CN112174857A - Preparation method of 3-hydroxypropanesulfonic acid - Google Patents
Preparation method of 3-hydroxypropanesulfonic acid Download PDFInfo
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- CN112174857A CN112174857A CN202011156100.5A CN202011156100A CN112174857A CN 112174857 A CN112174857 A CN 112174857A CN 202011156100 A CN202011156100 A CN 202011156100A CN 112174857 A CN112174857 A CN 112174857A
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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
- C07C303/02—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
- C07C303/20—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 addition of sulfurous acid or salts thereof to compounds having carbon-to-carbon multiple bonds
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
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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
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
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Abstract
The invention relates to a preparation method of 3-hydroxypropanesulfonic acid. The method comprises the following steps: 1) introducing propylene alcohol and sodium bisulfite water solution into a microchannel reactor to react under the initiation of an initiator to prepare 3-sodium hydroxypropanesulfonate; 2) introducing the 3-hydroxypropanesulfonic acid sodium prepared in the step 1) into an ion exchange system for ion exchange to prepare 3-hydroxypropanesulfonic acid. The invention ensures the full reaction and reduces the dosage of acid.
Description
Technical Field
The invention relates to the field of preparation of organic compounds, in particular to a preparation method of 3-hydroxypropanesulfonic acid.
Background
The 3-hydroxy propane sulfonic acid is an important organic synthesis intermediate, is an important sulfonating agent, generates 1, 3-propane sultone after dehydration and cyclization, can be widely used for synthesizing electroplating intermediates, surfactants, sensitizing dyes and power battery electrolyte additives, and is used for improving the energy storage effect and safety and stability of power batteries.
CAS number 15909-83-8
Molecular formula C3H8O4S
Molecular weight 140.16
At present, the industrial production method of 3-hydroxypropanesulfonic acid mainly uses propylene alcohol and sodium metabisulfite or sodium bisulfite as raw materials, under the initiation of an initiator, the 3-hydroxypropanesulfonic acid sodium is prepared through an intermittent kettle type reaction, the reaction is insufficient, in addition, the 3-hydroxypropanesulfonic acid sodium needs to be acidified through inorganic acid which is excessive by more than one time, a large amount of waste acid water is generated, and the problems of energy consumption waste and environmental pollution are caused. The prior art proposes a hydrogen chloride gas acidification process, which can reduce the amount of waste acid, but has potential safety hazard and inconvenient transportation and operation in industrial production.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: the amount of acid used is reduced while ensuring sufficient reaction.
In order to solve the technical problem, the invention provides a preparation method of 3-hydroxypropanesulfonic acid.
A preparation method of 3-hydroxypropanesulfonic acid comprises the following steps:
1) introducing propylene alcohol and sodium bisulfite water solution into a microchannel reactor to react under the initiation of an initiator to prepare 3-sodium hydroxypropanesulfonate;
2) introducing the 3-hydroxypropanesulfonic acid sodium prepared in the step 1) into an ion exchange system for ion exchange to prepare 3-hydroxypropanesulfonic acid.
Further, in the step 1), the allyl alcohol, the initiator and water are mixed to obtain a mixed solution, and the mixed solution and the sodium bisulfite aqueous solution are pumped into a microchannel reactor from two inlets to react to prepare the 3-hydroxy propane sodium sulfonate.
Further, in the step 1), the mixed liquor and the sodium bisulfite aqueous solution are pumped into the microchannel reactor from two inlets simultaneously; wherein the pumping speed of the mixed solution is 130-135kg/h, and the pumping speed of the sodium bisulfite aqueous solution is 80-85 kg/h.
Further, in step 1), the mixed solution and the sodium bisulfite aqueous solution are simultaneously pumped into the microchannel reactor from two inlets and reacted under the pressure of 0.5-1 MPa.
Further, in the step 1), the temperature for introducing the propylene alcohol and the sodium bisulfite aqueous solution into the microchannel reactor to react under the initiation of the initiator is 20-60 ℃. The temperature condition is favorable for the reaction.
Further, in the step 1), the molar ratio of the allyl alcohol, the sodium bisulfite and the initiator is 1 (1-1.02) to 0.001-0.5. Little excess sodium bisulfite need be added.
Further, in step 1), the initiator is H2O2、NaS2O8、(CH3)3COOH and dibenzoyl peroxide.
Further, after the step 2), the method also comprises the steps of regenerating the ion exchange resin after ion exchange, and performing two-stage membrane electrodialysis treatment on waste acid water generated in the regeneration treatment to ionize the waste acid water into acid and alkali.
Further, after the step 2), the method also comprises the step of concentrating and separating the 3-hydroxypropanesulfonic acid prepared in the step 2) by an acid-resistant membrane.
Further, in step 2), the ion exchange system comprises a combination of at least two ion exchange resin columns.
Further, in step 2), the ion exchange resin in the ion exchange resin column is an acidic cation exchange resin.
Compared with the prior art, the invention has the advantages that: introducing propylene alcohol and sodium bisulfite water solution into a microchannel reactor to react under the initiation of an initiator to prepare 3-sodium hydroxypropanesulfonate; the method has the advantages that the reaction can be fully carried out in the microchannel reactor, the use amount of the sodium bisulfite raw material is not required to be additionally increased, so that the product discharged from the microchannel reactor does not contain residual sodium bisulfite, the sodium bisulfite is prevented from consuming acid in the subsequent ion exchange reaction, the ion exchange system is used for carrying out ion exchange to convert the 3-hydroxypropanesulfonic acid which hardly contains sodium bisulfite into the 3-hydroxypropanesulfonic acid, the acid use amount is reduced by more than half compared with the traditional batch reaction, and the use amount of the acid is reduced while the full reaction is ensured.
Drawings
The features and advantages of the present invention will be more clearly understood by reference to the accompanying drawings, which are illustrative and not to be construed as limiting the invention in any way, and in which:
FIG. 1 is a process flow diagram of an embodiment of the present invention.
Detailed Description
With reference to fig. 1, the present embodiment proposes a method for preparing 3-hydroxypropanesulfonic acid, including the following steps:
1) mixing the allyl alcohol, the initiator and water to obtain a mixed solution, simultaneously pumping the mixed solution and the sodium bisulfite aqueous solution into a microchannel reactor from two inlets, and reacting at the pressure of 0.5-1MPa and the reaction temperature of 20-60 ℃ to obtain the 3-hydroxy propane sodium sulfonate; wherein the pumping speed of the mixed solution is 130-135kg/h, and the pumping speed of the sodium bisulfite aqueous solution is 80-85 kg/h; the mol ratio of the allyl alcohol to the sodium bisulfite to the initiator is 1 (1-1.02) to 0.001-0.5; the initiator is H2O2、NaS2O8、(CH3)3COOH and dibenzoyl peroxide. The reaction is carried out under the pressure of 0.5-1MPa, the movement speed among molecules can be accelerated, the reaction progress is accelerated, and further, the pressure is adjusted by adjusting a discharge back pressure valve of the microchannel reactor.
2) Introducing the 3-hydroxypropanesulfonic acid sodium prepared in the step 1) into an ion exchange system for ion exchange to prepare 3-hydroxypropanesulfonic acid; the ion exchange system comprises a combination of at least two ion exchange resin columns, wherein the ion exchange resin in the ion exchange resin columns is an acidic cation exchange resin, preferably a strong-acid cation exchange resin, and the regenerated acid is preferably hydrochloric acid.
3) Performing regeneration treatment on the ion exchange resin after ion exchange, and performing two-stage membrane electrodialysis treatment on the waste acid water generated by the regeneration treatment to ionize the waste acid water into acid and alkali; the prepared 3-hydroxypropanesulfonic acid is concentrated and separated by an acid-resistant membrane.
The preparation method can recycle the wastewater generated in the production process after treatment, thereby greatly reducing the environmental pollution.
The preparation method of 3-hydroxypropanesulfonic acid proposed in the present embodiment with reference to fig. 1 is implemented by the following equipment: the device comprises a microchannel reactor, an ion exchange system, an acid-resistant membrane and a bipolar membrane electrodialysis device; the microchannel reactor is connected with an ion exchange system, and the ion exchange system is respectively connected with the acid-resistant membrane and the bipolar membrane electrodialysis device; the ion exchange system at least comprises an ion exchange column A and an ion exchange column B, wherein the ion exchange columns A and B alternately perform ion exchange and regeneration, namely, when the column A performs ion exchange, the column B performs resin regeneration and activation, and when the column B performs ion exchange, the column A performs resin regeneration and activation, so that the continuous operation of the system is ensured.
The working process of the equipment is as follows: introducing 3-hydroxypropanesulfonic acid sodium generated by the microchannel reactor into an ion exchange system for ion exchange to obtain 3-hydroxypropanesulfonic acid, concentrating and separating the 3-hydroxypropanesulfonic acid through an acid-resistant membrane, performing regeneration treatment on ion exchange resin after the ion exchange, performing two-stage membrane electrodialysis treatment on waste acid water generated by the regeneration treatment, ionizing to obtain dilute acid and dilute alkali, wherein the dilute acid is used for resin regeneration, and the dilute alkali is used for acid water neutralization. Further, the microchannel reactor comprises a two-channel metering pump and is provided with an online pH meter.
The following detailed description of the preferred embodiments of the present invention is provided in connection with the accompanying drawings, which form a part hereof, and which together with the embodiments of the invention serve to explain the principles of the invention and not to limit the scope thereof. It should be noted that the related devices adopted in the present invention are all devices in the prior art.
Example 1
The embodiment provides a preparation method of 3-hydroxypropanesulfonic acid, which comprises the following steps:
(1) adding 3000kg of deionized water and 1550kg of sodium bisulfite into a 5000L enamel reaction kettle A with mechanical stirring, and stirring and dissolving at room temperature;
(2) 2000kg of deionized water, 850kg of propylene alcohol and 20kg of H were added to a 3000L enamel reactor B with mechanical stirring2O2Stirring evenly at room temperature;
(3) pumping 130kg/h of liquid in the A kettle and 80kg/h of solution in the B kettle into a micro-channel reactor for reaction by a metering pump, wherein the reaction temperature is 50 ℃, and adjusting a discharging back pressure valve to enable the system pressure to reach 0.5 MPa;
(4) the reaction solution passes through an A column activated by an ion exchange system, the A column is switched to a B column after the resin of the A column is saturated by adsorbing sodium ions, the A column is regenerated at the moment, the A column is switched to the A column after the resin of the B column is saturated by adsorbing sodium ions, the B column is regenerated at the moment, the whole system is provided with a treatment process according to the flow and time, and the continuous operation can be realized after the production is started;
(5) the diluted acid after resin exchange enters an acid-proof membrane system, and is separated and concentrated; the yield of 3-hydroxypropanesulfonic acid was 99.2%;
(6) waste acid water generated after the resin regeneration enters a two-stage membrane electrodialysis system to be ionized into dilute acid and dilute alkali, wherein the dilute acid is circularly used for resin regeneration, and the dilute alkali is used for waste acid water neutralization.
Example 2
The embodiment provides a preparation method of 3-hydroxypropanesulfonic acid, which comprises the following steps:
(1) adding 3000kg of deionized water and 1560kg of sodium bisulfite into a 5000L enamel reaction kettle A with mechanical stirring, and stirring and dissolving at room temperature;
(2) 2000kg of deionized water was added to a 3000L enamel reactor B with mechanical stirringWater, 860kg of propylene alcohol and 25kg of NaS2O8Stirring evenly at room temperature;
(3) pumping 135kg/h of liquid in the A kettle and 82kg/h of solution in the B kettle into a micro-channel reactor for reaction by a metering pump, wherein the reaction temperature is 20 ℃, and adjusting a discharging back pressure valve to enable the system pressure to reach 1 MPa;
(4) the reaction solution passes through an A column activated by an ion exchange system, the A column is switched to a B column after the resin of the A column is saturated by adsorbing sodium ions, the A column is regenerated at the moment, the A column is switched to the A column after the resin of the B column is saturated by adsorbing sodium ions, the B column is regenerated at the moment, the whole system is provided with a treatment process according to the flow and time, and the continuous operation can be realized after the production is started; the concentration of hydrochloric acid in ion exchange is 5-10%, and the molar consumption of the hydrochloric acid is 1.2 times of that of allyl alcohol;
(5) the diluted acid after resin exchange enters an acid-proof membrane system, and is separated and concentrated; the yield of 3-hydroxypropanesulfonic acid was 99.3%;
(6) waste acid water generated after the resin regeneration enters a two-stage membrane electrodialysis system to be ionized into dilute acid and dilute alkali, wherein the dilute acid is circularly used for resin regeneration, and the dilute alkali is used for waste acid water neutralization.
Example 3
The embodiment provides a preparation method of 3-hydroxypropanesulfonic acid, which comprises the following steps:
(1) adding 3000kg of deionized water and 1570kg of sodium bisulfite into a 5000L enamel reaction kettle A with mechanical stirring, and stirring at room temperature for dissolving;
(2) to a 3000L enamel reactor B with mechanical agitation was added 2000kg deionized water, 860kg propylene alcohol and 25kg (CH)3)3COOH, and stirring uniformly at room temperature;
(3) pumping 132kg/h of liquid in the A kettle and 85kg/h of solution in the B kettle into a micro-channel reactor for reaction by a metering pump, wherein the reaction temperature is 60 ℃, and adjusting a discharging back pressure valve to enable the system pressure to reach 1 MPa;
(4) the reaction solution passes through an A column activated by an ion exchange system, the A column is switched to a B column after the resin of the A column is saturated by adsorbing sodium ions, the A column is regenerated at the moment, the A column is switched to the A column after the resin of the B column is saturated by adsorbing sodium ions, the B column is regenerated at the moment, the whole system is provided with a treatment process according to the flow and time, and the continuous operation can be realized after the production is started; the concentration of hydrochloric acid in ion exchange is 5-10%, and the molar consumption of the hydrochloric acid is 1.2 times of that of allyl alcohol;
(5) the diluted acid after resin exchange enters an acid-proof membrane system, and is separated and concentrated; the yield of 3-hydroxypropanesulfonic acid was 99.8%;
(6) waste acid water generated after the resin regeneration is added into a two-stage membrane electrodialysis system to be ionized into dilute acid and dilute alkali, wherein the dilute acid is circularly used for resin regeneration, and the dilute alkali is used for waste acid water neutralization.
Comparative example 1
The comparative example uses a conventional batch reaction to prepare 3-hydroxypropanesulfonic acid, and comprises the following specific steps:
adding 3000kg of deionized water and 1550kg of sodium bisulfite into a 5000L enamel reaction kettle A with mechanical stirring, and stirring and dissolving at room temperature;
(2) 2000kg of deionized water, 850kg of propylene alcohol and 20kg of H were added to a 3000L enamel reactor B with mechanical stirring2O2Stirring evenly at room temperature;
(3) dropwise adding the solutions in the step (1) and the step (2) into a 10000L enamel reaction kettle C at the same time, keeping the temperature at 50 ℃ for reaction for 3h after the dropwise adding is finished, and carrying out reduced pressure evaporation and concentration on the reaction liquid until white solids are separated out;
(4) firstly, hydrochloric acid with the concentration of 36% and the molar amount of 2.5 times of allyl alcohol is added, then 1500L of ethanol is added, the mixture is fully stirred and crystallized, the temperature is reduced to 5-10 ℃, then the salt is removed by suction filtration, and the mother liquor is concentrated and dehydrated in vacuum to obtain the 3-hydroxypropanesulfonic acid, wherein the yield of the 3-hydroxypropanesulfonic acid is 50.4%.
The yield of 3-hydroxypropanesulfonic acid obtained in comparative example 1 was much lower than that of 3-hydroxypropanesulfonic acid obtained in inventive example 1, and the amount of acid used for producing 3-hydroxypropanesulfonic acid by the process of the present invention was reduced by more than half.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are included in the scope of the present invention.
Claims (10)
1. A preparation method of 3-hydroxypropanesulfonic acid is characterized by comprising the following steps:
1) introducing propylene alcohol and sodium bisulfite water solution into a microchannel reactor to react under the initiation of an initiator to prepare 3-sodium hydroxypropanesulfonate;
2) introducing the 3-hydroxypropanesulfonic acid sodium prepared in the step 1) into an ion exchange system for ion exchange to prepare 3-hydroxypropanesulfonic acid.
2. The preparation method of claim 1, wherein in the step 1), the allyl alcohol, the initiator and water are mixed to obtain a mixed solution, and the mixed solution and the sodium bisulfite aqueous solution are pumped into a microchannel reactor from two inlets to react to prepare the sodium 3-hydroxypropanesulfonate.
3. The method according to claim 2, wherein in step 1), the mixed solution and the aqueous sodium bisulfite solution are pumped into the microchannel reactor from two inlets simultaneously; wherein the pumping speed of the mixed solution is 130-135kg/h, and the pumping speed of the sodium bisulfite aqueous solution is 80-85 kg/h.
4. The method according to claim 3, wherein in step 1), the mixed solution and the aqueous sodium bisulfite solution are simultaneously pumped into the microchannel reactor from two inlets and reacted at a pressure of 0.5 to 1 MPa.
5. The preparation method according to claim 1, wherein in the step 1), the temperature for introducing the propylene alcohol and the aqueous solution of sodium bisulfite into the microchannel reactor to react under the initiation of the initiator is 20-60 ℃.
6. The preparation method of claim 1, wherein in the step 1), the molar ratio of the allyl alcohol, the sodium bisulfite and the initiator is 1 (1-1.02) to (0.001-0.5).
7. The method according to claim 1, wherein in step 1), the initiator is H2O2、NaS2O8、(CH3)3COOH and dibenzoyl peroxide.
8. The preparation method according to claim 1, wherein after the step 2), the method further comprises the steps of performing regeneration treatment on the ion exchange resin after ion exchange, and performing double-stage membrane electrodialysis treatment on waste acid water generated in the regeneration treatment to ionize the waste acid water into acid and alkali.
9. The method of claim 1, wherein after the step 2), the method further comprises concentrating and separating the 3-hydroxypropanesulfonic acid obtained in the step 2) by an acid-resistant membrane.
10. The production method according to claim 1, wherein in step 2), the ion exchange system comprises a combination of at least two ion exchange resin columns; further, the ion exchange resin in the ion exchange resin column is an acidic cation exchange resin.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114315656A (en) * | 2021-12-07 | 2022-04-12 | 常熟聚和化学有限公司 | Decomposition and recovery treatment method of propane sultone oligomer |
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| CN110483473A (en) * | 2019-09-08 | 2019-11-22 | 淮安瀚康新材料有限公司 | A kind of solvent-free method for preparing 1,3- propane sultone |
| CN111100040A (en) * | 2019-12-23 | 2020-05-05 | 沈阳化工研究院有限公司 | Micro-channel continuous heterogeneous sulfonation reaction device and method |
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| CN109956923A (en) * | 2019-04-16 | 2019-07-02 | 张家港瀚康化工有限公司 | The method that micro passage reaction prepares 1,4- butane sultone |
| CN110483473A (en) * | 2019-09-08 | 2019-11-22 | 淮安瀚康新材料有限公司 | A kind of solvent-free method for preparing 1,3- propane sultone |
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Cited By (2)
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| CN114315656A (en) * | 2021-12-07 | 2022-04-12 | 常熟聚和化学有限公司 | Decomposition and recovery treatment method of propane sultone oligomer |
| CN114315656B (en) * | 2021-12-07 | 2023-05-23 | 常熟聚和化学有限公司 | Decomposition and recovery treatment method of propane sultone oligomer |
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