Acetylene - Wikipedia, the free encyclopedia Page 1 of 6

Acetylene
From Wikipedia, the free encyclopedia
Acetylene
Acetylene (systematic name: ethyne) is a hydrocarbon
belonging to the group of alkynes. It is considered to
be the simplest of all alkynes as it consists of two
hydrogen atoms and two carbon atoms. Acetylene is an
unsaturated organic compound because its four atoms
are triple bonded through a covalent bond.

The carbon-carbon triple bond leaves the carbon atoms

with two sp hybrid orbitals for sigma bonding, placing IUPAC
Ethyne
name
all four atoms in the same straight line, with CCH bond
angles of 180°. Identifiers
74-86-2
Acetylene was discovered in 1836 by Edmund Davy CAS (http://www.emolecules.com/cgi-
who identified it as a "new carburet of hydrogen." It number bin/search?t=ss&q=74-86-
2&c=0&v=)
was rediscovered in 1860 by French chemist Marcellin
SMILES C#C
Berthelot, who coined the name "acetylene." The
Properties
Nobel Laureate Gustaf Dalén was blinded by an
acetylene explosion. Molecular C H
formula 2 2
Molar
Contents 26.0373 g/mol
mass
Density 1.09670 kg/m³ gas
„ 1 Preparation Melting
„ 2 Reactions point -84 °C
„ 2.1 Reppe chemistry Boiling
„ 3 Uses point -83.8 °C
„ 4 Safety and handling Acidity
„ 4.1 Compression (pKa) 25
„ 4.2 Toxic effects
Except where noted otherwise, data are given for
„ 4.3 Fire hazard
materials in their standard state
„ 4.4 Incompatibilities (at 25 °C, 100 kPa)
„ 5 Other meanings Infobox disclaimer and references
„ 6 Natural occurrence
„ 7 References
„ 8 External links

Preparation
The principal raw materials for acetylene manufacture are calcium carbonate (limestone) and coal.
The calcium carbonate is first converted into calcium oxide and the coal into coke, then the two are
reacted with each other to form calcium carbide and carbon monoxide:

CaO + 3C → CaC2 + CO

Calcium carbide (or calcium acetylide) and water are then reacted by any of several methods to
produce acetylene and calcium hydroxide. This reaction was discovered by Friedrich Wohler in
1862.

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CaC2 + 2H2O → Ca(OH)2 + C2H2

Calcium carbide synthesis requires an extremely high temperature, ~2000 degrees Celsius, so the
reaction is performed in an electric arc furnace. This reaction was an important part of the late-1800s
revolution in chemistry enabled by the massive hydroelectric power project at Niagara Falls.

Acetylene can also be manufactured by the partial combustion of methane with oxygen, or by the
cracking of hydrocarbons.

Berthelot was able to prepare acetylene from methyl alcohol, ethyl alcohol, ethylene, or ether, when
he passed any one of these as a gas or vapour through a red-hot tube. Berthelot also found acetylene
was formed by sparking electricity through mixed cyanogen and hydrogen gases. He was also able to
form acetylene directly by combining pure hydrogen with carbon using electrical discharge of a
carbon arc.

Reactions
„ Above 400 °C (673 K), which is quite low for a hydrocarbon, the pyrolysis of acetylene will
start. The main products are the dimer vinylacetylene (C4H4) and benzene. At temperatures
above 900 °C (1173 K), the main product will be soot.
„ Using acetylene, Berthelot was the first to show that an aliphatic compound could form an
aromatic compound when he heated acetylene in a glass tube to produce benzene with some
toluene. Berthelot oxidized acetylene to yield acetic acid and oxalic acid. He found acetylene
could be reduced to form ethylene and ethane.
„ Polymerization of acetylene with Ziegler-Natta catalysts produces polyacetylene films.
Polyacetylene, a chain of carbon molecules with alternating single and double bonds, was the
first organic semiconductor to be discovered; reaction with iodine produces an extremely
conductive material.
„ In the Kucherov reaction (invented in 1881 by the Russian chemist Mikhail Kucherov) [1]
acetylene is hydrated to acetaldehyde with a mercury salt such as mercury(II) bromide. Before
the advent of the Wacker process this reaction was conducted on an industrial scale [2].

Reppe chemistry

Walter Reppe discovered that acetylene can react at high pressures with heavy metal catalysts to give
industrially significant chemicals:

„ Acetylene reacting with alcohols, hydrogen cyanide, hydrogen chloride, or carboxylic acids to
give vinyl compounds:

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„ With aldehydes to give ethynyl diols.

This is industrially used to produce 1,4-butynediol from formaldehyde and acetylene:

HCCH + CH2O → CH2(OH)CCCH2OH

„ With carbon monoxide to give acrylic acid, or acrylic esters, which can be used to produce
acrylic glass.

„ Cyclicization to give benzene and cyclooctatetraene:

Uses
Approximately 80 percent of the acetylene produced annually in the United States is used in
chemical synthesis. The remaining 20 percent is used primarily for oxyacetylene gas welding and
cutting due to the high temperature of the flame; combustion of acetylene with oxygen produces a
flame of over 3300 °C (6000 °F), releasing 11.8 kJ/g. Oxyacetylene is the hottest burning common
fuel gas.[3]. Cyanogen, a more exotic gas, produces a flame of over 4525°C (8180°F) when it burns
in oxygen.[4]
Acetylene is also used in the acetylene ('carbide') lamp, once used by miners (not to be confused
with the Davy lamp), on vintage cars, and still sometimes used by cavers. In this context, the
acetylene is generated by dripping water from the upper chamber of the lamp onto calcium carbide
(CaC2) pellets in the base of the lamp.

In former times a few towns used acetylene for lighting, including Tata in Hungary where it was
installed on 24 July 1897, and North Petherton, England in 1898.

In modern times acetylene is sometimes used for carburization (that is, hardening) of steel when the
object is too large to fit into a furnace.[3]
Acetylene has been proposed as a carbon feedstock for molecular manufacturing using
nanotechnology. Since it does not occur naturally, using acetylene could limit out-of-control self-
replication.

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Acetylene is used to volatilize carbon in radiocarbon dating. The carbonaceous material in the
archeological sample reacted in a small specialized research furnace with lithium metal to form
lithium carbide (also known as lithium acetylide). The carbide can then be reacted with water, as
usual, to form acetylene gas to be fed into mass spectrometer to sort out the isotopic ratio of carbon
14 to carbon 12.

The Future

The use of acetylene is expected to continue a gradual increase in the future as new applications are
developed. One new application is the conversion of acetylene to ethylene for use in making a
variety of polyethylene plastics. In the past, a small amount of acetylene had been generated and
wasted as part of the steam cracking process used to make ethylene. A new catalyst developed by
Phillips Petroleum allows most of this acetylene to be converted into ethylene for increased yields at
a reduced overall cost.[5]

Safety and handling

Compression

Due to the carbon-to-carbon triple bond, acetylene gas is fundamentally unstable, and will
decompose in an exothermic reaction if compressed to any great extent. Acetylene can explode with
extreme violence if the pressure of the gas exceeds about 100 kPa (≈14.5 psi) as a gas or when in
liquid or solid form, so it is shipped and stored dissolved in acetone or dimethylformamide (DMF),
contained in a metal cylinder with porous filling (Agamassan), which renders it safe to transport and
use.

There are strict regulations on the shipment of dangerous gas cylinders throughout the world. The
use of dissolved acetylene is decreasing rapidly, due to favourable flameless welding processes.

Toxic effects

Inhaling acetylene may cause dizziness, headache and nausea.[6] It may also contain toxic impurities:
the Compressed Gas Association Commodity Specification for acetylene
(http://www.cganet.com/publication_detail.asp?id=G-1.1) has established a grading system for
identifying and quantifying phosphine, arsine, and hydrogen sulfide content in commercial grades of
acetylene in order to limit exposure to these impurities. The sulfur, phosphorus and arsenic are
carryovers from the synthesis ingredient coke, an impure form of carbon and different, organic
impurities would be expected from the thermal cracking of hydrocarbons source.

While the impurities in acetylene can be toxic and even fatal, pure acetylene is of a very low toxicity
(not counting the "narcotic" effects). Up to 80% percent, (v/v) acetylene has been administered to
surgical patients as a general anaesthetic. The trade name for acetylene was "narcylene." It was used
a fair amount experimentally in Germany in their impoverished 1920's, perhaps on several thousand
patients. Medically, acetylene was considered to be nearly as safe as nitrous oxide and with a slightly
higher potency, allowing for the use of higher percentages of oxygen in the blend; it is about 50%
more potent. However, the use of acetylene and oxygen mixtures was dropped after several gas
explosions inside patients' lungs. The energy of these explosions would be expected to exceed any of
the flammable inhalation anesthetics due to the instability of the triple bond (cyclopropane would be
nearly as bad). It was suggested that such an internal thorax explosion could not occur with air
mixtures (without purified oxygen).

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Acetylene has been infrequently abused in a manner akin to nitrous oxide abuse up through modern
times, according to the literature. Such abuse can result in the death of the abuser due to toxicity of
the above mentioned impurities phosphine, arsine, and hydrogen sulfide. Since the gas is charged
(absorbed) into tanks soaked with acetone over a solid matrix, some acetone comes out with the gas,
further contributing to the poisonings. The driver for this abusive behavior is better understood with
the view of acetylene's anesthetic properties and addictive behaviors.

Impurities in acetylene are easily detectable by smell. Pure acetylene is a colorless and odorless gas.
The characteristic garlic-like odor of technical grade acetylene is attributable to contamination by
impurities. Impurities which may be present include: divinyl sulfide, ammonia, oxygen, nitrogen,
phosphine, arsine, methane, carbon dioxide, carbon monoxide, hydrogen sulfide, vinyl acetylene,
divinyl acetylene, diacetylene, propadiene, hexadiene, butadienyl acetylene, and methyl acetylene.

Fire hazard

Mixtures with air containing between 3% and 82% acetylene are explosive on ignition. The
minimum ignition temperature is 335 °C.[6] The majority of acetylene's chemical energy is what is
not contained in the carbon-carbon triple bond; that is, it is greater than that of three carbon-carbon
bonds spread out, but is disallowed therefrom because of the spaces between its mate carbon and all
other carbons likewise shielded in charge.

Incompatibilities

„ bromine, chlorine, copper, mercury, silver.

Other meanings
Sometimes the plural "acetylenes" may refer to the class of organic chemical compounds known as
alkynes which contain the -C≡C- group.

Natural occurrence
Acetylene is a moderately common chemical in the universe, often associated with the atmospheres
of gas giants.[7] One curious discovery of acetylene is on Enceladus, a moon of Saturn. Natural
acetylene is believed to form from either catalytic decomposition of long chain hydrocarbons or at
temperatures ≥ 1,770 kelvin. Since such temperatures are highly unlikely on such a small distant
body, this discovery is potentially suggestive of catalytic reactions within the moon, making it a
promising site to search for prebiotic chemistry.[8][9]

References
1. ^ Kutscheroff, M. Ber. Bunsenges. Phys. Chemie 1881, 1540–1542.
2. ^ Hydration of Acetylene: A 125th Anniversary Dmitry A. Ponomarev and Sergey M.
Shevchenko Journal of Chemical Education Vol. 84 No. 10 October 2007 1725
3. ^ a b http://www.boc.com/products_and_services/by_product/acetylene/index.asp
4. ^ Thomas, N. & Gaydon, A. G.; Brewer, L. (March 1952), "Cyanogen Flames and the
Dissociation Energy of N2 (http://scitation.aip.org/getabs/servlet/GetabsServlet?
prog=normal&id=JCPSA6000020000003000369000001&idtype=cvips&gifs=yes)", The
Journal of Chemical Physics 20 (3): 369-374,

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<http://scitation.aip.org/getabs/servlet/GetabsServlet?
prog=normal&id=JCPSA6000020000003000369000001&idtype=cvips&gifs=yes>
5. ^ Acetylene: How Products are Made (http://science.enotes.com/how-products-
encyclopedia/acetylene)
6. ^ a b Muir, GD (ed.) 1971, Hazards in the Chemical Laboratory, The Royal Institute of
Chemistry, London.
7. ^ W. M. Keck Observatory (20 Dec 2005). Precursor to Proteins and DNA found in Stellar
Disk (http://www.keckobservatory.org/article.php?id=39). Press release.
8. ^ Emily Lakdawalla (17 Mar 2006). LPSC: Wednesday afternoon: Cassini at Enceladus
(http://www.planetary.org/blog/article/00000498/). The Planetary Society.
9. ^ John Spencer and David Grinspoon (25 Jan 2007). "Planetary science: Inside Enceladus".
Nature 445: 376-377. doi:10.1038/445376b (http://dx.doi.org/10.1038/445376b).

External links
„ Acetylene at Chemistry Comes Alive!
(http://jchemed.chem.wisc.edu/JCESoft/CCA/CCA5/MAIN/1ORGANIC/ORG07/MENU.HTM
„ Acetylene, the Principles of Its Generation and Use (http://www.gutenberg.org/etext/8144),
available at Project Gutenberg.

Retrieved from "http://en.wikipedia.org/wiki/Acetylene"

Category: Alkynes

„ This page was last modified 01:46, 9 November 2007.

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