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Applications of L-arginine and derivative of L-arginine in preparation of cyclododecanoneoxime, and method used for preparing cyclododecanoneoxime

A technology of arginine derivatives and cyclododecanone oxime, which is applied in the preparation of cyclododecanone oxime and the field of preparation of cyclododecanone oxime through cyclododecanone, can solve the unsolved problem of hydroxylamine stability and reaction by-products , containing some impurities such as hydroxylamine stability, long reaction time of cyclododecanone oximation, etc., to achieve the effect of eliminating the purification process, good stability and high cost performance

Active Publication Date: 2019-11-26
WANHUA CHEM GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The patent mentions that adding carboxylic acid / carboxylate can speed up the oximation reaction and reduce the reaction time, but it does not solve the problem of hydroxylamine stability and reaction by-products
[0010] Therefore, in view of the technical problems in the above-mentioned patents, an auxiliary agent and a new process are needed to solve the problems of long reaction time of traditional cyclododecanone oximation, some impurities and the stability of hydroxylamine in the reaction raw materials.

Method used

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  • Applications of L-arginine and derivative of L-arginine in preparation of cyclododecanoneoxime, and method used for preparing cyclododecanoneoxime
  • Applications of L-arginine and derivative of L-arginine in preparation of cyclododecanoneoxime, and method used for preparing cyclododecanoneoxime

Examples

Experimental program
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Effect test

Embodiment 1

[0041] A 1.0L glass stirred tank reactor was used as the oximation reaction vessel, and the stirred tank rotating speed was maintained at 1000rpm, and 450g Raschig solution (hydroxylamine sulfate content 12.5wt%), 190g 30wt% cyclododecanone isopropyl ring was added in advance. Hexane solution, the detected iron ion content is 158ppm, then add 15g L-arginine-L-glutamic acid as an auxiliary agent, and add ammonia water dropwise at a flow rate of 2.9g / min for 15min, the reaction temperature is controlled at 90°C, the pH Control the time between 4.5 and 6.5, use GC to track the reaction, and ICP to analyze the iron ion content in the reaction process to be 0.4ppm.

[0042] Until the conversion rate of cyclododecanone reaches more than 99.8%, the reaction time is calculated and the utilization rate of reactants is analyzed. Then add ammonia water to adjust the pH to 7.5, lower the temperature to 65°C, separate the oil and water phases, filter and recover the additives. According t...

Embodiment 2

[0044] This embodiment is with respect to embodiment 1, and difference is that the auxiliary agent that adds is the L-arginine of 15g, all the other and embodiment 1 conditions are identical, find according to analysis result, reaction time is 4.1 hours, the decomposition of hydroxylamine sulfate in the reactant The ratio is 1.2%, and the cyclododecanoneimine content is 6.5ppm (based on the total mass of the reaction solution). The conversion rate of cyclododecanone is 99.9%, the selectivity of cyclododecanone oxime is 99.992%, and the iron ion content in the reaction process is 0.9ppm.

Embodiment 3

[0046] Compared with Example 1, this example is different in that the auxiliary agent added is 15g of L-arginine succinate, and all the other conditions are the same as in Example 1. According to the analysis results, it is found that the reaction time is 2 hours, and hydroxylamine sulfate in the reactant The decomposition rate is 0.5%, and the cyclododecanone imine content is 1.6ppm (based on the total mass of the reaction solution). The conversion rate of cyclododecanone is 99.9%, the selectivity of cyclododecanone oxime is 99.998%, and the iron ion content in the reaction process is 0.1ppm.

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Abstract

The invention discloses applications of L-arginine and a derivative of L-arginine in preparation of cyclododecanoneoxime, and a method used for preparing cyclododecanoneoxime. The derivative of L-arginine comprises one or a plurality of components selected from L-arginine-L-glutamic acid, an L-arginine hydrochloride, and an L-arginine succinate. According to the preparation method, one or more than one components selected from L-arginine and the derivative of L-arginine are taken as auxiliary agents, cyclododecanone is reacted with hydroxylamine sulphate to prepare cyclododecanoneoxime. The auxiliary agents are capable of controlling iron ion content in the reaction system, inhibiting hydroxylamine sulphate decomposition, inhibiting cyclododecylamine generation, and increasing reaction selectivity, and are convenient to separate and recycle.

Description

technical field [0001] The present invention relates to the use of a compound, in particular to the use of L-arginine and its derivatives for preparing cyclododecanone oxime, and also to a method for preparing cyclododecanone oxime through cyclododecanone. Background technique [0002] Cyclododecanone oxime can be rearranged to produce laurolactam, which is a monomer of nylon dodeca. In industry, cyclododecanone and hydroxylamine sulfate are commonly used to react to form cyclododecanone oxime, and there are many literatures about the oximation reaction. [0003] A method is described in GB1126495A, which uses cyclododecanone and hydroxylamine sulfate under the condition of pH=3-5, and uses hexahydrocumene as a solvent to undergo an oximation reaction to obtain cyclododecanone oxime, and simultaneously The use of two-stage countercurrent operations reduces the consumption of hydroxylamine sulfate, but does not mention how to solve the problem of the slower reaction rate of ...

Claims

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Application Information

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IPC IPC(8): C07C249/08C07C251/42
CPCC07C249/08C07C2601/20C07C251/42
Inventor 傅滋春丛振霞崔娇英陈雁玲林少宁乔小飞于天勇
Owner WANHUA CHEM GRP CO LTD
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