archived 2007-12-19 at the Wayback Machine. Acdlabs.com. Retrieved on 2016-04-24.
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    )
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