acetylene

A colorless, highly flammable or explosive gas, C₂H₂, used for metal welding and cutting and as an illuminant. Also called ethyne.

Background

Acetylene is a colorless, combustible gas with a distinctive odor. When acetylene is liquefied, compressed, heated, or mixed with air, it becomes highly explosive. As a result special precautions are required during its production and handling. The most common use of acetylene is as a raw material for the production of various organic chemicals including 1,4-butanediol, which is widely used in the preparation of polyurethane and polyester plastics. The second most common use is as the fuel component in oxy-acetylene welding and metal cutting. Some commercially useful acetylene compounds include acetylene black, which is used in certain dry-cell batteries, and acetylenic alcohols, which are used in the synthesis of vitamins.

Acetylene was discovered in 1836, when Edmund Davy was experimenting with potassium carbide. One of his chemical reactions produced a flammable gas, which is now known as acetylene. In 1859, Marcel Morren successfully generated acetylene when he used carbon electrodes to strike an electric arc in an atmosphere of hydrogen. The electric arc tore carbon atoms away from the electrodes and bonded them with hydrogen atoms to form acetylene molecules. He called this gas carbonized hydrogen.

By the late 1800s, a method had been developed for making acetylene by reacting calcium carbide with water. This generated a controlled flow of acetylene that could be combusted in air to produce a brilliant white light. Carbide lanterns were used by miners and carbide lamps were used for street illumination before the general availability of electric lights. In 1897, Georges Claude and A. Hess noted that acetylene gas could be safely stored by dissolving it in acetone. Nils Dalen used this new method in 1905 to develop long-burning, automated marine and railroad signal lights. In 1906, Dalen went on to develop an acetylene torch for welding and metal cutting.

In the 1920s, the German firm BASF developed a process for manufacturing acetylene from natural gas and petroleum-based hydrocarbons. The first plant went into operation in Germany in 1940. The technology came to the United States in the early 1950s and quickly became the primary method of producing acetylene.

Demand for acetylene grew as new processes were developed for converting it into useful plastics and chemicals. In the United States, demand peaked sometime between 1965 and 1970, then fell off sharply as new, lower-cost alternative conversion materials were discovered. Since the early 1980s, the demand for acetylene has grown slowly at a rate of about 2-4% per year.

In 1991, there were eight plants in the United States that produced acetylene. Together they produced a total of 352 million lb (160 million kg) of acetylene per year. Of this production, 66% was derived from natural gas and 15% from petroleum processing. Most acetylene from these two sources was used on or near the site where it was produced to make other organic chemicals. The remaining 19% came from calcium carbide. Some of the acetylene from this source was used to make organic chemicals, and the rest was used by regional industrial gas producers to fill pressurized cylinders for local welding and metal cutting customers.

In Western Europe, natural gas and petroleum were the principal sources of acetylene in 1991, while calcium carbide was the principal source in Eastern Europe and Japan.

Raw Materials

Acetylene is a hydrocarbon consisting of two carbon atoms and two hydrogen atoms. Its chemical symbol is C₂H₂. For commercial purposes, acetylene can be made from several different raw materials depending on the process used.

The simplest process reacts calcium carbide with water to produce acetylene gas and a calcium carbonate slurry, called hydrated lime. The chemical reaction may be written as CaC₂ + 2 H₂O → C₂H₂ + Ca(OH)₂.

Other processes use natural gas, which is mostly methane, or a petroleum-based hydrocarbon such as crude oil, naphtha, or bunker C oil as raw materials. Coal can also be used. These processes use high temperature to convert the raw materials into a wide variety of gases, including hydrogen, carbon monoxide, carbon dioxide, acetylene, and others. The chemical reaction for converting methane into acetylene and hydrogen may be written 2 CH₄ → C₂H₂ + 3 H₂. The other gases are the products of combustion with oxygen. In order to separate the acetylene, it is dissolved in a solvent such as water, anhydrous ammonia, chilled methanol, or acetone, or several other solvents depending on the process.

The Manufacturing
Process

There are two basic conversion processes used to make acetylene. One is a chemical reaction process, which occurs at normal temperatures. The other is a thermal cracking process, which occurs at extremely high temperatures.

Here are typical sequences of operations used to convert various raw materials into acetylene by each of the two basic processes.

Chemical reaction process

Acetylene may be generated by the chemical reaction between calcium carbide and water. This reaction produces a considerable amount of heat, which must be removed to prevent the acetylene gas from exploding. There are several variations of this process in which either calcium carbide is added to water or water is added to calcium carbide. Both of these variations are called wet processes because an excess amount of water is used to absorb the heat of the reaction. A third variation, called a dry process, uses only a limited amount of water, which then evaporates as it absorbs the heat. The first variation is most commonly used in the United States and is described below.

1. Most high-capacity acetylene generators use a rotating screw conveyor to feed calcium carbide granules into the reaction chamber, which has been filled to a certain level with water. The granules measure about 0.08 in x 0.25 in (2 mm x 6 mm), which provides the right amount of exposed surfaces to allow a complete reaction. The feed rate is determined by the desired rate of gas flow and is controlled by a pressure switch in the chamber. If too much gas is being produced at one time, the pressure switch opens and cuts back the feed rate.
2. To ensure a complete reaction, the solution of calcium carbide granules and water is constantly agitated by a set of rotating paddles inside the reaction chamber. This also prevents any granules from floating on the surface where they could over-heat and ignite the acetylene
3. The acetylene gas bubbles to the surface and is drawn off under low pressure. As it leaves the reaction chamber, the gas is cooled by a spray of water. This water spray also adds water to the reaction chamber to keep the reaction going as new calcium carbide is added. After the gas is cooled, it passes through a flash arrester, which prevents any accidental ignition from equipment downstream of the chamber.
4. As the calcium carbide reacts with the water, it forms a slurry of calcium carbonate, which sinks to the bottom of the chamber. Periodically the reaction must be stopped to remove the built-up slurry. The slurry is drained from the chamber and pumped into a holding pond, where the calcium carbonate settles out and the water is drawn off. The thickened calcium carbonate is then dried and sold for use as an industrial waste water treatment agent, acid neutralizer, or soil conditioner for road construction.

Thermal cracking process

Acetylene may also be generated by raising the temperature of various hydrocarbons to the point where their atomic bonds break, or crack, in what is known as a thermal cracking process. After the hydrocarbon atoms break apart, they can be made to rebond to form different materials than the original raw materials. This process is widely used to convert oil or natural gas to a variety of chemicals.

There are several variations of this process depending on the raw materials used and the method for raising the temperature. Some cracking processes use an electric arc to heat the raw materials, while others use a combustion chamber that burns part of the hydrocarbons to provide a flame. Some acetylene is generated as a coproduct of the steam cracking process used to make ethylene. In the United States, the most common process uses a combustion chamber to heat and burn natural gas as described below.

1. Natural gas, which is mostly methane, is heated to about 1,200° F (650° C). Preheating the gas will cause it to self-ignite once it reaches the burner and requires less oxygen for combustion.
2. The heated gas passes through a narrow pipe, called a venturi, where oxygen is injected and mixed with the hot gas.
3. The mixture of hot gas and oxygen passes through a diffuser, which slows its velocity to the desired speed. This is critical. If the velocity is too high, the incoming gas will blow out the flame in the burner. If the velocity is too low, the flame can flash back and ignite the gas before it reaches the burner.
4. The gas mixture flows into the burner block, which contains more than 100 narrow channels. As the gas flows into each channel, it self-ignites and produces a flame which raises the gas temperature to about 2,730° F (1,500° C). A small amount of oxygen is added in the burner to stabilize the combustion.
5. The burning gas flows into the reaction space just beyond the burner where the high temperature cause about one-third of the methane to be converted into acetylene, while most of the rest of the methane is burned. The entire combustion process takes only a few milliseconds.
6. The flaming gas is quickly quenched with water sprays at the point where the conversion to acetylene is the greatest. The cooled gas contains a large amount of carbon monoxide and hydrogen, with lesser amounts of carbon soot, plus carbon dioxide, acetylene, methane, and other gases.
7. The gas passes through a water scrubber, which removes much of the carbon soot. The gas then passes through a second scrubber where it is sprayed with a solvent known as N-methylpyrrolidinone which absorbs the acetylene, but not the other gases.
8. The solvent is pumped into a separation tower where the acetylene is boiled out of the solvent and is drawn off at the top of the tower as a gas, while the solvent is drawn out of the bottom.

Storage and Handling

Because acetylene is highly explosive, it must be stored and handled with great care. When it is transported through pipelines, the pressure is kept very low and the length of the pipeline is very short. In most chemical production operations, the acetylene is transported only as far as an adjacent plant, or "over the fence" as they say in the chemical processing business.

When acetylene must be pressurized and stored for use in oxy-acetylene welding and metal cutting operations, special storage cylinders are used. The cylinders are filled with an absorbent material, like diatomaceous earth, and a small amount of acetone. The acetylene is pumped into the cylinders at a pressure of about 300 psi (2,070 kPa), where it is dissolved in the acetone. Once dissolved, it loses its explosive capability, making it safe to transport. When the cylinder valve is opened, the pressure drop causes some of the acetylene to vaporize into gas again and flow through the connecting hose to the welding or cutting torch.

Quality Control

Grade B acetylene may have a maximum of 2% impurities and is generally used for oxyacetylene welding and metal cutting. Acetylene produced by the chemical reaction process meets this standard. Grade A acetylene may have no more than 0.5% impurities and is generally used for chemical production processes. Acetylene produced by the thermal cracking process may meet this standard or may require further purification, depending on the specific process and raw materials.

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.

Where to Learn More

Books

Brady, George S., Henry R. Clauser, and John A. Vaccari. Materials Handbook, 14th edition. McGraw-Hill, 1997.

Kroschwitz, Jacqueline I. and Mary Howe-Grant, ed. Encyclopedia of Chemical Technology, 4th edition. John Wiley and Sons, Inc., 1993.

Other

Acetylene Pamphlet G-1. Compressed Gas Association, 1990.

Compressed Gas Association. http://www.cganet.com.

[Article by: Chris Cavette]

An organic compound with the formula C₂H₂ or HC&tbnd;CH. The first member of the alkynes, acetylene is a gas with a narrow liquid range; the triple point is −81°C (−114°F). The heat of formation (ΔH°_f) is +227 kilojoules/mole, and acetylene is the most endothermic compound per carbon of any hydrocarbon. The compound is thus extremely energy-rich and can decompose with explosive force. At one time acetylene was a basic compound for much chemical manufacturing. It is highly reactive and is a versatile source of other reactive compounds.

The availability of acetylene does not depend on petroleum liquids, since it can be prepared by hydrolysis of calcium carbide (CaC₂), obtained from lime (CaO), and charcoal or coke (C). In modern practice, methane (CH₄) is passed through a zone heated to 1500°C (2732°F) for a few milliseconds, and acetylene is then separated from the hydrogen in the effluent gas.

The main use of acetylene is in the manufacture of compounds derived from butyne-1,4-diol. The latter is obtained by condensation of acetylene with two moles of formaldehyde and is converted to butyrolactone, tetrahydrofuran, and pyrrolidone. Two additional products, vinyl fluoride and vinyl ether, are also based on acetylene.

Because of the very high heat of formation and combustion, an acetylene-oxygen mixture provides a very high temperature flame for welding and metal cutting. For this purpose acetylene is shipped as a solution in acetone, loaded under pressure in cylinders that contain a noncombustible spongy packing. See also Alkyne.

For more information on acetylene, visit Britannica.com.

A colorless gas, when mixed with oxygen, burns at a temperature of about 3500°C; used in welding.

A colorless, combustible, explosive gas, the simplest triple-bonded hydrocarbon.

"HCCH" redirects here. For other uses, see HCCH (disambiguation).

Acetylene
IUPAC name	Ethyne
Identifiers
CAS number	74-86-2 Y
UN number	1001 (dissolved) 3138 (in mixture with ethylene and propylene)
SMILES	C#C
InChI	1/C2H2/c1-2/h1-2H
InChI key	HSFWRNGVRCDJHI-UHFFFAOYAY
ChemSpider ID	6086
Properties
Molecular formula	C2H2
Molar mass	26.04 g mol−1
Density	1.097 kg/m3
Melting point	−80.8 °C (189 K, subl)
Boiling point	−84 °C
Acidity (pKa)	25
Structure
Molecular shape	Linear
Thermochemistry
Std enthalpy of formation ΔfHo298	+226.88 kJ/mol
Hazards
NFPA 704	4 1 3
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Acetylene (IUPAC name: ethyne) is the chemical compound with the formula HC₂H. It is a hydrocarbon and the simplest alkyne. This colourless gas is widely used as a fuel and a chemical building block. It is unstable in pure form and thus is usually handled as a solution.

As an alkyne, acetylene is unsaturated because its two carbon atoms are bonded together in a triple bond. The carbon-carbon triple bond places all four atoms in the same straight line, with CCH bond angles of 180°.

Contents 1 Discovery 2 Preparation 3 Reactions 3.1 Reppe chemistry 3.2 Welding 3.3 Niche and historically interesting applications 4 Natural occurrence 5 Safety and handling 6 References 7 External links

Discovery

Acetylene was discovered in 1836 by Edmund Davy who identified it as a "new carburet of hydrogen". It was rediscovered in 1860 by French chemist Marcellin Berthelot, who coined the name "acetylene". Berthelot was able to prepare this gas by passing vapours of organic compounds (methanol, ethanol, etc.) through a red-hot tube and collecting the effluent. He also found acetylene was formed by sparking electricity through mixed cyanogen and hydrogen gases. Berthelot later obtained acetylene directly by passing hydrogen between the poles of a carbon arc.^[1]

Preparation

Nowadays acetylene is mainly manufactured by the partial combustion of methane or appears as a side product in the ethylene stream from cracking of hydrocarbons. Approximately 400,000 tonnes are produced this way annually.^[2] Its presence in ethylene is usually undesirable because of its explosive character and its ability to poison Ziegler-Natta catalysts. It is selectively hydrogenated into ethylene, usually using Pd-Ag catalysts.^[3]

Until the 1950s, when oil supplanted coal as the chief source of carbon, acetylene (and the aromatic fraction from coal tar) was the main source of organic chemicals in the chemical industry. It was prepared by the hydrolysis of calcium carbide, a reaction discovered by Friedrich Wöhler in 1862 and still familiar to students:

CaC₂ + 2H₂O → Ca(OH)₂ + C₂H₂

Calcium carbide production requires extremely high temperatures, ~2000 °C, necessitating the use of an electric arc furnace. In the US, this process was an important part of the late-1800s revolution in chemistry enabled by the massive hydroelectric power project at Niagara Falls.

Reactions

Main article: alkyne

Approximately 80 percent of the acetylene produced annually in the United States is used in chemical synthesis^{[citation needed]}. One new application is the conversion of acetylene to ethylene for use in making a variety of polyethylene plastics. An important reaction of acetylene is its combustion, the basis of the acetylene welding technologies. Otherwise, its major applications involve its conversion to acrylic acid derivatives. Acetylides with many metal ions by reactions of with solutions of their salts. Several, e.g., silver acetylide and copper acetylide, are powerful and very dangerous explosives. Copper acetylide is also formed by reacting acetylene with metallic copper or its alloys; these materials are therefore unsuitable for installations for handling acetylene.

Reppe chemistry

Walter Reppe discovered that in the presence of metal catalysts, acetylene can react to give a wide range of industrially significant chemicals.

• With alcohols, hydrogen cyanide, hydrogen chloride, or carboxylic acids to give vinyl compounds:

• With aldehydes to give ethynyl diols.

1,4-Butynediol is produced industrially in this way from formaldehyde and acetylene.

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

• Cyclicization to give benzene and cyclooctatetraene:

Welding

Approximately 20 percent of acetylene is consumed for oxyacetylene gas welding and cutting due to the high temperature of the flame; combustion of acetylene with oxygen produces a flame of over 3600 K (3300 °C, 6000 °F), releasing 11.8 kJ/g. Oxyacetylene is the hottest burning common fuel gas.^[4] Acetylene is the third hottest natural chemical flame after cyanogen at 4798 K (4525 °C, 8180 °F) and dicyanoacetylene's 5260 K (4990 °C, 9010 °F). Oxy-acetylene welding was a very popular welding process in previous decades, however, the development and advantages of arc-based welding processes have made oxy-fuel welding nearly extinct. Acetylene usage for welding has dropped significantly. However, oxy-fuel cutting is still very popular and oxy-acetylene cutting is present in nearly every metal fabrication shop. For use in welding and cutting, the working pressures must be controlled by a regulator, or the gas will spontaneously combust.

Acetylene fuel container/burner as used in the island of Bali

Niche and historically interesting applications

In 1881, the Russian chemist Mikhail Kucherov^[5] described the hydration of acetylene to acetaldehyde using catalysts such as mercury(II) bromide. Before the advent of the Wacker process, this reaction was conducted on an industrial scale.^[6]

The polymerization of acetylene with Ziegler-Natta catalysts produces polyacetylene films. Polyacetylene, a chain of CH centres with alternating single and double bonds, was the one of first discovered organic semiconductors. Its reaction with iodine produces a highly electrically conducting material. Although such materials are not useful, these discoveries led to the developments of organic semiconductors, as recognized by the Nobel Prize in Chemistry in 2000 to Alan J. Heeger, Alan G MacDiarmid, and Hideki Shirakawa.

In the early 20th century acetylene was widely used for illumination, including street lighting in some towns.^[7] Some early automobiles used carbide lamps before the adoption of electric headlights.

Acetylene is sometimes used for carburization (that is, hardening) of steel when the object is too large to fit into a furnace.^[4]

Acetylene is used to volatilize carbon in radiocarbon dating. The carbonaceous material in an archeological sample is reacted with lithium metal in a small specialized research furnace 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.

Natural occurrence

Acetylene is a moderately common chemical in the universe, often associated with the atmospheres of gas giants.^[8] 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 at temperatures of 1,770 K and above. 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.^[9][10]

Safety and handling

Acetylene is not especially toxic but when generated from calcium carbide it can contain toxic impurities such as traces of phosphine and arsine. It is also highly flammable (hence its use in welding). Its singular hazard is associated with its intrinsic instability; samples of concentrated or pure acetylene will explosively decompose. Acetylene can explode with extreme violence if the pressure of the gas exceeds about 200 kPa (39 psi) as a gas^[11] or when in liquid or solid form. It is therefore shipped and stored dissolved in acetone or dimethylformamide (DMF), contained in a metal cylinder with a porous filling (Agamassan), which renders it safe to transport and use, given proper handling.

References

1. ^ Acetylene
2. ^ Peter Pässler, Werner Hefner, Klaus Buckl, Helmut Meinass, Andreas Meiswinkel, Hans-Jürgen Wernicke, Günter Ebersberg, Richard Müller, Jürgen Bässler, Hartmut Behringer, Dieter Mayer “Acetylene” in Ullmann's Encyclopedia of Industrial Chemistry, 2008, Wiley-VCH, Weinheim. doi:10.1002/14356007.a01_097.pub3. Article Online Posting Date: 15 October 2008
3. ^ Acetylene: How Products are Made
4. ^ ^{a b} Acetylene, BOC
5. ^ Kutscheroff, M. "Ueber eine neue Methode direkter Addition von Wasser (Hydratation) an die Kohlenwasserstoffe der Acetylenreihe" Berichte der deutschen chemischen Gesellschaft 1881, Volume 14, 1540–1542. doi:10.1002/cber.188101401320
6. ^ Dmitry A. Ponomarev and Sergey M. Shevchenko (2007). "Hydration of Acetylene: A 125th Anniversary". J. Chem. Ed. 84 (10): 1725. http://jchemed.chem.wisc.edu/HS/Journal/Issues/2007/OctACS/ACSSub/p1725.pdf. 
7. ^ The 100 most important chemical compounds: a reference guide
8. ^ W. M. Keck Observatory (20 December 2005). "Precursor to Proteins and DNA found in Stellar Disk". Press release. http://www.keckobservatory.org/article.php?id=39. 
9. ^ Emily Lakdawalla (17 March 2006). "LPSC: Wednesday afternoon: Cassini at Enceladus". The Planetary Society. http://www.planetary.org/blog/article/00000498/. 
10. ^ John Spencer and David Grinspoon (25 January 2007). "Planetary science: Inside Enceladus". Nature 445: 376–377. doi:10.1038/445376b. 
11. ^ Korzun, Mikołaj (1986). 1000 słów o materiałach wybuchowych i wybuchu. Warszawa: Wydawnictwo Ministerstwa Obrony Narodowej. ISBN 83-11-07044-X. OCLC 69535236. 

External links

• Acetylene at Chemistry Comes Alive!
• Acetylene, the Principles of Its Generation and Use at Project Gutenberg
• Movie explaining acetylene formation from calcium carbide and the explosive limits forming fire hazards

v • d • e Alkynes Ethyne ( C2H2 ) • Propyne ( C3H4 ) • Butyne ( C4H6 ) • Pentyne ( C5H8 ) • Hexyne ( C6H10 ) • Heptyne ( C7H12 ) • Octyne ( C8H14 ) • Nonyne ( C9H16 ) • Decyne ( C10H18 ) • Undecyne ( C11H20 )

This entry is from Wikipedia, the leading user-contributed encyclopedia. It may not have been reviewed by professional editors (see full disclaimer)

Dansk (Danish)
n. - acetylen

Nederlands (Dutch)
acetyleen(gas)

Français (French)
n. - acétylène

Deutsch (German)
n. - (chem.) Acetylen

Ελληνική (Greek)
n. - (χημ.) ακετυλένιο (κν. ασετυλίνη)

Italiano (Italian)
acetilene

Português (Portuguese)
n. - acetileno (m) (Quím.)

Русский (Russian)
ацетилен

Español (Spanish)
n. - acetileno

Svenska (Swedish)
n. - acetylengas

中文（简体）(Chinese (Simplified))
电石气, 乙炔

中文（繁體）(Chinese (Traditional))
n. - 電石氣, 乙炔

한국어 (Korean)
n. - 아세틸렌(가스)

日本語 (Japanese)
n. - アセチレン

العربيه (Arabic)
‏(الاسم) أسيتيلين : غاز عديم أللون يستخدم في ألتلحيم‏

עברית (Hebrew)
n. - ‮גז חסר-צבע המשמש לריתוך, אצטילין (גאז)‬

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