CN110483473B - Method for preparing 1, 3-propane sultone - Google Patents
Method for preparing 1, 3-propane sultone Download PDFInfo
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- CN110483473B CN110483473B CN201910845331.8A CN201910845331A CN110483473B CN 110483473 B CN110483473 B CN 110483473B CN 201910845331 A CN201910845331 A CN 201910845331A CN 110483473 B CN110483473 B CN 110483473B
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- propane sultone
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- C07—ORGANIC CHEMISTRY
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- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/04—Five-membered rings
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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- Y02E60/10—Energy storage using batteries
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Abstract
The invention discloses a solvent-free method for preparing 1, 3-propane sultone, which takes allyl alcohol and ammonium sulfite as reaction raw materials, takes deionized water as a medium, firstly, ammonium sulfate and deionized water are stirred, the temperature is between 20 and 50 ℃, a mixed solution prepared by allyl alcohol, an initiator and deionized water is dripped into a beaker for catalytic reaction to generate a water solution of 3-hydroxypropanesulfonic acid ammonium, then, calcium hydroxide is added for alkalization reaction, concentrated sulfuric acid is added for acidification treatment after alkalization is finished to further obtain 3-hydroxypropanesulfonic acid and solid calcium sulfate, the water solution of 3-hydroxypropanesulfonic acid is obtained by filtration, a target product is obtained by concentration and reduced pressure rectification, a certain amount of calcium hydroxide and water are added into kettle residue, hydrolysis is carried out to obtain a water solution of 3-hydroxypropanesulfonic acid calcium, concentrated sulfuric acid is added for acidification treatment and filtration to obtain a water solution of 3-hydroxypropanesulfonic acid, and the target product is obtained by concentration and reduced pressure rectification; the method has the advantages of simple process, simple raw materials, no solvent, no waste generation and high yield up to 95%.
Description
Technical Field
The invention relates to the field of lithium ion battery electrolyte additives, in particular to a method for preparing 1, 3-propane sultone serving as a lithium ion battery electrolyte additive.
Background
The structural formula of the 1, 3-propane sultone is as follows:
1, 3-propane sultone is widely applied to the fields of dye, medicine, surfactant, lithium battery and the like; a process for preparing 1, 3-propane sultone includes such steps as reaction at 40-100 deg.C in the presence of hydrosulfite, sulfite and propenol, water as medium and crown ether as catalyst to obtain reaction mixture containing hydroxypropanesulfonic acid, acidifying the reaction mixture containing hydroxypropanesulfonic acid by adding hydrochloric acid, extracting with absolute alcohol, filtering to obtain the mixture containing hydroxypropanesulfonic acidAnd then rectifying the obtained reaction mixture containing the hydroxypropanesulfonic acid at high temperature to obtain the target product 1, 3-propane sultone.
The preparation method has the disadvantages that the reaction needs certain temperature and time, the solvent is flammable and explosive, the recovered ethanol contains acidity, and the equipment is easy to corrode; the method needs absolute ethyl alcohol, the recovered ethyl alcohol is difficult to dehydrate until no water exists, loss exists in the recovery process, the treatment is difficult in production, the cost is high, and the 3-hydroxypropanesulfonic acid is easy to polymerize among molecules at high temperature in distillation, so that the product yield is influenced.
Disclosure of Invention
The invention aims to provide a preparation method of 1,3 propane sultone, which does not need solvent, has low reaction temperature, simple and cheap raw materials, simple process, high product molar yield, less waste and easy obtainment of high-purity products.
The technical scheme adopted by the invention for solving the technical problem is as follows: s1, taking allyl alcohol and ammonium sulfite as reaction raw materials, taking deionized water as a medium, adding ammonium sulfite and deionized water into a three-neck flask, stirring, keeping the temperature between 20 and 50 ℃, preparing a mixed solution of allyl alcohol, an initiator and deionized water according to a certain proportion, and dropwise adding the mixed solution into the three-neck flask for catalytic reaction to generate 3-ammonium hydroxypropanesulfonate, wherein the initiator is tert-butyl hydroperoxide; s2, adding a certain amount of calcium hydroxide into the obtained aqueous solution containing the 3-hydroxypropanesulfonic acid ammonium to carry out alkalization reaction, adding a certain amount of concentrated sulfuric acid to carry out acidification treatment after alkalization is finished so as to obtain 3-hydroxypropanesulfonic acid and solid calcium sulfate, and finally filtering to obtain an aqueous solution of the 3-hydroxypropanesulfonic acid; s3, concentrating and rectifying the aqueous solution of the 3-hydroxypropanesulfonic acid under reduced pressure to obtain a target product 1, 3-propane sultone; and S4, adding a certain amount of calcium hydroxide and water into the kettle residue after the rectification in the step S3, hydrolyzing to obtain an aqueous solution of 3-calcium hydroxypropanesulfonate, adding concentrated sulfuric acid to perform acidification treatment and filtration to obtain an aqueous solution of 3-hydroxypropanesulfonic acid, and performing concentration and reduced pressure rectification to obtain the 1, 3-propane sultone.
The reaction equation of the invention is as follows:
as a further improvement of the scheme, the molar ratio of the allyl alcohol to the ammonium sulfite in the step S1 is 1 (1-2), the mass percent of the ammonium sulfite solution is 50-70%, and the molar ratio of the allyl alcohol, the initiator and the deionized water in the mixed solution of the allyl alcohol, the initiator and the deionized water is 1: (0.01-0.1): (2-3).
As a further improvement of the above scheme, the molar amount of calcium hydroxide in the step S2 is the molar amount of ammonium sulfite, and the molar amount of sulfuric acid added is the molar amount of calcium hydroxide.
As a further improvement of the above scheme, the weight of the calcium hydroxide in step S4 is 0.1 to 3 times of the weight of the still residue, and the weight ratio of the calcium hydroxide to the water is 1:1.5, the molar weight of the concentrated sulfuric acid is the same as that of the added calcium hydroxide.
As a further improvement of the above scheme, the catalytic reaction time in the step S1 is 2 to 5 hours.
As a further improvement of the scheme, the temperature in the acidification treatment processes in the step S2 and the step S4 is 60-70 ℃, and the acidification treatment time is 1-2 hours.
As a further improvement of the scheme, the temperature of collected fractions in the concentration and vacuum rectification in the step S3 and the step S4 is 110-140 ℃, and the vacuum degree is 20-70 Pa.
As a further improvement of the scheme, the hydrolysis temperature in the step S4 is 80-90 ℃, and the hydrolysis time is 3-4 hours.
As a further improvement of the scheme, the weight of the calcium hydroxide is 0.5 to 1 time of the weight of the kettle residue.
Compared with the prior art, the method for preparing the 1, 3-propane sultone provided by the invention utilizes the hydrolysis reaction of ammonium sulfite in water to generate ammonium bisulfite, the ammonium bisulfite reacts with propylene alcohol to produce the ammonium 3-hydroxypropanesulfonate, the ammonium 3-hydroxypropanesulfonate is converted into calcium 3-hydroxypropanesulfonate by the principle of preparing weak base by strong base, the calcium 3-hydroxypropanesulfonate is easy to dissolve in water, then equal molar concentrated sulfuric acid is added to ensure that calcium salt completely generates calcium sulfate precipitate to obtain a high-purity intermediate product 3-hydroxypropanesulfonic acid, and finally the target product 1, 3-propane sultone is obtained by reduced pressure rectification; the whole reaction system is carried out in a water phase;
the tert-butyl hydroperoxide is used as a reaction initiator, can be prepared into a stable mixed solution with deionized water and allyl alcohol, and is dripped into the ammonium sulfite aqueous solution, only one dripping head tank is needed, and the equipment investment is saved; the use of the initiator tert-butyl hydroperoxide greatly reduces the synthesis reaction temperature, shortens the reaction time and improves the conversion rate of the allyl alcohol. The method has the advantages that the ammonium sulfite is used as a reaction raw material, the method is stable compared with ammonium bisulfite, the transportation is convenient, the price is low, the production cost is reduced, solid calcium sulfate and high-purity 3-hydroxypropanesulfonic acid are obtained after the alkalization of calcium hydroxide and the acidification of sulfuric acid, a solvent is not needed in the process, the steps of solvent extraction, desolventizing concentration and solvent recovery treatment are saved, the step is simple and easy to operate, the safety risk is low, and the method is very suitable for large-scale industrial production.
Detailed Description
Example 1
Adding 580g (5 mol) of ammonium sulfite and 1000g of deionized water into a 3000L three-neck flask with a mechanical stirring device, a thermometer, a dripping device and a condenser pipe, stirring, dripping 290g (5 mol) of allyl alcohol, 40g of initiator tert-butyl hydroperoxide and 200g of deionized water at 45 ℃, keeping the temperature for 1 hour, and finishing the reaction when the content of the allyl alcohol is less than 1% by sampling; 375g (5 mol) of calcium hydroxide solid is added into the reaction liquid, stirred for 2 hours at the temperature of 40-50 ℃, and when no gas is generated in the reaction, 500g (5 mol) of concentrated sulfuric acid is slowly dripped, and the temperature is controlled between 60-70 ℃; stirring for 2 hours after the dropwise addition is finished, cooling, filtering to obtain a 3-hydroxypropanesulfonic acid aqueous solution and calcium sulfate solid, carrying out reduced pressure rectification on the 3-hydroxypropanesulfonic acid aqueous solution under the pressure of 30-40pa, and collecting fractions at 130-140 ℃, thereby obtaining 533g of high-purity 1, 3-propane sultone, wherein the content is 99.9%, and the residual amount in the kettle is 112g; adding 46g of solid calcium hydroxide and 100g of deionized water into the kettle residue, stirring and heating to 80 ℃ for hydrolysis reaction for 4 hours, cooling, adding 60g of concentrated sulfuric acid, controlling the temperature to be 60-70 ℃, stirring for 2 hours, cooling, filtering to obtain an aqueous solution of 3-hydroxypropanesulfonic acid, carrying out reduced pressure rectification under the pressure of 30-40pa, collecting fractions at the temperature of 130-140 ℃, obtaining 52g (the content is 99.9%) of 1, 3-propanesultone, and finally obtaining 585g of 1, 3-propanesultone in total, wherein the calculated molar yield is 95.79%.
Example 2
Adding 151g (1.3 mol) of ammonium sulfite and 220g of deionized water into a 3000L three-neck flask with a mechanical stirring device, a thermometer, a dropping device and a condensing tube, stirring, then dropping 58g (1 mol) of allyl alcohol, 8g of initiator tert-butyl hydroperoxide and 40g of deionized water at 45 ℃, wherein the dropping time is 1.5 hours, keeping the temperature for 2 hours, and finishing the reaction when the content of the allyl alcohol is less than 1% by sampling; adding 97g (1.3 mol) of calcium hydroxide solid into the reaction solution, stirring for 2 hours at the temperature of 40-50 ℃, and slowly dropwise adding 130g (1.3 mol) of concentrated sulfuric acid after no gas is generated in the reaction, wherein the temperature is controlled between 60-65 ℃; stirring for 1 hour after the dropwise addition is finished, cooling, and filtering to obtain a 3-hydroxypropanesulfonic acid aqueous solution and calcium sulfate solid, wherein the 3-hydroxypropanesulfonic acid aqueous solution is subjected to reduced pressure rectification under the pressure of 30-40pa, and fractions at 130-140 ℃ are collected, so that 103.5g of high-purity 1, 3-propane sultone is obtained, the content is 99.9%, and the kettle residue is 23g; adding 15g of solid calcium hydroxide and 20g of deionized water into the residue, stirring and heating to 85 ℃ for hydrolysis reaction for 3 hours, cooling, adding 20g of concentrated sulfuric acid, controlling the temperature to be 60-65 ℃, stirring for 1 hour, cooling, filtering to obtain an aqueous solution of 3-hydroxypropanesulfonic acid, carrying out reduced pressure rectification under the pressure of 30-40pa, collecting fractions at the temperature of 130-140 ℃, carrying out reduced pressure rectification under the pressure of 30-40pa to obtain 12.8g (the content is 99.9%) of 1, 3-propanesultone, and finally obtaining 116.3g of 1, 3-propanesultone in total, wherein the calculated molar yield is 95.21%.
Example 3
Adding 174g (1.5 mol) of ammonium sulfite and 250g of deionized water into a 3000L three-neck flask with a mechanical stirrer, a thermometer, a dropping device and a condenser tube, stirring, then simultaneously dropping 58g (1 mol) of allyl alcohol, 9g of initiator tert-butyl hydroperoxide and 50g of deionized water at 45 ℃, wherein the dropping time is 1 hour, keeping the temperature for 2 hours, and finishing the reaction when the content of the allyl alcohol is less than 1% by sampling; adding 112g (1.5 mol) of calcium hydroxide solid into the reaction solution, stirring for 2 hours at the temperature of 40-50 ℃, and slowly dropwise adding 150g (1.5 mol) of concentrated sulfuric acid after no gas is generated in the reaction, wherein the temperature is controlled between 50-60 ℃; stirring for 2 hours after the dropwise addition is finished, cooling, filtering to obtain a 3-hydroxypropanesulfonic acid aqueous solution and calcium sulfate solid, carrying out reduced pressure rectification on the 3-hydroxypropanesulfonic acid aqueous solution under the pressure of 30-40pa, and collecting fractions at 130-140 ℃, thereby obtaining 104.1g of high-purity 1, 3-propane sultone, the content of which is 99.9%, and the residual amount of the kettle is 24.2g; adding 15g of solid calcium hydroxide and 20g of deionized water into the residue, stirring and heating to 85 ℃ for hydrolysis reaction for 3 hours, cooling, adding 20g of concentrated sulfuric acid, controlling the temperature to be 60-65 ℃, stirring for 2 hours, cooling, filtering to obtain an aqueous solution of 3-hydroxypropanesulfonic acid, carrying out reduced pressure rectification under the pressure of 30-40pa, collecting fractions at the temperature of 130-140 ℃, obtaining 12.6g (the content is 99.9%) of 1, 3-propanesultone, and finally obtaining 116.7g of 1, 3-propanesultone in total, wherein the calculated molar yield is 95.54%.
The beneficial effects of the invention are as follows: the method for preparing the 1, 3-propane sultone takes tert-butyl hydroperoxide as a reaction initiator, can be prepared into a stable mixed solution with deionized water and allyl alcohol, and is dripped into an ammonium sulfite aqueous solution, only one dripping head tank is needed, and the equipment investment is saved; the use of the initiator tert-butyl hydroperoxide greatly reduces the synthesis reaction temperature, shortens the reaction time and improves the conversion rate of the allyl alcohol. The method has the advantages that the ammonium sulfite is used as a reaction raw material, the method is stable compared with ammonium bisulfite, the transportation is convenient, the price is low, the production cost is reduced, solid calcium sulfate and high-purity 3-hydroxypropanesulfonic acid are obtained after the calcium hydroxide alkalization and the sulfuric acid acidification, no solvent is needed in the process, the steps of solvent extraction, desolventizing concentration and solvent recovery treatment are saved, the steps are simple and easy to operate, the safety risk is low, the method is extremely suitable for large-scale industrial production, the process is simple, no waste is generated, and the yield can reach more than 95%.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.
Claims (9)
1. A process for preparing 1, 3-propane sultone comprising the steps of:
s1, taking allyl alcohol and ammonium sulfite as reaction raw materials, taking deionized water as a medium, adding ammonium sulfite and deionized water into a three-neck flask, stirring, keeping the temperature between 20 and 50 ℃, preparing a mixed solution of allyl alcohol, an initiator and deionized water according to a certain proportion, and dropwise adding the mixed solution into the three-neck flask for catalytic reaction to generate 3-ammonium hydroxypropanesulfonate, wherein the initiator is tert-butyl hydroperoxide;
s2, adding a certain amount of calcium hydroxide into the obtained aqueous solution containing the ammonium 3-hydroxypropanesulfonate for alkalization reaction, adding a certain amount of concentrated sulfuric acid after alkalization is finished for acidification treatment to obtain 3-hydroxypropanesulfonic acid and solid calcium sulfate, and finally filtering to obtain an aqueous solution of the 3-hydroxypropanesulfonic acid;
s3, concentrating and rectifying the aqueous solution of the 3-hydroxypropanesulfonic acid under reduced pressure to obtain a target product 1, 3-propane sultone;
and S4, adding a certain amount of calcium hydroxide and water into the kettle residue after the rectification in the step S3, hydrolyzing to obtain an aqueous solution of 3-calcium hydroxypropanesulfonate, adding concentrated sulfuric acid to perform acidification treatment and filtration to obtain an aqueous solution of 3-hydroxypropanesulfonic acid, and performing concentration and reduced pressure rectification to obtain the 1, 3-propane sultone.
2. The method for preparing 1, 3-propane sultone according to claim 1, wherein the molar ratio of allyl alcohol to ammonium sulfite in step S1 is 1 (1-2), the mass percent of the ammonium sulfite solution is 50% -70%, and the molar ratio of allyl alcohol, initiator and deionized water in the mixed solution of allyl alcohol, initiator and deionized water is 1: (0.01-0.1): (2-3).
3. The method for preparing 1, 3-propane sultone according to claim 1, characterized in that the molar amount of calcium hydroxide in step S2 is the molar amount of ammonium sulfite, and the molar amount of sulfuric acid added is the molar amount of calcium hydroxide.
4. The method for preparing 1, 3-propane sultone according to claim 1, wherein the weight of calcium hydroxide in step S4 is 0.1 to 3 times of the weight of still residue, and the weight ratio of calcium hydroxide to water is 1:1.5, the molar weight of the concentrated sulfuric acid is the same as that of the added calcium hydroxide.
5. The method for preparing 1, 3-propane sultone according to claim 1, wherein the catalytic reaction time in step S1 is 2 to 5 hours.
6. The method for preparing 1, 3-propane sultone according to claim 1, wherein the temperature during the acidification in step S2 and step S4 is 60-70 ℃ and the acidification time is 1-2 hours.
7. The method for preparing 1, 3-propane sultone according to claim 1, characterized in that the temperature of collected fraction in step S3 and step S4 is 110-140 deg.C and vacuum degree is 20-70 Pa.
8. The method for preparing 1, 3-propane sultone according to claim 1, wherein the hydrolysis temperature in step S4 is 80-90 ℃ and the hydrolysis time is 3-4 hours.
9. The method for producing 1, 3-propane sultone according to claim 4, wherein the weight of calcium hydroxide is 0.5 to 1 times the weight of still residue.
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| CN112174857A (en) * | 2020-10-26 | 2021-01-05 | 湖北吉和昌化工科技有限公司 | Preparation method of 3-hydroxypropanesulfonic acid |
| 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 |
| CN115611851B (en) * | 2022-11-03 | 2024-04-26 | 湖北吉和昌化工科技有限公司 | Preparation method of 1, 3-propane sultone |
| CN116396157A (en) * | 2023-04-07 | 2023-07-07 | 阜阳欣奕华制药科技有限公司 | Method for preparing 2-iodobenzoic acid in one pot |
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