Last Alkane Standing Finally Yields Its Bonds

A powerful combination of computational and experimental chemistry has yielded a catalyst which can break the extremely strong bonds of methane.

AsianScientist (Apr. 1, 2016) – Using a hybrid breed of computational and experimental chemistry, an international team of chemists led by Institute for Basic Science Center for Catalytic Hydrocarbon Functionalizations Associate Director Baik Mu-Hyun, has finally achieved what has been dubbed the ‘Holy Grail reaction’ of organic chemistry: catalyzing reactions with methane. Their results have been published in Science.

As organic chemistry evolved, techniques for catalyzing hydrocarbons advanced, creating methods for their manipulation one by one. Alkanes such as ethane, propane, butane and pentane follow a similar pattern and their reactions had predictable results. Only one alkane—methane (CH4)—refused to follow suit, confounding chemists for decades.

With its low solubility and non-polar nature, methane has proven to be just too difficult to work with as its carbon-hydrogen (C-H) bond could not be manipulated.

Starting with computational prediction, the team was able to model the reactions between metal catalysts and supporting ligands that would allow boron to be added to methane (borylation). Based on the predictions, the experimental arm of the team tested a variety of combinations of ligands until they found one that worked most efficiently: phosphine ligands.

They then used this ligand with different combinations of catalyst to determine the optimal reaction. They found that they were able to generate impressive yields of up to 52 percent using iridium catalysts.

However, iridium is a rare and extremely expensive material since it is almost exclusively sourced from meteors. Instead, the team is researching replacing iridium with more common metals such as cobalt.

“Cobalt is related to iridium; the only difference is that cobalt is dirt cheap and highly abundant,” Baik said.

Petroleum is quickly becoming a dwindling resource and new methods of creating hydrocarbons are going to be necessary. Being able to manipulate methane would allow it to be easily converted to liquid methanol and shipped for fuel, which will be a crucial step towards petroleum independence.

The article can be found at: Smith et al. (2016) Catalytic Borylation of Methane.


Source: Institute for Basic Science.
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