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Synthesis

Titanium Sparks Ethane-To-Ethylene Conversion ...

by Bethany Halford
July 4, 2011 | A version of this story appeared in Volume 89, Issue 27

Titanium alkylidyne
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With the help of a titanium alkylidyne reagent, chemists have found a way to make ethylene from ethane at room temperature (J. Am. Chem. Soc., DOI: 10.1021/ja202316m). Ethane is a major component of natural gas, but for uses other than fuel, such as to make polymers or more reactive two-carbon compounds, the saturated hydrocarbon needs to become a molecule with a reactive handle. This feat is typically done by stripping off hydrogen via steam cracking to make ethylene. That process, however, requires temperatures in excess of 800 °C and produces as much as 3 tons of carbon dioxide for each ton of ethylene. Researchers at Indiana University led by and found that they could dehydrogenate ethane at 21 °C using stoichiometric amounts of the titanium alkylidyne shown. The transient organometallic species activates one of ethane’s C–H bonds and then cuts in on an adjacent C–H bond to give a titanium-ethylene adduct. Subsequent two-electron oxidation by an organic azide or nitrous oxide quantitatively releases ethylene.

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