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Preparation of N, N-di(2-ethoxyl) aminomethyl diethyl phosphoric acid

A technology of diethyl aminomethylphosphonate and hydroxyethyl, which is applied in the field of preparation of diethyl aminomethylphosphonate, can solve the problems of low yield, difficult separation of by-products, and low content, and achieve a simple preparation method , The effect of improving product quality and improving yield

Inactive Publication Date: 2005-02-23
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the presence of water, phosphite and product phosphonate are easy to hydrolyze under the reaction conditions, and ethyl substitution reaction is also easy to occur on the nitrogen atom of diethanolamine. It is difficult to separate the by-products from the reaction system. Using this method to prepare N, the yield of N-bis(2-hydroxyethyl)aminomethylphosphonic acid diethyl ester product is low. In the product, N,N-bis(2- The content of diethyl hydroxyethyl) aminomethyl phosphonate is not high

Method used

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  • Preparation of N, N-di(2-ethoxyl) aminomethyl diethyl phosphoric acid
  • Preparation of N, N-di(2-ethoxyl) aminomethyl diethyl phosphoric acid

Examples

Experimental program
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Effect test

Embodiment 1

[0016] (1) Add 165 parts of 37% formaldehyde aqueous solution into the reactor, heat to 30° C., add 206 parts of pre-melted diethanolamine within 30 minutes under stirring. The process of adding diethanolamine is an exothermic reaction, keep the reaction temperature at 30° C., and react for 1 hour.

[0017] (2) Change the reaction device to vacuum distillation. At 50° C., the pressure is less than 0.095 MPa. Water is distilled off under reduced pressure, and then the vacuum distillation is continued for 2 hours at 60° C.

[0018] (3) Change the distillation device back to the reaction device, and lower the temperature to 40°C, add 0.8 parts of anhydrous solid acid catalyst macroporous strong acid cationic resin, add 271 parts of diethyl phosphite within 1 hour under stirring, and then The reaction was incubated at 50°C for 2 hours.

[0019] (4) The reaction material was cooled to room temperature, and the catalyst was recovered by filtration to obtain a yellow transparent liq...

Embodiment 2

[0020] Example 2. (according to USP3,076,010 method)

[0021] (1) Add 24.4g of 37% formaldehyde aqueous solution into the reaction flask, and add 30.9g of diethanolamine at 20°C to 30°C under stirring.

[0022] (2) Add 41.4 g of diethyl phosphite at 20°C to 30°C. Since it is an exothermic reaction, keep the reaction temperature at 35°C under cooling, cool down to 30°C within about 40 minutes, continue stirring at room temperature for a period of time, and then heat to 50°C for 15 minutes.

[0023] (3) Cool the reactant, extract the reactant with 100ml ether, and separate the water layer.

[0024] (4) Concentrate the water layer by distillation under reduced pressure, and then collect the fraction at 50° C. / 1 mmHg by distillation under reduced pressure to obtain the product with a yield of 94.8%. The N,N-bis(2-hydroxyethyl)aminomethylphosphonic acid diethyl ester content in the gas phase analysis product was 88%.

Embodiment 3

[0026] The difference with embodiment 1 is:

[0027] Step (1) Add 40% formaldehyde aqueous solution to the reactor, keep the reaction temperature at 40° C., and react for 1.5 hours.

[0028] Step (2) Change the reaction device to vacuum distillation. At 60° C., the pressure is less than 0.095 MPa. Water is distilled off under reduced pressure, and then continue the vacuum distillation at 80° C. for 2 hours.

[0029] Step (3) Cool down to 50°C, add 1.3 parts of anhydrous solid acid catalyst. Then incubate at 40°C for 3 hours

[0030] A yellow transparent liquid product was obtained with a yield of 99%. The N,N-bis(2-hydroxyethyl)aminomethylphosphonic acid diethyl ester content in the gas phase analysis product was 94%.

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Abstract

N, N-bis(2-hydroxyethyl) aminomethylphosphonic diethylester is concerned with preparation of aminomethylphosphonic diester. It includes: (1) reaction of formaldehyde water solution with diethanol; (2) decompression distilling to produce 3 - (2 -hydroxyethyl) - 1,3, - oxaazapentane; (3) adding anhydrous solid acid catalysts and phosphonous acid diester; (4) filtrating and recovering the catalysts to get yellow transparency products with yields of above 98% and 94%-94% contents of N, N-bis(2-hydroxyethyl) aminomethylphosphonic diethylester. It is prepared simply, and highly yields with more effective content. The product is reactive fire-retardant for environmental protection, capably used in plastics, especially in foamed polyamine ester.

Description

technical field [0001] The invention relates to a method for preparing N, N-bis(2-hydroxyethyl) diethyl aminomethylphosphonate, which belongs to the field of diethyl aminomethylphosphonate preparation. Background of the invention [0002] N, N-bis(2-hydroxyethyl)aminomethylphosphonic acid diethyl ester (structural formula shown in I) is a non-halogen environment-friendly reactive flame retardant, mainly used for flame retardancy of plastics, especially suitable for For the preparation of polyurethane foam. U.S. Patent No. 3,076,010 discloses a detailed preparation method of this compound. The synthesis method is (1) addition reaction of diethanolamine and formaldehyde (37% aqueous solution) to generate an intermediate aqueous solution; (2) the intermediate aqueous solution and phosphorous acid Diethyl ester reaction; (3) extraction with ether; (4) underpressure distillation separation to obtain N, N-bis (2-hydroxyethyl) aminomethyl phosphonic acid diethyl ester, product yie...

Claims

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Application Information

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IPC IPC(8): C07F9/38
Inventor 刘治国欧育湘吴玉凯
Owner HENAN UNIVERSITY
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