CN113801039A - Method for preparing N-methyl sodium taurate - Google Patents
Method for preparing N-methyl sodium taurate Download PDFInfo
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- CN113801039A CN113801039A CN202010536237.7A CN202010536237A CN113801039A CN 113801039 A CN113801039 A CN 113801039A CN 202010536237 A CN202010536237 A CN 202010536237A CN 113801039 A CN113801039 A CN 113801039A
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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
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- 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
- B01J31/068—Polyalkylene glycols
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
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Abstract
The invention provides a method for preparing sodium methyl taurate, which takes halogenated methane and sodium taurate as raw materials, takes immobilized catalyst quaternary ammonium salt as a catalyst and water as a solvent to synthesize the sodium methyl taurate by a one-step method. The method has the advantages of high atom utilization rate, thorough reaction, no complicated separation process of the current process, low energy consumption and easy operation; the reaction condition is mild, the reaction condition under the catalysis is easy to meet, the equipment requirement is low, the controllability is good, the separation is easy, the product purity is high, and the preparation method is green and environment-friendly.
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
The N-methyl sodium taurate is a widely used fine chemical product, is an important raw material for producing daily chemical intermediates and textile auxiliaries and surfactants, and is mainly used in washing and caring products. At present, the most common method is to methylate sodium taurate under high temperature and high pressure to prepare sodium methyl taurate, and then purify the sodium N-methyl taurate product after acidification treatment. The method has harsh reaction conditions, more raw materials are remained due to incomplete methylation, the yield is low, the operation is complex, and the industrial reaction and the extraction have great problems.
Patent CN106674061A mentions that the reaction conditions of the method for preparing N-methyl sodium taurate by reacting N-methylacetamide with concentrated sulfuric acid are improved compared with the reaction conditions of the conventional method, but the problems of limited raw material sources, high cost, low conversion rate and the like exist.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a method for preparing sodium methyl taurate, which has the advantages of high utilization rate of raw materials, thorough reaction, no complicated separation process of the current process, low energy consumption and easy operation; the reaction condition is mild, and the product purity is high.
The invention is realized by the following technical scheme:
a method for preparing N-methyl sodium taurate, take halogenated methane, sodium taurate as raw materials, regard quaternary ammonium salt as catalyst, prepare N-methyl sodium taurate.
In the method, the methyl halide is one or more of methyl iodide, methyl bromide or methyl chloride;
in the method, the molar ratio of the sodium taurate and the halogenated methane as raw materials is 0.05-2.0:1, preferably 0.05-1.0: 1, and more preferably 0.2-1: 1;
in the method, the quaternary ammonium salt catalyst is a polymer immobilized quaternary ammonium salt catalyst;
in the method, the quaternary ammonium salt catalyst carrier is polystyrene immobilized polyethylene glycol resin;
the preparation method of the catalyst in the method comprises the following steps:
soaking 1 part of polystyrene-supported polyethylene glycol resin in 4-6 parts (by mass) of organic solvent overnight, adding 1-2 parts of alkaline catalyst, distilling to remove most of the organic solvent, supplementing 4-5 parts of organic solvent, adding 5-10 parts of dihaloalkane, reacting for 5-8 h under a reflux state, washing, and drying.
And adding 1 part of dried resin and 2-3 parts of tertiary amine into 4-6 parts of organic solvent, reacting for 12-24 h, washing and drying.
Preferably, the mixture is washed by 1-2 parts of ethanol and water respectively.
The above-mentioned parts are all parts by mass.
Preferably, the organic solvent may be one or more of N, N-Dimethylformamide (DMF), dimethyl sulfoxide (DMSO), dioxane, dichloroethane, THF, ethyl acetate, and the like.
The alkaline catalyst comprises one or more of sodium hydroxide, sodium methoxide and sodium ethoxide.
Preferably, the dihaloalkane is one of dihalomethane, dihaloethane, dihalopropane and dihalobutane, and the halogenated element is chlorine, bromine and iodine.
Preferably, the tertiary amine is selected from trimethylamine, triethylamine, tripropylamine and tributylamine.
In a preferred embodiment of the present invention, 1 part (by mass) of polystyrene supported polyethylene glycol resin is soaked in 4 parts of N, N-Dimethylformamide (DMF) overnight, 5 parts of 25% sodium methoxide-methanol solution is added, distillation is performed to remove most of methanol and DMF, 4 parts of DMF is supplemented, 4 parts of 1, 4-dihalobutane is added, the reaction is performed for 5 to 8 hours under a reflux state, then, 1 part of ethanol, water and ethanol are sequentially used for leaching, and vacuum drying is performed at room temperature until the weight is constant.
Taking 1 part of the dried resin and 2 parts of tributylamine, and reacting for 12-24 hours in a reflux state by taking 5 parts of DMF as a solvent. And after the reaction is finished, performing suction filtration, washing with 1-2 parts of water and ethanol respectively, and drying for later use.
The quaternary ammonium salt catalyst can also adopt polystyrene immobilized polyethylene glycol resin-supported quaternary ammonium salt prepared by other known methods.
The polystyrene immobilized polyethylene glycol resin can be prepared from a commercially available product or a self-prepared product, for example, the following method is adopted for self-preparation:
(1) chloromethylation of polystyrene resin
1 part of polystyrene resin is taken and put into 3-5 parts (mass parts) of dichloroethane for swelling for 1-2 h at 25-30 ℃. Dropwise adding 5-8 parts of sulfuryl chloride into 3-5 parts of methylal within 1 hour at 25-30 ℃, reacting for 1-2 hours while keeping the temperature, pouring the reaction mixed solution into 8-12 parts of dichloromethane resin solution, and stirring for 3-5 hours. Slowly adding 1-2 parts of anhydrous zinc chloride powder at 40-55 ℃, and stirring for reacting for 8-12 h. After cooling, filtering out chloromethyl polystyrene resin, and washing with 5-10 parts of methylal for standby in three times.
(2) Chloromethylated resin immobilized polyethylene glycol
Adding 1 part of chloromethylated polystyrene resin prepared in the step (1) into 5-10 parts of dioxane, heating to 50-60 ℃, dissolving 8-10 parts of polyethylene glycol-400 in 3-5 parts of 33 wt% sodium hydroxide solution, adding the solution into resin solution, carrying out reflux reaction for 9-11h, washing the resin with 5-10 parts of distilled water for 3 times, leaching with ethanol and water, and carrying out vacuum drying at room temperature to constant weight.
The adding amount of the catalyst in the method is 1-10 wt%, preferably 3-8 wt%, and more preferably 5-8 wt% of the mass of the sodium taurate.
In the method for preparing the N-methyl sodium taurate, a solvent is added, the mass ratio of the added solvent to the sodium taurate is 2-10: 1, preferably 2-8: 1, more preferably 2-5: 1, and the solvent is preferably water.
In the method, the reaction temperature is 35-100 ℃, preferably 35-90 ℃, and more preferably 50-80 ℃;
in the method, the reaction time is 1-10 h, preferably 2-8 h, and more preferably 3-6 h;
in the method, the reaction pressure is 0.1-10.0 MpaG, preferably 0.5-8.0 MpaG, and more preferably 0.5-5.0 MpaG;
the parts used in the present invention all represent parts by mass.
The method has the advantages of high utilization rate of raw materials, thorough reaction, no complicated separation process of the current process, low energy consumption and easy operation; the reaction condition is mild, the reaction condition under the catalysis is easy to meet, the equipment requirement is low, the controllability is good, the separation is easy, the product purity is high, and the preparation method is green and environment-friendly.
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 of the invention is analyzed by liquid chromatography equipped with an ultraviolet detector, wherein the liquid chromatography is an Agilent 1200 series and is equipped with a C18 liquid chromatography column, the temperature of the column is set to be 40 ℃, 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.
The NMR was model Bruke 400.
The sodium taurate serving as a raw material in the invention is from national center for industrial crystallization engineering and technology research of Tianjin university.
Example 1
Preparation of catalyst a:
1) chloromethylation of polystyrene resin
26g of polystyrene resin was taken and placed in 100ml of dichloroethane to swell for 1 hour at room temperature. 114.1g of methylal is added dropwise to 202.5g of sulfuryl chloride within 1 hour at 25 ℃, the temperature is kept for 1 hour, the reaction mixture is poured into 200ml of dichloromethane resin solution, and the mixture is stirred for 3 hours. 30.3g of anhydrous zinc chloride powder is slowly added at the temperature of 40 ℃, and the reaction is stirred for 8 hours. After cooling, the chloromethyl polystyrene resin was filtered off and washed 3 times with 60ml of methylal each for further use.
2) Chloromethylated resin immobilized polyethylene glycol
Weighing 20.0g of chloromethylated polystyrene resin, adding 200g of dioxane, heating to 50 ℃, dissolving 175g of polyethylene glycol-400 in 75g of 33 wt% sodium hydroxide solution, adding the solution into the resin solution, carrying out reflux reaction for 10 hours, washing the resin with 100g of distilled water for 3 times, sequentially and respectively eluting with 25g of ethanol, 25g of water and 25g of ethanol, and carrying out vacuum drying at room temperature to constant weight. The grafting amount of the polyethylene glycol obtained by calculation is 0.49mmol/g according to the chlorine content before and after the reaction and the weight gain of the catalyst.
3) Loaded quaternary ammonium salts
Soaking 15g of the resin obtained in the step 2) in 60g of N, N-Dimethylformamide (DMF) overnight, adding 75g of a newly prepared 25% sodium methoxide-methanol solution, distilling for 1h to remove most of methanol and DMF, supplementing 60g of DMF, adding 150g of 1, 4-dichlorobutane, and reacting for 5h under reflux. Then, 30g of ethanol, 30g of water and 30g of ethanol are used for leaching in sequence, and vacuum drying is carried out at room temperature until the weight is constant.
The chlorine content was 2.95% by weight as determined by the oxygen bottle combustion method.
10g of the dried modified resin, 25g of tributylamine and 60g of DMF are taken as solvents and reacted for 12 hours under the reflux state. After the reaction is finished, the reaction solution is filtered,
and respectively leaching with 10g of ethanol, 10g of water and 10g of ethanol, and drying in vacuum at room temperature until the weight is constant. The average nitrogen content was 0.4148 wt% as determined by elemental analysis. The graft amount of the quaternary ammonium salt is 0.296mmol/g after conversion.
The halogen content was 0.395mmol/g as measured by eluting the resin with a silver nitrate solution.
The catalyst is labeled catalyst a.
Preparation of catalyst b:
1) loaded quaternary ammonium salts
Taking 15g of externally purchased polystyrene-supported polyethylene glycol resin (Xian Ruixi biological technology Co., Ltd.), wherein the grafting capacity of polyethylene glycol is 0.49mmol/g, soaking the resin in 60g of N, N-Dimethylformamide (DMF) overnight, adding 75g of newly prepared 25% sodium methoxide-methanol solution, distilling for 1h, removing most of methanol and DMF, supplementing 60g of DMF, then adding 150g of 1, 4-dichloropropane, and reacting for 6h under reflux. Then, 30g of ethanol, 30ml of water and 30g of ethanol are used for leaching in sequence, and vacuum drying is carried out at room temperature until the weight is constant.
The chlorine content was 3.02 wt% as determined by the oxygen bottle combustion method.
10g of the dried resin obtained in step (1), 24g of tripropylamine and 60g of DMF as a solvent were reacted under reflux for 12 hours. And after the reaction is finished, performing suction filtration, sequentially leaching with 10g of ethanol, 10g of water and 10g of ethanol, and performing vacuum drying at room temperature to constant weight.
The average nitrogen content was 0.5020 wt% as determined by elemental analysis. The grafting amount of the quaternary ammonium salt is 0.358mmol/g after conversion.
The halogen content was found to be 0.478mmol/g by eluting the resin with silver nitrate solution.
The catalyst is labeled catalyst b.
Preparation of catalyst c:
1) loaded quaternary ammonium salts
Taking 15g of externally purchased polystyrene immobilized polyethylene glycol resin (Xian Ruixi biological technology Co., Ltd.), wherein the grafting capacity of polyethylene glycol is 0.49mmol/g, soaking the resin in 75g of N, N-Dimethylformamide (DMF) overnight, adding 90g of newly prepared 25% sodium ethoxide-ethanol solution, distilling the solution for 1h, removing most of methanol and DMF, supplementing 75g of DMF, adding 120g of 1, 4-dichloroethane, and reacting the mixture for 7h under reflux. Then, the mixture is sequentially leached by 25g of ethanol, 25g of water and 25g of ethanol, and is dried in vacuum at room temperature until the weight is constant.
The chlorine content was 3.13% by weight as determined by the oxygen bottle combustion method.
2) 10g of the resin modified in the step (1) after drying, 21g of triethylamine and 50g of DMF as a solvent were reacted under reflux for 18 hours. And after the reaction is finished, performing suction filtration, sequentially leaching with 10g of ethanol, 10g of water and 10g of ethanol, and performing vacuum drying at room temperature to constant weight.
The average nitrogen content was 0.5020 wt% as determined by elemental analysis. The grafting amount of the quaternary ammonium salt is 0.334mmol/g after conversion.
The halogen content was found to be 0.446mmol/g by eluting the resin with a silver nitrate solution.
The catalyst is labeled catalyst c.
Preparation of catalyst d:
1) loaded quaternary ammonium salts
Taking 15g of externally purchased polystyrene-supported polyethylene glycol resin (Xian Ruixi biological technology Co., Ltd.), wherein the grafting capacity of polyethylene glycol is 0.49mmol/g, soaking the resin in 75g of N, N-Dimethylformamide (DMF) overnight, adding 84g of newly prepared 25% sodium methoxide-methanol solution, distilling for 1h, removing most of methanol and DMF, supplementing 75g of DMF, adding 150g of 1, 4-dichloromethane, and reacting for 8h under reflux. Then, 20g of ethanol, 20g of water and 20g of ethanol are used for leaching in sequence, and vacuum drying is carried out at room temperature until the weight is constant.
The chlorine content was 3.16 wt% as determined by the oxygen bottle combustion method.
2) 10g of the resin modified in the step (1) after drying, 28g of trimethylamine and 50g of DMF as a solvent were reacted under reflux for 24 hours. After the reaction is finished, the reaction solution is filtered,
and leaching the mixture by using 10g of ethanol, 10g of water and 10g of ethanol in sequence, and drying the mixture in vacuum at room temperature until the weight is constant.
The average nitrogen content was 0.4327 wt% as determined by elemental analysis. The graft amount of the quaternary ammonium salt is 0.309mmol/g after conversion.
The halogen content was 0.412mmol/g as determined by eluting the resin with a silver nitrate solution.
The catalyst is labeled catalyst d.
Example 2
147.0g of sodium taurate and 294.0g of deionized water are added into a 2L reactor, stirred until the sodium taurate is completely dissolved, and then 4.4g of catalyst a, N are added into the reactor2Replacing three times, heating to 66 ℃, and filling N into the system2Until the pressure is 1.2MpaG, 709.7g of methyl iodide is pumped into the system, and the temperature is kept for 4 hours for reaction. After the reaction, 135.4g of N-methyltaurine sodium is obtained by LC quantification. The reaction conversion was 87.25% with a selectivity of 96.38%.
1HNMR(400MHz,D2O)δ3.54(t,J＝7.1Hz,2H),3.27(s,3H),3.13(t,J＝7.1Hz,2H).
Example 3
146.9g of sodium taurate and 731.8g of deionized water are added into a reactor, stirred until the sodium taurate is completely dissolved, and then 8.8g of catalyst is added into the reactorb，N2Replacing for three times, heating to 70 ℃, and filling N into the system2Until the pressure is 3.5MpaG, 187.9g of methyl bromide is pumped into the system, and the temperature is kept for 5 hours for reaction. After the reaction, 147.2g of N-methyltaurate was quantitatively obtained by LC. The reaction conversion was 93.56% with selectivity 97.72%.
Example 4
587.8g of 25 wt% sodium taurate aqueous solution was added to the reactor, and 7.35g of catalyst c, N was added to the reactor2Replacing for three times, heating to 80 ℃, and filling N into the system2Until the pressure is 5.0MpaG, 149.97g of chloromethane is pumped into the system, and the temperature is kept for reaction for 3 hours. After the reaction, 151.6g of sodium methyltaurate was quantitatively obtained by LC. The conversion of the reaction was 97.13% and the selectivity was 96.92%.
Example 5
Adding 220.5g of 20 wt% sodium taurate aqueous solution into a reactor, adding 2.2g of catalyst c into the reactor, replacing three times with N2, heating to 50 ℃, filling N2 into the system until the pressure is 2.0MpaG, pumping 709.65g of methyl iodide into the system, and carrying out heat preservation reaction for 5 hours. After the reaction, 32.9g of N-methyltaurine sodium is obtained by LC quantification. The reaction conversion was 78.35% with a selectivity of 86.94%.
Example 6
Adding 600g of water into a reactor, adding 10.0g of catalyst d, replacing with N2 for three times, heating to 60 ℃, filling N2 into the system until the pressure is 1.0MpaG, adding 588.3g of 25 wt% sodium taurate aqueous solution into the reactor at the speed of 1.6g/min, pumping 50.0g of methane chloride into the system at the speed of 0.14g/min while adding the sodium taurate aqueous solution, starting to feed for 1h, then opening a discharge valve to ensure that the discharge speed of the reactor is 1.8g/min, and sampling and detecting after continuing to feed for 5 h. After the reaction, 135.7g of N-methyltaurate was quantitatively obtained by LC. The reaction conversion was 85.49% with a selectivity of 98.63%.
Comparative example 1
Adding 73.1g of N-methylacetamide into a reactor, adding 392.0g of 50% sulfuric acid into the reactor within 2 hours, heating, controlling the reaction temperature in the reactor to be about 100 ℃, reacting for 18 hours, then adding 67.4g of 50% ammonium bisulfite into the system, controlling the temperature at about 100 ℃ under normal pressure, reacting for 12 hours, cooling to the temperature T in the reactor being less than 50 ℃, then dropwise adding 100ml of 30% hydrogen peroxide into the reactor, reacting for 2 hours, concentrating and centrifuging the product to obtain 106.3g of solid, and detecting the mass of the N-methyltaurate to be 86.0g by LC. The reaction conversion was 68.50% with a selectivity of 90.2%.
Claims (9)
1. The method for preparing the sodium methyl taurate is characterized in that halogenated methane and sodium taurate are used as raw materials, and quaternary ammonium salt is used as a catalyst to prepare the N-sodium methyl taurate.
2. The method of claim 1, wherein the methyl halide is one or more of methyl iodide, methyl bromide or methyl chloride.
3. The process according to claim 1 or 2, wherein the molar ratio of the raw material sodium taurate to the halogenated methane is 0.05-2.0:1, preferably 0.05-1.0: 1, more preferably 0.2-1: 1.
4. The process of any of claims 1-3, wherein the quaternary ammonium salt catalyst is a polymer-supported quaternary ammonium salt catalyst;
preferably, the quaternary ammonium salt catalyst carrier is polystyrene immobilized polyethylene glycol resin.
5. The process according to any one of claims 1 to 4, the catalyst is prepared by:
soaking 1 part of polystyrene immobilized polyethylene glycol resin in 4-6 parts of organic solvent overnight, adding 1-2 parts of alkaline catalyst, distilling to remove most of the organic solvent, supplementing 4-5 parts of organic solvent, adding 5-10 parts of dihaloalkane, reacting for 5-8 h under a reflux state, washing and drying;
and adding 1 part of dried resin and 2-3 parts of tertiary amine into 4-6 parts of organic solvent, and reacting for 12-24 hours.
6. The method of claim 5, wherein the organic solvent comprises one or more of N, N-Dimethylformamide (DMF), dimethyl sulfoxide (DMSO), dioxane, dichloroethane, THF, ethyl acetate solvent;
preferably, the alkaline catalyst comprises one or more of sodium hydroxide, sodium methoxide and sodium ethoxide;
preferably, the dihalogenated alkane comprises one of dihalogenated methane, dihalogenated ethane, dihalogenated propane and dihalogenated butane, and the halogenated element is preferably one of chlorine, bromine and iodine;
preferably, the tertiary amine comprises trimethylamine, triethylamine, tripropylamine and tributylamine.
7. A process according to any one of claims 1 to 6, wherein the catalyst is added in an amount of 1 to 10 wt%, preferably 3 to 8 wt%, more preferably 5 to 8 wt% based on the mass of sodium taurate.
8. The method of any one of claims 1 to 7, wherein a solvent is further added in the reaction for preparing the sodium N-methyltaurate, the mass ratio of the added solvent to the sodium taurate is 2-10: 1, preferably 2-8: 1, more preferably 2-5: 1,
the solvent is preferably water.
9. The process according to any one of claims 1 to 8, wherein the reaction temperature for preparing sodium N-methyltaurate is 35 to 100 ℃, preferably 35 to 90 ℃, more preferably 50 to 80 ℃;
the reaction time is 1-10 h, preferably 2-8 h, and more preferably 3-6 h;
the reaction pressure is 0.1 to 10.0MpaG, preferably 0.5 to 8.0MpaG, and more preferably 0.5 to 5.0 MpaG.
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