CN111233717A - Method for efficiently separating useful components from taurine crystallization mother liquor - Google Patents
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- CN111233717A CN111233717A CN202010080277.5A CN202010080277A CN111233717A CN 111233717 A CN111233717 A CN 111233717A CN 202010080277 A CN202010080277 A CN 202010080277A CN 111233717 A CN111233717 A CN 111233717A
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- C07C303/44—Separation; Purification
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Abstract
A method for efficiently separating useful components from taurine crystallization mother liquor is characterized in that the taurine crystallization mother liquor is used as a raw material, sulfate is removed by a barium chloride precipitation method, then effective components are converted into taurine and isethionic acid by hydrochloric acid acidification, the taurine and isethionic acid are further esterified by ethanol to generate an esterified product, the esterified product is transferred to an oil phase, after the oil phase is separated, taurine and isethionic acid are obtained by hydrolysis, finally, the isethionic acid and taurine are sequentially separated by evaporative crystallization and cooling crystallization, and the isethionic acid is subjected to neutralization reaction by sodium hydroxide to obtain sodium isethionate; the method can effectively recover useful components taurine and sodium isethionate in the taurine crystallization mother liquor, and can obviously reduce the environmental pollution possibly caused by the discharge of the taurine production waste liquid; has the advantages of low production cost, high recovery rate and easy industrial amplification.
Description
Technical Field
The invention relates to the technical field of chemical separation, in particular to a method for efficiently separating useful components from taurine crystallization mother liquor.
Background
Taurine has the chemical name of 2-aminoethyl sulfonic acid and the molecular formula of HO3S-CH2-CH2-NH2The taurine is white crystalline powder with melting point of 328 ℃, has no toxicity, no odor and slight taste, is an active substance for regulating normal physiological activities of organisms, has the biological functions of diminishing inflammation, relieving pain, maintaining osmotic pressure balance of the organisms, regulating cell calcium balance, regulating lipid digestion and absorption, increasing heart contractility, improving organism immunocompetence and the like, and can be widely used for medicines, fluorescent whitening agents, food additives, biochemical reagents, wetting agents, pH buffering agents and the like.
In industrial production, the preparation of taurine by an ethylene oxide method comprises three steps of reactions: the first step is the addition reaction of ethylene oxide and sodium sulfite to produce sodium isethionate, but also by-products ethylene glycol and polyethylene glycol; the second step is that the sodium isethionate is subjected to ammoniation reaction to generate sodium aminoethyl sulfonate, the reaction also generates by-product ammonia isethionate, and in addition, a part of sodium isethionate is not completely reacted; and thirdly, carrying out acidification reaction on the sodium aminoethyl sulfonate and sulfuric acid to generate aminoethyl sulfonic acid, namely taurine, wherein a byproduct sodium sulfate is generated.
After the three steps of reactions are finished, evaporating, crystallizing and centrifugally separating to obtain a taurine finished product, wherein the crystallization mother liquor comprises the following components: the taurine comprises 13% of taurine, 50% of sodium isethionate, 4% of glycol and polyethylene glycol, 2% of sodium sulfate and a very small amount of ammonia isethionate, wherein the useful components are taurine and sodium isethionate, the taurine can be sold as a finished product, the sodium isethionate is a raw material for producing the taurine by ammoniation, and a crystallization mother liquor in industrial production is difficult to recycle due to the fact that the crystallization mother liquor contains more impurity components, so that the crystallization mother liquor is discharged as a waste liquor, not only wastes resources, but also pollutes the environment.
The above components of taurine are all easy to dissolve in water, and the conventional methods of chemical precipitation, evaporative crystallization, cooling crystallization, membrane separation, ion exchange and the like are difficult to separate the effective components from the taurine crystallization mother liquor, so how to effectively separate the useful components of taurine and sodium hydroxyethyl sulfonate in the taurine crystallization mother liquor becomes a problem which needs to be solved urgently for industrially preparing taurine.
Disclosure of Invention
The invention aims to solve the technical problem of providing a method for efficiently separating useful components from taurine crystallization mother liquor, and the method finally separates taurine and sodium isethionate by the processes of precipitation, acidification, esterification, hydrolysis, evaporative crystallization, cooling crystallization and the like.
The technical problem solved by the invention is realized by adopting the following technical scheme:
a method for efficiently separating useful components from taurine crystallization mother liquor comprises the following specific steps:
(1) and (3) precipitation: adding barium chloride for removing sulfate into a proper amount of taurine crystallization mother liquor, stirring to fully separate out barium sulfate, and filtering and separating barium sulfate to obtain primary filtrate;
(2) acidifying: adding concentrated hydrochloric acid into the primary filtrate, heating to 80 ℃, stirring to promote the sodium isethionate to be converted into isethionic acid, simultaneously precipitating sodium chloride, and filtering to separate the sodium chloride to obtain secondary filtrate;
(3) esterification: adding appropriate amount of ethanol into the secondary filtrate, continuously stirring at 90 deg.C for reaction, layering the solution to obtain water layer and oil layer, wherein the water layer contains ethanol, ethylene glycol, polyethylene glycol and small amount of sodium chloride and sodium sulfate, and separating the water layer to obtain oil layer containing esterification products including taurine ester and hydroxyethyl sulfonate;
(4) hydrolysis: adding a proper amount of water into the oil layer generated in the step (3), continuously stirring and reacting at the temperature of 80 ℃ to obtain a hydrolysate, and adding water and stirring to promote the taurate and the isethionate to be converted into taurine and isethionic acid respectively;
(5) evaporation and crystallization: evaporating and crystallizing the hydrolysate obtained in the step (4) at the temperature of 95 ℃ to separate out the isethionic acid, and filtering and separating the isethionic acid to obtain a third-stage filtrate;
(6) cooling and crystallizing: cooling and crystallizing the third-stage filtrate obtained in the step (5) at the temperature of 5 ℃ until the taurine is fully precipitated, and filtering and separating a solid-phase product to obtain the taurine;
(7) neutralization with hydroxyethyl sulfonic acid: and (3) dissolving the isethionic acid precipitated in the step (5), adding a sodium hydroxide solution, adjusting the pH value to be neutral, and evaporating and crystallizing at the temperature of 95 ℃ to obtain the sodium isethionate solid.
In the present invention, in the step (1), the stirring time is 30 min.
In the present invention, in the step (2), the stirring time is 30 min.
In the invention, in the step (3), 60-100 mL of ethanol is added into the secondary filtrate.
In the present invention, in the step (3), the reaction time is further stirred at a temperature of 90 ℃ for 30 min.
In the invention, in the step (4), 30-50 mL of water is added into the oil layer.
In the present invention, in the step (4), the reaction time is 1h under the condition of continuing stirring at the temperature of 80 ℃.
In the present invention, in the step (5), the time for evaporative crystallization at a temperature of 95 ℃ is 1 hour.
In the present invention, in the step (6), the cooling crystallization time at the temperature of 5 ℃ is 2 h.
In the present invention, in the step (7), the concentration of the sodium hydroxide solution is 1 mol/L.
Has the advantages that:
(1) the method takes the taurine crystallization mother liquor as a raw material, and finally separates useful components taurine and sodium hydroxyethyl sulfonate from the taurine crystallization mother liquor through the processes of precipitation, acidification, esterification, hydrolysis, evaporative crystallization, cooling crystallization and the like, and the method not only can effectively recover the useful components taurine and sodium hydroxyethyl sulfonate in the taurine crystallization mother liquor, but also can obviously reduce the environmental pollution possibly brought by the discharge of taurine production waste liquid, and has the advantages of low production cost, high recovery rate and easy industrial amplification;
(2) the invention promotes taurine and isethionic acid to generate an esterified product by utilizing ethanol esterification, and transfers the esterified product to an oil phase, thereby realizing the high-efficiency separation of useful components and impurity components (ethylene glycol, polyethylene glycol and sodium sulfate) in the taurine crystallization mother liquor and effectively solving the problem of difficult separation in the conventional method.
Drawings
Fig. 1 is a schematic flow chart of the present embodiment.
Detailed Description
In order to make the technical means, the creation characteristics, the achievement purposes and the effects of the invention easy to be understood and clear, the invention is further described by combining the specific embodiments.
Example 1
A method for efficiently separating useful components from taurine crystallization mother liquor comprises the following specific steps:
(1) and (3) precipitation: adding about 3g of barium chloride into 100mL of taurine crystallization mother liquor, stirring for 30min to fully separate out barium sulfate, and filtering and separating barium sulfate to obtain first-stage filtrate;
(2) acidifying: adding 30mL of concentrated hydrochloric acid into the primary filtrate, heating to 80 ℃, stirring for 30min to promote the transformation of the sodium isethionate into isethionic acid while precipitating sodium chloride, and filtering to separate the sodium chloride to obtain secondary filtrate;
(3) esterification: adding 60mL of ethanol into the secondary filtrate, continuously stirring and reacting at 90 ℃ for 30min, layering the solution, separating the water layer containing ethanol, ethylene glycol, polyethylene glycol and a small amount of sodium chloride and sodium sulfate, and separating the water layer to obtain an oil layer containing esterification products including taurine ester and hydroxyethyl sulfonate;
(4) hydrolysis: adding 30mL of water into the oil layer generated in the step (3), continuously stirring and reacting for 1h at the temperature of 80 ℃ to obtain a hydrolysate, and adding water and stirring to promote taurate and isethionate to be converted into taurine and isethionic acid respectively;
(5) evaporation and crystallization: evaporating and crystallizing the hydrolysate obtained in the step (4) for 1h at the temperature of 95 ℃, separating out the isethionic acid, and filtering and separating the isethionic acid to obtain a third-stage filtrate;
(6) cooling and crystallizing: cooling and crystallizing the third-stage filtrate obtained in the step (5) at the temperature of 5 ℃ for 2 hours until the taurine is fully precipitated, and filtering and separating a solid-phase product to obtain the taurine;
(7) neutralization with hydroxyethyl sulfonic acid: and (3) dissolving the isethionic acid precipitated in the step (5), adding 1mol/L sodium hydroxide solution, adjusting the pH value to be neutral, and evaporating and crystallizing at the temperature of 95 ℃ to obtain the solid of the isethionic acid sodium.
Taking 100mL of taurine crystallization mother liquor as a raw material, and a separation experiment result shows that the purity of taurine is 98% and the yield is 62%; the purity of the hydroxyethyl sodium sulfonate is 95 percent, and the yield is 55 percent.
Example 2
A method for efficiently separating useful components from taurine crystallization mother liquor comprises the following specific steps:
(1) and (3) precipitation: adding about 3g of barium chloride into 100mL of taurine crystallization mother liquor, stirring for 30min to fully separate out barium sulfate, and filtering and separating barium sulfate to obtain first-stage filtrate;
(2) acidifying: adding 30mL of concentrated hydrochloric acid into the primary filtrate, heating to 80 ℃, stirring for 30min to promote the transformation of the sodium isethionate into isethionic acid while precipitating sodium chloride, and filtering to separate the sodium chloride to obtain secondary filtrate;
(3) esterification: adding 80mL of ethanol into the secondary filtrate, continuously stirring and reacting at 90 ℃ for 30min, layering the solution, wherein the water layer contains ethanol, ethylene glycol, polyethylene glycol and a small amount of sodium chloride and sodium sulfate, and after separating the water layer, the oil layer contains esterification products including taurine ester and hydroxyethyl sulfonate;
(4) hydrolysis: adding 40mL of water into the oil layer generated in the step (3), continuously stirring and reacting for 1h at the temperature of 80 ℃ to obtain a hydrolysate, and adding water and stirring to promote the taurate and the isethionate to be converted into taurine and isethionic acid respectively;
(5) evaporation and crystallization: evaporating and crystallizing the hydrolysate obtained in the step (4) for 1h at the temperature of 95 ℃, separating out the isethionic acid, and filtering and separating the isethionic acid to obtain a third-stage filtrate;
(6) cooling and crystallizing: cooling and crystallizing the third-stage filtrate obtained in the step (5) at the temperature of 5 ℃ for 2 hours until the taurine is fully precipitated, and filtering and separating a solid-phase product to obtain the taurine;
(7) neutralization with hydroxyethyl sulfonic acid: and (3) dissolving the isethionic acid precipitated in the step (5), adding 1mol/L sodium hydroxide solution, adjusting the pH value to be neutral, and evaporating and crystallizing at the temperature of 95 ℃ to obtain the solid of the isethionic acid sodium.
Taking 100mL of taurine crystallization mother liquor as a raw material, and a separation experiment result shows that the purity of taurine is 98% and the yield is 81%; the purity of the hydroxyethyl sodium sulfonate is 95 percent, and the yield is 68 percent.
Example 3
A method for efficiently separating useful components from taurine crystallization mother liquor comprises the following specific steps:
(1) and (3) precipitation: adding about 3g of barium chloride into 100mL of taurine crystallization mother liquor, stirring for 30min to fully separate out barium sulfate, and filtering and separating barium sulfate to obtain first-stage filtrate;
(2) acidifying: adding 30mL of concentrated hydrochloric acid into the primary filtrate, heating to 80 ℃, stirring for 30min to promote the transformation of the sodium isethionate into isethionic acid while precipitating sodium chloride, and filtering to separate the sodium chloride to obtain secondary filtrate;
(3) esterification: adding 100mL of ethanol into the secondary filtrate, continuously stirring and reacting at 90 ℃ for 30min, layering the solution, separating the water layer containing ethanol, ethylene glycol, polyethylene glycol and a small amount of sodium chloride and sodium sulfate, and separating the water layer to obtain an oil layer containing esterification products including taurine ester and hydroxyethyl sulfonate;
(4) hydrolysis: adding 50mL of water into the oil layer generated in the step (3), continuously stirring and reacting for 1h at the temperature of 80 ℃ to obtain a hydrolysate, and adding water and stirring to promote the taurate and the isethionate to be converted into taurine and isethionic acid respectively;
(5) evaporation and crystallization: evaporating and crystallizing the hydrolysate obtained in the step (4) for 1h at the temperature of 95 ℃, separating out the isethionic acid, and filtering and separating the isethionic acid to obtain a third-stage filtrate;
(6) cooling and crystallizing: cooling and crystallizing the third-stage filtrate obtained in the step (5) at the temperature of 5 ℃ for 2 hours until the taurine is fully precipitated, and filtering and separating a solid-phase product to obtain the taurine;
(7) neutralization with hydroxyethyl sulfonic acid: and (3) dissolving the isethionic acid precipitated in the step (5), adding 1mol/L sodium hydroxide solution, adjusting the pH value to be neutral, and evaporating and crystallizing at the temperature of 95 ℃ to obtain the solid of the isethionic acid sodium.
Taking 100mL of taurine crystallization mother liquor as a raw material, and a separation experiment result shows that the purity of taurine is 99 percent, and the yield is 90 percent; the purity of the hydroxyethyl sodium sulfonate is 97 percent, and the yield is 82 percent.
In the above embodiment, the taurine crystallization mother liquor is a taurine production waste liquor, and its main components include: taurine, sodium taurate, sodium isethionate, ethylene glycol, polyethylene glycol and sodium sulfate.
As a result of experiments for separating the useful components prepared in examples 1 to 3, example 3 (performed by adding 100mL of ethanol in the esterification step and 50mL of water in the hydrolysis step) showed the best separation effect, in which case taurine was 99% pure and 90% yield; the purity of the sodium isethionate is 97 percent, the yield is 82 percent, and the esterification products are increased along with the increase of the addition of ethanol in the esterification step, so that the addition of water in the hydrolysis step is correspondingly increased, and the yield and purity of the taurine and the sodium isethionate are also improved; however, the use amounts of ethanol and water are further increased, the effect of improving the yield and purity of taurine and sodium isethionate is not obvious, and the subsequent separation load and the production cost are increased.
The foregoing shows and describes the general principles and broad features of the present invention and advantages thereof. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (10)
1. A method for efficiently separating useful components from taurine crystallization mother liquor is characterized by comprising the following specific steps:
(1) and (3) precipitation: adding barium chloride for removing sulfate into a proper amount of taurine crystallization mother liquor, stirring to fully separate out barium sulfate, and filtering and separating barium sulfate to obtain primary filtrate;
(2) acidifying: adding concentrated hydrochloric acid into the primary filtrate, heating to 80 ℃, stirring to promote the sodium isethionate to be converted into isethionic acid, simultaneously precipitating sodium chloride, and filtering to separate the sodium chloride to obtain secondary filtrate;
(3) esterification: adding appropriate amount of ethanol into the secondary filtrate, continuously stirring at 90 deg.C for reaction, layering the solution to obtain water layer and oil layer, wherein the water layer contains ethanol, ethylene glycol, polyethylene glycol and small amount of sodium chloride and sodium sulfate, and separating the water layer to obtain oil layer containing esterification products including taurine ester and hydroxyethyl sulfonate;
(4) hydrolysis: adding a proper amount of water into the oil layer generated in the step (3), continuously stirring and reacting at the temperature of 80 ℃ to obtain a hydrolysate, and adding water and stirring to promote the taurate and the isethionate to be converted into taurine and isethionic acid respectively;
(5) evaporation and crystallization: evaporating and crystallizing the hydrolysate obtained in the step (4) at the temperature of 95 ℃ to separate out the isethionic acid, and filtering and separating the isethionic acid to obtain a third-stage filtrate;
(6) cooling and crystallizing: cooling and crystallizing the third-stage filtrate obtained in the step (5) at the temperature of 5 ℃ until the taurine is fully precipitated, and filtering and separating a solid-phase product to obtain the taurine;
(7) neutralization with hydroxyethyl sulfonic acid: and (3) dissolving the isethionic acid precipitated in the step (5), adding a sodium hydroxide solution, adjusting the pH value to be neutral, and evaporating and crystallizing at the temperature of 95 ℃ to obtain the sodium isethionate solid.
2. The method for efficiently separating useful components from taurine crystallization mother liquor according to claim 1, wherein the stirring time in step (1) is 30 min.
3. The method for efficiently separating useful components from taurine crystallization mother liquor according to claim 1, wherein in the step (2), the stirring time is 30 min.
4. The method for efficiently separating useful components from taurine crystallization mother liquor according to claim 1, wherein ethanol is added to the secondary filtrate in the step (3) in an amount of 60 to 100 mL.
5. The method for efficiently separating useful components from taurine crystallization mother liquor according to claim 1, wherein in the step (3), the reaction time is 30min under the condition of continuous stirring at 90 ℃.
6. The method for efficiently separating useful components from taurine crystallization mother liquor according to claim 1, wherein in the step (4), 30 to 50mL of water is added to the oil layer.
7. The method for efficiently separating useful components from taurine crystallization mother liquor according to claim 1, wherein in the step (4), the reaction time is 1h under the condition of continuous stirring at the temperature of 80 ℃.
8. The method for efficiently separating useful components from taurine crystallization mother liquor according to claim 1, wherein in the step (5), the evaporation crystallization time at 95 ℃ is 1 h.
9. The method for efficiently separating useful components from taurine crystallization mother liquor according to claim 1, wherein in the step (6), the cooling crystallization time is 2 hours at a temperature of 5 ℃.
10. The method for efficiently separating useful components from a taurine crystallization mother liquor according to claim 1, wherein the amount of ethanol added in the esterification step of step (3) is 100mL and the amount of water added in the hydrolysis step of step (4) is 50mL, when the separation effect is optimal.
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| EP4201921A1 (en) | 2021-12-24 | 2023-06-28 | Qiangjiang Yongan Pharmaceutical Co., Ltd. | Method for recycling taurine mother liquor |
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| US11858883B2 (en) | 2021-12-24 | 2024-01-02 | QIANJIANG Yongan Phamaceutical CO., LTD. | Method for recycling taurine mother liquor |
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