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

A technology of bisaminoethyl ether and dimethylaminoethoxyethanol is applied in the synthesis field of polyurethane catalyst, can solve the problems of unfavorable industrial production, low atom economy, low application value, etc. Product yield, high atom economy, and low pollution

Inactive Publication Date: 2018-05-29
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] 1. Patents JP2009215386 and CN101104674 report a kind of N,N'-trimethyl-N'-hydroxyethylbisaminoethyl ether prepared from N,N,N'-trimethyl-bisaminoethyl ether Ether, but N, N, N'-trimethyl-bisaminoethyl ether source is inconvenient, is unfavorable for the industrialized production of this method
And this method prepares target product with above-mentioned raw material and acrylonitrile reaction, and acrylonitrile is highly toxic, and environment is unfriendly
[0004] 2. Patent CN105884629 reports a kind of N, N, N'-trimethyl-N'-hydroxyethyl

Method used

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

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Embodiment 1

[0044] Embodiment 1, a kind of synthetic method of 2-[2-(dimethylamino)ethoxyl]acetaldehyde, take dimethylaminoethoxyethanol as raw material, 2,2,6,6-tetramethylpiperene Pyroxyl-FeCl 3 - tert-butyl nitrite catalysis:

[0045] 13.3g of dimethylaminoethoxyethanol, 1.248g of 2,2,6,6-tetramethylpiperidine oxide, 0.824g of tert-butyl nitrite, 1.248g of FeCl were put into a 100ml autoclave 3 and 15ml of dichloromethane.

[0046] Fill the kettle with oxygen to 0.6MPa at room temperature, heat to 80°C and stir for 8h. After the reaction was finished, it was lowered to room temperature, and the pressure inside the kettle was 0.2 MPa (20° C.). Then the still liquid is subjected to the following post-treatment: filtration, and the resulting filtrate is distilled under reduced pressure (25 Torr pressure, collecting fractions at 75-80° C.) to obtain 8.02 g of colorless and transparent 2-[2-(dimethylamino)ethoxy base] acetaldehyde. The conversion rate of the raw material obtained after...

Embodiment 1-1～ Embodiment 1-9

[0048] Change the following reaction conditions in embodiment 1: change temperature of reaction in embodiment 1, reaction pressure, catalyst ratio (change the mass ratio of 2,2,6,6-tetramethyl piperidine oxide and tert-butyl nitrite , the amount of 2,2,6,6-tetramethylpiperidinium oxide remains unchanged), the kind of solvent; all the other are equal to embodiment 1 (FeCl 3 The dosage ratio remains unchanged); thus, Examples 1-1 to 1-9 are obtained, and the total yield is shown in Table 1.

[0049] Table 1

[0050]

[0051]Embodiment 1-10~1-17, change the following reaction conditions in embodiment 1: change the reaction time in embodiment 1, catalyst 2,2,6,6-tetramethylpiperidinium oxide accounts for two Methylaminoethoxyethanol mass ratio, all the other are equal to embodiment 1 (that is, the mass ratio of 2,2,6,6-tetramethylpiperidine oxide and tert-butyl nitrite remains constant, FeCl 3 The mass ratio to 2,2,6,6-tetramethylpiperidinium oxide remains unchanged); thus, E...

Embodiment 2

[0054] Example 2, 2-[2-(Dimethylamino)ethoxy]acetaldehyde and methylethanolamine hydrogenation amination to prepare N,N,N'-trimethyl-N'-hydroxyethylbisaminoethyl Base ether:

[0055] 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.

[0056] After the reaction was completed, it was lowered to room temperature and filtered. Gained filter cake is dropped into concentrated sodium hydroxide solution (mass concentration is 40% sodium hydroxide aqueous solution) immediately and soaks at least 30 minutes, then washes repeatedly with clear water (to washing liquid pH is about 8), the Raney Ni of gained can be recycle. The filtrate was analyzed by gas chromatography, and the conv...

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Abstract

The invention discloses a synthesis method of N, N, N'-trimethyl-N'-hydroxyethyl diaminoethyl ether. The synthesis method comprises the following steps of: in a solvent I, adopting dimethylaminoethoxyethanol as a raw material, and under a catalytic system of 2, 2, 6, 6-tetramethyl piperidinoxide-FeCl3-tertbutyl nitrite, utilizing oxygen gas to oxidize the dimethylaminoethoxyethanol into 2-[2-(dimethylamino)ethoxy]acetaldehyde; in a solvent II, mixing N-methylethanolamine with the 2-[2-(dimethylamino) ethoxy]acetaldehyde, adopting Raney Ni as a catalyst, adopting the above mixture as a reactionsystem to carry out hydrogenation and amination, and preparing the N, N, N'-trimethyl-N'-hydroxyethyl diaminoethyl ether. The N, N, N'-trimethyl-N'-hydroxyethyl diaminoethyl ether synthesized by adopting the synthesis method has the characteristics of simple process, low cost, high yield and less pollution.

Description

technical field [0001] The invention belongs to the polyurethane industry, and mainly relates to the synthesis of a polyurethane catalyst, that is, the synthesis method of N, N, N'-trimethyl-N'-hydroxyethyl bisaminoethyl ether. Background technique [0002] N, N, N'-trimethyl-N'-hydroxyethyl bisaminoethyl ether belongs to low-odor foaming catalyst, and its main synthesis methods are as follows: [0003] 1. Patents JP2009215386 and CN101104674 report a kind of N,N'-trimethyl-N'-hydroxyethylbisaminoethyl ether prepared from N,N,N'-trimethyl-bisaminoethyl ether Ether, but the source of N, N, N'-trimethyl-bisaminoethyl ether is inconvenient, which is not conducive to the industrial production of this method. Moreover, the method prepares the target product by reacting the above-mentioned raw materials with acrylonitrile, which is highly toxic and environmentally unfriendly. [0004] 2. Patent CN105884629 reports a kind of N, N, N'-trimethyl-N'-hydroxyethyl bisamino produced by...

Claims

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Application Information

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IPC IPC(8): C07C213/02C07C217/08C08G18/18
CPCC07C213/02C07C213/08C08G18/1833C07C217/08
Inventor 陈新志魏梦怡钱超
Owner ZHEJIANG UNIV
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