CN110963946B - Preparation method of sodium methyl taurate - Google Patents
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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
- C07C303/32—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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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
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Abstract
The invention discloses a method for preparing sodium methyl taurate by a sodium taurate one-pot two-step method, which comprises the steps of reacting sodium taurate with formaldehyde under the action of a novel supported composite metal organic catalyst to obtain sodium methyl taurate aqueous solution, and finally obtaining sodium methyl taurate through crystallization, separation and drying; the catalyst is represented as Pd-Ce-Z-X/Y, wherein Z is a cocatalyst and is selected from one or more of Re, Sn, In, Sc and Al; x is one or more of 2- (2-diphenylphosphine) phenylpyridine, 2- (diphenylphosphine) methylpyrrole, N-methyl-2- (diphenylphosphine) methylpyrrole and 1- (2-diphenylphosphine-1-naphthalene) isoquinoline; y is carrier selected from one or more of ordered mesoporous carbon, molecular sieve, silicon dioxide and neutral alumina. The method has simple process, the conversion rate of the raw material is more than 90 percent, and the selectivity of the product is more than 95 percent.
Description
Technical Field
The invention relates to a preparation method of sodium methyl taurate.
Technical Field
The sodium methyl taurate is an important derivative of the sodium taurate and can be used as an important intermediate of daily chemicals, medicines and surfactants. In the field of daily use chemistry, various high value-added products such as sodium cocoyl-N-methyltaurate, hydroxyethyl acrylate/sodium acryloyldimethyltaurate copolymer, sodium polyacryloyldimethyltaurate and the like can be synthesized, and these products have mild properties and are therefore useful as mild surfactants. With the increasing living standard of people, the demand of the mild surfactant is greatly increased.
Among the mild surfactants of the sodium methyltaurate series, the synthesis of sodium methyltaurate is the most critical reaction. So far, the following methods for synthesizing sodium methyltaurate are available: common methods include direct N-methylation; a process for the reconversion to an N-methylated product via an oxazolidinone intermediate; reductive amination, and the like. Some of these methods produce unnecessary by-products, some methods use expensive raw materials, some methods require harsh conditions, some methods have many reaction steps, and inevitable errors are likely to occur, thereby reducing the overall reaction yield.
Chinese patent CN106674061A discloses that using an aqueous solution of ammonium salt as a catalyst, reacting N-methylacetamide with sulfuric acid to obtain N-methyltaurine, reacting with methyltauramine, treating with hydrogen peroxide to obtain N-methyltaurate, and finally performing high-temperature reflux reaction and centrifugal filtration in the presence of alkali, a solvent and a catalyst to obtain N-methyltaurate. The method has the problems of complex process route, difficult catalyst recovery, higher reaction temperature, higher risk of the used hydrogen peroxide and the like.
In conclusion, in the industrial production of the synthetic sodium methyl taurate, a method with simple process route, less by-products, lower raw material cost, mild reaction conditions and high yield still needs to be developed.
Disclosure of Invention
The invention aims to provide a method for preparing sodium methyl taurate, which has the advantages of simple process route, less by-products, lower raw material cost and mild reaction conditions.
In order to achieve the purpose of the invention, the technical scheme adopted by the invention is as follows:
the invention provides a preparation method of sodium methyl taurate, in particular to a method for generating sodium methyl taurate by carrying out addition and reduction reactions on sodium taurate and formaldehyde through a one-pot two-step method, which can effectively reduce the treatment operation steps after the reaction and reduce the energy consumption; effectively reduces three wastes and is suitable for industrial application. The adopted scheme comprises the following steps:
a preparation method of sodium methyl taurate comprises the following steps: under the action of a catalyst, sodium taurate and formaldehyde are subjected to addition and reduction reactions to generate a sodium methyl taurate aqueous solution, and the sodium methyl taurate product is obtained through crystallization, separation and drying.
The formaldehyde is generally used in a 35 to 40% strength by weight solution.
The reaction route of the invention is as follows:
in the preparation method, the molar ratio of the sodium taurate to the formaldehyde is 1:1-1:2, the dosage of the catalyst is 2-8 wt% relative to the sodium taurate, firstly, the sodium taurate and the formaldehyde react for 5-8h at the reaction temperature of 50-100 ℃, then, hydrogen is introduced until the reaction pressure is 5-8barg, and the reaction is continued for 5-10 h. The product can be crystallized by known crystallization methods, such as crystallization temperature of 60-80 ℃ and crystallization time of 2-6 h. The drying condition is drying at 80-100 deg.C for 8-9 h.
In the method, the used catalyst is a supported composite metal organic catalyst which is expressed as Pd-Ce-Z-X/Y, wherein Z is a cocatalyst and is selected from one or more of Re, Sn, In, Sc and Al, and preferably from one or more of Re, In and Sc; x is one or more of 2- (2-diphenylphosphine) phenylpyridine, 2- (diphenylphosphine) methylpyrrole, N-methyl-2- (diphenylphosphine) methylpyrrole and 1- (2-diphenylphosphine-1-naphthalene) isoquinoline, preferably 2- (2-diphenylphosphine) phenylpyridine and/or 1- (2-diphenylphosphine-1-naphthalene) isoquinoline; y is a carrier and is selected from one or more of ordered mesoporous carbon, molecular sieve, silicon dioxide and neutral alumina, and preferably from one or more of 4A molecular sieve and ordered mesoporous carbon.
In the catalyst, based on the total weight of the catalyst, the mass fraction of Pd is 1-10%, Ce is 10-30%, X is 30-50%, Y is 20-40%, and Z is 14-20%; preferably, the mass fraction of Pd is 5-8%, the mass fraction of Ce is 15-20%, the mass fraction of X is 35-40%, the mass fraction of Y is 25-30%, and the mass fraction of Z is 15-18%.
In the catalyst structure, Pd, Ce and Z are metal elements and exist in the catalyst in a complex form, X is an organic matter containing N and P elements, and the dosage of a ligand can be reduced by forming chemical bonds and coordination bonds with Ce, Z and Pd through lone-pair electrons on N, P double elements in the catalyst; pd, Ce, Z and X together form a metal organic framework material; the carrier Y plays a role in dispersing the metal organic framework material, so that the active center atoms of the catalyst are distributed more uniformly.
The preparation method of the supported composite metal organic catalyst comprises the following steps:
(1) dissolving Pd-containing compound and X in water, stirring for 2-4h at 60-90 deg.C, mixing thoroughly, adding Ce-containing compound and Z-containing compound into the aqueous solution, and dispersing carrier Y in the mixed aqueous solution to obtain slurry;
(2) dropwise adding an alkaline precipitator into the slurry until the pH value is 9-11, and aging to obtain slurry;
(3) and carrying out post-treatment on the slurry to obtain the supported composite metal organic catalyst.
In the preparation method of the catalyst, the amount of water used in step (1) is not particularly limited, and the Pd-containing compound, X, Ce-containing compound, and Z-containing compound added may be completely dissolved.
In the preparation method of the catalyst, in the step (1), the Pd-containing compound is selected from one or more of palladium acetate, palladium chloride and tetratriphenylphosphine palladium, preferably tetratriphenylphosphine palladium; the Ce-containing compound and the Z-containing compound are selected from soluble salts containing Ce and Z, such as nitrate, hydrochloride, acetate and the like, but are not limited to the above.
In the step (2), the alkaline precipitant is selected from one or more of sodium carbonate, sodium bicarbonate, ammonium carbonate and ammonia water, the alkaline precipitant can be an aqueous solution with the concentration of 10-30 wt%, and the temperature is controlled to be 35-45 ℃ in the process of dropwise adding the alkaline precipitant; the aging time is 3-6h, and the aging temperature is 40-70 ℃.
In the preparation method of the catalyst, in the step (3), the post-treatment process comprises the following steps: and filtering, washing and drying the slurry to obtain a filter cake, and roasting, crushing, tabletting and forming the dried filter cake to obtain the required catalyst. Wherein the drying temperature is 80-100 ℃, and the drying time is 7-10 h; the roasting temperature is 150-200 ℃, and the roasting time is 5-10 h.
The invention has the advantages that:
1. the invention has simple process route and low cost of raw materials.
2. The novel supported composite metal organic catalyst is prepared, coordination bonds formed by lone-pair electrons on N, P in a catalyst framework and Pd are easy to form the interaction of bonds with double bonds, the concentration of reactants on the surface of the catalyst is increased in the catalytic reaction process of the catalyst, and the double bonds are promoted to carry out hydrogenation reaction under the catalysis of Pd; meanwhile, Ce is easy to form d-p pi feedback bond with carbonyl oxygen, so that the electrophilicity of carbonyl carbon is increased, and the carbonyl is easier to generate nucleophilic reaction; the active component of the catalyst and the active component of the cocatalyst are used in a matching way, so that the by-product of N-dimethylamine can be effectively inhibited.
2. The method can produce the sodium methyl taurate by addition reduction at a lower operation temperature, the conversion rate of the raw materials is more than 90 percent, and the selectivity of the product is more than 95 percent.
Detailed Description
The following examples are intended to illustrate the invention in detail, but are not to be construed as limiting the invention.
Detection method
An analytical instrument:
gas chromatographic column: agilent HP-INNOWax;
the analysis method comprises the following steps:
temperature of the column box: 80 ℃; sample inlet temperature: 270 ℃; the split ratio is 50: 1; carrier gas flow: 0.9 mL/min; temperature rising procedure: maintaining at 80 deg.C for 0min, increasing to 250 deg.C at a rate of 15 deg.C/min, and maintaining for 10 min.
Molecular water is not counted in the raw materials of the following examples, and organic matters and carriers are not lost.
Example 1
Mixing 52g of palladium acetate and 172.5g of 1- (2-diphenylphosphine-1-naphthalene) isoquinoline in 500g of distilled water, heating to 70 ℃, and stirring for 2 hours; 305.46g of cerium nitrate and 379.9g of scandium nitrate are dissolved in 1000g of water to prepare an aqueous solution, the aqueous solution is added into the mixed aqueous solution of the palladium acetate and the 1- (2-diphenylphosphine-1-naphthalene) isoquinoline, and 123.22g of 4A molecular sieve is added under the stirring state to obtain slurry A;
taking a 20 wt% sodium bicarbonate solution as an alkaline precipitant, respectively heating the slurry A and the alkaline precipitant to 40 ℃, slowly dropwise adding the alkaline precipitant into the slurry A until the pH of the system is 10.0, and controlling the reaction temperature in the precipitation process to be 40 ℃; after the precipitation reaction is finished, aging is carried out for 4 hours at 70 ℃ to obtain slurry;
and fully filtering the slurry, washing the surface of the filter cake with deionized water, drying the filter cake at 80 ℃ for 10 hours to obtain a dried filter cake, roasting at 200 ℃ for 6 hours, crushing, tabletting and forming to obtain the catalyst.
Preparing sodium methyl taurate:
412g of sodium taurate, 227g of 37% formaldehyde aqueous solution and 21g of the prepared catalyst are mixed and added into a hydrogenation kettle, the temperature is raised to 70 ℃, the mixture is fully stirred for 7 hours, and then hydrogen is introduced until the pressure is 7barg for reaction for 6 hours;
filtering the obtained mixed solution to remove the solid catalyst, separating out reaction liquid, pouring the reaction liquid into a crystallization kettle, setting the crystallization temperature at 70 ℃, crystallizing for 2 hours, carrying out suction filtration on the obtained mixed solution, and drying the obtained filter cake for 8 hours at 90 ℃. This gave about 411.3g of sodium methyltaurate (nuclear magnetic data:1H NMR(D2o,400MHz): δ 3.11(t, J ═ 7.1Hz,2H),3.26(s,3H),3.53(t, J ═ 7.1Hz, 2H)). The conversion rate is as follows: 93.75%, selectivity 97.23%.
Example 2
Mixing 63g of palladium acetate and 209.04g of 1- (2-diphenylphosphine-1-naphthalene) isoquinoline in 500g of distilled water, heating to 80 ℃, and stirring for 4 hours; 370.13g of cerium nitrate and 460.33g of scandium nitrate are dissolved in 1000g of water to prepare an aqueous solution, the aqueous solution is added into the mixed aqueous solution of palladium acetate and 1- (2-diphenylphosphine-1-naphthalene) isoquinoline, and 149.31g of ordered mesoporous carbon is added under the stirring state to obtain slurry A;
taking a 20 wt% sodium carbonate solution as an alkaline precipitator, respectively heating the slurry A and the alkaline precipitator to 40 ℃, slowly dropwise adding the alkaline precipitator into the slurry A until the pH of the system is 10.0, and controlling the reaction temperature in the precipitation process to be 40 ℃; after the precipitation reaction is finished, aging is carried out for 4 hours at 70 ℃ to obtain slurry;
and fully filtering the slurry, washing the surface of the filter cake with deionized water, drying the filter cake at 90 ℃ for 10 hours to obtain a dried filter cake, roasting at 150 ℃ for 8 hours, crushing, tabletting and forming to obtain the catalyst.
Preparing sodium methyl taurate:
mixing 423g of sodium taurate, 233.3g of 37% formaldehyde aqueous solution and 21.15g of prepared catalyst, adding into a hydrogenation kettle, heating to 80 ℃, fully stirring for 6 hours, and introducing hydrogen into the hydrogenation kettle until the pressure is 7barg for reaction for 8 hours;
filtering the obtained mixed solution to remove the solid catalyst, separating out reaction liquid, pouring the reaction liquid into a crystallization kettle, setting the crystallization temperature at 80 ℃, crystallizing for 4 hours, carrying out suction filtration on the obtained mixed solution, and drying the obtained filter cake for 8 hours at the temperature of 100 ℃. Thus, about 427.9g of sodium methyltaurate were obtained. The conversion rate is as follows: 94% and selectivity 98%.
Example 3
Mixing 50g of palladium chloride and 210.04g of 1- (2-diphenylphosphine-1-naphthalene) isoquinoline in 500g of distilled water, heating to 70 ℃, and stirring for 2 hours; 371.9g of cerium nitrate and 235.85g of indium nitrate are dissolved in 1000g of water to prepare an aqueous solution, the aqueous solution is added into the mixed aqueous solution of the palladium chloride and the 1- (2-diphenylphosphine-1-naphthalene) isoquinoline, and 150.03g of ordered mesoporous carbon is added under the stirring state to obtain slurry A;
taking 20 wt% ammonium carbonate solution as an alkaline precipitant, respectively heating the slurry A and the alkaline precipitant to 40 ℃, slowly dropwise adding the alkaline precipitant into the slurry A until the pH of the system is 10.0, and controlling the reaction temperature in the precipitation process to be 40 ℃; after the precipitation reaction is finished, aging is carried out for 4 hours at 60 ℃ to obtain slurry;
and fully filtering the slurry, washing the surface of the filter cake with deionized water, drying the filter cake at 100 ℃ for 10 hours to obtain a dried filter cake, roasting at 190 ℃ for 7 hours, crushing, tabletting and forming to obtain the catalyst.
Preparing sodium methyl taurate:
436g of sodium taurate, 240.5g of 37 percent formaldehyde aqueous solution and 21.8g of prepared catalyst are mixed and added into a hydrogenation kettle, the temperature is raised to 70 ℃, the mixture is fully stirred for 6 hours, and hydrogen is introduced into the hydrogenation kettle until the pressure is 7barg for reaction for 7 hours;
filtering the obtained mixed solution to remove the solid catalyst, separating out reaction liquid, pouring the reaction liquid into a crystallization kettle, setting the crystallization temperature at 70 ℃, crystallizing for 2 hours, carrying out suction filtration on the obtained mixed solution, and drying the obtained filter cake for 9 hours at 90 ℃. Thus, about 448.9g of sodium methyltaurate were obtained. The conversion rate is as follows: 95.64%, and selectivity 98.29%.
Example 4
212g of tetrakis (triphenylphosphine) palladium and 136.66g of 1- (2-diphenylphosphino-1-naphthalene) isoquinoline are mixed in 500g of distilled water, and the mixture is heated to 70 ℃ and stirred for 2 hours; 241.98g of cerium nitrate and 153.46g of indium nitrate are dissolved in 1000g of water to prepare an aqueous solution, the aqueous solution is added into the mixed aqueous solution of the tetrakis (triphenylphosphine) palladium and the 1- (2-diphenylphosphine-1-naphthalene) isoquinoline, and 97.62g of a 4A molecular sieve is added under stirring to obtain slurry A;
taking a 20 wt% sodium bicarbonate solution as an alkaline precipitant, respectively heating the slurry A and the alkaline precipitant to 40 ℃, slowly dropwise adding the alkaline precipitant into the slurry A until the pH of the system is 10.0, and controlling the reaction temperature in the precipitation process to be 40 ℃; after the precipitation reaction is finished, aging is carried out for 4 hours at 60 ℃ to obtain slurry;
and fully filtering the slurry, washing the surface of the filter cake with deionized water, drying the filter cake at 100 ℃ for 10h, roasting at 200 ℃ for 5h, crushing, tabletting and forming to obtain the catalyst.
Preparing sodium methyl taurate:
mixing 451g of sodium taurate, 300g of 37% formaldehyde aqueous solution and 22.55g of prepared catalyst, adding into a hydrogenation kettle, heating to 80 ℃, fully stirring for 8 hours, and introducing hydrogen into the hydrogenation kettle until the pressure is 7barg for reaction for 9 hours;
filtering the obtained mixed solution to remove the solid catalyst, separating out reaction liquid, pouring the reaction liquid into a crystallization kettle, setting the crystallization temperature at 80 ℃, crystallizing for 4 hours, carrying out suction filtration on the obtained mixed solution, and drying the obtained filter cake for 8 hours at 90 ℃. Thus, about 467.7g of sodium methyltaurate was obtained. The conversion rate is as follows: 96.45% and selectivity 98.17%.
Example 5
Mixing 235g of tetrakis (triphenylphosphine) palladium and 151.49g of 1- (2-diphenylphosphino-1-naphthalene) isoquinoline in 500g of distilled water, heating to 70 ℃, and stirring for 2 hours; 152.29g of cerium chloride and 218.54g of scandium chloride were dissolved in 1000g of water to prepare an aqueous solution. Adding the aqueous solution into a mixed aqueous solution of the palladium tetratriphenylphosphine and the 1- (2-diphenylphosphino-1-naphthalene) isoquinoline, and adding 108.2g of a 4A molecular sieve into the mixed aqueous solution under the stirring state to obtain slurry A;
taking a 20 wt% sodium carbonate solution as an alkaline precipitator, respectively heating the slurry A and the alkaline precipitator to 40 ℃, slowly dropwise adding the alkaline precipitator into the slurry A until the pH of the system is 10.0, and controlling the reaction temperature in the precipitation process to be 40 ℃; after the precipitation reaction is finished, aging is carried out for 4 hours at 50 ℃ to obtain slurry;
and fully filtering the slurry, washing the surface of the filter cake with deionized water, drying the filter cake at 100 ℃ for 7 hours to obtain a dried filter cake, roasting at 200 ℃ for 6 hours, crushing, tabletting and forming to obtain the catalyst.
Preparing sodium methyl taurate:
455g of sodium taurate, 250.9g of 37 percent formaldehyde aqueous solution and 22.75g of prepared catalyst are mixed and added into a hydrogenation kettle, the temperature is raised to 80 ℃, the mixture is fully stirred for 6 hours, and hydrogen is introduced into the hydrogenation kettle until the pressure is 7barg for reaction for 7 hours;
filtering the obtained mixed solution to remove the solid catalyst, separating out reaction liquid, pouring the reaction liquid into a crystallization kettle, setting the crystallization temperature at 80 ℃, crystallizing for 4 hours, carrying out suction filtration on the obtained mixed solution, and drying the obtained filter cake for 9 hours at the temperature of 100 ℃. Thus, about 482.3g of sodium methyltaurate were obtained. The conversion rate is as follows: 97.8% and selectivity 98.96%.
Claims (7)
1. A method for preparing sodium methyl taurate from sodium taurate, the method comprising: reacting sodium taurate with formaldehyde under the action of a catalyst, and carrying out aftertreatment to obtain a sodium methyl taurate product;
the catalyst is a supported composite metal organic catalyst and is expressed as Pd-Ce-Z-X/Y, wherein Z is a cocatalyst and is selected from one or more of In and Sc; x is 1- (2-diphenylphosphino-1-naphthalene) isoquinoline; y is a carrier and is selected from one or more of ordered mesoporous carbon and 4A molecular sieve;
in the catalyst, based on the total weight of the catalyst, the mass fraction of Pd is 1-10%, Ce is 10-30%, X is 30-50%, Y is 20-40%, and Z is 14-20%;
the preparation method of the catalyst comprises the following steps:
(1) dissolving Pd-containing compound and X in water, stirring for 2-4h at 60-90 deg.C, mixing thoroughly, adding Ce-containing compound and Z-containing compound into the aqueous solution, and dispersing carrier Y in the mixed aqueous solution to obtain slurry;
(2) dropwise adding an alkaline precipitator into the slurry until the pH value is 9-11, and aging to obtain slurry;
(3) carrying out post-treatment on the slurry to obtain a supported composite metal organic catalyst;
wherein, the Pd-containing compound is selected from one or more of palladium acetate, palladium chloride and tetratriphenylphosphine palladium, and the Ce-containing compound and the Z-containing compound are selected from soluble salts containing Ce and Z.
2. The method of claim 1, wherein the mass fraction of Pd is 5-8%, the mass fraction of Ce is 15-20%, the mass fraction of X is 35-40%, the mass fraction of Y is 25-30%, and the mass fraction of Z is 15-18%, based on the total weight of the catalyst.
3. The process according to claim 1, wherein the catalyst is used in an amount of 2 to 8 wt% with respect to the sodium taurate.
4. The method of claim 1, wherein the molar ratio of sodium taurate to formaldehyde is from 1:1 to 1: 2.
5. The method of claim 1, wherein the formaldehyde is a 35-40 wt% solution.
6. The process of any one of claims 1 to 5, wherein the reaction conditions comprise: firstly reacting for 5-8h at 50-100 ℃, then introducing hydrogen until the reaction pressure is 5-8barg, and continuing to react for 5-10 h.
7. The method of claim 1, wherein the post-processing comprises: crystallizing, separating and drying the solution obtained by the reaction to obtain a sodium methyl taurate product; the crystallization temperature is 60-80 ℃, and the crystallization time is 2-6 h; the drying condition is drying at 80-100 deg.C for 8-9 h.
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| CN107935892A (en) * | 2017-11-24 | 2018-04-20 | 万华化学集团股份有限公司 | A kind of method for preparing ethylenediamine base ethyl sulfonic acid sodium |
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