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United States Patent Office 2,533,133 Replacement of Hydrogen with Fluo

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United States Patent Office 2,533,133 Replacement of Hydrogen with Fluo Patented Dec. 5, 1950 2,533,133 UNITED STATES PATENT OFFICE 2,533,133 REPLACEMENT OF HYDROGEN WITH FLUO. RINE IN HYDROGEN- AND HALOGEN-CON TANING ORGANIC COMPOUNDS USING LEAD TETRAFLUORDE Earl T. McBee, La Fayette, Ind., and Richard M. Robb, Wilmington, Del, assignors to Purdue Research Foundation, West Lafayette, Ind., a corporation of Indiana No Drawing. Application July 4, 1945, Serial No. 603,271 10 Claims. (C. 260-648) This invention relates to fluorine-containing agents, of partially fluorinated organic com Organic compounds and to a method for the prep pounds having fluorine atoms only in desired aration thereof. This application is a continua positions in the molecule is, except in certain in tion in part of application, Serial No. 552,016, Stances, not possible. Furthermore, highly fluo filed August 30, 1944. rinated Organic compounds are not usually ob The preparation of fluorine-containing organic tained readily from the corresponding - highly compounds by replacement of hydrogen in halo chlorinated, brominated or iodinated compounds gen- and hydrogen-containing organic com using such agentS. Certain of the agents referred pounds has heretofore not been accomplished to, e. g., the halogen fluorides, react with many readily. It is well known that elemental fluorine O organic compounds with explosive violence. generally may not be reacted with organic con Most metal fluorides heretofore proposed as pounds to replace hydrogen with fluorine and the agents to replace chlorine, bromine or iodine in reaction controlled so as to produce a desired organic compounds with fluorine are without fluorine-containing compound with any degree of Substantial effect in replacing hydrogen with Satisfaction. Although certain halogens other s fluorine. Furthermore, Such metal fluorides tend than fluorine e. g., chlorine and bromine, may to produce polymerized or unsaturated break react with a wide variety of organic compounds down products and do not usually lead to com under suitable conditions to give high yields of plete or uniform replacement of chlorine, bro valuable products, the reaction of fluorine With nine Oriodine with fluorine. For these and other organic compounds is usually violent in nature 20 reasons fluorine-containing organic compounds, and is accompanied by profound decomposition particularly compounds containing fluorine and of the organic compound. In most cases reaction another halogen, have with few exceptions not occurs with explosive violence in spite of extreme heretofore been available and industry has been measures which may be taken to moderate its ef deprived of many members of this group of com fect. In many instances the reaction productS 25 pounds which, due to their non-flammability and consist mainly of carbonaceous matter and hy to the thermal stability of the more highly fluo drogen fluoride or of other equally undesirable rinated members, are especially valuable. The decomposition products. When using a very need for new and improved procedures for the large excess of fluorine the principal products are preparation of fluorine-containing organic com generally carbon tetrafluoride and hydrogen 30 pounds is evident. fluoride. It is, therefore, an object of the present inven Many attempts have been made to use fluori tion to provide a method for the preparation of nating agents other than elemental fluorine to fluorine-containing organic compounds. Still a replace hydrogen in hydrogen- and halogen-con further object is to provide a method whereby a taining organic compounds and thus to obtain 35 fluorine-containing organic compound may be desired fluorine-containing organic compounds. prepared from a partially chlorinated, bromi Among the fluorinating agents which have been nated or iodinated organic compound. An addi tried may be mentioned hydrogen fluoride, anti tional object is to provide a method whereby a mony trifluoride, mercuric fluoride, iodine penta fluorine-containing organic compound may be fluoride, bromine trifluoride, chlorine trifluoride, 40 prepared from a partially halogenated organic and many others. Although certain of these compound containing two or more different halo agents may, under certain conditions, replace gens. An additional object is to provide a method with fluorine a halogen atom other than fluorine whereby the fluorine content of a partially fluo already in the organic molecule, little success has rinated organic compound may be increased. An been reported in attempting to replace hydrogen 45 additional object is to provide a method whereby with fiuorine using these agents. For this reason hydrogen in hydrogen- and halogen-containing it is usually necessary as a step preliminary to Organic compounds may be replaced with fluo the preparation of a desired fluorine-containing rine. An additional object is to provide a method organic compound to prepare the corresponding for preparing a fluorine-containing organic com chlorine-, bromine- or iodine-containing Com 50 pound whereby the formation of undesirable de pound. This renders processes using these fluori composition or polymerization products is sub nating agents unduly complicated and, also, the stantially avoided. An additional object is to requisite chlorine-, bromine- or iodine-contain provide a fluorination method which is not sub ing compound may not always be prepared read ject to certain of the disadvantages set forth ily. In addition, the preparation, using these 55 above. Still a further object is to provide a 2,588,133 3 4. ra novel fluorinating agent capable of replacing pentafluoromonoiodoethane, dichloroperfluoro hydrogen in halo organic compounds with fluo piperidine, and many others. rine. Still an additional object is to provide new Examples of hydrogen- and fluorine-contain and novel fluorine-containing organic con ing organic compounds which may be fluo pounds, including halocarbons, fluorocarbons and rinated with lead tetrafluoride to form com other highly fluorinated substances. Other ob pounds of increased fluorine content, including jects will become apparent from the following perhalo or perfluoro compounds are, methyl specification and claims. fluoride, trifluoromethane, monochloromono According to the present invention the fore fluoromethane, monobromodifluoroethane, going and related objects are accomplished read 10 monochloropentafluoroheptane, vinylidene fluo ily and economically by contacting an Organic ride, monochloromonofluoroethylene, mono compound containing hydrogen and a halogen fluorobenzene, difluoronaphthalene, monochloro with lead tetrafluoride under suitable reaction monofluorobenzene, benzotrifluoride, '... bis-tri conditions. Lead tetrafluoride has been found fluoromethyl benzene, monofluorocyclo to be an excellent fuorinating agent for hydro 15 hexane, monobronomonochloromonofluorocy gen- and halogen-containing organic con clohexane, fluorocyclohexene, and the like, pounds, and when the reaction is carried out un According to One modification of the inven der conditions hereinafter described it may be tion, perfluorination may be accomplished and controlled without difficulty. Halogen other perfluoro compounds may be obtained by con than fluorine as well as hydrogen in hydrogen 20 tacting an organic compound containing at and halogen-containing organic compounds may least one hydrogen atom and at least one halogen be replaced readily with fluorine so that perhalo atom attached to carbon with lead tetrafluoride organic compounds containing Substantially any as an active fluorinating agent under such con desired proportion of fluorine, including per ditions and for Such time that all of such hydro fluoro compounds, may, if desired, be produced 25 gen and of Such halogen other than fluorine in With the formation of little or no decomposition the molecule is replaced by fluorine. This may or polymerization products. Aliphatic, aro be described as perfluorination. Examples of matic, heterocyclic and alicyclic compounds, in perfuoro organic compounds which may be pre cluding fused-ring compounds and polycarbo pared by the method of the invention include cyclic non-fused-ring compounds, containing 30 carbon tetrafluoride, hexafluoroethane, dodeca hydrogen and a halogen may be fluorinated fluoropentane, dodecafluorocyclohexane, per readily with lead tetrafluoride. fluoromethylcyclohexane, perfluorobicyclohexyl, Unsaturated hydrogen- and halogen-contain perfluorodecahydronaphthalene, perfluorodi ing organic compounds, Such as vinylidene chlo butyl ether, perfuoropiperidine, trifluoroacetyl ride, trichloroethylene, bromobutylene, chlorocy 35 fluoride, and the like. clohexene, monochlorobenzene, dibromobenzene, In certain instances rupture of the molecule iodobenzene, chlorotoluene, chlorobiphenyl, bro may, if desired, be effected with the formation moanthracene, chloronaphthalene and their of fluorine-containing compounds having fewer substitution derivatives may be fluorinated carbon atoms in the molecule than does the orig readily with lead tetrafluoride. In the fluorina 40 inal hydrogen- and halogen-containing organic tion of unsaturated organic compounds replace compound fluorinated. Thus high molecular ment of hydrogen is usually, but not always, ac weight halohydrocarbons may, for example, be companied by or preceded by the addition of converted with lead tetrafluoride largely to high fluorine atoms at the points of unsaturation with molecular weight fluorine-containing halocar the production of saturated fluorine-containing 5 bons, to high molecular weight Saturated fluoro
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