Acetylene

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"HCCH" redirects here. For other uses, see HCCH (disambiguation).
Not to be confused with ethene.

Acetylene

Names

Preferred IUPAC name

Acetylene[1]

Systematic IUPAC name

Ethyne[2]

Identifiers
CAS Number
74-86-2

3D model (Jmol) Interactive image

ChEBI CHEBI:27518

ChEMBL ChEMBL116336

ChemSpider 6086

ECHA InfoCard 100.000.743

KEGG C01548

UNII OC7TV75O83

UN number 1001 (dissolved)

3138 (in mixture with ethylene and propylene)

InChI[show]

SMILES[show]

Properties

Chemical formula
C2H2

Molar mass 26.04 gmol1

Appearance Colorless 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

Sublimation
84 C; 119 F; 189 K (1 atm)
conditions

Solubility in water
slightly soluble
Vapor pressure 44.2 atm (20 C)[3]

Acidity (pKa) 25[4]

Magnetic susceptibility ()
-12.5106 cm3/mol

Structure

Molecular shape
Linear

Thermochemistry

Std molar
201 Jmol1K1
entropy (So298)

Std enthalpy of
+226.88 kJ/mol
formation (fHo298)

Hazards

NFPA 704

Autoignition
300 C (572 F; 573 K)
temperature

US health exposure limits (NIOSH):

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).
 verify (what is ?)

Infobox references

Acetylene (systematic name: ethyne) is the chemical compound with the formula C H . It is 2 2

a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical
[5]

building block. It is unstable in its pure form and thus is usually handled as a solution. Pure [6]

acetylene is odorless, but commercial grades usually have a marked odor due to impurities. [7]

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

1Discovery

2Preparation

3Bonding

4Physical properties
o 4.1Changes of state
o 4.2Other

5Reactions
o 5.1Metal acetylides
o 5.2Reppe chemistry

6Applications
o 6.1Welding
o 6.2Portable lighting
o 6.3Plastics and acrylic acid derivatives
o 6.4Niche applications

7Natural occurrence

8Safety and handling

9References

10External links

Discovery[edit]
Acetylene was discovered in 1836 by Edmund Davy, who identified it as a "new carburet of
hydrogen". It was rediscovered in 1860 by French chemist Marcellin Berthelot, who coined the
[8][9]

name "actylne". Berthelot's empirical formula for acetylene (C H ), as well as the alternative name
[10]
4 2

"quadricarbure d'hydrogne" (hydrogen quadricarbide) were incorrect because 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. He also found acetylene was formed by sparking electricity through
mixed cyanogen and hydrogen gases. Berthelot later obtained acetylene directly by passing
hydrogen between the poles of a carbon arc. Commercially available acetylene gas could smell
[11][12]

foul due to the common impurities hydrogen sulfide and phosphine. However, as purity increases it
will become odourless.

Preparation[edit]
Since the 1950s, acetylene has mainly been manufactured by the
partial combustion of methane or appears as a side product in the ethylene stream
[6][13][14]
from cracking of hydrocarbons. 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
[6]

ability to poison Ziegler-Natta catalysts. It is selectively hydrogenated into ethylene, usually using
PdAg catalysts. [15]

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 Whler in
1862 and still familiar to students:
[16]

CaC + 2H O Ca(OH) + C H
2 2 2 2 2

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. [17]

Bonding[edit]
In terms of valence bond theory, in each carbon atom the 2s orbitalhybridizes 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 valence bond between the carbons, while on
each of the other two ends hydrogen atoms attach also by bonds. The two unchanged 2p
orbitals form a pair of weaker bonds. [18]

Since acetylene is a linear symmetrical molecule, it possesses the D point group.

h
[19]

Physical properties[edit]
Changes of state[edit]
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
minimum 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 C.
Other[edit]
The adiabatic flame temperature in air at atmospheric pressure is 2534 C.
Acetylene gas can be dissolved in acetone or dimethylformamide in room temperature and 1
atm.

Reactions[edit]
Metal acetylides[edit]
Main article: Acetylide Preparation
Since acetylene has a pK of 25, acetylene can be deprotonated by a superbase to form
a

an acetylide: [20]

HCCH + RM RH + HCCM
Various organometallic and inorganic reagents are effective. The formation of the
[21] [22]

acetylide depends upon several factors such as the pK of the base, the valency of the
b

metal, and solvent characteristics. [20]

Copper(I) acetylide and silver acetylide can be formed in aqueous solutions with especial
ease due to a poor solubility equilibrium.
[20]

Reppe chemistry[edit]
Walter Reppe discovered that in the presence of metal catalysts, acetylene can react to give
a wide range of industrially significant chemicals. [23][24]

With alcohols, hydrogen cyanide, hydrogen chloride, or carboxylic acids to

give vinyl compounds: [6]

With carbonyl groups to give -ethynyl alcohols in ethynylation reactions: [6]

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

With carbon monoxide to give acrylic acid, or acrylic esters, which can be
used to produce acrylic glass: [25]

Cyclicization to
give benzene, cyclooctatetraene, or hydroquinone:
[6] [24]
at basic conditions(50-80 C, 20-25 atm).

Applications[edit]
Welding[edit]
Approximately 20 percent 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. Acetylene is the third-hottest natural chemical flame
[26]

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 very popular welding process in
previous decades; however, 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. As well, oxy-fuel cutting is still very
popular and oxy-acetylene cutting is utilized in nearly every
metal fabrication shop. For use in welding and cutting, the
working pressures must be controlled by a regulator, since
above 15 psi, if subjected to a shockwave (caused for
[27]

example by a flashback), acetylene

[28]

will decompose explosively into hydrogen and carbon.

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

Portable lighting[edit]
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. It
was also used as an early light source for lighthouses.
Plastics and acrylic acid derivatives[edit]
Acetylene can be partially hydrogenated to ethylene,
providing a feedstock for a variety of polyethylene plastics.
Another major application of acetylene is its conversion
to acrylic acid derivatives. These derivatives form products
[6]

such as acrylic fibers, glasses, paints, resins,

and polymers. [25]

Niche applications[edit]
In 1881, the Russian chemist Mikhail Kucherov described [29]

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. [30]

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. Most
[31]

early automobiles used carbide lamps before the adoption

of electric headlights.
Acetylene is sometimes used for carburization (that is,
hardening) of steel when the object is too large to fit into a
furnace.[32]

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 be fed into mass
spectrometer to measure the isotopic ratio of carbon-14 to
carbon-12. [33]

Natural occurrence[edit]
The energy richness of the CC 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 acetylene hydratase catalyzes
the hydration of acetylene to give acetaldehyde. [34]

C H + H O CH CHO
2 2 2 3

Acetylene is a moderately common chemical in the

universe, often associated with the atmospheres of gas
giants. One curious discovery of acetylene is
[35]

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. [36][37]

Safety and handling[edit]

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
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.
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 kPa or 15 gage

psig. It is therefore supplied and stored dissolved

[38][39]

in acetone or dimethylformamide (DMF), contained [39][40][41]

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. [42]

Information on safe storage of acetylene in upright

cylinders is provided by the OSHA, Compressed [43][44]

Gas Association, United States Mine Safety and

[39]

Health Administration (MSHA), EIGA, and other [45] [42]

agencies.
Copper catalyses the decomposition of acetylene and
as a result acetylene should not be transported in
copper pipes. Brass pipe fittings should also be
avoided.
Cylinders should be stored in an area segregated from
oxidizers to avoid exacerbated reaction in case of
fire/leakage. Acetylene cylinders should not be
[39][44]

stored in confined spaces / enclosed vehicles /

garages / buildings to avoid unintended leakage
leading to explosive atmosphere. In the USA, [39][44]

National Electric Code (NEC) requires consideration

for hazardous areas including those where acetylene
may be released during accidents or
leaks. Consideration may include electrical
[46]

classification and use of listed Group A electrical

components in USA. Further information on [46]

determining the areas requiring special consideration

is in NFPA 497. In Europe, ATEX also requires
[47]

consideration for hazardous areas where flammable

gases may be released during accidents or leaks. [42]
 The plant includes the following :
Acetylene Generator: The Acetylene Generator offered by us has gained appreciation for advanced design, fully
automatic and superior features. The generator makes use of pneumatically controlled valves and highly sensitive
sensors work in tandem with temperature control instruments to perform different operations. This results in opening
of water inlet or residue drain valve. The supply of Calcium Carbide, fed into the generator b screw-feed conveyors is
controlled by two hydraulic pumps. To ensure optimum safety and ease of operation, the screw-feed mechanism and
agitators are operated by flame-proof motors and fittings. Perfect synchronization and simplicity of operation is
essential to achieve excellent output and efficiency. The generator signals failure of power, water or air supply
visually or through an alarm bell to alert the operator.

Requirements of the generator include:

An acetylene plant can only be fitted with flame proof lights & electrical fittings according to 152148-68 (group II) or
655-229
Acetylene cylinders must be of specification 15: 7312: 1974 or ICC: 8

Temperature Control : The Acetylene generator is equipped with temperature control system to enable the user to
set and operate the plant at a specific temperature. This can be done regardless of the temperature of the cooling
water and size of carbide used. To maintain a standard temperature, a sensor activates pneumatic control which
adds water into the generator tank if the set temperature limit is exceeded. Owing to this, the generator is able to
completely utilize Carbide which is an expensive raw material.

High Pressure Control : The gas pressure in the generator is bound to increase in case the compressor is of low
capacity or the rate of production is faster than rate of absorption. If the gas pressure reaches a predetermined level
of about 0.5 kg/cm2, the generator automatically cuts off carbide charging and stops the production process. Once
the generator has been cleansed with Nitrogen, the generator will maintain a constant positive pressure and inhibit
entering of air into the system. This also helps to reduce the pumping cost and make the plant extremely safe for the
operator.

Water Level Control : In case the water level in the generator exceeds the high level mark, the water level control
instrument will instantly discharge excessive water. The system gets activated when the level of water goes below or
above the prescribed limits
.
No Loss-Carbide charge : To prevent loss of gas or wastage while the carbide is being charged, a high pressure
hydraulic operated valve cuts off the section from the generator. This is an automatic procedure and does not require
operators attention.

Condenser : Condenser performs the function of cooling the produced acetylene gas carrying water vapor and
impurities. The condensation results in removal of excessive moisture and impurities. To perform this operation, the
condenser has appropriate proportions suiting local conditions and efficient in order to assure complete cooling.

Low Pressure Drier : Low pressure drier is charged with Calcium Carbide to absorb the moisture in the generated
gas. If the chemical purifier requires a certain amount of moisture to function effectively, a by-pass can be provided to
allow direct admission of the generated gas partly or wholly.

Chemical Purifier : Chemical purifier utilizes two layers of regenerative chemicals for removing impurities. The
purifying agent can be reactivated for re-use with the help of atmospheric air. Also, to ensure continuous operation an
extra charge of chemicals can be kept in open wooden trolleys.

Water Scrubber : In order to remove impurities from the gas efficiently, water scrubber is installed between the
chemical purifier and acetylene compressor.

Acetylene Compressor : The generator utilizes reciprocating, oil lubricated, multi-stage, water submerged with
intercoolers and an I.R. made compressor for filling the cylinders. The compressor features safety relief valve for
each stage and is driven by a 15 H.P flame proof motor which conforms to IS: 2148-68 (Gr.II-B).
High Pressure Drier : High pressure drier works on a battery of three high-pressure vessels. The first vessel is filled
with Anhydrous Calcium Chloride, High Pressure Drier: High pressure drier works on a battery of three high-pressure
vessels. The first vessel is filled with Anhydrous Calcium Chloride,

Filling Manifold : This consists of a battery of filling connections, which is used to connect to the gas cylinders. Also,
non-return valves are used to adjoin various sections of the pipeline to the filling manifold.

To ensure optimum safe operation of the plant, these non-return valves should be checked from time to time. Also,
the manifold should be periodically checked and cleaned to remove rust and scales which can prove to be a serious
security hazard. The flexible hose pipes of the cylinders should also be regularly checked and cleaned to prevent
them from bursting during the filling operation due to sudden discharge of Acetylene.