11/30/2016 Ethane ­ Wikipedia

Ethane
From Wikipedia, the free encyclopedia

Ethane (/ˈɛθeɪn/ or /ˈiːθeɪn/) is an organic chemical compound Ethane

with chemical formula C2H6. At standard temperature and
pressure, ethane is a colorless, odorless gas. Like many
hydrocarbons, ethane is isolated on an industrial scale from
natural gas and as a petrochemical byproduct of petroleum
refining. Its chief use is as feedstock for ethylene production.

Related compounds may be formed by replacing a hydrogen

atoms with another functional group; the ethane moiety is called
an ethyl group. For example, an ethyl group linked to a hydroxyl
group yields ethanol, the alcohol in beverages.
Names
Preferred IUPAC name
Ethane[1]
Contents
Systematic IUPAC name
1 History Dicarbane (never recommended[1])
2 Properties Identifiers
3 Chemistry
CAS Number 74­84­0 (http://www.commonc
3.1 Combustion
3.2 Ethane barrier hemistry.org/ChemicalDetail.as
4 Production px?ref=74­84­0)
5 Uses 3D model (Jmol) Interactive image (http://chema
6 Health and safety
pps.stolaf.edu/jmol/jmol.php?m
7 Atmospheric and extraterrestrial ethane
8 References odel=CC)
9 External links Beilstein Reference 1730716
ChEBI CHEBI:42266 (https://www.eb
i.ac.uk/chebi/searchId.do?chebi
History Id=42266)
ChEMBL ChEMBL135626 (https://www.
Ethane was first synthesised in 1834 by Michael Faraday,
ebi.ac.uk/chembldb/index.php/c
applying electrolysis of a potassium acetate solution. He
ompound/inspect/ChEMBL135
mistook the hydrocarbon product of this reaction for methane
and did not investigate it further.[5] During the period 1847– 626)
1849, in an effort to vindicate the radical theory of organic ChemSpider 6084 (http://www.chemspider.c
chemistry, Hermann Kolbe and Edward Frankland produced om/Chemical­Structure.6084.ht
ethane by the reductions of propionitrile (ethyl cyanide)[6] and ml)
ethyl iodide[7] with potassium metal, and, as did Faraday, by the ECHA InfoCard 100.000.741 (https://echa.europ
electrolysis of aqueous acetates. They, however, mistook the a.eu/substance­information/­/su
product of these reactions for methyl radical rather than the bstanceinfo/100.000.741)
dimer of methyl, ethane. This error was corrected in 1864 by
Carl Schorlemmer, who showed that the product of all these EC Number 200­814­8

reactions was in fact ethane.[8] Gmelin Reference 212

MeSH Ethane (https://www.nlm.nih.g
ov/cgi/mesh/2014/MB_cgi?mod

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The name ethane is derived from the IUPAC nomenclature of e=&term=Ethane)

organic chemistry. "Eth­" is derived from the German for PubChem 6324 (https://pubchem.ncbi.nl
potable alcohol (ethanol),[9] and "­ane" refers to the presence of m.nih.gov/compound/6324)
a single bond between the carbon atoms.
RTECS number KH3800000
UNII L99N5N533T (http://fdasis.nl
Properties m.nih.gov/srs/srsdirect.jsp?regn
o=L99N5N533T)
At standard temperature and pressure, ethane is a colorless,
odorless gas. It has a boiling point of ­88.5 °C and melting point UN number 1035
of ­182.8 °C. Solid ethane exists in several modifications.[10] On InChI
cooling under normal pressure the first modification to appear is SMILES
a plastic crystal, crystallizing in the cubic system. In this form,
Properties
the positions of the hydrogen atoms are not fixed; the molecules
may rotate freely around the long axis. Cooling this ethane Chemical formula C2H6
below ca. 89.9 K changes it to monoclinic metastable ethane II Molar mass 30.07 g·mol−1
(space group P 21/n).[11] Ethane is only very sparingly soluble in
Appearance Colorless gas
water.
Odor Odorless

Chemistry Density 1.3562 mg cm−3 (at

0 °C)[2]
Ethane can be viewed as two methyl groups joined, that is, a 0.5446 g cm−3
dimer of methyl groups. In the laboratory, ethane may be
conveniently synthesised by Kolbe electrolysis. In this (at 184 K)[3]
technique, an aqueous solution of an acetate salt is electrolysed. Melting point −182.8 °C; −296.9 °F; 90.4 K
At the anode, acetate is oxidized to produce carbon dioxide and Boiling point −88.5 °C; −127.4 °F; 184.6 K
methyl radicals, and the highly reactive methyl radicals combine Solubility in water
to produce ethane: 56.8 mg L−1[4]
Vapor pressure 3.8453 MPa (at 21.1 °C)
CH3COO− → CH3• + CO2 + e− Henry's law 19 nmol Pa−1 kg−1
CH3• + •CH3 → C2H6 constant (kH)
Acidity (pKa) 50
Synthesis by oxidation of acetic anhydride by peroxides, is
conceptually similar. Basicity (pKb) ­36
Thermochemistry
The chemistry of ethane involves chiefly free radical reactions.
Specific 52.49 J K−1 mol−1
Ethane can react with the halogens, especially chlorine and heat capacity (C)
bromine, by free radical halogenation. This reaction proceeds
Std enthalpy of −84 kJ mol−1
through the propagation of the ethyl radical: o
formation (ΔfH 298)
C2H5• + Cl2 → C2H5Cl + Cl• Std enthalpy of −1561.0–−1560.4 kJ mol−1
Cl• + C2H6 → C2H5• + HCl combustion
(ΔcHo298)
Because halogenated ethanes can undergo further free radical Hazards
halogenation, this process results in a mixture of several
Safety data sheet See: data page
halogenated products. In the chemical industry, more selective
chemical reactions are used for the production of any particular inchem.org (http://www.inche
two­carbon haloalkane. m.org/documents/icsc/icsc/eics0
266.htm)
Combustion GHS pictograms

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The complete combustion of ethane releases 1559.7 kJ/mol, or

51.9 kJ/g, of heat, and produces carbon dioxide and water
according to the chemical equation
GHS signal word DANGER
2 C2H6 + 7 O2 → 4 CO2 + 6 H2O + 3120 kJ GHS hazard H220, H280
statements
Combustion may also occur without an excess of oxygen, GHS precautionary P210, P410+403
forming a mix of amorphous carbon and carbon monoxide. statements
EU classification
2 C2H6 + 3 O2 → 4 C + 6 H2O + energy F+
(DSD)
2 C2H6 + 5 O2 → 4 CO + 6 H2O + energy
R­phrases R12
2 C2H6 + 4 O2 → 2 C + 2 CO + 6 H2O + energy etc.
S­phrases (S2), S9, S16, S33
Combustion occurs by a complex series of free­radical reactions. NFPA 704
Computer simulations of the chemical kinetics of ethane
4
combustion have included hundreds of reactions. An important
1 0
series of reaction in ethane combustion is the combination of an
ethyl radical with oxygen, and the subsequent breakup of the Flash point −135 °C (−211 °F; 138 K)
resulting peroxide into ethoxy and hydroxyl radicals.
Autoignition 472 °C (882 °F; 745 K)
temperature
C2H5• + O2 → C2H5OO•
Explosive limits 2.9–13%
C2H5OO• + HR → C2H5OOH + •R
C2H5OOH → C2H5O• + •OH Related compounds
Related alkanes Methane
The principal carbon­containing products of incomplete ethane Methyl iodide
combustion are single­carbon compounds such as carbon Diiodomethane
monoxide and formaldehyde. One important route by which the Iodoform
carbon­carbon bond in ethane is broken to yield these single­ Carbon tetraiodide
carbon products is the decomposition of the ethoxy radical into a Ethyl iodide
methyl radical and formaldehyde, which can in turn undergo
Propane
further oxidation.
n­Propyl iodide
C2H5O• → CH3• + CH2O Isopropyl iodide
Related compounds Pimagedine
Some minor products in the incomplete combustion of ethane Guanidine
include acetaldehyde, methane, methanol, and ethanol. At higher Diiodohydroxypropane
temperatures, especially in the range 600–900 °C, ethylene is a
significant product. It arises through reactions such as this: Supplementary data page
Structure and Refractive index (n),
C2H5• + O2 → C2H4 + •OOH properties Dielectric constant (εr), etc.
Thermodynamic Phase behaviour
Similar reactions (with agents other than oxygen as the data
hydrogen abstractor) are involved in the production of ethylene solid–liquid–gas
from ethane in steam cracking. Spectral data UV, IR, NMR, MS
Except where otherwise noted, data are given for
Ethane barrier materials in their standard state (at 25 °C [77 °F],
100 kPa).
Rotating a molecular substructure about a twistable bond usually verify (what is ?)
requires energy. The minimum energy to produce a 360­degree
Infobox references
bond rotation is called the rotational barrier.

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Ethane gives a classic, simple example of such a rotational barrier,

Ethane barrier to rotation about the
carbon­carbon bond. The curve is
potential energy as a function of
rotational angle.
sometimes called the "ethane barrier." Among the earliest experimental
evidence of this barrier (see diagram at left) was obtained by modelling the
entropy of ethane.[12] The three hydrogens at each end are free to pinwheel
about the central carbon­carbon bond when provided with sufficient energy
to overcome the barrier. The physical origin of the barrier is still not
completely settled,[13] although the overlap (exchange) repulsion[14]
between the hydrogen atoms on opposing ends of the molecule is perhaps
the strongest candidate, with the stabilizing effect of hyperconjugation on
the staggered conformation contributing to the phenomenon.[15] However,
theoretical methods that use an appropriate starting point (orthogonal
orbitals) find that hyperconjugation is the most important factor in the
origin of the ethane rotation barrier.[16]

As far back as 1890–1891, chemists suggested that ethane molecules

preferred the staggered conformation with the two ends of the molecule askew from each other.[17][18][19]

Production
After methane, ethane is the second­largest component of natural gas. Natural gas from different gas fields varies
in ethane content from less than 1% to more than 6% by volume. Prior to the 1960s, ethane and larger molecules
were typically not separated from the methane component of natural gas, but simply burnt along with the methane
as a fuel. Today, ethane is an important petrochemical feedstock and is separated from the other components of
natural gas in most well­developed gas fields. Ethane can also be separated from petroleum gas, a mixture of
gaseous hydrocarbons produced as a byproduct of petroleum refining. Economics of building and running
processing plants can change, however. If the relative value of sending the unprocessed natural gas to a consumer
exceeds the value of extracting ethane, ethane extraction might not be run, which could cause operational issues
managing the changing quality of the gas in downstream systems.

Ethane is most efficiently separated from methane by liquefying it at cryogenic temperatures. Various refrigeration
strategies exist: the most economical process presently in wide use employs a Turboexpander, and can recover
more than 90% of the ethane in natural gas. In this process, chilled gas is expanded through a turbine, reducing the
temperature to about −100 °C. At this low temperature, gaseous methane can be separated from the liquefied
ethane and heavier hydrocarbons by distillation. Further distillation then separates ethane from the propane and
heavier hydrocarbons.

Uses
The chief use of ethane is the production of ethene (ethylene) by steam cracking. When diluted with steam and
briefly heated to very high temperatures (900 °C or more), heavy hydrocarbons break down into lighter
hydrocarbons, and saturated hydrocarbons become unsaturated. Ethane is favored for ethene production because
the steam cracking of ethane is fairly selective for ethene, while the steam cracking of heavier hydrocarbons yields
a product mixture poorer in ethene and richer in heavier alkenes (olefins), such as propene (propylene) and
butadiene, and in aromatic hydrocarbons.

Experimentally, ethane is under investigation as a feedstock for other commodity chemicals. Oxidative
chlorination of ethane has long appeared to be a potentially more economical route to vinyl chloride than ethene
chlorination. Many processes for producing this reaction have been patented, but poor selectivity for vinyl chloride

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and corrosive reaction conditions (specifically, a reaction mixture containing hydrochloric acid at temperatures
greater than 500 °C) have discouraged the commercialization of most of them. Presently, INEOS operates a 1000
t/a (tonnes per annum) ethane­to­vinyl chloride pilot plant at Wilhelmshaven in Germany.

Similarly, the Saudi Arabian firm SABIC has announced construction of a 30,000 tonnes per annum plant to
produce acetic acid by ethane oxidation at Yanbu. The economic viability of this process may rely on the low cost
of ethane near Saudi oil fields, and it may not be competitive with methanol carbonylation elsewhere in the world.

Ethane can be used as a refrigerant in cryogenic refrigeration systems. On a much smaller scale, in scientific
research, liquid ethane is used to vitrify water­rich samples for electron microscopy (cryo­electron microscopy). A
thin film of water, quickly immersed in liquid ethane at −150 °C or colder, freezes too quickly for water to
crystallize. With slower freezing methods, ice crystals can disrupt soft structures, damaging the samples.

Health and safety

At room temperature, ethane is a flammable gas. When mixed with air at 3.0%–12.5% by volume, it forms an
explosive mixture.

Some additional precautions are necessary where ethane is stored as a cryogenic liquid. Direct contact with liquid
ethane can result in severe frostbite. Until they warm to room temperature, the vapors from liquid ethane are
heavier than air and can flow along the floor or ground, gathering in low places; if the vapors encounter an ignition
source, the chemical reaction can flash back to the source of ethane from which they evaporated.

Containers recently emptied of ethane may contain insufficient oxygen to support life. Beyond this asphyxiation
hazard, ethane poses no known acute or chronic toxicological risk. It is not a carcinogen.[20]

Atmospheric and extraterrestrial ethane

Ethane occurs as a trace gas in the Earth's atmosphere, currently
having a concentration at sea level of 0.5 ppb,[21] though its pre­
Industrial concentration is likely to have been lower since a significant
proportion of the ethane in today's atmosphere may have originated as
fossil fuels. Global ethane quantities have varied over time, likely due
to flaring at natural gas fields.[22] Global ethane emission rates
declined from 1984 to 2010,[22] though increased shale gas production
at the Bakken Formation in the U.S. has arrested the decline by
half.[23] [24]
A photograph of Titan's northern latitudes.
Although ethane is a greenhouse gas, it is much less abundant than
The dark features appear to be
methane and also less efficient relative to mass. It has been detected as
hydrocarbon lakes, but further images will
a trace component in the atmospheres of all four giant planets, and in
be needed to see if the dark spots remain
the atmosphere of Saturn's moon Titan.[25] the same (as they would if they were lakes)

Atmospheric ethane results from the Sun's photochemical action on

methane gas, also present in these atmospheres: ultraviolet photons of shorter wavelengths than 160 nm can photo­
dissociate the methane molecule into a methyl radical and a hydrogen atom. When two methyl radicals recombine,
the result is ethane:

CH4 → CH3• + •H

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CH3• + •CH3 → C2H6

It was once widely hypothesized that ethane produced in this fashion on Titan rained back onto the moon's surface,
and over time had accumulated into hydrocarbon seas or oceans covering much of the moon's surface. Infrared
telescopic observations cast significant doubt on this hypothesis, and the Huygens probe, which landed on Titan in
2005, failed to observe any surface liquids, although it did photograph features that could be presently dry drainage
channels. In December 2007 the Cassini probe found at least one lake at Titan's south pole, now called Ontario
Lacus because of the lake's similar area to Lake Ontario on Earth (approximately 20,000 km2). Further analysis of
infrared spectroscopic data presented in July 2008[26] provided stronger evidence for the presence of liquid ethane
in Ontario Lacus.

In 1996, ethane was detected in Comet Hyakutake,[27] and it has since been detected in some other comets. The
existence of ethane in these distant solar system bodies may implicate ethane as a primordial component of the
solar nebula from which the sun and planets are believed to have formed.

In 2006, Dale Cruikshank of NASA/Ames Research Center (a New Horizons co­investigator) and his colleagues
announced the spectroscopic discovery of ethane on Pluto's surface.[28]

References
1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge:
The Royal Society of Chemistry. 2014. p. 4. doi:10.1039/9781849733069­FP001. ISBN 978­0­85404­182­4. "Similarly,
the retained names ‘ethane’, ‘propane’, and ‘butane’ were never replaced by systematic names ‘dicarbane’, ‘tricarbane’,
and ‘tetracarbane’ as recommended for analogues of silane, ‘disilane’; phosphane, ‘triphosphane’; and sulfane,
‘tetrasulfane’."
2. "Ethane – Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16
September 2004. Retrieved 7 December 2011.
3. Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. p. 3.22.
ISBN 0­8493­0486­5.
4. Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. p. 8.88.
ISBN 0­8493­0486­5.
5. Faraday, Michael (1834). "Experimental researches in electricity: Seventh series". Philosophical Transactions. 124: 77–
122. doi:10.1098/rstl.1834.0008.
6. Kolbe, Hermann; Frankland, Edward (1849). "On the products of the action of potassium on cyanide of ethyl". Journal of
the Chemical Society. 1: 60–74. doi:10.1039/QJ8490100060.
7. Frankland, Edward (1850). "On the isolation of the organic radicals". Journal of the Chemical Society. 2 (3): 263–296.
doi:10.1039/QJ8500200263.
8. Schorlemmer, Carl (1864). Annalen der Chemie. 132: 234. Missing or empty |title= (help)
9. "the definition of ethyl". Dictionary.com. Retrieved 2016­03­12.
10. GJH van Nes & A Vos (1978): Single­Crystal Structures and Electron Density Distributions of Ethane, Ethylene and
Acetylene. I. Single­Crystal X­ray Structure Determinations of Two Modifications of Ethane. Acta Crystallogr, Sect. B,
vol 34, pp. 1947ff.
11. see ethane as a solid on http://www.paarpraxis­rheinmain.de/W/kristallgitter/kristallgitter.htm (http://www.paarpraxis­rhei
nmain.de/W/kristallgitter/kristallgitter.htm)
12. Kemp, J. D. and Pitzer, K. S., J. Am. Chem. Soc., 1937, 59, 276­279
13. Ercolani, G. (2005). "Determination of the Rotational Barrier in Ethane by Vibrational Spectroscopy and Statistical
Thermodynamics". J. Chem. Educ. 82 (11): 1703–1708. Bibcode:2005JChEd..82.1703E. doi:10.1021/ed082p1703.
14. Pitzer, R. M. (1983). "The Barrier to Internal Rotation in Ethane". Acc. Chem. Res. 16 (6): 207–210.
doi:10.1021/ar00090a004.
15. Mo, Y.; Wu, W.; Song, L.; Lin, M.; Zhang, Q.; Gao, J. (2004). "The Magnitude of Hyperconjugation in Ethane: A
Perspective from Ab Initio Valence Bond Theory". Angew. Chem. Int. Ed. 43 (15): 1986–1990.
doi:10.1002/anie.200352931.

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16. Pophristic, V.; Goodman, L. (2001) Hyperconjugation not steric repulsion leads to the staggered structure of ethane.
Nature, 411, 565­568. Schreiner, P. R. (2002) Teaching the Right Reasons: Lessons from the Mistaken Origin of the
Rotational Barrier in Ethane. Angewandte Chemie International Edition, 41, 3579­3581.
17. Bischoff, CA, (1890), Chem. Ber. 23, 623
18. Bischoff, CA, (1891a), Chem. Ber. 24, 1074, 1086
19. Bischoff, CA, (1891b), Chem. Ber. 26, 1452
20. Daniel Vallero (June 7, 2010). Environmental Biotechnology: A Biosystems Approach. Academic Press. p. 641.
21. Trace gases (http://www.atmosphere.mpg.de/enid/3tg.html). Atmosphere.mpg.de. Retrieved on 2011­12­08.
22. Simpson, Isobel J.; Sulbaek Andersen, Mads P.; Meinardi, Simone; Bruhwiler, Lori; Blake, Nicola J.; Helmig, Detlev;
Rowland, F. Sherwood; Blake, Donald R. (2012). "Long­term decline of global atmospheric ethane concentrations and
implications for methane". Nature. 488 (7412): 490–494. doi:10.1038/nature11342. ISSN 0028­0836.
23. Kort, E. A.; Smith, M. L.; Murray, L. T.; Gvakharia, A.; Brandt, A. R.; Peischl, J.; Ryerson, T. B.; Sweeney, C.; Travis,
K. (2016). "Fugitive emissions from the Bakken shale illustrate role of shale production in global ethane shift".
Geophysical Research Letters. doi:10.1002/2016GL068703. ISSN 0094­8276.
24. "One oil field a key culprit in global ethane gas increase".
25. Brown, Bob; et al. (2008). "NASA Confirms Liquid Lake on Saturn Moon".
26. Brown, R. H.; Soderblom, L. A.; Soderblom, J. M.; Clark, R. N.; Jaumann, R.; Barnes, J. W.; Sotin, C.; Buratti, B.; et
al. (2008). "The identification of liquid ethane in Titan's Ontario Lacus". Nature. 454 (7204): 607–10.
Bibcode:2008Natur.454..607B. doi:10.1038/nature07100. PMID 18668101.
27. Mumma, Michael J.; et al. (1996). "Detection of Abundant Ethane and Methane, Along with Carbon Monoxide and
Water, in Comet C/1996 B2 Hyakutake: Evidence for Interstellar Origin". Science. 272 (5266): 1310–1314.
Bibcode:1996Sci...272.1310M. doi:10.1126/science.272.5266.1310. PMID 8650540.
28. A. Stern (November 1, 2006). "Making Old Horizons New". The PI's Perspective. Johns Hopkins University Applied
Physics Laboratory. Retrieved 2007­02­12.

External links
International Chemical Safety Card 0266 (http://www.inchem.org/do
cuments/icsc/icsc/eics0266.htm) Wikimedia Commons has
media related to Ethane.
Market­Driven Evolution of Gas Processing Technologies for NGLs
(http://www.aet.com/gtip1.htm)
Staggered and eclipsed ethane (http://wiki.jmol.org:81/index.php/User:Bduke)

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