CN102408360A - Preparation method of taurine - Google Patents
Preparation method of taurine Download PDFInfo
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- CN102408360A CN102408360A CN2011104354590A CN201110435459A CN102408360A CN 102408360 A CN102408360 A CN 102408360A CN 2011104354590 A CN2011104354590 A CN 2011104354590A CN 201110435459 A CN201110435459 A CN 201110435459A CN 102408360 A CN102408360 A CN 102408360A
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- taurine
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- hydrogen peroxide
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Abstract
The invention discloses a preparation method of taurine. The method comprises the following steps: using 2-aminoethanesulfinic acid and hydrogen peroxide to perform an oxidation reaction at a certain reaction pressure, thus obtaining a taurine reaction solution; and cooling, performing centrifugal separation, washing and drying to prepare the taurine finished product. The preparation method has the advantages of fewer reaction steps and short time; and three wastes can not be generated in the entire production process, the production environment is good, the yield and quality of the product are high and the method is an ideal environmentally-friendly technology.
Description
Technical field
The present invention relates to the organic chemistry synthesis technical field, be specifically related to a kind of preparation method of taurine.
Background technology
Taurine (Taurine) claim taurocholic acid again; It is a kind of sulfur-bearing nonprotein amino acid; Chemistry 2-aminoethyl sulfonic acid by name; Being a kind of sulfur-containing amino acid with different physiological roles that exists in the human body, having effects such as the brain development of promotion, vision enhancing, anti-inflammatory, analgesic, hypotensive, hypoglycemic, strong liver cholagogic, is one of most important amino acid in the human body.Taurine is colourless, tasteless, and without any side effects, so developed country attaches great importance to its research and application.In recent years along with further investigation to its physiological action, nutritive value; It is very extensive that its application becomes, and taurine in a large number as dietary supplements and foodstuff additive, it is reported abroad; The U.S. and Japan are topmost countries of consumption, and a year consumption reaches 10,000 tons and more than 5,000 ton respectively.
Along with the transfer of world's chemical industry, China has become maximum and main taurine producing country and the export State in the whole world, and the taurine ultimate production is about 20,000 tons in the time of 2000, and 2008 gross annual output amounts are about 3.38 ten thousand tons, and export volume in 2010 is above 40,000 tons; 90% outlet of China's taurine is America and Europe and South East Asia main purpose, and export volume increases year by year; Along with the raising of China's living standards of the people, domestic demand to taurine also increases gradually, if the consumption of China's taurine reaches the half the of American-European countries, with the year demand that increases at least 4 ten thousand tons.The taurine industrial chain develops rapidly, and downstream deep processing industry increases the demand of taurine day by day, and the process modification of research taurine has important economy and social effect to industry development.
Taurine is since finding, people are just constantly exploring the approach of its synthetic.So far, the compound method of relevant taurine is not descended tens of kinds.Obtain the taurine chemical synthesis at present and mainly contain dichloroethane law, epoxyethane method, esterification alkaline hydrolysis conversion ethyleneimine method and thanomin esterification reduction method etc.Dichloroethane law and epoxyethane method since wherein process need under HTHP, react with liquefied ammonia, equipment manufacturing cost height, process management are difficult, the reaction process side reaction is more; And the esterification alkaline hydrolysis transforms ethyleneimine method employing thanomin and strong sulfuric acid response generates sulfuric ester, adds liquid caustic soda (NaOH) heating again and generates ethyleneimine, and the ethyleneimine that makes is produced taurine with sulfurous gas or ammonium bisulfite reaction again; In this process; Because ethyleneimine is highly toxic product, when producing and use, will take tight safeguard procedures, and above-mentioned reaction intermediate steps is many; Raw material is wasteful; Cost is high, and particularly the gas-liquid of sulfurous gas and ethyleneimine should be the very exothermic reaction on the contrary, brings difficulty to suitability for industrialized production.
At present, the technology of taurine comparative maturity is thanomin esterification reduction method both at home and abroad, and it is raw material with the monoethanolamine, and through esterification, reduction reaction synthesized taurine, this reaction raw materials is easy to get, and yield is high than additive method, its reaction formula:
This method is divided into following a few step again in the actual industrial process:
(1) salify:
(2) esterification:
(3) reduction:
In above-mentioned three-step reaction, following side reaction is arranged:
(1) hydrolysis of ester:
(2) the intermolecular dehydration of ester:
(3) Na
2SO
3Oxidation:
(4) Na
2SO
3Hydrolysis:
No matter the thanomin sulfuric ester still all is prone to hydrolytic reactions at alkaline environment at sour environment, for this reason, will above-mentioned acidulants be adjusted to neutrality (pH=7) before the reduction reaction.Existing many producers (comprising the laboratory) all adopt soda ash (Na
2CO
3) the solution adjusting, reaction formula:
Na
2CO
3?+?H
2SO
4?→?Na
2SO
4?+?CO
2?↑+?H
2O
This method is difficult control in actual production process, is difficult to accurately measure potential of hydrogen, and technology is very unstable, makes soda ash excessive easily, and in aftertreatment technology, adopts while hot that suction filtration desalts more, because Na
2SO
3, Na
2SO
4Very easily bond, separating of taurine and inorganic salt is difficult to reach the ideal effect, and yield is merely 48-52% in the whole process, and the cost yield is merely 49%, and production cost is high, and energy consumption is big, and labour intensity is big.
Summary of the invention
The technical problem that the present invention mainly solves provides a kind of simple and easy to do, economical, not only peaceful but also can realize cleaning the preparation method of the taurine of production.
For solving the problems of the technologies described above; The technical scheme that the present invention adopts is: a kind of preparation method of taurine; Oxidizing reaction is taken place in 2-ethylamine-sulfinic acid and hydrogen peroxide obtain the taurine reaction solution under certain reaction pressure, through cooling, spinning; Washing and oven dry make the taurine finished product.
In preferred embodiment of the present invention, the mass percent concentration of described 2-ethylamine-sulfinic acid is any concentration.
In preferred embodiment of the present invention, the mass percent concentration of described 2-ethylamine-sulfinic acid is 40～50%.
In preferred embodiment of the present invention, the mass percent concentration of described hydrogen peroxide is any concentration.
In preferred embodiment of the present invention, the mass percent concentration of described hydrogen peroxide is 27.5～50%.
In preferred embodiment of the present invention, the mol ratio of described 2-ethylamine-sulfinic acid and hydrogen peroxide is 1:1～2.
In preferred embodiment of the present invention, the mol ratio of described 2-ethylamine-sulfinic acid and hydrogen peroxide is 1:1.4～1.6.
In preferred embodiment of the present invention, the reaction conditions of described oxidizing reaction is: temperature of reaction is 40～100 ℃, and the reaction times is 12～24h.
In preferred embodiment of the present invention, the reaction conditions of described oxidizing reaction is: temperature of reaction is 60～80 ℃, and the reaction times is 16～20h.
In preferred embodiment of the present invention, described reaction pressure is 0.01～0.1MPa.
The present invention is owing to adopt technique scheme, and 2-ethylamine-sulfinic acid and one step of ydrogen peroxide 50 generation redox reaction make taurine, and reactions step is few; Reaction times is short, simultaneously because byproduct of reaction is a water, does not have other sub product generation in the whole process and needn't use the employing activated carbon decolorizing; Generating taurine also needn't be through crystallization impurity elimination again, and transformation efficiency is high, can reach more than 90%; Do not produce " three wastes " in the whole process of production; Production environment is good, and the yield of product and quality are high, are the ideal green environment-protective process.
Embodiment
Chemical equation of the present invention is following:
Oxidizing reaction takes place with 2-ethylamine-sulfinic acid and hydrogen peroxide and obtains the taurine reaction solution in a kind of preparation method of taurine under certain reaction pressure, through cooling, and spinning, washing and oven dry make the taurine finished product.
Wherein, the mass percent concentration of described 2-ethylamine-sulfinic acid is any concentration, and preferred mass percent concentration is 40～50%; The mass percent concentration of described hydrogen peroxide is any concentration, and preferred mass percent concentration is 27.5～50%; The mol ratio of described 2-ethylamine-sulfinic acid and hydrogen peroxide is 1:1～2, and preferred molar ratio is 1:1.4～1.6; The reaction conditions of described oxidizing reaction is: temperature of reaction is 40～100 ℃, and the reaction times is 12～24h; Preferred reaction conditions is: temperature of reaction is 60～80 ℃, and the reaction times is 16～20h; Described reaction pressure is 0.01～0.1MPa.
Embodiment 1
218.4g (50.0%) the 2-ethylamine-sulfinic acid aqueous solution is joined 1000 milliliters of bands stir, in the stainless steel autoclave of cooling and heating unit, under agitation, add 27.5% aqueous hydrogen peroxide solution 247.2g from charging opening; Controlled temperature is at 70 ℃, and pressure is 0.08 MPa, insulation reaction 18h; Stop heating, be cooled to 8 ℃, filter; And with 100 ml water washing leaching cakes, dry cake gets the pure article 116.2g of taurine.The taurine yield is 92.8%, and purity is 99.04%.
Embodiment 2
218.4g (50.0%) the 2-ethylamine-sulfinic acid aqueous solution is joined 1000 milliliters of bands stir, in the stainless steel autoclave of cooling and heating unit, under agitation, add 27.5% aqueous hydrogen peroxide solution 123.6g from charging opening; Controlled temperature is at 60 ℃, and pressure is 0.02 MPa, insulation reaction 20h; Stop heating, be cooled to 8 ℃, filter; And with 100 ml water washing leaching cakes, dry cake gets the pure article 114.2g of taurine.The taurine yield is 91.2%, and purity is 99.45%.
Embodiment 3
218.4g (50.0%) the 2-ethylamine-sulfinic acid aqueous solution is joined 1000 milliliters of bands stir, in the stainless steel autoclave of cooling and heating unit, under agitation, add 27.5% aqueous hydrogen peroxide solution 185.4g from charging opening; Controlled temperature is at 80 ℃, and pressure is 0.04 MPa, insulation reaction 16h; Stop heating, be cooled to 8 ℃, filter; And with 100 ml water washing leaching cakes, dry cake gets the pure article 118.2g of taurine.The taurine yield is 94.4%, and purity is 99.67%.
Embodiment 4
218.4g (50.0%) the 2-ethylamine-sulfinic acid aqueous solution is joined 1000 milliliters of bands stir, in the stainless steel autoclave of cooling and heating unit, under agitation, add 27.5% aqueous hydrogen peroxide solution 173.0g from charging opening; Controlled temperature is at 70 ℃, and pressure is 0.04 MPa, insulation reaction 20h; Stop heating, be cooled to 8 ℃, filter; And with 100 ml water washing leaching cakes, dry cake gets the pure article 115.4g of taurine.The taurine yield is 92.2%, and purity is 99.24%.
Embodiment 5
218.4g (50.0%) the 2-ethylamine-sulfinic acid aqueous solution is joined 1000 milliliters of bands stir, in the stainless steel autoclave of cooling and heating unit, under agitation, add 27.5% aqueous hydrogen peroxide solution 197.8g from charging opening; Controlled temperature is at 40 ℃, and pressure is 0.05 MPa, insulation reaction 24h; Stop heating, be cooled to 8 ℃, filter; And with 100 ml water washing leaching cakes, dry cake gets the pure article 112.9g of taurine.The taurine yield is 90.2%, and purity is 99.66%.
Embodiment 6
218.4g (50.0%) the 2-ethylamine-sulfinic acid aqueous solution is joined 1000 milliliters of bands stir, in the stainless steel autoclave of cooling and heating unit, under agitation, add 50.0% aqueous hydrogen peroxide solution 117g from charging opening; Controlled temperature is at 70 ℃, and pressure is 0.04 MPa, insulation reaction 18h; Stop heating, be cooled to 8 ℃, filter; And with 100 ml water washing leaching cakes, dry cake gets the pure article 113.8g of taurine.The taurine yield is 90.9%, and purity is 99.43%.
Embodiment 7
273g (40.0%) the 2-ethylamine-sulfinic acid aqueous solution is joined 1000 milliliters of bands stir, in the stainless steel autoclave of cooling and heating unit, under agitation, add 50.0% aqueous hydrogen peroxide solution 117g from charging opening; Controlled temperature is at 75 ℃, and pressure is 0.045MPa, insulation reaction 20h; Stop heating, be cooled to 8 ℃, filter; And with 100 ml water washing leaching cakes, dry cake gets the pure article 116.8g of taurine.The taurine yield is 93.3%, and purity is 99.78%.
Embodiment 8
242.2g (45.0%) the 2-ethylamine-sulfinic acid aqueous solution is joined 1000 milliliters of bands stir, in the stainless steel autoclave of cooling and heating unit, under agitation, add 40.0% aqueous hydrogen peroxide solution 127.5g from charging opening; Controlled temperature is at 75 ℃, and pressure is 0.035MPa, insulation reaction 21h; Stop heating, be cooled to 8 ℃, filter; And with 100 ml water washing leaching cakes, dry cake gets the pure article 114.6g of taurine.The taurine yield is 91.5%, and purity is 99.62%.
The above is merely embodiments of the invention; Be not so limit claim of the present invention; Every equivalent structure or equivalent flow process conversion that utilizes specification sheets of the present invention to do, or directly or indirectly be used in other relevant technical fields, all in like manner be included in the scope of patent protection of the present invention.
Claims (10)
1. the preparation method of a taurine is characterized in that, oxidizing reaction is taken place in 2-ethylamine-sulfinic acid and hydrogen peroxide obtain the taurine reaction solution under certain reaction pressure, and through cooling, spinning, washing and oven dry make the taurine finished product.
2. the preparation method of taurine according to claim 1 is characterized in that, the mass percent concentration of described 2-ethylamine-sulfinic acid is any concentration.
3. the preparation method of taurine according to claim 2 is characterized in that, the mass percent concentration of described 2-ethylamine-sulfinic acid is 40～50%.
4. the preparation method of taurine according to claim 1 is characterized in that, the mass percent concentration of described hydrogen peroxide is any concentration.
5. the preparation method of taurine according to claim 4 is characterized in that, the mass percent concentration of described hydrogen peroxide is 27.5～50%.
6. the preparation method of taurine according to claim 1 is characterized in that, the mol ratio of described 2-ethylamine-sulfinic acid and hydrogen peroxide is 1:1～2.
7. the preparation method of taurine according to claim 6 is characterized in that, the mol ratio of described 2-ethylamine-sulfinic acid and hydrogen peroxide is 1:1.4～1.6.
8. the preparation method of taurine according to claim 1 is characterized in that, the reaction conditions of described oxidizing reaction is: temperature of reaction is 40～100 ℃, and the reaction times is 12～24h.
9. the preparation method of taurine according to claim 8 is characterized in that, the reaction conditions of described oxidizing reaction is: temperature of reaction is 60～80 ℃, and the reaction times is 16～20h.
10. the preparation method of taurine according to claim 8 is characterized in that, described reaction pressure is 0.01～0.1MPa.
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| CN2011104354590A CN102408360A (en) | 2011-12-23 | 2011-12-23 | Preparation method of taurine |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112479944A (en) * | 2020-12-02 | 2021-03-12 | 浙江新和成股份有限公司 | Taurine and its recrystallization method |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101260070A (en) * | 2008-04-21 | 2008-09-10 | 常熟市虞东化工有限公司 | Method for preparing taurine |
| CN101508657A (en) * | 2008-02-14 | 2009-08-19 | 王代龙 | Synthesis of taurine |
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2011
- 2011-12-23 CN CN2011104354590A patent/CN102408360A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101508657A (en) * | 2008-02-14 | 2009-08-19 | 王代龙 | Synthesis of taurine |
| CN101260070A (en) * | 2008-04-21 | 2008-09-10 | 常熟市虞东化工有限公司 | Method for preparing taurine |
Non-Patent Citations (2)
| Title |
|---|
| 《Journal of Chromatography》 19941003 Shinya Futani等 "High performance liquid chromatographic determination of hypotaurine and taurine after conversion to 4-dimethylaminoazobenzene-4-sulfonyl derivatives and its application to the urine of cysteine administered rats" 第167页, 第3段 1-10 第660卷, * |
| SHINYA FUTANI等: ""High performance liquid chromatographic determination of hypotaurine and taurine after conversion to 4-dimethylaminoazobenzene-4-sulfonyl derivatives and its application to the urine of cysteine administered rats"", 《JOURNAL OF CHROMATOGRAPHY》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112479944A (en) * | 2020-12-02 | 2021-03-12 | 浙江新和成股份有限公司 | Taurine and its recrystallization method |
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Application publication date: 20120411 |