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Preparation method of N,N,N'-trimethyl-N'-hydroxyethyl diaminoethyl ether

A technology of bisaminoethyl ether and dimethylamino, which is applied in the field of polyurethane industry, can solve the problems of low atom economy, little application value, and complicated processing, and achieve high atom economy, low pollution, and low raw material cost Effect

Active Publication Date: 2018-07-06
安徽恒光聚氨酯材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method needs to consume a large amount of alkali, use thionyl chloride to generate a large amount of waste gas, and the atom economy is low. Nucleophilic substitution requires an equivalent amount of sodium hydroxide as an acid-binding agent to generate an equivalent salt, and the post-treatment of the generated salt is complicated and costly. ;It has little application value in industrial production

Method used

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  • Preparation method of N,N,N'-trimethyl-N'-hydroxyethyl diaminoethyl ether
  • Preparation method of N,N,N'-trimethyl-N'-hydroxyethyl diaminoethyl ether
  • Preparation method of N,N,N'-trimethyl-N'-hydroxyethyl diaminoethyl ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1, a kind of preparation method of 2-[2-(dimethylamino) ethoxyl] acetaldehyde, take chloroacetaldehyde dimethyl acetal and N, N-dimethylethanolamine as raw material, after adding first hydrolysis:

[0048] Add 12.4g (0.1mol) of chloroacetaldehyde dimethyl acetal, 8.9g (0.1mol) of N,N-dimethylethanolamine, 4.0g (0.1mol) of sodium hydroxide and 30ml of solvent toluene into a 250ml three-neck flask. Heat to reflux for 8 hours, cool down to room temperature after the reaction, and analyze the still liquid by gas chromatography. At this time, the conversion rate of the raw material (ie, N,N-dimethylethanolamine) is 91.8%, and the product yield is 88.3%.

[0049]Keep stirring at room temperature and slowly add concentrated hydrochloric acid (concentration: 37%) dropwise (control the temperature of the system not to exceed 50° C. during the dropwise addition) until pH=1. After the dripping, the layers were left to stand, and the water layer was taken for the next s...

Embodiment 1-1～ Embodiment 1-7

[0051] Change the reaction condition of nucleophilic substitution among the embodiment 1, promptly change the raw material mol ratio (N in the embodiment 1, N-dimethylethanolamine: chloroacetaldehyde dimethyl acetal, the consumption of N, N-dimethylethanolamine keeps constant), sodium hydroxide consumption, reflux time, solvent name (solvent consumption remains constant), and the resulting total yield is shown in Table 1.

[0052] Table 1

[0053] Example

1

1-1

1-2

1-3

1-4

1-5

1-6

1-7

Reaction time / h

8

6

7

8

9

10

8

8

Sodium hydroxide dosage / g

4.0

4.0

4.0

4.4

4.0

4.0

4.4

4.4

Raw material molar ratio

1

1.1

1.1

1.1

1.1

1.1

1.3

1.3

solvent

toluene

toluene

toluene

toluene

toluene

toluene

Cyclohexane

water

Raw material conversion rate / %

91.8

62.3

75.7

92.3

92.0

92.0

91.8

15.0

Product ...

Embodiment 2

[0066] Example 2, 2-[2-(dimethylamino)ethoxy]acetaldehyde and N-methylethanolamine hydroamination to prepare N,N,N'-trimethyl-N'-hydroxyethyl Aminoethyl ether:

[0067] 13.1 g (0.1 mol) of 2-[2-(dimethylamino)ethoxy]acetaldehyde, 8.3 g (0.1 mol) of N-methylethanolamine, 1.3 g of Raney Ni and 15 ml of methanol were put into a 100 ml autoclave. At room temperature (about 20°C), fill the kettle with hydrogen to 2.0MPa, heat to 120°C and stir for 8h, keeping the pressure inside the kettle (adjusted by hydrogen) at 2.0-2.2MPa.

[0068] After the reaction was completed, the temperature was cooled to room temperature and filtered. The obtained filter cake is immediately put into a concentrated sodium hydroxide solution with a mass concentration of 40% and soaked for at least 30 minutes, and then washed with clear water for several times (until the pH of the washing solution is about 8), and then Raney Ni can be recycled. The filtrate was analyzed by gas chromatography, and the conv...

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Abstract

The invention discloses a preparation method of N,N,N'-trimethyl-N'-hydroxyethyl diaminoethyl ether. The preparation method comprises the following steps: 1) in a solvent I, sequentially performing nucleophilic substitution and hydrolysis on N, N-dimethylethanolamine and chloroacetaldehyde dimethyl acetal which serve as raw materials to obtain 2-[2-(dimethylamino)ethyoxyl]acetaldehyde serving as an intermediate product; and 2) in a solvent II, mixing N-methylethanolamine and the 2-[2-(dimethylamino)ethyoxyl]acetaldehyde, performing hydrogenation amination on the mixture serving as a reaction system by taking Raney Ni as a catalyst to prepare the N,N,N'-trimethyl-N'-hydroxyethyl diaminoethyl ether. The N,N,N'-trimethyl-N'-hydroxyethyl diaminoethyl ether prepared by the method has the characteristics of simple process, low cost, high yield and low pollution.

Description

technical field [0001] The invention belongs to the polyurethane industry, and mainly relates to the synthesis of a polyurethane catalyst, that is, N, N, N'-trimethyl-N'-hydroxyethyl bisaminoethyl ether. Background technique [0002] N, N, N'-trimethyl-N'-hydroxyethyl bisaminoethyl ether, this product is currently only produced by Huntsman Corporation of the United States, and its product code is ZF-10, which belongs to the high-efficiency and low-odor foaming catalyst. There is no domestic production yet. [0003] According to comprehensive literature reports, the current synthesis has the following methods: [0004] 1. Patent JP2009215386 reported that N, N, N'-trimethyl-bisaminoethyl ether was used as raw material to prepare N, N'-trimethyl-N'-hydroxyethyl bisamino by reflux in acrylonitrile Ethyl ether; Patent CN101104674 reports a kind of N, N, N'-trimethyl-bisamino ethyl ether as raw material, reacts with glycidyl ether to prepare N, N'-trimethyl-N'-hydroxy Ethyl bi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/08C07C213/02C07C217/08
CPCC07C213/02C07C213/06C07C213/08C07C217/08
Inventor 张超魏梦怡张琪张华叶开天
Owner 安徽恒光聚氨酯材料有限公司
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