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Process for preparation of 2,6-dichlorobenzonitrile

A technology of dichlorobenzonitrile and chlorobenzonitrile, which is applied in the field of preparation of 2,6-dichlorobenzonitrile, and can solve problems such as unfavorable industries, limited sources of 2,6-dichlorotoluene, and large investment in equipment

Active Publication Date: 2021-06-25
ARYSTA LIFESCIENCE CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Known industrial methods for the production of such materials involve, for example, gas-phase catalytic ammoxidation of 2,6-dichlorotoluene, requiring significant investment in equipment and limited availability of the expensive raw material 2,6-dichlorotoluene
[0005] US4225534A discloses the preparation of 2 - Chlorobenzonitrile derivatives, making it industrially unfavorable

Method used

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  • Process for preparation of 2,6-dichlorobenzonitrile
  • Process for preparation of 2,6-dichlorobenzonitrile
  • Process for preparation of 2,6-dichlorobenzonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] This method is the following example, which demonstrates the effect of temperature on the reaction.

[0085] Table 2

[0086]

[0087] In the above examples, nitrosylsulfuric acid was produced and isolated in solid form from the sulfuric acid scrubber in molar equivalents to released NOx.

Embodiment 2

[0089] With overhead stirrer, TP, powerful column with concentrated H in oil bath 2 SO 4 In the 1 liter 4 neck RBF of the scrubber, charge 2-chloro-6-nitrobenzonitrile and increase the temperature. Chlorine gas was then slowly purged into the flask to obtain a consistent rate.

[0090] The 2,6-CNBN conversion rate of the obtained reaction material was analyzed to be ≥99%; 2,6-dichlorobenzonitrile was observed to be 73-80%; TCB was observed to be 9.4-10%.

[0091] After the reaction was completed, the reaction mass was cooled to 100° C. and diluted with monochlorobenzene, neutralized by washing with 10% aqueous sodium carbonate solution, and decolorized with activated carbon. The decolorized 2,6-dichlorobenzonitrile solution was refluxed in methanol and crystallized at 10 °C, filtered and dried in a vacuum oven.

[0092] table 3

[0093]

[0094] These examples demonstrate that DCBN can be denitrochlorinated by CNBN at 180-190°C in 71-76% yield and >98% by utilizing co...

Embodiment 3-6

[0096] 2-Chloro-6-nitrobenzonitrile (obtained from the method described in Example 7) was charged to an RBF equipped with concentrated sulfuric acid and caustic scrubber, overhead stirrer and electrically heated oil bath, and The temperature rose to 195°C. Chlorine is then purged at varying rates for 10-16 hours in a controlled sequence. The resulting reaction mass was analyzed for 2,6-CNBN conversion to >99%, and 2,6-dichlorobenzonitrile was shown to be 92-94%. Dilute the reaction mass with monochlorobenzene at 100°C; neutralize by washing with 10% aqueous sodium carbonate; decolorize with activated carbon.

[0097] The decolorized 2,6-dichlorobenzonitrile solution was refluxed in methanol and crystallized at 10 °C, filtered and dried in a vacuum oven.

[0098] Table 4

[0099]

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PUM

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Abstract

Disclosed herein a process preparation of 2,6-dichlorobenzonitrile. A process of making high yield, high purity 2,6-dichlorobenzonitrile including the selective de-nitrochlorination of 2-chloro-6-nitrobenzonitrile by treatment of the 2-chloro-6-nitrobenzonitrile with chlorine gas.

Description

technical field [0001] The technical field to which this invention generally relates is processes for the preparation of chemical substances useful in pesticidal and herbicidal compositions. More specifically, the present invention relates to processes for the preparation of halobenzonitriles. Background technique [0002] While many chemicals are known to be very effective raw materials for herbicidal and insecticidal applications, many require substantial investment in special equipment and / or expensive raw materials to produce them. Since this can add significant cost to the commercialization of these products, there is a constant search for ways to produce such products in a more effective and efficient manner. [0003] 2,6-Dichlorobenzonitrile, also known as dichlorobenzonitrile, is a widely used herbicide in agriculture. [0004] Various methods are known for the synthesis of 2,6-dichlorobenzonitrile by ammoxidation. Known industrial methods for the production of su...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N37/34A01P13/00C07C255/49
CPCC07C253/30C07C253/14C07C255/50
Inventor 卡玛尔·卡塔利亚维克·普拉萨德克里斯托弗·林恩·拉森卡梅龙·希思·吉布基里特·德赛阿什瓦妮·古普塔吉里什·索德
Owner ARYSTA LIFESCIENCE CORP
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