CN115197104B - Efficient synthesis method of methyl taurate - Google Patents

Efficient synthesis method of methyl taurate Download PDF

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CN115197104B
CN115197104B CN202210964376.9A CN202210964376A CN115197104B CN 115197104 B CN115197104 B CN 115197104B CN 202210964376 A CN202210964376 A CN 202210964376A CN 115197104 B CN115197104 B CN 115197104B
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catalyst
triflate
isethionate
aqueous solution
reactor
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CN115197104A (en
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李泽勇
刘康
孙吉龙
谭杰
户献雷
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Jiujiang Tinci Advanced Materials Co ltd
Guangzhou Tinci Materials Technology Co Ltd
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Jiujiang Tinci Advanced Materials Co ltd
Guangzhou Tinci Materials Technology Co Ltd
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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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
    • B01J2231/4283—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using N nucleophiles, e.g. Buchwald-Hartwig amination
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

The invention belongs to the technical field of daily chemical raw material preparation, and discloses a high-efficiency synthesis method of methyl taurate. The synthesis method comprises the following steps: adding isethionate aqueous solution and porous chitosan microsphere supported metal triflate catalyst into a reactor, introducing nitrogen to remove oxygen, introducing excessive methylamine into the reactor, heating the reactor to 140-200 ℃, controlling the pressure to 8-15 Mpa, stirring for reaction for 30-90 min, decompressing and flash evaporating to remove part of methylamine, cooling to 60-100 ℃ to decompress and remove the rest methylamine, filtering to recover the catalyst, and adding active carbon to decolorize to obtain the aqueous solution of the methyltaurine. The invention takes the porous chitosan microsphere supported metal triflate as the catalyst for synthesizing the methyltaurine, can be efficiently synthesized under the condition of water solvent, has high conversion rate of the isethionate, and has the advantages of environmental protection, low cost and high product quality.

Description

Efficient synthesis method of methyl taurate
Technical Field
The invention belongs to the technical field of daily chemical raw material preparation, and particularly relates to a high-efficiency synthesis method of methyl taurate.
Background
The methyl taurate is mainly used at present and is a fine chemical product with wide application, is an important raw material for producing surfactants, and can be used for synthesizing various high-added-value products such as cocoyl-N-methyl taurate, poly (sodium acryl dimethyl taurate), poly (dimethylsiloxane PEG-7 sodium acetyl methyl taurate, hydroxyethyl acrylate/sodium acryl dimethyl taurate copolymer, acryl dimethyl taurate/VP copolymer, acryl dimethyl taurate/behenate polyether-25 methacrylate cross-linked polymer and the like. These products, because of their mild nature, are commonly used as mild surfactants, primarily in laundry products. As the demand for personal care has increased, the market for mild surfactants has seen a rapid trend, and the importance of the methyl taurate series of surfactants has also increased.
In the synthesis of the methyl taurate series mild surfactant, the synthesis of the main raw material methyl taurate is key. The current common method is to prepare sodium methyl taurate by methylation of sodium taurate under high temperature and high pressure, and then purify the N-sodium methyl taurate product after acidification. The method has harsh reaction conditions, and the reaction raw material sodium taurate has fewer sources, so that the synthesis economy is not high.
The patents CN 110963946A and CN 113801039A respectively disclose that formaldehyde and halomethane are adopted to react with sodium taurate under the catalysis of a supported composite metal organic catalyst and a polymer immobilized quaternary ammonium salt catalyst to prepare sodium methyl taurate, and the problem that the source of sodium taurate serving as a reaction raw material is limited is also solved.
The patents CN 112010784A, CN 110903222A, CN 111072525A and CN 113801038A disclose the use of sodium isethionate in supercritical fluid, zn respectively 5 (CO 3 ) 2 (OH) 6 、Ni 2 ZrO 4 、Zn 5 (CO 3 ) 2 (OH) 6 /Ni 2 ZrO 4 Catalyst, zr and W modified HY molecular sieve catalyst, V 2 O 5 -WO 3 /TiO 2 And reacting with ammonia-containing gaseous substances or methylamine under the condition of a composite catalyst to obtain the sodium methyltaurine. However, the method has the defects of harsh reaction conditions or complex catalyst composition and high cost.
In addition, some scholars have studied the synthesis precaution using isethionate and methylamine as raw materials and have been applied to industrial production, but the reaction conditions are very severe, and the high temperature and high pressure are severe to the requirements of equipment and process conditions. Patent CN102675160a uses methylamine, sodium isethionate and sodium hydroxide or potassium hydroxide as catalysts as main raw materials, and adopts a pipeline reactor to prepare sodium methyltaurate, but the catalyst adopted is a homogeneous catalyst, so that subsequent separation is difficult. The reaction process temperature is 150-300 ℃, the pressure is 10-25 Mpa, and the process conditions are more severe.
At present, an alkaline catalyst (such as sodium hydroxide and potassium hydroxide) is mostly adopted in the process of preparing the methyl taurate by the reaction of the isethionate and the methylamine, higher reaction temperature and higher reaction pressure are required, the subsequent catalyst is always remained in the product, the separation cannot be effectively carried out, and the quality of the product is also affected to a certain extent. Some of these have conducted intensive studies on the catalytic system for the reaction. CN111072525B describes a Zr and W modified HY molecular sieve type catalyst, which can greatly improve the yield and selectivity of sodium N-methyltaurine, and the catalyst and ionic liquid are easy to recycle, and the catalyst has low cost and low temperature and pressure in the reaction process. CN110903222B describes heterogeneous catalysts Zn5 (CO 3) 2 (OH) 6, ni2ZrO4, zn5 (CO 3) 2 (OH) 6/Ni2ZrO4, the yield of sodium N-methyltaurine can reach 85.0-95.0%, selectivity >98%. CN113061101a describes a modified composite metal catalyst copper ammine complex modified Pr/Ho-TiO2 catalyst and/or copper ammine complex modified Pr/Ho-ZrO2 catalyst. Under the catalysis of the catalyst, the reaction temperature and the reaction pressure are obviously reduced, the device design and the safe production are facilitated, and the highest yield can be improved to more than 98%. CN113816880a describes a method for efficiently synthesizing N-methyltaurine and sodium N-methyltaurine, which uses a double-effect borophosphine ligand catalyst to catalyze and generate sodium isethionate, and continues to catalyze and generate sodium N-methyltaurine. Compared with the prior art, the raw materials of the process are cheaper and easier to obtain, the product is easy to separate and purify, the reaction conversion rate is high, the selection is good, and the total yield of two steps of synthesizing sodium isethionate and sodium taurate can reach more than 97% under the preferable condition.
As can be seen from the above patent, many researches on a method for synthesizing methyl taurate using methylamine, sodium isethionate and a catalyst as main raw materials have been focused on the attack of the catalyst. Based on the above, the inventor also provides a synthesis method of the novel catalyst and the application of the novel catalyst in the synthesis of the methyl taurate, the cost and the conversion rate are both great, and the reaction conditions are relatively mild.
Disclosure of Invention
Aiming at the defects and shortcomings of the prior art, the invention aims to provide a high-efficiency synthesis method of methyl taurate. The synthesis method of the invention takes the supported metal triflate as the catalyst, and has the advantages of lower cost and high catalytic efficiency.
The invention aims at realizing the following technical scheme:
a high-efficiency synthesis method of methyl taurate comprises the following steps:
adding isethionate aqueous solution and porous chitosan microsphere supported metal triflate catalyst into a reactor, introducing nitrogen to remove oxygen, introducing excessive methylamine into the reactor, heating the reactor to 140-200 ℃, controlling the pressure to 8-15 Mpa, stirring for reaction for 30-90 min, decompressing and flash evaporating to remove part of methylamine, cooling to 60-100 ℃ to decompress and remove the rest methylamine, filtering to recover the catalyst, and adding quantitative activated carbon to decolorize to obtain the aqueous solution of the methyltaurine.
Further, the isethionate refers to sodium isethionate or ammonium isethionate.
Further, the mass concentration of the aqueous solution of the isethionate is 5-40%.
Further, the porous chitosan microsphere supported metal triflate catalyst is prepared by the following method:
(1) Preparing porous chitosan microspheres: dripping chitosan acetic acid solution into alkaline aqueous solution containing glutaraldehyde crosslinking agent, stirring and reacting at 20-60 ℃, filtering, washing and drying the product to obtain porous chitosan microspheres;
(2) Preparing a porous chitosan microsphere supported metal triflate catalyst: adding the porous chitosan microspheres obtained in the step (1) into a metal triflate solution, stirring and reacting at the temperature of 30-80 ℃, and filtering, washing and drying the product to obtain the porous chitosan microsphere supported metal triflate catalyst.
Further, the mass concentration of the chitosan acetic acid solution in the step (1) is 1% -10%.
Further, the alkaline aqueous solution in the step (1) is NaOH solution with the mass concentration of 1% -4%.
Further, the metal triflate solution in the step (2) refers to at least one of zinc triflate, iron triflate, aluminum triflate and magnesium triflate solution; more preferably a zinc triflate solution.
Further, the addition amount of the porous chitosan microsphere supported metal triflate catalyst is 0.5-2.5% of the mass of the aqueous solution of the isethionate.
Further characterized in that the temperature in the reactor is 140-180 ℃ and the pressure is 8-10 Mpa; the stirring reaction time is 60-80 min.
Further, the aqueous solution of methyl taurate salt is dried to obtain a solid product of methyl taurate salt.
Compared with the prior art, the invention has the beneficial effects that:
(1) The invention takes the porous chitosan microsphere supported metal triflate as the catalyst for synthesizing the methyltaurine, can be efficiently synthesized under the condition of water solvent, has high conversion rate of the isethionate, and has the advantages of environmental protection, low cost and high product quality.
(2) The porous chitosan microsphere is used as a carrier of metal salt of trifluoromethane sulfonate, and the coordination function and the porous adsorption function of amino groups in the chitosan microsphere are utilized, so that the catalyst has high load and stable load, and still has higher catalytic activity after repeated use for many times.
Detailed Description
The present invention will be described in further detail with reference to examples, but embodiments of the present invention are not limited thereto.
Example 1
The efficient synthesis method of the methyl taurate comprises the following steps:
500g of sodium isethionate aqueous solution with the mass concentration of 25% and 10g of porous chitosan microsphere-loaded zinc triflate catalyst are added into a pressure-resistant reactor with a stirring device, nitrogen is introduced to deoxidize, 393g of methylamine is introduced again, the temperature is raised to 160 ℃ for stirring reaction, methylamine is introduced from the bottom of the reactor through a circulating aeration pipe and circulates from the top of the reactor, and the positive pressure in the reactor is maintained to be 9Mpa by introducing methylamine through linkage control in the reaction process. After the reaction is carried out for 80min, the reaction is completed, a decompression valve is opened to decompress and flash the flash evaporation to receive part of methylamine and water, the chilled water is cooled to 70 ℃, then the residual methylamine and water are continuously removed in vacuum, then the catalyst is filtered and recovered, and activated carbon with the mass of 0.5% of the product is added into a reactor for decolorization treatment, thus obtaining the sodium methyltaurine water solution with the mass concentration of about 40%.
The content of residual sodium isethionate in the product was 2.12g by HPLC, and the content of the target product sodium methyltaurine was 133.47g. The conversion of isethionate was 98.3%. The obtained sodium methyltaurine aqueous solution is further dried in vacuum to obtain a sodium methyltaurine solid product.
The conversion of isethionate at different reaction times was studied, and the content of residual sodium isethionate in the products obtained at the reaction times of 20min, 40min, 60min, 80min and 100min in this order was measured, and the corresponding conversion was calculated, and the results are shown in table 1 below.
TABLE 1
Reaction time 20min 40min 60min 80min 100min
Conversion rate 63.2％ 80.5％ 93.6％ 98.3％ 98.9％
As can be seen from the results in Table 1, a higher conversion can be achieved in 80 minutes.
The porous chitosan microsphere supported zinc triflate catalyst of the embodiment is prepared by the following method:
dripping chitosan acetic acid solution with the mass concentration of 4% (the mass concentration of acetic acid is 1%) into 2% sodium hydroxide aqueous solution containing glutaraldehyde crosslinking agent, stirring and reacting at 40 ℃, filtering the product, washing with deionized water, and vacuum drying to obtain porous chitosan microspheres; then adding the obtained porous chitosan microsphere into 25% mass concentration zinc triflate aqueous solution, stirring and reacting for 2 hours at 40 ℃, filtering the product, washing with deionized water, and vacuum drying to obtain the porous chitosan microsphere supported zinc triflate catalyst. The zinc content of the catalyst was 1.89wt% as measured by ICP-MS.
After the porous chitosan microsphere supported zinc triflate catalyst obtained by the embodiment is repeatedly used for 10 times, the conversion rate of the isethionate can still reach 97.5% after the reaction is carried out for 80 minutes. The catalyst has good stability and high catalytic activity.
Comparative example 1
The comparative example uses a polystyrene microsphere supported zinc triflate catalyst instead of the porous chitosan microsphere supported zinc triflate catalyst of example 1. The polystyrene microsphere supported zinc triflate catalyst is prepared by the following method:
polystyrene microsphere (commercially available, containing mesoporous structure) is added into 25% mass concentration zinc triflate aqueous solution, stirring reaction is carried out for 2 hours at 40 ℃, and the product is filtered, washed by deionized water and dried in vacuum to obtain the zinc triflate catalyst loaded by the polystyrene microsphere. The zinc content of the catalyst was 0.47wt% as measured by ICP-MS.
The zinc triflate catalyst supported by the polystyrene microsphere of the comparative example was used to catalyze the synthesis of methyltaurine salt in the manner of example 1, and the conversion of isethionate salt at various reaction times is shown in Table 2 below.
TABLE 2
Reaction time 20min 40min 60min 80min 100min
Conversion rate 21.2％ 27.4％ 33.1％ 39.4％ 48.5％
As can be seen from the comparison result of the embodiment 1, compared with the mesoporous polystyrene microsphere, the porous chitosan microsphere is used as the carrier of the metal salt of the trifluoromethane sulfonic acid, the catalyst loading capacity and the catalytic activity are obviously improved, and the catalyst loading capacity and the loading stability are obviously improved due to the fact that a large amount of amino groups in and on the micropores of the porous chitosan microsphere have strong coordination effect on the metal salt of the trifluoromethane sulfonic acid and are combined with the porous adsorption effect.
Example 2
This example is a catalytic activity study of different metal salt catalysts. Porous chitosan microsphere-supported ferric triflate, aluminum triflate, and magnesium triflate catalysts were prepared, respectively, according to the method of example 1. And the synthesis of methyltaurine salt was carried out as in example 1. The conversion of isethionate at different reaction times is shown in table 3 below.
TABLE 3 Table 3
Reaction time/conversion 20min 40min 60min 80min 100min
Iron triflate 59.0％ 72.6％ 87.2％ 93.9％ 98.1％
Aluminum triflate 54.3％ 68.7％ 81.5％ 89.4％ 95.7％
Magnesium triflate salt 48.8％ 59.1％ 74.1％ 82.5％ 91.4％
As can be seen from the results in Table 1 and Table 3, the porous chitosan microsphere supported metal triflate catalyst obtained by the invention has good catalytic activity, wherein the porous chitosan microsphere supported zinc triflate has the highest catalytic activity.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.

Claims (8)

1. The synthesis method of the methyl taurate is characterized by comprising the following steps:
adding an aqueous solution of isethionate and a porous chitosan microsphere supported metal triflate catalyst into a reactor, introducing nitrogen to remove oxygen, introducing excessive methylamine into the reactor, heating the reactor to 140-200 ℃, controlling the pressure to 8-15 mpa, stirring for reacting for 30-90 min, decompressing and flash evaporating to remove part of methylamine, cooling to 60-100 ℃ to decompress and remove the rest methylamine, filtering to recover the catalyst, and adding quantitative activated carbon into the reactor for decoloring treatment to obtain an aqueous solution of methyl taurate;
the porous chitosan microsphere supported metal triflate catalyst is prepared by the following steps:
(1) Preparing porous chitosan microspheres: dripping chitosan acetic acid solution into alkaline aqueous solution containing glutaraldehyde crosslinking agent, stirring and reacting at 20-60 ℃, filtering, washing and drying the product to obtain porous chitosan microspheres;
(2) Preparing a porous chitosan microsphere supported metal triflate catalyst: adding the porous chitosan microspheres obtained in the step (1) into a metal triflate solution, stirring and reacting at the temperature of 30-80 ℃, and filtering, washing and drying a product to obtain the porous chitosan microsphere supported metal triflate catalyst;
the metal triflate solution in the step (2) refers to at least one of zinc triflate, iron triflate, aluminum triflate and magnesium triflate solution.
2. The method for synthesizing methyltaurine salt according to claim 1, wherein the isethionate salt is sodium isethionate or ammonium isethionate.
3. The method for synthesizing the methyltaurine salt according to claim 2, wherein the mass concentration of the aqueous solution of the isethionate salt is 5% -40%.
4. The method for synthesizing the methyltaurine salt according to claim 1, wherein the mass concentration of the chitosan acetic acid solution in the step (1) is 1% -10%; the alkaline aqueous solution is NaOH solution with the mass concentration of 1% -4%.
5. The method for synthesizing methyltaurine salt according to claim 1, wherein the metal triflate solution is a zinc triflate solution.
6. The method for synthesizing the methyltaurine salt according to claim 1, wherein the addition amount of the porous chitosan microsphere supported metal triflate catalyst is 0.5% -2.5% of the mass of the aqueous solution of the isethionate.
7. The method for synthesizing the methyltaurine salt according to claim 1, wherein the temperature in the reactor is 140-180 ℃ and the pressure is 8-10 mpa; the stirring reaction time is 60-80 min.
8. The method for synthesizing methyltaurine salt according to claim 1, wherein said aqueous solution of methyltaurine salt is dried to obtain a solid methyltaurine salt product.
CN202210964376.9A 2022-08-11 2022-08-11 Efficient synthesis method of methyl taurate Active CN115197104B (en)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111072525A (en) * 2019-12-26 2020-04-28 万华化学集团股份有限公司 Preparation method of N-methyl sodium taurate

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111072525A (en) * 2019-12-26 2020-04-28 万华化学集团股份有限公司 Preparation method of N-methyl sodium taurate

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* Cited by examiner, † Cited by third party
Title
Fe(OTf)3-catalyzed tandem Meyer-Schuster rearrangement/intermolecular hydroamination of 3-aryl propargyl alcohols for the synthesis of acyclic β-Aminoketones;Ruiheng Tao等;Tetrahedron;第73卷;1762 -1768 *
壳聚糖多孔微球负载PdCl2选择性催化氢化氯代硝基苯的研究;陈水平等;功能高分子学报;第16卷(第1期);6-12 *

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