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Preparation method of nitrobenzoate

A technology of nitrobenzoate and fuming nitric acid, applied in the field of pesticides, can solve the problems of high processing cost, unfriendly environment, large amount of waste acid generated, etc., and achieves good reaction selectivity, easy control of reaction temperature, and high yield. rate increase effect

Pending Publication Date: 2020-07-03
NUTRICHEM LAB CO LTD
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  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to provide a kind of preparation method of nitrobenzoic acid ester in order to overcome the problems of large amount of waste acid in the prior art, unfriendly to the environment and high processing cost, which can reduce the amount of waste acid and Nitrobenzoate was obtained in high yield

Method used

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  • Preparation method of nitrobenzoate
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  • Preparation method of nitrobenzoate

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preparation example Construction

[0023] The preparation method of the nitrobenzoate of structure shown in formula (2) provided by the invention comprises: in the presence of halogenated hydrocarbon organic solvent, the compound of structure shown in formula (1) and fuming nitric acid, fuming The step of contacting sulfuric acid and acetic anhydride,

[0024]

[0025] In formula (1) and formula (2), X represents a halogen, and R represents an alkyl group having 1-8 carbon atoms.

[0026] In the present invention, with the halogenated benzoic acid ester of structure shown in formula (1) as raw material, with halogenated hydrocarbon organic solvent as solvent, with fuming nitric acid as nitrating reagent, fuming sulfuric acid as dehydrating agent, acetic anhydride Nitrification is carried out for reactive dehydration.

[0027] According to the method of the present invention, preferably, X is F, Cl or Br.

[0028] In the present invention, the "alkyl group having 1 to 8 carbon atoms" may be chain, branched ...

Embodiment 1

[0042] Compounding acid: In a 250ml flask, add fuming sulfuric acid (1.8mol, 3 equivalents), stir and cool down to 10°C, add fuming nitric acid (0.7mol, 1.2 equivalents) dropwise, control the temperature below 10°C, and cool after mixing spare.

[0043]Add raw materials methyl m-chlorobenzoate (0.6mol, 1 equivalent), acetic anhydride (0.6mol, 1 equivalent), 240g dichloroethane in the reaction flask, stir and cool down to minus 10°C, add mixed acid dropwise, and the dropping temperature does not exceed -5°C, heat up to 0°C, keep at 0°C for 2h. Separate the layers, separate the organic phase (upper layer), drop the acid layer into 100g of ice water to quench, add 240g of dichloroethane for extraction, separate the waste acid phase and combine the organic phase, add 100g of water to wash, separate the water phase; add the organic phase to Wash in the alkaline washing solution made of 10g sodium bicarbonate, 10g sodium carbonate and 180g water, separate the alkaline aqueous phase...

Embodiment 2

[0047] Compounding acid: In a 250ml flask, add fuming sulfuric acid (3mol, 5 equivalents), stir and cool down to 10°C, add fuming nitric acid (0.6mol, 1.2 equivalents) dropwise, control the temperature below 10°C, prepare and cool for later use .

[0048] Add raw materials isopropyl m-chlorobenzoate (0.6mol, 1 equivalent), acetic anhydride (0.72mol, 1.2 equivalents), 240g dichloroethane in the reaction flask, stir and cool down to minus 10°C, add mixed acid dropwise, the dropping temperature is constant When the temperature exceeds minus 5°C, the temperature is raised to 0°C, and the temperature is kept at 0°C for 2 hours. Separate the layers, separate the organic phase (upper layer), drop the acid layer into 100g of ice water to quench, add 240g of dichloroethane for extraction, separate the waste acid phase and combine the organic phase, add 100g of water to wash, separate the water phase; add the organic phase to Wash in the alkaline washing solution made of 10g sodium bic...

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Abstract

The invention relates to the field of pesticides, and particularly discloses a preparation method of nitrobenzoate, wherein the structure of the nitrobenzoate is represented by a formula (2). The preparation method of the nitrobenzoate comprises the step that in the presence of a halogenated hydrocarbon organic solvent, a compound with a structure represented by the formula (1) makes contact withfuming nitric acid, fuming sulfuric acid and acetic anhydride, wherein in the formula (1) and the formula (2), X represents halogen, and R represents alkyl with the carbon atom number being 1-8. According to the method, the amount of waste acid can be reduced, and nitrobenzoate can be obtained at high yield.

Description

technical field [0001] The invention relates to the field of pesticides, in particular to a preparation method of nitrobenzoate. Background technique [0002] 5-halo-2-nitrobenzoate compounds can be used as intermediates of medicine or pesticides (such as herbicide toxin, weed fire), and its structural formula is as follows: [0003] [0004] In the formula, X represents F, Cl or Br, R represents CH 3 、C 2 h 5 、C 3 h 7 、C 4 h 9 、C 5 h 11 、C 6 h 13 、C 7 h 15 、C 8 h 17 . [0005] Nitro-substituted m-halobenzoate is an important intermediate for the synthesis of the above two herbicides. Therefore, it is of great significance to find an environmentally friendly, high-yield, and easy-to-operate nitrification method for the industrial production of the above-mentioned herbicides. . [0006] "The synthesis of herbicide Maodu" (the first period of Northeast Agricultural Science Journal, 52-57, 1983) has reported that with 10 times of fuming nitric acid as nitrat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/08C07C205/58
CPCC07C201/08C07C205/58
Inventor 霍世勇张艳芳涂俊清路风奇付裕金辰
Owner NUTRICHEM LAB CO LTD
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