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Reaction of glycolaldehyde

A glycolaldehyde, reaction technology, applied in the field of reaction of glycolaldehyde and aminating agent, can solve the problem of reducing the yield of the target product, etc.

Pending Publication Date: 2020-11-20
塔明克私人有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Furthermore, glycolaldehyde, being a CH-acidic compound, has a high tendency to polymerize in aldol condensation or undergo Maillard reactions in the presence of amines, which form highly colored products and reduce the yield of the target product

Method used

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  • Reaction of glycolaldehyde
  • Reaction of glycolaldehyde
  • Reaction of glycolaldehyde

Examples

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example

[0142] The examples are to be understood as illustrating the method according to the invention. However, these examples should not be construed as limiting the scope of the invention.

[0143] Examples 1–6

[0144] In an electrically heated 50 ml autoclave (Hastelloy) with a mechanical magnetic stirrer was charged 0.5 g of commercially available dimer glycolaldehyde in a specific organic solvent (15 ml) and 200 μl of triethylene glycol dimethyl ether as an internal mark. Subsequently, the amount of catalyst specified in Table 1 was added. Dimethylamine was then metered in according to the molar ratios specified in Table 1 (dimethylamine:monomeric glycolaldehyde), the mixture was pressurized to 70 bar hydrogen and heated to 100°C. Stirring was carried out at 100°C for 1 hour under a specified pressure. The reaction product was filtered from the catalyst after 1 hour and analyzed by GC (carbon percentage, refers to the amount of carbon atoms of the substrate that can be dete...

example 7-11

[0151] An electrically heated 50 ml autoclave (Hastelloy) with a mechanical magnetic stirrer was charged with 1 g of commercially available dimer glycolaldehyde in a specific organic solvent (25 ml) and 400 μl of triglyme as an internal standard . Subsequently, the amount of catalyst specified in Table 2 was added. Ammonia was then metered in according to the molar ratios specified in Table 2 (ammonia:monomeric glycolaldehyde), the mixture was pressurized to 70 bar hydrogen and heated to 100°C. Stirring was carried out at 100°C for 1 hour under a specified pressure. The reaction product was filtered from the catalyst after 1 hour and analyzed by GC (carbon percentage, refers to the amount of carbon atoms of the substrate that can be detected as the final product, referenced to internal standard). The conversion was 100%, the difference from 100% mass balance was the unidentified minor component.

example 12-15

[0158] An electrically heated 50 ml autoclave (Hastelloy) with a mechanical magnetic stirrer was charged with 1 g of commercially available dimer glycolaldehyde in a specific organic solvent (25 ml) and 200 μl of triglyme as an internal standard . Subsequently, the amount of catalyst specified in Table 3 was added. Then, monomethylamine was metered in according to the molar ratio specified in Table 3 (monomethylamine:monomeric glycolaldehyde), the mixture was pressurized to 70 bar hydrogen and heated to 100°C. Stirring was carried out at 100°C for 1 hour under a specified pressure. The reaction product was filtered from the catalyst after 1 hour and analyzed by GC (carbon percentage, refers to the amount of carbon atoms of the substrate that can be detected as the final product, referenced to internal standard). The conversion was 100%, the difference from 100% mass balance was the unidentified minor component.

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Abstract

A two-step one-pot process for reacting glycolaldehyde with an aminating agent in the presence of a reactive organic fluid for instance a reactive solvent is provided. The first step comprises of contacting glycolaldehyde with an aminating agent in the presence of a reactive fluid for instance a reactive solvent under inert atmosphere to produce unsaturated intermediates, and reacting the reactionmixture obtained in step 1 with hydrogen in the presence of a supported hydrogenation catalyst in a second step.

Description

technical field [0001] The present invention relates to the reaction of glycolaldehyde with an aminating agent in a two-step process and in the presence of a reaction fluid, such as a reaction organic liquid. Background technique [0002] Industrially, (N-substituted) alkanolamines are almost exclusively produced by reacting ethylene oxide with ammonia or other primary, secondary or tertiary amines. Diamines are usually produced by reacting the aforementioned amines with 1,2-dichloroethane, ethylene glycol or monoethanolamine. It is also possible to perform sequential reactions to give higher alkanolamines, for example diethanolamine or triethanolamine if ammonia is used, but also heterocyclic compounds such as piperazine due to intramolecular reactions. These (N-substituted) alkanolamines and diamines are generally applicable in the production of emulsifiers, detergent raw materials, textile chemicals, curing agents, gas purification, agrochemicals, etc. [0003] However,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/26C07C213/02C07C213/08C07C215/12C07C211/14
CPCC07C209/26C07C213/02C07C213/08C07C215/12C07C211/14B01J21/18B01J23/44B01J23/462
Inventor 威廉·亨德里克·法维埃伯特·泽尔斯米歇尔·朱尔斯·Y·派尔克曼斯
Owner 塔明克私人有限公司
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