Preparation method of N, N'-bis(2, 2, 6, 6-tetramethyl-4-piperidyl)-1, 3-benzenedicarboxamide

A technology of phthalamide and isophthaloyl chloride, which is applied in the field of hindered amine light stabilizers, can solve the problems of many organic substances, ineffective utilization of raw materials, and other problems, achieves mild reaction conditions, is conducive to full utilization, The effect of reducing unit consumption

Active Publication Date: 2014-01-15
盘锦新秀新材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Aiming at the problems in the prior art that the raw materials are not effectively utilized, there are many organic substances in the production wastewater, and the hydrolysis of isophthaloyl dichloride and the pressure operation in the refining stage, the present invention provides a kind of N,N'-bis(2,2 , The production method of 6,6-tetramethyl-4-piperidinyl)-1,3-phthalamide has the advantages of good product quality, simple process, convenient operation and effective utilization of raw materials

Method used

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  • Preparation method of N, N'-bis(2, 2, 6, 6-tetramethyl-4-piperidyl)-1, 3-benzenedicarboxamide
  • Preparation method of N, N'-bis(2, 2, 6, 6-tetramethyl-4-piperidyl)-1, 3-benzenedicarboxamide
  • Preparation method of N, N'-bis(2, 2, 6, 6-tetramethyl-4-piperidyl)-1, 3-benzenedicarboxamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Put 700kg of methyl ethyl ketone and 184.4kg of 2,2,6,6-tetramethyl-4-aminopiperidine (according to the purity of 99%, 1.17kmol) into the reactor, stir and cool down to 0°C, slowly drop into the molten 92.3kg of phthaloyl chloride (99% purity, 0.45kmol) was kept at a reaction temperature of 10°C, and the reaction was incubated for 5 hours after the dropwise addition was completed. Centrifuge with a fully automatic closed centrifuge, wash the filter cake with anhydrous methyl ethyl ketone, collect the mother liquor and washing liquid for the next batch of production, and vacuum-dry the filter cake to obtain 227kg of intermediate (Ⅱ), with a yield of 98.7% (calculated as isophthaloyl chloride).

[0026] Put 227kg of the obtained intermediate (II) and 620kg of water into the reaction kettle and stir evenly. The reaction temperature is 25-30°C. Add about 125kg of 30% sodium hydroxide aqueous solution (0.94kmol) dropwise until the pH value of the reaction solution is 10, and...

Embodiment 2

[0028] Put 950kg of recovered mother liquor and 140.4kg of 2,2,6,6-tetramethyl-4-aminopiperidine (99% purity, 0.9kmol) into the reaction kettle, stir and cool down to 0°C, slowly drop Add 92.3kg of molten isophthaloyl chloride (0.45kmol based on 99% purity) to keep the reaction temperature at 15°C. After the dropwise addition, keep the reaction for 1 hour. Centrifuge with a fully automatic closed centrifuge, wash the filter cake with anhydrous methyl ethyl ketone, collect the mother liquor and washing liquid for the next batch of production, and vacuum dry the filter cake to obtain 228kg of intermediate (Ⅱ), with a yield of 99.6% (calculated as isophthaloyl chloride).

[0029] Put 228kg of the obtained intermediate (II) and 1200kg of water into the reaction kettle and stir evenly. The reaction temperature is 25-30°C. Add about 125kg of 30% sodium hydroxide aqueous solution (0.94kmol) dropwise until the pH value of the reaction solution is 10, and keep the reaction for 3 hours....

Embodiment 3

[0031]Put 1800kg of petroleum ether (60~90°C), 147.4kg of 2,2,6,6-tetramethyl-4-aminopiperidine (according to 99% purity, 0.945kmol) into the reactor, stir and cool down to -5°C , slowly dropwise added 92.3kg of molten isophthaloyl chloride (0.45kmol based on a purity of 99%) to keep the reaction temperature at 0°C, and kept the reaction for 5 hours after the dropwise addition was completed. Centrifuge with a fully automatic closed centrifuge, wash the filter cake with petroleum ether (60-90°C), collect the mother liquor and washing liquid for the next batch of production, and vacuum-dry the filter cake to obtain 228.8kg of intermediate (Ⅱ) , Yield 99.5% (based on isophthaloyl chloride).

[0032] Put 228.8kg of the obtained intermediate (II) and 450kg of water into the reaction kettle and stir evenly. The reaction temperature is 25-30°C. Add about 125kg of 30% sodium hydroxide aqueous solution (0.94kmol) dropwise until the pH value of the reaction solution is 10. Hours, centr...

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Abstract

The invention discloses a preparation method of N, N'-bis(2, 2, 6, 6-tetramethyl-4-piperidyl)-1, 3-benzenedicarboxamide which is represented by formula (I). The preparation method comprises following steps: (1) 2, 2, 6, 6-tetramethyl-4-aminopiperidine and m-phthalyl dichloride are taken as raw materials, and are reacted in an anhydrous organic solvent at a temperature of -5 to 25 DEG C until complete precipitation is realized, reaction liquid is filtered, and the filter cake is washed with the anhydrous organic solvent and dried so as to obtain an intermediate (II), wherein the anhydrous organic solvent is one selected from n-heptane, n-octane, petroleum ether, acetone or butanone; (2) at room temperature, the intermediate (II) is mixed uniformly with water, sodium hydroxide solution is added for neutralization, the mixture is filtered and washed with water so as to obtain a filter cake, and the filter cake is dried so as to obtain N, N'-bis(2, 2, 6, 6-tetramethyl-4-piperidyl)-1, 3-benzenedicarboxamide represented by formula (I). The preparation method possesses advantages of high product quality, simple operation technology, convenient operation process and high raw material utilization rate.

Description

(1) Technical field [0001] The invention relates to a preparation method of hindered amine light stabilizer-N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3-benzenedicarboxamide. (2) Background technology [0002] Nylon is a common name for polyamide polymers. It has high tensile strength and wear resistance. Light stabilizers must be added to nylon products to prevent or delay the material from photothermal oxidation and degradation and aging, and to maintain the material during the service life. excellent performance. [0003] The present invention relates to a hindered amine light stabilizer as shown in formula I, its chemical name is: N,N'-di(2,2,6,6-tetramethyl-4-piperidinyl)-1, 3-phthalamide: [0004] [0005] The light stabilizer product of the present invention is mainly used in nylon and has good compatibility with nylon; it can improve the processing performance of nylon melt such as: reduce broken filaments during fiber spinning; the hindered amine group in it...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/58C08K5/3435
CPCC07D211/58C08K5/3435
Inventor 仵大伟
Owner 盘锦新秀新材料有限公司
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