CN113801038A - Method for preparing N-methyl sodium taurate - Google Patents
Method for preparing N-methyl sodium taurate Download PDFInfo
- Publication number
- CN113801038A CN113801038A CN202010536229.2A CN202010536229A CN113801038A CN 113801038 A CN113801038 A CN 113801038A CN 202010536229 A CN202010536229 A CN 202010536229A CN 113801038 A CN113801038 A CN 113801038A
- Authority
- CN
- China
- Prior art keywords
- reaction
- catalyst
- temperature
- sodium
- filter cake
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- 229940104256 sodium taurate Drugs 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 20
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- QEOWFDYSNYCPRK-UHFFFAOYSA-N OCC[Na] Chemical compound OCC[Na] QEOWFDYSNYCPRK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 5
- 229940045998 sodium isethionate Drugs 0.000 claims description 7
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- CAQWNKXTMBFBGI-UHFFFAOYSA-N C.[Na] Chemical compound C.[Na] CAQWNKXTMBFBGI-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 7
- 239000012065 filter cake Substances 0.000 description 26
- 238000010438 heat treatment Methods 0.000 description 22
- 239000000843 powder Substances 0.000 description 21
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 18
- 238000001816 cooling Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 10
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 7
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000000227 grinding Methods 0.000 description 6
- 238000007069 methylation reaction Methods 0.000 description 6
- 235000006408 oxalic acid Nutrition 0.000 description 6
- 238000007873 sieving Methods 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 208000012839 conversion disease Diseases 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 4
- 238000009776 industrial production Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 229940104261 taurate Drugs 0.000 description 4
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- -1 dimethyl taurate Chemical compound 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000006268 reductive amination reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- AOSFMYBATFLTAQ-UHFFFAOYSA-N 1-amino-3-(benzimidazol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(O)CN)C=NC2=C1 AOSFMYBATFLTAQ-UHFFFAOYSA-N 0.000 description 1
- LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZDSCFBCGDDCJFZ-UHFFFAOYSA-N 2-(methylamino)ethanesulfonic acid;sodium Chemical compound [Na].CNCCS(O)(=O)=O ZDSCFBCGDDCJFZ-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000006742 Retro-Diels-Alder reaction Methods 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 238000010812 external standard method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KKDONKAYVYTWGY-UHFFFAOYSA-M sodium;2-(methylamino)ethanesulfonate Chemical compound [Na+].CNCCS([O-])(=O)=O KKDONKAYVYTWGY-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
Classifications
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/30—Tungsten
-
- 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
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
Landscapes
- 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)
Abstract
The invention relates to a method for preparing N-methyl sodium taurate, which takes methylamine and hydroxyethyl sodium sulfonate as raw materials and uses a catalyst V2O5‑WO3/TiO2Under the action, water is used as a solvent to synthesize the N-methyl sodium taurate. The method for preparing the N-methyl sodium taurate has the advantages of high atom utilization rate, high selectivity, mild reaction conditions, easy operation and good controllability, and is an environment-friendly preparation method.
Description
Technical Field
The invention relates to a method for preparing N-methyl sodium taurate, belonging to the field of fine chemical engineering.
Technical Field
N-sodium methyltaurate, also known as sodium methyltaurate, is an important derivative of taurine and can be used as an intermediate in daily chemistry and pharmacy. In the field of daily chemicals, the method can be used for synthesizing various high value-added products such as cocoyl-N-methyl taurate, polyacryl dimethyl taurate, polydimethylsiloxane PEG-7 acetyl methyl taurate, hydroxyethyl acrylate/propylene acyl dimethyl taurate copolymer and the like, the products are generally regarded as mild surfactants due to the mild characteristics, the market of the mild surfactants shows a rapid growth trend along with the increasing demand of people on the cortex in the aspect of personal care, and N-methyl taurate series surfactants are some important products.
In the synthesis of N-methyl sodium taurate series mild surfactants, the synthesis of the main raw material N-methyl sodium taurate is a key synthesis reaction, and the synthesis method is basically consistent with the conventional amino acid N-methylation method. To date, there have been many reports of N-methylation methods for the synthesis of amino acids, and commonly used methods include direct N-methylation methods, reductive amination methods, and methods for reconversion to N-methylated products via oxazolidinone intermediates. In addition, there are also specific methods such as reductive alkylation of azide-based compounds, N-methylation using N-nosyl protection and grafting, and retro-Diels-Alder reaction using an imide nitrogen cation to obtain the desired product. Among these methods, some require multiple steps to complete (such as reductive amination), which tends to result in lower overall reaction yields; still other processes result in racemization of some of the product (e.g., direct N-methylation, oxazolidinone intermediate, etc.) to yield unwanted by-products; there are also processes which use relatively expensive starting materials (e.g. direct N-methylation using CH as the starting material3I. Oxazolidinone intermediate method, etc.), wherein the conditions adopted by some methods are relatively harsh, which is not favorable for industrial production. Although some of these methods have been used in industrial production, further optimization is still needed.
In summary, in the industrial production of the synthetic sodium N-methyltaurate, there is still a need to develop a method which can obtain high yield, mild reaction conditions and low raw material cost, so as to reduce the industrial production cost of the sodium N-methyltaurate.
CN106674061 discloses the preparation of N-methyltaurate by the reaction of N-methylacetamide with concentrated sulfuric acid, which, although the reaction conditions are improved compared with the conventional methods, still has the problems of limited raw material sources, high cost, low conversion rate, etc.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides the method for preparing the N-methyl sodium taurate, which has the advantages of high utilization rate of raw materials, high selectivity, mild reaction conditions, easy operation and good controllability, and is an environment-friendly preparation method.
The invention is realized by the following technical scheme:
the synthetic route of the invention is as follows:
the invention provides a method for preparing N-methyl sodium taurate, which adopts methylamine and hydroxyethyl sodium sulfonate as raw materials and generates the N-methyl sodium taurate by reaction under the action of a catalyst.
In the invention, the molar ratio of methylamine to sodium isethionate is 1-10: 1, preferably 1 to 3: 1, more preferably 1 to 2: 1;
in the invention, the reaction is carried out in a solvent, wherein the solvent is preferably water, and accounts for 40-80 wt%, preferably 50-80 wt%, and more preferably 60-80 wt% of the total mass of the reactants.
In the invention, the reaction temperature is-5-50 ℃, and the preferable reaction temperature is as follows: 10 ℃ to 50 ℃, more preferably 25 ℃ to 45 ℃.
In the invention, the reaction time is 60-300 min, preferably 120-300 min, and more preferably 120-240 min.
In the present invention, the reaction pressure is 0.1 to 8.0MpaG, preferably 0.1 to 5.0MpaG, and more preferably 0.1 to 3.0 MpaG.
In the present invention, the catalyst is V2O5-WO3/TiO2The composite catalyst is prepared by the steps of,the addition amount of the catalyst is 0.1-5.0 wt% of the mass of the hydroxyethyl sodium sulfonate, preferably 0.1-2.0 wt%, and more preferably 0.1-1.0 wt%.
Among the catalysts, WO3And V2O5The mass ratio of (A) to (B) is preferably 7.5 to 9.5: 1.
In some preferred embodiments of the invention, the catalyst is V2O5-WO3/TiO2Commercially available products may be purchased or self-made, and in some preferred embodiments,
the preparation method of the catalyst comprises the following steps:
dissolving a certain amount of ammonium metavanadate in an oxalic acid solution, and stirring until the ammonium metavanadate is dissolved; then adding a certain amount of TiO2Fully stirring the powder, standing the powder at room temperature for 24-48 h, filtering the powder under reduced pressure, washing a filter cake with 20ml of deionized water for 3-5 times, drying the filter cake in an oven at 80-100 ℃ for 10-15 h, then placing the dried filter cake in a muffle furnace, heating the filter cake to 250-300 ℃ from the room temperature at the heating rate of 2-5 ℃/min, keeping the temperature for 1-5 h, heating the filter cake to 500-600 ℃ at the heating rate of 2-5 ℃/min, keeping the temperature for 3-8 h, taking the filter cake out after cooling, grinding and sieving the filter cake to obtain a (80-120) mesh part, and obtaining the V-shaped particle with the granularity of V2O5/TiO2And (3) powder.
Dissolving a certain amount of ammonium tungstate in an oxalic acid solution, and stirring until the ammonium tungstate is dissolved; then V is added2O5/TiO2Fully stirring the powder, standing at room temperature for 24-48 h, drying an oven at 80-100 ℃ for 10-15 h, then placing the powder in a muffle furnace, heating the powder to 250-300 ℃ from room temperature at a heating rate of 2-5 ℃/min, keeping the temperature for 1-5 h, heating the powder to 500-600 ℃ at a heating rate of 2-5 ℃/min, keeping the temperature for 3-8 h, cooling, taking out the powder, grinding and sieving the powder to obtain a (80-120) mesh part, and obtaining a V2O5-WO3/TiO2A catalyst.
Preferably, m (WO)3):m(V2O5)＝7.5～9.5:1
Compared with the prior art, the invention has the following beneficial effects:
the synthesis method disclosed by the invention can improve the utilization rate of raw materials, is high in selectivity, mild in reaction conditions, easy to separate and purify the product, simple to operate and good in controllability, and is an environment-friendly preparation method. Moreover, the cost of the selected raw materials is low, the industrialization cost can be greatly reduced, and the method is convenient to popularize.
The specific implementation mode is as follows:
the present invention will be described in detail with reference to specific examples. The following examples will assist those skilled in the art in further understanding the invention, but are not intended to limit the invention in any way. It should be noted that variations and modifications can be made by persons skilled in the art without departing from the spirit of the invention. All falling within the scope of the present invention.
The following measures were used in the following examples to determine the analytical selectivity and conversion:
the product in the process is analyzed by liquid chromatography equipped with an ultraviolet detector, wherein the liquid chromatography is 1200 series of Agilent company and is equipped with a C18 liquid chromatography column, the column temperature is set to be 40 ℃, acetonitrile and 0.05mol/L NaH2PO4 solution are used as mobile phases, the flow rate is 1.0mL/min, the detection is carried out at the wavelength of 360nm by the 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.
The NMR was model Bruke 400.
Example 1
Preparation of catalyst a:
dissolving 10.0g of ammonium metavanadate in 50ml of 4.5 wt% oxalic acid solution, and stirring until the ammonium metavanadate is dissolved; then 3.0g of TiO was added2Fully stirring the powder, standing the powder at room temperature for 24 hours, filtering the powder under reduced pressure, washing a filter cake for 3 times by using 20ml of deionized water, placing the filter cake in an oven to dry the filter cake for 12 hours at 90 ℃, then placing the filter cake in a muffle furnace to heat the filter cake to 280 ℃ from room temperature at the heating rate of 3 ℃/min, keeping the temperature for 3 hours, then reaching 550 ℃ at the heating rate of 3 ℃/min, keeping the temperature for 4 hours, taking the filter cake out after cooling, grinding and sieving the filter cake to obtain a (80-120) mesh part, and obtaining the V2O5/TiO2And (3) powder.
Dissolving 15.0g of ammonium tungstate in 50ml of 4.5 wt% oxalic acid solution, and stirring until the ammonium tungstate is dissolved; then 3.0g of V were added2O5/TiO2Fully stirring the powder, standing for 24 hours at room temperature, filtering under reduced pressure, washing a filter cake for 3 times by using 20ml of deionized water, drying the filter cake in an oven at 90 ℃ for 10 hours, then placing the dried filter cake in a muffle furnace, heating the filter cake from the room temperature to 280 ℃ at the heating rate of 3 ℃/min, keeping the temperature for 3 hours, then reaching the temperature of 550 ℃ at the heating rate of 3 ℃/min, keeping the temperature for 4 hours, cooling, taking out the cooled filter cake, grinding and sieving the powder to obtain a (80-120) mesh part, and thus obtaining the V-shaped particle2O5-WO3/TiO2A catalyst.
The vanadium content of the catalyst was 0.22 wt% and the tungsten content was 2.61 wt% as measured by inductively coupled plasma mass spectrometry (ICP-MS).
Preparation of catalyst B:
dissolving 12.2g of ammonium metavanadate in 50ml of 4.5 wt% oxalic acid solution, and stirring until the ammonium metavanadate is dissolved; then 5.0g of TiO was added2Fully stirring the powder, standing the powder at room temperature for 48 hours, filtering the powder under reduced pressure, washing a filter cake for 4 times by using 20ml of deionized water, drying the filter cake in an oven at 100 ℃ for 10 hours, then placing the dried filter cake in a muffle furnace, heating the filter cake from the room temperature to 300 ℃ at the heating rate of 5 ℃/min, keeping the temperature for 5 hours, then reaching the temperature of 600 ℃ at the heating rate of 2 ℃/min, keeping the temperature for 7 hours, taking the dried filter cake out after cooling, grinding and sieving the filter cake to obtain a (80-120) mesh part, and thus obtaining the V-shaped particle2O5/TiO2And (3) powder.
Dissolving 16.5g of ammonium tungstate in 50ml of 5.2 wt% oxalic acid solution, and stirring until the ammonium tungstate is dissolved; 4.0g of V are then added2O5/TiO2Fully stirring the powder, standing at room temperature for 48h, filtering under reduced pressure, washing the filter cake with 20ml of deionized water for 3 times, drying in an oven at 80 ℃ for 15h, then placing in a muffle furnace, heating from room temperature to 250 ℃ at a heating rate of 2 ℃/min, keeping the temperature for 5h, then reaching 500 ℃ at a heating rate of 5 ℃/min, keeping the temperature for 8h, cooling, taking out, grinding, sieving to obtain a (80-120) mesh part, and thus obtaining the V-shaped particle2O5-WO3/TiO2A catalyst.
The vanadium content of the catalyst was 0.27 wt% and the tungsten content was 2.89 wt% as measured by inductively coupled plasma mass spectrometry (ICP-MS).
Example 2
Adding 486.6g of 30.4 wt% sodium isethionate solution into a reactor, adding 0.75g of catalyst A, replacing with N2, adding 34.1g of methylamine into the system, controlling the temperature at 35 ℃, filling N2 into the system, controlling the pressure in the system to be 0.2MpaG, carrying out heat preservation reaction for 150min, cooling and sampling, and detecting the mass of N-methyltaurine sodium to be 152.9g by LC. The conversion of the reaction was 96.7% and the selectivity 98.2%.
1HNMR(400MHz,D2O)δ3.55(t,J＝7.1Hz,2H),3.24(s,3H),3.13(t,J＝7.1Hz,2H).
Example 3
Adding 378.3g of 46.99 wt% sodium isethionate solution into a reactor, adding 1.778g of catalyst and N2 for replacement, adding 123.0g of methylamine into the system, controlling the temperature at 35 ℃, filling N2 into the system, controlling the pressure in the system at 7.8MpaG, carrying out heat preservation reaction for 285min, and then cooling and sampling.
The mass of the N-methyltaurate detected by LC was 118.1 g. The reaction conversion was 73.2% and selectivity was 83.4%.
Example 4
536.7g of 17.39 wt% sodium isethionate solution is added into a reactor, 0.93g of catalyst B and N2 are added for replacement, 39.1g of methylamine is added into the system, the temperature is controlled at 40 ℃, N2 is filled into the system, the pressure in the system is controlled at 2.5MpaG, and the temperature is reduced and the sample is taken after the reaction is kept for 150 min.
The mass of the N-methyltaurate sodium salt detected by LC is 100.1 g. The conversion of the reaction was 99.58% and the selectivity was 99.02%.
Example 5
Adding 1199.6g of 37.04 wt% sodium isethionate solution into a reactor, adding 1.11g of catalyst, replacing with N2, adding 149.1g of methylamine into the system, controlling the temperature at 10 ℃, filling N2 into the system, keeping the pressure in the system at 0.1MpaG, keeping the temperature for reaction for 100min, and then cooling and sampling.
The mass of the sodium N-methyltaurate detected by LC was 284.3 g. The reaction conversion was 64.67% with selectivity 90.93%.
Example 6
Adding 510.9g of 29.0 wt% sodium isethionate solution into a reactor, adding 7.11g of catalyst B and N2 for replacement, adding 295.2g of methylamine into the system, controlling the temperature at 45 ℃, filling N2 into the system, controlling the pressure in the system to be 7.5MpaG, carrying out heat preservation reaction for 200min, and then cooling and sampling.
The mass of the sodium N-methyltaurate detected by LC was 124.6 g. The reaction conversion was 99.58% and selectivity was 77.62%.
Comparative example 1
Adding 73.1g of N-methylacetamide into a reactor, adding 392g of 50 percent sulfuric acid into the reactor within 2 hours, heating to control the reaction temperature in the reactor to be about 100 ℃, reacting for 18 hours, then adding 67.4g of 50 percent ammonium bisulfite into the system, reacting for 12 hours at the temperature of about 100 ℃ under normal pressure, cooling to the temperature T in the reactor to be less than 50 ℃, then adding 100ml of 30 percent hydrogen peroxide into the reactor, reacting for 2 hours, concentrating and centrifuging the product to obtain 106.3g of solid, putting the solid into 500ml of 1, 2-dichloroethane, heating and refluxing for 2 hours, cooling to 50-60 ℃, adding 55g of sodium bicarbonate, stirring uniformly, adding 10ml of 10% ammonium chloride aqueous solution, heating and refluxing for 4h, cooling to room temperature, carrying out centrifugal filtration to obtain N-methyl sodium taurate, wherein the titration content is 88% under alkaline conditions, and the mass of the N-methyl sodium taurate is 99.56g by LC detection. The reaction conversion was 68.50% with a selectivity of 90.2%.
Claims (8)
1. A method for preparing N-methyl sodium taurate is characterized in that methylamine and hydroxyethyl sodium sulfonate are adopted as raw materials and react under the action of a catalyst to generate the methyl sodium taurate.
2. The method according to claim 1, wherein the molar ratio of methylamine to sodium isethionate is 1 to 10: 1, preferably 1 to 3: 1, more preferably 1 to 2: 1.
3. the process according to claim 1 or 2, characterized in that the reaction is carried out in a solvent, preferably water;
the solvent accounts for 40-80 wt%, preferably 50-80 wt%, and more preferably 60-80 wt% of the total mass of the reactants.
4. A method according to any of claims 1 to 3, characterized in that the reaction temperature during the synthesis is preferably-5 ℃ to 50 ℃, preferably 10 ℃ to 50 ℃, more preferably 25 ℃ to 45 ℃.
5. The process according to any one of claims 1 to 4, wherein the reaction time is preferably 60 to 300min, preferably 120 to 300min, more preferably 120 to 240 min.
6. The process according to any one of claims 1 to 5, wherein the reaction pressure is 0.1 to 8.0MpaG, preferably 0.1 to 5.0MpaG, more preferably 0.1 to 3.0 MPa.
7. The process of any one of claims 1 to 6, wherein the catalyst is V2O5-WO3/TiO2The addition amount of the composite catalyst is 0.1-5.0 wt% of the mass of the hydroxyethyl sodium sulfonate, preferably 0.1-2.0 wt%, and more preferably 0.1-1.0 wt%.
8. The method according to any one of claims 1 to 7,
among the catalysts, WO3And V2O5The mass ratio of (A) to (B) is 7.5-9.5: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010536229.2A CN113801038B (en) | 2020-06-12 | 2020-06-12 | Method for preparing N-methyl sodium taurate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010536229.2A CN113801038B (en) | 2020-06-12 | 2020-06-12 | Method for preparing N-methyl sodium taurate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113801038A true CN113801038A (en) | 2021-12-17 |
| CN113801038B CN113801038B (en) | 2024-02-02 |
Family
ID=78944034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010536229.2A Active CN113801038B (en) | 2020-06-12 | 2020-06-12 | Method for preparing N-methyl sodium taurate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113801038B (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB815167A (en) * | 1957-01-14 | 1959-06-17 | Ici Ltd | New n-alkyl taurines |
| JPH0421666A (en) * | 1990-05-17 | 1992-01-24 | Tosoh Corp | Method for purifying metal aminoethylsulfonate |
| JP2002234868A (en) * | 2001-02-08 | 2002-08-23 | Rekkutekku Laboratories Kk | Method for producing acyltaurine salt |
| 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 |
| CN110903222A (en) * | 2019-12-16 | 2020-03-24 | 万华化学集团股份有限公司 | Preparation method of N-methyl sodium taurate |
| 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 |
-
2020
- 2020-06-12 CN CN202010536229.2A patent/CN113801038B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB815167A (en) * | 1957-01-14 | 1959-06-17 | Ici Ltd | New n-alkyl taurines |
| JPH0421666A (en) * | 1990-05-17 | 1992-01-24 | Tosoh Corp | Method for purifying metal aminoethylsulfonate |
| JP2002234868A (en) * | 2001-02-08 | 2002-08-23 | Rekkutekku Laboratories Kk | Method for producing acyltaurine salt |
| 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 |
| CN110903222A (en) * | 2019-12-16 | 2020-03-24 | 万华化学集团股份有限公司 | Preparation method of N-methyl sodium taurate |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113801038B (en) | 2024-02-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109972165B (en) | Electrochemical preparation method of β -trifluoromethyl amide compound | |
| CN111960948B (en) | Synthesis process of tetrabutylammonium bromide | |
| EP1770084B1 (en) | Method for producing (z)-1-phenyl-1-diethylaminocarbonyl-2-aminomethyl cyclopropane hydrochloride | |
| CN109608365B (en) | Preparation method of taurine | |
| CN104003863A (en) | Green synthesis method for benzoin | |
| CN114149376B (en) | Preparation method of tris (2-hydroxyethyl) isocyanurate | |
| CN113603574B (en) | Method for catalyzing catalytic oxidation reaction of cyclopentene by using short-site silicotungstic heteropolyacid salt catalyst | |
| CN111072525B (en) | Preparation method of N-methyl sodium taurate | |
| CN113801038A (en) | Method for preparing N-methyl sodium taurate | |
| KR100842793B1 (en) | Method for producing ?-methyl-??-nitroguanidine | |
| CN110256297B (en) | Preparation method of N-Boc- (R) -2-amino-4, 4-dimethylpentanoic acid | |
| CN111574384B (en) | Preparation method of chiral 1-amino-2-propanol | |
| AU2012343935A1 (en) | Method for producing and purifying salts of acrylamido-2-methylpropane sulfonic acid | |
| CN113801039A (en) | Method for preparing N-methyl sodium taurate | |
| CN113999171A (en) | Synthesis method of high-content dipyrithione | |
| CN105777507A (en) | Method for synthesizing methoxy acetone | |
| CN115304541B (en) | Preparation method of 3-chloro-4- (2-pyridylmethoxy) aniline | |
| CN110963946A (en) | Preparation method of sodium methyl taurate | |
| CN110724098A (en) | Synthetic method of 5, 7-dichloro-1, 2,3, 4-tetrahydroisoquinoline-6-carboxylic acid hydrochloride | |
| TW201943708A (en) | Method for preparing 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazole carboxamide | |
| CN110563591B (en) | Environment-friendly synthesis method of N, N, N' -trimethylethylenediamine | |
| CN112624968B (en) | Synthetic method of 5-amino-3-cyanopyridine methyl formate hydrochloride | |
| CN114369069B (en) | Preparation method of quizalofop-p-ethyl compound intermediate | |
| CN115947675B (en) | Rasagiline intermediate and preparation method and application thereof | |
| CN113816880B (en) | Method for efficiently synthesizing N-methyl taurine and N-methyl sodium taurine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |