Ethane

Like many hydrocarbons, ethane is isolated on an industrial scale from natural gas and as a petrochemical by-product of petroleum refining.

[6] The process is now called Kolbe electrolysis: During the period 1847–1849, 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)[7] and ethyl iodide[8] with potassium metal, and, as did Faraday, by the electrolysis of aqueous acetates.

[16] The three hydrogens at each end are free to pinwheel about the central carbon–carbon bond when provided with sufficient energy to overcome the barrier.

The physical origin of the barrier is still not completely settled,[17] although the overlap (exchange) repulsion[18] between the hydrogen atoms on opposing ends of the molecule is perhaps the strongest candidate, with the stabilizing effect of hyperconjugation on the staggered conformation contributing to the phenomenon.

[19] Theoretical methods that use an appropriate starting point (orthogonal orbitals) find that hyperconjugation is the most important factor in the origin of the ethane rotation barrier.

[28][29] Although ethane is a greenhouse gas, it is much less abundant than methane, has a lifetime of only a few months compared to over a decade,[30] and is also less efficient at absorbing radiation relative to mass.

Further analysis of infrared spectroscopic data presented in July 2008[33] provided additional evidence for the presence of liquid ethane in Ontario Lacus.

In 2006, Dale Cruikshank of NASA/Ames Research Center (a New Horizons co-investigator) and his colleagues announced the spectroscopic discovery of ethane on Pluto's surface.

Various refrigeration strategies exist: the most economical process presently in wide use employs a turboexpander, and can recover more than 90% of the ethane in natural gas.

Many patent exist on this theme, but poor selectivity for vinyl chloride and corrosive reaction conditions have discouraged the commercialization of most of them.

Presently, INEOS operates a 1000 t/a (tonnes per annum) ethane-to-vinyl chloride pilot plant at Wilhelmshaven in Germany.

[38] The economic viability of this process may rely on the low cost of ethane near Saudi oil fields, and it may not be competitive with methanol carbonylation elsewhere in the world.

On a much smaller scale, in scientific research, liquid ethane is used to vitrify water-rich samples for cryo-electron microscopy.

Slower freezing methods can generate cubic ice crystals, which can disrupt soft structures by damaging the samples and reduce image quality by scattering the electron beam before it can reach the detector.

Skeletal formula of ethane with all hydrogens and carbons shown
Skeletal formula of ethane with all hydrogens and carbons shown
Skeletal formula of ethane with all implicit carbons shown, and all explicit hydrogens added
Skeletal formula of ethane with all implicit carbons shown, and all explicit hydrogens added
Ball and stick model of ethane
Ball and stick model of ethane
Spacefill model of ethane
Spacefill model of ethane
NFPA 704 four-colored diamond Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine Flammability 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. propane Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazard SA: Simple asphyxiant gas. E.g. nitrogen, helium
Ethane (shown in Newman projection ) barrier to rotation about the carbon-carbon bond. The curve is potential energy as a function of rotational angle. Energy barrier is 12 kJ/mol or about 2.9 kcal/mol . [ 15 ]
A photograph of Titan 's northern latitudes. The dark features are hydrocarbon lakes containing ethane