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United States Patent Office Patented Oct 3,405,171 United States Patent Office Patented Oct. 8, 1968 1. 2 3,405,171 is oxidized to quinone. It is noted that the red-brown OXDATION OF ALKYLNAPHTHALENESTO color of the NO, fades out, and the NO formed in the NAPHTHALENE CARBOXYLCACDS reaction together with water of reaction are removed, Edward S. Roberts, 874 Woodward Ave., Ridgewood, N.Y. the water condensed and the NO reoxidized for return 1227, and Ludwig J. Christmann, 9 Center Knolis, 5 to the reaction. Bronxville, N.Y. 10708; Louise Christmann, adminis Applicants have found that for practical purposes the tratrix of the estate of said Ludwig J. Christmann, deceased temperature of the reaction should be above about 125 No Drawing. Continuation of application Ser. No. 140° C. Preferably, temperatures in the neighborhood of 194,200, May 11, 1962. This application July 27, 180°-225 C. are used, but the temperature should be 1966, Ser. No. 568,348 0. kept below the decomposition point of the substances in 4. Claims. (C. 260-524) volved in the reactions. Also, it is preferable that the concentration of acenaphthene be low, as this insures This application is a continuation of application Ser. that loss of ingredients by side reactions is practically No. 194,200, filed May 11, 1962, by the present in eliminated. Ventors. Such solvents as are suitable for the process must be The present invention is directed in one embodiment inert to nitrogen oxides at the elevated temperatures nec to the production of oxidized organic compounds. essary for the process. The boiling points thereof should One aspect of the invention involves oxidation of alkyl be substantially above the temperatures of the reaction aromatic compounds to aromatic carboxylic acids. An at the pressures used in the operation. Relatively few sol other aspect of the invention involves oxidation of poly 20 vents meet these requirements and, after considerable ex cyclic aromatic compounds to aromatic ketones. perimentation, it was found that the following solvents, In one embodiment, the invention is directed to the which show a negligible reaction with NO2, are suitable: oxidation of acenaphthene and substitution products Mixed tetrachlorobenzenes. thereof wherein the substituents do not interfere with Trichlorobenzene. the oxidation. More specifically, the invention includes Dichlorobenzene. the production of quinones and polycarboxylic acids from Monochlorobenzene. the starting materials. Other solvents, which show some reaction with NO, Heretofore, the quinone of acenaphthene was made by but are still usable, are as follows: the reaction of acenapthene with alkyl nitrites or nitrosyl Nitrobenzene. chloride to form the oxime, which was then hydrolyzed Diphenyl ether. to form the quinone. This process required a number of Chlorinated diphenyls. steps, the use of expensive reagents, and the efficiency While the above inert solvents have been found suit of the conversion was relatively low. able, and are the best so far found, other solvents may In another prior art process, the acenapthenene was also be used. treated with sodium bichromate in acetic acid to form When oxidizing 3,4-acenaphthenedicarboxylic acid for the quinone. But it suffered from the disadvantages that instance, a charge of this substance amounting to 5% to the medium was corrosive, the reagents were expensive, 10% by weight of an inert solvent such as trichloro the yield was low and side reaction products were formed. benzene may be added to the solvent and heated to 190° In a modification of this process, the reactants in water C. before introduction of the NO. With provision for solution were heated in an autoclave under substantial 40 fine dispersion of the NO2 as it is introduced and with pressure; this had the additional disadvantage that ex Sufficient time of contact of the gas with the liquid, re pensive equipment was necessary and working under action of the NO to NO is virtually complete by the pressure has an element of danger. Another difficulty time the gas leaves the reactor until nearly all of the with oxidation reactions involving complex organic mole 3,4-acenaphthene dicarboxylic acid is oxidized to the cules is that readily condensible intermediate products quinone. The exit gases from the reactor contain vir are frequently formed in the first stages and undesirable tually no NO, or free O2. This allows the HO arising condensation products are produced, which not only in from the oxidation of the acenaphthene derivative to be terfere with the desired reaction but also waste valuable removed by condensation or condensation followed by materials and make purification of the desired product drying with silica gel without loss of NO or NO. more difficult. After drying of this gas stream, air or O is intro The present invention is intended and adapted to over duced and mixed with it and the water-free NO-O mix come the difficulties and disadvantages inherent in prior ture passed into a silica gel bed which catalyses the oxi processes for producing oxidation products of acenaph dation of NO to NO, and adsorbs the NO. The NO is thenes, it being among the objects thereof to devise a then recovered from this silica gel bed by heating the process for the above purpose which is simple and highly 5 5 bed, driving off the NO2 as a gas for recycle to the oxi effective. dation process. This means that essentially, atmospheric It is also among the objects of the invention to treat oxygen is used as the oxidant and that NO simply serves acenaphthenes so as to produce both quinones and poly as a carrier of oxygen. carboxylic acids in relative purity and with higher yields. When oxidizing acenaphthene to the quinone by NO, In practicing the invention, there are utilized acenaph 60 thene and its derivatives, such as 3,4-acenaphthene it is desired to keep the acenaphthene concentration in the dicarboxylic acid. There may be present other sub Solvent low by adding the acenaphthene continuously at stituents on the ring provided that they remain inert and a rate proportioned to the NO addition close to the do not enter into or interfere with the desired reactions. theoretical proportion of one of acenaphthene to 4NO Applicants have discovered that it is possible to oxidize 65 by weight. By proper selection of these rates according the methylene (-CH-) groups by means of nitrogen to the equipment used, it is here also possible to keep dioxide (NO) to convert them essentially to CO groups. the quantity of NO in the exit gases very low in relation To accomplish this starting material in solution in suit to the NO in these gases. This allows the NO to be re able solvents is heated to a sufficiently elevated tempera oxidized to NO, and this NO to be recovered and re ture above that at which N2O4 is largely dissociated, 70 cycled as described above. and passing NO through the solution, preferably with Acenaphthene quinone and acenaphthene quinone di stirring. The NO2 is reduced to NO and the acenaphthene carboxylic acid or the imide of this dicarboxylic acid are 3,405,171 3 4. important intermediates for the production of 1,8-naph way as described above. This procedure was repeated five thalene dicarboxylic acid (naphthalic acid) and 1,4,5,8- more times with all the results Summarized as follows: naphthalene tetracarboxylic acid, used in making dyestuffs and pigments. Amount recrystalized Run No. Weight of Crude from 30 g. Sample of The quinones so formed are then converted into the 5 Product in grams crude product in nitro corresponding carboxylic acids or their anhydrides. It has benzene, weightingrams been found by applicants that this may be accomplished 19. 26 by suspending the quinone in a relatively weak caustic 210 25.5 222 23 soda solution containing slightly in excess of two mols of 219 2. 203 21.5 caustic per mol of acenaphthene quinone and then oxi 222 17 dized with NaOCl in solution in amount slightly in ex 226 20 cess of one mol per mole of acenaphthenequinone. The same operation may be carried out on acenaphthene qui 339 g. taken from a composite of Runs 4, 5 and 6 Were none dicarboxylic acid and 1,4,5,8-naphthalene tetracar dissolved in 1130 cc of. hot nitrobenzene and recrystallized boxylic acid produced therefrom. 5 by cooling. The solids were separated by filtration, washed The following are specific examples which will illustrate with 500 cc. of methanol to remove the nitrobenzene, dried the invention without limiting the scope thereof. and weighed. 272 g of recrystallized quinone were re covered. Example 1 Example 3 1400 cc. of trichlorobenzene were placed in a 3 liter 20 A sample of the above 272 g of acenaphthene quinone resin flask provided with a center downdraft high speed was oxidized to naphthalic acid as follows: propeller agitator near the bottom and with four vertical 60 g. of quinone was mixed with 30 g. of NaOH and baffles around the periphery at the bottom and with a gas 560 cc. of 5.25% NaOCl solution and heated to a boil inlet tube leading down to a point just above the propeller. slowly, and diluted to 3000 cc. giving a pale yellow solu Two hundred grams of acenaphthene were dissolved in 25 tion. NaSOs was added until a starch-iodide paper test 600 cc. of trichlorobenzene making approximately 780 cc. showed no excess NaOCl. The solution was acidified with of solution. Sixty cc. of this solution were added to the HCl, filtered, and the solids washed and dried overnight resin flask and heated to 190° C. under agitation. NO2 at 115° C. 61 g. of dried white solids were recovered, was introduced through the gas inlet tube at a rate of having a neutralization equivalent of 99.3 or that of naph about 1.5 g./min.
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