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UNITED STATES PATENT OFFICE 2,262,262 PROCESS of MAKING MALEANILS John H

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UNITED STATES PATENT OFFICE 2,262,262 PROCESS of MAKING MALEANILS John H Patented Nov. 11, 1,941‘ 2,262,262 UNITED STATES PATENT OFFICE 2,262,262 PROCESS OF MAKING MALEANILS John H. Speer, Niles Center, 111., assignor to Na tional Aniline and Chemical Company, Inc., New York, N. Y., a corporation of New York No Drawing. Application August 19, 1939, Serial No. 291,003 8 Claims. (Cl. 260-—313) This invention relates to a process of making mides is preferred. Thionyl chloride, a preferred maleanils, that is, the class of compounds rep treatment agent, has a boiling point of 78° C. resented by the general formula: Preferably the maleanilic acid to be treated is suspended in a suitable liquid medium, which is inert to the reacting materials, and while the mixture is maintained at a temperature between 160° and 200° C., the selected acidyl chloride or in which R is a substituted or unsubstituted aryl bromide treatment agent is gradually introduced radical, from the corresponding maleanilic acids, until the reaction is complete, which will be in represented by the general formula: 10 dicated when the formation of hydrogen chloride or bromide gas ceases. The treatment agent may be added directly to the mixture, or may be volatilized and mixed with a stream of dry air It is known that maleanilic acids react with or other suitable gas and the resulting stream acidyl chlorides to form chlorsuccinanils and to 15 of gas and vapor may be passed into the mixture form isomers of the maleanils. The latter may of maleanilic acid and liquid medium. be represented by the formula: I prefer to use an inert solvent which with the maleanilic acid forms a mixture boiling between 160° and 200° C., and to maintain the reaction 20 mixture automatically at a temperature within cH-ooll 2) this range by maintaining the mixture in a boil ing state. By conducting the reaction in a vessel See, for instance, Gazetta Chimica Italiana 28, provided with a re?ux condenser, loss of solvent II, pp. 189-192; Annalen der Chemie, 309, p. 347; is prevented and the hydrogen chloride or hydro and Atti della Reale Accademia dei Lincei, (5), 25 gen bromide which is evolved is expelled from 18, II, pp. 312-326. For this reason treatment of the chamber through the condenser. Commer maleanilic acids with acidyl chlorides (or with cial dichlorbenzene has been found to be very acidyl bromides) has not been applied to the preparation of maleanils. satisfactory for use as a solvent, and I prefer to use ortho-dichlorbenzene, which has a boiling or According to my invention a maleanilic acid 30 re?uxing temperature of about 180° C. Other corresponding to the desired maleanil is con examples of inert solvents having suitable re?ux verted into the latter by treatment with an or boiling temperatures are tetralin, kerosene, and ganic or inorganic acidyl chloride or acidyl bro commercial cymene. Although the character of mide at a temperature between about 160° ‘and the particular maleanilic acid being reacted and about 200° C. ‘its reaction product may alter the boiling tem I have discovered that at temperatures between perature of a solution, it is possible even in ex about 160° and about ‘200° C. maleanils are ob treme cases, by providing suf?cient solvent, to tained in substantial yields from the treatment adjust the boiling temperature of the solution of maleanilic acids with acidyl chlorides or bro to approximately that of the solvent. At the end mides, and without any accompanying substan of the reaction, continued boiling of the solvent tial production of chlorsuccinanils or bromsuc mixture under re?ux will serve to drive off the cinanils, or isomers of maleanils. At such tem remaining hydrogen chloride or hydrogen bro peratures the addition of hydrogen chloride and mide and other volatile undesired substances hydrogen bromide to the maleanil product is present, following which the solvent may be apparently inhibited and the hydrogen chloride removed by distillation under atmospheric pres or bromide formed as a reaction vproduct is sure, or in any other suitable manner. largely driven off from the reaction mixture as My invention also contemplates conducting formed. the reaction in liquid media which boil sub Examples of acidyl chlorides and acidyl bro stantially above 200° 0., for example, solutions mides are: thionyl chloride (S0012), phosphorus employing, as solvent, naphthalene or molten trichloride (P013), acetyl chloride (CI-130001), paraffin. Such solutions must be maintained at thionyl bromide, phosphorus tribromide, and a temperature below the normal boiling point in acetyl bromide. The substances listed are all order to provide a suitable reaction temperature. readily volatile, boiling below 200° C., and the By conducting the reaction under pressure su?i use of such volatile acidyl chlorides and bro cient to raise the boiling point to the desired re 2 2,262,262 action temperature, media having boiling points through the refluxing mixture of solvent and below the desired reaction temperature may be maleanilic acid. The latter gradually dissolved. used. 125 parts of the thionyl chloride were vaporized Upon completion of the reaction, the residual and introduced into the re?uxing mixture in hydrogen chloride or hydrogen bromide is driven this manner, reacting with the maleanilic acid off by continued heating, together with any ex to form maleanil, sulfur dioxide, and hydrogen cess acidyl chloride or acidyl bromide if a readily chloride, the latter two reaction products large volatile form has been used. When thionyl chlo ly passing off through the re?ux condenser. In ride or bromide is used, sulfur dioxide will be order to remove residual sulfur dioxide and hy formed as one reaction product thereof and is 10 drogen chloride from the mixture, re?uxing was readily driven off along with the hydrogen chlo continued for about one hour after the last of ride or bromide during the course of the reaction the thionyl chloride had been passed into the and during the subsequently continued heating, _ mixture. so that no reaction products from the acidyl The bulk 'of the dichlorbenzene solvent was chloride or bromide will remain. When phos 15 then removed by distillation at atmospheric phorus trichloride or tribromide is used, a re pressure, and the resultant residual mixture was sidual amount of phosphorus-containing mate-Z ‘distilled in vacuo. Fractional distillation at 5 rial will remain and can be removed by cooling . mm. (mercury) pressure was employed for sepa the mixture and washing with a weakly alkaline . ration of the maleanil, the fraction distilling o? solution (such as an aqueous 5% to 10% sodium 20 between 140° and 155° C‘. being collected sepa-‘ carbonate solution) and then with water. rately as crude maleanil. The yield was 82 parts. The resultant solvent mixture may be freed of The crude product was a bright yellow crystal solvent by distilling off the latter at atmospheric line solid having a freezing point of 85° C. It was pressure or lower. When a solvent having a boil dissolved in and crystallized from alcohol, yield ing puri?ed maleanil which was found to have a ing point substantially in excess of 200° C. has 25 been used, care should be taken not to allow melting point of 895° C. the temperature of the mixture to greatly ex Example 2.-—-60 parts of the mono-metachlor ceed 200° C‘. for an appreciable time, as other anilide of maleic acid, having the formula: wise substantial decomposition of the maleanil will occur. 30 The distillation residue contains the maleanil product and the latter is separated out in any were suspended in 330 parts of commercial ortho dichlorbenzene, the mixture was heated to its convenient manner. For example, the residue refluxing temperature of about 180° C, and a may be subjected to fractional distillation under stream of dry air carrying the vapors from 33 vacuum (such as 4 mm. to 5 mm. mercury abso 35 lute pressure) and the fraction containing the parts of thionyl chloride was passed through the bulk of the maleanil may be isolated as the crude mixture, in the manner described in Example 1. maleanil product. The latter may be puri?ed by -After removal of the solvent dichlorbenzene by crystallization from alcohol to yield a substan distillation at atmospheric pressure, the residue was distilled in vacuo and the fraction which dis tially pure maleanil. 40 The following examples illustrate the prepa tilled between about 170° and about 183° C. at ration of typical maleanils from corresponding 5 mm. pressure was collected separately as the desired product. This product, which was sub maleanilic acids in accordance with my inven stantially 3’-chlor-l~maleanil, having the for tion. In these examples, “parts” means parts mula: by weight. ‘ Example 1.—This example illustrates the prep aration of maleanil using maleic anhydride and aniline as the raw materials to form maleanilic acid, which is then converted into maleanil by interaction with thionyl chloride, both reactions was very soluble in hot, sparingly soluble in cold, being conducted in dichlorbenzene which does alcohol. It was crystallized from an alcoholic not enter into the reactions. The reactions in solution as pale yellow prisms having a melting volved in this combined process may be repre point of 93° C. sented as follows: Example 3.—Using the same procedure as in 55 the preceding example, the mono-2',3'-methyl chloranilide of maleic acid was suspended in boiling commercial dichlorbenzene and was con verted by means of thionyl chloride to the cor responding 2'-methyl-3'-chlor-l-maleanil: 60 (Maleanil) CH—CO/11211430 | In a suitable apparatus‘ ?tted with an agita CH: 01 tor and a re?ux condenser, 98 parts of maleic 65 which was separated from the residue, after re anhydride were dissolved in 665 parts of com moval of the solvent, by distillation in vacuo.
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