Acetylene

Acetylene (systematic name: ethyne) is the chemical compound with the formula C₂H₂. It is a hydrocarbon and the simplest alkyne.

Quotes

• With the start of the industrial production of acetaldehyde by acetylene hydration in 1916, acetylene became one of the most important raw materials for coal-based chemistry in the first half of the 20th century. However, the move from coal chemistry to petrochemistry made ethylene and propylene incomparably more important than acetylene.[…] Conversions starting with acetylene are rather underdeveloped compared with many other fields in catalysis, which offers the possibility for significant improvement by applying modern concepts, new materials, and state-of-the-art process technology. In order to reduce our society’s dependence on oil-derived feedstocks, acetylene could serve as a platform molecule that can be transformed into various base chemicals. This should not be seen as a step back to coal chemistry but rather a step toward a diversified chemical industry where acetylene is a valuable molecule that can be selectively transformed to materials guaranteeing our prosperity.
  • Ioan-Teodor Trotuş, Tobias Zimmermann, and Ferdi Schüth, "Catalytic Reactions of Acetylene: A Feedstock for the Chemical Industry Revisited." Chemical reviews 114.3 (2013): 1761-1782.

• In ethyne, the two carbons are sp hybridized. (...) One of the hybrid orbitals on each carbon overlaps with hydrogen, and a σ bond between the two carbon atoms results from mutual overlap of the remaining sp hybrids. The two perpendicular p orbitals on each carbon contain one electron each. These two sets overlap to form two perpendicular π bonds.
  • K. Peter C. Vollhardt, Neil E. Schore (2011) Organic chemistry : structure and function 6th ed. Ch. 13 : Alkynes

• In summary, we have carried out a combined QM calculation and MD simulation study to better understand the removal mechanism of C₂H₂ from a C₂H₄ stream by [BMIM][OAc]. Based on the calculated interaction energies, it is proposed that both C₂H₂ and C₂H₄ molecules prefer to link to the anion of IL via the hydrogen bonding interaction between an acidic proton of C₂H₂/C₂H₄ and the basic oxygen atom in [OAc] − and link to the cation of IL via the C−H···π interaction between the C−H bond of C₂H₂/C₂H₄ and the imidazolium ring of the cation. However, the interaction of C₂H₂ with the cation, anion, and ion pair are found to be stronger than those of C₂H₄.
  • Hao Xu, Zhe Han, Dongju Zhang, and Jinhua Zhan, "Interface Behaviors of Acetylene and Ethylene Molecules with 1-Butyl-3-methylimidazolium Acetate Ionic Liquid: A Combined Quantum Chemistry Calculation and Molecular Dynamics Simulation Study." ACS applied materials & interfaces 4.12 (2012): 6646-6653.