One Man’s Trash, Another Man’s Treasure
USC Dornsife chemist G.K. Surya Prakash and his team discover a way to turn a harmful byproduct of Teflon — used on everything from cooking pans to armor-piercing bullets — into material for pharmaceuticals.
A team of USC Dornsife chemists has developed a way to transform a hitherto useless ozone-destroying greenhouse gas that is the byproduct of Teflon manufacture into reagents for producing pharmaceuticals.
The discovery was published in a paper titled, “Taming of Fluoroform (CF3H): Direct Nucleophilic Trifluoromethylation of Si, B, S and C Centers,” in the Dec. 7 issue of Science. The method is also being patented.
Because of the popularity of Teflon — used on everything from cooking pans to armor-piercing bullets — there’s no shortage of its waste byproduct, fluoroform. Major chemical companies, such as DuPont, Arkema Inc., and others, have huge tanks of it and are unable to simply release it because of the potential damage to the environment. Fluoroform has an estimated global warming potential 11,700 times higher than carbon dioxide.
But one man’s trash is another man’s treasure, and G.K. Surya Prakash — who has spent decades working with fluorine reagents — saw the tanks of fluoroform as an untapped opportunity.
Prakash, Professor and George A. and Judith A. Olah Nobel Laureate Chair in Hydrocarbon Chemistry in USC Dornsife, and director of the USC Loker Hydrocarbon Research Institute, describes fluorine as “the kingpin of drug discovery.” About 20 to 25 percent of drugs on the market today contain at least one fluorine atom; fluorine can be found in many drugs, from 5-Fluorouracil (a widely used cancer treatment discovered by Charles Heidelberger at USC in the ’70s) to Prozac to Celebrex.
“It’s a small atom with a big ego,” Prakash said, referring to the fact that while fluorine is about the same size as a tiny hydrogen atom — so similar that living cells cannot tell the two elements apart — it is also extremely electronegative (that is, it has a strong attraction for electrons) making carbon-fluorine chemical bond quite strong, which improves the bioavailability of drugs made with fluorine.
Prakash led a team that included longtime colleague Nobel laureate George Olah, Donald P. and Katherine B. Loker Distinguished Professor of Organic Chemistry, and research associates Parag Jog and Patrice Batamack of USC Dornsife.
The discovery was the product of many years of trial-and-error tests, hard work that the postdocs performed under Prakash’s direction. Eventually, the team pinned down the precise conditions needed to coax the harmful fluoroform (CF3H) into useful reagents, including the silicon-based Ruppert-Prakash Reagent for efficient CF3 transfer. Fluoroform with elemental sulfur was also converted to trifluoromethanesulfonic acid, a widely used superacid 100 times stronger than sulfuric acid.
“In real estate, everything is ‘location, location, location,’ Prakash said. “In chemistry, it is ‘conditions, conditions, conditions.’ ”
The research was funded by the Loker Hydrocarbon Research Institute.
Related News Items
- Just Getting Warmed Up March 3, 2015
- Irani Pledges Support for Residential College March 2, 2015
- Unlocking Pain Relief February 20, 2015
- On Our Best Behavior February 20, 2015
- Waterman Awarded Prestigious Dan David Prize February 11, 2015
- Better Cures, Better Care February 5, 2015
- Partners in Sustainability and Environmental Studies February 3, 2015
- Thompson Hailed as Innovator December 16, 2014
- Diagnosis Success December 4, 2014
- Recognition for Pratt’s Work November 18, 2014
- Small in Stature, Big on Health November 13, 2014
- Mechanics of String Theory November 6, 2014
- Collaboration in 3-D October 28, 2014
- Michelson Center for Convergent Bioscience Ushers in New Era October 23, 2014
- USC Dornsife Recruits Renowned Leaders in Molecular Research October 23, 2014
- Golgi Your Brain October 20, 2014
- Big Boost for the Bench October 9, 2014
- In Their Own Words October 8, 2014
- Sugar Linked to Memory Woes October 7, 2014
- Chemists Dispel Long-held Notion September 26, 2014