Acetylene

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Acetylene
Acetylene-CRC-IR-dimensions-2D.svg
Acetylene-CRC-IR-3D-balls.png
Acetylene-3D-vdW.png
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Names
Preferred IUPAC name
Acetylene [1]
Systematic IUPAC name
Ethyne [2]
Identifiers
3D model (JSmol)
906677
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.743 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-816-9
210
KEGG
PubChem CID
RTECS number
  • AO9600000
UNII
UN number 1001 (dissolved)
3138 (in mixture with ethylene and propylene)
  • InChI=1S/C2H2/c1-2/h1-2H Yes check.svgY
    Key: HSFWRNGVRCDJHI-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2H2/c1-2/h1-2H
    Key: HSFWRNGVRCDJHI-UHFFFAOYAY
  • C#C
Properties
C2H2
Molar mass 26.038 g·mol−1
AppearanceColorless gas
Odor Odorless
Density 1.1772 g/L = 1.1772 kg/m3 (0 °C, 101.3 kPa) [3]
Melting point −80.8 °C (−113.4 °F; 192.3 K) Triple point at 1.27 atm
−84 °C; −119 °F; 189 K (1 atm)
slightly soluble
Solubility slightly soluble in alcohol
soluble in acetone, benzene
Vapor pressure 44.2 atm (20 °C) [4]
Acidity (pKa)25 [5]
Conjugate acid Ethynium
−20.8×10−6 cm3/mol [6]
Thermal conductivity 21.4 mW·m−1·K−1 (300 K) [6]
Structure
Linear
Thermochemistry [6]
44.036 J·mol−1·K−1
Std molar
entropy
(S298)
200.927 J·mol−1·K−1
227.400 kJ·mol−1
209.879 kJ·mol−1
1300 kJ·mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Danger
H220, H336
P202, P210, P233, P261, P271, P304, P312, P340, P377, P381, P403, P405, P501
NFPA 704 (fire diamond)
1
4
3
300 °C (572 °F; 573 K)
Explosive limits 2.5–100%
NIOSH (US health exposure limits):
PEL (Permissible)
none [4]
REL (Recommended)
C 2500 ppm (2662 mg/m3) [4]
IDLH (Immediate danger)
N.D. [4]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Acetylene (systematic name: ethyne) is the chemical compound with the formula C2H2 and structure H−C≡C−H. It is a hydrocarbon and the simplest alkyne. [7] 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. [8] Pure acetylene is odorless, but commercial grades usually have a marked odor due to impurities such as divinyl sulfide and phosphine. [8] [9]

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°. [10]

Discovery

Acetylene was discovered in 1836 by Edmund Davy, who identified it as a "new carburet of hydrogen". [11] [12] It was an accidental discovery while attempting to isolate potassium metal. By heating potassium carbonate with carbon at very high temperatures, he produced a residue of what is now known as potassium carbide, (K2C2), which reacted with water to release the new gas. It was rediscovered in 1860 by French chemist Marcellin Berthelot, who coined the name acétylène. [13] 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). [14] 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 that 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. [15] [16]

Preparation

Since the 1950s, acetylene has mainly been manufactured by the partial combustion of methane. [8] [17] [18] It is a recovered side product in production of ethylene by cracking of hydrocarbons. Approximately 400,000 tonnes were produced by this method in 1983. [8] 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 PdAg catalysts. [19]

Acetylene factory with annual capacity of 90,000 tons, commissioned in 2020 by BASF. BASF Nsw.jpg
Acetylene factory with annual capacity of 90,000 tons, commissioned in 2020 by BASF.

Until the 1950s, when oil supplanted coal as the chief source of reduced 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 [20] and still familiar to students:

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-19th century revolution in chemistry enabled by the massive hydroelectric power project at Niagara Falls. [21]

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 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. [22]

Since acetylene is a linear symmetrical molecule, it possesses the D∞h point group. [23]

Physical properties

Changes of state

At atmospheric pressure, acetylene cannot exist as a liquid and does not have a melting point. The triple point 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 (gas) by sublimation. The sublimation point at atmospheric pressure is −84.0 °C. [24]

Other

At room temperature, the solubility of acetylene in acetone is 27.9 g per kg. For the same amount of dimethylformamide (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. [25]

Applications

Welding

Approximately 20% of acetylene is supplied by the industrial gases industry for oxyacetylene gas welding and cutting due to the high temperature of the flame. Combustion of acetylene with oxygen produces a flame of over 3,600 K (3,330 °C; 6,020 °F), releasing 11.8  kJ/g. Oxyacetylene is the hottest burning common fuel gas. [26] Acetylene is the third-hottest natural chemical flame after dicyanoacetylene's 5,260 K (4,990 °C; 9,010 °F) and cyanogen at 4,798 K (4,525 °C; 8,177 °F). Oxy-acetylene welding 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 cable-repair technicians still use portable acetylene-fuelled torch kits as a soldering tool for sealing lead sleeve splices in manholes 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 15 psi (100 kPa), if subjected to a shockwave (caused, for example, by a flashback), acetylene decomposes explosively into hydrogen and carbon. [27]

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

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, [28] street lights, [29] and automobile [30] and mining headlamps. [31] In most of these applications, direct combustion is a fire hazard, and so acetylene has been replaced, first by incandescent lighting 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. [31]

Plastics and acrylic acid derivatives

Acetylene can be semihydrogenated to ethylene, providing a feedstock for a variety of polyethylene plastics. Another major application of acetylene, especially in China is its conversion to acrylic acid derivatives. [8] These derivatives form products such as acrylic fibers, glasses, paints, resins, and polymers. [32]

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 [33] 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. [34]

The polymerization of acetylene with Ziegler–Natta catalysts produces polyacetylene films. Polyacetylene, a chain of CH centres with alternating single and double bonds, was one of the 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. [8]

In the 1920s, pure acetylene was experimentally used as an inhalation anesthetic. [35]

Acetylene is sometimes used for carburization (that is, hardening) of steel when the object is too large to fit into a furnace. [36]

Acetylene is used to volatilize carbon in radiocarbon dating. The carbonaceous material in an archeological sample is treated 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 feed into a mass spectrometer to measure the isotopic ratio of carbon-14 to carbon-12. [37]

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. [38] A number of bacteria living on acetylene have been identified. The enzyme acetylene hydratase catalyzes the hydration of acetylene to give acetaldehyde: [39]

Acetylene is a moderately common chemical in the universe, often associated with the atmospheres of gas giants. [40] One curious discovery of acetylene is on Enceladus, a moon of Saturn. Natural acetylene is believed to form from catalytic decomposition of long-chain hydrocarbons at temperatures of 1,700 K (1,430 °C; 2,600 °F) 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. [41] [42]

Reactions

Vinylation reactions

In 'vinylation reactions, H−X compounds add across the triple bond. Alcohols and phenols add to acetylene to give vinyl ethers. Thiols give vinyl thioethers. Similarly, vinylpyrrolidone and vinylcarbazole are produced industrially by vinylation of 2-pyrrolidone and carbazole. [25] [8]

Reppe-chemnistry-vinylization.png

The hydration of acetylene is a vinylation reaction, but the resulting vinyl alcohol isomerizes to acetaldehyde. 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, which affords acetaldehyde by oxidation of ethylene, a cheaper feedstock. A similar situation applies to the conversion of acetylene to the valuable vinyl chloride by hydrochlorination vs the oxychlorination of ethylene.

Vinyl acetate is used instead of acetylene for some vinylations, which are more accurately described as transvinylations. [43] Higher esters of vinyl acetate have been used in the synthesis of vinyl formate.

Ethynylation

Acetylene adds to aldehydes and ketones to form α-ethynyl alcohols: [8]

Reppe-chemistry-endiol-V1.svg

The reaction with formaldehyde is used industrially in the production of butynediol, forming propargyl alcohol as the by-product. Copper acetylide is used as the catalyst. [44] [45]

Because halogens add across the triple bond, the substituted acetylenes difluoroacetylene, dichloroacetylene, dibromoacetylene, and diiodoacetylene cannot be made directly from acetylene. A common workaround is to dehydrate vinyl dihaloethenols. [46]

Carbonylation

Walter Reppe discovered that in the presence of catalysts, acetylene reacts to give a wide range of industrially significant chemicals. [8] [47] [48]

Reppe-chemistry-carbonmonoxide-01.png
Reppe-chemistry-carbonmonoxide-02.png

With carbon monoxide, acetylene reacts to give acrylic acid, or acrylic esters, which can be used to produce acrylic glass. [32]

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 to benzene, tetramerization to cyclooctatetraene, [8] and carbonylation to hydroquinone: [47]

Reppe-chemistry-benzene.png
Reppe-chemistry-cyclooctatetraene.png


at basic conditions (50–80 °C, 20–25 atm).

In the presence of certain transition metals, alkynes undergo alkyne metathesis.

Metal acetylides, species of the formula LnM−C2R, are also common. Copper(I) acetylide and silver acetylide can be formed in aqueous solutions with ease due to a poor solubility equilibrium. [49]

Acid-base reactions

Acetylene has a pKa of 25, acetylene can be deprotonated by a superbase to form an acetylide: [49]

Various organometallic [50] and inorganic [51] reagents are effective.

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, which give it a distinct garlic-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 addition-type reaction to form a number of products, typically benzene and/or vinylacetylene, possibly in addition to carbon and hydrogen.[ citation needed ] Consequently, acetylene, if initiated by intense heat or a shockwave, can decompose explosively if the absolute pressure of the gas exceeds about 200 kilopascals (29 psi). Most regulators and pressure gauges on equipment report gauge pressure, and the safe limit for acetylene therefore is 101 kPagage, or 15 psig. [52] [53] It is therefore supplied and stored dissolved in acetone or dimethylformamide (DMF), [53] [54] [55] contained in a gas cylinder with a porous filling (Agamassan), 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. [56]

Information on safe storage of acetylene in upright cylinders is provided by the OSHA, [57] [58] Compressed Gas Association, [53] United States Mine Safety and Health Administration (MSHA), [59] EIGA, [56] and other agencies.

Copper catalyses the decomposition of acetylene, and as a result acetylene should not be transported in copper pipes. [60]

Cylinders should be stored in an area segregated from oxidizers to avoid exacerbated reaction in case of fire/leakage. [53] [58] Acetylene cylinders should not be stored in confined spaces, enclosed vehicles, garages, and buildings, to avoid unintended leakage leading to explosive atmosphere. [53] [58] In the US, National Electric Code (NEC) requires consideration for hazardous areas including those where acetylene may be released during accidents or leaks. [61] Consideration may include electrical classification and use of listed Group A electrical components in USA. [61] Further information on determining the areas requiring special consideration is in NFPA 497. [62] In Europe, ATEX also requires consideration for hazardous areas where flammable gases may be released during accidents or leaks. [56]

Related Research Articles

<span class="mw-page-title-main">Alkyne</span> Hydrocarbon compound containing one or more C≡C bonds

In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula CnH2n-2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic.

<span class="mw-page-title-main">Carbide</span> Inorganic compound group

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.

<span class="mw-page-title-main">Hydrocarbon</span> Organic compound consisting entirely of hydrogen and carbon

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; their odor is usually faint, and may be similar to that of gasoline or lighter fluid. They occur in a diverse range of molecular structures and phases: they can be gases, liquids, low melting solids or polymers.

<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

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)–. The simplest ketone is acetone, with the formula CH3C(O)CH3. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Organometallic chemistry</span> Study of organic compounds containing metal(s)

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 sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide, cyanide, or carbide, are generally considered to be organometallic as well. Some related compounds such as transition metal hydrides and metal phosphine complexes are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term "metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, alkoxides, dialkylamides, and metal phosphine complexes are representative members of this class. The field of organometallic chemistry combines aspects of traditional inorganic and organic chemistry.

<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are common and play important roles in the technology and biological spheres.

Ethane is an organic chemical compound with chemical formula C
2
H
6
. 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 by-product of petroleum refining. Its chief use is as feedstock for ethylene production.

In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and butan-2-ol.

<span class="mw-page-title-main">Calcium carbide</span> Chemical compound

Calcium carbide, also known as calcium acetylide, is a chemical compound with the chemical formula of CaC2. Its main use industrially is in the production of acetylene and calcium cyanamide.

<span class="mw-page-title-main">Ethylene oxide</span> Cyclic compound (C2H4O)

Ethylene oxide is an organic compound with the formula C2H4O. It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of silver catalyst.

In organometallic chemistry, acetylide refers to chemical compounds with the chemical formulas MC≡CH and MC≡CM, where M is a metal. The term is used loosely and can refer to substituted acetylides having the general structure RC−CM. Acetylides are reagents in organic synthesis. The calcium acetylide commonly called calcium carbide is a major compound of commerce.

<span class="mw-page-title-main">Wacker process</span>

The Wacker process or the Hoechst-Wacker process refers to the oxidation of ethylene to acetaldehyde in the presence of palladium(II) chloride as the catalyst. This chemical reaction was one of the first homogeneous catalysis with organopalladium chemistry applied on an industrial scale.

<span class="mw-page-title-main">Industrial gas</span> Gaseous materials produced for use in industry

Industrial gases are the gaseous materials that are manufactured for use in industry. The principal gases provided are nitrogen, oxygen, carbon dioxide, argon, hydrogen, helium and acetylene, although many other gases and mixtures are also available in gas cylinders. The industry producing these gases is also known as industrial gas, which is seen as also encompassing the supply of equipment and technology to produce and use the gases. Their production is a part of the wider chemical Industry.

<span class="mw-page-title-main">Silver acetylide</span> Chemical compound

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 name "silver carbide" is rarely used, although the analogous calcium compound CaC2 is called calcium carbide. Silver acetylide is a primary explosive.

Copper(I) acetylide, or cuprous acetylide, is a chemical compound with the formula Cu2C2. 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 formula Cu
2
C
2
.H
2
O
. It is a reddish solid, that easily explodes when dry.

<span class="mw-page-title-main">Walter Reppe</span> German chemist (1892-1969)

Walter Julius Reppe was a German chemist. He is notable for his contributions to the chemistry of acetylene.

The Castro–Stephens coupling is a cross coupling reaction between a copper(I) acetylide and an aryl halide in pyridine, forming a disubstituted alkyne and a copper(I) halide.

The Favorskii reaction is an organic chemistry reaction between an alkyne and a carbonyl group, under basic conditions. The reaction was discovered in the early 1900s by the Russian chemist Alexei Yevgrafovich Favorskii.

Lithium carbide, Li
2
C
2
, 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. Li
2
C
2
is one of an extensive range of lithium-carbon compounds which include the lithium-rich Li
4
C
, Li
6
C
2
, Li
8
C
3
, Li
6
C
3
, Li
4
C
3
, Li
4
C
5
, and the graphite intercalation compounds LiC
6
, LiC
12
, and LiC
18
.
Li
2
C
2
is the most thermodynamically-stable lithium-rich carbide and the only one that can be obtained directly from the elements. It was first produced by Moissan, in 1896 who reacted coal with lithium carbonate.

In organic chemistry, alkynylation is an addition reaction in which a terminal alkyne is added to a carbonyl group to form an α-alkynyl alcohol.

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