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“Fluorocarbons” “Fluorocarbons” -Alex J. Roche A Graduate Level Advanced Organic Course Rutgers, The State University of New Jersey 56:160:519 Office: Sci 311 Labs: Sci 309, 328F, 304A [email protected] Tel: (856) 225-6166 Fax: (856) 225-6506 http://crab.rutgers.edu/~alroche/ “Fluorine leaves nobody indifferent; it inflames emotions be that affections or aversions. As a substituent, it is rarely boring, always good for a surprise, but often completely unpredictable” – Manfred Schlosser, 1998. 1 Fluorocarbons Fluorocarbons are organic compounds that contain fluorine, and they are (almost always) synthetic or man made compounds. Compounds bearing a C-F bond do not occur in nature (almost true). Thus the replacement of a C-H bond with a C-F bond gives rise to a potentially vast man made organic chemistry. Adds an entirely synthetic extra dimension to Organic Chemistry. Fluorocarbons can Provide: New Chemistry Unique Chemistry (Special Effects) New materials New Applications 2 Organofluorine Chemists (should) Aim to: -Develop the Organic Chemistry of compounds that contain Fluorine -Encourage application by collaboration with industry -Integrate the subject on a mechanistic basis with modern organic chemistry (get to a level of understanding so F is predictably unique) 3 History Hydrogen Fluoride was first reported by Scheele in 1771. The first reported synthesis of an organofluorine compound was in 1836, when Dumas and Peligot reported the synthesis of fluoromethane. It was in 1886 that Henri Moissan prepared and isolated molecular elemental fluorine gas (F2). Moissan in 1890 erroneously reported the isolation of carbon tetrafluoride as a product of the reaction of fluorine and carbon. It was the Belgian chemist Swarts’ work between 1890 and 1938 on simple aliphatic fluorocarbons which is widely considered as establishing the foundations of organofluorine chemistry. In the 1930’s, Midgley and Henne extended Swarts’ exchange reaction methods and this promoted the introduction of CFC’s (chlorofluorocarbons) as refrigerants. 4 History cont The chemistry of perfluorinated (fully fluorinated) organic compounds began in 1926 when Lebeau and Damiens synthesized carbon Tetrafluoride. This compound was fully characterized in 1930 by the above workers, and also by Ruff and Kleim in the same year. Pre-1930, household refrigerators used methyl chloride and ammonia as their coolant. In the 1930’s, it was discovered that dichlorodifluoromethane was a safe, stable gas whose liquefied state had low compressibility, and importantly, was not flammable. Dupont and General Motors were the pioneers of the application of CFCs as refrigerants. Later CFC’s would find diverse applications as inert gases, blowing agents, cleaning agents and chemical reagents (monomers). Another important event in the growth of fluorine chemistry was the Second World War.The development of the atomic bomb meant extensive research into Uranium. 5 The desired isotope of Uranium was 235U. The best way to separate the different isotopes of Uranium is gaseous diffusion separation (lighter ones travel faster). The best compound for this was UF6. The enriched UF6 is converted to the oxide which is used as the fuel for nuclear power. Interest in UF6 spawned two major areas of development for fluorine chemistry: One was the ability to handle F2 gas effectively, since UF6 is made by fluorination of UF4, which itself is made by fluorination with elemental fluorine. Secondly, UF6 is extremely reactive, and in order to safely handle this material, unreactive materials needed to be created. The Manhattan Project during WWII successfully developed a family of fluorine containing compounds which could be used for UF6 handling and equipment. 6 Such early materials form the basis of the current fluorochemical and fluoropolymer material industries. Starting in the 1970’s, concern over the detrimental environmental effects of accumulating CFC emissions into the atmosphere, led to the formation of The Montreal Protocol on Substances That Deplete the Ozone Layer, which is phasing out the production and use of ozone depleting CFC’s. The search for CFC replacements like HCFC’s and HFC’s are thus a current hot research area. 7 -Fluorine Chemistry Statistics Bruce E. Smart in Chemical Reviews, 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”. Fluorine Chemistry is a relatively new and growing area of chemistry. In 1990, Wilkinson and Seebach determined that 6.2% of all compounds registered in chemical abstracts contained at least one C-F bond. Figures from their data up to 1990 are shown on the next slide: 8 9 10 11 Schofield produced figures for the last ten years concerning new C-F containing compounds and publications. 12 During 1989 - 1998 a total of 610,873 new C-F containing compounds were registered with the Chemical Abstracts Service. The figures for publications concerning C-F compounds are shown below: (Typically around 30% of publications are patents). (Typically around 30% of publications are patents). 13 To put this into perspective with the rest of chemistry: (The downward trend from 1994 is perhaps due to the massive increase in numbers of compounds generated by combinatorial chemistry methods). 14 Fluorocarbons around us Many fluoroorganic compounds are encountered on a daily basis. This is generally not appreciated either by the general public and also (probably) by the scientific community. Consider an average morning: You wake up and walk across your (Scotchguard protected) carpet to the kitchen to have breakfast, take the milk out of your (CFC/HFC cooled) fridge, fry your eggs on your (non-stick Teflon coated) frying pan, brush your teeth with fluoride toothpaste, take your medication of choice (prozac / 5FU / efavirenz / flurbiprofen), get dressed and grab your (Gore-Tex rain proof) coat, walk across your (treflan / fusillade treated) lawn to your car which has a plastic (surface fluorinated) petrol / gas tank....etc, etc 15 Naturally Occurring Organofluorine compounds To date (2000) there have been over 3,000 natural products characterized which contain chlorine, bromine or iodine. Currently there are 13 known to contain a carbon fluorine bond. Most of these are tropical plant metabolites found in the southern hemisphere, and the presence of such compounds makes the plants acutely toxic. For example traces of fluoroacetic acid found in the plant, gifblaar (Dichapetalum cymosum) in the South African veldt are believed to be responsible for numerous cattle deaths from errant grazing. It seems that nature (one of the best chemists around) does not seem to specialize in fluorine chemistry. This is not due to a lack of natural resources since Fluorine is the 13th most abundant element in the earth’s crust. (Fluorspar – mainly CaF2) 16 There is not really a very good explanation for this; the best offered so far are: a) the fluoride ion is generally only available in insoluble mineral forms b) no enzyme with fluorinating activity has been found yet. This is conjectured to be related to the fact that fluoride ion is superbly solvated in aqueous media, and that electrophilic or radical fluorination mechanisms are unlikely). (So basically nature needs the fluoride ion needs to be a nucleophile in aqueous solution, but generally the sources are insoluble, and even the soluble ones provide a fluoride ion so well solvated it is a terrible nucleophile). .....In 2002 Discovered in 2002 5’-fluoro-5’-deoxyadenosine synthase, trivially termed the “fluorinase” O'Hagan D, Schaffrath C, Cobb SL, Hamilton JT, Murphy CD. Biochemistry: biosynthesis of an organofluorine molecule. Nature. 2002 Mar 21;416(6878):279. 17 • NEWS OF THE WEEK BIOSYNTHESIS March 25, 2002 Volume 80, Number 12 CENEAR 80 12 p. 11 ISSN 0009-2347[Previous Story] [Next Story] • First Fluorinase Enzyme Discovered • STEVE RITTER - Fluorine is the most chemically reactive of all the elements. The flip side to that property is that fluorine forms extremely stable compounds. • For example, even though fluorine is the most abundant halogen in Earth's crust, most of the element is tied up in insoluble fluoride minerals. That means naturally occurring organofluorine compounds are rare--only 12 have been discovered--and how these compounds are biosynthesized is largely unknown. • Chemistry professor David O'Hagan and graduate student Christoph Schaffrath of the University of St. Andrews, in Scotland, and coworkers have now found a clue by uncovering the first known fluorinase enzyme [Nature, 416, 279 (2002)]. • The researchers show that the fluorinase can catalyze carbon-fluorine bond formation between an organic substrate and fluoride ion. 18 • They studied the enzymatic fluorination by incubating a protein extract from Streptomyces cattleya with potassium fluoride and S-adenosylmethionine (shown). The initial product is 5´-fluoro-5´-deoxyadenosine, which is further – converted by other enzymes to fluoroacetate, FCH2CO2 . Fluoroacetate, which has been identified in more than 40 plant species, is the most ubiquitous of the known natural organofluorine compounds. • Although chemists have developed a number of synthetic strategies to prepare organofluorine compounds, discovery of the fluorinase enzyme "opens up a new biotechnological opportunity," O'Hagan says, and could have broad applications in medicinal chemistry. 19 Prof. David O’Hagan University of St. Andrews Research at Centre for Biomolecular Sciences Chairman of Royal Society of Chemistry, Fluorine Subject Group 20 Poland 2004. (Durham Connections) 21 22 23 24 25 26 27.
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