DE1964619B2 - ADIABATIC PROCESS FOR THE PREPARATION OF N-MONOSUBSTITUTED 2,4DICHLORO-6-AMINO-S-TRIAZINES - Google Patents

Description

The inventive method avoids these disadvantages by performing the adiabatic Process. This means that the required reaction

The present invention relates to a time that has not yet been drastically reduced. The desired end products, which are customary and extremely fast, are obtained after reaction times of 1 to 2 minutes for the preparation of N-monosubstituted compounds. As a result, the space-time yield of 2,4-dichloro-6-amino-s-triazines, in which the amino of the process according to the invention compared to the group by a lower alkyl or alkenyl known process, increases sharply, which in turn results in a cycloalkyl radical With up to 6 carbon atoms, the reactors used are substituted for the same atoms, are of very high purity and production levels are kept relatively small, and very high yields can be achieved by converting cyanurides. In addition, the chloride used can be constructed very simply with a corresponding primary amine apparatus, since there is no need for any cooling equipment in the presence of an acid-binding agent. Another advantage of the two-phase organic-aqueous medium, the process according to the invention, is that it is characterized in that the reaction can be carried out continuously, particularly well, under adiabatic conditions. In view of the fact that both the off-characteristic examples of alkyl groups are starting material as well as the end products hydrolyzing the following: propyl, isopropyl, butyl, isobutyl, bare chlorine atoms, it must be surprisingly amyl or hexyl; as alkenyl groups are to be mentioned 55 that with the value according to the invention propenyl or butenyl; as a representative of cyclo method, the desired end products with ausalkylgruppen may be mentioned cyclopropyl, cyclobutyl and drawn purity of about 99 ° / ₀ and having a cyclohexyl. Yield up to 99.6% of theoretical obtained by the present process are intermediates manufacturer since 60 to doors of 8O ⁰ C with the aqueous alkaline represents both the starting and final products in Temperastellbaren compounds suitable for the production of di- come into contact with the amino-chlorine reaction medium,
S-triazines are used, which in turn are used to prevent unei> ■ "ischtem vegetation and the cyanuric chloride in an inert organic unwanted vegetation and therefore added by solvents. Suitable solvents for extremely great value and of great More economical 65 for this purpose are: toluene, benzene, cylol, acetone or importance as herbicides. Particularly valuable methyl ethyl ketone.

Diamino compounds of the trade, which are used as herbicides As acid-binding agents, which are used in the present

are used are e.g. B. 2-chloro-4-ethylamino process can be used, must be

3 4

imagine: the amine to be converted, alkali metal. .
hydroxides or alkali metal carbonates, for example Example 1
Sodium hydroxide, sodium carbonate, potassium hydroxide To a solution of 92.2 g (0.5 mol) of cyanuric chloride or potassium carbonate. As a rule, aqueous toluene in 500 g of toluene at 24 ° C., which is used in a four-solution of these acid-binding agents, is equipped with a round-neck flask equipped with a dropping funnel, stirrer, usually a 50% sodium hydroxide solution, a condenser and a thermometer is, of course, solutions that contain more or solution of 29.6 g (0.5 mol) of isopropylamine and 20.0 g of less than 50% of the chosen acid-binding (0.5 mol) sodium hydroxide and 500 g of water from the agent are usable. 24 ° C for 10 seconds with stirring

As a rule, stoichiometric amounts of the io are added. The temperature of the reaction mixture

Reactant used, i.e. about 1 mole increases to 80 ⁰ C in less than 30 seconds.

Amine, 1 mole of cyanuric chloride and about 1 mole of säurt- After exactly one minute, the analysis of the

binding agent. However, if the amine itself is the end product 99.8% 2,4-dichloro-6-isopropylamino-

acid-binding agent is used, natural s-triazine, 0.2% l ^ bis-isopropylamino-o-ch'.or-s-tri-

Lich at least 2 moles of this amine per mole of cyanuric 15 azine and traces of cyanuric chloride,

chloride can be used. . .

In one embodiment of the invention, Example 2

Cyanuric chloride and isopropylamine in a continuous 26.8 kg per hour (1 mole) isopropylamine, 37.2 kg

ierlich working reactor implemented. So z. B. per hour (1.02 mol) 50% sodium hydroxide

Water, a 50% sodium hydroxide solution and 20 solution and 163 kg per hour of water were made from

Isopropylamine mixed in a mixing tank and the different lines in a mixing tank and the

Mixture on it the continuously working resulting mixture was simultaneously with 558 kg

Reactor are fed. Simultaneously with the addition per hour of 15% cyanuric chloride solution in toluene

this mixture to the reactor becomes a solution of in a continuously operating reactor of one

Cyanuric chloride in toluene fed into the reactor and allowed to run in and through 25 volumes of 4.15 liters,

L'insetzung delivers in a time period of 1 to Reaction was at a temperature of 31 ⁰ C

2 minutes the desired 2,4-DiChIOr-O-ISOPrOPyI- started under adiabatic conditions. From-

amino-s-triazine. flow temperature was 80 ⁰ C. After analysis it was

Also for the production of 2,4-dichloro-6-iso- found that the conversion was 99.5% and

propylamino-s-triazine, with isopropylamine equal to 30 a yield of 98.5% ^of 99.0% pure 2,4-di-

if the acid-binding agent is early on, a chloro-6-isopropylamino-s-triazine can be achieved,

continuously operating reactor can be used. . . .

Water, isopropylamine and toluene, ö e 1 s ρ 1 e

which dissolved the cyanuric chloride to be reacted. The reactants were introduced into the reactor with a volume of 53.6 kg per hour of isopropylamine of 7.5 liters. The inflow amounts from the different (2.0 mol), 174 kg per hour of water and 558 kg per different lines are regulated so that approximately 15% cyanuric chloride solution in toluene in table stoichiometric amounts of the various one continuous reactor of one volume Reaction components come to the implementation. The 7.5 liters let in and run through. The monitoring of mutual amounts of cyanuric 40 temperatures at the inlet were 3O ⁰ C and the chloride and isopropylamine is particularly important. Outlet 80 ° C. The implementation was 99.5%

The following examples serve as an illustration of 99.0% pure 2,4-dichloro-6-isopropyl-

solution of the method according to the invention. amino-s-triazine was 99.5%.

Claims (2)

ι 2 6-isopropylamino-s-triazine or 2-chloro-4,6-bis-iso claims: propylamino-s-triazine. These diamino compounds can be used both as selective herbicides for weed control 1. Process for the production of N-mono-control in crop plants and as soil-substituted ones 2,4-dichloro-6-amino-s-triazines of the 5 sterilants for total suppression general formula of unwanted plants can be used. The 2,4-dichloro which can be prepared according to the invention Cl ^ .N, Cl amino-s-triazines are known compounds V ^ ⁷ and are usually produced by implementation ¹ 'ίο of cyanuric chloride with primary amines at lower ^N N temperatures and in the presence of a solvent. Λ / When performing this procedure, it is necessary ! agile, the hydrochloric acid formed during the implementation Neutralize NH - R. The implementation is therefore in 15 the presence of an acid-binding agent wherein R is a lower alkyl or alkenyl or led. As such, either an excess of a cycloalkyl radical with up to 6 carbon atoms to be reacted amine or, for example, sodium hydroxide means to serve by reacting cyanuric chloride or sodium carbonate. with an amine of the general formula RNH ₂ , Although this process in terms of yield and in which R has the meaning given above, 20 purity of the desired end products / ufiicdcnn in the presence of an acid-binding agent in providing results, it is associated with a two-phase organic-aqueous medium, significant disadvantages. This is characterized by the fact that the long reaction times are particularly important. Implementation under adiabatic conditions, which takes place as a result of carrying out the reaction at deeper. 25 Temperature - in practice it is at temperatures 2. The method according to claim 1, characterized in that worked between 0 and -4-5 'C - are required. draws that the amine is first mixed with the acid. Another problem is the removal of the releasing agent Means mixes and becomes a solution of standing heat of reaction. This includes cnt cyanuric chloride in an inert organic solvent so that the reaction can be carried out in the presence solvent admits. 30 of ice or one uses one with appropriate Apparatus provided with cooling devices (e.g. cooling jackets and cooling coils). It is Dabsi Because of the desired low temperatures, it is necessary to use brine cooling, which is what the - 35 the effort involved in carrying out the procedure increased even further.