CN115872973A - 5363 purification method of 1,3-propane sultone - Google Patents
5363 purification method of 1,3-propane sultone Download PDFInfo
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- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 title claims abstract description 104
- 238000000034 method Methods 0.000 title claims abstract description 64
- 238000000746 purification Methods 0.000 title description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000012074 organic phase Substances 0.000 claims abstract description 34
- 238000002156 mixing Methods 0.000 claims abstract description 26
- 238000005191 phase separation Methods 0.000 claims abstract description 11
- 238000004821 distillation Methods 0.000 claims description 25
- 238000003756 stirring Methods 0.000 claims description 11
- 238000012958 reprocessing Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 239000000047 product Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000002994 raw material Substances 0.000 description 11
- 238000005406 washing Methods 0.000 description 10
- 239000010410 layer Substances 0.000 description 9
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 8
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000012535 impurity Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000007599 discharging Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000006277 sulfonation reaction Methods 0.000 description 4
- -1 1,3-propane sultone compound Chemical class 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- YVWGMAFXEJHFRO-UHFFFAOYSA-N halopropane Chemical compound FC(F)C(F)(F)CBr YVWGMAFXEJHFRO-UHFFFAOYSA-N 0.000 description 2
- 229950000188 halopropane Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
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- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 239000012847 fine chemical Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000048 melt cooling Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for purifying 1,3-propane sultone, which comprises the following steps: i) A mixing step of mixing molten 1,3-propane sultone with water to obtain a mixed system, and ii) an organic phase separation step of separating an organic phase containing 1,3-propane sultone, wherein the mixing temperature in the mixing step is 40-50 ℃.
Description
Technical Field
The invention belongs to the field of chemical industry, and particularly relates to purification treatment of small molecular compounds in fine chemical industry, and more particularly relates to a purification method of 1,3-propane sultone.
Background
1,3-propane sultone (1,2-Oxathiolane-2,2-dioxide) is colorless transparent crystal at room temperature, has melting point of 30-33 deg.C, boiling point of 180 deg.C/30 mmHg, and density (20 deg.C) of 1.392g/cm 3 . Sometimes also referred to simply as propane sultone, which has the following formula:
1,3-propane sultone compound is widely used in the industries of pharmaceutical chemicals, photosensitive materials, lithium batteries, biochemistry, spinning, lubrication, wastewater treatment, surface treatment and the like. Especially with the rise of clean energy sources, such as lithium secondary power batteries, it is also known as a widely used additive for lithium ion battery electrolytes.
The method for synthesizing 1,3-propane sultone is mature and can be obtained by sulfonation and condensation of allyl alcohol or acrolein as raw materials, and specific main synthesis methods can be listed as follows:
in one method, mainly using allyl alcohol and sodium bisulfite as raw materials, in the presence of an initiator, the target product is obtained through sulfonation, acidification, dehydration, purification and other steps, and specific reaction processes are as follows (for example, cited document 1):
in the method, acrolein and sodium bisulfite are mainly used as raw materials, and a target product is obtained through the steps of addition, reduction, lactonization, refining and the like, wherein the specific reaction equation is as follows:
in some other methods (for example, cited reference 2), direct dehydrative cyclization to form a lactone compound using a halopropane sulfonate has also been reported.
Wherein, the allyl alcohol is used as a raw material, and has high toxicity, and is inflammable and explosive; when acrolein is used as a raw material, an additional hydrogenation step is required. Therefore, as an alternative or improvement in terms of raw materials, citation 3, citation 4 and the like also attempt to react halopropanes as raw materials with a sulfonating agent.
It is also known that 1,3-propane sultone is generally required to have various aspects such as acidity, moisture content, purity, yan Sedu and the like as a raw material commonly used in the electronic and electric industry, and therefore, it is also an important problem for reprocessing or purifying 1,3-propane sultone, for example:
citation 5 discloses a method for reducing the acid value of 1,3-propane sultone by treating 1,3-propane sultone by adding an alkali-containing aqueous solution to an organic solvent, and finally obtaining a treated product by a distillation method; in the cited document 6, 1,3-propane sultone is treated with molecular sieve and finally distilled to obtain the final product.
In addition, cited document 7 discloses a method for purifying 1,3-propane sultone, which performs product purification by a melt-cooling crystallization method; citation 8 discloses a method of obtaining a purified product by subjecting 1,3-propane sultone to alcohol solution extraction followed by distillation.
It can be seen that there have been attempts in the art to produce, purify, etc. 1,3-propane sultone, but there is still room in the industry for improvement in the production and purification of 1,3-propane sultone.
Cited documents:
cited document 1: CN101012218A
Cited document 2: US3117133A
Cited document 3: CN 108218826A
Cited document 4: CN 108164502A
Cited document 5: CN102603704A
Cited document 6: CN104177326A
Cited document 7: CN107827865A
Cited document 8: CN 111560003A
Disclosure of Invention
Problems to be solved by the invention
As mentioned above, although there are many technical routes for the synthesis of 1,3-propane sultone, the final product is usually obtained by distillation or rectification. In addition, for the improvement of the characteristics of 1,3-propane sultone such as acid value and the like, after introducing other treatment steps, the 1,3-propane sultone product meeting the requirements is finally obtained by a distillation method.
However, it has also been found in long-term practice that although the known distillation or rectification methods generally also result in lactone products of higher purity, the operation is lengthy because the components or impurities present in the system to be treated can be complex, especially because the presence of particulate solid components therein can reduce the efficiency of the overall distillation process. However, an excessively long period of time or an increased number of distillations may cause a fear of causing troubles such as color tone and turbidity of the final product.
Further, cited document 8 discloses a method for purifying 1,3-propane sultone, which comprises adding an industrial-grade raw material in the form of a melt to an alcohol/water mixed system, stirring for 2 to 8 hours, then standing for 2 to 6 hours, separating a lower organic layer, and distilling again to obtain a final purified product, wherein 1,3-propane sultone is used as a purification target.
However, with reference 8, on the one hand, the treatment method disclosed therein is generally applicable only to reprocessing of 1,3-propane sultone product having a certain purity, and there is uncertainty as to whether it is applicable to industrial synthetic production of 1,3-propane sultone; on the other hand, when industrial grade 1,3-propane sultone is treated with an alcohol/water mixture system, since alcohol as an organic solvent is also water-soluble, it is very likely to cause an emulsification phenomenon during actual mixing, and further to cause an excessively long waiting time for aqueous phase/organic phase separation or a loss of the organic phase; in addition, there is also the disadvantage that, when 1,3-propane sultone in the molten state is added to the alcohol/water mixture, evaporation of the low-boiling alcohol results.
In view of the above problems in the art for the purification of 1,3-propane sultone, the primary object of the present invention is to provide a method for purifying 1,3-propane sultone, which significantly improves the purification efficiency, shortens the purification time, and avoids the deterioration or yield reduction caused by the too long purification treatment time by washing and filtering the lactone to be treated. In addition, the purification method of the invention has improved universality, is suitable for the process for synthesizing 1,3-propane sultone and is also suitable for the reprocessing of the existing 1,3-propane sultone finished product.
Means for solving the problems
After long-term research, the inventors of the present invention believe that the above technical problems can be solved by implementing the following technical solutions:
[1] the invention firstly provides a method for purifying 1,3-propane sultone, wherein the method comprises the following steps:
i) A mixing step of mixing the molten 1,3-propane sultone with water to obtain a mixed system, and,
ii) a step of separating the organic phase to separate an organic phase containing 1,3-propane sultone,
wherein the content of the first and second substances,
in the mixing step, the mixing temperature is 40-50 ℃.
[2] The method according to [1], wherein the water is used in an amount of 10 to 50 mass% based on the weight of 1,3-propane sultone in the step of i) mixing.
[3] The method according to [1] or [2], wherein the step of i) mixing is followed by the step of ii) organic phase separation after stirring and standing of the mixed system.
[4] The method according to any one of [1] to [3], wherein in the ii) organic phase separation step, the organic phase is separated from the bottom of the mixed system.
[5] The method according to any one of [1] to [4], wherein the temperature of the mixed system is maintained at 30 ℃ or higher in the ii) step of separating the organic phase.
[6] The method according to any one of [1] to [5], wherein the method performs the cyclic treatment of step i) and step ii) one or more times.
[7] The process according to any one of [1] to [6], wherein the ii) step of organic phase separation is followed by a step of distillation to obtain purified 1,3-propane sultone.
[8] Further, the present invention also provides a process for preparing 1,3-propane sultone, wherein the process comprises:
1,3-propane sultone chemical synthesis steps, and,
the method for purifying 1,3-propane sultone according to any of the above [1] to [7].
[9] Further, the present invention also provides a method for reprocessing 1,3-propane sultone, wherein the method comprises a step of purifying 1,3-propane sultone finished product using the method for purifying 1,3-propane sultone according to any one of the above [1] to [7].
[10] The method of [9], wherein the 1,3-propane sultone finished product has a purity that is less than chemically pure.
ADVANTAGEOUS EFFECTS OF INVENTION
Through the implementation of the technical scheme, the invention can obtain the following technical effects:
1) The purification method provided by the invention is simple to operate, has strong universality, is suitable for purifying 1,3-propane sultone products when 1,3-propane sultone is directly synthesized and produced, and is also suitable for re-purifying 1,3-propane sultone finished products (such as crude products or primary products and the like) with relatively low purity;
2) According to the invention, by washing 1,3-propane sultone with water before distillation, impurities which are easy to form solids and redundant water-soluble impurities are removed through water phase separation, so that the purpose of removing compound impurities is achieved, the subsequent distillation efficiency can be effectively improved, and the quality reduction of 1,3-propane sultone products caused by over-distillation is avoided.
Drawings
FIG. 1: process flow diagrams of some embodiments of the invention
Detailed Description
The present invention will be described in detail below. The technical features described below are explained based on typical embodiments and specific examples of the present invention, but the present invention is not limited to these embodiments and specific examples. It should be noted that:
in the present specification, the unit names used are international standard unit names unless otherwise specified.
In the present specification, "%" is used to mean weight or mass percent unless otherwise specified.
In the present specification, the numerical range represented by "a value a to B value" means a range including the endpoint value A, B.
In the present specification, the numerical ranges indicated by "above" or "below" mean the numerical ranges including the numbers.
In the present specification, the meaning of "may" includes both the meaning of performing a certain process and the meaning of not performing a certain process.
In the present specification, the expression "substantially" or "substantially" is used to indicate that the error from the reference is within 1%.
In the present specification, the term "room temperature" refers to a temperature condition of 25 ℃.
In the present specification, "chemically pure" means a purity of 99.5% or more; "analytically pure" means a purity of 99.7% or more; "guaranteed purity" is used to indicate a purity of 99.8% or more; "technical grade" purity is used to indicate a purity level of 95% purity.
In the present specification, reference to "some particular/preferred embodiments," "other particular/preferred embodiments," "embodiments," and the like, means that a particular element (e.g., feature, structure, property, and/or characteristic) described in connection with the embodiment is included in at least one embodiment described herein, and may or may not be present in other embodiments. In addition, it is to be understood that the described elements may be combined in any suitable manner in the various embodiments.
The invention provides a method for distilling and purifying 1,3-propane sultone, which is mainly based on the following findings: before distillation treatment, 1,3-propane sultone to be purified is mixed with water in a molten state, so that impurities which are easy to form solids in the 1,3-propane sultone to be purified and other water-soluble impurities are removed in advance, an organic layer containing 1,3-propane sultone is separated through an aqueous phase/organic phase, and the distillation process can be conveniently and quickly completed through distillation of the organic layer, so that a high-purity 1,3-propane sultone product is obtained. And, since the efficiency of distillation is improved, deterioration of quality of the distilled product, such as chromaticity, turbidity, etc., which is easily caused by excessive distillation in the prior art, can be avoided.
< first aspect >
In a first aspect of the invention, there is provided a method for purifying 1,3-propane sultone, wherein the method comprises: i) A mixing step to mix molten 1,3-propane sultone with water to obtain a mixed system, and ii) an organic phase separation step to separate an organic phase containing 1,3-propane sultone.
(to be purified 1,3-propane sultone)
In the present invention, there is no particular limitation on the source of 1,3-propane sultone to be purified. In some embodiments, it may be derived from a chemically synthesized (direct) product, or from a finished 1,3-propane sultone that has been prepared.
For a chemically synthesized (direct) product, it may be a direct product synthesized by various synthetic routes already existing in the art. In some specific embodiments, it may be a cyclized product obtained by subjecting allyl alcohol or acrolein as a raw material to sulfonation with a sulfonating agent and then to acidification; in other specific embodiments, the cyclized product obtained by subjecting a halopropane to sulfonation or the like, and the like.
In addition, the 1,3-propane sultone to be purified for the present invention can also be a finished product (crude product or primary product, etc.) of 1,3-propane sultone of relatively low purity. In some specific embodiments, such relatively low purity end products may have a purity that is less than chemically pure, e.g., technical and sub-technical, to further increase the purity of these 1,3-propane sultone end products by the purification methods provided by the present invention. Furthermore, in some other specific embodiments, as examples of further processing of the 1,3-propane sultone finished product, it may be cited that the 1,3-propane sultone to be purified for the present invention may also be derived from a system containing 1,3-propane sultone as a reprocessing to control acid value or ionic purity. In such a case, the acid value and the like are further adjusted by the addition of an inorganic treating agent, a solvent and the like, and therefore, it is necessary to perform purification again to obtain the final 1,3-propane sultone product.
(step of mixing)
In the mixing step of the present invention, 1,3-propane sultone to be treated is mixed with water.
Among them, 1,3-propane sultone was mixed in a molten state with water from the viewpoint of treatment efficiency. In some specific embodiments, the 1,3-propane sultone to be treated is heated to above 30 ℃, preferably above 35 ℃, more preferably above 40 ℃ and mixed with water that has been heated. The temperature of the heated water may be 40 ℃ or higher, preferably 40 to 50 ℃, more preferably 42 to 47 ℃.
After the mixed system is obtained, in some specific embodiments, the temperature of the mixed system is controlled to be in the range of 40 to 50 ℃, more preferably 42 to 57 ℃.
Regarding the mixing ratio of 1,3-propane sultone to be treated and water, from the viewpoint of suppressing hydrolysis and treatment efficiency, in some preferred embodiments, the amount of water is 10 to 50 mass%, preferably 12 to 40 mass%, more preferably 15 to 35 mass%, based on the weight of 1,3-propane sultone to be treated. However, if the amount of water used is too low, the removal of impurities may be incomplete when the two phases are separated, and if the amount of water used is too high, there is a possibility that hydrolysis may be unnecessarily caused.
In some other specific embodiments of the present invention, in the above-mentioned mixing step, as the solvent, in addition to water, an organic solvent which is immiscible with water (50 ℃ or lower) and can dissolve 1,3-propane sultone may be used (but a water-miscible organic solvent, such as a water-miscible alcohol, ether or ketone organic solvent, is not used).
The kind of such an organic solvent that can be used is not particularly limited, but those having a boiling point of 50 ℃ or higher and/or a density higher than that of water are preferable. The amount of the organic solvent used is not particularly limited, and is 20 mass% or less, preferably 15 mass% or less, and more preferably 10 mass% or less of the amount of water used in terms of the amount of water used in the treatment of efficiency. In some embodiments, the addition of an appropriate amount of a water-immiscible organic solvent can increase the efficiency of the aqueous/organic phase separation.
Further, after mixing 1,3-propane sultone to be treated with water, 1,3-propane sultone to be treated can be brought into sufficient contact with water by (mechanically) assisted dispersion means, and generally usable methods include vibration, mechanical stirring and the like. The treatment time of the auxiliary dispersion means is not particularly limited, and the auxiliary dispersion treatment time may be controlled to 20min or less, preferably 15min or less, and more preferably 10min or less, from the viewpoint of treatment efficiency and hydrolysis inhibition.
(step of organic phase separation)
The mixed system treated as described above may be allowed to stand to separate the aqueous phase from the organic phase.
There is no particular requirement for the time of standing, and since water is used as a solvent, the mixed system can be separated from the organic phase relatively quickly even after stirring. In some specific embodiments, the time of standing may be 30min or less, preferably 25min or less, e.g. 23min, 20min, 18min, 15min, 12min, or 10min, etc.
After the aqueous/organic phase is separated (stratified) in standing, the aqueous layer is above the organic layer, and therefore, the separation treatment can be performed by discharging the organic layer from the bottom of the apparatus.
In addition, in the step of separating the organic phase, the temperature of the mixed system, in some specific embodiments, may be controlled to a temperature of not lower than 30 ℃; in some preferred embodiments, the temperature of the system in the step of separating the organic phase may be kept in conformity with the temperature in the step of mixing, for example, controlled in the range of 40 to 50 ℃.
In the present invention, the apparatus used in the step of mixing and the step of separating the organic phase is not particularly limited in principle. Preferably, there may be stirring means, heating means and means with a bottom outlet. Preferably, the device has at least one visual window to facilitate viewing and monitoring of the separation of the organic phases.
(step of distillation)
In the present invention, after the step of separating the organic phase, the organic phase is collected, and further, the organic phase may be subjected to a distillation treatment.
The mode of the distillation is not particularly limited, and in some specific embodiments, the distillation may be performed by rotary evaporation, the heating temperature may be controlled between 140 to 160 ℃, and the fraction of 147 to 149 ℃ may be received. In addition, for the rotary evaporation, preferably, can be performed under the reduced pressure condition.
In other specific embodiments, the rectification may be carried out in a rectification column, where the pressure may be generally less than 10mmHg, the temperature in the reaction vessel may be controlled between 140 ℃ and 160 ℃, and the temperature at the top of the column may be controlled between 100 ℃ and 120 ℃.
Further, other auxiliary conditions for the distillation treatment are not particularly limited, and for example, optionally, a dehydrating agent or the like may be added before the distillation treatment.
In addition, according to the purification method of the present invention, the yield after distillation may be 95% by mass or more, preferably 96% by mass or more.
As typical embodiments that can be cited in the first aspect of the present invention, the following are:
(1) Starting a vacuum pump of the washing kettle, starting circulating water of a jacket of the washing kettle, and controlling the water temperature to be 45 +/-1; 140 kg of warm water (the water temperature is 45 ℃) is pumped into the water washing kettle, and 700 kg of melted 1,3-propane sultone crude product is pumped into the water washing kettle.
(2) Stirring for 5min, standing for 15min to allow solvent to separate layers, opening bottom valve, discharging the liquid at bottom layer of 1,3-propane sultone, observing rear view mirror, stopping discharging when water layer appears, and placing the residual water layer into water bucket.
< second aspect >
In a second aspect of the invention, the invention further provides a process for the preparation of 1,3-propane sultone and which comprises a purification process according to 1,3-propane sultone as described in the first aspect above.
Further, the method for preparing 1,3-propane sultone of the second aspect of the present invention comprises:
a step of preparing a cyclized product, and a step of purifying.
The step of producing the cyclized product is not particularly limited, and may be the same as the method of producing the cyclized product in < first aspect >, and the step of purifying may include the purification method in < first aspect > of the present invention.
In some particular embodiments, the purified 1,3-propane sultone obtained by the first or second aspects of the present invention has an analytically pure or greater purity, preferably a premium grade or greater purity. The acidity of 1,3-propanesultone is not particularly limited, and preferably is 100ppm or less.
In addition, the invention also provides a method for reprocessing or repurifying 1,3-propane sultone finished products, which includes the step of repurifying 1,3-propane sultone finished products using the purification method of the first aspect. The 1,3-propane sultone finished product, in some specific embodiments, has a purity that is less than chemically pure.
Example (b):
the technical solution of the present invention will be further explained by the following specific examples:
raw materials:
commercially pure 1,3-propane sultone: commercial purchase
Example 1
(1) Starting a vacuum pump of the washing kettle, starting circulating water of a jacket of the washing kettle, and controlling the water temperature to be 45 +/-1; 20 kg of warm water (the water temperature is 45 ℃) is pumped into the water washing kettle, and 100 kg of melted industrial pure 1,3-propane sultone is pumped into the water washing kettle.
(2) Starting stirring (rotating speed is 80 r/min), stirring for 5min, standing for 10min to allow the solvent to stratify, opening a bottom valve, discharging the liquid at the bottom layer of 1,3-propane sultone, observing a sight glass, stopping discharging when a water layer appears, and putting the residual water layer into a bucket.
(3) And distilling the separated organic phase, controlling the vacuum of a system to be below 10mmhg, controlling the kettle temperature to be 140-155 ℃, and completing the distillation within 2.5 hours, wherein the yield is about 96 percent, and the purity is GC grade (99.97 percent).
Comparative example 1 (cited document 8 the method of example 1 deals with technical gradePropane sultone)
1) Melting 100 parts of industrial-grade propane sultone at 40 ℃, and transferring the melted industrial-grade propane sultone to a reaction bottle to keep the temperature at 40 ℃;
2) Mixing 2 parts of methanol, 5 parts of isopropanol, 1 part of ethanol and 12 parts of pure water to prepare an alcohol solution; then adding the alcohol solution into the reaction bottle in the step (1) at 40 ℃ under the stirring condition of the rotation speed of 200rpm, stirring for 5 hours after adding the alcohol solution, and standing for 5 hours at 40 ℃ after stirring;
3) And (3) rotating the lower-layer liquid after standing in the step (2) for 1.5h at 90 ℃ by a conventional method at the rotating speed of 5rpm to obtain qualified propane sultone with the yield of 96% and the GC purity of 99.95%.
Table 1:
it can be seen that the purification process provided by the present invention can provide a level of purification comparable to the prior art in a shorter time.
It should be noted that, although the technical solutions of the present invention are described by specific examples, those skilled in the art can understand that the present disclosure should not be limited thereto.
The foregoing description of the embodiments of the present disclosure has been presented for purposes of illustration and description, but is not intended to be exhaustive or limited to the embodiments disclosed. Many modifications and variations will be apparent to those of ordinary skill in the art without departing from the scope and spirit of the described embodiments. The terminology used herein was chosen in order to best explain the principles of the embodiments, the practical application, or improvements to the technology in the marketplace, or to enable others of ordinary skill in the art to understand the embodiments disclosed herein.
Industrial applicability
The purification method of the invention can be industrially used for the purification treatment of 1,3-propane sultone.
Claims (10)
1. A method of purifying 1,3-propane sultone, comprising:
i) A mixing step of mixing the molten 1,3-propane sultone with water to obtain a mixed system, and,
ii) a step of separating the organic phase to separate an organic phase containing 1,3-propane sultone,
wherein the content of the first and second substances,
in the mixing step, the mixing temperature is 40-50 ℃.
2. The method of claim 1, wherein in the step of i) mixing, the water is used in an amount of 10 to 50 mass% based on the weight of 1,3-propane sultone.
3. The method according to claim 1 or 2, characterized in that the step of i) mixing is followed by the step of ii) organic phase separation after stirring and standing of the mixed system.
4. The method according to any one of claims 1 to 3, wherein in the step of ii) separating the organic phase, the organic phase is separated from the bottom of the mixed system.
5. The method according to any one of claims 1 to 4, wherein in the step of ii) separating the organic phase, the temperature of the mixed system is maintained at 30 ℃ or higher.
6. The method according to any one of claims 1 to 5, wherein the method is carried out in one or more cycles of steps i) and ii).
7. The process according to any of claims 1 to 6, characterized in that the step of ii) organic phase separation is followed by a step of distillation to obtain purified 1,3-propane sultone.
8. A method of making 1,3-propane sultone, comprising:
1,3-propane sultone chemical synthesis steps, and,
the method of purifying 1,3-propane sultone of any of claims 1-7.
9. A method for reprocessing 1,3-propane sultone, comprising the step of purifying 1,3-propane sultone by the method for purifying 1,3-propane sultone according to any of claims 1 to 7.
10. The method of claim 9, wherein the 1,3-propane sultone finished product has a purity that is less than chemically pure.
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