Du Pont Central Research - Organofluorine Chemistry

Organofluorine Chemistry

On April 6, 1938, Roy Plunkett at DuPont’s Jackson Laboratory in New Jersey was working with gases related to DuPont’s Freon refrigerants when he and his associates discovered that a sample of gaseous tetrafluoroethylene had polymerized spontaneously into a white, waxy solid. The polymer was polytetrafluoroethylene (PTFE) commercialized by DuPont as Teflon in 1945. Because DuPont was basic in a variety of fluorinated materials, it was logical that organofluorine chemistry became important to DuPont. The discovery that tetrafluorethylene would cyclize with a wide variety of compounds to give fluorinated compounds opened up routes to a range of organofluorine compounds.

The hazards and difficulties of handling highly reactive and corrosive fluorinating reagents could be accommodated by DuPont’s emphasis on safety and DuPont’s association with the Manhattan Project provided many chemists and engineers with the background necessary to carry out the work. Availability of the Pressure Research Lab on the Experimental Station provided the necessary protection for most but not all of those reactions that went awry. Notable scientists included William Middleton, David England, Carl Krespan, William Sheppard, Owen Webster, Bruce Smart, Malli Rao, Robert Wheland, and Andrew Feiring, all of whom filed many patents for DuPont. Sheppard wrote one of the important early books on the subject. Smart's book followed. Smart’s comments in Chemical Reviews in 1996, “Scientific and commercial interests in fluorine chemistry burgeoned after 1980, largely fueled by the need to replace industrial chlorofluorocarbons and the rapidly growing practical opportunities for organofluorine compounds in crop protection, medicine and diverse materials applications. Although fluorine is much less abstruse now than when I entered the field a generation ago, it remains a specialized topic and most chemists are unfamiliar, or at least uncomfortable, with the synthesis and behavior of organofluorine compounds,” remain true today.

CRD undertook a program on alternatives for chlorofluorocarbons in refrigerants in the late 1970s after the first warnings of damage to stratospheric ozone were published. The Catalysis Center of CRD, under the leadership of Leo Manzer, was quick to respond with new technology to produce alternative hydrochlorofluorocarbons (HCFCs) that were commercialized as DuPont's Suva refrigerants.