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Acetylene (
systematic name A systematic name is a name given in a systematic way to one unique group, organism, object or chemical substance, out of a specific population or collection. Systematic names are usually part of a nomenclature. A semisystematic name or semitrivial ...
: ethyne) is the
chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
with the formula and structure . It is a
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...
and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure form and thus is usually handled as a solution. Pure acetylene is odorless, but commercial grades usually have a marked odor due to impurities such as
divinyl sulfide Divinyl sulfide is the organosulfur compound with the formula S(CH=CH2)2. It is a colorless liquid with a faint odor. It is found in the oil of some species of ''Allium''. It is notable as the product from hydrogen sulfide and acetylene, a com ...
and
phosphine Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting ...
.Compressed Gas Association (1995
Material Safety and Data Sheet – Acetylene
As an alkyne, acetylene is unsaturated because its two carbon atoms are bonded together in a
triple bond A triple bond in chemistry is a chemical bond between two atoms involving six bonding electrons instead of the usual two in a covalent single bond. Triple bonds are stronger than the equivalent single bonds or double bonds, with a bond order o ...
. The carbon–carbon triple bond places all four atoms in the same straight line, with CCH bond angles of 180°.


Discovery

Acetylene was discovered in 1836 by
Edmund Davy Edmund Davy FRS (1785 – 5 November 1857)Christopher F. Lindsey, 'Davy, Edmund (1785–1857)’, Oxford Dictionary of National Biography, Oxford University Press, 200 accessed 6 April 2008/ref> was a professor of chemistry at the Royal Cork Inst ...
, who identified it as a "new carburet of hydrogen". It was an accidental discovery while attempting to isolate
potassium Potassium is the chemical element with the symbol K (from Neo-Latin ''kalium'') and atomic number19. Potassium is a silvery-white metal that is soft enough to be cut with a knife with little force. Potassium metal reacts rapidly with atmosphe ...
metal. By heating
potassium carbonate Potassium carbonate is the inorganic compound with the formula K2 CO3. It is a white salt, which is soluble in water. It is deliquescent, often appearing as a damp or wet solid. Potassium carbonate is mainly used in the production of soap and gl ...
with carbon at very high temperatures, he produced a residue of what is now known as
potassium carbide In chemistry, a carbide usually describes a compound composed of carbon and a metal. In metallurgy, carbiding or carburizing is the process for producing carbide coatings on a metal piece. Interstitial / Metallic carbides The carbides of the ...
, (K2C2), which reacted with water to release the new gas. It was rediscovered in 1860 by French chemist
Marcellin Berthelot Pierre Eugène Marcellin Berthelot (; 25 October 1827 – 18 March 1907) was a French chemist and Republican politician noted for the ThomsenBerthelot principle of thermochemistry. He synthesized many organic compounds from inorganic substa ...
, who coined the name ''acétylène''. Berthelot's empirical formula for acetylene (C4H2), as well as the alternative name "''quadricarbure d'hydrogène''" (hydrogen quadricarbide), were incorrect because many chemists at that time used the wrong atomic mass for carbon (6 instead of 12). 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 Effluent is wastewater from sewers or industrial outfalls that flows directly into surface waters either untreated or after being treated at a facility. The term has slightly different meanings in certain contexts, and may contain various pollut ...
. He also found that acetylene was formed by sparking electricity through mixed
cyanogen Cyanogen is the chemical compound with the formula ( C N)2. It is a colorless and highly toxic gas with a pungent odor. The molecule is a pseudohalogen. Cyanogen molecules consist of two CN groups – analogous to diatomic halogen molecule ...
and
hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...
gases. Berthelot later obtained acetylene directly by passing hydrogen between the poles of a
carbon arc An arc lamp or arc light is a lamp that produces light by an electric arc (also called a voltaic arc). The carbon arc light, which consists of an arc between carbon electrodes in air, invented by Humphry Davy in the first decade of the 1800s, ...
.


Preparation

Since the 1950s, acetylene has mainly been manufactured by the partial
combustion Combustion, or burning, is a high-temperature exothermic redox chemical reaction between a fuel (the reductant) and an oxidant, usually atmospheric oxygen, that produces oxidized, often gaseous products, in a mixture termed as smoke. Combusti ...
of
methane Methane ( , ) is a chemical compound with the chemical formula (one carbon atom bonded to four hydrogen atoms). It is a group-14 hydride, the simplest alkane, and the main constituent of natural gas. The relative abundance of methane on Eart ...
. It is a recovered side product in production of
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...
by cracking of
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...
s. Approximately 400,000 tonnes were produced by this method in 1983. Its presence in ethylene is usually undesirable because of its explosive character and its ability to poison
Ziegler–Natta catalyst A Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, is a catalyst used in the synthesis of polymers of 1-alkenes ( alpha-olefins). Two broad classes of Ziegler–Natta catalysts are employed, distinguished by their solubility: * ...
s. It is selectively hydrogenated into
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...
, usually using PdAg catalysts. Until the 1950s, when
oil An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) & lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturated ...
supplanted
coal Coal is a combustible black or brownish-black sedimentary rock, formed as rock strata called coal seams. Coal is mostly carbon with variable amounts of other elements, chiefly hydrogen, sulfur, oxygen, and nitrogen. Coal is formed when dea ...
as the chief source of reduced carbon, acetylene (and the aromatic fraction from
coal tar Coal tar is a thick dark liquid which is a by-product of the production of coke and coal gas from coal. It is a type of creosote. It has both medical and industrial uses. Medicinally it is a topical medication applied to skin to treat psoriasi ...
) was the main source of organic chemicals in the chemical industry. It was prepared by the
hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
of
calcium carbide Calcium carbide, also known as calcium acetylide, is a chemical compound with the chemical formula of Ca C2. Its main use industrially is in the production of acetylene and calcium cyanamide. The pure material is colorless, while pieces of te ...
, a reaction discovered by
Friedrich Wöhler Friedrich Wöhler () FRS(For) HonFRSE (31 July 180023 September 1882) was a German chemist known for his work in inorganic chemistry, being the first to isolate the chemical elements beryllium and yttrium in pure metallic form. He was the firs ...
in 1862 and still familiar to students: : CaC2 + 2H2O -> Ca(OH)2 + C2H_ Calcium carbide production requires extremely high temperatures, ~2000 °C, necessitating the use of an
electric arc furnace An electric arc furnace (EAF) is a furnace that heats material by means of an electric arc. Industrial arc furnaces range in size from small units of approximately one-tonne capacity (used in foundries for producing cast iron products) up to ab ...
. In the US, this process was an important part of the late-19th century revolution in chemistry enabled by the massive
hydroelectric power Hydroelectricity, or hydroelectric power, is electricity generated from hydropower (water power). Hydropower supplies one sixth of the world's electricity, almost 4500 TWh in 2020, which is more than all other renewable sources combined an ...
project at
Niagara Falls Niagara Falls () is a group of three waterfalls at the southern end of Niagara Gorge, spanning the border between the province of Ontario in Canada and the state of New York in the United States. The largest of the three is Horseshoe Falls, ...
.


Bonding

In terms of valence bond theory, in each carbon atom the 2s orbital hybridizes with one 2p orbital thus forming an sp hybrid. The other two 2p orbitals remain unhybridized. The two ends of the two sp hybrid
orbital overlap In chemical bonds, an orbital overlap is the concentration of orbitals on adjacent atoms in the same regions of space. Orbital overlap can lead to bond formation. Linus Pauling explained the importance of orbital overlap in the molecular bond ang ...
to form a strong σ valence bond between the carbons, while on each of the other two ends hydrogen atoms attach also by σ bonds. The two unchanged 2p orbitals form a pair of weaker π bonds. Since acetylene is a linear symmetrical molecule, it possesses the D∞h point group.


Physical properties


Changes of state

At atmospheric pressure, acetylene cannot exist as a liquid and does not have a melting point. The
triple point In thermodynamics, the triple point of a substance is the temperature and pressure at which the three phases (gas, liquid, and solid) of that substance coexist in thermodynamic equilibrium.. It is that temperature and pressure at which the subli ...
on the phase diagram corresponds to the melting point (−80.8 °C) at the minimal pressure at which liquid acetylene can exist (1.27 atm). At temperatures below the triple point, solid acetylene can change directly to the
vapour In physics, a vapor (American English) or vapour (British English and Canadian English; see spelling differences) is a substance in the gas phase at a temperature lower than its critical temperature,R. H. Petrucci, W. S. Harwood, and F. G. Herr ...
(gas) by sublimation. The sublimation point at atmospheric pressure is −84.0 °C.


Other

At room temperature, the solubility of acetylene in
acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...
is 27.9 g per kg. For the same amount of
dimethylformamide Dimethylformamide is an organic compound with the formula ( CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the maj ...
(DMF), the solubility is 51 g. At 20.26 bar, the solubility increases to 689.0 and 628.0 g for acetone and DMF, respectively. These solvents are used in pressurized gas cylinders.


Applications


Welding

Approximately 20% of acetylene is supplied by the industrial gases industry for
oxyacetylene Principle of burn cutting Oxy-fuel welding (commonly called oxyacetylene welding, oxy welding, or gas welding in the United States) and oxy-fuel cutting are processes that use fuel gases (or liquid fuels such as gasoline or petrol, diesel, ...
gas welding Principle of burn cutting Oxy-fuel welding (commonly called oxyacetylene welding, oxy welding, or gas welding in the United States) and oxy-fuel cutting are processes that use fuel gases (or liquid fuels such as gasoline or petrol, diesel, ...
and
cutting Cutting is the separation or opening of a physical object, into two or more portions, through the application of an acutely directed force. Implements commonly used for wikt:cut, cutting are the knife and saw, or in medicine and science the scal ...
due to the high temperature of the flame. Combustion of acetylene with oxygen produces a flame of over , releasing 11.8  kJ/g. Oxyacetylene is the hottest burning common fuel gas. Acetylene is the third-hottest natural chemical flame after
dicyanoacetylene Dicyanoacetylene, also called carbon subnitride or but-2-ynedinitrile (IUPAC), is a compound of carbon and nitrogen with chemical formula . It has a linear molecular structure, (often abbreviated as ), with alternating triple and single covalen ...
's and
cyanogen Cyanogen is the chemical compound with the formula ( C N)2. It is a colorless and highly toxic gas with a pungent odor. The molecule is a pseudohalogen. Cyanogen molecules consist of two CN groups – analogous to diatomic halogen molecule ...
at .
Oxy-acetylene welding Principle of burn cutting Oxy-fuel welding (commonly called oxyacetylene welding, oxy welding, or gas welding in the United States) and oxy-fuel cutting are processes that use fuel gases (or liquid fuels such as gasoline or petrol, diesel, ...
was a popular welding process in previous decades. The development and advantages of arc-based welding processes have made oxy-fuel welding nearly extinct for many applications. Acetylene usage for welding has dropped significantly. On the other hand, oxy-acetylene welding ''equipment'' is quite versatile – not only because the torch is preferred for some sorts of iron or steel welding (as in certain artistic applications), but also because it lends itself easily to brazing, braze-welding, metal heating (for annealing or tempering, bending or forming), the loosening of corroded nuts and bolts, and other applications.
Bell Canada Bell Canada (commonly referred to as Bell) is a Canadian telecommunications company headquartered at 1 Carrefour Alexander-Graham-Bell in the borough of Verdun in Montreal, Quebec, Canada. It is an ILEC (incumbent local exchange carrier) in t ...
cable-repair technicians still use portable acetylene-fuelled torch kits as a
soldering Soldering (; ) is a process in which two or more items are joined by melting and putting a filler metal (solder) into the joint, the filler metal having a lower melting point than the adjoining metal. Unlike welding, soldering does not involv ...
tool for sealing lead sleeve splices in
manhole A manhole (utility hole, maintenance hole, or sewer hole) is an opening to a confined space such as a shaft, utility vault, or large vessel. Manholes are often used as an access point for an underground public utility, allowing inspection, m ...
s and in some aerial locations. Oxyacetylene welding may also be used in areas where electricity is not readily accessible. Oxyacetylene cutting is used in many metal fabrication shops. For use in welding and cutting, the working pressures must be controlled by a regulator, since above , if subjected to a shockwave (caused, for example, by a flashback), acetylene
decompose Decomposition or rot is the process by which dead organic substances are broken down into simpler organic or inorganic matter such as carbon dioxide, water, simple sugars and mineral salts. The process is a part of the nutrient cycle and is ...
s explosively into
hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...
and
carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...
.


Portable lighting

Acetylene combustion produces a strong, bright light and the ubiquity of carbide lamps drove much acetylene commercialization in the early 20th century. Common applications included coastal
lighthouses A lighthouse is a tower, building, or other type of physical structure designed to emit light from a system of lamps and lenses and to serve as a beacon for navigational aid, for maritime pilots at sea or on inland waterways. Lighthouses mark ...
,
street lights A street light, light pole, lamp pole, lamppost, street lamp, light standard, or lamp standard is a raised source of light on the edge of a road or path. Similar lights may be found on a railway platform. When urban electric power distribution ...
, and
automobile A car or automobile is a motor vehicle with Wheel, wheels. Most definitions of ''cars'' say that they run primarily on roads, Car seat, seat one to eight people, have four wheels, and mainly transport private transport#Personal transport, pe ...
and
mining Mining is the extraction of valuable minerals or other geological materials from the Earth, usually from an ore body, lode, vein, seam, reef, or placer deposit. The exploitation of these deposits for raw material is based on the economic via ...
headlamps A headlamp is a lamp attached to the front of a vehicle to illuminate the road ahead. Headlamps are also often called headlights, but in the most precise usage, ''headlamp'' is the term for the device itself and ''headlight'' is the term for ...
. In most of these applications, direct combustion is a
fire hazard Fire safety is the set of practices intended to reduce the destruction caused by fire. Fire safety measures include those that are intended to prevent the ignition of an uncontrolled fire and those that are used to limit the development and ef ...
, and so acetylene has been replaced, first by
incandescent lighting An incandescent light bulb, incandescent lamp or incandescent light globe is an electric light with a wire filament heated until it glows. The filament is enclosed in a glass bulb with a vacuum or inert gas to protect the filament from oxid ...
and many years later by low-power/high-lumen LEDs. Nevertheless, acetylene lamps remain in limited use in remote or otherwise inaccessible areas and in countries with a weak or unreliable central
electric grid An electrical grid is an interconnected network for electricity delivery from producers to consumers. Electrical grids vary in size and can cover whole countries or continents. It consists of:Kaplan, S. M. (2009). Smart Grid. Electrical Power ...
.


Plastics and acrylic acid derivatives

Acetylene can be semihydrogenated to
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...
, providing a feedstock for a variety of
polyethylene Polyethylene or polythene (abbreviated PE; IUPAC name polyethene or poly(methylene)) is the most commonly produced plastic. It is a polymer, primarily used for packaging ( plastic bags, plastic films, geomembranes and containers including bo ...
plastics. Another major application of acetylene, especially in China is its conversion to
acrylic acid Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a ...
derivatives The derivative of a function is the rate of change of the function's output relative to its input value. Derivative may also refer to: In mathematics and economics * Brzozowski derivative in the theory of formal languages * Formal derivative, an ...
. These derivatives form products such as
acrylic fiber Acrylic fibers are synthetic fibers made from a polymer (polyacrylonitrile) with an average molecular weight of ~100,000, about 1900 monomer units. For a fiber to be called "acrylic" in the US, the polymer must contain at least 85% acrylonitr ...
s,
glass Glass is a non-crystalline, often transparent, amorphous solid that has widespread practical, technological, and decorative use in, for example, window panes, tableware, and optics. Glass is most often formed by rapid cooling (quenching) of ...
es,
paint Paint is any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is most commonly used to protect, color, or provide texture. Paint can be made in many ...
s,
resin In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on natu ...
s, and
polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...
s. Except in China, use of acetylene as a chemical feedstock has declined by 70% from 1965 to 2007 owing to cost and environmental considerations.


Niche applications

In 1881, the Russian chemist Mikhail Kucherov described the
hydration Hydration may refer to: * Hydrate, a substance that contains water * Hydration enthalpy, energy released through hydrating a substance * Hydration reaction, a chemical addition reaction where a hydroxyl group and proton are added to a compound * ...
of acetylene to
acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the mos ...
using catalysts such as
mercury(II) bromide Mercury(II) bromide or mercuric bromide is an inorganic compound with the formula HgBr2. This white solid is a laboratory reagent. Like all mercury salts, it is highly toxic. Preparation Mercury(II) bromide can be produced by reaction of metalli ...
. Before the advent of the
Wacker process The Wacker process or the Hoechst-Wacker process (named after the chemical companies of the same name) refers to the oxidation of ethylene to acetaldehyde in the presence of palladium(II) chloride as the catalyst. This chemical reaction was one of ...
, this reaction was conducted on an industrial scale. The
polymerization In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer, monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are ...
of acetylene with
Ziegler–Natta catalyst A Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, is a catalyst used in the synthesis of polymers of 1-alkenes ( alpha-olefins). Two broad classes of Ziegler–Natta catalysts are employed, distinguished by their solubility: * ...
s produces
polyacetylene Polyacetylene (IUPAC name: polyethyne) usually refers to an organic polymer with the repeating unit . The name refers to its conceptual construction from polymerization of acetylene to give a chain with repeating olefin groups. This compound i ...
films. Polyacetylene, a chain of CH centres with alternating single and double bonds, was one of the first discovered
organic semiconductor Organic semiconductors are solids whose building blocks are pi-bonded molecules or polymers made up by carbon and hydrogen atoms and – at times – heteroatoms such as nitrogen, sulfur and oxygen. They exist in the form of molecular crystals or ...
s. Its reaction with
iodine Iodine is a chemical element with the symbol I and atomic number 53. The heaviest of the stable halogens, it exists as a semi-lustrous, non-metallic solid at standard conditions that melts to form a deep violet liquid at , and boils to a vi ...
produces a highly electrically conducting material. Although such materials are not useful, these discoveries led to the developments of
organic semiconductor Organic semiconductors are solids whose building blocks are pi-bonded molecules or polymers made up by carbon and hydrogen atoms and – at times – heteroatoms such as nitrogen, sulfur and oxygen. They exist in the form of molecular crystals or ...
s, as recognized by the
Nobel Prize in Chemistry ) , image = Nobel Prize.png , alt = A golden medallion with an embossed image of a bearded man facing left in profile. To the left of the man is the text "ALFR•" then "NOBEL", and on the right, the text (smaller) "NAT•" then "M ...
in 2000 to Alan J. Heeger,
Alan G MacDiarmid Alan Graham MacDiarmid, ONZ FRS (14 April 1927 – 7 February 2007) was a New Zealand-born American chemist, and one of three recipients of the Nobel Prize for Chemistry in 2000. Early life and education MacDiarmid was born in Masterton, N ...
, and
Hideki Shirakawa is a Japanese chemist, engineer, and Professor Emeritus at the University of Tsukuba and Zhejiang University. He is best known for his discovery of conductive polymers. He was co-recipient of the 2000 Nobel Prize in Chemistry jointly with Alan Ma ...
. In the 1920s, pure acetylene was experimentally used as an
inhalation anesthetic An inhalational anesthetic is a chemical compound possessing general anesthetic properties that can be delivered via inhalation. They are administered through a face mask, laryngeal mask airway or tracheal tube connected to an anesthetic vapori ...
. Acetylene is sometimes used for
carburization Carburising, carburizing (chiefly American English), or carburisation is a heat treatment process in which iron or steel absorbs carbon while the metal is heated in the presence of a carbon-bearing material, such as charcoal or carbon monoxide. ...
(that is, hardening) of steel when the object is too large to fit into a furnace. Acetylene is used to volatilize carbon in
radiocarbon dating Radiocarbon dating (also referred to as carbon dating or carbon-14 dating) is a method for determining the age of an object containing organic material by using the properties of radiocarbon, a radioactive isotope of carbon. The method was dev ...
. The carbonaceous material in an archeological sample is treated with
lithium Lithium (from el, λίθος, lithos, lit=stone) is a chemical element with the symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard conditions, it is the least dense metal and the least dense solid el ...
metal in a small specialized research furnace to form
lithium carbide Lithium carbide, , often known as dilithium acetylide, is a chemical compound of lithium and carbon, an acetylide. It is an intermediate compound produced during radiocarbon dating procedures. is one of an extensive range of lithium-carbon compo ...
(also known as lithium acetylide). The carbide can then be reacted with water, as usual, to form acetylene gas to feed into a
mass spectrometer Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a ''mass spectrum'', a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is used ...
to measure the isotopic ratio of carbon-14 to carbon-12.


Natural occurrence

The energy richness of the C≡C triple bond and the rather high solubility of acetylene in water make it a suitable substrate for bacteria, provided an adequate source is available. A number of bacteria living on acetylene have been identified. The
enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products. A ...
acetylene hydratase Acetylene hydratase (, AH) is a bacterial enzyme, originally discovered in the anaerobic microorganism ''Pelobactor acetylenicus'', that catalyzes the non-redox hydration of acetylene to form acetaldehyde. :C2H2 + H2O → CH3CHO The mechanism is ...
catalyzes the hydration of acetylene to give
acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the mos ...
: :C2H2 + H2O -> CH3CHO Acetylene is a moderately common chemical in the universe, often associated with the atmospheres of
gas giant A gas giant is a giant planet composed mainly of hydrogen and helium. Gas giants are also called failed stars because they contain the same basic elements as a star. Jupiter and Saturn are the gas giants of the Solar System. The term "gas giant" ...
s. One curious discovery of acetylene is on
Enceladus Enceladus is the sixth-largest moon of Saturn (19th largest in the Solar System). It is about in diameter, about a tenth of that of Saturn's largest moon, Titan. Enceladus is mostly covered by fresh, clean ice, making it one of the most refle ...
, a moon of
Saturn Saturn is the sixth planet from the Sun and the second-largest in the Solar System, after Jupiter. It is a gas giant with an average radius of about nine and a half times that of Earth. It has only one-eighth the average density of Earth; h ...
. Natural acetylene is believed to form from
catalytic Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...
decomposition of long-chain hydrocarbons at temperatures of and above. Since such temperatures are highly unlikely on such a small distant body, this discovery is potentially suggestive of catalytic reactions within that moon, making it a promising site to search for prebiotic chemistry.


Reactions


Vinylation reactions

In vinylation reactions, H−X compounds add across the triple bond.
Alcohols In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl () functional group bound to a saturated carbon atom. The term ''alcohol'' originally referred to the primary alcohol ethanol (ethyl alcohol), which is ...
and
phenols In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (— O H) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, . Phenolic compounds are c ...
add to acetylene to give vinyl ethers.
Thiols In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl grou ...
give vinyl thioethers. Similarly,
vinylpyrrolidone ''N''-Vinylpyrrolidone (NVP) is an organic compound consisting of a 5-membered lactam linked to a vinyl group. It is a colorless liquid although commercial samples can appear yellowish. It is produced industrially by vinylation of 2-pyrrolidon ...
and vinylcarbazole are produced industrially by vinylation of 2-pyrrolidone and
carbazole Carbazole is an aromatic heterocyclic organic compound. It has a tricyclic structure, consisting of two six-membered benzene rings fused on either side of a five-membered nitrogen-containing ring. The compound's structure is based on the indole str ...
. : The hydration of acetylene is a vinylation reaction, but the resulting vinyl alcohol isomerizes to
acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the mos ...
. The reaction is catalyzed by mercury salts. This reaction once was the dominant technology for acetaldehyde production, but it has been displaced by the
Wacker process The Wacker process or the Hoechst-Wacker process (named after the chemical companies of the same name) refers to the oxidation of ethylene to acetaldehyde in the presence of palladium(II) chloride as the catalyst. This chemical reaction was one of ...
, which affords acetaldehyde by oxidation of
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...
, a cheaper feedstock. A similar situation applies to the conversion of acetylene to the valuable
vinyl chloride Vinyl chloride is an organochloride with the formula H2C=CHCl. It is also called vinyl chloride monomer (VCM) or chloroethene. This colorless compound is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride (PVC ...
by
hydrochlorination A hydrohalogenation reaction is the electrophilic addition of hydrohalic acids like hydrogen chloride or hydrogen bromide to alkenes to yield the corresponding haloalkanes. : If the two carbon atoms at the double bond are linked to a different n ...
vs the
oxychlorination In organic chemistry, oxychlorination is a process for making C-Cl bonds. In contrast with direct use of Cl2, oxychlorination uses hydrogen chloride in combination with oxygen.{{Ullmann, author=M. Rossberg , display-authors=et al., title=Chlorinated ...
of ethylene.


Ethynylation

Acetylene adds to
aldehydes In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group ...
and
ketones In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bon ...
to form α-ethynyl alcohols: : The reaction with
formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...
is used industrially in the production of butynediol, forming
propargyl alcohol Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the chemical formula, formula C3H4O. It is the simplest stable Alcohol (chemistry), alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid t ...
as the by-product.
Copper acetylide Copper(I) acetylide, or cuprous acetylide, is a chemical compound with the formula Cu2 C2. Although never characterized by X-ray crystallography, the material has been claimed at least since 1856. One form is claimed to be a mono hydrate with fo ...
is used as the catalyst. Because halogens add across the triple bond, the substituted acetylenes difluoroacetylene,
dichloroacetylene Dichloroacetylene (DCA) is an organochlorine compound with the formula C2Cl2. It is a colorless, explosive liquid that has a sweet and "disagreeable" odor. Production Dichloroacetylene was first synthesized in 1930. Ether solutions of dichloroac ...
,
dibromoacetylene Dibromoacetylene is a molecular chemical compound containing acetylene, with its hydrogen substituted by bromine. Production Dibromoacetylene can be made by reacting 1,1,2-tribromoethylene with potassium hydroxide. This method has a danger of cau ...
, and
diiodoacetylene Diiodoacetylene is the organoiodine compound with the formula C2I2. It is a white, volatile solid that dissolves in organic solvents. It is prepared by iodination of trimethylsilylacetylene. Although samples explode above 80 °C, diiodoacet ...
cannot be made directly from acetylene. A common workaround is to dehydrate vinyl dihaloethenols.


Carbonylation

Walter Reppe Walter Julius Reppe (29 July 1892 in Göringen – 26 July 1969 in Heidelberg) was a German chemist. He is notable for his contributions to the chemistry of acetylene. Education and career Walter Reppe began his study of the natural sciences ...
discovered that in the presence of
catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...
s, acetylene reacts to give a wide range of industrially significant chemicals. : : With
carbon monoxide Carbon monoxide (chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simple ...
, acetylene reacts to give
acrylic acid Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a ...
, or acrylic esters, which can be used to produce
acrylic glass Poly(methyl methacrylate) (PMMA) belongs to a group of materials called engineering plastics. It is a transparent thermoplastic. PMMA is also known as acrylic, acrylic glass, as well as by the trade names and brands Crylux, Plexiglas, Acrylite, ...
.


Organometallic chemistry

Acetylene and its derivatives (2-butyne, diphenylacetylene, etc.) form complexes with transition metals. Its bonding to the metal is somewhat similar to that of ethylene complexes. These complexes are intermediates in many catalytic reactions such as
alkyne trimerisation In organic chemistry, an alkyne trimerisation is a +2+2nbsp; cycloaddition reaction in which three alkyne units () react to form a benzene ring. The reaction requires a metal catalyst. The process is of historic interest as well as being applic ...
to benzene, tetramerization to
cyclooctatetraene 1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane, with the formula C8H8. It is also known as nnulene. This polyunsaturated hydrocarbon is a colorless to light yellow flammable liquid at room temperature. Because of ...
, and carbonylation to
hydroquinone Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''para'' ...
: : : :Fe(CO)5 + 4 C2H2 + 2 H2O -> 2 C6H4(OH)2 + FeCO3 at basic conditions (50–, 20–). In the presence of certain transition metals, alkynes undergo
alkyne metathesis Alkyne metathesis is an organic reaction that entails the redistribution of alkyne chemical bonds. The reaction requires metal catalysts. Mechanistic studies show that the conversion proceeds via the intermediacy of metal alkylidyne complexes. T ...
. Metal
acetylide In organometallic chemistry, acetylide refers to chemical compounds with the chemical formulas and , where M is a metal. The term is used loosely and can refer to substituted acetylides having the general structure (where R is an organic side c ...
s, species of the formula , are also common.
Copper(I) acetylide Copper(I) acetylide, or cuprous acetylide, is a chemical compound with the formula Cu2 C2. Although never characterized by X-ray crystallography, the material has been claimed at least since 1856. One form is claimed to be a monohydrate with for ...
and
silver acetylide Silver acetylide is an inorganic chemical compound with the formula Ag2C2, a metal acetylide. The compound can be regarded as a salt of the weak acid, acetylene. The salt's anion consists of two carbon atoms linked by a triple bond. The alternate ...
can be formed in
aqueous An aqueous solution is a solution in which the solvent is water. It is mostly shown in chemical equations by appending (aq) to the relevant chemical formula. For example, a solution of table salt, or sodium chloride (NaCl), in water would be rep ...
solutions with ease due to a poor
solubility equilibrium Solubility equilibrium is a type of dynamic equilibrium that exists when a chemical compound in the solid state is in chemical equilibrium with a solution of that compound. The solid may dissolve unchanged, with dissociation, or with chemical reacti ...
.


Acid-base reactions

Acetylene has a p''K''a of 25, acetylene can be
deprotonated Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H+) from a Brønsted–Lowry acid in an acid–base reaction.Henry Jakubowski, Biochemistry Online Chapter 2A3, https://employees.csbsju.edu ...
by a
superbase A superbase is a compound that has a particularly high affinity for protons. Superbases are of theoretical interest and potentially valuable in organic synthesis. Superbases have been described and used since the 1850s.''Superbases for Organic ...
to form an
acetylide In organometallic chemistry, acetylide refers to chemical compounds with the chemical formulas and , where M is a metal. The term is used loosely and can refer to substituted acetylides having the general structure (where R is an organic side c ...
: : HC#CH + RM -> RH + HC#CM Various
organometallic Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and so ...
and
inorganic In chemistry, an inorganic compound is typically a chemical compound that lacks carbon–hydrogen bonds, that is, a compound that is not an organic compound. The study of inorganic compounds is a subfield of chemistry known as '' inorganic chemist ...
reagents are effective.


Safety and handling

Acetylene is not especially toxic, but when generated from
calcium carbide Calcium carbide, also known as calcium acetylide, is a chemical compound with the chemical formula of Ca C2. Its main use industrially is in the production of acetylene and calcium cyanamide. The pure material is colorless, while pieces of te ...
, it can contain toxic impurities such as traces of
phosphine Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting ...
and
arsine Arsine (IUPAC name: arsane) is an inorganic compound with the formula As H3. This flammable, pyrophoric, and highly toxic pnictogen hydride gas is one of the simplest compounds of arsenic. Despite its lethality, it finds some applications in ...
, which give it a distinct
garlic Garlic (''Allium sativum'') is a species of bulbous flowering plant in the genus ''Allium''. Its close relatives include the onion, shallot, leek, chive, Allium fistulosum, Welsh onion and Allium chinense, Chinese onion. It is native to South A ...
-like smell. It is also highly flammable, as are most light hydrocarbons, hence its use in welding. Its most singular hazard is associated with its intrinsic instability, especially when it is pressurized: under certain conditions acetylene can react in an
exothermic In thermodynamics, an exothermic process () is a thermodynamic process or reaction that releases energy from the system to its surroundings, usually in the form of heat, but also in a form of light (e.g. a spark, flame, or flash), electricity (e ...
addition-type reaction to form a number of products, typically
benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
and/or
vinylacetylene Vinylacetylene is the organic compound with the formula C4H4. The colourless gas was once used in the polymer industry. It is composed of both alkyne and alkene groups and is the simplest enyne. Vinylacetylene is extremely dangerous because in ...
, possibly in addition to
carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...
and
hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...
. Consequently, acetylene, if initiated by intense heat or a shockwave, can decompose explosively if the absolute pressure of the gas exceeds about . Most regulators and pressure gauges on equipment report
gauge pressure Pressure measurement is the measurement of an applied force by a fluid (liquid or gas) on a surface. Pressure is typically measured in units of force per unit of surface area. Many techniques have been developed for the measurement of pressur ...
, and the safe limit for acetylene therefore is 101 kPagage, or 15 psig. It is therefore supplied and stored dissolved in
acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...
or
dimethylformamide Dimethylformamide is an organic compound with the formula ( CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the maj ...
(DMF), contained in a
gas cylinder A gas cylinder is a pressure vessel for storage and containment of gases at above atmospheric pressure. High-pressure gas cylinders are also called ''bottles''. Inside the cylinder the stored contents may be in a state of compressed gas, vapor ...
with a porous filling (
Agamassan Agamassan is a porous substrate used to safely absorb acetylene and thus allow the transport, storage and commercial use of the otherwise unstable gas. It was developed and patented by the Swedish Nobel Laureate and industrialist Gustaf Dalén. ...
), which renders it safe to transport and use, given proper handling. Acetylene cylinders should be used in the upright position to avoid withdrawing acetone during use. Information on safe storage of acetylene in upright cylinders is provided by the OSHA, Compressed Gas Association, United States Mine Safety and Health Administration (MSHA), EIGA, and other agencies.
Copper Copper is a chemical element with the symbol Cu (from la, cuprum) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pinkis ...
catalyses the decomposition of acetylene, and as a result acetylene should not be transported in copper pipes. Cylinders should be stored in an area segregated from oxidizers to avoid exacerbated reaction in case of fire/leakage. Acetylene cylinders should not be stored in confined spaces, enclosed vehicles, garages, and buildings, to avoid unintended leakage leading to explosive atmosphere. In the US, National Electric Code (NEC) requires consideration for hazardous areas including those where acetylene may be released during accidents or leaks. Consideration may include electrical classification and use of listed Group A electrical components in USA. Further information on determining the areas requiring special consideration is in NFPA 497. In Europe, ATEX also requires consideration for hazardous areas where flammable gases may be released during accidents or leaks.


References


External links


Acetylene Production Plant and Detailed Process

Acetylene at Chemistry Comes Alive!
*
Movie explaining acetylene formation from calcium carbide and the explosive limits forming fire hazards
at ''
The Periodic Table of Videos ''Periodic Videos'' (also known as ''The Periodic Table of Videos'') is a video project and YouTube channel on chemistry. It consists of a series of videos about chemical elements and the periodic table, with additional videos on other topics i ...
'' (University of Nottingham)
CDC – NIOSH Pocket Guide to Chemical Hazards – Acetylene
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