Teflon!

Parul Singh
Polytetrafluoroethylene (PTFE), or better known as teflon is a polymer made from the
monomer tetrafluoroethylene by free radical vinyl polymerisation, the structure is shown
below in diagram 1. The monomer is made by heating chlorodifluoromethane to a very
high temperature1. Teflon was discovered by accident (as some of the most useful
compounds are!) by an American chemist who worked for Dupont, Roy Plunkett, in
1938. Plunkett was using tetrafluoroethylene in a pressurised chamber when there was
no longer any pressure but the same mass he opened the chamber to discover a waxy
white solid, the TFE had polymerised to polytetrafluoroethylene. An important and fairly
unique property of teflon is the fluorine atoms as part of a molecule dont interact with
any other molecules due to the extremely strong carbon to carbon and carbon to fluorine
bonds and for this reason it will repel anything. It is also extremely slippery2. Little did
Plunkett know that he had discovered one of the most useful polymers in the world.!

Tetrafluoroethylene

Polytetrafluoroethylene

The mechanism for the production of PTFE involves breaking a peroxide into alkoxyl
radicals by heating or with UV radiation. The O-O bond is weak and only requires
approximately 125 kJ mol-1 of energy to break and the reaction is exothermic. The alkyl
radical bonds to a molecule of tetrafluoroethene leading to a radical on one of the
carbons. Because of this the molecule undergoes further additions by coupling with
other radicals. !
During the second world war, in 1942 PTFE played a role in the Manhattan project. The
scientists needed something almost completely inert and PTFE was just the thing they
needed to tolerate the highly corrosive uranium hexafluoride gas. Plunketts discovery
helped the creation of the worlds first atomic bomb3. Initially during the war Teflon was
only produced for government use. After the war ended DuPont started testing teflon
coated pans to decide if they were safe for commercial use. Meanwhile a fisherman
Gregoire and his wife had an idea to coat pans with teflon as Gregoire used it to coat
his fishing gear with teflon to stop them from tangling and the results were so good they

decided to start a business in the their own home and eventually in 1956 they formed the
Tefal company and opened up a factory4. The name Tefal is derived from the Tef in teflon
and Al from aluminium from the pans.!
In the medical world, teflon is used to make artificial body parts and ePTFE is a woven
form of PTFE which is a mesh like structure which is porous so it can be impanted in the
body. PTFE isn't usually rejected by the human body which must mean it is fairly safe to
use. However when teflon pans are heated to a high temperature it releases up to 15
different toxic gases which cause flu-like symptoms in humans and a recent study has
shown that there may be a link between thyroid disease, cancer and teflon. This is why
we are told if we scratch a non-stick pan it should be disposed of immediately.!
So in conclusion, even though teflon was discovered by accident, it has come to be one
of the most useful and versatile polymers ever made. From helping create the nuclear
bomb that ended the second world war to saving lives with synthetic body parts, It was
definitely a creation that changed the world.!

!
1 J G Bralla, Handbook of Manufacturing Processes - How Products, Components and
Materials are Made, Industrial Press, 2007, 765.!
2 Chemistry3 Andrew Burrows, John Holman, Andrew Parsons, Gwen Pilling, Gareth
Price!
2 J O Punderson, Fluorocarbon Resins for the Original Polytetrafluoroethylene (PTFE) to
the Latest Melt Processible Copolymers, SPE 1976, 78-94!
4 Ralph Katz Human Side of Managing Technological Innovation - A Collections of
Readings, Oxford University Press 2007, Second Edition, 436-443!