Featured Research

from universities, journals, and other organizations

Breakthrough could lead to cheaper, more sustainable chemical production

Date:
March 21, 2013
Source:
Brown University
Summary:
A new advance could enable the production of an important commodity chemical using carbon dioxide as a carbon source instead of petroleum. Carbon dioxide is basically free, and something the planet currently has in excess. Activating carbon dioxide for the production of commodity chemicals could be a way make them more cheaply and sustainably.

A possible use for excess carbon: In the presence of nickel and other metal catalysts, CO2 and ethylene gas form an acrylate precursor configured in a five-membered ring. The challenge has been to crack that ring open, allowing a carbon-carbon double bond to form, creating acrylate. Lewis acids do the trick.
Credit: Berkskoetter lab/Brown University

A key advance, newly reported by chemists from Brown and Yale Universities, could lead to a cheaper and more sustainable way to make acrylate, an important commodity chemical used to make materials from polyester fabrics to diapers.

Chemical companies churn out billions of tons of acrylate each year, usually by heating propylene, a compound derived from crude oil. "What we're interested in is enhancing both the economics and the sustainability of how acrylate is made," said Wesley Bernskoetter, assistant professor of chemistry at Brown, who led the research. "Right now, everything that goes into making it is from relatively expensive, nonrenewable carbon sources."

Since the 1980s researchers have been looking into the possibility of making acrylate by combining carbon dioxide with a gas called ethylene in the presence of nickel and other metal catalysts. CO2 is essentially free and something the planet currently has in overabundance. Ethylene is cheaper than propylene and can be made from plant biomass.

There has been a persistent obstacle to the approach, however. Instead of forming the acrylate molecule, CO2 and ethylene tend to form a precursor molecule with a five-membered ring made of oxygen, nickel, and three carbon atoms. In order to finish the conversion to acrylate, that ring needs to be cracked open to allow the formation of a carbon-carbon double bond, a process called elimination.

That step had proved elusive. But the research by Bernskoetter and his colleagues, published in the journal Organometallics, shows that a class of chemicals called Lewis acids can easily break open that five-membered ring, allowing the molecule to eliminate and form acrylate.

Lewis acids are basically electron acceptors. In this case, the acid steals away electrons that make up the bond between nickel and oxygen in the ring. That weakens the bond and opens the ring.

"We thought that if we could find a way to cut the ring chemically, then we would be able to eliminate very quickly and form acrylate," Bernskoetter said. "And that turns out to be true."

He calls the finding an "enabling technology" that could eventually be incorporated in a full catalytic process for making acrylate on a mass scale. "We can now basically do all the steps required," he said.

From here, the team needs to tweak the strength of the Lewis acid used. To prove the concept, they used the strongest acid that was easily available, one derived from boron. But that acid is too strong to use in a repeatable catalytic process because it bonds too strongly to the acrylate product to allow additional reactions with the nickel catalyst.

"In developing and testing the idea, we hit it with the biggest hammer we could," Bernskoetter said. "So what we have to do now is dial back and find one that makes it more practical."

There's quite a spectrum of Lewis acid strengths, so Bernskoetter is confident that there's one that will work. "We think it's possible," he said. "Organic chemists do this kind of reaction with Lewis acids all the time."

The ongoing research is part of a collaboration between Brown and Yale supported by the National Science Foundation's Centers for Chemical Innovation program. The work is aimed at activating CO2 for use in making all kinds of commodity chemicals, and acrylate is a good place to start.

"It's around a $2 billion-a-year industry," Bernskoetter said. "If we can find a way to make acrylate more cheaply, we think the industry will be interested."

Other authors on the paper were Dong Jin and Paul Willard of Brown and Nilay Hazari and Timothy Schmeier of Yale.


Story Source:

The above story is based on materials provided by Brown University. Note: Materials may be edited for content and length.


Journal Reference:

  1. Dong Jin, Timothy J. Schmeier, Paul G. Williard, Nilay Hazari, Wesley H. Bernskoetter. Lewis Acid Induced β-Elimination from a Nickelalactone: Efforts toward Acrylate Production from CO2 and Ethylene. Organometallics, 2013; 130321123314001 DOI: 10.1021/om400025h

Cite This Page:

Brown University. "Breakthrough could lead to cheaper, more sustainable chemical production." ScienceDaily. ScienceDaily, 21 March 2013. <www.sciencedaily.com/releases/2013/03/130321151935.htm>.
Brown University. (2013, March 21). Breakthrough could lead to cheaper, more sustainable chemical production. ScienceDaily. Retrieved July 25, 2014 from www.sciencedaily.com/releases/2013/03/130321151935.htm
Brown University. "Breakthrough could lead to cheaper, more sustainable chemical production." ScienceDaily. www.sciencedaily.com/releases/2013/03/130321151935.htm (accessed July 25, 2014).

Share This




More Matter & Energy News

Friday, July 25, 2014

Featured Research

from universities, journals, and other organizations


Featured Videos

from AP, Reuters, AFP, and other news services

TSA Administrator on Politics and Flight Bans

TSA Administrator on Politics and Flight Bans

AP (July 24, 2014) TSA administrator, John Pistole's took part in the Aspen Security Forum 2014, where he answered questions on lifting of the ban on flights into Israel's Tel Aviv airport and whether politics played a role in lifting the ban. (July 24) Video provided by AP
Powered by NewsLook.com
Creative Makeovers for Ugly Cellphone Towers

Creative Makeovers for Ugly Cellphone Towers

AP (July 24, 2014) Mobile phone companies and communities across the country are going to new lengths to disguise those unsightly cellphone towers. From a church bell tower to a flagpole, even a pencil, some towers are trying to make a point. (July 24) Video provided by AP
Powered by NewsLook.com
Algonquin Power Goes Activist on Its Target Gas Natural

Algonquin Power Goes Activist on Its Target Gas Natural

TheStreet (July 23, 2014) When The Deal's Amanda Levin exclusively reported that Gas Natural had been talking to potential suitors, the Ohio company responded with a flat denial, claiming its board had not talked to anyone about a possible sale. Lo and behold, Canadian utility Algonquin Power and Utilities not only had approached the company, but it did it three times. Its last offer was for $13 per share as Gas Natural's was trading at a 60-day moving average of about $12.50 per share. Now Algonquin, which has a 4.9% stake in Gas Natural, has taken its case to shareholders, calling on them to back its proposals or, possibly, a change in the target's board. Video provided by TheStreet
Powered by NewsLook.com
Robot Parking Valet Creates Stress-Free Travel

Robot Parking Valet Creates Stress-Free Travel

AP (July 23, 2014) 'Ray' the robotic parking valet at Dusseldorf Airport in Germany lets travelers to avoid the hassle of finding a parking spot before heading to the check-in desk. (July 23) Video provided by AP
Powered by NewsLook.com

Search ScienceDaily

Number of stories in archives: 140,361

Find with keyword(s):
Enter a keyword or phrase to search ScienceDaily for related topics and research stories.

Save/Print:
Share:

Breaking News:
from the past week

In Other News

... from NewsDaily.com

Science News

    Health News

      Environment News

        Technology News



          Save/Print:
          Share:

          Free Subscriptions


          Get the latest science news with ScienceDaily's free email newsletters, updated daily and weekly. Or view hourly updated newsfeeds in your RSS reader:

          Get Social & Mobile


          Keep up to date with the latest news from ScienceDaily via social networks and mobile apps:

          Have Feedback?


          Tell us what you think of ScienceDaily -- we welcome both positive and negative comments. Have any problems using the site? Questions?
          Mobile: iPhone Android Web
          Follow: Facebook Twitter Google+
          Subscribe: RSS Feeds Email Newsletters
          Latest Headlines Health & Medicine Mind & Brain Space & Time Matter & Energy Computers & Math Plants & Animals Earth & Climate Fossils & Ruins