CN102633689A - Method for preparing taurine by adopting sulfonation of ammonium sulfite - Google Patents

Method for preparing taurine by adopting sulfonation of ammonium sulfite Download PDF

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CN102633689A
CN102633689A CN2012101005840A CN201210100584A CN102633689A CN 102633689 A CN102633689 A CN 102633689A CN 2012101005840 A CN2012101005840 A CN 2012101005840A CN 201210100584 A CN201210100584 A CN 201210100584A CN 102633689 A CN102633689 A CN 102633689A
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taurine
reaction
sulfonation
ammonium sulphite
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周彩荣
王海峰
詹自力
蒋登高
徐敏强
韩雪巍
黄明星
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Zhengzhou University
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Abstract

The invention discloses a method for preparing taurine by adopting sulfonation of ammonium sulfite. The method comprises the steps of: firstly carrying out esterification reaction to synthetize an intermediate 2-aminoethanol sulfate by taking concentrated sulfuric acid and ethanolamine as raw materials; carrying out sulfonation reaction to prepare taurine by taking ammonium sulfite and 2-aminoethyl sulfate as the raw materials, wherein ammonia is introduced to protect before the reaction, the temperature of the reaction solution is reduced after the sulfonation reaction is finished, and the conversion ratio of 2-aminoethyl sulfate is analyzed by adopting a sodium thiosulfate inverse titration method; cooling the reaction solution to room temperature, adding calcium hydroxide, heating, agitating and filtering to remove calcium sulfate, removing ammonia in mother liquor and repeatedly utilizing the mother liquor; then purifying the taurine by a cooling and crystallizing method to obtain crystal, carrying out suction filtration and baking the obtained crystal, and analyzing the taurine crystal by a thermal analysis method. The method disclosed by the invention is an integrated preparation method of combining the synthesis and separation of the taurine. The method is the preparation method of the taurine with simple operating process and mild reaction condition, wherein the primary conversion rate of 2-aminoethyl sulfate can be up to 79% and the desalination efficiency is 99.12%.

Description

Adopt the ammonium sulphite sulfonation to prepare the method for taurine
Technical field
The present invention relates to a kind of compound method of taurine, particularly relate to a kind of method that adopts the ammonium sulphite sulfonation to prepare taurine.
Background technology
Taurine is a kind of non-protein amino acid of sulfur-bearing, also is a kind of β-sulphur amino acid that it is essential that human body grows, and it is synthetic not participate in the body albumen, extensively is present in the animal body in each interstitial fluid and intracellular fluid with unbound state.The taurine range of application is wider, can be used for fields such as medicine, foodstuff additive, washing composition, white dyes, pH buffer reagent, and its application market prospect is very wide.
At present, according to the difference of synthesis material, the preparation method of taurine mainly contains: kinds more than ten such as thanomin sulphating method, thanomin chlorination, hydroxyl ethanol method, 2-monoethanolamine method, ethyleneimine method, ethionic anhydride method.At present, domestic and international most manufacturers all adopt girbotol process to produce taurine, and this method raw material is easy to get, and synthesis technique is simple, and facility investment is few.With the thanomin is the raw material synthesized taurine, is divided into esterification process and chlorination and ethyleneimine method again by synthetic route.
1, esterification process:
The domestic production taurine mainly adopts this method.This method is to be raw material with thanomin, sulfuric acid, S-WAT, and at first the vitriol oil and thanomin carry out esterification, synthesize midbody 2-monoethanolamine sulfuric ester, and midbody 2-monoethanolamine sulfuric ester carries out the sulfonation reaction synthesized taurine with S-WAT again.Reaction equation is following:
Figure 924834DEST_PATH_IMAGE002
In above-mentioned esterification reaction process, reaction is difficult for carrying out influencing the transformation efficiency of thanomin fully, and the method for taking has: heating promotes the reaction dehydration more than 120 ℃; Add an amount of vitriol oil, make dewatering agent; Add and be with aqua water to be steamed with the form of constant boiling mixture; Methods such as decompression dehydration can improve the esterification rate.But intermediate product 2-monoethanolamine sulfuric ester is very hard, needs to pulverize before the entering subsequent processing, and required labour intensity is big; Sulfonation reaction needs the reflux time long, and energy consumption is big, and 2-monoethanolamine sulfuric ester facile hydrolysis; The reaction product taurine is difficult to separate with inorganic salt.The brave grade in Japan person skilled Yamamoto improved to the problem that exists in this reaction, feeds ammonia and adds an amount of sulfuric ester, suppresses hydrolysis reaction, and adopts electrodialytic desalting, can improve the taurine yield and reach more than 90%.It is to feed nitrogen that domestic relevant scientific and technical personnel carry out improved method to existing problems, and the synthesis yield that can improve taurine reaches 85%.But China is adopting the yield of this explained hereafter taurine to be merely about 53% in the industry at present, and cost is high, compares with external production, and also there is a big difference.
2, chlorination:
This method is to be raw material with thanomin, hydrochloric acid, S-WAT, and reaction process divides chlorination, two steps of sulfonation to carry out, through 2-chloroethyl amine hydrochloride midbody synthesized taurine.Reaction equation is following:
Figure 664382DEST_PATH_IMAGE003
This method raw material is easy to get, but the control of reaction conditions difficulty or ease, yield is very low, is approximately 48%.In chlorination, also there are the ethanolamine hydrochloric salt of employing and sulfur oxychloride to make solvent and generate chloroethylamine hydrochloride, and then generate taurine with the S-WAT reaction in 60 ℃ of reactions with toluene.1989, the people such as D.Pauluth of Germany were in the carboxylic acid of equivalent, and sulfur oxychloride and ethanolamine hydrochloric salt are to react 7h down in 60 ℃ by stoichiometry, obtain α-chloroethylamine hydrochloride, and productive rate reaches 99.1% near theoretical value.Because by product is a gas and anhydrous, product purity is higher.Another German Patent adopts 350mL 37% hydrochloric acid and the 244g thanomin reaction that is dissolved in the 800mL toluene, and 110 ℃ of azeotropic removal of water parts are cooled to 50 ℃, add 3.2g NH 4The Cl catalyzer then, drips the 314mL sulfur oxychloride and generates 2-ammonia ethylamine hydrochloride.Though this technology yield is higher, cost is high, so neither the ideal production technique.
In the chlorination, the production technique of tool development prospect is dried hydrogen chloride.Its raw material is easy to get, cost is low, yield can be up to more than 80 %.Dried hydrogen chloride is to adopt Monoethanolamine MEA BASF and exsiccant hcl reaction to generate chloroethylamine hydrochloride, generates taurine with the S-WAT reaction then.
3, ethyleneimine method:
The beginning of the eighties, the human thanomins such as KDOison of U.S. Union Carbide Corp through gas phase catalysis dehydration condensation one-step synthesis ethyleneimine, processed taurine with sulfuric acid open loop addition then.Reaction equation is following:
Figure 776564DEST_PATH_IMAGE004
Japan catalyst chemical company makes broad research to multiple catalyzer, uses the nitrogen atomization thanomin of volume ratio as 98:3, is being filled with Cs 0.9Ba 0.1P 0.8Intramolecular cyclization takes place in the reaction tower of catalyzer generate ethyleneimine; Again direct after its evaporation and ammonium bisulfite reaction are made taurine, productive rate is 84%, and the characteristics of this technology are less investments; Cost is low; Do not need separating by-products, technology is advanced than several methods in front, drops into suitability for industrialized production in the 1980's Mos abroad.
Although producing the yield of taurine, the ethyleneimine method can reach more than 80 %, because the hypertoxicity of ethyleneimine and boiling point are low volatile, and with the viewpoint of Sustainable development and green chemical industry, obviously neither optimal process routes.
Summary of the invention
The technical problem that the present invention will solve provides a kind of method that adopts the ammonium sulphite sulfonation to prepare taurine.Technical scheme of the present invention is the synthetic a kind of integrated artistic that gets up with its separation and combination with taurine.Technical scheme of the present invention is the compound method of the taurine that a kind of operating procedure is simple, reaction conditions is gentle, and wherein the transformation efficiency of 2-monoethanolamine sulfuric ester reaches 79%.And adopted a kind of method of new analysis taurine, i.e. heat analysis method.
In order to address the above problem, the technical scheme that the present invention adopts is:
The present invention provides a kind of method that adopts the ammonium sulphite sulfonation to prepare taurine, said method comprising the steps of:
A, esterification: at first adopting ordinary method is that raw material carries out esterification with the vitriol oil and thanomin, the synthetic midbody 2-monoethanolamine sulfuric ester that obtains;
B, sulfonation reaction: preceding 4~6min feeds ammonia in reaction vessel in the reaction beginning, and ammonia flow is 10~20mLmin -1At first add step a synthetic midbody 2-monoethanolamine sulfuric ester, add ammonium sulphite then, said ammonium sulphite and 2-monoethanolamine sulfuric ester between the two the mol ratio of add-on be 1~5:1; Begin to carry out sulfonation reaction; Control sulfonation reaction temperature is 35~110 ℃, and the reaction times is 5~20h, and the feed way of raw material ammonium sulphite is 1~10 time; After sulfonation reaction finishes; With the reaction soln cooling,, measure the yield that calculates the gained taurine with Sulfothiorine residual titration method when gained reaction soln temperature is reduced to below 65 ℃;
C, step b gained reaction soln is reduced to room temperature, add Ca (OH) then therein 2Solution, Ca (OH) 2The add-on of solution is that 1~5 mole of ammonium sulphite adding concentration is 0.1molL -1Ca (OH) 2Solution 0.1~0.6L adds Ca (OH) 2Obtain mother liquor behind the solution, heat mother liquid obtainedly, remove the ammonia in the mother liquor, and collect the ammonia of removing and utilize again to 45~80 ℃; Reduce the mother liquor temperature then, carry out suction filtration after reducing to room temperature, obtain precipitate C aSO when mother liquid obtained 4, when sulphate content is lower than 1% in the gained filtrating after measuring suction filtration, stop to add Ca (OH) 2Solution;
D, adopt the crystallisation by cooling method that contained taurine is wherein purified step c gained filtrating, at first adopting phosphate buffered saline buffer to regulate pH value of filtrate is 5~7, and progressively cooling; Rate of temperature fall is 0.05~4 ℃/min; Reduce to and carry out crystallization when Tc is 5~30 ℃, crystallization time is 1~15h, and the gained crystal is carried out suction filtration; Dry then to constant weight, obtain product taurine crystal;
E, the product taurine crystal by adopting heat analysis method that steps d is obtained are analyzed.
The method for preparing taurine according to above-mentioned employing ammonium sulphite sulfonation; Preceding 4~the 6min of reaction beginning feeds ammonia among the step b in reaction vessel, and system is protected, and makes system be alkalescence; Suppress the hydrolysis of 2-monoethanolamine sulfuric ester, and in step c, recycle and reuse.
Prepare the method for taurine according to above-mentioned employing ammonium sulphite sulfonation, among the step b ammonium sulphite and 2-monoethanolamine sulfuric ester between the two the mol ratio of add-on be 1.3~1.8:1.
Prepare the method for taurine according to above-mentioned employing ammonium sulphite sulfonation, control sulfonation reaction temperature is 65~105 ℃ among the step b, and the reaction times is 8~12h.
Prepare the method for taurine according to above-mentioned employing ammonium sulphite sulfonation, the feed way of the ammonium sulphite of raw material described in the step b is 1~4 time.
Prepare the method for taurine according to above-mentioned employing ammonium sulphite sulfonation, rate of temperature fall described in the steps d is 0.5~3 ℃/min; The stir speed (S.S.) of magnetic stirring apparatus is 100~800r/min in cooling, the crystallisation process.
Prepare the method for taurine, the stir speed (S.S.) 400~600r/min of magnetic stirring apparatus in said cooling, the crystallisation process according to above-mentioned employing ammonium sulphite sulfonation.
Prepare the method for taurine according to above-mentioned employing ammonium sulphite sulfonation, reduce in the steps d and carry out crystallization when Tc is 14~25 ℃, crystallization time is 3~12h.
Prepare the method for taurine according to above-mentioned employing ammonium sulphite sulfonation, dry described in the steps d to constant weight, its bake out temperature is 80~100 ℃.
After the synthetic reaction of taurine finishes among the technical scheme steps b of the present invention, mainly contain taurine, ammonium sulfate, ammonium sulphite and 2-monoethanolamine sulfuric ester in the reaction soln.Ammonium sulphite is oxidation very easily, makes its abundant ingress of air through stirring, and the reaction of heating promotes oxidn is carried out, so that its complete oxidation is an ammonium sulfate, in reaction solution, adds Ca (OH) 2Saturated solution is removed ammonium sulfate wherein, and the desalination rate reaches more than 99%.Whole process byproducts has ammonia, calcium sulfate.The by product ammonia recycles as the sulfonation reaction shielding gas, and technology of the present invention relates to following reaction, and reaction equation is following:
Figure 872DEST_PATH_IMAGE005
Figure 969888DEST_PATH_IMAGE007
Positive beneficial effect of the present invention:
1, technical scheme of the present invention is a kind of complete preparation method that the synthetic and separation and combination of taurine is got up.
2, technical scheme of the present invention is the preparation method of the taurine that a kind of operating procedure is simple, reaction conditions is gentle, and wherein the transformation efficiency of 2-monoethanolamine sulfuric ester can reach 79%.
3, through technical scheme of the present invention, the method that has obtained a kind of new analysis taurine is a heat analysis method.Wherein the atlas analysis of products obtained therefrom is seen accompanying drawing 1-4.Accompanying drawing 1 is the hot analysis of spectra of product of the present invention, can be known by the atlas analysis of Fig. 1, can prepare the product taurine through technical scheme of the present invention.
4, with the ammonium sulphite be the technology of sulphonating agent synthesized taurine, its ammonium sulphite can directly be taken from the sub product of urea production process, has increased industrial chain.
5, adopt and to saltout-method that the separation of crystallization-recrystallization is purified, can obtain that the needed ammonia gas that contains is used to recycle in the reaction process.This operational path is a friendly process, non-environmental-pollution, and cost is low, and later separation is easier to, and is easy to promotion and implementation.
Four, description of drawings:
The thermogram of Fig. 1 product taurine of the present invention;
The thermogram of Fig. 2 gained midbody of the present invention 2-monoethanolamine sulfuric ester;
The thermogram (content of taurine 90%) of Fig. 3 product taurine of the present invention and midbody 2-monoethanolamine sulfate mixture;
The thermogram (content of taurine 95%) of Fig. 4 product taurine of the present invention and midbody 2-monoethanolamine sulfate mixture.
Accompanying drawing 1-4 explanation: can find out only an endotherm(ic)peak is arranged about 600K in the thermogram of the pure article of taurine, and be accompanied by weightlessness by collection of illustrative plates in accompanying drawing 1, the accompanying drawing 2; About 500K, there is endotherm(ic)peak in the thermogram of the pure article of 2-monoethanolamine sulfuric ester, do not have weightlessness, endotherm(ic)peak is arranged about 600K and follow weightlessness.Collection of illustrative plates can be found out in accompanying drawing 3 and the accompanying drawing 4; The thermogram of taurine and 2-monoethanolamine sulfate mixture (content of taurine 90%) all has tangible endotherm(ic)peak about 500K He under these two temperature of the 600K left and right sides; The thermogram of taurine and 2-monoethanolamine sulfate mixture (content of taurine 95%); About 500K, do not have endotherm(ic)peak, about 600K, have tangible endotherm(ic)peak.So can analyze taurine through the content of 2-monoethanolamine sulfuric ester.
Five, embodiment:
Following examples have been merely and have further specified the present invention, do not limit content of the present invention.
Embodiment 1:
The present invention adopts the ammonium sulphite sulfonation to prepare the method for taurine, and the detailed step of this method is following:
A, esterification: at first adopting ordinary method is that raw material carries out esterification with the vitriol oil and thanomin, the synthetic midbody 2-monoethanolamine sulfuric ester that obtains;
B, sulfonation reaction: 5min feeds ammonia (purpose of feeding ammonia is that system is protected in reaction vessel before reaction beginning; Make system be alkalescence; Suppress the hydrolysis of 2-monoethanolamine sulfuric ester, and in step c, recycle and reuse), ammonia flow is 15mLmin -1At first add step a synthetic midbody 2-monoethanolamine sulfuric ester, add ammonium sulphite then, said ammonium sulphite and 2-monoethanolamine sulfuric ester between the two the mol ratio of add-on be 1.55:1; Begin to carry out sulfonation reaction; Control sulfonation reaction temperature is 98 ℃, and the reaction times is 11h, and the feed way of raw material ammonium sulphite is 4 times; After sulfonation reaction finishes; With the reaction soln cooling,, measure the yield that calculates the gained taurine with Sulfothiorine residual titration method when gained reaction soln temperature is reduced to below 65 ℃;
C, step b gained reaction soln is reduced to room temperature, add Ca (OH) then therein 2Solution, Ca (OH) 2The concentration of solution is 0.1molL -1, add Ca (OH) 2Obtain mother liquor behind the solution, heat mother liquid obtainedly, remove the ammonia in the mother liquor, and collect the ammonia of removing and utilize again to 45~80 ℃; Reduce the mother liquor temperature then, carry out suction filtration after reducing to room temperature, obtain precipitate C aSO when mother liquid obtained 4, when sulphate content is lower than 1% in the gained filtrating after measuring suction filtration, stop to add Ca (OH) 2Solution;
D, adopt the crystallisation by cooling method that contained taurine is wherein purified step c gained filtrating, at first adopting phosphate buffered saline buffer to regulate pH value of filtrate is 6, and progressively cooling; Rate of temperature fall is 1.5 ℃/min; Reduce to and carry out crystallization when Tc is 15 ℃, crystallization time is 9h (stir speed (S.S.) of magnetic stirring apparatus is 600r/min in cooling, the crystallisation process), and the gained crystal is carried out suction filtration; Dry then to constant weight (bake out temperature is 80 ℃), obtain product taurine crystal;
E, the product taurine crystal by adopting heat analysis method that steps d is obtained are analyzed.
The product analysis result: be determined in the sulfonation reaction through Sulfothiorine residual titration method, the transformation efficiency of 2-monoethanolamine sulfuric ester is 62.51%, and the desalination rate is 99.12%.After crystallization finished, a yield of taurine was 61.11%, and purity reaches 95%.
Embodiment 2: basic identical with embodiment 1, difference is:
Among the step b: ammonia flow is 10mLmin -1, said ammonium sulphite and 2-monoethanolamine sulfuric ester between the two the mol ratio of add-on be 1.75:1, control sulfonation reaction temperature is 98 ℃, the reaction times is 12h, the feed way of raw material ammonium sulphite is 2 times;
In the steps d: at first adopting phosphate buffered saline buffer to regulate pH value of filtrate is 6; And progressively cooling; Rate of temperature fall is 4 ℃/min, reduces to and carries out crystallization when Tc is 14 ℃, and crystallization time is 6h (stir speed (S.S.) of magnetic stirring apparatus is 400r/min in cooling, the crystallisation process); The gained crystal is carried out suction filtration, dry then to constant weight (bake out temperature is 80 ℃).
The product analysis result: be determined in the sulfonation reaction through Sulfothiorine residual titration method, the transformation efficiency of 2-monoethanolamine sulfuric ester is 67.41%, and the desalination rate is 99.18%.After crystallization finished, a yield of taurine was 52.47%, and purity reaches 95%.
Embodiment 3: basic identical with embodiment 1, difference is:
Among the step b: ammonia flow is 10mLmin -1, said ammonium sulphite and 2-monoethanolamine sulfuric ester between the two the mol ratio of add-on be 1.65:1, control sulfonation reaction temperature is 95 ℃, the reaction times is 12h, the feed way of raw material ammonium sulphite is 4 times;
In the steps d: at first adopting phosphate buffered saline buffer to regulate pH value of filtrate is 6; And progressively cooling; Rate of temperature fall is 3 ℃/min, reduces to and carries out crystallization when Tc is 14 ℃, and crystallization time is 10h (stir speed (S.S.) of magnetic stirring apparatus is 600r/min in cooling, the crystallisation process); The gained crystal is carried out suction filtration, dry then to constant weight (bake out temperature is 80 ℃).
The product analysis result: be determined in the sulfonation reaction through Sulfothiorine residual titration method, the transformation efficiency of 2-monoethanolamine sulfuric ester is 70.43%, and the desalination rate is 99.24%.After crystallization finished, a yield of taurine was 65.32%, and purity reaches 95%.
Embodiment 4: basic identical with embodiment 1, difference is:
Among the step b: ammonia flow is 18mLmin -1, said ammonium sulphite and 2-monoethanolamine sulfuric ester between the two the mol ratio of add-on be 1.75:1, control sulfonation reaction temperature is 98 ℃, the reaction times is 12h, the feed way of raw material ammonium sulphite is 4 times;
In the steps d: at first adopting phosphate buffered saline buffer to regulate pH value of filtrate is 6; And progressively cooling; Rate of temperature fall is 2 ℃/min, reduces to and carries out crystallization when Tc is 14 ℃, and crystallization time is 10h (stir speed (S.S.) of magnetic stirring apparatus is 600r/min in cooling, the crystallisation process); The gained crystal is carried out suction filtration, dry then to constant weight (bake out temperature is 80 ℃).
The product analysis result: be determined in the sulfonation reaction through Sulfothiorine residual titration method, the transformation efficiency of 2-monoethanolamine sulfuric ester is 76.31%, and the desalination rate is 99.19%.After crystallization finished, a yield of taurine was 72.21%, and purity reaches 95%.
Embodiment 5: basic identical with embodiment 1, difference is:
Among the step b: ammonia flow is 20mLmin -1, said ammonium sulphite and 2-monoethanolamine sulfuric ester between the two the mol ratio of add-on be 1.75:1, control sulfonation reaction temperature is 98 ℃, the reaction times is 12h, the feed way of raw material ammonium sulphite is 4 times;
In the steps d: at first adopting phosphate buffered saline buffer to regulate pH value of filtrate is 6; And progressively cooling; Rate of temperature fall is 1 ℃/min, reduces to and carries out crystallization when Tc is 14 ℃, and crystallization time is 12h (stir speed (S.S.) of magnetic stirring apparatus is 500r/min in cooling, the crystallisation process); The gained crystal is carried out suction filtration, dry then to constant weight (bake out temperature is 100 ℃).
The product analysis result: be determined in the sulfonation reaction through Sulfothiorine residual titration method, the transformation efficiency of 2-monoethanolamine sulfuric ester is 77.25%, and the desalination rate is 99.25%.After crystallization finished, a yield of taurine was 81.27%, and purity reaches 95%.

Claims (9)

1. a method that adopts the ammonium sulphite sulfonation to prepare taurine is characterized in that, said method comprising the steps of:
A, esterification: at first adopting ordinary method is that raw material carries out esterification with the vitriol oil and thanomin, the synthetic midbody 2-monoethanolamine sulfuric ester that obtains;
B, sulfonation reaction: preceding 4~6min feeds ammonia in reaction vessel in the reaction beginning, and ammonia flow is 10~20mLmin -1At first add step a synthetic midbody 2-monoethanolamine sulfuric ester, add ammonium sulphite then, said ammonium sulphite and 2-monoethanolamine sulfuric ester between the two the mol ratio of add-on be 1~5:1; Begin to carry out sulfonation reaction; Control sulfonation reaction temperature is 35~110 ℃, and the reaction times is 5~20h, and the feed way of raw material ammonium sulphite is 1~10 time; After sulfonation reaction finishes; With the reaction soln cooling,, measure the yield that calculates the gained taurine with Sulfothiorine residual titration method when gained reaction soln temperature is reduced to below 65 ℃;
C, step b gained reaction soln is reduced to room temperature, add Ca (OH) then therein 2Solution, Ca (OH) 2The add-on of solution is that 1~5 mole of ammonium sulphite adding concentration is 0.1molL -1Ca (OH) 2Solution 0.1~0.6L adds Ca (OH) 2Obtain mother liquor behind the solution, heat mother liquid obtainedly, remove the ammonia in the mother liquor, and collect the ammonia of removing and utilize again to 45~80 ℃; Reduce the mother liquor temperature then, carry out suction filtration after reducing to room temperature, obtain precipitate C aSO when mother liquid obtained 4, when sulphate content is lower than 1% in the gained filtrating after measuring suction filtration, stop to add Ca (OH) 2Solution;
D, adopt the crystallisation by cooling method that contained taurine is wherein purified step c gained filtrating, at first adopting phosphate buffered saline buffer to regulate pH value of filtrate is 5~7, and progressively cooling; Rate of temperature fall is 0.05~4 ℃/min; Reduce to and carry out crystallization when Tc is 5~30 ℃, crystallization time is 1~15h, and the gained crystal is carried out suction filtration; Dry then to constant weight, obtain product taurine crystal;
E, the product taurine crystal by adopting heat analysis method that steps d is obtained are analyzed .
2. employing ammonium sulphite according to claim 1 sulfonation prepares the method for taurine; It is characterized in that: the preceding 4~6min of reaction beginning feeds ammonia among the step b in reaction vessel; System is protected; Make system be alkalescence, suppress the hydrolysis of 2-monoethanolamine sulfuric ester, and in step c, recycle and reuse.
3. employing ammonium sulphite according to claim 1 sulfonation prepares the method for taurine, it is characterized in that: among the step b ammonium sulphite and 2-monoethanolamine sulfuric ester between the two the mol ratio of add-on be 1.3~1.8:1.
4. employing ammonium sulphite according to claim 1 sulfonation prepares the method for taurine, it is characterized in that: control sulfonation reaction temperature is 65~105 ℃ among the step b, and the reaction times is 8~12h.
5. employing ammonium sulphite according to claim 1 sulfonation prepares the method for taurine, it is characterized in that: the feed way of the ammonium sulphite of raw material described in the step b is 1~4 time.
6. employing ammonium sulphite according to claim 1 sulfonation prepares the method for taurine, it is characterized in that: rate of temperature fall described in the steps d is 0.5~3 ℃/min; The stir speed (S.S.) of magnetic stirring apparatus is 100~800r/min in cooling, the crystallisation process.
7. employing ammonium sulphite according to claim 6 sulfonation prepares the method for taurine, it is characterized in that: the stir speed (S.S.) 400~600r/min of magnetic stirring apparatus in said cooling, the crystallisation process.
8. employing ammonium sulphite according to claim 1 sulfonation prepares the method for taurine, it is characterized in that: reduce in the steps d and carry out crystallization when Tc is 14~25 ℃, crystallization time is 3~12h.
9. employing ammonium sulphite according to claim 1 sulfonation prepares the method for taurine, it is characterized in that: dry described in the steps d to constant weight, its bake out temperature is 80~100 ℃.
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US9145359B2 (en) 2013-12-30 2015-09-29 Songzhou Hu Cyclic process for the production of taurine from monoethanolamine
CN110511165A (en) * 2019-08-01 2019-11-29 苏州汉德创宏生化科技有限公司 A kind of synthetic method of taurine precursor 2- ethylaminoethanol sulfuric ester
CN112679391A (en) * 2020-12-25 2021-04-20 江苏远洋药业股份有限公司 Method for producing taurine by concentrated sulfuric acid direct catalysis method
CN113200879A (en) * 2020-09-09 2021-08-03 维生源知识产权有限责任公司 Circulation method for producing taurine from ethanolamine
CN113200878A (en) * 2020-09-09 2021-08-03 维生源知识产权有限责任公司 Circulation method for producing taurine from ethanolamine
CN113214095A (en) * 2020-09-09 2021-08-06 维生源知识产权有限责任公司 Circulation method for producing taurine from ethanolamine
WO2021195001A1 (en) * 2020-03-23 2021-09-30 Archer Daniels Midland Company Process sulfonation to produce taurine
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USRE49370E1 (en) 2013-12-30 2023-01-17 Vitaworks Ip, Llc Cyclic process for the production of taurine from monoethanolamine
US9145359B2 (en) 2013-12-30 2015-09-29 Songzhou Hu Cyclic process for the production of taurine from monoethanolamine
JP2021534087A (en) * 2018-08-02 2021-12-09 アーチャー−ダニエルズ−ミッドランド カンパニー How to make bio-based products from sugar
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CN110511165A (en) * 2019-08-01 2019-11-29 苏州汉德创宏生化科技有限公司 A kind of synthetic method of taurine precursor 2- ethylaminoethanol sulfuric ester
CN114736141A (en) * 2019-08-01 2022-07-12 苏州汉德创宏生化科技有限公司 Synthetic method of taurine precursor 2-aminoethanol sulfate
WO2021195001A1 (en) * 2020-03-23 2021-09-30 Archer Daniels Midland Company Process sulfonation to produce taurine
CN113200878A (en) * 2020-09-09 2021-08-03 维生源知识产权有限责任公司 Circulation method for producing taurine from ethanolamine
US11161808B1 (en) 2020-09-09 2021-11-02 Vitaworks Ip, Llc Cyclic process for producing taurine from monoethanolamine
US11254639B1 (en) * 2020-09-09 2022-02-22 Vitaworks Ip, Llc Cyclic process for producing taurine from monoethanolamine
US20220073455A1 (en) * 2020-09-09 2022-03-10 Vitaworks Ip, Llc Cyclic Process for Producing Taurine from Monoethanolamine
WO2022055781A1 (en) * 2020-09-09 2022-03-17 Vitaworks Ip, Llc Cyclic process for producing taurine from monoethanolamine
CN113214095A (en) * 2020-09-09 2021-08-06 维生源知识产权有限责任公司 Circulation method for producing taurine from ethanolamine
CN113200879A (en) * 2020-09-09 2021-08-03 维生源知识产权有限责任公司 Circulation method for producing taurine from ethanolamine
US11578036B2 (en) 2020-09-09 2023-02-14 Vitaworks Ip, Llc Cyclic process for producing taurine from monoethanolamine
US11623914B2 (en) 2020-09-09 2023-04-11 Vitaworks Ip, Llc Cyclic process for producing taurine from monoethanolamine
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CN112679391B (en) * 2020-12-25 2022-04-19 江苏远洋药业股份有限公司 Method for producing taurine by concentrated sulfuric acid direct catalysis method
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