CN111689880B - Method for preparing taurine from sodium isethionate - Google Patents

Method for preparing taurine from sodium isethionate Download PDF

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CN111689880B
CN111689880B CN202010667234.7A CN202010667234A CN111689880B CN 111689880 B CN111689880 B CN 111689880B CN 202010667234 A CN202010667234 A CN 202010667234A CN 111689880 B CN111689880 B CN 111689880B
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taurate
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palladium
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CN111689880A (en
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郭云峰
张静
桂振友
蔺海政
李建锋
郭斌
郑兵
孔令晓
陈来中
张永振
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Wanhua Chemical Group Co Ltd
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    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
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    • 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
    • C07C303/04—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 by substitution of hydrogen atoms by sulfo or halosulfonyl groups
    • C07C303/06—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 by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
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Abstract

The invention provides a method for preparing taurine from sodium isethionate, which adopts Pd-C/Al with a shape selection function2O3The heterogeneous catalyst efficiently catalyzes the ammonolysis reaction of the hydroxyethyl sodium sulfonate, and then the taurine product is obtained through the steps of neutralization, crystallization, separation and the like. Compared with the traditional alkaline catalyst, the catalyst used in the invention can limit the generation of macromolecular byproducts of sodium disubstituted taurate and sodium trisubstituted taurate through the unique pore channel structure, thereby improving the selectivity of the sodium taurate in the ammonolysis reaction, simultaneously, the excellent catalytic performance of the catalyst effectively reduces the temperature and the pressure of the ammonolysis reaction, shortens the reaction time, and can be separated and recycled through simple filtration.

Description

Method for preparing taurine from sodium isethionate
Technical Field
The invention belongs to the field of preparation of taurine, and particularly relates to a method for preparing taurine with high selectivity by using sodium isethionate.
Background
Taurine, also known as 2-aminoethanesulfonic acid, is a sulfur-containing, non-protein amino acid having the following structure:
Figure BDA0002580812840000011
taurine molecular formula
The chemical synthesis method of taurine mainly comprises an ethanolamine method and an ethylene oxide method. The ethanolamine method has the disadvantages of long reaction period, high production cost and the like, and the technology is gradually eliminated. The ethylene oxide method takes ethylene oxide and liquid ammonia as raw materials, and the raw materials are cheap and easy to obtain, so that the method has obvious cost advantage compared with an ethanolamine method, and the reaction yield is slightly higher than that of the ethanolamine method. Based on the above advantages, the ethylene oxide method has become the mainstream process for producing taurine at present.
The key synthesis step of the ethylene oxide method is that sodium isethionate and liquid ammonia are subjected to ammonolysis reaction to prepare sodium taurate, in the initial research, no catalyst is added, and severe reaction conditions of high temperature of 200-280 ℃ and high pressure of 14-21MPa are required, so that the energy consumption of the reaction process is high, the production cost is high, the selectivity of the main product sodium taurate of the ammonolysis reaction is only 71%, and meanwhile, more disubstituted sodium taurate and trisubstituted sodium taurate are generated as byproducts (as disclosed in German patent DD 219023A 3), and the conversion rate of the raw material sodium isethionate is less than 97%, so that the single-pass yield of the reaction is less than 69%. Therefore, the sodium taurate is an important intermediate for preparing the taurine by the ethylene oxide method, and the yield and the purity of the sodium taurate are determined by the conversion rate and the selectivity of the sodium isethionate for producing the sodium taurate through the ammonolysis reaction.
Chinese patent CN105732440A discloses that sodium carbonate, potassium carbonate, iron-based/aluminum-based metal salt and NiO/CeO are added in the ammonolysis reaction process for mother liquor2Rare earth oxides, etcAny one or the combination of the catalysts is used as the catalyst, and the yield of the sodium taurate can be improved to 90-95% after recycling, but the once-through yield is not mentioned, and in addition, the reaction conditions are still harsh, the reaction temperature is 255-265 ℃ and the reaction pressure is 19-20 MPa.
U.S. Pat. No. 3, 20160355470, 1 discloses that NaOH is added to the aminolysis reaction of sodium isethionate to catalyze the aminolysis reaction to proceed toward the formation of sodium taurate, the aminolysis reaction can obtain a yield of sodium taurate of 90% or more, but the by-products of the aminolysis reaction are still more, and the reaction still requires the harsh conditions of high temperature of 160-.
In view of the above, there is a need for a more efficient method for preparing sodium taurate, so as to improve the yield and purity of sodium taurate product, and simultaneously make the reaction conditions as mild as possible, so as to reduce the energy consumption in the production process and the production cost.
Disclosure of Invention
The invention aims to provide a method for preparing Pd-C/Al with a shape selection function2O3The catalyst used in the method can limit the generation of macromolecular byproducts (di-substituted sodium taurate and tri-substituted sodium taurate) through the unique pore channel structure of the catalyst, so that the selectivity of the sodium taurate in the ammonolysis reaction is improved, the excellent catalytic performance of the catalyst effectively reduces the temperature and pressure of the ammonolysis reaction, the reaction time is shortened, and the catalyst can be separated and recycled through simple filtration.
The method has the advantages of mild process conditions (low temperature and low pressure), short reaction time, high conversion rate (the conversion rate of the sodium isethionate in the ammonolysis reaction is more than or equal to 98 percent), high single-pass yield of the sodium taurate (the yield of the sodium taurate in the ammonolysis reaction can reach 90.0-96.0 percent) and the like.
In order to achieve the above purpose, the technical scheme provided by the invention is as follows:
a method for preparing taurine from sodium isethionate is carried out by reacting sodium isethionate with ammonia in Pd-C/Al2O3Form selectionPreparing taurine in the presence of a catalyst.
In the present invention, the Pd-C/Al2O3The shape-selective catalyst is prepared by taking sodium taurate as a template, adding organic aluminum salt into an ethanol water solution for hydrolysis reaction, adding palladium salt into a hydrolysis reaction system, and roasting a product after the hydrolysis reaction in a nitrogen atmosphere.
In some embodiments of the invention, the Pd-C/Al2O3The preparation method of the shape-selective catalyst comprises the following steps:
(1) dissolving sodium taurate in aqueous solution of ethanol, and then adding organic aluminum salt and palladium salt into the aqueous solution to perform hydrolysis reaction;
(2) separating solid from the reaction liquid in the step (1), drying, and roasting in a nitrogen environment to obtain Pd-C/Al2O3And (4) selecting a catalyst.
Further, in the step (1), the mass fraction of ethanol in the ethanol aqueous solution is 10-85 wt%, preferably 30-70 wt%, and more preferably 65-70 wt%;
the concentration of the sodium taurate in the ethanol water solution is 0.1-1.5 wt%, preferably 0.5-0.8 wt%;
the molar ratio of the organic aluminum salt to the sodium taurate is 10-24: 1, preferably 15 to 17: 1;
the molar ratio of the palladium salt to the organic aluminum salt is 0.01-0.07: 1, preferably 0.03 to 0.05: 1.
further, in the step (1), the hydrolysis reaction is carried out at the temperature of 20-80 ℃, preferably at the temperature of 30-45 ℃, and more preferably at the temperature of 30-33 ℃; the reaction time is 0.5 to 10 hours, preferably 3 to 8 hours, more preferably 4 to 6 hours.
Further, in the step (2), the drying temperature is 80-120 ℃, preferably 100-120 ℃, and the time is 2-6h, preferably 3-4 h; the roasting temperature is 350-500 ℃, preferably 400-450 ℃, the roasting time is 5-10h, preferably 6-8h, N2The pressure is normal pressure (0.1 MPa).
Further, in the step (1), the organic aluminum salt is one or more of aluminum isopropoxide, aluminum sec-butoxide and aluminum tert-butoxide, preferably aluminum isopropoxide and/or aluminum sec-butoxide;
the palladium salt is one or more of palladium chloride, palladium acetate, palladium nitrate, tetraamminepalladium dichloride, palladium sulfate and ethylenediamine palladium sulfate, and preferably palladium chloride and/or palladium nitrate.
Preferably, in particular embodiments, the Pd-C/Al2O3The shape-selective catalyst can be prepared by the following method: adding sodium taurate into ethanol water solution, adding organic aluminum salt, stirring at room temperature (such as about 25 ℃), adding palladium salt, maintaining the room temperature, continuing to stir uniformly, then carrying out hydrolysis reaction at 20-80 ℃ for 0.5-10h, filtering after the reaction is finished, collecting precipitate, washing with water, drying at 80-120 ℃ for 2-6h, then placing in a nitrogen roasting furnace for roasting at 350-500 ℃ for 5-10h, and Pd-C/Al2O3And (4) selecting a catalyst.
The method for preparing taurine from sodium isethionate provided by the invention comprises the following steps:
1) adding liquid ammonia and Pd-C/Al into the water solution of the hydroxyethyl sodium sulfonate2O3Carrying out ammonolysis reaction on a shape-selective catalyst to obtain a reaction solution containing sodium taurate;
2) removing ammonia from the reaction liquid obtained in the step 1), and then neutralizing and crystallizing to obtain the taurine.
In the method, in the step 1), the concentration of the sodium isethionate aqueous solution is 10 to 35 wt%, preferably 15 to 25 wt%, and more preferably 15 to 18 wt%;
the concentration of the liquid ammonia in the reaction system is 10-30 wt%, preferably 15-27 wt%, and more preferably 18-23 wt%;
the Pd-C/Al2O3The selective catalyst is used in an amount of 0.5 to 8 wt%, preferably 1.0 to 4.0 wt%, more preferably 1.2 to 2.0 wt% of the sodium isethionate.
In the method, in the step 1), the ammonolysis reaction is carried out at the reaction temperature of 40-210 ℃, preferably 90-200 ℃ and more preferably 130-150 ℃;
the reaction pressure is 0.1-15MPa, preferably 2-10MPa, more preferably 5-9MPa, and if not specifically stated, the pressures are gauge pressures;
the reaction time is 10-120min, preferably 10-80min, more preferably 20-60 min.
In the method, step 2) is preferably a flash evaporation ammonia removal method, excess ammonia generated in the ammonolysis reaction in step 1) is removed by flash evaporation, and evaporation concentration is carried out, so that the concentration of the sodium taurate is increased to 36-41 wt%, preferably 37-39 wt%.
In the method, concentrated sulfuric acid is preferably adopted for neutralization in the step 2), and the concentration of the concentrated sulfuric acid is preferably about 98 wt%; the neutralization temperature is 50-90 ℃, preferably 70-80 ℃; adding concentrated sulfuric acid to adjust the pH value of the system to 7-9.
In the method, in the step 2), the crystallization temperature is 20-40 ℃, preferably 25-30 ℃; the time is 2-8h, preferably 4-5 h.
In some embodiments, the taurine preparation of the invention can be carried out by using a high-pressure reaction kettle: putting 10-35 wt% sodium isethionate solution into a high-pressure reaction kettle, introducing liquid ammonia, controlling the ammonia concentration in the system to be 10-30 wt%, and then adding 0.5-8 wt% of Pd-C/Al of sodium isethionate2O3Selecting a catalyst, heating a reaction system to 40-210 ℃, and carrying out ammonolysis reaction for 10-120min under the gauge pressure of 0.1-15MPa to generate sodium taurate; and (3) flashing the reaction solution at 90 ℃ and 60kPa (absolute pressure) to remove excessive ammonia and part of water, concentrating the sodium taurate to 36-41 wt%, adding concentrated sulfuric acid at 50-90 ℃ to adjust the pH of the system to 7-9, cooling to 20-40 ℃, and crystallizing for 2-8 hours to obtain the taurine.
Further, the mother liquor crystallized in the step 2) can be recycled, so that the yield of taurine is improved.
The invention provides Pd-C/Al2O3The shape-selective catalyst is Al (OH) obtained by hydrolyzing sodium taurate serving as a template with an organic aluminum source3The surface of the species has rich hydroxyl groups, the hydroxyl groups and sodium taurate interact through hydrogen bonds, so that aluminum species grow around single sodium taurate, meanwhile, added Pd salt is also loaded on a carrier in the hydrolysis process of an aluminum source, sodium taurate molecules are decomposed after the hydrolysis product is roasted in a nitrogen atmosphere, and the sodium taurate molecules are decomposed on the carrierThe crack pore canal with the size close to that of the sodium taurate is left, when the hydroxyethyl sodium sulfonate and ammonia carry out ammonolysis reaction at the catalytic active site in the pore canal, only the sodium taurate with the size close to that of the pore canal can be generated, and for the larger molecule sodium disubstituted taurate and sodium trisubstituted taurate, the generation of the molecule is limited because the catalyst pore canal with specific size has obvious steric hindrance effect on the molecule, thereby obviously improving the catalytic selectivity of the ammonolysis reaction; meanwhile, sodium taurate can generate carbon species by decomposing at high temperature under nitrogen, and the carbon species and Pd form Pd-C species with higher catalytic activity, and the species can effectively promote electron transfer of sodium isethionate and ammonia on the catalytic center in the ammonolysis reaction process, so that the reaction can be carried out under milder conditions, the reaction time is shortened, and the selectivity of sodium taurate preparation by sodium isethionate is obviously improved.
The invention has the positive effects that:
(1) by Pd-C/Al2O3The special pore channel structure of the shape-selective catalyst limits the generation of macromolecular byproducts in the ammonolysis reaction, remarkably improves the one-way yield of the sodium taurate to 92-96 percent, and remarkably improves the conversion rate of the hydroxyethyl sodium sulfonate to more than 98 percent.
(2) Due to Pd-C/Al2O3The shape-selective catalyst has high-efficiency catalytic activity, so that the reaction condition of the ammonolysis reaction is milder, the reaction temperature and pressure are low, and the ammonolysis reaction time is short.
Detailed Description
The following examples are not intended to limit the scope of the present invention, and modifications and equivalents may be made thereto without departing from the spirit and scope of the present invention, which is defined in the appended claims.
In the examples, the raw materials used are conventional in the art, and the purity specification used is analytical or chemical purity;
first, the raw material source information in each of the following examples:
sodium isethionate, dinitrofluorobenzene, palladium ethylenediamine sulfate, available from Sigma Aldrich trade ltd; ethanol, aluminum isopropoxide, aluminum sec-butoxide, aluminum tert-butoxide, palladium chloride, palladium acetate, palladium nitrate, tetraamminepalladium chloride, palladium sulfate were purchased from Shanghai Aladdin Biotech.
Secondly, the following test method is adopted in each example of the invention:
taurine was analyzed by liquid chromatography equipped with a uv detector, an agilent 1200 series, equipped with a C18 liquid chromatography column, with column temperature set at 40 ℃, in acetonitrile and 0.05mol/L NaH2PO4The solution is a mobile phase, the flow rate is 1.0mL/min, the detection is carried out at the wavelength of 360nm by an ultraviolet detector, and the quantification is carried out by an external standard method. Before sample introduction, a sample is diluted properly by ultrapure water, added with excessive dinitrofluorobenzene solution for full derivatization, and then subjected to sample introduction analysis.
Example 1
Preparation of Pd-C/Al2O3 type-selective catalyst:
adding 3.0g (1.0 wt%) of sodium taurate into 300g of ethanol aqueous solution (68.0 wt%), then adding 80.3g of aluminum sec-butoxide, stirring uniformly at 25 ℃, adding 3.76g of palladium nitrate, keeping the temperature for stirring continuously, and then carrying out hydrolysis reaction at 32 ℃ for 5 hours; then filtering, washing and drying the precipitate for 4h at 100 ℃, and then placing the precipitate in a nitrogen roasting furnace for roasting for 7h at 450 ℃ and normal pressure to obtain the Pd-C/Al2O3And (4) selecting a catalyst.
Preparation of taurine from sodium isethionate:
600g of sodium isethionate solution (23.0 wt.%) was placed in a 1L high-pressure reactor, liquid ammonia was introduced so as to control the ammonia concentration at 21.0 wt.%, and then 2.07g (1.5 wt.%) of the above Pd-C/Al was added2O3And (3) selecting a catalyst, heating a reaction system to 140 ℃, and carrying out ammonolysis reaction under the condition that the system pressure is 8.0MPa of gauge pressure for 50min, wherein the conversion rate of the hydroxyethyl sodium sulfonate is 99.2%, the yield of the obtained sodium taurate is 96.0%, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 96.77%, 2.89% and 0.34% respectively.
Evaporating the reaction solution at 90 ℃ and 60kPa (absolute pressure) to remove excessive ammonia and part of water, concentrating the sodium taurate to 41 wt%, adding 98 wt% concentrated sulfuric acid at 80 ℃ to adjust the pH of the system to 7.8, cooling to 30 ℃ and crystallizing for 5h, wherein the once-through yield of the taurine after crystallization is 80.6%, and the total yield of the taurine after recycling mother solution is 96.0%.
Example 2
Adding 2.1g (0.7 wt%) sodium taurate into 300g ethanol aqueous solution (55.0 wt%), then adding 49.2g aluminum tert-butoxide, stirring uniformly at 25 ℃, adding 1.35g palladium acetate, keeping the temperature and continuing stirring, then carrying out hydrolysis reaction at 20 ℃ for 3h, filtering, washing and drying the precipitate at 120 ℃ for 3h, then placing the precipitate in a nitrogen roasting furnace for roasting at 380 ℃ for 5h to obtain the Pd-C/Al2O3And (4) selecting a catalyst.
600g of sodium isethionate solution (18.0 wt%) was placed in a 1L high-pressure reactor, a certain amount of liquid ammonia was passed through, the ammonia concentration was controlled to 22.0 wt%, and then 1.08g (1.0 wt%) of the above Pd-C/Al was added2O3The catalyst is selected, the reaction system is heated to 180 ℃, the system pressure is 9.0MPa, the reaction is carried out for 70min, the conversion rate of the hydroxyethyl sodium sulfonate in the ammonolysis reaction is 98.9 percent, the yield of the obtained sodium taurate is 94.8 percent, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 95.85 percent, 3.29 percent and 0.86 percent respectively.
Evaporating the reaction solution at 90 ℃ and 60kPa (absolute pressure) to remove excessive ammonia and part of water, concentrating the sodium taurate to 40 wt%, adding 98% concentrated sulfuric acid at 75 ℃ to adjust the pH of the system to 7.9, cooling to 20 ℃ for crystallization for 2h, wherein the once-through yield of taurine after crystallization is 77.6%, and the total yield of taurine after mother solution is recycled is 95.1%.
Example 3
Adding 0.6g (0.2 wt%) of sodium taurate into 300g of ethanol aqueous solution (30.0 wt%), then adding 8.33g of aluminum isopropoxide, stirring uniformly at 25 ℃, adding 0.07g of palladium chloride, keeping the temperature for continuous stirring, then carrying out hydrolysis reaction at 45 ℃ for 1h, filtering and washing the precipitate, drying at 80 ℃ for 2h, then placing the precipitate in a nitrogen roasting furnace for roasting at 400 ℃ for 6h to obtain the Pd-C/Al2O3And (4) selecting a catalyst.
600g of sodium isethionate solution (15.0 wt%) was placed in a 1L high-pressure reactor, a certain amount of liquid ammonia was introduced, the ammonia concentration was controlled to 20.0 wt%, and then 0.45g (0.5 wt%) of the above Pd-C/Al was added2O3The catalyst is selected, the reaction system is heated to 150 ℃, the system pressure is 8.5MPa, the reaction is carried out for 35min, the conversion rate of the hydroxyethyl sodium sulfonate in the ammonolysis reaction is 99.1 percent, the yield of the obtained sodium taurate is 95.8 percent, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 96.67 percent, 2.92 percent and 0.41 percent respectively.
Evaporating the reaction solution at 90 ℃ and 60kPa (absolute pressure) to remove excessive ammonia and part of water, concentrating the sodium taurate to 40 wt%, adding 98 wt% concentrated sulfuric acid at 75 ℃ to adjust the pH of the system to 8.0, cooling to 25 ℃, crystallizing for 8h, wherein the once-through yield of the taurine after crystallization is 79.2%, and the total yield of the taurine after recycling mother solution is 95.5%.
Example 4
Adding 4.5g (1.5 wt%) of sodium taurate into 300g of ethanol aqueous solution (82.0 wt%), then adding 149.9g of aluminum isopropoxide, stirring uniformly at 25 ℃, adding 12.55g of tetraamminepalladium chloride, continuing stirring, carrying out hydrolysis reaction at 60 ℃ for 10h, filtering and washing the precipitate, drying at 110 ℃ for 5h, and then placing the precipitate in a nitrogen roasting furnace for roasting at 500 ℃ for 8h to obtain Pd-C/Al2O3And (4) selecting a catalyst.
600g of sodium isethionate solution (29.0 wt%) was placed in a 1L high-pressure reactor, a certain amount of liquid ammonia was passed through, the ammonia concentration was controlled to 15.0 wt%, and 5.22g (3 wt%) of the above Pd-C/Al was added2O3The catalyst is selected, the reaction system is heated to 190 ℃, the system pressure is 9MPa, the reaction is carried out for 90min, the conversion rate of the hydroxyethyl sodium sulfonate in the ammonolysis reaction is 98.6 percent, the yield of the obtained sodium taurate is 93.2 percent, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 94.52 percent, 4.13 percent and 1.35 percent respectively.
Evaporating the reaction solution at 90 ℃ and 60kPa (absolute pressure) to remove excessive ammonia and part of water, concentrating the sodium taurate to 36 wt%, adding 98% concentrated sulfuric acid at 80 ℃ to adjust the pH of the system to 8.2, cooling to 40 ℃, crystallizing for 4h, wherein the once-through yield of the taurine after crystallization is 78.8%, and the total yield of the taurine after recycling mother liquor is 94.8%.
Example 5
Adding 3.9g (1.3 wt%) of sodium taurate into 300g of ethanol aqueous solution (15.0 wt%), then adding 54.12g of aluminum isopropoxide, stirring uniformly at 25 ℃, adding 1.29g of tetraamminepalladium chloride, continuing stirring, carrying out hydrolysis reaction at 80 ℃ for 7h, filtering, washing and drying the precipitate at 100 ℃ for 6h, then placing the precipitate in a nitrogen roasting furnace for roasting at 480 ℃ for 10h to obtain the Pd-C/Al2O3And (4) selecting a catalyst.
600g of sodium isethionate solution (13.0 wt%) was placed in a 1L high-pressure reactor, a certain amount of liquid ammonia was introduced, the ammonia concentration was controlled to 12.0 wt%, and then 2.03g (2.6 wt%) of the above Pd-C/Al was added2O3The catalyst is selected, the reaction system is heated to 175 ℃, the system pressure is 11MPa, the reaction is carried out for 100min, the conversion rate of the hydroxyethyl sodium sulfonate in the ammonolysis reaction is 98.0 percent, the yield of the obtained sodium taurate is 92.0 percent, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 93.88 percent, 4.43 percent and 1.69 percent respectively.
Evaporating the reaction solution at 90 ℃ and 60kPa (absolute pressure) to remove excessive ammonia and part of water, concentrating the sodium taurate to 36.5 wt%, adding 98% concentrated sulfuric acid at 82 ℃ to adjust the pH of the system to 8.1, cooling to 25 ℃, crystallizing for 6h, wherein the once-through yield of the taurine after crystallization is 74.8%, and the total yield of the taurine after recycling mother solution is 93.2%.
Example 6
Adding 2.1g (0.7 wt%) sodium taurate into 300g ethanol water solution (55.0 wt%), then adding 17.57g aluminum sec-butoxide, stirring uniformly at 25 deg.C, adding 4.69g diethyl diamine palladium sulfate, stirring continuously, carrying out hydrolysis reaction at 50 deg.C for 5h, filtering, washing, drying at 120 deg.C for 3h, and then placing in nitrogen roasting furnace for roasting at 450 deg.CAfter 5 hours, Pd-C/Al can be obtained2O3And (4) selecting a catalyst.
600g of sodium isethionate solution (17.0 wt%) was placed in a 1L high-pressure reactor, a certain amount of liquid ammonia was passed through, the ammonia concentration was controlled to 24.0 wt%, and then 2.65g (2.6 wt%) of the above Pd-C/Al was added2O3The catalyst is selected, the reaction system is heated to 160 ℃, the system pressure is 8.7MPa, the reaction is carried out for 50min, the conversion rate of the hydroxyethyl sodium sulfonate in the ammonolysis reaction is 98.4 percent, the yield of the obtained sodium taurate is 93.9 percent, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 95.43 percent, 2.75 percent and 1.82 percent respectively.
Evaporating the reaction solution at 90 ℃ and 60kPa (absolute pressure) to remove excessive ammonia and part of water, concentrating the sodium taurate to 37 wt%, adding 98% concentrated sulfuric acid at 75 ℃ to adjust the pH of the system to 8.0, cooling to 20 ℃ for crystallization for 3h, wherein the once-through yield of taurine after crystallization is 78.3%, and the total yield of taurine after mother solution is recycled is 98.1%.
Example 7
Adding 4.5g (1.5 wt%) sodium taurate into 300g ethanol aqueous solution (80.0 wt%), then adding 180.73g aluminum tert-butoxide, stirring uniformly at 25 ℃, adding 2.97g palladium sulfate, continuing stirring, carrying out hydrolysis reaction at 40 ℃ for 5h, filtering, washing, drying at 90 ℃ for 4h, then placing in a nitrogen roasting furnace, roasting at 350 ℃ under normal pressure for 8h, thus obtaining Pd-C/Al2O3And (4) selecting a catalyst.
600g of sodium isethionate solution (33.0 wt%) was placed in a 1L high-pressure reactor, a certain amount of liquid ammonia was passed through, the ammonia concentration was controlled to 14.0 wt%, and then 15.84g (8 wt%) of the above Pd-C/Al was added2O3The catalyst is selected, the reaction system is heated to 120 ℃, the system pressure is 8.7MPa, the reaction is carried out for 50min, the conversion rate of the hydroxyethyl sodium sulfonate in the ammonolysis reaction is 98.1 percent, the yield of the obtained sodium taurate is 92.4 percent, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 94.19 percent, 3.79 percent and 2.02 percent respectively.
Evaporating the reaction solution at 90 ℃ and 60kPa (absolute pressure) to remove excessive ammonia and part of water, concentrating the sodium taurate to 39 wt%, adding 98% concentrated sulfuric acid at 85 ℃ to adjust the pH of the system to 8.1, cooling to 36 ℃, crystallizing for 7h, wherein the once-through yield of the taurine after crystallization is 73.7%, and the total yield of the taurine after recycling mother liquor is 94.0%.
Comparative example 1
Preparation of taurine from sodium isethionate: differs from example 1 only in that Pd-C/Al prepared in example 12O3The shape-selective catalyst was replaced with NaOH catalyst.
After the ammonolysis reaction, the conversion rate of the hydroxyethyl sodium sulfonate is 90.5%, the yield of the obtained sodium taurate is 58.5%, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 64.64%, 30.27% and 5.09% respectively.
The once-through yield of the crystallized taurine is 63.3 percent, and the total yield of the taurine is 70.2 percent after the mother liquor is recycled.
Comparative example 2
Preparation of taurine from sodium isethionate: differs from example 1 only in that Pd-C/Al prepared in example 12O3Substitution of shape selective catalyst with Na2CO3A catalyst.
After the ammonolysis reaction, the conversion rate of the hydroxyethyl sodium sulfonate is 94.5%, the yield of the obtained sodium taurate is 61.5%, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 65.08%, 30.44% and 4.48% respectively.
The once-through yield of the crystallized taurine is 65.8 percent, and the total yield of the taurine is 75.4 percent after the mother liquor is recycled.
Comparative example 3
Adding 3.0g (1.0 wt%) of sodium taurate into 300g of ethanol aqueous solution (68.0 wt%), then adding 141.75g of cerium nitrate hexahydrate, stirring uniformly at 25 ℃, adding 4.75g of nickel nitrate hexahydrate, continuing stirring, and then carrying out hydrolysis reaction at 32 ℃ for 5 hours; then filtering, washing and drying the precipitate for 4h at 100 ℃, and then putting the precipitate into a nitrogen roasting furnace for roasting for 4h at 450 ℃ to obtain NiO-C/CeO2And (4) selecting a catalyst.
Preparation of taurine from sodium isethionate: differs from example 1 only in that Pd-C/Al prepared in example 12O3The shape-selective catalyst is replaced by NiO-C/CeO prepared in the comparative example2And (4) selecting a catalyst.
After the ammonolysis reaction, the conversion rate of the hydroxyethyl sodium sulfonate is 90.7%, the yield of the obtained sodium taurate is 81.5%, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 89.86%, 8.24% and 1.90% respectively.
The once-through yield of the crystallized taurine is 72.3 percent, and the total yield of the taurine is 87.9 percent after the mother liquor is recycled.
Comparative example 4
Preparation of Pd-C/Al2O3Catalyst: only different from example 1 in that 68.0 wt% of an aqueous ethanol solution was replaced with 68.0 wt% of an aqueous acetone solution to prepare Pd-C/Al2O3A catalyst.
Preparation of taurine from sodium isethionate: differs from example 1 only in that Pd-C/Al prepared in example 12O3The shape-selective catalyst is replaced by the Pd-C/Al prepared in the comparative example2O3A catalyst.
After the ammonolysis reaction, the conversion rate of the hydroxyethyl sodium sulfonate is 92.5%, the yield of the obtained sodium taurate is 80.1%, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 86.59%, 7.89% and 5.52% respectively.
The once-through yield of the crystallized taurine is 70.6 percent, and the total yield of the taurine is 84.5 percent after the mother liquor is recycled.
Comparative example 5
Preparing a catalyst: the catalyst was prepared only by replacing aluminum sec-butoxide with aluminum chloride, as distinguished from example 1.
Preparation of taurine from sodium isethionate: differs from example 1 only in that Pd-C/Al prepared in example 12O3The shape-selective catalyst was replaced with the catalyst prepared in this comparative example.
After the ammonolysis reaction, the conversion rate of the hydroxyethyl sodium sulfonate is 93.3%, the yield of the obtained sodium taurate is 83.7%, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 89.71%, 9.11% and 1.18% respectively.
The once-through yield of the crystallized taurine is 73.2 percent, and the total yield of the taurine is 88.4 percent after the mother liquor is recycled.
Comparative example 6
Preparing a catalyst: the only difference from example 1 is that no sodium taurate was added and the catalyst was prepared.
Preparation of taurine from sodium isethionate: differs from example 1 only in that Pd-C/Al prepared in example 12O3The shape-selective catalyst was replaced with the catalyst prepared in this comparative example.
After the ammonolysis reaction, the conversion rate of the hydroxyethyl sodium sulfonate is 89.5%, the yield of the obtained sodium taurate is 62.6%, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 69.94%, 24.57% and 5.49% respectively.
The once-through yield of the crystallized taurine is 69.6 percent, and the total yield of the taurine is 82.1 percent after the mother liquor is recycled.
Comparative example 7
Preparing a catalyst: the only difference from example 1 is that the calcination in nitrogen was replaced by an air calcination furnace to produce Pd/Al2O3A catalyst.
Preparation of taurine from sodium isethionate: differs from example 1 only in that Pd-C/Al prepared in example 12O3The shape-selecting catalyst is replaced by the Pd/Al prepared in the comparative example2O3A catalyst.
After the ammonolysis reaction, the conversion rate of the hydroxyethyl sodium sulfonate is 95.5%, the yield of the obtained sodium taurate is 84.6%, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 88.59%, 8.56% and 2.85% respectively.
The once-through yield of the crystallized taurine is 74.9 percent, and the total yield of the taurine is 89.9 percent after the mother liquor is recycled.
Comparative example 8
Preparing a catalyst: in 300g of an aqueous ethanol solution (68.0 wt.%) Adding 3.0g (1.0 wt%) of sodium taurate and 0.05g of activated carbon, then adding 80.3g of aluminum sec-butoxide, stirring uniformly at 25 ℃, adding 3.76g of palladium nitrate, continuing stirring, and then carrying out hydrolysis reaction at 32 ℃ for 5 hours; then filtering, washing and drying the precipitate for 4h at 100 ℃, and then putting the precipitate into a nitrogen roasting furnace for roasting for 4h at 450 ℃ to obtain the Pd-C/Al2O3And (4) selecting a catalyst.
Preparation of taurine from sodium isethionate: differs from example 1 only in that Pd-C/Al prepared in example 12O3The shape-selective catalyst was replaced with the catalyst prepared in this comparative example.
After the ammonolysis reaction, the conversion rate of the hydroxyethyl sodium sulfonate is 93.5%, the yield of the obtained sodium taurate is 81.6%, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 87.27%, 10.92% and 1.81% respectively.
The once-through yield of the crystallized taurine is 72.5 percent, and the total yield of the taurine is 88.1 percent after the mother liquor is recycled.
Comparative example 9
Preparing a catalyst: the only difference from example 1 was that 3.76g of palladium nitrate was replaced with 6.60g of iron nitrate nonahydrate to obtain Fe-C/Al2O3And (4) selecting a catalyst.
Preparation of taurine from sodium isethionate: differs from example 1 only in that Fe-C/Al prepared in example 12O3The shape-selective catalyst was replaced with the catalyst prepared in this comparative example.
After the ammonolysis reaction, the conversion rate of the hydroxyethyl sodium sulfonate is 90.2%, the yield of the obtained sodium taurate is 80.4%, and the selectivity of the sodium taurate, the disubstituted sodium taurate and the trisubstituted sodium taurate is 89.14%, 7.92% and 2.94% respectively.
The once-through yield of the crystallized taurine is 71.0 percent, and the total yield of the taurine is 85.1 percent after the mother liquor is recycled.

Claims (18)

1. A method for preparing taurine from sodium isethionate is characterized in that the method comprises the step of reacting sodium isethionate with ammonia in Pd-C/Al2O3Preparing taurine in the presence of a shape-selective catalyst;
the Pd-C/Al2O3The shape-selective catalyst is prepared by taking sodium taurate as a template, adding organic aluminum salt into an ethanol water solution for hydrolysis reaction, adding palladium salt into a hydrolysis reaction system, and roasting a product after the hydrolysis reaction in a nitrogen atmosphere.
2. The method of claim 1, wherein the Pd-C/Al is2O3The preparation method of the shape-selective catalyst comprises the following steps:
(1) dissolving sodium taurate in aqueous solution of ethanol, and then adding organic aluminum salt and palladium salt into the aqueous solution to perform hydrolysis reaction;
(2) separating solid from the reaction liquid in the step (1), drying, and roasting in a nitrogen environment to obtain Pd-C/Al2O3And (4) selecting a catalyst.
3. The method according to claim 1, wherein in the step (1), the mass fraction of ethanol in the ethanol aqueous solution is 10-85 wt%;
the concentration of the sodium taurate in the ethanol water solution is 0.1-1.5 wt%;
the molar ratio of the organic aluminum salt to the sodium taurate is 10-24: 1;
the molar ratio of the palladium salt to the organic aluminum salt is 0.01-0.07: 1.
4. the method according to claim 3, wherein in the step (1), the mass fraction of ethanol in the ethanol aqueous solution is 65-70 wt%;
the concentration of the sodium taurate in the ethanol water solution is 0.5-0.8 wt%;
the molar ratio of the organic aluminum salt to the sodium taurate is 15-17: 1;
the molar ratio of the palladium salt to the organic aluminum salt is 0.03-0.05: 1.
5. the method according to claim 2, wherein in the step (1), the hydrolysis reaction temperature is 20-80 ℃, and the reaction time is 0.5-10 h;
in the step (2), the drying temperature is 80-120 ℃, and the drying time is 2-6 h; the roasting temperature is 350-500 ℃, and the roasting time is 5-10 h.
6. The method according to claim 5, wherein, in the step (1), the hydrolysis reaction temperature is 30-33 ℃; the reaction time is 4-6 h;
in the step (2), the drying temperature is 100-120 ℃, and the drying time is 3-4 h; the roasting temperature is 400-450 ℃, and the roasting time is 6-8 h.
7. The method of claim 5, wherein in step (2), N is used at normal pressure for the calcination2And (4) environment.
8. The method according to claim 1, wherein the organic aluminum salt is one or more of aluminum isopropoxide, aluminum sec-butoxide, and aluminum tert-butoxide;
the palladium salt is one or more of palladium chloride, palladium acetate, palladium nitrate, palladium tetraammine dichloride, palladium sulfate and palladium ethylenediamine sulfate.
9. The method according to claim 8, wherein the organic aluminum salt is aluminum isopropoxide and/or aluminum sec-butoxide; the palladium salt is palladium chloride and/or palladium nitrate.
10. Method according to any of claims 1-9, characterized in that it comprises the following steps:
1) adding liquid ammonia and Pd-C/Al into the water solution of the hydroxyethyl sodium sulfonate2O3Carrying out ammonolysis reaction on a shape-selective catalyst to obtain a reaction solution containing sodium taurate;
2) removing ammonia from the reaction liquid obtained in the step 1), and then neutralizing and crystallizing to obtain the taurine.
11. The method according to claim 10, wherein in step 1), the concentration of the aqueous solution of sodium isethionate is 10-35 wt%;
the concentration of the liquid ammonia in the reaction system is 10-30 wt%;
the Pd-C/Al2O3The dosage of the shape-selecting catalyst is 0.5-8 wt% of the hydroxyethyl sodium sulfonate.
12. The method according to claim 11, wherein in step 1), the concentration of the aqueous solution of sodium isethionate is 15-25 wt%;
the concentration of the liquid ammonia in the reaction system is 15-27 wt%;
the Pd-C/Al2O3The dosage of the shape-selecting catalyst is 1.0-4.0 wt% of the hydroxyethyl sodium sulfonate.
13. The method according to claim 12, wherein in step 1), the concentration of the aqueous solution of sodium isethionate is 15-18 wt%;
the concentration of the liquid ammonia in the reaction system is 18-23 wt%;
the Pd-C/Al2O3The dosage of the shape-selecting catalyst is 1.2-2.0 wt% of the hydroxyethyl sodium sulfonate.
14. The method as claimed in claim 10, wherein in the step 1), the ammonolysis reaction is carried out at a temperature of 40-210 ℃, a reaction pressure of 0.1-15MPa gauge and a reaction time of 10-120 min.
15. The method of claim 14, wherein the ammonolysis reaction is carried out at a temperature of 90-200 ℃, a pressure of 2-10MPa gauge, and a reaction time of 10-80 min.
16. The method as claimed in claim 15, wherein the ammonolysis reaction is carried out at a temperature of 130 ℃ and 150 ℃, a reaction pressure of 5-9MPa, and a reaction time of 20-60 min.
17. The method as claimed in claim 10, wherein in the step 2), the ammonia removal operation adopts a flash evaporation ammonia removal method, excess ammonia in the ammonolysis reaction in the step 1) is removed through flash evaporation, and evaporation concentration is carried out, so that the concentration of sodium taurate is raised to 36-41 wt%;
the neutralization operation adopts concentrated sulfuric acid for neutralization, the neutralization temperature is 50-90 ℃, and the concentrated sulfuric acid is added to adjust the pH value of the system to 7-9;
and crystallizing at 20-40 deg.C for 2-8 h.
18. The method of claim 17, wherein the concentration of sodium taurate is raised to 37-39 wt%;
the neutralization temperature is 70-80 ℃;
and crystallizing at 25-30 deg.C for 4-5 h.
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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD84394A (en) *
JPH04352760A (en) * 1990-12-20 1992-12-07 Nippon Shokubai Co Ltd Production of aminoalkylsulfonic acids
JPH06329615A (en) * 1993-05-21 1994-11-29 Tosoh Corp Production of sodium aminoethanesulfonate or sodium n-substituted aminoethanesulfonate
JP3003287B2 (en) * 1991-06-19 2000-01-24 東ソー株式会社 Method for producing sodium N-alkylaminoethanesulfonate
CN101850305A (en) * 2010-06-17 2010-10-06 新疆有色金属研究所 Novel mica inhibitor and preparation method and use method thereof
CN102675160A (en) * 2012-05-07 2012-09-19 黄冈永安药业有限公司 Device and method for continuously producing sodium methyl taurate in pipeline mode
CN105732440A (en) * 2016-03-21 2016-07-06 江阴华昌食品添加剂有限公司 Method of fully recycling mother liquid to produce taurine

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD84394A (en) *
JPH04352760A (en) * 1990-12-20 1992-12-07 Nippon Shokubai Co Ltd Production of aminoalkylsulfonic acids
JP3003287B2 (en) * 1991-06-19 2000-01-24 東ソー株式会社 Method for producing sodium N-alkylaminoethanesulfonate
JPH06329615A (en) * 1993-05-21 1994-11-29 Tosoh Corp Production of sodium aminoethanesulfonate or sodium n-substituted aminoethanesulfonate
CN101850305A (en) * 2010-06-17 2010-10-06 新疆有色金属研究所 Novel mica inhibitor and preparation method and use method thereof
CN102675160A (en) * 2012-05-07 2012-09-19 黄冈永安药业有限公司 Device and method for continuously producing sodium methyl taurate in pipeline mode
CN105732440A (en) * 2016-03-21 2016-07-06 江阴华昌食品添加剂有限公司 Method of fully recycling mother liquid to produce taurine

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
乙撑亚胺法合成牛磺酸的工艺研究;陈文如等;《浙江化工》;20110515(第05期);第18-20页 *
牛磺酸氨解反应工艺研究;刘福明等;《山东化工》;20150308(第05期);第27-28,30页 *
牛磺酸生产工艺中氨解反应条件的优化;吴江等;《湖北工业大学学报》;20040228(第01期);第23-26页 *

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