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United States Patent (19) [11] 3,932,402 Norell (45) Jan

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United States Patent (19) [11] 3,932,402 Norell (45) Jan United States Patent (19) [11] 3,932,402 Norell (45) Jan. 13, 1976 54 PREPARATION OF SYM-TRAZINES BY 3,071,586 111963 Sandner et al...................... 260/248 TRIMERIZATION OF NITRLES IN 3,095,414 6/1963 Spain hour........................... 260/248 3,238,138 3/1966 Braunwarth et al... ... 260/248 X TRIFLUOROMETHANESULFONIC ACD 3,654, 192 4/1972 Vogel.................................. 260/2 R 75 Inventor: John R. Norell, Bartlesville, Okla. OTHER PUBLICATIONS 73 Assignee: Phillips Petroleum Company, Cool et al., J. Chem. Soc., 1941, pp. 278-282. Bartlesville, Okla. Elderfield, “Heterocyclic Compounds", Vol. 7, Ch. 7, pp. 642, 644 and 686. 22) Filed: June 24, 1974 Migrdichian, "The Chemistry of Organic Cyanogen 21 ) Appl. No.: 482,257 Compounds,' Ch. 17, pp. 356, 357 and 367. (52) U.S. Cl............................................ 260/248 CS Primary Examiner-John M. Ford 51) Int. Cl’........................................ C07D 251/24 58 Field of Search............................... 260/248 CS 57 ABSTRACT Aliphatic and aromatic nitriles are trimerized to sub 56) References Cited stituted symmetrical triazines in the presence of UNITED STATES PATENTS trifluoromethanesulfonic acid. 3,060, 179 lof 1962 Toland................................ 260/248 16 Claims, No Drawings 3,932,402 2 In one embodiment of this invention, the organic PREPARATION OF SYM-TRAZINES BY nitrile is an aliphatic nitrile. The product of this process TRIMERIZATION OF NITRILES IN is a 2,4,6-trialkyl-1,3,5-triazine. TRFLUOROMETHANESULFONIC ACID In another embodiment of this invention, the organic This invention relates to substituted sym-triazines. In 5 nitrile is an aromatic or substituted aromatic nitrile in one aspect it relates to the preparation of alkyl-sub which case the product of the process is a 2,4,6-triaryl stituted sym-triazines. In another aspect it relates to the 1,3,5-triazine. preparation of aromatic-substituted sym-triazines. Examples of suitable organic nitriles for use in this Compounds having the sym-triazine ring structure invention include: propionitrile, n-butyronitrile, 10 isobutyronitrile, n-nonamenitrile, pentanenitrile, ben are well known in the art as intermediates in the prepa zonitrile, o-tolumitrile, p-chlorobenzonitrile, p ration of dyes, pharmaceuticals, rodenticides and the iodobenzonitrile, phenylacetonitrile, p-methoxyben like. There are several processes reported in the prior zonitrile, m-fluorobenzonitrile, p-bromobenzonitrile, art for the preparation of alkyl- and aryl-substituted p-tolumitrile, m-tolunitrile and the like. triazines which require the use of various catalysts. 15 As noted above, the trimerization reaction is carried These include strong acid catalysts such as sulfuric out in the presence of trifluoromethanesulfonic acid. acid, chlorosulfonic acid, hydrochloric acid in alcohol, The amount of trifluoromethanesulfonic acid used can and Lewis acids, amides and hydrides of alkali metals vary within rather broad limits, ranging from 0.8 to 20 and alkaline earth metals, metal alkyls, metallic sodium moles of trifluoromethanesulfonic acid per mole of and elemental bromine. In the acid-catalyzed reactions, 20 nitrile. In a presently preferred embodiment the molar the available literature stresses that those nitriles pos ratio of trifluoromethanesulfonic acid to nitrile is in the sessing an alpha-hydrogen; i.e., aliphatic nitriles, will approximate range of 1.2 to 10. not trimerize. Aliphatic-substituted triazines have been The trimerization reaction is rapid and exothermic, prepared from aliphatic nitriles via the imidate, how therefore the admixture of nitrile and trifluorome ever, the reaction is difficult to handle and requires 25 thanesulfonic acid is prepared at relatively low temper isolation of the imidate salt. atures to avoid overheating. After admixture of the It is an object of this invention to provide an im nitrile and trifluoromethanesulfonic acid, the reaction proved process for the preparation of substituted sym mixture can be warmed or heated to cause the trimeri triazines. zation to proceed to completion The temperature of It is another object to provide an improved process 30 reaction can range from -20 to 100°C, prefer for the preparation of alkyl-substituted sym-triazines. ably from 10 to 50°C. In a presently preferred It is another object to provide an improved process embodiment, the mitrile is added to the trifluorome for the preparation of aromatic-substituted sym-tria thanesulfonic acid. zines. Reaction time will be sufficient to effect the desired Other objects, aspects, and advantages of the inven 35 conversion of nitrile to triazine compound and gener ally ranges from 0.25 to 24 hours. tion will become apparent to those skilled in the art Within the parameters given above, the reaction can upon consideration of the accompanying disclosure. be carried out batchwise or continuously, using any In accordance with the present invention there is suitable apparatus. After completion of the reaction, provided a process for the preparation of substituted 40 the trimer can be isolated and purified by any suitable triazines of the general formula means including solvent extraction, filtration, crystalli zation and distillation. The present invention provides a facile process for the preparation of alkyl- and aryl-substituted triazines. 45 Heretofore, trialkyl-substituted s-triazines were pre pared either with great difficulty or not at all using the R-C C-R processes of the prior art. M / The following examples illustrate the invention. N The exemplary runs described in the following exam 50 ples were carried out in an appropriately sized 3-neck wherein R is a radical selected from the group consist round-bottom flask equipped with a thermometer, con ing of alkyl, aryl and combinations thereof, such as denser, addition funnel, nitrogen inlet tube and mag aralkyl and alkaryl, and substituted aryl, such as halo netic stirring device. According to the presently pre aryl and alkoxyaryl, having from 2 to 9 carbon atoms ferred procedure, the trifluoromethanesulfonic acid per radical group, wherein the alkyl group contains an 55 was placed in the reaction flask and cooled to about alpha-hydrogen, i.e., a hydrogen atom on the carbon 0°C. The nitrile was added, dropwise, to the cooled atom which is bonded to the nitrile function. Substitu trifluoromethanesulfonic acid over a time period rang ents of the substituted aryl radical groups include halo ing from 30 minutes to 1 hour. After addition of the gen, alkyl and alkoxy. When present, such substituents nitrile was complete, the reaction mixture was stirred, are preferably located in the 3,4 and/or 5 positions. 60 at room temperature, for up to about 18 hours. To According to the process of the present invention, an isolate the trimer, the reaction mixture was poured organic nitrile having the general formula R-CN, over ice, then neutralized with ammonium hydroxide wherein R is selected from the group consisting of or sodium bicarbonate and the trimer isolated by filtra alkyl, aryl and substituted aryl having from 2 to 9 car tion or by extraction with ether or methylene chloride. bon atoms per radical group, wherein the alkyl group 65 The trimer was purified by recrystallization or distilla contains an alpha-hydrogen, is reacted under reaction tion. conditions in the presence of trifluoromethanesulfonic Alternatively, most of the trifluoromethanesulfonic acid to form a symmetrical triazine. acid was removed from the reaction mixture by vac 3,932,402 3 4 uum distillation prior to pouring the reaction mixture After drying the ethereal extract, concentration pro over ice. (See Example X.) vided 9.5 g of impure product. Recrystallization of the crude product from n-hexane provided 3.1 g of white EXAMPLE I crystals (m.p. 95-115°C) and evaporation of the Benzonitrile (5.2 g, 0.05 mol) was added dropwise 5 filtrate gave an additional 4.5 g which was recrystal over a period of 100 sec to 20 ml (34 g, 0.23 mol) of lized to give 0.40 gpf 2,4,5-tri-o-tolyl-s-triazine (white stirred trifluoromethanesulfonic acid with the tempera crystals, m.p. 112-114C) (Lit. m.p. 110° C., J. ture being allowed to rise as high as 91C. When the Chem. Soc., 1941, 278). The characteristic triazine reaction mixture cooled to 25°C, the yellow solu band at 6.5 pu was observed in the infrared spectrum tion was poured into 100 ml cold ethanol. The yellow 10 of the product. color disappeared and a white flocculent precipitate formed. Recrystallization of this precipitate from 150 ml chloroform afforded 3.43 g (66 percent yield) of Anal. Calcd. for CHN: C 82.02; H,6.02; N, 11.95. 2,4,6-triphenyl-s-triazine (white crystals, m.p. Found: C,81.96;81 H,5.95; N, 11.82. 235-237°C) (Lit. m.p. 232°C, J. Chem. Soc., 15 1941, 278). The 3.43 g sample of product exhibited no nitrile bands in the infrared spectrum but the infrared EXAMPLE V spectral band characteristic of the triazine structure p-Chlorobenzonitrile (6.8 g., 0.05 mol) was added in was very strong at 6.6 pu. small portions to 25 ml (42.5 0.29 mol) trifluorome 20 thanesulfonic acid at 0-10C. The mixture became EXAMPLE II dark orange but was homogeneous; on removal of the p-Tolunitrile (11.7 g, 0.10 mol) was added in small ice bath, the mixture warmed to 30°–40°C. After portions to 25 ml (42.5 g 0.29 mol) of trifluorome stirring overnight, the mixture was poured on ice and a thanesulfonic acid at 25-30 C. After stirring over white flocculent precipitate formed. After neutraliza night, the dark brown reaction mixture was poured on 25 tion with ammonium hydroxide, the precipitate ice and neutralized with ammonium hydroxide. The formed. After neutralization with ammonium hydrox insoluble precipitate was filtered off and washed with ide, the precipitate was isolated by filtration and dried acetone to give 9.7 g of white solid.
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