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N-tris (hydroxymethyl) methyl-3-aminopropanesulfonic acid compound and preparation method thereof

A technology of trimethylolaminomethane and aminopropanesulfonic acid, which is applied in the field of N-trimethyl-3-aminopropanesulfonic acid compound and its preparation, can solve the problems of low yield, few synthesis processes and the like, and achieves high yield. The effect of high yield, easy availability of raw materials and few synthesis steps

Inactive Publication Date: 2010-09-29
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthetic technique of TAPS is less, and Mitteilung [Mitteilung; I Zeid, I.Ismail undB.Helferich.Synthese von N-substituierten Aminosulfonsauren.LeibigsAun.Chem.761.118 (1972)] only describes two raw materials 1,3-propanesulfonic acid Synthesis of TAPS with ester and trihydroxymethylaminomethane in n-butanol reaction solvent, the yield is 65%, but the yield is low, without other process conditions

Method used

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  • N-tris (hydroxymethyl) methyl-3-aminopropanesulfonic acid compound and preparation method thereof
  • N-tris (hydroxymethyl) methyl-3-aminopropanesulfonic acid compound and preparation method thereof
  • N-tris (hydroxymethyl) methyl-3-aminopropanesulfonic acid compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Put 24.22g (0.2mol) of trishydroxymethylaminomethane and 24.43g (0.2mol) of 1,3-propane sultone into a 500mL four-necked flask with a stirring paddle, a thermometer, and a condenser, and add About 200mL of 95% alcohol is used as a solvent, stirred and dissolved at a speed of 150 rpm, the reaction system is heated to boiling, and the ethanol is condensed and refluxed. After reacting for about 2 hours, cool to room temperature, and then put it in the refrigerator to cool to 0°C or below. After the product is fully crystallized, take it out and filter. The filter cake is the obtained crude product. The crude product was washed 2-3 times with absolute ethanol, put into an oven and dried at 80° C. for 24 hours to obtain the final product in the form of white powder. According to high-performance liquid phase analysis, its purity is 98.09%, its yield is 71.77%, and its melting point is 229.1-229.4°C.

Embodiment 2

[0021] Put 24.22g (0.2mol) of trishydroxymethylaminomethane and 24.43g (0.2mol) of 1,3-propane sultone into a 500mL four-necked flask with a stirring paddle, a thermometer, and a condenser, and add About 200mL of pure ethanol was used as a solvent, stirred and dissolved at a speed of 150 rpm, the reaction system was heated to boiling, and the ethanol was condensed and refluxed. After reacting for about 2 hours, cool to room temperature, and then put it in the refrigerator to cool to 0°C or below. After the product is fully crystallized, take it out and filter. The filter cake is the obtained crude product. The crude product was washed 2-3 times with absolute ethanol, put into an oven and dried at 75°C for 24 hours to obtain 36.26g of the final product in the form of white powder, with a yield of 74.61% and a melting point of 229.7-230.0°C.

Embodiment 3

[0023] Put 24.22g (0.2mol) of trishydroxymethylaminomethane and 24.43g (0.2mol) of 1,3-propane sultone into a 500mL four-necked flask with a stirring paddle, a thermometer, and a condenser, and add About 200mL of n-propanol was used as a solvent, stirred and dissolved at a speed of 150 rpm, the reaction system was heated to boiling, and the n-propanol was condensed and refluxed. After reacting for about 2 hours, cool to room temperature, and then put it in the refrigerator to cool to 0°C or below. After the product is fully crystallized, take it out and filter. The filter cake is the obtained crude product. The crude product was washed 2-3 times with absolute ethanol, put into an oven and dried at 80°C for 24 hours to obtain 36.40 g of a white powdery final product with a yield of 74.82% and a melting point of 229.5-229.9°C.

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Abstract

The invention relates to an N-tris (hydroxymethyl) methyl-3-aminopropanesulfonic acid compound and a preparation method thereof. The N-tris (hydroxymethyl) methyl-3-aminopropanesulfonic acid compound is prepared by the following steps of putting tris (hydroxymethyl) aminomethane and 1,3-propanesultone with the same molar ratio into a 500mL four-hole flask with a stirring paddle, a thermometer and a condensation pipe, adding 250-300mL of C1-C8 alcohol as a solvent, stirring and dissolving the mixture with a proper speed, heating a reaction system to boiling, and treating the alcohol by condensing reflux; reacting for 1-8h; putting a reaction product into a refrigerator, treating the product by cooling to 0 DEG C and filtering, wherein a filter cake is an obtained crude product; obtaining a white powder final product by washing the crude product by absolute ethyl alcohol for 2-3 times, and obtaining the N-tris (hydroxymethyl) methyl-3-aminopropanesulfonic acid compound by putting the final product into an oven and drying the product for 20-28h under the temperature of 70-120 DEG C. The invention has the advantages of little synthesis steps and simple operation and has the product yield of 75 percent and the product purity no less than 99 percent.

Description

【Technical field】 [0001] The N-tris(hydroxymethyl)methyl-3-aminopropanesulfonic acid involved in the present invention is one of a series of products synthesized from trimethylolaminomethane as a raw material, and is composed of 1,3-propanesulfonic acid The ester is synthesized by heating ring-opening and trimethylolmethane in a C1-C8 alcohol solvent, specifically, it is a kind of N-tris(hydroxymethyl)methyl-3-aminopropanesulfonic acid compound and its preparation method . 【Background technique】 [0002] Tris(hydroxymethyl)aminomethane and some series compounds synthesized as raw materials such as N-tris(hydroxymethyl)methyl-3-aminopropanesulfonic acid (TAPS) synthesized by the present invention are becoming more and more It is more and more widely used in biochemistry, chemistry and medicine. Among them, N-tris(hydroxymethyl)methyl-3-aminopropanesulfonic acid can be used as the carrier of biological enzymes and proteins and as the chelating agent of certain metal ions suc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/14C07C303/02
Inventor 许振良夏小忠陈桂娥
Owner EAST CHINA UNIV OF SCI & TECH
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