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Preparation method of N-hydroxysuccinimide

A technology of hydroxysuccinimide and hydroxylamine, which is applied in organic chemistry and other fields, and can solve problems such as high safety hazards, high chemical dangers, and high prices

Active Publication Date: 2018-09-21
泰安科赛尔化学科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this process uses a large amount of diethyl ether (boiling point is 34.5 ° C, standard air pressure), and there is a high potential safety hazard in the production process.
In addition, succinic anhydride is used as a raw material in the prior art, which is chemically dangerous and expensive, which seriously restricts the production cost of N-hydroxysuccinimide

Method used

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  • Preparation method of N-hydroxysuccinimide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] First, 160 grams of succinic acid and 59.5 grams of sodium hydroxide are reacted to generate succinic acid sodium salt.

[0035] Install a mechanical stirrer, a spherical condenser with a water separator, and a thermometer in a four-neck round bottom flask, and then add 400 mL of toluene. In an oil bath (temperature 140° C.), heat and reflux for dehydration until no water comes out. Cool the reaction system to room temperature, continue to add succinic acid sodium salt, 144 g of hydroxylamine sulfate, and 4.5 g of boric acid, and continue to heat and reflux for dehydration until the reaction is basically no dehydration. Cool the reaction system, transfer the toluene, add 400ml of absolute ethanol to reflux to extract the product for 20-30 minutes, cool the reaction system and remove the by-product sodium sulfate by suction filtration, and wash the filter cake three times with absolute ethanol.

[0036] Concentrate the mother liquor obtained above under normal pressure,...

Embodiment 2

[0038]Install a mechanical stirrer, a spherical condenser with a water separator, and a thermometer in a four-neck round bottom flask, and then add 400 mL of toluene. In an oil bath (temperature 140° C.), heat and reflux for dehydration until no water comes out. Cool the reaction system to room temperature, continue to add 160 grams of succinic acid, 144 g of hydroxylamine sulfate, 4.5 g of boric acid, and 59.5 grams of sodium hydroxide, and continue to heat and reflux for dehydration until the reaction is basically no dehydration. Cool the reaction system, transfer the toluene, add 400ml of absolute ethanol to reflux to extract the product for 20-30 minutes, cool the reaction system and remove the by-product sodium sulfate by suction filtration, and wash the filter cake three times with absolute ethanol.

[0039] Concentrate the mother liquor obtained above under normal pressure, and change the distillation under reduced pressure to remove ethanol as much as possible when the...

Embodiment 3

[0041] Succinic acid 1180g, sodium hydroxide 440g, hydroxylamine sulfate 1066g, boric acid 33g, succinic acid was added twice to produce product NHS830g, yield 72%, liquid chromatography detection content 99.48%, melting point 95-97 ℃.

[0042] Specific operation: 649g of succinic acid, 440g of sodium hydroxide, 2000mL of toluene, reflux dehydration for 1 hour, then add 531g of succinic acid, 1066g of hydroxylamine sulfate, 33g of boric acid, and 1000ml of toluene for dehydration, and the dehydration time is 6.5 hours. Pour out the toluene, then dissolve the solid with 2000ml of absolute ethanol (heat to reflux for 30min), condense and filter with suction, and wash the filter cake with absolute ethanol three times. Evaporate the ethanol to dryness under reduced pressure, add 2000ml of ethyl acetate to heat and extract the product, reflux for 30min, stand still and cool down to 60°C, separate the ethyl acetate and continue to cool down to room temperature, return the mother liqu...

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Abstract

The invention provides a preparation method of N-hydroxysuccinimide, which uses succinic acid as raw materials and reacts with hydroxylamine in the presence of weak acidic substances to prepare the N-hydroxysuccinimide. The reaction yield is over 85 percent, thereby further reducing production cost and eliminating hidden dangers existing in the production process.

Description

technical field [0001] The invention relates to a preparation method of N-hydroxysuccinimide, specifically a method for synthesizing N-hydroxysuccinimide by using succinic acid, hydroxylamine and boric acid as catalysts, belonging to the field of organic fine synthesis. Background technique [0002] N-Hydroxysuccinimide (NHS), English name: N-Hydroxy succinimide, also known as: N-Hydroxysuccinimide (HOSU), CAS: 6066-82-6, EINECS: 228-001-3, Molecular formula: C 4 h 5 NO 3 , molecular weight: 115.0874. [0003] N-Hydroxysuccinimide is an extremely important class of fine chemicals and chemical raw materials. Due to the active nitrogen hydroxyl group in the structure, it can be covalently covalent with the amino group, carboxyl group or sugar group of antigens, antibodies, enzymes and their nucleic acids. Combination, the combination will not affect their activity, so it can be often used as the precursor of synthetic peptides, antibiotics, amino acids, proteins, etc., as ...

Claims

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Application Information

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IPC IPC(8): C07D207/46
CPCC07D207/46
Inventor 唐行亮牛保卫杨丰科刘公军李瑞英王鑫张乾李明
Owner 泰安科赛尔化学科技有限公司
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