CN101100449A - Method for synthesizing taurine - Google Patents
Method for synthesizing taurine Download PDFInfo
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- CN101100449A CN101100449A CNA2007100255706A CN200710025570A CN101100449A CN 101100449 A CN101100449 A CN 101100449A CN A2007100255706 A CNA2007100255706 A CN A2007100255706A CN 200710025570 A CN200710025570 A CN 200710025570A CN 101100449 A CN101100449 A CN 101100449A
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Abstract
Synthesis of taurine is carried out by: reducing esterified product of cholamine with ammonium sulfite as reducer, separating to generate crude product, and re-crystallizing to obtain final product. It's economical, has no SO2 gas discharge and has friendly production environment and can separate out taurine and sulfate at low temperature.
Description
Technical Field
The invention relates to a synthetic method of taurine, belonging to the technical field of organic chemical synthesis.
Background
Taurine (Taurine), also known as taurocholic acid, is a sulfur-containing, non-protein amino acid with the chemical name 2-aminoethanesulfonic acid (NH)2CH2CH2SO3H) In recent years, taurine has been widely used in recent years as the physiological action and nutritional value thereof are studied in depth, and has important applications in the fields of medicines, foods, fuels, surfactants, PH buffers, and the like. Taurine as medicine can be used for promoting bile flow,protecting liver, removing toxic substance, diminishing inflammation, relieving fever, tranquilizing mind, relieving convulsion, resisting arrhythmia, treating cardiac insufficiency, regulating osmotic pressure, lowering blood pressure, treating arteriosclerosis, inhibiting central nerve, and maintaining vision. At present, in some developed countries in the world, such as the United states and Japan, proper amount of taurine is added into milk and milk powder for infants so as to ensure the health and normal development of infants. In China, many enterprises develop a series of infants and young children development attentions in the last two yearsTaurine-containing commercial products; modern researches show that taurine has a series of unique functions on cardiovascular systems of adults, and has the effects of strengthening physique, preventing diseases, relieving fatigue and improving working efficiency.
Taurine has been discovered, and synthetic pathways have been continuously explored. To date, there are not dozens of methods for synthesizing taurine. The existing chemical synthesis methods for obtaining taurine mainly comprise the following three methods.
1. Dichloroethane process
The dichloroethane method reacts with sodium sulfite to obtain 2-sodium chloroethanesulfonate, which reacts with ammonia under heating and pressurization to obtain 2-aminoethanesulfonic acid sodium, and then the taurine is prepared by acidification with hydrochloric acid, and the chemical reaction equation is as follows:
CLCH2CH2CL+Na2SO3→CLCH2CH2SO3Na+NaCL
CLCH2CH2SO3Na+2NH3→NH2CH2CH2SO3Na+NH4CL
NH2CH2CH2SO3Na+HCL→NH2CH2CH2SO3H+NaCL
the method has the advantages of more production raw materials, more production steps, more byproducts and high cost, and the reaction is carried out under heating and pressurization, so the manufacturing cost of an industrial device is high.
2. Ethylene oxide process
Ethylene oxide reacts with sodium bisulfite to produce sodium 2-hydroxyethanesulfonate, which reacts with ammonia under pressure to produce sodium 2-aminoethanesulfonate, which is acidified with hydrochloric acid to produce taurine, the chemical reaction formula:
HOCH2CH2SO3Na+NH3-NH2CH2CH2SO3Na+H2O
NH2CH2CH2SO3Na+Hcl→NH2CH2CH2SO3H+Nacl
the method is carried out under heating and pressurizing, and the industrial device has high cost.
3. Method for reducing ethanolamine sulfate by using sodium sulfite as reducing agent
Ethanolamine is used as a raw material, and is synthesized in two steps, and the synthesis route can be divided into an esterification method, a chlorination method and an imine method. The esterification method (also called esterification reduction method and sulfuric acid method) is easy to obtain raw materials, the yield is higher than that of other methods, and the method is adopted by most manufacturers at home and abroad and has a chemical reaction formula:
NH2CH2CH2OH+H2SO4→NH2CH2CH2OSO3H+H2O
NH2CH2CH2OSO3H+Na2SO3→NH2CH2CH2SO3H+Na2SO4
the method is divided into the following steps in the actual industrialized process:
(1) salifying:
NH2CH2CH2OH+H2SO4→NH2CH2CH2OH·H2SO4
reduced pressure
(2) Esterification:
NH2CH2CH2OH·H2SO4→NH2CH2CH2OSO3H+H2O
dewatering
(3) Reduction:
NH2CH2CH2OSO3H+Na2SO3→NH2CH2CH2SO3H++Na2SO4
in the above three-step reaction, there are the following side reactions:
(1) hydrolysis of the ester:
(2) intermolecular dehydration of the ester:
2NH2CH2CH2OSO3H→NH2CH2CH2OSO2NHCH2OSO3H+H2O
(3)Na2SO3oxidation of (2):
2Na2SO3+O2→2Na2SO4
(4)Na2SO3hydrolysis of (2):
ethanolamine sulfate is susceptible to hydrolysis reaction in both acidic and alkaline environments, and for this reason, the acidic compound is adjusted to neutral (pH 7) before reduction reaction. Soda ash (Na) is adopted by a plurality of manufacturers (including laboratories)2CO3) Solution conditioning, chemical reaction formula:
Na2CO3+H2SO4→Na2SO4+CO2↑+H2O
the method is difficult to control in the actual production process, is difficult to accurately measure the pH value, is easy to cause the addition of excessive soda ash, and is more complicated to separate taurine from sodium sulfate2Gas, make production ringThe environment is extremely harsh, and therefore, a clean production process which is simple, convenient, economical and reliable and can separate out taurine at low temperature is urgently needed.
Disclosure of Invention
The invention aims to overcome the defects of the process and provide a simple, convenient, feasible and economic method for synthesizing taurine, which is safe and can realize clean production.
The invention aims to achieve the purpose, and the synthesis method of the taurine is to perform reduction reaction on an esterified product of ethanolamine by taking ammonium sulfite as a reducing agent, separate to obtain a crude product, and recrystallize to obtain the finished product taurine.
The feeding molar ratio of the ammonium sulfite salt to the ester of the ethanolamine is 1-2: 1-1.5.
The feeding molar ratio of the ammonium sulfite salt to the ester of the ethanolamine is 1.2: 1.
The esterified substance of the ethanolamine is any one of ethanolamine sulfate, ethanolamine hydrochloride, ethanolamine phosphate and ethanolamine acetate.
The ester of ethanolamine is ethanolamine sulfate.
The ammonium sulfite salt is ammonium bisulfite or ammonium sulfite or a mixture of the ammonium bisulfite and the ammonium sulfite.
The mixing proportion of the mixture is any proportion.
The reduction reaction has the reaction temperature of 75-135 ℃ and the time of 10-60 h.
The reduction reaction has the reaction temperature of 90-120 ℃ and the time of 12-24 h.
The reduction reaction is any one of reaction under normal pressure or negative pressure or under the pressure higher than normal pressure, and the reaction container adopted by the reduction reaction is any one of a glass lining reaction container or a metal reaction container.
The method has the advantages that the taurine and the sulfate can be separated at low temperature, so that the method has economical efficiency; no SO is generated in the production process2The gas escapes, so the production is environment-friendly.
The specific implementation mode is as follows:
the chemical reaction equation of the method for synthesizing taurine recommended by the invention is as follows:
NH2CH2CH2OSO3H+(NH4)2SO3+(NH4)HSO3
＝＝NH2CH2CH2SO3H+(NH4)2SO4+(NH4)HSO4
example 1:
588kg (2.97X 10) of ammonium bisulfite (50%) was placed in a 1000L glass-lined A3 reactor with stirring, heating, refluxing, and setting-up3mol), 138kg (1.74X 10) of ammonium bicarbonate are added with stirring3mol) until no carbon dioxide gas is released, 352.5kg (2.5X 10) of ethanolamine sulfuric acid ester is added3mol), heating and stirring to 75 ℃, maintaining the pressure in the kettle at-0.08 MPa, continuously reacting for 60 hours, cooling to 10 ℃ while stirring, and centrifugally separating to obtain 360kg of crude taurine.
Putting 360kg of the crude taurine into a 1000L reaction kettle, adding 500L of water and 0.5kg of activated carbon, heating and stirring to dissolve the crude taurine, filtering to remove the activated carbon to obtain colorless transparent liquid, cooling to 5 ℃ under stirring, centrifugally separating, washing to obtain 220kg of refined taurine, and drying to obtain 201kg (1.61 multiplied by 10) of finished taurine3mol), all indexes are in accordance with Japanese pharmacopoeia JP8 edition and United states pharmacopoeia USP26 edition.
Example 2:
650kg (3.29X 10%) of liquid ammonium bisulfite (50%) were added to a 1000L glass-lined A3 reactor equipped with a stirring, heating and refluxing device3mol) is added, ammonium bicarbonate with equal mol is added and stirredThe ammonium sulfite was produced by reacting with stirring, and 391kg (4.93X 10) of ethanolamine hydrochloride was added under stirring3mol), heating and stirring to 90 ℃, continuously reacting for 50h under the condition of normal pressure, then cooling to 10 ℃ under stirring, and centrifugally separating to obtain 430kg of crude taurine.
Putting 430kg of crude taurine into a 1000L reaction kettle, adding 500L of water and 1kg of activated carbon, heating and stirring to dissolve the crude taurine, filtering to remove the activated carbon to obtain colorless transparent liquid, cooling to 10 ℃ under stirring, performing centrifugal separation, washing to obtain 243kg of refined taurine, and drying to obtain 210kg (1.68 multiplied by 10) of finished taurine3mol), all indexes are in accordance with JP8 and USP26 after detection.
Example 3:
645kg (3.29X 10) of liquid ammonium bisulfite (50%) was added to a 1000L stainless steel reactor with stirring, heating, refluxing, and sealing means3mol) and 450kg (3.19X 10) of ethanolamine phosphate are added with stirring3mol), pressurizing to 0.4MPa, heating to 115 ℃, keeping the temperature for 50h, cooling to 10 ℃ under stirring, and performing centrifugal separation to obtain 400kg of crude taurine.
Putting 400kg of the crude taurine into a 1000L reaction kettle, adding 500L of water and 1kg of activated carbon, heating and stirring to dissolve the crude taurine, filtering to remove the activated carbon to obtain colorless transparent liquid, cooling to 10 ℃ under stirring, centrifugallyseparating, and washing to obtain 225kg (1.8 multiplied by 10) of refined taurine3mol) and dried to obtain 200kg (1.6 multiplied by 10) of finished taurine3mol), all indexes are in accordance with JP8 and USP26 after detection.
Example 4:
58kg (0.297X 10) of ammonium bisulfite (50%) was placed in a 100L stainless steel reactor equipped with stirring, heating and refluxing devices3mol), 3kg (0.176X 10) of liquid ammonia are introduced with stirring3mol), add ethanolamine acetate 25kg (0.25X 10)3mol), introducing pure nitrogen for protection, keeping the temperature at 0.3MPa, heating, stirring to 90 ℃, keeping the temperature for 14 hours, cooling to 8 ℃ while stirring, and performing centrifugal separation to obtain 34kg of crude taurine.
Putting 34kg of the crude taurine into a 100L reaction kettle, adding 50L of water and 0.05kg of activated carbon, heating and stirring to dissolve the crude taurine, filtering to remove the activated carbon to obtain colorless transparent liquid, cooling to 5 ℃ under stirring, centrifugally separating, washing to obtain 18kg of refined taurine, and drying to obtain 17kg (0.138 multiplied by 10) of finished taurine3mol), all indexes are in accordance with JP8 and USP26 after detection.
Example 5:
5820kg (29.7X 10) of ammonium bisulfite (50%) was placed in a 10000L stainless steel reactor with stirring, heating and refluxing apparatus3mol), 300kg (17.6X 10) of liquid ammonia are introduced with stirring3mol), ethanolamine acetate 3670kg (35.6X 10) was added3And mol), introducing pure nitrogen for protection, heating to 100 ℃ under normal pressure, keeping the temperature for 60 hours, then cooling to 8 ℃ under stirring, and carrying out centrifugal separation to obtain 3605kg of crude taurine.
Putting 3605kg of crude taurine into a 10000L reaction kettle, adding 5000L of water and 5kg of activated carbon, dissolving the crude taurine under heating and stirring, filtering to remove the activated carbon to obtain colorless transparent liquid, cooling to 8 ℃ under stirring, centrifugally separating, washing to obtain 190kg of refined taurine, and drying to obtain 1792kg (14.3 multiplied by 10) of finished taurine3mol), all indexes are in accordance with JP8 and USP26 after detection.
Example 6:
32g (0.164mol) of liquid ammonium bisulfite (50%) is added into a 1000ml four-neck flask with a stirring, heating and refluxing device, ammonium bicarbonate with equal mole is added, the reaction is carried out under stirring to produce ammonium sulfite, 499g (3.61mol) of ammonium sulfite (86.5%) is added, 254g (2.2mol) of ethanolamine hydrochloride is added under stirring, the mixture is heated to 110 ℃, the mixture is stirred to reflux under normal pressure and is continuously refluxed for 30h, the temperature is reduced to 10 ℃ under stirring, and the crude taurine 428g is obtained after centrifugal separation.
428g of crude taurine is put into a 1000ml four-neck flask with a stirring, heating and refluxing device, 500ml of water and 1g of activated carbon are added, the crude taurine is dissolved under the conditions of heating and stirring, the activated carbon is filtered off to obtain colorless transparent liquid, the temperature is reduced to 10 ℃ under the condition of stirring, refined taurine 238.5g is obtained through centrifugal separation and washing, the refined taurine is dried to obtain 218g (1.72mol) of finished taurine, and all indexes of the finished taurine accord with JP8 and USP26 through detection.
Example 7:
592kg (3.02X 10) of liquid ammonium bisulfite (50%) was added to a 1000L glass-lined A3 reactor equipped with a stirring, heating and refluxing device3mol), adding ammonium bicarbonate with equal mol, reacting under stirring to produce ammonium sulfite, and adding 24kg (0.182 × 10%) of ammonium sulfite (86.5%)3mol) and 366.6kg (2.6X 10) of ethanolamine sulfate are added with stirring3mol), heating to 100 ℃, stirring for 60h under normal pressure, then cooling to 8 ℃ under stirring, and centrifuging to obtain 370kg of crude taurine.
Putting 370kg of crude taurine into a 1000L reaction kettle, adding 500L of water and 1kg of activated carbon, heating and stirring to dissolve the crude taurine, filtering to remove the activated carbon to obtain colorless transparent liquid, cooling to 8 ℃ under stirring, performing centrifugal separation, washing to obtain 230kg of refined taurine, and drying to obtain 208kg (1.66 multiplied by 10) of finished taurine3mol), all indexes are in accordance with JP8 and USP26 after detection.
Example 8:
696.7kg (5.2X 10%) of ammonium sulfite (86.5%) was added to a 1000L glass-lined A3 reactor equipped with a stirring, heating and refluxing device3mol), 366.6kg (2.6X 10 kg) of ethanolamine sulfate are added with stirring3mol), heating to 105 ℃, continuing stirring for 50h under normal pressure, and then reducing the temperature to 8 ℃ under stirringCentrifuging at the temperature of 365kg of crude taurine is obtained.
Putting 365kg of the crude taurine into a 1000L reaction kettle, adding 500L of water and 1kg of activated carbon, heating and stirring to dissolve the crude taurine, filtering to remove the activated carbon to obtain colorless transparent liquid, cooling to 8 ℃ under stirring, centrifugally separating, washing to obtain 230kg of refined taurine, and drying to obtain 208kg (1.661 multiplied by 10) of the finished taurine3mol), all indexes are in accordance with JP8 and USP26 after detection.
Example 9:
stirring the mixture in a 1000L stirring belt,514.5kg (3.84X 10) of ammonium sulfite is added into a glass lining A3 reaction kettle of a heating and refluxing device3mol), 254kg (3.2X 10) of ethanolamine hydrochloride are added with stirring3mol), heating to 135 ℃, continuing to react for 10 hours under normal pressure, then cooling to 10 ℃ under stirring, and centrifugally separating to obtain 426kg of crude taurine.
Putting 426kg of crude taurine into a 1000L reaction kettle, adding 500L of water and 1kg of activated carbon, heating and stirring to dissolve the crude taurine, filtering to remove the activated carbon to obtain colorless transparent liquid, cooling to 10 ℃ under stirring, performing centrifugal separation, washing to obtain 241kg of refined taurine, and drying to obtain 209kg (1.67 multiplied by 10) of finished taurine3mol), all indexes are in accordance with JP8 and USP26 after detection.
Example 10:
255Kg (1.3X 10) of liquid ammonium bisulfite (50%) is added into a 1000L glass-lined A3 reaction kettle with stirring, heating and refluxing devices3mol), adding ammonium bicarbonate with equal mol, reacting under stirring to produce ammonium sulfite, and adding 244Kg (1.82X 10%) of ammonium sulfite (86.5%)3mol) and 366.6Kg of ethanolamine sulfate (2.6X 10) are added under stirring3mol), heating to 95 ℃, continuing to react for 40h under normal pressure, then cooling to 8 ℃ under stirring, and centrifugally separating to obtain 370Kg of crude taurine.
Putting 370Kg of the crude taurine into a 1000L reaction kettle, adding 500L and1Kg of activated carbon, heating and stirring to dissolve the crude taurine, filtering to remove the activated carbon to obtain colorless transparent liquid, cooling to 8 deg.C under stirring, centrifuging, washing to obtain 230Kg of refined taurine, and drying to obtain 208Kg (1.66X 10) of taurine3mol), all indexes are in accordance with JP8 and USP26 after detection.
Claims (10)
1. A method for synthesizing taurine is characterized in that ammonium sulfite is used as a reducing agent to carry out reduction reaction on an esterified product of ethanolamine, a crude product is obtained by separation, and the crude product is recrystallized to obtain the finished product taurine.
2. A method for synthesizing taurine according to claim 1, wherein the molar ratio of the ammonium sulfite salt to the ester of ethanolamine is 1-2: 1-1.5.
3. A method for synthesizing taurine according to claim 1, wherein the molar ratio of the ammonium sulfite salt to the ester of ethanolamine is 1.2: 1.
4. A method for synthesizing taurine as claimed in claim 1, 2 or 3, wherein the esterified product of ethanolamine is any one of ethanolamine sulfate, ethanolamine hydrochloride, ethanolamine phosphate and ethanolamine acetate.
5. A method for synthesizing taurine as claimed in claim 1, 2 or 3, wherein the ester of ethanolamine is ethanolamine sulfate.
6. A method of synthesizing taurine as claimed in claim 1, 2 or 3, wherein the ammonium sulfite salt is ammonium bisulfite or ammonium sulfite or a mixture of ammonium bisulfite and ammonium sulfite.
7. A method for synthesizing taurine according to claim 6, wherein the mixing ratio of the taurine is an arbitrary ratio.
8. The method for synthesizing taurine according to claim 1, wherein the reduction reaction is performed at 75 to 135 ℃ for 10 to 60 hours.
9. A method for synthesizing taurine according to claim 1 or 7, wherein the reaction temperature of the reduction reaction is 90 to 120 ℃ and the time is 12 to 24 hours.
10. A method for synthesizing taurine according to claim 9, wherein the reduction reaction is performed at normal pressure, negative pressure, or a pressure higher than normal pressure, and the reaction vessel used in the reduction reaction is either a glass-lined reaction vessel or a metal reaction vessel.
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101486669B (en) * | 2009-01-09 | 2012-02-22 | 沙洋天一药业有限公司 | Method for synthesizing taurine |
| CN102633689A (en) * | 2012-04-09 | 2012-08-15 | 郑州大学 | Method for preparing taurine by adopting sulfonation of ammonium sulfite |
| CN102659644A (en) * | 2012-05-10 | 2012-09-12 | 南京优科生物医药有限公司 | Crystal forms of 2-aminoethyl sulfonic acid and preparation processes for crystal forms |
| CN102702037A (en) * | 2012-05-24 | 2012-10-03 | 福建创鑫科技开发有限公司 | Method for preparing ethylenediamino ethyl sulfonate |
| US9145359B2 (en) | 2013-12-30 | 2015-09-29 | Songzhou Hu | Cyclic process for the production of taurine from monoethanolamine |
| CN111302981A (en) * | 2018-12-11 | 2020-06-19 | 万华化学集团股份有限公司 | Method for preparing taurine |
| CN112645847A (en) * | 2020-12-25 | 2021-04-13 | 江苏远洋药业股份有限公司 | Taurine high-alkali anhydrous production process |
| WO2021108179A1 (en) * | 2019-11-27 | 2021-06-03 | Archer Daniels Midland Company | Process sulfonation of aminoethylene sulfonic ester to produce taurine |
| 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 |
| US11161808B1 (en) | 2020-09-09 | 2021-11-02 | Vitaworks Ip, Llc | Cyclic process for producing taurine from monoethanolamine |
| US11578036B2 (en) | 2020-09-09 | 2023-02-14 | Vitaworks Ip, Llc | Cyclic process for producing taurine from monoethanolamine |
-
2007
- 2007-08-03 CN CNA2007100255706A patent/CN101100449A/en active Pending
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101486669B (en) * | 2009-01-09 | 2012-02-22 | 沙洋天一药业有限公司 | Method for synthesizing taurine |
| CN102633689A (en) * | 2012-04-09 | 2012-08-15 | 郑州大学 | Method for preparing taurine by adopting sulfonation of ammonium sulfite |
| CN102659644A (en) * | 2012-05-10 | 2012-09-12 | 南京优科生物医药有限公司 | Crystal forms of 2-aminoethyl sulfonic acid and preparation processes for crystal forms |
| CN102659644B (en) * | 2012-05-10 | 2014-02-19 | 南京优科生物医药有限公司 | Crystal forms of 2-aminoethyl sulfonic acid and preparation processes for crystal forms |
| CN102702037A (en) * | 2012-05-24 | 2012-10-03 | 福建创鑫科技开发有限公司 | Method for preparing ethylenediamino ethyl sulfonate |
| US9145359B2 (en) | 2013-12-30 | 2015-09-29 | Songzhou Hu | Cyclic process for the production of taurine from monoethanolamine |
| CN105152985A (en) * | 2013-12-30 | 2015-12-16 | 胡松洲 | Cyclic process for the production of taurine from monoethanolamine |
| USRE49370E1 (en) | 2013-12-30 | 2023-01-17 | Vitaworks Ip, Llc | Cyclic process for the production of taurine from monoethanolamine |
| CN111302981A (en) * | 2018-12-11 | 2020-06-19 | 万华化学集团股份有限公司 | Method for preparing taurine |
| CN111302981B (en) * | 2018-12-11 | 2022-04-19 | 万华化学集团股份有限公司 | Method for preparing taurine |
| WO2021108179A1 (en) * | 2019-11-27 | 2021-06-03 | Archer Daniels Midland Company | Process sulfonation of aminoethylene sulfonic ester to produce taurine |
| US11254639B1 (en) | 2020-09-09 | 2022-02-22 | Vitaworks Ip, Llc | Cyclic process for producing taurine from monoethanolamine |
| US11161808B1 (en) | 2020-09-09 | 2021-11-02 | Vitaworks Ip, Llc | Cyclic process for producing taurine from monoethanolamine |
| 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 |
| CN112645847A (en) * | 2020-12-25 | 2021-04-13 | 江苏远洋药业股份有限公司 | Taurine high-alkali anhydrous production process |
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