阅读说明：本技术 一种莽草酸磺化物及其制备方法 (Shikimic acid sulfonated substance and preparation method thereof ) 是由 陈燕飞 周嘉宁 徐飞飞 陈君利 于 2021-06-29 设计创作，主要内容包括：本发明提供了一种莽草酸磺化物及其制备方法。莽草酸磺化物的制备方法包括以下步骤：S100、采用包括莽草酸醚类化合物和甲基磺酰氯的原料,添加阴离子交换树脂作为缚酸剂,在有机溶剂中进行磺化反应,获得莽草酸磺化物。本发明提供的莽草酸磺化物的制备方法具有反应温和、反应温度范围广的优势。(The invention provides a shikimic acid sulfonated substance and a preparation method thereof. The preparation method of the shikimic acid sulfonated comprises the following steps: s100, adding anion exchange resin as an acid-binding agent into raw materials comprising shikimic acid ether compounds and methylsulfonyl chloride, and carrying out sulfonation reaction in an organic solvent to obtain a shikimic acid sulfonated substance. The preparation method of the shikimic acid sulfonate provided by the invention has the advantages of mild reaction and wide reaction temperature range.)

1. A preparation method of shikimic acid sulfonate is characterized by comprising the following steps:

s100, adding anion exchange resin as an acid-binding agent into raw materials comprising shikimic acid ether compounds and methylsulfonyl chloride, and carrying out sulfonation reaction in an organic solvent to obtain the shikimic acid sulfonated substance.

2. The process for the preparation of shikimic acid sulfonate according to claim 1, characterized in that,

the addition amount of the shikimic acid ether compounds is 1eq, the addition amount of the methylsulfonyl chloride is 1.0eq to 1.2eq, the addition amount of the organic solvent is 8 times to 12 times of the total addition amount of the shikimic acid ether compounds and the methylsulfonyl chloride, and the addition amount of the anion exchange resin is 10 times to 20 times of the addition amount of the shikimic acid ether compounds;

the reaction time of the sulfonation reaction is 0.5h to 1.5h, and the reaction temperature of the sulfonation reaction is-15 ℃ to 30 ℃.

3. The process for the preparation of shikimic acid sulfonate according to claim 1, characterized in that,

the addition amount of the shikimic acid ether compounds is 1eq, the addition amount of the methylsulfonyl chloride is 1.1eq, the addition amount of the organic solvent is 10 times of the total addition amount of the shikimic acid ether compounds and the methylsulfonyl chloride, and the addition amount of the anion exchange resin is 15 times of the addition amount of the shikimic acid ether compounds;

the reaction time of the sulfonation reaction is 1h, and the reaction temperature of the sulfonation reaction is-5 ℃ to 20 ℃.

4. The process for the preparation of shikimic acid sulfonate according to claim 1, characterized in that,

the anion exchange resin is at least one of the following or a combination thereof:

amberjet4000CL strongly basic anion exchange resin, Amberjet4200CL strongly basic anion exchange resin, amberlite ira401CL strongly basic anion exchange resin, amberlite ira402CL strongly basic anion exchange resin, amberlite ira410CL strongly basic anion exchange resin, amberlite ira458CL strongly basic anion exchange resin, amberlite ira458RFCL strongly basic anion exchange resin, amberlite ira478RFCL strongly basic anion exchange resin, amberlite ira 46900 strongly basic anion exchange resin, Amberjet up4000 strongly basic anion exchange resin, Amberjet 9848300 strongly basic anion exchange resin, Ambersep900SO4 strongly basic anion exchange resin, Amberjet4500CL strongly basic anion exchange resin, Amberjet4500(OH) strongly basic anion exchange resin, IMACHP555 strongly basic anion exchange resin, Amberjet fpela 90 strongly basic anion exchange resin, Amberjet fpea 3698 strongly basic anion exchange resin, Amberjet 1 strongly basic anion exchange resin;

the organic solvent is at least one of the following or a combination thereof:

ethyl acetate, dichloromethane, trichloromethane.

5. The method for preparing shikimic acid sulfonate according to claim 1, wherein said S100 specifically comprises:

uniformly mixing the shikimic acid ether compound and the organic solvent, adding the methylsulfonyl chloride, adding the anion exchange resin as an acid-binding agent, and performing the sulfonation reaction for 1h at the temperature of between-5 and 20 ℃ to obtain the shikimic acid sulfonated compound.

6. The process for the preparation of shikimate sulfonate according to claim 1, wherein after said S100, said process further comprises:

s200, recovering the anion exchange resin, soaking the anion exchange resin by adopting an alkaline pH value regulator, washing the anion exchange resin to be neutral after soaking is finished, and drying the anion exchange resin.

7. The process for the preparation of shikimic acid sulfonate according to any of claims 1 to 6, characterized in that the reaction formula of the sulfonation reaction is as follows:

wherein the shikimic acid ether compound contained in the raw materials of the sulfonation reaction is a binary shikimic acid ether compound.

8. The process for the preparation of shikimate sulfonate according to any one of claims 1 to 6, characterized in that the shikimate ether compound is obtained by:

the shikimic acid ether compound is obtained by chemical reaction of raw materials comprising shikimic acid ester compounds and ketone compounds under the catalysis of cation exchange resin.

9. The process for the preparation of shikimate sulfonate according to any one of claims 1 to 6, characterized in that the shikimate ether compound is obtained by:

the method comprises the following steps of (1) obtaining shikimate compounds through chemical reaction by using raw materials comprising shikimic acid and alcohol compounds under the catalytic action of cation exchange resin;

the shikimic acid ether compound is obtained by chemical reaction of raw materials comprising the shikimic acid ester compound and ketone compound under the catalysis of cation exchange resin.

10. A shikimate sulfonate obtained by the process according to any one of claims 1 to 9.

Technical Field

The invention relates to the technical field of chemical raw material treatment, in particular to a shikimic acid sulfonated substance and a preparation method thereof.

Background

Shikimic acid is a monomer compound extracted from Chinese medicine star anise, and its molecular formula is C₇H₁₀O₅. The shikimic acid is colorless or white needle crystal, has solubility of 18% in water at 20 deg.C, is slightly soluble in ethanol and diethyl ether, and is hardly soluble in chloroform and benzene. The shikimic acid sulfonated and shikimic acid ether compounds are shikimic acid compounds. Wherein, the shikimic acid ether compound is used as the raw material to prepare the shikimic acid sulfonated substance. However, the above reaction processes are generally severe and have some low adverse effects on production safety. Therefore, how to improve the safety and controllability of production when preparing shikimic acid sulfonate is a technical problem to be solved urgently by the technical personnel in the field.

Disclosure of Invention

The present invention is directed to solving at least one of the above problems.

Therefore, the first purpose of the invention is to provide a preparation method of shikimic acid sulfonate.

The second purpose of the invention is to provide a shikimic acid sulfonated substance.

To achieve the first object of the present invention, an embodiment of the present invention provides a method for preparing shikimic acid sulfonate, comprising the following steps:

s100, adding anion exchange resin as an acid-binding agent into raw materials comprising shikimic acid ether compounds and methylsulfonyl chloride, and carrying out sulfonation reaction in an organic solvent to obtain a shikimic acid sulfonated substance.

In any of the above technical schemes, the addition amount of shikimic acid ether compound is 1 eq.

In any of the above technical schemes, the amount of methanesulfonyl chloride added is 1.0eq to 1.2 eq.

In any of the above technical schemes, the addition amount of the organic solvent is 8-12 times of the total addition amount of the shikimic acid ether compound and the methylsulfonyl chloride.

In any of the above technical schemes, the addition amount of the anion exchange resin is 10 times to 20 times of the addition amount of the shikimic acid ether compound.

In any of the above technical schemes, the reaction time of the sulfonation reaction is 0.5h to 1.5 h.

In any of the above technical schemes, the reaction temperature of the sulfonation reaction is-15 ℃ to 30 ℃.

In any of the above technical schemes, the addition amount of shikimic acid ether compound is 1 eq.

In any of the above technical solutions, the amount of methanesulfonyl chloride added is 1.1 eq.

In any of the above technical schemes, the addition amount of the organic solvent is 10 times of the total addition amount of the shikimic acid ether compound and the methylsulfonyl chloride.

In any of the above technical schemes, the addition amount of the anion exchange resin is 15 times of the addition amount of the shikimic acid ether compound.

In any of the above technical schemes, the reaction time of the sulfonation reaction is 1 h.

In any of the above technical schemes, the reaction temperature of the sulfonation reaction is-5 ℃ to 20 ℃.

In any of the above embodiments, the anion exchange resin is at least one of the following or a combination thereof: amberjet4000CL strongly basic anion exchange resin, Amberjet4200CL strongly basic anion exchange resin, Amberlite IRRA 401CL strongly basic anion exchange resin, Amberlite IRRA 402CL strongly basic anion exchange resin, Amberlite IRRA 410CL strongly basic anion exchange resin, Amberlite IRRA 458CL strongly basic anion exchange resin, Amberlite IRRA 458RFCL strongly basic anion exchange resin, Amberlite IRRA 478RFCL strongly basic anion exchange resin, Amberlite IRRA 46900 strongly basic anion exchange resin, Amberjet UP4000 strongly basic anion exchange resin, Amberjet 9848300 strongly basic anion exchange resin, Ambersep900SO4 strongly basic anion exchange resin, Amberjet4500CL strongly basic anion exchange resin, Amberjet4500(OH) strongly basic anion exchange resin, IMACHP555 strongly basic anion exchange resin, Amberjet FPeEA 90 strongly basic anion exchange resin, Amberjet 1 strongly basic anion exchange resin, Amberjet FPE 3698 type strongly basic anion exchange resin.

In any of the above technical solutions, the organic solvent is at least one of the following or a combination thereof: ethyl acetate, dichloromethane, trichloromethane.

In any of the above technical solutions, S100 specifically includes:

uniformly mixing shikimic acid ether compounds and an organic solvent, adding methylsulfonyl chloride, adding anion exchange resin as an acid-binding agent, and carrying out sulfonation reaction for 1h at the temperature of-5 ℃ to 20 ℃ to obtain a shikimic acid sulfonated product.

In any of the above technical solutions, after S100, the preparation method further includes:

s200, recovering the anion exchange resin, soaking the anion exchange resin by adopting an alkaline pH value regulator, washing the anion exchange resin to be neutral after soaking is finished, and drying the anion exchange resin.

In any of the above technical schemes, the reaction formula of the sulfonation reaction is as follows:

wherein, the shikimic acid ether compound contained in the raw materials of the sulfonation reaction is a binary shikimic acid ether compound.

In any of the above technical schemes, the shikimic acid ether compound is obtained by the following steps:

the shikimic acid ether compound is obtained by chemical reaction of raw materials comprising shikimic acid ester compounds and ketone compounds under the catalysis of cation exchange resin.

In any of the above technical schemes, the shikimic acid ether compound is obtained by the following steps:

the method comprises the following steps of (1) obtaining shikimate compounds through chemical reaction by using raw materials comprising shikimic acid and alcohol compounds under the catalytic action of cation exchange resin;

the shikimic acid ether compound is obtained by chemical reaction of raw materials comprising shikimic acid ester compounds and ketone compounds under the catalysis of cation exchange resin.

The preparation method of the shikimic acid sulfonate provided by the invention has the advantages of mild reaction and wide reaction temperature range. Therefore, the method can improve the safety and the controllable degree of production, can also reduce the requirement on temperature control in the reaction and reduce the production difficulty.

To achieve the second object of the present invention, an embodiment of the present invention provides a shikimate sulfonate, which is obtained by the preparation method according to any one of the embodiments of the present invention.

The shikimate sulfonate provided by the embodiment of the invention is obtained by the preparation method of the shikimate sulfonate provided by any embodiment of the invention, so that the shikimate sulfonate has all the beneficial effects of the preparation method of the shikimate sulfonate provided by any embodiment of the invention, and the details are not repeated.

Additional aspects and advantages of the invention will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention.

Detailed Description

In order that the above objects, features and advantages of the present invention can be more clearly understood, the present invention will be described in further detail with reference to specific embodiments. It should be noted that the embodiments and features of the embodiments of the present application may be combined with each other without conflict.

In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, however, the present invention may be practiced in other ways than those specifically described herein, and therefore the scope of the present invention is not limited by the specific embodiments disclosed below.

In the examples of the present invention, eq (equivalent) was used as a unit for measuring the amount of each raw material added. eq refers to an amount equivalent to a specific or trivial value, used as a reference for the mass ratio at which the substances interact.

It should be noted that, in the embodiments of the present invention, a person skilled in the art may use a device in the prior art, such as a chemical reflux device, a reaction tower, etc., to implement the reactions involved in the following preparation methods. The equipment adopted in the preparation method is not limited in the embodiment of the invention.

The embodiment of the invention provides a preparation method of shikimic acid sulfonate, which comprises the following steps:

s100, adding anion exchange resin as an acid-binding agent into raw materials comprising shikimic acid ether compounds and methylsulfonyl chloride, and carrying out sulfonation reaction in an organic solvent to obtain a shikimic acid sulfonated substance.

The shikimic acid ether compound adopted in the above steps can be obtained by reacting shikimic acid ester compound, the shikimic acid ester compound can be obtained by esterifying shikimic acid, and shikimic acid can be extracted from Chinese medicine star anise. The methanesulfonyl chloride used in the above step is commercially available.

The reaction yield of the above reaction is 98% to 100%. Wherein, the reaction yield refers to the ratio of the actually produced product yield obtained by inputting unit quantity of raw materials to the theoretically calculated product yield in the chemical reaction or related chemical industrial production.

Alternatively, in some embodiments of the above examples, the anion exchange resin is at least one of, or a combination of: amberjet4000CL strongly basic anion exchange resin, Amberjet4200CL strongly basic anion exchange resin, Amberlite IRRA 401CL strongly basic anion exchange resin, Amberlite IRRA 402CL strongly basic anion exchange resin, Amberlite IRRA 410CL strongly basic anion exchange resin, Amberlite IRRA 458CL strongly basic anion exchange resin, Amberlite IRRA 458RFCL strongly basic anion exchange resin, Amberlite IRRA 478RFCL strongly basic anion exchange resin, Amberlite IRRA 46900 strongly basic anion exchange resin, Amberjet UP4000 strongly basic anion exchange resin, Amberjet 9848300 strongly basic anion exchange resin, Ambersep900SO4 strongly basic anion exchange resin, Amberjet4500CL strongly basic anion exchange resin, Amberjet4500(OH) strongly basic anion exchange resin, IMACHP555 strongly basic anion exchange resin, Amberjet FPeEA 90 strongly basic anion exchange resin, Amberjet 1 strongly basic anion exchange resin, Amberjet FPE 3698 type strongly basic anion exchange resin.

Alternatively, in some embodiments of the above examples, the amount of shikimate ether compound added is 1 eq.

Alternatively, in some embodiments of the above examples, the amount of methanesulfonyl chloride added is from 1.0eq to 1.2 eq.

Alternatively, in some embodiments of the above examples, methanesulfonyl chloride is added in an amount of 1.1 eq.

Alternatively, in some embodiments of the above examples, the amount of organic solvent added is 8 to 12 times the total amount of shikimate ether compound and methylsulfonyl chloride added.

Alternatively, in some embodiments of the above examples, the amount of organic solvent added is 9 to 11 times the total amount of shikimate ether compound and methylsulfonyl chloride added.

Alternatively, in some embodiments of the above examples, the amount of organic solvent added is 10 times the total amount of shikimate ether compound and methylsulfonyl chloride added.

Alternatively, in some embodiments of the above examples, the amount of anion exchange resin added is 10 to 20 times the amount of shikimate ether compound added.

Alternatively, in some embodiments of the above examples, the amount of anion exchange resin added is 12 to 18 times the amount of shikimate ether compound added.

Alternatively, in some embodiments of the above examples, the amount of anion exchange resin added is 15 times the amount of shikimate ether compound added.

Alternatively, in some embodiments of the above examples, the reaction time for the sulfonation reaction is 0.5h to 1.5 h.

Alternatively, in some embodiments of the above examples, the reaction time for the sulfonation reaction is 1 hour.

Alternatively, in some embodiments of the above examples, the reaction temperature of the sulfonation reaction is from-15 ℃ to 30 ℃.

Alternatively, in some embodiments of the above examples, the reaction temperature of the sulfonation reaction is from-10 ℃ to 25 ℃.

Alternatively, in some embodiments of the above examples, the reaction temperature of the sulfonation reaction is from-5 ℃ to 20 ℃.

Optionally, in some embodiments of the above examples, the organic solvent is at least one of the following or a combination thereof: ethyl acetate, dichloromethane, trichloromethane.

Alternatively, in some embodiments of the above examples, the organic solvent is a mixture of ethyl acetate, dichloromethane, and chloroform.

Optionally, in some implementations of the foregoing embodiments, S100 specifically includes:

uniformly mixing shikimic acid ether compounds and an organic solvent, adding methylsulfonyl chloride, adding anion exchange resin as an acid-binding agent, and carrying out sulfonation reaction for 1h at the temperature of-5 ℃ to 20 ℃ to obtain a shikimic acid sulfonated product.

Alternatively, in some embodiments of the above examples, after S100, the preparation method further comprises:

s200, recovering the anion exchange resin, soaking the anion exchange resin by adopting an alkaline pH value regulator, washing the anion exchange resin to be neutral after soaking is finished, and drying the anion exchange resin.

The recycling of the anion exchange resin can realize the reuse of the anion exchange resin, thereby reducing the production cost.

Alternatively, in some embodiments of the above examples, the sulfonation reaction is as follows:

wherein, the shikimic acid ether compound contained in the raw materials of the sulfonation reaction is a binary shikimic acid ether compound.

In other words, S100 specifically includes:

the method comprises the steps of adding anion exchange resin as an acid-binding agent into raw materials comprising binary shikimic acid ether compounds and methylsulfonyl chloride, and carrying out sulfonation reaction in organic solvents such as ethyl acetate, dichloromethane, trichloromethane and the like to obtain a shikimic acid sulfonated substance.

The anion exchange resin used in the above step is used as an acid-binding agent in the reaction. In the related art, sulfonation of shikimate etherate is usually carried out in triethylamine, methanesulfonyl chloride, reaction temperature is-5 to 5 ℃, which has problems that: the reaction exothermed, impurities were abundant, and triethylamine was consumed. Compared with the technical scheme of carrying out reaction in triethylamine and methanesulfonyl chloride in the related technology, the step adopts anion exchange resin as an acid-binding agent, and has the advantages of mild reaction and wide reaction temperature range. Except for mild reaction, the temperature rise of the steps is slow, impurities in the product are less, triethylamine is not consumed, and only conventional inorganic acid and alkali are consumed.

Alternatively, in some embodiments of the above examples, the shikimate ether compound is obtained by: the shikimic acid ether compound is obtained by chemical reaction of raw materials comprising shikimic acid ester compounds and ketone compounds under the catalysis of cation exchange resin.

Alternatively, in some embodiments of the above examples, the reaction is as follows:

wherein, the shikimate ester compound contained in the raw materials of the reaction is shikimate ethyl ester, the ketone compound contained in the raw materials of the reaction is acetone, and the product of the reaction is a binary shikimate ether compound.

Alternatively, in some embodiments of the above examples, the reaction is as follows:

wherein, the shikimate ester compound contained in the raw materials of the reaction is shikimate ethyl ester, the ketone compound contained in the raw materials of the reaction is 3-pentanone, and the product of the reaction is a ternary shikimate ether compound.

Alternatively, in some embodiments of the above examples, the cation exchange resin is a strong acid cation exchange resin having a solid form.

Alternatively, in some embodiments of the above examples, the strong acid cation exchange resin is at least one of, or a combination of: amberlite IR100Na strong acid cation exchange resin, Amberlite IR120Na strong acid cation exchange resin, Amberlite IR120H strong acid cation exchange resin, Amberjet 1000Na strong acid cation exchange resin, Amberjet 1200H strong acid cation exchange resin, Amberjet 1300Na strong acid cation exchange resin, Amberjet UP1400 strong acid cation exchange resin, Amberlite IRN97H strong acid cation exchange resin, Ambersep p 252H strong acid cation exchange resin, Amberjet 1500H strong acid cation exchange resin, Amberlite SR1L Na strong acid cation exchange resin, IMAC HP1110 Na strong acid cation exchange resin.

Alternatively, in some embodiments of the above examples, an esterification dehydration tower may be used as a reaction device, cation exchange resin is added to the esterification dehydration tower as a filler, shikimate compound is added from the top of the esterification dehydration tower, ketone compound is added from the bottom of the esterification dehydration tower, the temperature of the reaction system is maintained at 40 ℃ to 70 ℃, and heat preservation is performed for 3 hours, so as to obtain shikimate ether compound. Wherein the addition amount of the shikimate compounds is 1eq, the addition amount of the ketone compounds is 1000eq to 3000eq, and the addition amount of the cation exchange resin is 1.5 times to 2.5 times of the addition amount of the shikimate compounds. The reaction time is 1-5 h, and the reaction temperature is 40-70 ℃.

The steps adopt the cation exchange resin as the catalyst, the cation exchange resin is convenient to recycle, the repeated application of the catalyst can be realized, and the production cost is reduced. In addition, the preparation method provided by the invention can obtain a product with less impurities, is more friendly to equipment, has low corrosion degree to the equipment, and reduces the maintenance cost of the equipment.

Alternatively, in some embodiments of the above examples, the shikimate ether compound is obtained by:

the method comprises the following steps of (1) obtaining shikimate compounds through chemical reaction by using raw materials comprising shikimic acid and alcohol compounds under the catalytic action of cation exchange resin;

the shikimic acid ether compound is obtained by chemical reaction of raw materials comprising shikimic acid ester compounds and ketone compounds under the catalysis of cation exchange resin.

Wherein, the shikimate ether compound is obtained by using the raw material comprising shikimate ester compound and ketone compound in the manner as described above. The mode for obtaining the shikimate compound by adopting the raw materials comprising shikimic acid and the alcohol compound is concretely as follows.

The raw materials comprising shikimic acid and alcohol compounds are adopted to carry out esterification reaction under the catalysis of cation exchange resin, so as to obtain the shikimate compounds.

Alternatively, in some embodiments of the above examples, the strong acid cation exchange resin is at least one of, or a combination of: amberlite IR100Na strong acid cation exchange resin, Amberlite IR120Na strong acid cation exchange resin, Amberlite IR120H strong acid cation exchange resin, Amberjet 1000Na strong acid cation exchange resin, Amberjet 1200H strong acid cation exchange resin, Amberjet 1300Na strong acid cation exchange resin, Amberjet UP1400 strong acid cation exchange resin, Amberlite IRN97H strong acid cation exchange resin, Ambersep p 252H strong acid cation exchange resin, Amberjet 1500H strong acid cation exchange resin, Amberlite SR1L Na strong acid cation exchange resin, IMAC HP1110 Na strong acid cation exchange resin.

Alternatively, in some embodiments of the above examples, an esterification dehydration tower may be used as the reaction equipment for esterification reaction, cation exchange resin is added to the esterification dehydration tower as a filler, shikimic acid is added from the top of the esterification dehydration tower, alcohol compound is added from the bottom of the esterification dehydration tower, the temperature of the reaction system for esterification reaction is maintained at 40 ℃ to 100 ℃, and the temperature is maintained for 10 hours, so as to obtain shikimate ester compound. Wherein the addition amount of shikimic acid is 1eq, the addition amount of the alcohol compound is 1000eq to 3000eq, and the addition amount of the cation exchange resin is 1.5 times to 2.5 times of the addition amount of shikimic acid. The reaction time of the esterification reaction is 8 to 12 hours, and the reaction temperature of the esterification reaction is 40 to 100 ℃.

The steps adopt cation exchange resin as a catalyst, which can avoid the generation of waste gas and improve the environmental protection degree of the reaction. In addition, the preparation method of the shikimate compound provided by the invention can obtain a product with less impurities, is more friendly to equipment, has low corrosion degree to the equipment, and reduces the maintenance cost of the equipment.

Example 1

This example provides a method for preparing a shikimic acid sulfonate, which is as follows. Uniformly mixing the shikimic acid ether compound and the organic solvent. Wherein the addition amount of shikimic acid ether compound is 1 eq. The organic solvent is ethyl acetate, and the addition amount of the organic solvent is 8 times of the total addition amount of the shikimic acid ether compound and the methylsulfonyl chloride. After mixing well, methanesulfonyl chloride is added. The amount of methanesulfonyl chloride added was 1.0 eq. Further adding anion exchange resin as an acid-binding agent. The addition amount of the anion exchange resin is 10 times of that of the shikimic acid ether compound. Carrying out sulfonation reaction for 1.5h at the temperature of-15 ℃ to obtain shikimic acid sulfonated product.

Example 2

This example provides a method for preparing a shikimic acid sulfonate, which is as follows. Uniformly mixing the shikimic acid ether compound and the organic solvent. Wherein the addition amount of shikimic acid ether compound is 1 eq. The organic solvent is dichloromethane, and the addition amount is 12 times of the total addition amount of the shikimic acid ether compound and the methylsulfonyl chloride. After mixing well, methanesulfonyl chloride is added. The amount of methanesulfonyl chloride added was 1.2 eq. Further adding anion exchange resin as an acid-binding agent. The addition amount of the anion exchange resin is 20 times of that of the shikimic acid ether compound. Carrying out sulfonation reaction for 0.5h at the temperature of 30 ℃ to obtain shikimic acid sulfonated product.

Example 3

This example provides a method for preparing a shikimic acid sulfonate, which is as follows. Uniformly mixing the shikimic acid ether compound and the organic solvent. Wherein the addition amount of shikimic acid ether compound is 1 eq. The organic solvent is trichloromethane, and the addition amount of the organic solvent is 10 times of the total addition amount of the shikimic acid ether compound and the methylsulfonyl chloride. After mixing well, methanesulfonyl chloride is added. The amount of methanesulfonyl chloride added was 1.1 eq. Further adding anion exchange resin as an acid-binding agent. The addition amount of the anion exchange resin is 15 times of that of the shikimic acid ether compound. Carrying out sulfonation reaction for 1.0h at the temperature of 0 ℃ to obtain shikimic acid sulfonated product.

Example 4

This example provides a method for preparing a shikimic acid sulfonate, which is as follows. Uniformly mixing the shikimic acid ether compound and the organic solvent. Wherein the addition amount of shikimic acid ether compound is 1 eq. The organic solvent is a mixture of ethyl acetate, dichloromethane and trichloromethane, and the addition amount of the organic solvent is 10 times of the total addition amount of the shikimic acid ether compound and the methylsulfonyl chloride. After mixing well, methanesulfonyl chloride is added. The amount of methanesulfonyl chloride added was 1.1 eq. Further adding anion exchange resin as an acid-binding agent. The addition amount of the anion exchange resin is 10 times of that of the shikimic acid ether compound. Carrying out sulfonation reaction for 1.5h at the temperature of 5 ℃ to obtain shikimic acid sulfonated product.

In the present invention, the terms "first", "second", and "third" are used for descriptive purposes only and are not to be construed as indicating or implying relative importance; the term "plurality" means two or more unless expressly limited otherwise. The terms "mounted," "connected," "fixed," and the like are to be construed broadly, and for example, "connected" may be a fixed connection, a removable connection, or an integral connection; "coupled" may be direct or indirect through an intermediary. The specific meanings of the above terms in the present invention can be understood by those skilled in the art according to specific situations.

In the description herein, the description of the terms "one embodiment," "some embodiments," "specific embodiments," etc., means that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.

The above is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and various modifications and changes will occur to those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.