US3681337A
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SUPPRESSION OF TRIS(ALKYLAMINO)-s-TRIAZINE FORMATION IN THE PRODUCTION OF CHLORO-BIS (ALKYLAMINO)-s-TRIAZINES THROUGH THE USE OF ADDITIONAL CYANURIC CHLORIDE
Abstract The known commercial method of producing herbicidal chlorobis(alkylamino)-s-triazines involves the use of cyanuric chloride as a starting material and the step-wise replacement of two chlorine atoms therefrom with alkylamino groups. One of the byproducts obtained is a tris(alkylamino)-s-triazine, which is formed by replacement of the third chlorine atom in cyanuric chloride. A method for suppressing the formation of tris(alkylamino)-s-triazines comprises the steps of (1) adding additional cyanuric chloride to the reaction mixture immediately after the chloro-bis(alkylamino)-s-triazine reaction is complete, thus forming a dichloro-alkylamino-s-triazine, (2) hydrolyzing the dichloro-alkylamino-s-triazine and the unreacted cyanuric chloride, and (3) removing of the hydrolyzed by-products by filtration.
The method of claim 1 in which the cyanuric chloride is added in a molar excess of from about 50 to 100 percent relative to the excess of alkylamine present.
Claim 2
Dependent Claim
130 words
In a process for preparing 2-chloro-4-ethylamino-6-isopropylamino-s-triazine in a medium having a pH of from about 11.0 to 12.5 by means of the step-wise replacement of two chlorine atoms of cyanuric chloride with an isopropylamino group and an ethylamino group and in which the ethylamine is present in a molar excess of from about 1 to about 5 percent, the method of suppressing the formation of 2,4-bis (ethylamino)-6-isopropylamino-s-triazine which comprises adding to the reaction mixture, after the second chlorine atom has been replaced with an ethylamino group, (1) cyanuric chloride in an amount sufficient to react with the excess ethylamine in order to form 2,4-dichloro-6-(ethylamino)-s-triazine and (2) sufficient alkali metal hydroxide in order to maintain the pH in a range of between about 11.5 and 12.5 and to hydrolyze the 2,4-dichloro-6-(ethylamino)-s-triazine.
Claim 3
Dependent Claim
28 words
The method of claim 3 in whiCh the cyanuric chloride is added in a molar excess of from 50 to 100 percent relative to the excess ethylamine present.
Claim 4
Dependent Claim
14 words
The method of claim 3 in which the alkali metal hydroxide is sodium hydroxide.
Claim 5
Dependent Claim
43 words
The method of claim 5 in which the reaction mixture is allowed to remain for a period of 3 hours at a temperature of 50* after the addition of the cyanuric chloride and sodium hydroxide in order to ensure that hydrolysis is complete.
Claim 6
Dependent Claim
45 words
The method of claim 5 in which the reaction mixture is allowed to remain at a temperature of 70* C for a period of one hour after the addition of the cyanuric chloride and sodium hydroxide in order to ensure that the hydrolysis is complete.