CN109485586A - A kind of preparation method of taurine - Google Patents
A kind of preparation method of taurine Download PDFInfo
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- CN109485586A CN109485586A CN201811512124.2A CN201811512124A CN109485586A CN 109485586 A CN109485586 A CN 109485586A CN 201811512124 A CN201811512124 A CN 201811512124A CN 109485586 A CN109485586 A CN 109485586A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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Abstract
The present invention provides a kind of method for preparing taurine.Firstly, ethylene oxide and sodium hydrogensulfite obtain sodium isethionate through addition reaction is highly selective under heterogeneous catalysis effect；Secondly, synthesis sodium isethionate homogeneous catalyst catalysis under carry out ammonolysis reaction, then through neutralization, Crystallization Separation and etc. obtain finished product taurine.Compared with traditional production technology, which can substantially reduce the by-product of addition reaction process, and reduce the temperature and pressure of ammonolysis reaction, shorten the reaction time, easy to industrialized production.
Description
Technical field
The present invention relates to a kind of methods for preparing taurine.
Background technique
Taurine also known as cholaic acid, Taurine, chemical name 2-aminoethanesulfonic acid are a kind of nonproteins needed by human
Amino acid is present in a free form in nearly all internal organs of people and mammal.The effect of taurine and other amino acid
Difference, it can promote the growth and development of nervous system, protect brain, improve memory, can also be improved optic nerve conduction and view
Feel function, while also can cardioprotection, a variety of important functions of prevention and treatment cardiovascular and cerebrovascular disease etc..Taurine is with higher medicinal
Value, is important nutriment, is widely used in functional beverage, pet food, health food, feed, medicine and other fields,
Biochemical reagents and other organic synthesis intermediates also are used as, are a kind of with the fine chemicals that value is widely applied.
The chemical synthesis process of taurine mainly includes Girbotal process and epoxyethane method.Girbotal process reaction time is very
Long, wherein sulfonating reaction needs 30h or more, and high expensive, is gradually eliminated.Epoxyethane method uses ethylene oxide
With liquefied ammonia as raw material, cost is significantly lower than Girbotal process, and also outline is higher than Girbotal process to simultaneous reactions yield.In this advantage
Excitation under, at present epoxyethane method have become taurine production prevailing technology.
The crucial synthesis step of epoxyethane method is exactly that sodium isethionate reacts with liquefied ammonia and prepares sodium taurocholate, initial
Research in, due to being added without catalyst, need the harsh reaction condition of 200-280 DEG C of high temperature and 14-21MPa high pressure, this
It is high reaction process energy consumption is resulted in, production cost is higher.
Chinese patent CN105732440A is disclosed during the ammonolysis reaction containing mother liquid recycle, and alkali metal hydrogen can be added
Oxide, alkali carbonate (containing acid carbonate), iron series/aluminum-based metal salt, NiO/CeO2, it is any in rare earth oxide
One kind or combinations thereof is used as catalyst, and sodium taurocholate yield can be improved to 90-95%, but there is still a need for 255-265 DEG C of height for reaction
The pressure of mild 19-20MPa, condition are still more harsh.
The selection sodium hydroxide, potassium hydroxide, hydrogen during ammonolysis reaction is disclosed in Chinese patent CN107056659A
Lithia, sodium carbonate, potassium carbonate, any one or any two or more of mixtures in lithium carbonate as catalyst,
Ammonolysis reaction can be carried out at 250-270 DEG C, 10-15MPa at this time, the condition of the patent compared with patent CN105732440A only
It is slightly mild.
It is disclosed in sodium isethionate ammonolysis reaction in United States Patent (USP) US 20160355470A1, addition NaOH can be urged
Change ammonolysis reaction to carry out to the direction for generating sodium taurocholate, ammonolysis reaction can get 90% or more sodium taurocholate yield, ammonolysis
The yield of reaction is higher, but there is still a need for 160-260 DEG C of high temperature and Zi the high pressure of heating pressure to 26MPa.
In conclusion the ammonolysis reaction condition of existing Preparation Process of Taurine is still more harsh, and due to addition reaction
The by-products such as ethylene glycol are generated, cause mother liquor that can not apply completely during applying, therefore process conditions need to improve, to reduce life
Production process energy consumption reduces production cost, increases mother liquid recycle amount, improves taurine product yield.
Summary of the invention
The object of the present invention is to provide a kind of method for preparing sodium taurocholate, the more mild (temperature of the process conditions of this method
Spend that low, pressure is low), the reaction time is short, (for sodium isethionate yield up to 99% or more, ammonolysis is anti-in addition reaction for high income
Answer the yield of middle sodium taurocholate up to 89.0~95.0%, taurine one way crystallization yield is applied up to 70.0-75.0%, crystallization
Afterwards, taurine total recovery is up to 90.0~95.0%).
To reach the above goal of the invention, technical solution provided by the invention is as follows:
A method of taurine being prepared, ethylene oxide reacts preparation under heterogeneous catalysis effect with sodium hydrogensulfite
Sodium isethionate is obtained, then sodium isethionate reacts under bismuthates catalyst with ammonia is prepared taurine.
In the above method, the molar ratio of ethylene oxide and sodium hydrogensulfite can be 0.9:1~1.5:1, preferably 0.95:
1~1.2:1, more preferably 0.99:1~1.01:1.The heterogeneous catalysis is molecular sieve catalyst, and molecular sieve catalyst adds
Enter the 0.5-5wt%, preferably 1.0-3.0wt%, more preferably 1.0-2.5wt% that amount is sodium hydrogensulfite additional amount.Hydroxyl second
The mass ratio of base sodium sulfonate and ammonia can be 1:0.2~5, preferably 1:0.5~2, more preferable 1:0.7-1.5.Bismuthic acid salt catalyst
Dosage can be sodium isethionate 0.01-10wt%, preferably 0.05-5.0wt%, more preferably in 0.05-
0.5wt%.Molecular sieve catalyst is preferably that H-Beta (12.5) molecular sieve, dealuminzation De-Al-Beta (12.5) molecular sieve and tin change
One of Sn-Beta (12.5) molecular sieve of property is a variety of.Bismuthic acid salt catalyst can for sodium bismuthate, bismuthic acid ammonium, bismuthic acid potassium,
One of bismuthic acid lithium or bismuthic acid calcium are a variety of, preferably one of sodium bismuthate, bismuthic acid ammonium, bismuthic acid potassium or bismuthic acid lithium.
As a preferred solution, a method of preparing taurine, comprising the following steps:
(1) ethylene oxide reacts under heterogeneous catalysis catalysis with aqueous solution of sodium bisulfite, obtains isethionic acid
Sodium water solution；
(2) liquefied ammonia is passed through into isethionic acid sodium water solution；
(3) bismuthates homogeneous catalyst is added to being passed through in the isethionic acid aqueous solution after liquefied ammonia, obtains material liquid；
(4) after material liquid is heated, into being reacted to obtain reaction solution in high-pressure reactor；
(5) for reaction solution except neutralizing after ammonia, crystallization obtains taurine product.
Further, the concentration of step (1) sulfite hydrogen sodium of the present invention in aqueous solution is 10-40wt%, preferably
15-35wt%, more preferably 25-35wt%.
Further, the molar ratio of step (1) ethylene oxide and sodium hydrogensulfite of the present invention is 0.9:1~1.5:1, excellent
It is selected as 0.95:1~1.2:1, more preferably 0.99:1~1.01:1.
Heterogeneous catalysis is molecular sieve catalyst in step (1) of the present invention, and preferably H-Beta (12.5) molecular sieve takes off
One of Sn-Beta (12.5) molecular sieve of aluminium De-Al-Beta (12.5) molecular sieve and tin modification or a variety of, preferably H-
Beta (12.5) molecular sieve and Sn-Beta (12.5) molecular sieve, more preferably Sn-Beta (12.5) molecular sieve.
The additional amount of heterogeneous catalysis can be the 0.5-5wt% of sodium hydrogensulfite additional amount in step (1) of the present invention,
Preferably 1.0-3.0wt%, more preferably 1.0-2.5wt%.
Concentration of the liquefied ammonia in isethionic acid sodium water solution can be 10-30wt% in step (2) of the present invention, preferably
15-28wt%, more preferably 18-26wt%.
Preferably, the homogeneous metallic catalyst of bismuthates is sodium bismuthate, bismuthic acid ammonium, bismuthic acid potassium, bismuthic acid in step (3) of the present invention
One of lithium or bismuthic acid calcium are a variety of, one of more preferable sodium bismuthate, bismuthic acid ammonium, bismuthic acid potassium or bismuthic acid lithium.
The dosage of the homogeneous metallic catalyst of bismuthates can be the 0.01- of sodium isethionate in step (3) of the present invention
10wt%, preferably 0.05-5.0wt%, more preferably in 0.05-0.5wt%.
Sodium isethionate can be used or not use co-catalyst with reacting for ammonia in step (3) of the present invention, preferably make
Use co-catalyst；Co-catalyst is one of stannous chloride, ammonium chloride, ammonium bisulfite or a variety of, preferably stannous chloride.
The mass ratio of co-catalyst and bismuthic acid salt catalyst can be 0.1:1~1.5:1 in step (3) in the present invention, excellent
It is selected as 0.3:1~1.0:1, more preferably in 0.5:1~1.0:1.
The reaction temperature of step (4) can be 50-220 DEG C in the present invention, preferably 80-200 DEG C, more preferably 120-
160℃；The reaction pressure of step (3) is 0.1-12MPa, preferably 1-10MPa, more preferably 5-10MPa (gauge pressure)；Step
(3) reaction time in is 5-120min, preferably 10-80min, more preferably 20-60min.
Reaction solution is except after ammonia in step (5) of the present invention, can with the concentrated sulfuric acid at 50-90 DEG C in and system pH is adjusted to
Between 7-9.
Further, add sulfuric acid that system pH is adjusted between 7-9 in preferred steps (5) of the present invention；And/or crystallization is logical
It crosses and system is cooled to 20-40 DEG C to carry out.
Further, crystallization post mother liquor can be applied in ammonolysis reaction completely in step (5).
The process conditions that molecular sieve catalyst selected by addition reaction system of the present invention can be such that ethyleneoxide addition reacts
It is greatly reduced, the yield of intermediate product sodium isethionate can be improved to 99% or more, reduce the life of ethylene glycol in technique
At the principle is as follows: the suitable lewis acidity position in the molecular sieve catalyst selected in addition reaction can induce ring
Stable intermediates are formed between oxidative ethane and sulfurous acid hydrogen radical ion, so that ethylene oxide be promoted to be more easily generated hydroxyl second
Base sodium sulfonate.
The catalyst system of ammonolysis reaction of the present invention can be greatly improved sodium isethionate and prepare taurine process conditions
Principle it is as follows: in the ammonolysis reaction of sodium isethionate, compare the effect machine of the basic catalysts such as routine NaOH in patent
Reason is to utilize OH-The removing for promoting ammonium ion on hydroxyl in sodium isethionate, to promote the progress of ammonolysis reaction；And this
Inventing the bismuthic acid salt catalyst used then is to improve hydroxyl carbon using the compatibility of hydroxyl on bismuthic acid root and sodium isethionate
Electrophilic characteristic, while the presence of co-catalyst can improve the nucleophilicity of ammonia, so that ammonia nucleophilic attack hydroxyl carbon is advantageously promoted, and
The upper state four membered ring intermediate formed when will not generate base catalysis, thus required reaction temperature and pressure condition are more
Mildly, the simultaneous reactions time also shortens.
The positive effect of the present invention is:
(1) temperature of ethylene oxide and sodium hydrogensulfite addition reaction is reduced to 24-40 DEG C；
(2) yield of sodium isethionate in addition reaction is improved to 99% or more；
(3) the temperature condition of sodium isethionate ammonolysis reaction is reduced to 120-160 DEG C；
(4) pressure condition of sodium isethionate ammonolysis reaction is reduced to 5-10MPa；
(5) shorten the time of sodium isethionate ammonolysis reaction to 20-60min；
(6) yield of sodium taurocholate is up to 85.0~90.0% in ammonolysis reaction, and taurine total recovery is reachable after crystallization
90.0~95.0% (containing mother liquid recycle).
Specific embodiment
Following embodiment is not practical range for the purpose of limiting the invention, if not departing from the spirit and scope of the present invention,
It modifies or equivalently replaces the present invention, should all cover in the protection scope of the claims in the present invention.
Dinitrofluorobenzene and CuCl are purchased from Sigma-Aldrich (Sigma-Aldrich) trade Co., Ltd；NaBiO3、
NH4BiO3、LiBiO3And KBiO3Purchased from Shanghai Aladdin biochemical technology limited liability company；Ethylene oxide is purchased from Chinese medicines group
Learn reagent Co., Ltd；Sodium hydrogensulfite is purchased from Shanghai Xi Long Chemical Co., Ltd.；Molecular sieve catalyst is purchased from Nankai's catalyst
Factory.
Taurine is analyzed by the liquid chromatogram equipped with UV detector, and liquid chromatogram is agilent company 1200
Series, equipped with C18 liquid-phase chromatographic column, column temperature sets 40 DEG C, with the NaH of acetonitrile and 0.05mol/L2PO4Solution is mobile phase,
Flow velocity is 1.0mL/min, is detected at UV detector 360nm wavelength, external standard method is quantified.Sample is before sample introduction, first
It is suitably diluted with ultrapure water, after the abundant derivatization of excessive dinitrofluorobenzene solution is added, then sample introduction is analyzed.
Embodiment 1
2808.8g 25wt% solution of sodium bisulfite is placed in 10L reaction kettle, maintains reactor temperature at 25 DEG C,
And 7gSn-beta catalyst is added into kettle, it is uniformly mixed, 300g ethylene oxide is then slowly passed through into reaction kettle, has been led to
After ethylene oxide, it is further continued for reaction 15min, sampling analysis, the yield of step reaction is 99.5%；Then to being added in reaction kettle
A certain amount of pure water near sodium isethionate concentration dilution to 15.0wt%, will be subsequently passed a certain amount of liquefied ammonia, make liquid in system
Ammonia density reaches 24.0wt%, and 1.0g (0.1wt%) NaBiO is then added3Catalyst and 1.0gCuCl co-catalyst, will react
System is warming up to 160 DEG C, system pressure 9.8MPa, reacts 30min, the sodium taurocholate yield 92.5% that ammonolysis reaction obtains.
Reaction solution is after 100 DEG C of flash distillations are except ammonia, by being concentrated by evaporation, by sodium taurocholate concentration concentrate to 40wt%, then in 80 DEG C of items
The a certain amount of concentrated sulfuric acid is added under part, system pH is adjusted to 7.8, is then cooled to 20 DEG C of crystallizations, taurine one-way yield after crystallization
It is 75.0%, mother liquor can be applied to ammonolysis reaction completely, and applying rear taurine total recovery is 95.0%.
Embodiment 2
2006.3g 35wt% solution of sodium bisulfite is placed in 10L reaction kettle, maintains reactor temperature at 40 DEG C,
And 10.5gSn-beta catalyst is added into kettle, it is uniformly mixed, 300g ethylene oxide is then slowly passed through into reaction kettle, lead to
After complete ethylene oxide, it is further continued for reaction 30min, sampling analysis, the yield of step reaction is 99.7%；Add then in reaction kettle
Enter a certain amount of pure water, in system near sodium isethionate concentration dilution to 15.0wt%, a certain amount of liquefied ammonia will be subsequently passed, made
Liquefied ammonia concentration reaches 21.0wt%, and 2.0g (0.2wt%) NH is then added4BiO3Catalyst and with 1.0gCuCl co-catalyst, will
Reaction system is heated to 140 DEG C, system pressure 7.2MPa, reacts 20min, which reacts obtainable sodium taurocholate yield
89.0%.Reaction solution, by being concentrated by evaporation, sodium taurocholate concentration concentrate to 38wt% then exists after 100 DEG C of flash distillations are except ammonia
The a certain amount of concentrated sulfuric acid is added under the conditions of 60 DEG C, system pH is adjusted to 8.2, is then cooled to 30 DEG C of crystallizations, taurine list after crystallization
Journey yield is 70.0%, and mother liquor can be applied to ammonolysis reaction again, and applying rear taurine total recovery is 90.9%.
Embodiment 3
2340.6g 30wt% solution of sodium bisulfite is placed in 10L reaction kettle, maintains reactor temperature at 30 DEG C,
And 17.5gSn-beta catalyst is added into kettle, it is uniformly mixed, 300g ethylene oxide is then slowly passed through into reaction kettle, lead to
After complete ethylene oxide, it is further continued for reaction 30min, sampling analysis, the yield of step reaction is 99.4%；Add then in reaction kettle
Enter a certain amount of pure water, in system near sodium isethionate concentration dilution to 15.0wt%, a certain amount of liquefied ammonia will be subsequently passed, made
Liquefied ammonia concentration reaches 18.0wt%, and 0.5g (0.05wt%) LiBiO is then added3Catalyst and 0.4gCuCl co-catalyst, will
Reaction system is heated to 120 DEG C, system pressure 5.1MPa, reacts 60min, which reacts obtainable sodium taurocholate yield
95.0%.Reaction solution, by being concentrated by evaporation, sodium taurocholate concentration concentrate to 35wt% then exists after 100 DEG C of flash distillations are except ammonia
The a certain amount of concentrated sulfuric acid is added under the conditions of 90 DEG C, system pH is adjusted to 7, is then cooled to 20 DEG C of crystallizations, taurine one way after crystallization
Yield is 73.2%, and mother liquor can be applied to ammonolysis reaction again, and applying rear taurine total recovery is 93.5%.
Embodiment 4
2340.2g 30wt% solution of sodium bisulfite is placed in 10L reaction kettle, maintains reactor temperature at 35 DEG C,
And 14.0gSn-beta catalyst is added into kettle, it is uniformly mixed, 300g ethylene oxide is then slowly passed through into reaction kettle, lead to
After complete ethylene oxide, it is further continued for reaction 30min, sampling analysis, the yield of step reaction is 99.6%；Add then in reaction kettle
Enter a certain amount of pure water, in system near sodium isethionate concentration dilution to 15.0wt%, a certain amount of liquefied ammonia will be subsequently passed, made
Liquefied ammonia concentration reaches 22.0wt%, and 0.5g (0.5wt%) KBiO is then added3Catalyst and 0.45gCuCl co-catalyst, will be anti-
It answers system to be heated to 150 DEG C, system pressure 8.0MPa, reacts 40min, which reacts obtainable sodium taurocholate yield
93.0%.Reaction solution, by being concentrated by evaporation, sodium taurocholate concentration concentrate to 40wt% then exists after 100 DEG C of flash distillations are except ammonia
The a certain amount of concentrated sulfuric acid is added under the conditions of 50 DEG C, system pH is adjusted to 7.1, is then cooled to 40 DEG C of crystallizations, taurine list after crystallization
Journey yield is 71.9%, and mother liquor can be applied to ammonolysis reaction again, and applying rear taurine total recovery is 92.3%.
Claims (10)
1. a kind of method for preparing taurine, which comprises the following steps: ethylene oxide and sodium hydrogensulfite are non-equal
Sodium isethionate is prepared in reaction under phase catalyst catalytic action, and then sodium isethionate and ammonia are in bismuthic acid salt catalyst
Taurine is prepared in the lower reaction of catalysis.
2. a kind of method for preparing taurine, which comprises the following steps:
(1) ethylene oxide reacts under heterogeneous catalysis catalysis with solution of sodium bisulfite, and it is water-soluble to obtain sodium isethionate
Liquid；
(2) liquefied ammonia is passed through into isethionic acid sodium water solution；
(3) bismuthates homogeneous catalyst is added to being passed through in the isethionic acid aqueous solution after liquefied ammonia, obtains material liquid；
(4) after material liquid is heated, into being reacted to obtain reaction solution in high-pressure reactor；
(5) for reaction solution except neutralizing after ammonia, crystallization obtains taurine product.
3. according to the method described in claim 2, wherein, the concentration of step (1) sulfite hydrogen sodium in aqueous solution is 10-
40wt%, preferably 15-35wt%, more preferably 25-35wt%；And/or
The molar ratio of step (1) ethylene oxide and sodium hydrogensulfite be 0.9:1~1.5:1, preferably 0.95:1~1.2:1,
More preferably 0.99:1~1.01:1.
4. according to the method in claim 2 or 3, wherein heterogeneous catalysis is molecular sieve catalyst H- in step (1)
One of Beta (12.5), dealuminzation De-Al-Beta (12.5) and modified Sn-Beta (12.5) or a variety of, preferably H-
Beta (12.5) and Sn-Beta (12.5), more preferably Sn-Beta (12.5)；And/or
The additional amount of heterogeneous catalysis is the 0.5-5wt%, preferably 1.0- of sodium hydrogensulfite additional amount in step (1)
3.0wt%, more preferably 1.0-2.5wt%.
5. the method according to any one of claim 2-4, wherein step (1) reaction temperature is 10-70 DEG C, preferably
20-50 DEG C, more it is selected as 25-40 DEG C；And/or
Step (1) reaction time is 5-50min, and preferably 10-40min is more selected as 15-30min.
6. the method according to any one of claim 2-5, wherein liquefied ammonia is water-soluble in sodium isethionate in step (2)
Concentration in liquid is 10-30wt%, preferably 15-28wt%, more preferably 18-26wt%.
7. the method according to any one of claim 2-6, wherein the homogeneous metallic catalyst of bismuthates is in step (3)
One of sodium bismuthate, bismuthic acid ammonium, bismuthic acid potassium, bismuthic acid lithium or bismuthic acid calcium are a variety of, preferably sodium bismuthate, bismuthic acid ammonium, bismuthic acid potassium or
One of bismuthic acid lithium；And/or
The dosage of the homogeneous metallic catalyst of bismuthates is the 0.01-10wt% of sodium isethionate quality in step (3), preferably
0.05-5.0wt%, more preferably in 0.05-0.5wt%.
8. the method according to any one of claim 2-7, wherein sodium isethionate and ammonia reacts in step (3)
With or without the use of co-catalyst, it is preferable to use co-catalyst；Co-catalyst is stannous chloride, in ammonium chloride, ammonium bisulfite
One or more, preferred stannous chloride；And/or the mass ratio of co-catalyst and bismuthic acid salt catalyst is 0.1:1~1.5:1,
Preferably 0.3:1~1.0:1, more preferably in 0.5:1~1.0:1.
9. the method according to any one of claim 2-8, wherein the reaction temperature of step (4) is 50-220 DEG C, preferably
It is 80-200 DEG C, more preferably 120-160 DEG C；The reaction pressure of step (3) be 0.1-12MPa, preferably 1-10MPa, it is more excellent
It is selected as 5-10MPa (gauge pressure)；Reaction time in step (3) is 5-120min, preferably 10-80min, more preferably 20-
60min。
10. the method according to any one of claim 2-9, wherein after step (5) reaction solution removes ammonia, existed with the concentrated sulfuric acid
It is neutralized at 50-90 DEG C and system pH is adjusted between 7-9；And/or it is cooled to 20-40 DEG C of crystallization after step (5) neutralization, it obtains
Taurine product.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110452136A (en) * | 2019-07-10 | 2019-11-15 | 湖北远大生命科学与技术有限责任公司 | A method of preparing taurine |
| CN113061101A (en) * | 2020-01-02 | 2021-07-02 | 万华化学集团股份有限公司 | Synthetic method of N-methyl sodium taurate |
| CN113788770A (en) * | 2021-10-21 | 2021-12-14 | 江阴华昌食品添加剂有限公司 | Method for producing taurine by using ethylene oxide |
| CN116143665A (en) * | 2022-12-31 | 2023-05-23 | 江阴华昌食品添加剂有限公司 | Low-pressure ammonolysis method of sodium taurine |
| CN116253668A (en) * | 2023-05-12 | 2023-06-13 | 广州天赐高新材料股份有限公司 | Preparation method of sodium hydroxyalkyl sulfonate |
-
2018
- 2018-12-11 CN CN201811512124.2A patent/CN109485586A/en not_active Withdrawn
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110452136A (en) * | 2019-07-10 | 2019-11-15 | 湖北远大生命科学与技术有限责任公司 | A method of preparing taurine |
| CN113061101A (en) * | 2020-01-02 | 2021-07-02 | 万华化学集团股份有限公司 | Synthetic method of N-methyl sodium taurate |
| CN113061101B (en) * | 2020-01-02 | 2023-01-13 | 万华化学集团股份有限公司 | Synthetic method of N-methyl sodium taurate |
| CN113788770A (en) * | 2021-10-21 | 2021-12-14 | 江阴华昌食品添加剂有限公司 | Method for producing taurine by using ethylene oxide |
| CN116143665A (en) * | 2022-12-31 | 2023-05-23 | 江阴华昌食品添加剂有限公司 | Low-pressure ammonolysis method of sodium taurine |
| CN116253668A (en) * | 2023-05-12 | 2023-06-13 | 广州天赐高新材料股份有限公司 | Preparation method of sodium hydroxyalkyl sulfonate |
| CN116253668B (en) * | 2023-05-12 | 2023-07-07 | 广州天赐高新材料股份有限公司 | Preparation method of sodium hydroxyalkyl sulfonate |
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Application publication date: 20190319 |