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Green production process of nicosulfuron intermediate nicotinamide and sulfonamide

A technology for nicotinamide and nicosulfuron is applied in the field of preparation of herbicide intermediates, which can solve problems such as water body eutrophication and environmental pollution, and achieve the effects of low cost, reduced production cost, and reduced processing difficulty and cost.

Pending Publication Date: 2022-03-11
江苏丰山生化科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, these two amination reaction sections will produce a large amount of high-concentration ammonia-nitrogen wastewater, which will cause eutrophication of the water body and pollute the environment

Method used

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  • Green production process of nicosulfuron intermediate nicotinamide and sulfonamide
  • Green production process of nicosulfuron intermediate nicotinamide and sulfonamide
  • Green production process of nicosulfuron intermediate nicotinamide and sulfonamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] 1) Preparation of nicotinamide:

[0055] Add 90g of dichloroethane, 11.3g (0.1mol) of 40% dimethylamine aqueous solution, 4.8g (0.12mol) of NaOH and 16.2g of water into the flask, cool down to below 0°C, and start to drop the prepared 66.5 g nicotinyl chloride solution (0.098mol), the dropwise addition temperature is controlled at -10°C to 0°C. At the end of the dropwise addition, keep warm for 1 hour, separate layers, and desolventize the organic layer under negative pressure to obtain 18.3 g of nicotinamide with a content of 95.8% and a yield of 96.9%. The content of ammonia nitrogen in the amination wastewater is 2218 mg / L.

[0056] 2) Preparation of 2-(sulfonyl chloride)-N,N-dimethyl-3-pyridinecarboxamide

[0057] Add nicotinamide, sulfur, sodium sulfide and water into the flask, raise the temperature to 110-120°C and keep it warm for 6h. After the reaction, adjust the pH to 2-3 with hydrochloric acid, and then filter; add a certain amount of dichloromethane to th...

Embodiment 2

[0062] 1) Preparation of nicotinamide

[0063] Add 82g of dichloroethane, 13.5g (0.12mol) of 40% dimethylamine aqueous solution, 4.8g (0.12mol) of NaOH and 16.2g of water into the flask, lower the temperature to below 0°C, and start to drop the prepared 66.5 g nicotinyl chloride solution (0.098mol), the dropwise addition temperature is controlled at -10°C to 0°C. At the end of the dropping, keep warm for 1 hour, separate layers, and desolventize the organic layer under negative pressure to obtain 18.36 g of nicotinamide with a content of 96.3% and a yield of 97.8%. The content of ammonia nitrogen in the amination wastewater is 4742 mg / L.

[0064] 2) Preparation of 2-(sulfonyl chloride)-N,N-dimethyl-3-pyridinecarboxamide

[0065] Add nicotinamide, sulfur, sodium sulfide and water into the flask, raise the temperature to 110-120°C and keep it warm for 6h. After the reaction, adjust the pH to 2-3 with hydrochloric acid, and then filter; add a certain amount of dichloromethane t...

Embodiment 3

[0069] 1) Preparation of nicotinamide

[0070] Add 82g of dichloroethane, 12.38g (0.11mol) of 40% dimethylamine aqueous solution, and 17.33g (0.13mol) of 30% sodium hydroxide aqueous solution into the flask, cool down to below 0°C, and start to drop the prepared 66.5g of nicotinyl chloride solution (0.098mol), the dropwise addition temperature is controlled at -10°C to 0°C. At the end of the dropping, keep warm for 1 hour, separate layers, and desolventize the organic layer under negative pressure to obtain 18.25 g of nicotinamide with a content of 96.4% and a yield of 97.3%. The content of ammonia nitrogen in the amination wastewater is 3576 mg / L.

[0071] 2) Preparation of 2-(sulfonyl chloride)-N,N-dimethyl-3-pyridinecarboxamide

[0072] Add nicotinamide, sulfur, sodium sulfide and water into the flask, raise the temperature to 110-120°C and keep it warm for 6h. After the reaction, adjust the pH to 2-3 with hydrochloric acid, and then filter; add a certain amount of dichlo...

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Abstract

The invention relates to a green production process of nicosulfuron intermediates nicotinamide and sulfonamide, which comprises the following steps of: in the preparation process of 2-chloro-N, N-dimethyl nicotinamide and 2-aminosulfonyl-N, N-dimethyl nicotinamide, replacing excessive dimethylamine solution or ammonia water by using inorganic base as an acid-binding agent, neutralizing hydrogen chloride generated in reaction, and reacting to obtain 2-chloro-N, N-dimethyl nicotinamide and 2-aminosulfonyl-N, N-dimethyl nicotinamide; the inorganic base is sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate, and the dosage of the inorganic base is strictly limited, so that high reaction yield and purity are ensured, new impurities are not generated, a large amount of ammonia nitrogen is prevented from entering the wastewater, and the total nitrogen in the wastewater is reduced by more than 90% compared with a traditional process; the wastewater treatment difficulty and cost are reduced, and meanwhile, the raw material cost is also reduced.

Description

technical field [0001] The invention belongs to the field of preparation of herbicide intermediates, and in particular relates to a green production process of nicosulfuron intermediates nicotinamide and sulfonamide. Background technique [0002] Nicosulfuron is a broad-spectrum, high-efficiency, low-toxicity, low-residue sulfonylurea herbicide, and it is one of the best cornfield herbicide varieties so far. [0003] The two key intermediates of nicosulfuron are 2-chloro-N,N-dimethylnicotinamide (nicotinamide) and 2-aminosulfonyl-N,N-dimethylnicotinamide (sulfonamide). The route generally uses 2-chloronicotinic acid as the starting material. Niacinamide is prepared from 2-chloronicotinic acid through acid chloride reaction and amination reaction. Sulfonamide is prepared from nicotinamide through sulfhydryl reaction, chlorine oxidation reaction and ammoniation reaction. [0004] The main synthesis method of nicotinamide is as follows: [0005] CN101117332A and JP59-144759 r...

Claims

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Application Information

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IPC IPC(8): C07D213/82
CPCC07D213/82
Inventor 瞿保华顾蓉宋媛媛孙旭峰王晋阳王波单永祥殷平殷凤山
Owner 江苏丰山生化科技有限公司
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