Ethane

by Stephen Dyrgas
Ethane
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HistoryEthane was first synthetically created in 1834 by Michael Faraday, applying electrolysis of a potassium acetate solution. He mistook the hydrocarbon product of this reaction for methane, and did not investigate it further. During the period 18471849, in an effort to vindicate the radical theory of organic chemistry, Hermann Kolbe and Edward Frankland produced ethane by the reductions of propionitrile (ethyl cyanide) and ethyl iodide with potassium metal, and, as did Faraday, by the electrolysis of aqueous acetates. They, however, mistook the product of these reactions for methyl radical, rather than the dimer of methyl, ethane. This error was corrected in 1864 by Carl Schorlemmer, who showed that the product of all these reactions was in fact ethane.Its name was made from the name of ether, which at first meant diethyl ether. ChemistryIn the laboratory, ethane may be conveniently prepared by Kolbe electrolysis. In this technique, an aqueous solution of an acetate salt is electrolysed. At the anode, acetate is oxidized to produce carbon dioxide and methyl radicals, and the highly reactive methyl radicals combine to produce ethane:CH3COO CH3 + CO2 + eCH3 + CH3 C2H6Another method, the oxidation of acetic anhydride by peroxides, is conceptually similar.The chemistry of ethane also involves chiefly free radical reactions. Ethane can react with the halogens, especially chlorine and bromine, by free radical halogenation. This reaction proceeds through the propagation of the ethyl radical:C2H5 + Cl2 C2H5Cl + ClCl + C2H6 C2H5 + HClBecause halogenated ethanes can undergo further free radical halogenation, this process results in a mixture of several halogenated products. In the chemical industry, more selective chemical reactions are used for the production of any particular two-carbon halocarbon. CombustionThe complete combustion of ethane releases 1561 kJ/mol, or 51.9 kJ/g, of heat, and produces carbon dioxide and water according to the chemical equation2 C2H6 + 7 O2 4 CO2 + 6 H2O + 3170 kJ/molCombustion occurs by a complex series of free-radical reactions. Computer simulations of the chemical kinetics of ethane combustion have included hundreds of reactions. An important series of reaction in ethane combustion is the combination of an ethyl radical with oxygen, and the subsequent breakup of the resulting peroxide into ethoxy and hydroxyl radicals.C2H5 + O2 C2H5OOC2H5OO + HR C2H5OOH + RC2H5OOH C2H5O + OHThe principal carbon-containing products of incomplete ethane combustion are single-carbon compounds such as carbon monoxide and formaldehyde. One important route by which the carbon-carbon bond in ethane is broken to yield these single-carbon products is the decomposition of the ethoxy radical into a methyl radical and formaldehyde, which can in turn undergo further oxidation.C2H5O CH3 + CH2OSome minor products in the incomplete combustion of ethane include acetaldehyde, methane, methanol, and ethanol. At higher temperatures, especially in the range 600900 C, ethylene is a significant product. It arises via reactions likeC2H5 + O2 C2H4 + OOHSimilar reactions

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