CN109485632B - Method for preparing cyclic sulfite - Google Patents
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- C07D327/10—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms two oxygen atoms and one sulfur atom, e.g. cyclic sulfates
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Abstract
The present invention relates to a process for the preparation of cyclic sulfites of the general formula (I) (wherein R is1、R2、R3、R4、R5And R6May be the same or different and each independently represents hydrogen, C substituted or unsubstituted with a halogen atom1～4Alkyl, or C substituted or unsubstituted by halogen atoms2～4Alkenyl group, n is 0, 1 or 2), and the production process is represented by the general formula (II) (wherein R is1、R2、R3、R4、R5、R6And n is the same as defined above) and a thionyl halide as a raw material, and continuously reacting sequentially through two reaction temperature zones, the temperature of the first reaction temperature zone being set within a range of 25 to 45 ℃, and the temperature of the second reaction temperature zone being set within a range of 50 to 100 ℃. The preparation method has high industrial feasibility, is safe and environment-friendly, does not use a catalyst, has low raw material cost, and can prepare high-purity cyclic sulfite with high yield.
Description
Technical Field
The present invention relates to a method for producing cyclic sulfite, and more particularly, to a method for producing cyclic sulfite through continuous reaction in two specific reaction temperature zones.
Background
Cyclic sulfites are widely used as an important organic chemical product, and are used as, for example, an acid generator, an alkylating agent, an intermediate for synthesis of alkanesulfonic acids, and the like, and particularly, have attracted attention as an electrolyte additive for lithium batteries and capacitors. For example, ethylene sulfite can form an SEI film on the negative electrode of a secondary lithium ion battery, thereby improving and improving the performance of the secondary lithium ion battery, and 1, 2-propylene glycol sulfite and 1, 3-propylene glycol sulfite can also be used as additives of the nonaqueous electrolyte of the lithium ion battery.
Conventionally, the above-mentioned method for producing a cyclic sulfite compound is usually carried out by a batch-type tank reaction using thionyl chloride and a glycol or an epoxy compound and sulfur dioxide. However, in the case of using thionyl chloride and glycols as reaction raw materials, for example, in the case of using ethylene glycol and thionyl chloride for reaction to produce ethylene sulfite, although the cost is low, it is generally necessary to use an excess of thionyl chloride to increase the reaction yield, but when thionyl chloride is used in an excess amount, a large amount of acid gas is generated by the reaction, a large amount of acid waste water is generated by post-treatment, and chlorohydrin impurities are easily generated, and purification is difficult, resulting in a high total chlorine content of the product. Especially when ethylene sulfite is used as a solvent or additive for an electrolyte of a lithium ion battery, chlorohydrin, which is a by-product, greatly affects the storage stability of the electrolyte in the electrolyte, thereby affecting the stability of a lithium ion secondary battery.
In view of the above, patent document 1 discloses a method for preparing ethylene sulfite, which is characterized in that dimethyl sulfite and ethylene glycol are used as raw materials, p-toluenesulfonic acid is used as a catalyst, the temperature is gradually increased from 60 to 70 ℃ to 160 to 180 ℃ in the reaction process, and simultaneously methanol generated in the reaction process is continuously removed, and the ethylene sulfite is further purified by fractional distillation to obtain ethylene sulfite. However, the purity of the crude product obtained by the method is low, the purity after rectification reaches 99 percent, and the use requirement of the lithium ion battery electrolyte additive still cannot be met. Patent document 2 discloses a method for producing vinyl sulfite by contact reaction of ethylene oxide with sulfur dioxide in the presence of a catalyst for 1 to 10 hours. Patent document 3 discloses a method for producing a cyclic sulfite by reacting an epoxy compound with sulfur dioxide in the presence of a silica catalyst having a surface modified with a tertiary amino group or a quaternary ammonium ionic group, wherein the reaction time is at least 3 hours or more. However, the methods of patent documents 2 and 3 require a long reaction time, and the use of sulfur dioxide and the high temperature and pressure of the reaction system cause operational inconvenience and safety problems in the production. In addition, the methods of patent documents 1 to 3 all use catalysts, which greatly increases the production cost.
Documents of the prior art
Patent document
[ patent document 1] Chinese patent CN1803767A
[ patent document 2] Chinese patent CN101210007A
[ patent document 3] Japanese patent application laid-open No. 2010-37322
Disclosure of Invention
Problems to be solved by the invention
In order to solve the problems in the prior art, the invention aims to provide a preparation method of cyclic sulfite, which has high industrial feasibility, is safe and environment-friendly, does not use a catalyst, has low raw material cost and high yield and product purity.
Means for solving the problems
The present invention provides the following:
(1) a preparation method of cyclic sulfite represented by a general formula (I) is characterized in that dihydric alcohol represented by a general formula (II) and halogenated thionyl are used as raw materials and sequentially undergo continuous reaction through two reaction temperature zones, wherein the temperature of a first reaction temperature zone is set within the range of 25-45 ℃, and the temperature of a second reaction temperature zone is set within the range of 50-100 ℃.
(in the formula, R1、R2、R3、R4、R5And R6May be the same or different and each independently represents hydrogen, C substituted or unsubstituted with a halogen atom1～4Alkyl, C substituted or unsubstituted by halogen atoms2～4Alkenyl, n is 0, 1 or 2. )
(in the formula, R1、R2、R3、R4、R5、R6And n is as defined above. )
(2) The method for preparing cyclic sulfite according to (1), wherein the reaction temperature zone is controlled by using a microchannel reaction device or a temperature-controlled tubular flow path to perform the reaction.
(3) The method for preparing the cyclic sulfite in the (1), wherein the first reaction temperature zone adopts a microchannel reaction device, and the second reaction temperature zone adopts a constant temperature water bath with a coil pipe arranged therein.
(4) The method for producing a cyclic sulfite according to (1), wherein the diol represented by the general formula (II) is ethylene glycol, 1, 2-propylene glycol, 1, 3-butylene glycol or 1, 4-butylene glycol, and the halogenated thionyl chloride is thionyl chloride.
(5) The method for preparing the cyclic sulfite according to the (1), wherein the temperature of the first reaction temperature zone is 30-45 ℃ and the temperature of the second reaction temperature zone is 65-85 ℃.
(6) The method for producing a cyclic sulfite according to (1), wherein the molar ratio of the diol to the halogenated thionyl is 1: 0.5-1: 2.
(7) the method for producing a cyclic sulfite according to (1), wherein the molar ratio of the diol to the halogenated thionyl is 1: 1.
(8) the method for producing a cyclic sulfite according to (1), wherein the continuous reaction time is 100 to 300 seconds.
(9) The method for producing a cyclic sulfite according to (1), wherein the continuous reaction time is 170 to 200 seconds.
Effects of the invention
The invention provides a brand new preparation process for preparing cyclic sulfite through continuous reaction, in particular to a microchannel reaction device, which realizes high purity and high yield of products while realizing continuous reaction by controlling reaction temperature and time, and greatly reduces the environmental protection cost for treating waste acid after reaction.
Compared with the prior art, the invention has the following advantages:
(1) no catalyst is used, and the raw material cost is reduced
(2) In the reaction process, the selectivity of the product is obviously improved, the side reaction is obviously reduced, the amount of the byproduct hydrogen chloride is reduced, the three wastes are reduced, and the method is more environment-friendly by controlling the temperature of the double-temperature zone.
(3) The whole reaction process is continuous reaction, and is safe and environment-friendly, and the production efficiency is high.
(4) The reaction yield and the product purity are obviously improved.
Drawings
FIG. 1 is a schematic flow chart of the method for producing cyclic sulfite according to the present invention.
Description of the symbols
1. A sample injection pump;
2. a sample injection pump;
3. a microchannel reactor;
4. constant temperature water bath with coil pipe inside
Detailed Description
The present invention will be described in detail below.
The cyclic sulfite represented by the following general formula (I) can be obtained by the present invention.
In the formula, R1、R2、R3、R4、R5And R6May be the same or different and each independently represents hydrogen, C substituted or unsubstituted with a halogen atom1～4Alkyl, C substituted or unsubstituted by halogen atoms2～4Alkenyl, n is 0, 1 or 2.
The halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
As C substituted or unsubstituted by halogen atoms1～4Alkyl is C1～4The hydrogen atom in the alkyl group may or may not be substituted by a halogen atom. As C substituted by halogen atoms1～4Examples of the alkyl group include chloromethyl, chloroethyl, and fluoromethyl. As unsubstituted C1～4Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group and a tert-butyl group.
As C substituted or unsubstituted by halogen atoms2～4Alkenyl means C2～4The hydrogen atom in the alkenyl group may or may not be substituted by a halogen atom. As C substituted by halogen atoms2～4Examples of the alkenyl group include a 2-chloroethenyl group and the like. As unsubstituted C2～4Examples of the alkenyl group include an ethenyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, and a 3-butenyl group.
The cyclic sulfite represented by the general formula (I) is not particularly limited, and may be a pentacyclic, hexacyclic or heptacyclic sulfite, and examples thereof include ethylene glycol sulfite, 1, 2-propylene glycol sulfite, 1, 3-propylene glycol sulfite, 1, 2-butylene glycol sulfite, 1, 3-butylene glycol sulfite, and 1, 4-butylene glycol sulfite.
In the method for producing a cyclic sulfite of the present invention, a diol represented by the general formula (II) and a thionyl halide are used as raw materials.
In the formula, R1、R2、R3、R4、R5、R6And n is as defined above for formula (I).
The diol represented by the general formula (II) is not particularly limited, and examples thereof include ethylene glycol, 1, 2-propanediol, 1, 3-propanediol, 1, 2-butanediol, 1, 3-butanediol, 1, 4-butanediol, 2, 3-butanediol, 3-butene-1, 2-diol, and 1, 1, 1-trifluoromethylpropanediol, with ethylene glycol being preferred.
Examples of the thionyl halide to be reacted with the diol represented by the general formula (II) include thionyl fluoride, thionyl chloride (thionyl chloride), thionyl bromide and the like, and among them, thionyl chloride is preferable in terms of low cost and easiness of handling. These halogenated sulfinyl groups may be used alone in 1 kind or in combination in plural kinds.
The invention is characterized in that the cyclic sulfite is prepared by continuous reaction, the reaction raw material is continuously and uninterruptedly input into a first reaction temperature zone (25-45 ℃) through an introducing device such as a pump, and after the reaction, the reaction raw material enters a second reaction temperature zone (50-100 ℃) for further reaction. The continuous reaction means that: different reaction raw materials continuously enter a continuous reactor to react at the same molar ratio, and different from a batch reactor, the raw materials can be continuously added, and reaction products can be continuously discharged. In the past, the preparation method of the cyclic sulfite mostly adopts batch reaction, namely, raw materials are added into a reactor at one time according to a certain proportion, materials are discharged at one time after the reaction meets certain requirements, and no material is added in and out in the reaction process.
In addition, the present invention is characterized in that a micro reaction channel device is used. The microchannel reaction device is usually made of special glass or special ceramic materials, the safe operating temperature range is-25-200 ℃, and the safe operating pressure range is 0-18 bar. Has excellent corrosion resistance, high temperature and high pressure resistance and is suitable for various chemical reactions. The inventor applies the microchannel reaction device to the preparation of the cyclic sulfite compounds for the first time, and obtains excellent effect.
Specifically, the present invention can employ the continuous reaction system shown in FIG. 1 to carry out the reaction. Before the reaction, the reaction system needs to be pretreated, that is, the glycol is introduced by the sample injection pump (1) at a high flow rate (for example, 30ml/min), and the preservation solution in the reaction system is rapidly and sufficiently replaced, so as to avoid the interference of the residue in the reaction system on the reaction and the influence on the reaction. After the preservation solution in the reaction system is completely and thoroughly replaced by the dihydric alcohol, the flow rate of the sampling pump (1) is reduced, and after the preservation solution is stabilized, the sampling pump (2) is started to introduce the halogenated thionyl chloride to start the reaction. In the reaction process, the flow rate of the sample pump (1) and the flow rate of the sample pump (2) are adjusted to control the molar ratio of the two raw materials, so that the molar ratio of the dihydric alcohol represented by the general formula (II) to the halogenated thionyl is 1: 0.5-1: 2, preferably 1: 1.
as shown in fig. 1, after the diol and the thionyl halide are introduced into the microchannel reactor (3) as the first reaction temperature zone by a sample pump, the reaction is performed in the microchannel reactor (3). In this step, the temperature (T1) of the microchannel reactor (3) is set to be in the range of 25 to 45 ℃. The reason for this is that when the temperature of T1 is lower than 25 ℃, the reaction does not proceed sufficiently, and the reaction yield decreases; when the temperature T1 is higher than 45 ℃, although the reaction yield may be improved, thionyl chloride is more corrosive and reacts violently, and a large amount of hydrogen halide (e.g., HCl) gas is instantaneously generated, so that the system pressure is instantaneously increased and the operational safety is deteriorated. Further, T1 is preferably in the range of 30 to 45 ℃ from the viewpoint of obtaining a high reaction yield and ensuring safe operation.
After the dihydric alcohol and the halogenated thionyl chloride react in the microchannel reaction device (3), the reaction mixture enters a constant temperature device (a constant temperature water bath with a coil pipe arranged therein is adopted in figure 1, and the temperature of the coil pipe is controlled at a specific temperature by adjusting the temperature of the water bath) in a second reaction temperature zone for further reaction until the reaction is finished. In this step, the temperature (T2) of the thermostat is set to be within a range of 50 to 100 ℃, preferably within a range of 65 to 85 ℃. By controlling the reaction temperature (T2) within the above-specified range, the reactants are sufficiently reacted, the reaction yield and the purity of the reaction product are improved, and excellent effects are obtained. If T2 is less than 50 ℃, the reaction product is insufficient, the residual content of the raw material ethylene glycol is high, and the reaction yield is lowered, while if T2 is more than 100 ℃, high-boiling impurities are likely to be present compared with vinyl sulfite, and the use of unnecessarily high temperatures is disadvantageous in industrial production, although the yield is somewhat increased.
In addition, when thionyl chloride is used as a reaction raw material, since the boiling point of thionyl chloride is 78 ℃, T2 is set to be not only higher than the boiling point, but also the yield can be improved by making the remaining small amount of unreacted thionyl chloride in a gaseous state and absorbing it as a tail gas together with hydrogen chloride, thereby making the acid content in the final product low and facilitating the neutralization by washing with water.
The apparatus used in the first reaction temperature zone and the second reaction temperature zone of the present invention is not particularly limited as long as the reaction temperature can be controlled within the above range, and a microchannel reaction apparatus may be used, or a tubular flow path having a controllable temperature (for example, a constant temperature water bath having a coil pipe therein) may be used. From the aspects of high purity, high yield, safety, environmental protection and the like, a microchannel reaction device is preferably used.
In addition, the cyclic sulfite is prepared through the continuous reaction system, and the continuous reaction time is 100-300 seconds, preferably 170-200 seconds. The continuous reaction time is the time for the reactants to pass through the continuous reactor, i.e. the total time for the raw materials to react in the first reaction temperature zone and the second reaction temperature zone after passing through. The reaction time can be adjusted based on the flow rate of the raw material, the internal volume of the apparatus, and the like.
After the reaction, the reaction product obtained from the thermostat was neutralized with water to remove acid, and then detected by gas chromatography.
Examples
The present invention will be described in further detail with reference to examples, but the present invention is not limited thereto.
The following devices were used in the examples:
a sample injection pump: (Dual pumpKP-22, CORNING)
Micro-channel reactor: (G1, CORNING)
A constant temperature device: the water bath of coil pipe is equipped with in, the coil pipe volume: 70ml, controllable temperature: 25-200 degree
Example 1
Raw materials of ethylene glycol (analytical reagent) and thionyl chloride (analytical reagent) were subjected to ultrasonic treatment for 20min to remove air bubbles in the raw materials, thereby stabilizing the flow rate of the sample pump.
In the reaction system shown in FIG. 1, the temperature (T1) of the microchannel reactor (3) was set to 30 ℃ and the water bath temperature was adjusted so that the coil temperature (T2) set therein was 85 ℃.
Setting the flow rate of a sample injection pump (1) to be 30ml/min, introducing the glycol subjected to bubble removal treatment, and injecting the sample for 10min to fully replace the preservation solution in the reaction system. Then, adjusting the flow rate of the sample pump (1) to be 13ml/min, starting the sample pump (2) to adjust the flow rate to be 17ml/min after the sample pump is stabilized, and introducing the thionyl chloride subjected to the bubble removal treatment to ensure that the molar ratio of the ethylene glycol to the thionyl chloride is 1: 1. the reaction time of the raw materials in the microchannel reactor (3) and the water bath (4) with the coil arranged therein is 170 s.
After completion of the reaction, a sample was taken out, neutralized to neutrality with water, and analyzed by gas chromatography (GC-2014C), and the results are shown in Table 1.
Examples 2 to 9
The reaction results are shown in Table 1, except that the molar ratio of ethylene glycol to thionyl chloride, T1, T2, reaction time and the like were changed as shown in Table 1, and the same were carried out as in example 1.
[ Table 1]
Based on the data in Table 1, it is understood that the production method of the present invention can rapidly produce high-purity ethylene glycol sulfite with high yield by performing the reaction in a two-temperature zone (T1 and T2). From the data of examples 1 to 3, it is found that as T2 increases, the purity of ethylene glycol sulfite becomes stable and the yield increases.
Comparative example 1
By adopting a traditional batch reaction mode, 5g of ethylene glycol is put into a round-bottom flask, 9.6g of thionyl chloride is added at 30 ℃ so that the molar ratio of the ethylene glycol to the thionyl chloride is 1: 1. after 180 seconds of reaction at 65 ℃, the reaction mixture was neutralized with sodium hydroxide lye and washed to neutrality, and the resulting organic phase was sampled and subjected to gas chromatography, the results of which are shown in table 2.
Comparative example 2
The reaction was carried out in the same manner as in example 1 except that T1 was set to 20 ℃ and the reaction was carried out in the same manner as in example 2, except that the isothermal apparatus was not used, that is, only a single temperature zone (T1) was provided during the reaction and the continuous reaction time was 100 seconds.
Comparative example 3
The reaction results are shown in Table 2, except that T1 was changed to 30 ℃.
Comparative example 4
The reaction results are shown in Table 2, except that T1 was set to 35 ℃.
Comparative example 5
The reaction results are shown in Table 2, except that T1 was changed to 40 ℃.
Comparative example 6
The reaction results are shown in Table 2, except that T1 was changed to 20 ℃ in the same manner as in example 3.
Comparative example 7
The reaction was carried out in the same manner as in example 1 except that T2 was changed to 30 ℃ and the results of the reaction are shown in Table 2.
Comparative example 8
The reaction results are shown in Table 2, except that T2 was changed to 35 ℃ in the same manner as in example 5.
[ Table 2]
Based on the data in Table 2, it can be seen that the purity of the ethylene glycol sulfite was 99.8% but the yield was only 30% when the conventional batch reaction was carried out instead of the continuous reaction (see comparative example 1). The main reason for this is considered to be that under ordinary stirring conditions, the reaction is not sufficient, the intermediate product formed is dissolved in water, and a large amount of raw material remains, and a large amount of acid solution is generated during washing with water, which makes the purification by post-treatment difficult and also causes the loss of product.
In comparative examples 2 to 5, only a single temperature zone (T1) was provided to carry out the continuous reaction. As is clear from Table 2, the reaction yield was very poor at 20 ℃ for T1, and was only 21%. The yield is improved with the temperature rise, which is considered to be mainly because the reactants of ethylene glycol and thionyl chloride in the micro-channel are gradually and fully mixed, and the conversion rate of the reaction is improved with the temperature rise. However, the reaction yield at 40 ℃ of T1 was still very low, reaching only 59%.
In comparative examples 6 to 8, although two temperature zones (T1 and T2) were provided to carry out the continuous reaction, the reaction temperature (T1 or T2) was not within the specific temperature range of the present invention, and the reaction yield was still low as compared with examples 1 to 8 of the present invention.
Example 9
The reaction was carried out in the same manner as in example 1 except that 1, 2-propanediol and thionyl chloride were used as starting materials and T1 was set to 35 ℃ and T2 was set to 85 ℃, and the results are shown in Table 3.
[ Table 3]
Example 01
The reaction was carried out in the same manner as in example 1 except that 1, 3-propanediol and thionyl chloride were used as starting materials and T1 was set to 35 ℃ and T2 was set to 85 ℃, and the results are shown in Table 4.
[ Table 4]
Example 11
The reaction was carried out in the same manner as in example 1 except that 1, 4-butanediol and thionyl chloride were used as the starting materials and T1 was set to 35 ℃ and T2 was set to 85 ℃, and the results are shown in Table 5.
[ Table 5]
The results of the above tables 3 to 5 show that 1, 2-propanediol sulfite, 1, 3-propanediol sulfite and 1, 4-butanediol sulfite with high purity can be rapidly prepared in high yield by the preparation method of the present invention.
Claims (8)
1. A preparation method of cyclic sulfite represented by a general formula (I) is characterized in that dihydric alcohol represented by a general formula (II) and halogenated thionyl are used as raw materials and sequentially subjected to continuous reaction through two reaction temperature zones, the temperature of a first reaction temperature zone is set to be within a range of 25-45 ℃, the temperature of a second reaction temperature zone is set to be within a range of 65-85 ℃, a microchannel reaction device is adopted in the first reaction temperature zone, the temperature of the second reaction temperature zone is controlled by a microchannel reaction device or a temperature-controllable tubular flow path for reaction,
in the formula, R1、R2、R3、R4、R5And R6May be the same or different and each independently represents hydrogen, C substituted or unsubstituted with a halogen atom1～4Alkyl, or C substituted or unsubstituted by halogen atoms2～4Alkenyl, n is 0, 1 or 2,
in the formula, R1、R2、R3、R4、R5、R6And n is as defined above.
2. The method according to claim 1, wherein the first reaction temperature zone is a microchannel reaction apparatus, and the second reaction temperature zone is a constant temperature water bath having a coil pipe therein.
3. The method for producing a cyclic sulfite according to claim 1,
the dihydric alcohol represented by the general formula (II) is ethylene glycol, 1, 2-propylene glycol, 1, 3-butanediol or 1, 4-butanediol,
the halogenated thionyl chloride is thionyl chloride.
4. The method for preparing cyclic sulfite according to claim 1, wherein the temperature of the first reaction temperature zone is 30 to 45 ℃.
5. The method for preparing a cyclic sulfite according to claim 1, wherein the molar ratio of the diol to the halogenated thionyl is 1: 0.5-1: 2.
6. the method for preparing a cyclic sulfite according to claim 1, wherein the molar ratio of the diol to the halogenated thionyl is 1: 1.
7. the method according to claim 1, wherein the continuous reaction time is 100 to 300 seconds.
8. The method according to claim 1, wherein the continuous reaction time is 170 to 200 seconds.
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| CN1037510A (en) * | 1988-03-08 | 1989-11-29 | 罗纳-布朗克制药公司 | The preparation method of cyclic sulfates |
| CN101210007A (en) * | 2006-12-31 | 2008-07-02 | 比亚迪股份有限公司 | Method for preparing ethylene sulfite |
| CN101880270A (en) * | 2009-05-07 | 2010-11-10 | 上海华升化工科技有限公司 | Method for preparing 1,1-cyclopropanedimethyl cyclicsulfite |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1037510A (en) * | 1988-03-08 | 1989-11-29 | 罗纳-布朗克制药公司 | The preparation method of cyclic sulfates |
| CN101210007A (en) * | 2006-12-31 | 2008-07-02 | 比亚迪股份有限公司 | Method for preparing ethylene sulfite |
| CN101880270A (en) * | 2009-05-07 | 2010-11-10 | 上海华升化工科技有限公司 | Method for preparing 1,1-cyclopropanedimethyl cyclicsulfite |
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| Øystein Rist等.《Synthesis of Hydroxy Sulfonate Surfactants》.《Molecules》.2005,第10卷 * |
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