Document qmLZYE68YYNRybwkXRyz2YRaM

FLUORINE CHEMISTRY V Edited, by H D ,r J . H . S|i|im o n s * tuoruie Laboratories, The Pennsylvania Stale College, State College, Pennsylvania 1 . II / uUj V O L U M E I '!ik fer Irif I 1950 ACADEMIC PRESS INC., PUBLISHERS NEW YORK, N. Y. 3008.0001 I , E xhibit 3008 State of Minnesota v. 3M Co., Court File No. 27-CV-10-28862 STATE 07525275 KI.U ORO CA RH O N E AND T H E IR PRO D U CTIO N 407 as it was not then known th at these were nonoily liquids of low viscosity t and that butforane boiled below room temperature. Ethforane was first obtained from the uueatalyzed reaction between fluorine and carbon (17). This substance was obtained by the elec trolysis of aeetforie acid in aqueous solution (26) and also by the passage of methforane and difluorochloromethane through an electric arc (15, 27). Ethforene was also first obtained in this manner. The Catalyzed Reaction between Fluorine and Carbon A fortunate accident enabled the reaction between fluorine and carbon to be conducted without explosions at a temperature sufficiently low so that a mixture of liquid fluorocarbons was obtained (21). This t enabled the isolation of propforane, butforane, pentforane, and hexforane. i The quantities obtained from the first set of experiments were insufficient for precise determination of physical properties. I t was found that mercury was a good catalyst for the reaction and enabled it to proceed smoothly without explosions and with the formation of significant proportions of fluorocarbons boiling higher than methforane. The first use of the catalyst occurred when an amalgamated copper tube was inadvertently used for the reaction. I t was later found that a small amount of any mercury compound added to the carbon served as catalyst (22). The products of the reaction on separation showed 54.5% meth forane, 12.6% ethforane, 8.2% propforane, two butforane fractions of 5.3 and 1.3%, 5.5% cyclic CiFm, 4.4% cyclic CFn , 1.3% CrF M, 5.5% of a mixture boiling 25 to 95, and 1.5% of a mixture boiling 95 to 160. The original isolation and identification of stable fluorocarbons con taining four and more carbon atoms per molecule immediately strongly indicated th a t an entire new field of chemistry would eventually result as further studies were made. This was expressed in the original publi cation as follows; " The substances are colorless and either odorless or very nearly so. They are very stable chemically. M any of the tubes containing these were sealed off while an appreciable pressure of the vapor existed inside. No trace of etching or carbonisation could be observed in the Pyrex glass seal, which must have been at least 700. The different fractions were tested for unsaturation with bromine in carbon tetrachloride solution, and no decolonisation could be observed. The formation of stable compounds of carbon and fluorine containing more than three carbon atoms per molecule indicates the possibility of the synthesis of a large number of similar compounds provided th a t methods can be discovered. Such com pounds should be of considerable interest both theoretically and as useful substances. To indicate the relatively low attractive force between the molecules of these compounds, a graph is shown in the figure. The molecular weight is plotted against the boiling point. On the same graph are represented the inert gases, the bydroear- 3008.0009 STATE 07525283