CN110746326A - Method for continuously producing hydroxyethyl sulfonic acid - Google Patents
Method for continuously producing hydroxyethyl sulfonic acid Download PDFInfo
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- CN110746326A CN110746326A CN201911034345.8A CN201911034345A CN110746326A CN 110746326 A CN110746326 A CN 110746326A CN 201911034345 A CN201911034345 A CN 201911034345A CN 110746326 A CN110746326 A CN 110746326A
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- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/16—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by oxidation of thiols, sulfides, hydropolysulfides, or polysulfides with formation of sulfo or halosulfonyl groups
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Abstract
The invention discloses a method for continuously producing isethionic acid, which belongs to the technical field of organic synthesis process, wherein β -mercaptoethanol is used as a substrate, hydrogen peroxide is used as an oxidant, and liquid-phase oxidation is continuously carried out in 60-180 s in a continuous flow microreactor with a special microstructure to produce isethionic acid, and materials are introduced into a microchannel reactor through a metering pump and then are preheated, mixed, reacted and separated to obtain isethionic acid products.
Description
Technical Field
The invention belongs to the technical field of organic synthesis processes, and particularly relates to a process for preparing a high-purity organic compound from β -mercaptoethanol serving as a raw material by H2O2A method for preparing isethionic acid by oxidation, in particular to a method for continuously producing isethionic acid by liquid phase oxidation by using β -mercaptoethanol as a raw material in a microchannel reactor.
Background
The hydroxyethyl sulfonic acid, also known as 2-hydroxyethanesulfonic acid, is an important organic intermediate due to the strong reactivity of hydroxyl and sulfonic acid groups and active chemical properties, and is widely applied to the fields of medicines, cosmetics, daily chemical products, electroplating and the like. In cosmetics and daily chemical products, a series of anionic surfactants are widely used in soaps, shampoo products and bath products because of their high water solubility and foaming properties.
In the aspect of medicine, the method is mainly used for producing sodium isethionate, taurine, pentamidine hydroxyethanesulfonate and the like. The hydroxyethyl sodium sulfonate is mainly used for synthesizing novel bactericides, such as hexamidine dihydroxyethyl sulfonate, which is used as a dandruff-removing and itching-relieving agent, and has obvious effect and small side effect in shampoos and shampoos. Taurine is an amino acid with special physiological function in vivo, can be used as food nutrition additive, and can be synthesized into various medicines. Pentamidine hydroxyethanesulfonate was used as early as 2004 for the treatment of aids pulmonary complications, and Dorlo et al, 2008, addressed the problem of dosing pentamidine hydroxyethanesulfonate and also indicated its role in the treatment of infectious pneumonia. As the application of the hydroxyethyl sulfonic acid is more and more extensive, the synthesis method thereof attracts people's extensive attention.
The methods commonly used in the industry at present for producing isethionic acid are mainly the EO method and H2O2An oxidation method. The EO method is to add sodium sulfite to ethylene oxide to obtain sodium isethionate and then to desalt the sodium isethionate.
CN105132440A discloses a method for preparing isethionic acid, which is characterized in that ethylene oxide gas is introduced into a synthesis tower filled with sodium bisulfite, and the reaction is carried out for 1h under the condition of 60-75 ℃, so that the yield of the obtained isethionic acid sodium is 95 percent, the acidification process of the process has high requirement on the concentration of hydrochloric acid, and the generated salt is difficult to remove, thereby affecting the purity of the product.
U.S. Pat. No. 005912385A proposes using H2O2β -mercaptoethanol is oxidized to obtain hydroxyethyl sulfonic acid, mercaptoethanol is slowly dripped, condensed water is introduced in the reaction process, the reaction is vigorously stirred at room temperature for 10 hours, then the reaction is continued for 5 hours by raising the temperature to 110 ℃, and a 54 percent mass fraction of hydroxyethyl sulfonic acid solution is obtained.
Weidongxi reported H2O2The method for obtaining the hydroxyethyl sulfonic acid by oxidation comprises the steps of firstly adding part of H into a flask2O2After preheating, slowly dripping two raw materials simultaneously, introducing cooling water during reaction, keeping the temperature below 50 ℃, continuously boiling condensed water after dripping, stirring and reacting for 2.5 hours, and generating a byproduct H due to deep oxidation2SO4。
The preparation process of the isethionic acid disclosed in the above patent or reported in the literature has reactors which are all reaction bottles or stirred reaction kettles with stirring, and the reaction modes are all intermittent operation. In the preparation process of the isethionic acid, ethylene oxide is gas at normal temperature, the addition reaction is a gas-liquid reaction system, gas-liquid mass transfer is difficult to realize in the reaction process, and a high-temperature and high-pressure reaction system is often required to promote the mass transfer in the reaction system. H2O2The process for preparing hydroxyethyl sulfonic acid by oxidizing β -mercaptoethanol is an exothermic reaction, the heat release is about 457.8kJ/mol, hydrogen peroxide is easy to decompose under the condition of heating, oxygen is released, a large amount of heat is released, and reactants and a solvent are evaporated in a large amountThe stable temperature control effect is poor, and the risk of temperature runaway is high; the system is open, the dead angle of the device is large, the process control is in an intermittent fluctuation state, and the stability and safety are determined to be low; the mass transfer efficiency is poor, the reaction efficiency is low, the serious decomposition of hydrogen peroxide is determined, the active oxygen overflow amount is large, the active oxygen utilization rate is low, the material consumption is high, and the material steam explosion risk is high.
The microchannel reactor is a special-shaped pipeline type reactor with an enhanced mass and heat transfer process, has ideal performance of an advection flow reactor through the special design of a microchannel structure, can be used for carrying out continuous synthesis of the isethionic acid, has miniaturized pipeline size, extremely large specific surface area and higher mass and heat transfer characteristics, can skip direct amplification through a step-by-step amplification test, and is flexible in production and high in safety performance.
Disclosure of Invention
Aiming at the defects of the process, the invention provides a method for continuously producing the isethionic acid, and the microchannel reactor has the structural characteristics of narrow reaction space and large specific surface area, so that mass transfer and heat transfer can be enhanced, the reaction temperature and the reaction time can be accurately controlled, the temperature runaway phenomenon and the generation of byproducts are prevented, and the conversion rate and the yield are improved. Meanwhile, the microchannel reactor has the characteristics of small liquid holdup, short reaction retention time, strong mass transfer and heat transfer effects, no dead volume and the like, and avoids the raw material H2O2The oxygen generated by decomposition is accumulated in the reactor, so that the safety of β -mercaptoethanol oxidation reaction is improved.
In order to achieve the purpose, the invention adopts the technical scheme that:
a method for continuously producing hydroxyethyl sulfonic acid by using a microchannel reactor comprises the following steps:
(1) the method comprises the steps of taking β -mercaptoethanol as a substrate and hydrogen peroxide as an oxidant, carrying out liquid-phase oxidation in a continuous-flow microreactor with a special microstructure to produce the isethionic acid, taking β -mercaptoethanol and hydrogen peroxide at room temperature as reaction materials, respectively, and respectively introducing the reaction materials into preheating modules in a microstructure reactor through metering pumps to preheat, wherein the preheating temperature is controlled by an external heat exchanger.
(2) The flow of the materials is controlled by the metering pump, so that the materials enter the coil pipe from different inlets simultaneously and enter the coil pipe after preheating for mixed reaction, after the reaction process is completed, the product flows out from the outlet of the coil pipe, the reaction material liquid is collected, and the reaction material liquid enters the post-treatment process.
(3) The reaction solution was extracted with a small amount of chloroform to remove acetaldehyde and acetic acid which may be formed during the reaction, and the aqueous phase was retained. Heating and stirring the reaction solution at 110 ℃, distilling under reduced pressure to remove water generated in the reaction solution, and obtaining the hydroxyethyl sulfonic acid solution after the reaction is finished.
The synthesis method comprises the following steps of (1) and (2) carrying out synthesis on isethionic acid, wherein the concentration of the hydrogen peroxide solution in the step (1) is 40-60% by mass, the molar ratio of hydrogen peroxide to β -mercaptoethanol is (3.2-3.8): 1, the reaction temperature is 30-50 ℃, the residence time is 60-180 s, and the reaction pressure is 5-15 bar, the conversion rate of β -mercaptoethanol is 78.6-94.8%, the mass fraction of the isethionic acid solution is 70-75.6%, the yield of isethionic acid is 73.46-87.3%, and the sulfuric acid content is 0.1-0.54%.
The continuous reaction system comprises different functional areas such as a preheating area, a reaction area, a quenching area and the like.
In the process of β -mercaptoethanol liquid-phase oxidation in a continuous flow microreactor in a continuous reaction mode, raw materials are pumped into a microchannel reaction system by a metering pump, the reaction temperature is controlled by a water bath kettle, the molar ratio among the materials is changed by adjusting the flow of the metering pump in the reaction process, the pressure in the reaction system is monitored and measured in real time by a pressure gauge, the raw materials are respectively preheated in the microchannel reactor, then mixed and reacted, and reaction products are obtained at a discharge port after certain residence time (from a few seconds to a few minutes).
Compared with the prior art, the invention has the following main characteristics:
1. the invention adopts a continuous production method, shortens the reaction time from traditional hours to dozens of seconds to several minutes, has short production period and more stable reaction process, and obviously improves the reaction efficiency.
2. The selected microchannel reactor can enhance the mass transfer and heat transfer performance, keep the reaction temperature constant, avoid the temperature runaway phenomenon, reduce the generation of by-products and improve the safety of the reaction process.
3. The selected microchannel reactor has strong mass transfer effect, so that liquid-liquid reaction liquid is fully mixed, excessive oxidation is effectively avoided, and the selectivity of the isethionic acid is improved.
Drawings
FIG. 1 is a process flow diagram for the continuous oxidation of β -mercaptoethanol to isethionic acid according to the present invention.
FIG. 2 is a diagram of a continuous flow microchannel reactor apparatus used in the present invention: 1. 2-raw material, 3, 4-raw material pump, 5, 6-preheating zone, 7-micro channel, 8-quenching zone and 9-product collection.
Detailed Description
The invention is further illustrated by the following examples, which are not intended to limit the scope of the invention.
The following examples were carried out in a microchannel reactor according to the requirements of the process of the present invention.
Example 1
The method comprises the steps of adjusting a microchannel reaction device to be a preheating zone, a reaction zone and a quenching zone according to the requirement of a reaction process, controlling the reaction residence time to be 60s by adjusting the flow rate of a pump and the channel length of a microchannel, setting the preheating temperature and the reaction temperature to be 30 ℃ and the reaction pressure to be 5bar, inputting a substrate β -mercaptoethanol into the preheating zone A of the device through a metering pump 1, inputting hydrogen peroxide with the concentration of 40% into the preheating zone B of the device through a pump 2, fully preheating two materials respectively, and then entering the two materials into the reaction zone for mixing reaction, wherein the molar ratio of the hydrogen peroxide to β -mercaptoethanol is 3.2:1, continuously discharging isethionic acid from an outlet, collecting the isethionic acid into a product collector, extracting and distilling the reaction liquid under reduced pressure to obtain a product, analyzing the product by HPLC, the conversion rate of β -mercaptoethanol is 78.6%, and analyzing the concentrations of isethionic acid and sulfuric acid by an acid-base neutralization titration method to obtain a 70% w/w isethionic acid aqueous solution (the yield is 73..
Example 2
According to the requirement of a reaction process, a microchannel reaction device is adjusted to be a preheating zone, a reaction zone and a quenching zone, the reaction residence time is controlled to be 70s by adjusting the flow rate of a pump and the channel length of a microchannel, the preheating temperature and the reaction temperature are set to be 35 ℃, the reaction pressure is 10bar, a substrate β -mercaptoethanol is input into the preheating zone A of the device through a metering pump 1, hydrogen peroxide with the concentration of 35% is input into the preheating zone B of the device through a pump 2, two materials are respectively and fully preheated and then enter the reaction zone for mixed reaction, wherein the molar ratio of the hydrogen peroxide to the β -mercaptoethanol is 3.3:1, the hydroxyethylsulfonic acid is continuously discharged from an outlet and collected into a product collector, the reaction liquid is extracted and subjected to reduced pressure distillation to obtain a product, the product is subjected to HPLC analysis, the conversion rate of the raw material β -mercaptoethanol is 85.5%, and the concentrations of the hydroxyethylsulfonic acid and the sulfuric acid are analyzed through an acid neutralization titration method and a precipitation method, so that an aqueous solution of the hydroxyethylsulfonic acid with the concentration of 73.7.
Example 3
According to the requirement of a reaction process, a microchannel reaction device is adjusted to be a preheating zone, a reaction zone and a quenching zone, the reaction residence time is controlled to be 80s by adjusting the flow rate of a pump and the channel length of a microchannel, the preheating temperature and the reaction temperature are set to be 40 ℃, the reaction pressure is 10bar, a substrate β -mercaptoethanol is input into the preheating zone A of the device through a metering pump 1, hydrogen peroxide with the concentration of 40% is input into the preheating zone B of the device through a pump 2, two materials are respectively and fully preheated and then enter the reaction zone for mixed reaction, wherein, the molar ratio of the hydrogen peroxide to the β -mercaptoethanol is 3.4:1, the hydroxyethylsulfonic acid is continuously discharged from an outlet and collected into a product collector, the reaction liquid is extracted and subjected to reduced pressure distillation to obtain a product, the product is subjected to HPLC analysis, the conversion rate of the raw material β -mercaptoethanol is 89.2%, and the concentrations of the hydroxyethylsulfonic acid and the sulfuric acid are analyzed through an acid-base neutralization titration method and a precipitation method, so as to obtain a 72.6% w/w hydroxyethylsulfonic acid.
Example 4
According to the requirement of a reaction process, a microchannel reaction device is adjusted to be a preheating zone, a reaction zone and a quenching zone, the reaction residence time is controlled to be 90s by adjusting the flow rate of a pump and the channel length of a microchannel, the preheating temperature and the reaction temperature are set to be 40 ℃, the reaction pressure is 15bar, a substrate β -mercaptoethanol is input into the preheating zone A of the device through a metering pump 1, hydrogen peroxide with the concentration of 45% is input into the preheating zone B of the device through a pump 2, two materials are respectively and fully preheated and then enter the reaction zone for mixed reaction, wherein, the molar ratio of the hydrogen peroxide to the β -mercaptoethanol is 3.5:1, the hydroxyethylsulfonic acid is continuously discharged from an outlet and collected into a product collector, the reaction liquid is extracted and subjected to reduced pressure distillation to obtain a product, the product is subjected to HPLC analysis, the conversion rate of the raw material β -mercaptoethanol is 91.2%, and the concentrations of the hydroxyethylsulfonic acid and the sulfuric acid are analyzed through an acid-base neutralization titration method and a precipitation method, so that a 74.8% w/w hydroxyethylsulfonic acid aqueous solution.
Example 5
According to the requirement of a reaction process, a microchannel reaction device is adjusted to be a preheating zone, a reaction zone and a quenching zone, the reaction residence time is controlled to be 90s by adjusting the flow rate of a pump and the channel length of a microchannel, the preheating temperature and the reaction temperature are set to be 50 ℃, the reaction pressure is 15bar, a substrate β -mercaptoethanol is input into the preheating zone A of the device through a metering pump 1, hydrogen peroxide with the concentration of 50% is input into the preheating zone B of the device through a pump 2, two materials are respectively and fully preheated and then enter the reaction zone for mixed reaction, wherein, the molar ratio of the hydrogen peroxide to the β -mercaptoethanol is 3.4:1, the hydroxyethylsulfonic acid is continuously discharged from an outlet and collected into a product collector, the reaction liquid is extracted and subjected to reduced pressure distillation to obtain a product, the product is subjected to HPLC analysis, the conversion rate of the raw material β -mercaptoethanol is 92.5%, and the concentrations of the hydroxyethylsulfonic acid and the sulfuric acid are analyzed through an acid-base neutralization titration method and a precipitation method, so that an aqueous solution of the hydroxyethylsulfonic acid with the concentration.
Example 6
The method comprises the steps of adjusting a microchannel reaction device to be a preheating zone, a reaction zone and a quenching zone according to the requirement of a reaction process, controlling the reaction residence time to be 120s by adjusting the flow rate of a pump and the channel length of a microchannel, setting the preheating temperature and the reaction temperature to be 50 ℃, and the reaction pressure to be 15bar, inputting a substrate β -mercaptoethanol into the preheating zone A of the device through a metering pump 1, inputting hydrogen peroxide with the concentration of 50% into the preheating zone B of the device through a pump 2, fully preheating two materials respectively, and then entering the two materials into the reaction zone for mixing reaction, wherein the molar ratio of the hydrogen peroxide to β -mercaptoethanol is 3.8:1, continuously discharging isethionic acid from an outlet, collecting the mixture into a product collector, extracting and distilling the reaction liquid under reduced pressure to obtain a product, analyzing the product by HPLC, the conversion rate of β -mercaptoethanol is 93.82%, and analyzing the concentrations of isethionic acid and sulfuric acid by an acid-base neutralization titration method and a precipitation method to obtain an aqueous solution of isethionic acid with the concentration of 73.8% w/w.
Example 7
The method comprises the steps of adjusting a microchannel reaction device to be a preheating zone, a reaction zone and a quenching zone according to the requirement of a reaction process, controlling the reaction residence time to be 180s by adjusting the flow rate of a pump and the channel length of a microchannel, setting the preheating temperature and the reaction temperature to be 50 ℃ and the reaction pressure to be 15bar, inputting a substrate β -mercaptoethanol into the preheating zone A of the device through a metering pump 1, inputting 60% hydrogen peroxide into the preheating zone B of the device through a pump 2, fully preheating two materials respectively, and then entering the two materials into the reaction zone for mixing reaction, wherein the molar ratio of the hydrogen peroxide to β -mercaptoethanol is 3.8:1, continuously discharging isethionic acid from an outlet and collecting the mixture into a product collector, extracting and distilling the reaction solution under reduced pressure to obtain a product, analyzing the product by HPLC (high performance liquid chromatography), converting the raw material β -mercaptoethanol to be 94.8%, and analyzing the concentrations of isethionic acid and sulfuric acid by an acid-base neutralization titration method and a precipitation method to obtain 75.6% w/w isethionic acid aqueous solution (the yield.
The above description is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any changes and substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are also intended to be covered by the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (4)
1. A method for continuously producing hydroxyethyl sulfonic acid by using a microchannel reactor is characterized by comprising the following steps:
(1) using β -mercaptoethanol as a substrate and hydrogen peroxide as an oxidant, and carrying out liquid-phase oxidation in a continuous flow microreactor with a special microstructure to produce the hydroxyethyl sulfonic acid, wherein β -mercaptoethanol and hydrogen peroxide at room temperature are respectively used as reaction materials and are respectively introduced into a preheating module in a microstructure reactor through a metering pump to be preheated, and the preheating temperature is controlled by an external heat exchanger;
(2) controlling the flow of the materials by a metering pump, enabling the preheated materials to synchronously enter reactor modules with different microchannel structures for mixing reaction, after the reaction process is finished, enabling a product to flow out of an outlet of the reactor, entering a closed pressure container to collect reaction liquid, and entering a post-treatment process;
(3) firstly, extracting reaction liquid by using a small amount of chloroform, removing acetaldehyde and acetic acid which are possibly generated in the reaction, and keeping a water phase; heating and stirring the reaction solution at 110 ℃, distilling under reduced pressure to remove water generated in the reaction solution, and obtaining the hydroxyethyl sulfonic acid solution after the reaction is finished.
2. The method of claim 1, wherein all reactions are continuous processes, and the microchannel reaction system comprises different functional zones such as a preheating zone, a reaction zone, and a quenching zone.
3. The method of claim 1, wherein the microchannel module structure comprises a straight-flow channel, a flat pipeline with a rectangular cross section, a pancake pulse variable diameter rectangular flat pipeline, an inclined pancake pulse variable diameter rectangular flat pipeline, an enhanced mixed pancake rectangular flat pipeline, and an enhanced mixed inclined pancake rectangular flat pipeline.
4. The method for continuously producing the isethionic acid according to claim 1, wherein the concentration of the aqueous hydrogen peroxide solution is 40-60% by mass, the molar ratio of hydrogen peroxide to β -mercaptoethanol is (3.2-3.8): 1, the reaction temperature is 30-50 ℃, the residence time is 60-180 s, and the reaction pressure is 5-15 bar.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112828494A (en) * | 2021-01-06 | 2021-05-25 | 研迈电子材料(上海)有限公司 | Novel brazing flux production method |
| CN115521231A (en) * | 2022-09-23 | 2022-12-27 | 天宝动物营养科技股份有限公司 | Environment-friendly clean preparation method of taurine |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112828494A (en) * | 2021-01-06 | 2021-05-25 | 研迈电子材料(上海)有限公司 | Novel brazing flux production method |
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