Hydrocarbons fluorination

Nitric oxide Aluminum, BaO, boron, carbon disulflde, chromium, many chlorinated hydrocarbons, fluorine, hydrocarbons, ozone, phosphine, phosphorus, hydrazine, acetic anhydride, ammonia, chloroform, Fe, K, Mg, Mn, Na, sulfur... 

One major use of HF is in the manufacture of fluorinated hydrocarbons. Fluorinated ethylene is used for several specialty polymers. For example, the Teflon coating on nonstick cookware is made from polytetrafluoroethylene (PTFE). This polymer is made from tetrafluoroethylene. 

See Bromine pentafluoride Hydrogen-containing materials Chlorine trifluoride Methane Chlorine Hydrocarbons Fluorine Hydrocarbons Iodine heptafluoride Carbon, etc. 

Finally, PNDO has been used to calculate the dipole moments of some saturated hydrocarbons with reasonable agreement with experiment. In Table 18 we show the values obtained by each method for small molecules of the general form AB, ABz and ABz- In Tables 19 to 23 we show the values obtained by each method for hydrocarbons, fluorine-containing compounds, oxygen-containing compounds, nitrogen-containing compounds and other miscellaneous compounds. In Fig. 3 and 4 we compare, where possible, these values, to the experimentally observed ones. 

Water absorption is less than 0.1wt% after 24 hours. However, PBT is not recommended for extended use in water or aqueous solutions above 52C (125F).112 PBT plastics are also intrinsically resistant to detergents, weak acids and bases, aliphatic hydrocarbons, fluorinated hydrocarbons, alcohols, ketones, ethylene glycol, carbon tetrachloride, oils, and fats at room temperature. They also exhibit good resistance to motor oil, gasoline, transmission fluids, and brake fluids at temperatures to 60C (HOF).113... 

FLUORINATED HYDROCARBONS. Fluorinated hydrocarbons are the most stable halogenated hydrocarbons and the most compatible with aluminum alloys. They have been used as propellants and refrigerants in contact with aluminum alloys in many applications. See "Freon and Halogenated Hydrocarbons."... 

The lubricant properties of alkanethiols and fluorinated alkanes have been studied extensively by scanning probe techniques [163]. In agreement with experiments on LB monolayers it was found that the fluorocarbon monolayers show considerably higher friction than the corresponding hydrocarbon monolayers [164, 165 and 166] even though the fluorocarbons are known to have the lowest surface free energy of all organic materials. 

Many of the reactions of halogens can be considered as either oxidation or displacement reactions the redox potentials (Table 11.2) give a clear indication of their relative oxidising power in aqueous solution. Fluorine, chlorine and bromine have the ability to displace hydrogen from hydrocarbons, but in addition each halogen is able to displace other elements which are less electronegative than itself. Thus fluorine can displace all the other halogens from both ionic and covalent compounds, for example... 

Chlorine Ammonia, acetylene, alcohols, alkanes, benzene, butadiene, carbon disulflde, dibutyl phthalate, ethers, fluorine, glycerol, hydrocarbons, hydrogen, sodium carbide, flnely divided metals, metal acetylides and carbides, nitrogen compounds, nonmetals, nonmetal hydrides, phosphorus compounds, polychlorobi-phenyl, silicones, steel, sulfldes, synthetic rubber, turpentine... 

CoF is used for the replacement of hydrogen with fluorine in halocarbons (5) for fluorination of xylylalkanes, used in vapor-phase soldering fluxes (6) formation of dibutyl decalins (7) fluorination of alkynes (8) synthesis of unsaturated or partially fluorinated compounds (9—11) and conversion of aromatic compounds to perfluorocycHc compounds (see Fluorine compounds, organic). CoF rarely causes polymerization of hydrocarbons. CoF is also used for the conversion of metal oxides to higher valency metal fluorides, eg, in the assay of uranium ore (12). It is also used in the manufacture of nitrogen fluoride, NF, from ammonia (13). 

Substitution of fluorine for hydrogen in an organic compound has a profound influence on the compound s chemical and physical properties. Several factors that are characteristic of fluorine and that underHe the observed effects are the large electronegativity of fluorine, its small size, the low degree of polarizabiHty of the carbon—fluorine bond and the weak intermolecular forces. These effects are illustrated by the comparisons of properties of fluorocarbons to chlorocarbons and hydrocarbons in Tables 1 and 2. 

Initial attempts at reactions between fluorine and hydrocarbons were described as similar to combustion and the reaction products contained mostly carbon tetrafluoride and hydrogen fluoride ... 

This reaction has often reached explosive proportions in the laboratory. Several methods were devised for controlling it between 1940 and 1965. For fluorination of hydrocarbons of low (1—6 carbon atoms) molecular weight at room temperature or below by these methods, yields as high as 80% of perfluorinated products were reported together with partially fluorinated species (9—11). However, fluorination reactions in that eta involving elemental fluorine with complex hydrocarbons at elevated temperatures led to appreciable cleavage of the carbon—carbon bonds and the yields invariably were only a few percent. 

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