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Method for preparing taurine from sodium hydroxyethyl sulfonate

A technology of sodium isethionate and taurine, which is applied in the fields of sulfonic acid preparation, sulfonate preparation, organic chemistry, etc., can solve the problems of harsh ammonolysis reaction conditions, high energy consumption in the reaction process, and high production cost. Achieve the effects of improving electrophilic properties, shortening reaction time, and mild reaction temperature and pressure conditions

Inactive Publication Date: 2019-03-29
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The key synthesis step of the ethylene oxide method is the reaction of sodium isethionate and liquid ammonia to prepare sodium taurine. In the initial research, since no catalyst was added, harsh conditions of high temperature of 200-280°C and high pressure of 14-21MPa were required. Reaction conditions, which have resulted in high energy consumption in the reaction process and higher production costs
[0006] Chinese patent CN105732440A discloses that in the ammonolysis reaction process containing mother liquor, alkali metal hydroxides, alkali metal carbonates (including acid carbonates), iron series / aluminum series metal salts, NiO / CeO can be added 2 , rare earth oxides or any combination thereof as a catalyst, the yield of sodium taurate can be increased to 90-95%, but the reaction still requires a high temperature of 255-265°C and a pressure of 19-20MPa, and the conditions are still relatively harsh
[0009] In summary, the ammonolysis reaction conditions of the current taurine preparation process are still relatively harsh, and the process conditions need to be improved to reduce energy consumption in the production process and reduce production costs

Method used

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  • Method for preparing taurine from sodium hydroxyethyl sulfonate
  • Method for preparing taurine from sodium hydroxyethyl sulfonate
  • Method for preparing taurine from sodium hydroxyethyl sulfonate

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Put 696g of sodium isethionate solution (15.0wt%) in a 1L high-pressure reactor, feed a certain amount of liquid ammonia to make the concentration of liquid ammonia reach 24.0wt%, then add 0.104g (0.1wt%) IL-1 Catalyst and 0.104g CuCl co-catalyst, the temperature of the reaction system was raised to 160° C., the system pressure was 9.8 MPa, and the reaction was carried out for 30 minutes. The yield of sodium taurate obtained by the ammonolysis reaction was 92.5%. After the reaction solution was flashed at 100°C to remove ammonia, it was evaporated and concentrated to increase the concentration of sodium taurine to 40wt%, and then a certain amount of concentrated sulfuric acid was added at 80°C to adjust the pH of the system to 7.8, and then cooled to 20°C Crystallization, the one-way yield of taurine after crystallization is 75.0%, and the mother liquor can be applied mechanically again to ammonolysis reaction, and the total yield of taurine after mechanical application ...

Embodiment 2

[0042]Place 740g of sodium isethionate solution (20.0wt%) in a 1L high-pressure reactor, feed a certain amount of liquid ammonia to make the concentration of liquid ammonia reach 21.0wt%, then add 0.296g (0.2wt%) IL-2 Catalyst and 0.148g CuCl co-catalyst, the reaction system was heated to 140° C., the system pressure was 7.2 MPa, and the reaction was carried out for 20 minutes. The yield of sodium taurate obtained in this step reaction was 89.0%. After the reaction solution was flashed at 100°C to remove ammonia, it was evaporated and concentrated to increase the concentration of sodium taurine to 38wt%, and then a certain amount of concentrated sulfuric acid was added at 60°C to adjust the pH of the system to 8.2, and then cooled to 30°C Crystallization, the one-way yield of taurine after crystallization is 70.0%, the mother liquor can be applied again to ammonolysis reaction, and the total yield of taurine is 90.9%.

Embodiment 3

[0044] 724g of sodium isethionate solution (18.0wt%) was placed in a 1L high-pressure reactor, and a certain amount of liquid ammonia was introduced to make the concentration of liquid ammonia reach 18.0wt%, and then 0.065g (0.05wt%) of IL-1 was added Catalyst and 0.046g CuCl co-catalyst, the reaction system was heated to 120° C., the system pressure was 5.1 MPa, and the reaction was carried out for 60 minutes. The yield of sodium taurate obtained in this step reaction was 95.0%. After the reaction solution was flashed at 100°C to remove ammonia, it was evaporated and concentrated to increase the concentration of sodium taurine to 35wt%, and then a certain amount of concentrated sulfuric acid was added at 90°C to adjust the pH of the system to 7, and then cooled to 20°C Crystallization, the one-way yield of taurine after crystallization is 73.2%, and the mother liquor can be applied to ammonolysis reaction again, and the total yield of taurine after application is 93.5%.

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Abstract

The invention provides a method for preparing taurine from sodium hydroxyethyl sulfonate. An ionic liquid homogeneous catalyst is adopted to catalyze an ammonolysis reaction of sodium hydroxyethyl sulfonate, and then steps of neutralization, crystallization separation and the like are carried out to obtain the finished taurine. Compared with a conventional alkaline catalyst, the ionic liquid homogeneous catalyst adopted in the process can significantly reduce the temperature and pressure of the ammonolysis reaction of the sodium hydroxyethyl sulfonate, so that the reaction time is shortened, and industrial production is facilitated.

Description

technical field [0001] The invention relates to a method for preparing taurine from sodium isethionate. Background technique [0002] Taurine, also known as taurocholic acid, taurobilin, and chemical name 2-aminoethanesulfonic acid, is an essential non-protein amino acid that exists in almost all organs of humans and mammals in free form. The role of taurine is different from that of other amino acids. It can promote the growth and development of the nervous system, protect the brain, improve memory, and improve optic nerve conduction and visual function. It can also protect the heart, prevent and treat cardiovascular and cerebrovascular diseases and other important diseases. Features. Taurine has high medicinal value and is an important nutrient. It is widely used in functional beverages, pet food, health food, feed, medicine and other fields. It can also be used as biochemical reagents and other organic synthesis intermediates. A fine chemical with wide application value...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/32C07C309/14
CPCC07C303/22C07C309/14
Inventor 桂振友郭斌蔺海政赵凯飞张静钟子太孔令晓梁静王文李晶李浩陈来中张永振
Owner WANHUA CHEM GRP CO LTD
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