CN116253668B - Preparation method of sodium hydroxyalkyl sulfonate - Google Patents
Preparation method of sodium hydroxyalkyl sulfonate Download PDFInfo
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- CN116253668B CN116253668B CN202310531518.7A CN202310531518A CN116253668B CN 116253668 B CN116253668 B CN 116253668B CN 202310531518 A CN202310531518 A CN 202310531518A CN 116253668 B CN116253668 B CN 116253668B
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- 229910052708 sodium Inorganic materials 0.000 title claims abstract description 26
- 239000011734 sodium Substances 0.000 title claims abstract description 26
- 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 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 125000002768 hydroxyalkyl group Chemical group 0.000 title claims abstract description 21
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 25
- 230000003068 static effect Effects 0.000 claims abstract description 22
- 239000000047 product Substances 0.000 claims abstract description 18
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 16
- 229920005862 polyol Polymers 0.000 claims abstract description 13
- 150000003077 polyols Chemical class 0.000 claims abstract description 13
- 239000006227 byproduct Substances 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 230000035484 reaction time Effects 0.000 claims abstract description 6
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 claims abstract description 3
- 229910000342 sodium bisulfate Inorganic materials 0.000 claims abstract description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 35
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 35
- 239000004289 sodium hydrogen sulphite Substances 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 21
- 239000004005 microsphere Substances 0.000 claims description 17
- 229920001467 poly(styrenesulfonates) Polymers 0.000 claims description 14
- 239000000945 filler Substances 0.000 claims description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 11
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 238000006277 sulfonation reaction Methods 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 238000000746 purification Methods 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 4
- 238000010924 continuous production Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 229940045998 sodium isethionate Drugs 0.000 description 30
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 10
- 239000000376 reactant Substances 0.000 description 8
- YNJORDSKPXMABC-UHFFFAOYSA-M sodium;2-hydroxypropane-2-sulfonate Chemical compound [Na+].CC(C)(O)S([O-])(=O)=O YNJORDSKPXMABC-UHFFFAOYSA-M 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000007259 addition reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 hydroxyalkyl sulfonate Chemical compound 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000005496 eutectics Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- KDKIWFRRJZZYRP-UHFFFAOYSA-N 1-hydroxypropane-2-sulfonic acid Chemical class OCC(C)S(O)(=O)=O KDKIWFRRJZZYRP-UHFFFAOYSA-N 0.000 description 1
- HSXUNHYXJWDLDK-UHFFFAOYSA-N 2-hydroxypropane-1-sulfonic acid Chemical class CC(O)CS(O)(=O)=O HSXUNHYXJWDLDK-UHFFFAOYSA-N 0.000 description 1
- WUTXMERGVVXFNJ-UHFFFAOYSA-N CC(F)S(O)(=O)=O.Cl Chemical compound CC(F)S(O)(=O)=O.Cl WUTXMERGVVXFNJ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Images
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
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F33/00—Other mixers; Mixing plants; Combinations of mixers
- B01F33/80—Mixing plants; Combinations of mixers
- B01F33/836—Mixing plants; Combinations of mixers combining mixing with other treatments
- B01F33/8362—Mixing plants; Combinations of mixers combining mixing with other treatments with chemical reactions
-
- 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
- Y02P20/10—Process efficiency
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of chemical product synthesis, and discloses a preparation method of sodium hydroxyalkyl sulfonate. The preparation method comprises the following steps: the alkylene oxide and sodium bisulfate solution are heated by a heat exchanger respectively and then mixed by a static mixer, and then introduced into a pipeline reactor for reaction, so as to obtain the sodium hydroxyalkyl sulfonate solution with the byproduct polyol content less than or equal to 0.1 percent. The method adopts the static mixer to mix and the pipeline reactor to carry out continuous reaction, and has the advantages of stable quality, high production efficiency (reaction time is 1.0-30.0 min), high yield (more than 99%), high safety, low labor intensity of workers, less equipment investment, contribution to realizing industrialized continuous production and the like. Meanwhile, the unexpected discovery that the reaction conditions can improve the reaction selectivity and can obviously reduce the content of the byproduct polyol to below 0.1% without adopting a further purification process.
Description
Technical Field
The invention belongs to the technical field of chemical product synthesis, and particularly relates to a preparation method of sodium hydroxyalkyl sulfonate.
Background
Sodium hydroxyalkyl sulfonate is mainly used as a surfactant intermediate, a daily chemical intermediate, a pharmaceutical intermediate, and the like. The product is a main raw material for producing sodium cocoyl hydroxyalkyl sulfonate, and is widely used in industries such as electroplating, detergents and the like. Can be used as detergent for wool spinning products, intermediates for daily chemical products (such as shampoo, high-grade soap, etc.), intermediates for medicinal raw materials and fine chemical products.
The current preparation of sodium hydroxyalkyl sulfonate is mainly prepared by the addition reaction of sodium bisulphite and alkylene oxide, and the widely adopted production process is as follows:
preparing sodium bisulphite into 30-40 wt% aqueous solution, replacing nitrogen, heating, adding alkylene oxide at 60-90 ℃, and then starting to react, wherein the temperature is kept at 80-100 ℃ and the pressure is kept at 0-0.3 mpa. And after adding quantitative alkylene oxide, keeping the temperature at 80-100 ℃ for 30-120 minutes to obtain a crude product of sodium hydroxyalkyl sulfonate with the mass concentration of 40-45%. However, in the product prepared by the method, the content of the impurity polyol is 1.5% -2.0%, and the residue of the impurity polyol can negatively influence the quality of the product for further synthesizing the sodium hydroxyalkyl sulfonate derivative, so that a further process or other means are needed to reduce the content of the polyol in the sodium hydroxyalkyl sulfonate product.
Patent CN 111320558A discloses a taurine synthesis method, which adopts sodium bisulphite aqueous solution and ethylene oxide to react, and can obtain liquid of sodium isethionate. The temperature and pressure of this reaction were respectively: the reaction time is 10-120 min at 20-100 ℃ and 0.5-5 bar. The target product contains byproducts (ethylene glycol), so that the nanofiltration membrane is further utilized to filter the target product, and the byproducts (ethylene glycol) can be finally removed through filtration. Patent CN 102050769A discloses that sodium isethionate with ethylene glycol content below 0.1wt% and purity above 99.5wt% is obtained by double-effect evaporation recrystallization purification process.
Patent CN 1906288B to a stainless steel autoclave reactor was charged with 9.40 lbs of 35% aqueous sodium bisulfite solution at pH 6.5-7.0, then purged with nitrogen. The batch was heated to about 70℃and 1.01bs of propylene oxide was added to the reaction vessel at 60 psi. The reactants were allowed to react at a temperature of about 80 ℃ for about 30 minutes, then the pressure in the reaction vessel was reduced to about 1psi. The reaction was kept at 80℃for 60 minutes and finally cooled to 50℃and the product was taken out of the reaction vessel and analyzed. The results of the analysis showed that the product solution had a pH of 13.50 and propylene glycol <0.50wt% and both isomers of 2-methyl-2-hydroxyethane 1-sulfonate and 1-methyl-2-hydroxyethane 1-sulfonate.
Patent CN 109485586 A discloses that the specific molecular sieve catalysts (H-Beta (12.5) molecular sieve, dealuminated De-Al-Beta (12.5) molecular sieve and tin modified Sn-Beta (12.5) molecular sieve) are adopted to greatly reduce the technological conditions of the addition reaction of sodium bisulphite and ethylene oxide, so that the yield of an intermediate product sodium isethionate can be improved to more than 99 percent, and the generation of ethylene glycol in the process is reduced. Patent CN 113801041A by introducing a new eutectic solvent (choline chloride-fluoroethane sulfonic acid eutectic solvent) which has better solubility for both raw materials sodium bisulphite and ethylene oxide, but no solubility for the product; the solvent can not dissolve the sodium isethionate, so the sodium isethionate is continuously precipitated in a solid form along with the progress of the reaction, and the reuse of the reaction mother solution is not affected. The method solves the problem of accumulation of ethylene glycol impurity in the traditional ethylene oxide method, and can directly obtain solid sodium isethionate with extremely high purity. Patent CN 113372247A by employing SO 2 And NaOH to replace NaHSO 3 And obtaining sodium isethionate with high concentration (55% -60%) of a crude product, and obtaining high-purity sodium isethionate solid through evaporative crystallization, so as to reduce energy consumption and improve yield in the evaporative crystallization purification step.
It can be seen from experience of those skilled in the art in actual production and the above prior art that it is difficult to obtain sodium hydroxyalkylsulfonate product having a by-product polyol content of less than 0.1wt% by directly performing addition reaction of sodium bisulfite and alkylene oxide.
Disclosure of Invention
In view of the above drawbacks and shortcomings of the prior art, an object of the present invention is to provide a method for preparing sodium hydroxyalkylsulfonate. The method adopts the static mixer to mix and the pipeline reactor to carry out continuous reaction, and has the advantages of stable quality, high production efficiency (reaction time is 1.0-30.0 min), high yield (more than 99%), high safety, low labor intensity of workers, less equipment investment, contribution to realizing industrialized continuous production and the like. Meanwhile, the reaction condition of the invention can improve the reaction selectivity, and the content of the byproduct polyol can be obviously reduced to below 0.1 percent without adopting a further purification process.
The invention aims at realizing the following technical scheme:
a preparation method of sodium hydroxyalkyl sulfonate, which has the following structural formula:
wherein R is 1 、R 2 Are respectively and independently selected from C1-C6 alkyl or H;
the preparation method comprises the following steps:
heating alkylene oxide and sodium bisulfate solution respectively through a heat exchanger, mixing through a static mixer, and then introducing into a pipeline reactor for reaction to obtain sodium hydroxyalkyl sulfonate solution with the byproduct polyol content less than or equal to 0.1%;
the reaction temperature in the pipeline reactor is 40-100 ℃, the reaction time is 1.0-30.0 min, and the reaction pressure is 0.3-0.8 MPa.
Further, the alkylene oxide is preferably ethylene oxide or propylene oxide.
Further, the molar ratio of the alkylene oxide to the sodium bisulfite is preferably 0.95-1.02:1.00.
Further, the sodium bisulphite solution is preferably an aqueous sodium bisulphite solution with the mass percentage content of 30.0% -40.0%.
Further, the heat exchanger is preferably a tube heat exchanger or a plate heat exchanger.
Further, the static mixer is preferably a tubular static mixer with a fixed filler of sulfonated polystyrene microspheres therein.
Further, the sulfonated polystyrene microsphere is prepared by a sulfonation reaction of concentrated sulfuric acid with polystyrene microsphere with the particle size of 5-200 mu m.
Further, the yield of the product sodium hydroxyalkyl sulfonate reacted in the pipeline reactor is more than 99 percent.
Compared with the prior art, the invention has the beneficial effects that:
(1) The invention adopts a static mixer to fully mix the alkylene oxide and the sodium bisulphite solution, and adopts a pipeline reactor to carry out continuous reaction, and has the advantages of stable quality, high production efficiency (reaction time is 1.0-30.0 min), high yield (more than 99%), high safety, low labor intensity of workers, less equipment investment, contribution to realizing industrialized continuous production and the like.
(2) The reaction condition of the invention can improve the reaction selectivity, can obviously reduce the content of byproduct polyol to below 0.1 percent under the condition of no need of adopting a further purification process, and solves the technical problem that the content of byproduct polyol is difficult to reduce in the addition reaction of sodium bisulphite and alkylene oxide under the conventional condition.
Drawings
Fig. 1 is a schematic diagram of a preparation process flow of sodium isethionate in example 1 of the present invention.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but embodiments of the present invention are not limited thereto.
The sulfonated polystyrene microsphere fixed fillers used in the following examples were prepared by the following method:
and adding polystyrene microspheres with average particle size of 65 mu m into concentrated sulfuric acid, carrying out sulfonation reaction for 4 hours at 40-45 ℃, washing and drying reaction products, and thus obtaining the sulfonated polystyrene microspheres.
Example 1
The preparation method of the sodium isethionate in the embodiment has a preparation process flow diagram shown in fig. 1, and the structural formula of the sodium isethionate is as follows:
the preparation method of the sodium isethionate comprises the following steps:
0.97mol of ethylene oxide and a sodium bisulphite aqueous solution containing 1.00mol of sodium bisulphite with the mass percentage content of 36% are respectively mixed by a metering pump through a tubular static mixer with a sulfonated polystyrene microsphere fixed filler after being heated to 40 ℃ by a tubular heat exchanger, and then are introduced into a pipeline reactor. The process parameters in the pipeline reactor are as follows: the reaction temperature was 40℃and the residence time of the reactants in the pipe reactor was 30.0min, the reaction pressure was 0.3MPa. A sodium isethionate solution was obtained.
The yield of sodium isethionate in this example was 99.1% and the ethylene glycol residue was 0.09% as calculated by detection.
Example 2
The structural formula of the sodium isethionate is as follows:
the preparation method of the sodium isethionate comprises the following steps:
the 0.95mol of ethylene oxide and the sodium bisulphite aqueous solution containing 1.00mol of sodium bisulphite with the mass percentage content of 30% are respectively heated to 50 ℃ by a metering pump through a tubular heat exchanger, then mixed by a tubular static mixer with a sulfonated polystyrene microsphere fixed filler inside, and then introduced into a pipeline reactor. The process parameters in the pipeline reactor are as follows: the reaction temperature was 50℃and the residence time of the reactants in the pipe reactor was 20.0min, the reaction pressure was 0.4MPa. A sodium isethionate solution was obtained.
The sodium isethionate yield of this example was 99.3% and ethylene glycol residue was 0.08% as calculated by detection.
Example 3
The structural formula of the sodium isethionate is as follows:
the preparation method of the sodium isethionate comprises the following steps:
0.99mol of ethylene oxide and sodium bisulphite aqueous solution containing 1.00mol of sodium bisulphite with the mass percentage content of 40% are respectively heated to 70 ℃ by a metering pump, then are mixed by a tubular static mixer with sulfonated polystyrene microsphere fixed filler inside, and then are introduced into a pipeline reactor. The process parameters in the pipeline reactor are as follows: the reaction temperature was 70℃and the residence time of the reactants in the pipe reactor was 15.0min, the reaction pressure was 0.6MPa. A sodium isethionate solution was obtained.
The yield of sodium isethionate in this example was 99.5% and the ethylene glycol residue was 0.09% as calculated by detection.
Example 4
The structural formula of the sodium isethionate is as follows:
the preparation method of the sodium isethionate comprises the following steps:
1.02mol of ethylene oxide and 35 percent sodium bisulfite aqueous solution containing 1.00mol of sodium bisulfite are respectively heated to 100 ℃ by a tube type heat exchanger through a metering pump, mixed by a tube type static mixer with sulfonated polystyrene microsphere fixed filler inside, and then introduced into a pipeline reactor. The process parameters in the pipeline reactor are as follows: the reaction temperature was 100deg.C, the residence time of the reactants in the pipe reactor was 1.0min, and the reaction pressure was 0.8MPa. A sodium isethionate solution was obtained.
The yield of sodium isethionate in this example was 99.8% and the ethylene glycol residue was 0.09% as calculated by detection.
Example 5
The structural formula of the sodium hydroxyisopropyl sulfonate is as follows:
the preparation method of the sodium hydroxyisopropyl sulfonate comprises the following steps:
1.01mol of propylene oxide and a sodium bisulphite aqueous solution containing 1.00mol of sodium bisulphite with the mass percentage content of 35% are respectively heated to 80 ℃ by a metering pump, mixed by a tubular static mixer with a sulfonated polystyrene microsphere fixed filler inside, and then introduced into a pipeline reactor. The process parameters in the pipeline reactor are as follows: the reaction temperature was 80℃and the residence time of the reactants in the pipe reactor was 5.0min, the reaction pressure was 0.7MPa. Obtaining sodium hydroxyisopropyl sulfonate solution.
The yield of sodium hydroxyisopropyl sulfonate in this example was 99.7% and the propylene glycol residue was 0.08%.
Comparative example 1
Compared with the example 1, the comparative example adopts the conventional reaction kettle mixing reaction to replace the static mixer mixing and pipeline reactor reaction, and the other process parameters are the same, and the specific preparation steps are as follows:
adding sodium bisulfite aqueous solution containing 1.00mol sodium bisulfite with the mass percent of 36 percent into a reaction kettle, then introducing 0.97mol ethylene oxide, heating to 40 ℃ and regulating the reaction pressure to 0.3MPa, and reacting for 30.0min to obtain sodium isethionate solution.
The yield of the sodium isethionate of the comparative example was 95.1% and the ethylene glycol residue was 0.52%.
Comparative example 2
Compared with the example 1, the tubular static mixer has no sulfonated polystyrene microsphere fixed filler, and the other process parameters are the same, and the specific preparation steps are as follows:
0.97mol of ethylene oxide and 36 mass percent aqueous sodium bisulfite solution containing 1.00mol of sodium bisulfite are respectively heated to 40 ℃ by a tube type heat exchanger through a metering pump, mixed by a tube type static mixer without fixed filler, and then introduced into a pipeline reactor. The process parameters in the pipeline reactor are as follows: the reaction temperature was 40℃and the residence time of the reactants in the pipe reactor was 30.0min, the reaction pressure was 0.3MPa. A sodium isethionate solution was obtained.
The yield of the sodium isethionate of the comparative example was 98.6% and the ethylene glycol residue was 0.58%.
Comparative example 3
Compared with the example 5, the conventional reaction kettle mixing reaction is adopted to replace the static mixer mixing and pipeline reactor reaction, the other process parameters are the same, and the specific preparation steps are as follows:
adding sodium bisulfite aqueous solution containing 1.00mol sodium bisulfite with the mass percent of 35 percent into a reaction kettle, then introducing 1.01mol propylene oxide, heating to 80 ℃ and regulating the reaction pressure to 0.7MPa, and reacting for 5.0min to obtain sodium hydroxyisopropyl sulfonate solution.
The yield of the sodium hydroxyisopropyl sulfonate of the comparative example was 98.7% and the propylene glycol residue was 1.10%.
Comparative example 4
Compared with the example 5, the tubular static mixer has no sulfonated polystyrene microsphere fixed filler, and the other process parameters are the same, and the specific preparation steps are as follows:
1.01mol of propylene oxide and a sodium bisulphite aqueous solution containing 1.00mol of sodium bisulphite with the mass percentage content of 35% are respectively heated to 80 ℃ by a plate heat exchanger through a metering pump, are mixed by a tubular static mixer without fixed filler, and then are introduced into a pipeline reactor. The process parameters in the pipeline reactor are as follows: the reaction temperature was 80℃and the residence time of the reactants in the pipe reactor was 5.0min, the reaction pressure was 0.7MPa. Obtaining sodium hydroxyisopropyl sulfonate solution.
The yield of the sodium hydroxyisopropyl sulfonate of the comparative example was 99.2% and the propylene glycol residue was 1.07%.
As can be seen from the comparison results of the above examples and comparative examples, the synthesis reaction of the invention adopts the static mixer of the sulfonated polystyrene microsphere fixed filler to fully mix the alkylene oxide and the sodium bisulphite solution, and adopts the pipeline reactor to perform continuous reaction instead of the conventional reaction kettle reaction, thereby not only improving the reaction efficiency and the yield, but also having the effect of improving the reaction selectivity, obviously promoting the addition reaction of the alkylene oxide and the sodium bisulphite, reducing the ring-opening of the alkylene oxide to generate the polyol, obviously reducing the content of the byproduct polyol to below 0.1 percent without adopting a further purification process, and obviously improving the production efficiency and the product quality.
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 (7)
1. The preparation method of the sodium hydroxyalkyl sulfonate is characterized in that the structural formula of the sodium hydroxyalkyl sulfonate is as follows:
wherein R is 1 、R 2 Are respectively and independently selected from C1-C6 alkyl or H;
the preparation method comprises the following steps:
heating alkylene oxide and sodium bisulfate solution respectively through a heat exchanger, mixing through a static mixer, and then introducing into a pipeline reactor for reaction to obtain sodium hydroxyalkyl sulfonate solution with the byproduct polyol content less than or equal to 0.1%;
the static mixer is a tubular static mixer with sulfonated polystyrene microsphere fixed filler inside;
the reaction temperature in the pipeline reactor is 40-100 ℃, the reaction time is 1.0-30.0 min, and the reaction pressure is 0.3-0.8 MPa.
2. The method for producing sodium hydroxyalkylsulfonate as claimed in claim 1, wherein the alkylene oxide is ethylene oxide or propylene oxide.
3. The method for preparing sodium hydroxyalkyl sulfonate according to claim 1, wherein the molar ratio of alkylene oxide to sodium bisulfite is 0.95-1.02:1.00.
4. The method for preparing sodium hydroxyalkyl sulfonate according to claim 1, wherein the sodium bisulphite solution is 30.0% -40.0% sodium bisulphite aqueous solution by mass percent.
5. The method for preparing sodium hydroxyalkyl sulfonate according to claim 1, wherein the heat exchanger is a tube type heat exchanger or a plate type heat exchanger.
6. The method for preparing sodium hydroxyalkyl sulfonate according to claim 1, wherein the sulfonated polystyrene microsphere is prepared by sulfonation reaction of concentrated sulfuric acid with polystyrene microsphere with particle size of 5-200 μm.
7. The method for preparing sodium hydroxyalkyl sulfonate according to claim 1, wherein the yield of the product sodium hydroxyalkyl sulfonate reacted in the pipeline reactor is more than 99%.
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