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Synthesis method of diisopropyl azodicarboxylate

A technology of diisopropyl azodicarboxylate and isopropyl formate, which is applied in the field of synthesis of diisopropyl azodicarboxylate, can solve the problems of large energy consumption, environmental pollution, and low yield, and achieve product yield High efficiency, high product purity and less by-products

Inactive Publication Date: 2015-04-01
SUZHOU JONATHAN NEW MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The currently disclosed synthetic methods of diisopropyl azodicarboxylate mainly use diisopropyl hydrazine dicarboxylate as a raw material, and are obtained by oxidation under different conditions. These methods generally have large energy consumption, low yield, and environmental pollution. serious problem

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Under the protection of nitrogen, add 40g of sodium methoxide and 300ml of anhydrous dimethyl sulfoxide to the three-necked flask, slowly add 100g of isopropyl carbazate and 100g of diethyl carbonate in sequence, raise the temperature to 120°C for 3 hours, cool down, and dissolve the solution Adjust the pH value to 5 with hydrochloric acid with a mass fraction of 10%, and filter with suction to obtain diisopropyl hydroazodicarboxylate;

[0023] At -20°C to 25°C, add diisopropyl hydroazodicarboxylate into 300ml of sulfuric acid solution with a mass fraction of 40%, after dissolving, slowly add 5g of bromine, and then control the reaction temperature at -15°C to -5 At ℃, add hydrogen peroxide with a mass fraction of 10% until no longer exothermic, continue to react for 6 hours after dropping, quench with sodium bisulfite, extract with dichloromethane, wash the organic layer with water until neutral, dry the organic layer with anhydrous sodium sulfate layer, filtered and c...

Embodiment 2

[0026] Under the protection of nitrogen, add 70g of sodium ethylate and 350ml of anhydrous sulfolane to the three-necked flask, slowly add 100g of isopropyl carbazate and 120g of diethyl carbonate in sequence, raise the temperature to 170°C for 4 hours, cool down, and mix the solution with a mass fraction of Adjust the pH value to 6 with 30% hydrochloric acid, and filter with suction to obtain diisopropyl hydroazodicarboxylate;

[0027] At -20°C to 25°C, add diisopropyl hydroazodicarboxylate into 350ml of sulfuric acid solution with a mass fraction of 45%. After dissolving, slowly add 5g of hydrobromic acid, and then control the reaction temperature at -15°C to At -5°C, add hydrogen peroxide with a mass fraction of 15% dropwise until the heat release ceases, continue the reaction for 7 hours after dropping, quench with sodium thiosulfate, extract with dichloromethane, wash the organic layer with water until neutral, anhydrous magnesium sulfate The organic layer was dried, filt...

Embodiment 3

[0030] Under the protection of nitrogen, add 45g of potassium methylate and 350ml of anhydrous sulfolane to the three-necked flask, slowly add 100g of isopropyl carbazate and 110g of diethyl carbonate in sequence, raise the temperature to 150°C for 6 hours, cool down, and prepare the solution with a mass fraction of Adjust the pH value to 7 with 20% hydrochloric acid, and filter with suction to obtain diisopropyl hydroazodicarboxylate;

[0031] At -20°C to 25°C, add diisopropyl hydroazodicarboxylate into 300ml of sulfuric acid solution with a mass fraction of 50%, after dissolving, slowly add 5g of sodium bromide, and then control the reaction temperature at -15°C to Add hydrogen peroxide with a mass fraction of 12% dropwise at -5°C until the heat release ceases, continue the reaction for 5 hours after dropping, quench with sodium thiosulfate, extract with dichloromethane, wash the organic layer with water until neutral, anhydrous sodium sulfate The organic layer was dried, fi...

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PUM

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Abstract

The invention discloses a synthesis method of diisopropyl azodicarboxylate. The synthesis method comprises the following steps: (1) adding alkali and a solvent under protection of inert gases, sequentially adding carbazic acid isopropyl ester and diethyl carbonate, carrying out heating reaction at 100-180 DEGC for 2-6 hours, adjusting the pH value of a solution to 4.5-7.5 with acid, and carrying out suction filtration, so as to obtain hydrogenated diisopropyl azodiformate; and (2) adding 40%-50% of sulfuric acid solution to the hydrogenated diisopropyl azodiformate at -20 DEG C to 25 DEG C, dissolving, adding a catalyst, controlling the reaction temperature to -15 DEG C to -5 DEG C, dropwise adding 10%-15% of hydrogen peroxide until no heat is emitted, further reacting for 5-10 hours after dropwise adding is ended, quenching, extracting, washing to be neutral, drying, filtering, and concentrating to obtain the diisopropyl azodiformate. The synthesis method disclosed by the invention is clean and environmental friendly in raw material, mild in reaction condition, and few in byproducts; and the product is high in yield and beneficial to industrialized production.

Description

technical field [0001] The invention relates to a synthesis method of diisopropyl azodicarboxylate, which belongs to the technical field of organic synthesis. Background technique [0002] Azodicarboxylate diesters are widely used intermediates with both azo and carboxyl functional groups, especially as Mitsunobu cyclization reagents, and Mitsunobu reactions are used to synthesize some important heterocyclic compounds. Diisopropyl azodicarboxylate (DIAD for short) is an important member of this kind of cyclization reagents. Diisopropyl azodicarboxylate can not only be used in the synthesis of photosensitizers, polymerization catalysts, fungicides and other products, but also can be used As a liquid foaming agent, it has good miscibility with plastics, and its decomposition products are colorless, pollution-free, and odor-free, with broad application prospects. [0003] The currently disclosed synthetic methods of diisopropyl azodicarboxylate mainly use diisopropyl hydrazine...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/04
Inventor 李卓才李苏杨
Owner SUZHOU JONATHAN NEW MATERIALS TECH
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