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AssigneeDeutsche Gold- und Silber-Scheideanstalt vormals Roessler
InventorsHeinz Haschke, Gerd Schreyer, Werner Schwarze, Helmut Suchsland
Estimating the term…
There is provided a process, preferably continuous and in a given case successive, substitution of one or two chlorine atoms of cyanuric chloride by one or two amines, which may be the same or different, in the presence of an acid acceptor and in the presence of an organic solvent, particularly for the production of 2-alkylamino-4,6-dichloro and preferably for the production of 2,4-di(alkylamino)-6-chloro-s-triazines wherein there is added 1.00 to 1.05 mole, preferably 1.00 to 1.03 mole of a first amine to a 4.5 to 50 weight % suspension or solution of cyanuric chloride in a mixture of 65 to 85 weight % of xylene, toluene, ethylbenzene, benzene and/or an aliphatic or cycloaliphatic hydrocarbon with 5 to 10 carbon atoms (toluene being preferred) and 35 to 15 weight % of a ketone with 3 to 8 carbon atoms, preferably acetone, while maintaining the temperature between about 0 and about 20.degree. C, preferably about 10 to 18.degree. C., continuously so regulating the pH value of the reaction mixture obtained in accordance with the reaction time by addition of alkali and in a given case, water so that this corresponds to a point within the area bounded by lines ABCD of FIG. 1, which runs through the area beginning with the reaction time t,(step 1)= 0 until reaching a position in the area bounded by the lines BCEF and after reaching a pH of 7.0, preferably 7.2 maintains a temperature of about 10.degree. to about 60.degree. C., preferably about 25.degree. to 40.degree. C., after addition of 0.96 to 1.05, preferably 0.98 to 1.02 equivalents of alkali per mole of cyanuric chloride, adding at least an equimolar amount, preferably 1.00 to 1.02 mole of the second amine per mole of cyanuric chloride and continuously so adjusting the pH value of the reaction mixture obtained depending on the reaction time by addition of alkali that this corresponds to a point within the area which is defined by lines GHIJ in FIG. 3 which passes through the band beginning with the reaction time t(step 2)= 0 of the second reaction step until reaching a position in the area bounded by the lines HIKL and thereby maintaining a temperature of 40 to 70.degree. C., preferably 45.degree. to 55.degree. C. and thereafter working up the product in known manner wherein t.sub.1 is a time of 4 to 10 hours, preferably about 7 hours and t.sub.2 is a time of 2 to 8 hours, preferably about 6 hours and wherein the B C corresponds to the equation, pH = -(12.6/t.sub.1)+ 14.35 and the line H I corresponds to the equation pH = -(24,857/t.sub.2)+ 23.9285. There are also disclosed novel, purified mono and bis alkylamino-cyanoalkylalkylamino -- s -- triazines.
A process for the successive substitution of two chlorine atoms of cyanuric chloride comprising reacting the cyanuric chloride with two amines in the presence of an acid acceptor and an organic solvent to produce a triazine of the formula ##STR6## where R.sub.1 and R.sub.2 are lower alkyl, lower alkenyl, cyclo lower alkyl or methylcyclopropyl or such groups substituted by --0H, --OR.sub.5 --SR.sub.5 or CN where R.sub.5 is lower alkyl, with the proviso that one of R.sub.1 and R.sub.2 can be hydrogen, and R.sub.3 is as defined for R.sub.1 or ##STR7## and R.sub.4 is ##STR8## wherein R.sub.6 and R.sub.7 are alkyl or alkenyl of 1 to 8 carbon atoms, or together with the adjoining carbon atom form a 5 to 7 membered cycloalkyl ring or are cycloalkyl with the proviso that one of R.sub.6 and R.sub.7 can be hydrogen, said process comprising adding 1.00 to 1.05 mole of a first amine of the formula ##STR9## to a 4.5 to 50 weight % suspension or solution of cyanuric chloride in a mixture of 65 to 85 weight % of a hydrocarbon selected from the group consisting of benzene, toluene, xylene, ethylbenzene, aliphatic hydrocarbons having 5 to 10 carbon atoms, cycloaliphatic hydrocarbons having 5 to 10 carbon atoms and mixtures of such hydrocarbons and 35 to 15 weight % of a ketone having 3 to 8 carbon atoms, maintaining the temperature between about 0.degree. and about 20.degree. C., continuously regulating the pH value of the reaction mixture obtained in accordance with the reaction time by adding alkali that the relationship of pH to reaction time is in the area bonded by ABCD of FIG. 1 of the drawings beginning with the (reaction)time t(step 1) = 0 and containing until a position is reached in the area bounded by BCEF and after reaching a pH of 7.0 maintaining the temperature at about 10.degree. to about 60.degree. C. and after attaining said pH of 7.0 and after there has been added 0.96 ro 1.05 equivalents of alkali per mole of cyanuric chloride adding an at least equimolar amount of a different amine of the formula ##STR10## per mole of cyanuric chloride and continuously adjusting the pH value of the reaction mixture according to the reaction time by addition of alkali that the relationship of pH to reaction time is in the area bounded by GHIJ of FIG. 3 beginning with the (reaction)time t(step 2) = 0 until a position is reached in the area bounded by HIKL while maintaining a temperature of 40.degree. to 70.degree. C. and thereafter recovering the triazine product formed, and wherein t.sub.1 is 4 to 10 hours and t.sub.2 is 2 to 8 hours and further wherein the line BC corresponds to the equation pH = -(12.6/t.sub.1) + 14.35 and the line HI corresponds the the equation pH = -(24.857/t.sub.2) + 23.9285.
Dependencies are inferred from the claim text.