New way to split tough carbon bonds could open doors for greener chemicals

November 19, 2018, University of Chicago
UChicago chemists, including postdoctoral researcher Jun Zhu, above, devised a method to crack certain carbon-carbon bonds, which could someday let us make chemicals from plants instead of oil. Credit: Nancy Wong

A breakthrough by chemists at the University of Chicago may one day open possibilities for making chemicals from plants rather than oil, by creating a new method to crack certain tough carbon-to-carbon bonds.

A great number of chemicals in the natural and industrial world have backbones made of carbon-on-carbon bonds. These are regularly carved up during processes to make new useful molecules. But a particular subset of these bonds is very stable—and thus difficult to crack open. Chemists would like to discover new ways to cut and rearrange such bonds; a library of such knowledge is key to finding valuable new chemicals or more efficient or greener ways to make known ones.

For example, —a molecule found in plants and trees—has long been eyed as an alternate source of the chemicals made from crude oil, which are used to make plastics and fertilizers. But it contains a lot of these especially tough carbon-carbon bonds. "If we had an efficient method to cleave those bonds, we could potentially make full use of lignin as a sustainable alternative to petroleum," said Guangbin Dong, professor of chemistry at UChicago and coauthor of the study.

The problem is that carbon-carbon bonds are often connected with particularly strong non-polar links. If they could be put into certain configurations that allow a close interaction with a metal catalyst, they can be broken. But before the study, there was no known catalyst that could break such unstrained, non-polar bonds in lignin.

Dong, along with postdoctoral researcher Jun Zhu and graduate student Jianchun Wang, devised a new method to use a metal hydride catalyst to crack the bonds. The metal hydride acts as an active intermediate, inserting itself into the carbon bonds and then grabbing onto hydrogen as well.

The itself isn't suited to commercial use, but it provides proof of concept for the future, the scientists said.

"This provides an opening for further study of such methods," said Dong. "Fundamentally, we want to know the limits of what kind of carbon- could be activated."

Explore further: Silver salt used to break C–C bonds in unstrained cyclic amines

More information: Jun Zhu et al. Catalytic activation of unstrained C(aryl)–C(aryl) bonds in 2,2′-biphenols, Nature Chemistry (2018). DOI: 10.1038/s41557-018-0157-x

Related Stories

Chemists build new chemical structures on unreactive bonds

July 28, 2017

Making complicated organic molecules is like solving a Rubik's cube. Organic chemists need to design sequences of reactions to carefully build up parts of a molecule, while maintaining the structure at other sites. Although ...

New tools for creating mirrored forms of molecules

October 25, 2018

One of the biggest challenges facing synthetic chemists is how to make molecules of only a particular "handedness." Molecules can come in two shapes that mirror each other, just like our left and right hands. This characteristic, ...

CCNY research team in molecular breakthrough

March 14, 2016

Reducing a barrier that generally hinders the easy generation of new molecules, a team led by City College of New York chemist Mahesh K. Lakshman has devised a method to cleave generally inert bonds to allow the formation ...

Breaking benzene

August 27, 2014

Aromatic compounds are found widely in natural resources such as petroleum and biomass, and breaking the carbon-carbon bonds in these compounds plays an important role in the production of fuels and valuable chemicals from ...

Scientists achieve arylation of C-H bonds in mild conditions

December 27, 2017

Carbon-carbon (C-C) bonds make up the skeleton of all organic molecules. However, creating such ubiquitous C-C bonds artificially is still a complicated task. In particular, since several molecules used in medicine, pharmacology ...

Recommended for you

3-D culturing hepatocytes on a liver-on-a-chip device

January 17, 2019

Liver-on-a-chip cell culture devices are attractive biomimetic models in drug discovery, toxicology and tissue engineering research. To maintain specific liver cell functions on a chip in the lab, adequate cell types and ...

This computer program makes pharma patents airtight

January 17, 2019

Routes to making life-saving medications and other pharmaceutical compounds are among the most carefully protected trade secrets in global industry. Building on recent work programming computers to identify synthetic pathways ...

Cultivating 4-D tissues—the self-curving cornea

January 17, 2019

Scientists at Newcastle University have developed a biological system which lets cells form a desired shape by moulding their surrounding material—in the first instance creating a self-curving cornea.


Please sign in to add a comment. Registration is free, and takes less than a minute. Read more

Click here to reset your password.
Sign in to get notified via email when new comments are made.