Acetylene

Last updated
Acetylene
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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
EC Number
  • 200-816-9
210
KEGG
PubChem CID
RTECS number
  • AO9600000
UNII
UN number 1001 (dissolved)
3138 (in mixture with ethylene and propylene)
Properties
C2H2
Molar mass 26.038 g·mol−1
AppearanceColorless gas
Odor Odorless
Density 1.097 g/L = 1.097 kg/m3
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
Vapor pressure 44.2 atm (20 °C) [3]
Acidity (pKa)25 [4]
Conjugate acid Ethynium
−12.5×10−6 cm3/mol
Structure
Linear
Thermochemistry
201 J/(mol·K)
+226.88 kJ/mol
Hazards
GHS pictograms GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
GHS Signal word Danger
H220, H336
P202, P210, P261, P271, P304, P340, P312, P377, P381, P403, P403, P233, P405, P501
NFPA 704 (fire diamond)
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no codeAcetylene
4
1
3
300 °C (572 °F; 573 K)
NIOSH (US health exposure limits):
PEL (Permissible)
none [3]
REL (Recommended)
C 2500 ppm (2662 mg/m3) [3]
IDLH (Immediate danger)
N.D. [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Acetylene (systematic name: ethyne) is the chemical compound with the formula C2H2. It is a hydrocarbon and the simplest alkyne. [5] 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. [6] Pure acetylene is odorless, but commercial grades usually have a marked odor due to impurities. [7]

Contents

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°. [8]

Discovery

Acetylene was discovered in 1836 by Edmund Davy, who identified it as a "new carburet of hydrogen". [9] [10] 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. [11] Berthelot's empirical formula for acetylene (C4H2), as well as the alternative name "quadricarbure d'hydrogène" (hydrogen quadricarbide), were incorrect because chemists at that time used the wrong atomic mass for carbon (6 instead of 12).[ citation needed ] 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. [12] [13] Commercially available acetylene gas may carry the odors from impurities divinyl sulfide and phosphine. [6]

Preparation

Since the 1950s, acetylene has mainly been manufactured by the partial combustion of methane. [6] [14] [15] 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. [6] 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. [16]

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 [17] 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-19th century revolution in chemistry enabled by the massive hydroelectric power project at Niagara Falls. [18]

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. [19]

Since acetylene is a linear symmetrical molecule, it possesses the D∞h point group. [20]

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. [21]

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. [22]

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. [23] 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. Oxy-acetylene 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. [24]

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

Calcium carbide was used to generate acetylene used in the lamps for portable or remote applications. It was used for miners and cavers before the widespread use of incandescent lighting; or many years later low-power/high-lumen LED lighting; and is still used by mining industries in some nations without workplace safety laws. Carbide lamps were also used extensively as headlights in early motor vehicles and as an early light source for lighthouses. [25]

Plastics and acrylic acid derivatives

Except in China, use of acetylene as a chemical feedstock has declined by 70% from 1965 to 2007 owing to cost and environmental considerations. 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. [6] These derivatives form products such as acrylic fibers, glasses, paints, resins, and polymers. [26]

Niche applications

In 1881, the Russian chemist Mikhail Kucherov [27] 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. [28]

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. [6]

In the early 20th century acetylene was widely used for illumination, including street lighting in some towns. [29] Most early automobiles used carbide lamps before the adoption of electric headlights. [30]

Acetylene is sometimes used for carburization (that is, hardening) of steel when the object is too large to fit into a furnace. [31]

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. [32]

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. [ citation needed ] A number of bacteria living on acetylene have been identified. The enzyme acetylene hydratase catalyzes the hydration of acetylene to give acetaldehyde: [33]

C2H2 + H2O → CH3CHO

Acetylene is a moderately common chemical in the universe, often associated with the atmospheres of gas giants. [34] 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. [35] [36]

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. [22] [6]

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.

Addition to formaldehyde

Acetylene adds to ketones and aldehydes in the presence of base catalysts. With carbonyl groups to give α-ethynyl alcohols in ethynylation reactions: [6] Formaldehyde gives sequentially propargyl alcohol and butynediol. 1,4-Butynediol is produced industrially in this way from formaldehyde and acetylene. [6]

Reppe-chemistry-endiol-V1.svg

Carbonylation

Walter Reppe discovered that in the presence of catalysts, acetylene react to give a wide range of industrially significant chemicals. [6] [37] [38]

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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: [26]

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, [6] and carbonylation to hydroquinone: [37]

Reppe-chemistry-benzene.png
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Fe(CO)5 + 4 C2H2 + 2 H2O → 2 C6H4(OH)2 + FeCO3 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. [39]

Acid-base reactions

Acetylene has a pKa of 25, acetylene can be deprotonated by a superbase to form an acetylide: [39]

HC≡CH + RM → RH + HC≡CM

Various organometallic [40] and inorganic [41] 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. [42] [43] It is therefore supplied and stored dissolved in acetone or dimethylformamide (DMF), [43] [44] [45] 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. [46]

Information on safe storage of acetylene in upright cylinders is provided by the OSHA, [47] [48] Compressed Gas Association, [43] United States Mine Safety and Health Administration (MSHA), [49] EIGA, [46] and other agencies.

Copper catalyses the decomposition of acetylene, and as a result acetylene should not be transported in copper pipes. [50]

Cylinders should be stored in an area segregated from oxidizers to avoid exacerbated reaction in case of fire/leakage. [43] [48] Acetylene cylinders should not be stored in confined spaces, enclosed vehicles, garages, and buildings, to avoid unintended leakage leading to explosive atmosphere. [43] [48] In the US, National Electric Code (NEC) requires consideration for hazardous areas including those where acetylene may be released during accidents or leaks. [51] Consideration may include electrical classification and use of listed Group A electrical components in USA. [51] Further information on determining the areas requiring special consideration is in NFPA 497. [52] In Europe, ATEX also requires consideration for hazardous areas where flammable gases may be released during accidents or leaks. [46]

Related Research Articles

Aliphatic compound class of chemical compounds without aromatic ring

In organic chemistry, hydrocarbons are divided into two classes: aromatic compounds and aliphatic compounds, also known as non-aromatic hydrocarbons. Aliphatics can be cyclic; however, hydrocarbons with conjugated pi-systems that obey Hückel's rule are instead considered to be aromatic. Aliphatic compounds can be saturated, like hexane, or unsaturated, like hexene and hexyne. Open-chain compounds contain no rings of any type, and are thus aliphatic.

Alkyne acyclic hydrocarbon with one triple bond between carbon atoms

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 but tend to be more reactive.

Carbide 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.

Hydrocarbon 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 from which one hydrogen atom has been removed are functional groups called hydrocarbyls. Because carbon has 4 electrons in its outermost shell carbon has exactly four bonds to make, and is only stable if all 4 of these bonds are used.

Organometallic chemistry study of chemical compounds containing at least one bond between a carbon atom of an organic compound and a metal

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 alkaline, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and tin, 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.

Aldehyde Organic compound containing a functional group with the structure −CHO

An aldehyde is a compound containing a functional group with the structure −CHO, consisting of a carbonyl center with the carbon atom also bonded to hydrogen and to an R group, which is any generic alkyl or side chain. The group—without R—is the aldehyde group, also known as the formyl group. Aldehydes are common in organic chemistry, and many fragrances are or contain aldehydes.

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 2-butanol.

Calcium carbide 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.

Propene, also known as propylene or methyl ethylene, is an unsaturated organic compound having the chemical formula . It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petroleum-like odor

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.

Kipps apparatus Laboratory device for preparing gases.

Kipp's apparatus, also called Kipp generator, is an apparatus designed for preparation of small volumes of gases. It was invented around 1844 by the Dutch pharmacist Petrus Jacobus Kipp and widely used in chemical laboratories and for demonstrations in schools into the second half of the 20th century.

Silver acetylide 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.

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.

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

The Favorskii reaction is an organic chemistry reaction between an alkyne and a carbonyl group, under a basic condition. 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 compound 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.

Organonickel

Organonickel chemistry is a branch of organometallic chemistry that deals with organic compounds featuring nickel-carbon bonds. They are used as a catalyst, as a building block in organic chemistry and in chemical vapor deposition. Organonickel compounds are also short-lived intermediates in organic reactions. The first organonickel compound was nickel tetracarbonyl Ni(CO)4, reported in 1890 and quickly applied in the Mond process for nickel purification. Organonickel complexes are prominent in numerous industrial processes including carbonylations, hydrocyanation, and the Shell higher olefin process.

Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbonylation also refers to oxidation of protein side chains.

In organometallic chemistry, a transition metal alkyne complex is a coordination compound containing one or more alkyne ligands. Such compounds are intermediates in many catalytic reactions that convert alkynes to other organic products, e.g. hydrogenation and trimerization.

Alkynylation is an addition reaction in organic synthesis where a terminal alkyne adds to a carbonyl group to form an α-alkynyl alcohol. When the acetylide is formed from acetylene, the reaction gives an α-ethynyl alcohol. This process is often referred to as ethynylation. Such process often involve metal acetylide intermediates

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