JPH0616614A - Nitrile manufacturing method - Google Patents

Abstract

(57) [Summary] [Objective] A novel method for producing 5-chloro-2,4,6-trifluoroisophthalonitrile which is useful as an intermediate for agricultural chemicals, pharmaceuticals, and other industrial products. [Structure] 5-chloro- by reacting tetrachloroisophthalonitrile with potassium fluoride in the absence of a solvent
A method for producing 2,4,6-trifluoroisophthalonitrile.

Description

Detailed Description of the Invention

[0001]

The present invention relates to 5-chloro-2,4,6 which is extremely useful as an intermediate for pharmaceuticals, agricultural chemicals, industrial chemicals and the like.
-A process for the production of trifluoroisophthalonitrile.

[0002]

2. Description of the Related Art Conventionally, for example, the following method is known as a method for producing 5-chloro-2,4,6-trifluoroisophthalonitrile.

(1) Diamond Alkali C
o. Fr. According to 1,397,521, DMF is used as a solvent and tetrachloroisophthalonitrile and KF are used.
5-chloro-2,4, by reacting at 30 to 145 ° C. for 3 hours
6-trifluoroisophthalonitrile has been obtained.

(2) In addition, the Chemical Society of Japan 1985, (1
1), p. In 2155 to 2160, DMF / cd. KF
84% yield has been obtained by using

These use DMF, and there is no description of a method for synthesizing 5-chloro-2,4,6-trifluoroisophthalonitrile in the absence of a solvent. However, as a reaction example using no solvent, G.I. G. Yakobson, V .;
E. Platonor, N.M. N. Vorazhtso
v, Jr. , Zh. Obshoh. Khim, 35, 1
158 (1965) synthesizes, for example, hexafluorobenzene, but the reaction conditions are strict and the yield is low, which does not teach the present invention at all.

Therefore, the method using the above-mentioned solvent involves various problems and is not suitable as an industrial production method. That is, the above-mentioned method is industrially difficult because the yield is low, the amount of by-products is large, and the solvent is difficult to recover.

[0007]

As described above, the conventional manufacturing method is not always suitable as an industrial manufacturing method.

The present invention is surprisingly found in 5-chloro-2,
It is possible to obtain 4,6-trifluoroisophthalonitrile and potassium fluoride in a high yield in a solventless reaction under atmospheric pressure without using an autoclave, and to provide a novel and industrially advantageous production method. is there.

[0009]

[Means for Solving the Problems] The starting material of this production method is tetrachloroisophthalonitrile, which is a widely used agricultural and horticultural germicide Daconyl (registered trademark of SDS Biotech Co., Ltd.). It is industrially manufactured as a drug substance.

The tetrachloroisophthalonitrile and potassium fluoride, preferably spray-dried potassium fluoride, are used in a molar ratio of 1: 3 to 1: 100, preferably 1: 3.
Mix 1: 1-1: 8 and react without solvent. The pressure may be normal pressure, and the reaction temperature is 140 to 260 ° C., preferably 15
The reaction time is 2 to 20 hours, preferably 3 to 10 hours.

The treatment after the reaction may be carried out by appropriately selecting an ordinary method. For example, after cooling, it is extracted with a suitable organic solvent such as toluene, the inorganic matter is filtered off, and the solvent is distilled off under reduced pressure to produce the desired 5-chloro-2,4,6-trifluoroisophthalonitrile. be able to.

[0012]

【Example】

Example-1 (Production of 5-chloro-2,4,6-trifluoroisophthalonitrile) Tetrachloroisophthalonitrile 26.
6 g (0.1 mol) and 23 g of spray-dried KF (0.
4 mol) is mixed well and heated on an oil bath maintained at 210 ° C. for 7 hours with slow stirring.

After completion of the reaction, the mixture was cooled to 80 ° C. and toluene 12 was added.
Add 0 ml and reflux for 1 hour for extraction. After cooling, suction filtration was carried out, toluene was distilled off under reduced pressure, and the remaining solid was vacuum dried to obtain 39.8 g of the desired product (yield 92%).

Example 2 26.6 g (0.1 mol) of tetrachloroisophthalonitrile and 34.8 g (0.6 mol) of spray-dried KF were mixed well and charged into a 200 ml three-necked flask.
The mixture was heated and stirred for 8 hours while maintaining the temperature at ℃. Thereafter, the mixture was cooled to 80 ° C., 100 ml of toluene was added, the mixture was refluxed for 1.5 hours, cooled to room temperature, filtered, and toluene was distilled off from the mother liquor under reduced pressure. Was obtained (yield 76.7%).

Example 3 Tetrachloroisophthalonitrile (26.6 g, 0.1 mol) and spray-dried KF (23.2 g, 0.4 mol) were mixed well and charged into a 200 ml three-necked flask.
The mixture was heated and stirred for 4 hours while maintaining at ℃. Thereafter, the mixture was cooled to 80 ° C., 100 ml of toluene was added, the mixture was refluxed for 1.5 hours, cooled to room temperature, filtered, and toluene was distilled off from the mother liquor under reduced pressure. Was obtained (yield 86.8%).

Claims (3)

[Claims] 1. A process for producing 5-chloro-2,4,6-trifluoroisophthalonitrile by reacting tetrachloroisophthalonitrile with potassium fluoride in the absence of a solvent. 2. The method according to claim 1, wherein the potassium fluoride is spray-dried potassium fluoride. 3. The reaction temperature according to claims 1 and 2 is 15
A production method in which the temperature is 0 ° C. or higher and 250 ° C. or lower.