• What is Acetylene? Acetylene, a hydrocarbon with the molecular formula C2H2, stands as a pivotal compound in numerous industrial processes. This report provides an in-depth exploration of acetylene, from its chemical structure and production methods to its diverse applications, safety considerations, environmental impact, and a real-world case study. The purpose is to unravel the multifaceted nature of acetylene and emphasize its indispensable role in various industrial sectors. The Molecular Symphony of Acetylene
• Molecular Formula: C2H2
• Triple Bond Structure: Acetylene's
uniqueness lies in its triple bond structure between two carbon atoms, imparting distinct chemical properties.
• Unsaturation Explanation: This triple bond
results in unsaturation, making acetylene highly reactive and a cornerstone in organic synthesis. Production Methods of Acetylene \ It is produced through a chemical process known as the acetylene generation. There are several methods for producing acetylene, but the most common ones are the carbide-to- acetylene process and the hydrocarbon-to-acetylene process.
1. Carbide-to-Acetylene Process (Calcium Carbide Method):
• Calcium carbide (CaC2) reacts with water to produce acetylene gas and calcium hydroxide (Ca(OH)2). • The reaction can be represented as follows: CaC2 + 2H2O → C2H2 + Ca(OH)2 • The process involves feeding water into a chamber containing chunks of calcium carbide. The resulting acetylene gas is then collected and purified
2. Hydrocarbon-to-Acetylene Process (Thermal Cracking):
• In this method, hydrocarbons such as methane or natural gas are subjected to high temperatures, causing them to undergo thermal cracking. • The basic reaction involves breaking down the hydrocarbons into simpler molecules, including acetylene: 2CH4 → C2H2 + 3H2 • This process often requires high temperatures and may involve catalysts to enhance the yield of acetylene.
3. Partial Oxidation of Hydrocarbons:
• Acetylene can also be produced by partially oxidizing hydrocarbons such as methane with limited oxygen supply. • The partial oxidation reaction can be represented as follows: 2CH4 + O2 → C2H2 + 4H2 • This method is typically carried out in the presence of a suitable catalyst to control the reaction and improve selectivity. Physical Properties Due to the carbon–carbon triple bond and the high positive energy of formation, acetylene is an unstable, highly reactive unsaturated hydrocarbon. The C – C triple bond and C – H s bond lengths are 0.1205 and 0.1059 nm, respectively. For the electronic structure of acetylene and a molecular orbital description, see [4]. The acidity of acetylene (p𝑘a¼ 25) permits the formation of acetylides (see Section 3.2). For comparison the pKa value of ethylene is 44 and that of acetone 20. Under normal conditions acetylene is a colorless, nontoxic but narcotic gas; it is slightly lighter than air. The main physical properties are listed in Table 1. The critical temperature and pressure are 308.32 K and 6.139 MPa. The triple point at 128.3 kPa is 192.4 K. The vapor pressure curve for acetylene is shown in Figure 1.
Table 1. Physical properties of acetylene [5–8]
Molecular mass 26.0379
Critical temperature 308.32 K (35.17 C) Critical pressure 6.139 MPa Critical volume 0.113 m3/kmol Triple point 192.4 K (- 80.75 C) Triple point pressure 128.3 kPa Normal sublimation point and 189.15 K (- 84.0 C) normal boiling point Crystal transition point 133.0 K (- 140.15 C) Enthalpy of transition 2.54 kJ/mol Density 760.2 kg/m3 (131 K) 764.3 kg/m3 (141 K) Density (liquid C2H2) 465.2 kg/m3 (273.15 K) Density (gaseous 1.095 kg/m3 (288.15 K) C2H2 at 1 bar) Molecular volume 22.223 m3/kmol Figure 1. Vapor pressure of acetylene [5, 6] (0 C, 1.013 bar)
Enthalpy of vaporization 10.65 kJ/mol (273.15 K)
(calculated) Enthalpy of sublimation 21.168 kJ/mol (5.55 K) Enthalpy of formation 227.5 1.0 kJ/mol (298.15 K) Gibbs free energy of formation 209.2 1.0 kJ/mol (298.15 K)
Entropy of formation 200.8 J mol1 K1 (298.15 K)
Enthalpy of combustion 1255.6 kJ/mol (298.15 K) Higher heating value 50 400 kJ/kg Lower heating value 48 700 kJ/kg Vapor pressure 2.6633 MPa (273.15 K) Thermal conductivity 0.0184 W m1 K1 (0 C, 1.013 bar) Heat capacity (ideal gas state) 43.990 J mol1 K1 (298.15 K)
Figure 2. Density of acetylene vapor (at 1.013 bar) and liquid
Chemical Properties
Because of its strongly unsaturated character and high positive
free energy of formation, acetylene reacts readily with many elements and Because compounds. of its Ascharacter strongly unsaturated a result, acetylene and high positive free is used energy of as raw formation, acetylene reacts readily with many elements and compounds. As a result material for ais used acetylene great variety as raw ofasubstances. material for Important great variety of substances. are Important areaddition reactions, hydrogen replacements, polymerization, and addition reactions, hydrogen replacements, polymerization, and cyclization.
cyclization.
Figure 3. Adsorption isotherms for acetylene on 4A and 5A molecular sieves,
activated carbon, and silica gel at 25 C [14]
Acetylene is more susceptible to nucleophilic attack than, for instance, ethylene. In
addition, the polarized C-H bond makes acetylene acidic (pKa ¼ 25) [16]. Because of this acidity, acetylene is very soluble in basic solvents [17, 18], forming hydrogen bonds with them [19]. Therefore, the vapor pressures of such solutions cannot be described by Raoult’s law [20]. The development of the acetylene pressure reactions by W. REPPE (1892 – 1969), BASF Ludwigshafen (Germany) [21–23] began modern acetylene chemistry. The most interesting groups of reactions are vinylation, ethynylation, carbonylation, and cyclic and linear polymerization. Industrially Important Catalyst: cadmium, zinc, or mercury salts on coal. Gas-phase reaction at 180 – 200 C. Reactions Vinyl Ethers (! Vinyl Ethers), conjectured reaction Vinylation Reactions and Products [24]. Vinylation is steps: the addition of compounds with a mobile hydrogen atom, such as water, alcohols, thiols, amines, and organic and inorganic acids, to acetylene to form vinyl compounds chiefly used for polymerization. where R is an alkyl group. Reaction temperature of The two types of vinylation reactions are 120 – 150 C; pressure high enough to avoid boiling heterovinylation and the less usual C vinylation. In the alcohol used, e.g., 2 MPa with methanol to the former, the hydrogen atom originates from the produce methyl vinyl ether (acetylene pressure heteroatoms O, S, and N, whereas C vinylation reaction). occurs when the mobile hydrogen atom is directly bound to a carbon atom. Examples of C vinylation Vinyl Phenyl Ether [766-94-9], vinylation with KOH are dimerization and trimerization of acetylene, the catalyst: synthesis of acrylonitrile from acetylene and hydrogen cyanide, and the addition of acetylene to unsaturated hydrocarbons with activated hydrogen atoms, such as cyclopentadiene, indene, fluorene, and anthracene.
The first industrial vinylation products were
acetaldehyde, vinyl chloride, and vinyl acetate. Many other products followed.
Some examples of industrial vinylation processes are
given below: Catalyst: zinc or cadmium salts. Liquid-phase reaction.
Catalyst: acidic solutions of mercury salts, such as
HgSO4 in H2SO4. Liquid-phase reaction at 92 C.
Catalyst: HgCl2 on coal. Gas-phase reaction at 150 –180C.
Purification and drying of Acetylene
Acetylene is purified mainly to remove phosphine and
hydrogen sulphide. The need for purification is based on the calcium carbide quality, the process and required acetylene specification. Two purifying methods are in use, dry purification and wet purification .
Exposure of CaCl2 to moisture creates a water discharge rich in CaCl2 that can be viscous. If this is allowed to thicken it can lead to restriction in the discharge line. One safeguard against this is to thoroughly clean the drier vessels on a periodic basis. This can be accomplished by removing the unused CaCl2 and washing with hot water or steam. Manufacturers recommend flushing the material at the base of the driers with at least 4 liters of warm water every time that CaCl2 is changed or added. Navigating Safely with Acetylene
• Acetylene is a highly flammable and potentially hazardous gas
that requires careful handling to ensure safety. When using acetylene, it is crucial to store it in approved containers designed to withstand its unique properties. Acetylene cylinders should always be stored in an upright position to prevent the acetone within from contaminating the gas.
• Additionally, proper ventilation is essential when working with
acetylene to prevent the accumulation of explosive mixtures. Users should inspect hoses, regulators, and equipment regularly for leaks or damage, as acetylene can react violently with certain materials.
• To minimize risks, never exceed recommended pressures, and
always use appropriate personal protective equipment, such as flame-resistant clothing and safety goggles. It is vital to follow established safety guidelines and procedures for acetylene use, including proper shutdown and storage protocols. Conclusion • In conclusion, our exploration of acetylene has unveiled a multifaceted understanding of this crucial compound. From its intricate chemical structure to diverse production methods, we've delved into its physical and chemical properties.
• Recognizing its pivotal role in various
industries, we've highlighted the significance of acetylene and its indispensable applications.
• Examining purification and drying processes
underscores the importance of ensuring its quality for industrial use. • Moreover, stringent safety measures are imperative, emphasizing the need for responsible handling. As industries evolve, so does the demand for acetylene, making it imperative to continually refine production techniques and safety protocols. This comprehensive overview serves as a foundation for further research and underscores the enduring importance of acetylene in industrial landscapes. References
