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UNITED STATES PATENT of FICE 2,530,369 OX DATION of AROMATC COMPOUNDS Joseph H

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UNITED STATES PATENT of FICE 2,530,369 OX DATION of AROMATC COMPOUNDS Joseph H Patented Nov. 21, 1950 2,530,369 UNITED STATES PATENT of FICE 2,530,369 OX DATION OF AROMATC COMPOUNDS Joseph H. Simons, State College, Pa., assignor to Phillips Petroleum Company, a corporation of Delaware No Drawing. Application January 29, 1948, Serial No. 5,205. 20 Claims. (C. 260-621) 1. This invention relates to the oxidation of aro Essentially, the process of the present inven matic compounds, and more particularly to a new tion comprises oxidizing an aromatic hydrocar process for the oxidation of aromatic hydrocar bon with an oxidizing agent at temperatures bons whereby phenolic products are formed in ranging from 0 C. to 200° C. in the presence of high yield and substantially all of the carbon liquid hydrogen fluoride. containing products other than phenolic con Very high yields of phenolic compounds are tain the same carbon ring structure as the re obtained to the exclusion of products typical of actant. side chain oxidations which are formed in neg In the past, Several processes have been pro ligible amount when such hydrocarbons as tolu posed for production of aromatic ring substitut O ene, Xylene, methyl naphthalene and the like are ed hydroxy (phenolic) compounds by partial utilized as reactants. Furthermore, the forma Oxidation of aromatic hydrocarbons. Such proc tion of typical ring rupture products, such as ali esses employ a wide variety of methods in which phatic compounds, and gaseous products of rel the oxidations are conducted principally in the atively complete combustion, i. e., carbon diox gaseous phase, with and without catalysts or 5 ide and carbon monoxide are not produced in Contact surfaces. In all Such processes, high substantially all instances. temperatures must be employed i. e., tempera One of the principal advantages of the pres tures greatly in excess of 200° C., as evidenced ent invention resides in the use of liquid hy. by the following United States patents: Bibb drogen fluoride in the reaction medium which No. 1,547,725 (700° C.), Hale No. 1595,299 20 causes ring oxidation to occur in preference to (greater than 300° C.), Bone et al. No. 2,199,585 side chain oxidation. (200-400° C.), Moyer et al. Nos. 2,223,393 It is believed that the oxidation reaction pro (325-800° C.) and 2,328,920 (650° C.). Further Ceeds as follows: Hydrogen fluoride activates the more, these processes result in the formation of hydrogen on the ring of the aromatic compound undesired by-products such as those produced 2 5 more than on a side chain. The strong dehy by ring rupture, side chain oxidations and rela drating action of the hydrogen fluoride tends to tively complete combustion, for example, ali favor the oxidation. This oxidation in the pres phatic acids, aromatic aldehydes, and particu ence of hydrogen fluoride seems also to be un larly gases such as Carbon dioxide, carbon mon usual in that the oxides of carbon and products oxide. Inflammable gaseous hydrocarbons and 30 which would normally result from the breaking tars are often formed as a result of cracking at of the aromatic ring are not produced. the high temperatures employed. Another distinct advantage flowing from the All such prior art processes are limited in their use of liquid hydrogen fluoride is that the re application to the use of either benzene or ben action will proceed effectively and result in theo Zene and toluene as reactants. In addition, with retical and near theoretical yields of phenolic a single exception (Moyer et al. Nos. 2,223,393 products even at comparatively low tempera and 2,328,920), all of the processes as applied tures within the range above set forth. This to toluene result in oxidation of the alkyl side eliminates the formation of tars and inflammable chain to produce benzyl alcohol, benzaldehyde lower aliphatic hydrocarbon gases commonly and benzoic acid (see Bone et al. 2,199,585) 40 produced by cracking and ring rupture in the rather than formation of cresols. prior art processes where much higher temper Of course, there are many existing processes atures are employed. In fact, the process of the wherein higher homologues of benzene and the like are oxidized to produce products typical of present invention cannot be operated at temper side chain oxidation, such as benzyl alcohol, al atures above 230 C. regardless of the pressure dehydes, and mono and dicarboxylic acids. How of the System since this temperature is the crit ever, such oxidations occur much more readily ical temperature of hydrogen fluoride and the than those involving introduction of an oxy reaction involves the use of hydrogen fluoride group into the nucleus of an aromatic hydro in the liquid phase. carbon. This invention is concerned primarily 50 A further unexpected result characterizing the with the latter type of oxidation. process of this invention is that the so-called According to the present invention, it has been complete combustion products or more properly discovered that aromatic hydrocarbons are ox the end products are a valuable activated carbon idized to predominantly phenolic products in containing the ring structure of the aromatic high yield in the presence of liquid hydrogen 55 hydrocarbon reactant and water. Thus, if the fluoride, and that the carbon-containing by reaction is carried out attemperatures approach products, if any are formed, contain the same ing the maximum for the process, and the re carbon ring structure of the reactant with little action time is prolonged, the hydrocarbon will or no oxidation of side chains if such are eventually be oxidized completely to such acti present, 80 vated carbon and water. The formation of such 8,880,868 3 4. A product as activated carbon in such an oxida uranium, tungsten, manganese, chromium, copa tion process is unusual and striking. per, etc.; selenic acid, arsenic acid, etc. Although It has further been found that the only prod the carrier is frequently added as the element ucts resulting from the process as applied to Or oxide, the fluorides or oxyfluorides are certain non-aromatic compounds are activated carbon ly present in most cases due to the action of and water. This novel method of producing the anhydrous hydrogen fluoride. Because of the activated carbon from non-aromatic compounds oxidizing action of the oxygen or other oxidizing is disclosed and claimed in my copending applica agent present and also due to the reducing action tion Serial No. 424,214, filed December 23, 1941, . of the Organic Substance, the valence of the now U. S. Patent 2,458,107, issued January 4, 1949. 0. oxygen carrier is afforded an opportunity to re The carbon formed is an absorbing or activated versibly change. char which does not require further processing It thus makes little difference in what chemical for activation. As a rule such activated chars form the oxygen carrier is used. For example, cannot be prepared by oxidation of hydrocarbons, the silver may be added either as the metal, the but result from dehydration of carbohydrates. oxide, the fluoride, the bromide, etc., while the In addition to the phenolic compounds, other arsenic may be added as arsenious acid, arsenic products which are in some instances formed acid, or the salts of either of these acids, in the process of the invention include plural arsenious oxide, arsenic oxide, arsenic trichloride, ring systems, such as diphenyl, ditolyl, di and arsenic pentachloride, arsenic trifluoride, arsenic tri naphthyls, di and tri xylyls. 20 pentafluoride, or as any of the oxychlorides, The formation of benzoic acid in the process bromides, fluorides, etc. in some cases where benzene is employed appears Although the addition of an oxygen carrier is to be extremely noteworthy. It is believed that preferred it is not essential for carrying out the this aromatic monocarboxylic acid has never be oxidation process since the oxidation reaction fore been synthesized by oxidation of benzene. will take place in the absence of any added oxygen This formation of benzoic acid was the only in carrier. Because of the extremely wide range stance in which compounds other than those of substances that may be used as oxygen car having the same carbon ring structure as the riers, it is believed, as above stated, that these initial reactants are formed. It is thought that - Substances act as a means of transporting the the hydrogen fluoride activates the hydrogen 30 oxidation properties of the oxygen source to the atoms on the benzene ring to the point of re molecules of the aromatic compound to be moval, which results in the formation of diphenyl oxidized and, therefore, that any substance which between two adjacent benzene molecules. One can reversibly undergo a valence change in the ring of the diphenyl thus formed is ruptured same reaction medium can serve in this capacity. leading to the formation of benzoic acid. The SS For example, silver can both dissolve the oxygen by-products occurring with benzoic acid were not and carry it in the dissolved condition to the identified except that in every case where it aromatic compound, or it can form silver oxide, formed, diphenyl was found to be present. How fluoride or oxyfluoride with the attendant valence ever, it is not intended to limit the invention to change and thus carry the oxidizing property. the foregoing mechanism or any other theory 40 The arsenic compounds, for example, can undergo of action, it being sufficient to state that in some the valence change from the three to the five instances where the yield of phenolic compounds valent forms and vice versa, thus serving as the is not 100%, benzoic acid is formed from benzene.
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