CN114057950A

CN114057950A - Spherical polyurethane graft modified polyacrylate macroporous anion resin, preparation method thereof and application thereof in taurine production

Info

Publication number: CN114057950A
Application number: CN202010754001.0A
Authority: CN
Inventors: 孙华君; 谈敏; 江汝泳; 郭晨; 王星星; 彭洪波; 钱志强
Original assignee: Hubei Yuanda Life Science And Technology Co ltd
Current assignee: Hubei Yuanda Life Science And Technology Co ltd
Priority date: 2020-07-30
Filing date: 2020-07-30
Publication date: 2022-02-18
Anticipated expiration: 2040-07-30
Also published as: CN114057950B

Abstract

The invention provides a spherical polyurethane graft modified polyacrylate macroporous anion resin, a preparation method thereof and application thereof in adsorbing a compound with a sulfonic acid group, wherein the resin is selected from the spherical polyurethane graft modified polyacrylate macroporous anion resin. The resin can specifically and efficiently adsorb compounds with sulfonic acid groups, particularly taurine and salts thereof and isethionic acid and salts thereof, has good hydrophilicity, has the advantages of acid and alkali resistance, pollution resistance, strong thermal stability and the like, and has wide application prospect.

Description

Spherical polyurethane graft modified polyacrylate macroporous anion resin, preparation method thereof and application thereof in taurine production

Technical Field

The invention relates to the field of material chemical industry. Specifically, the invention relates to a spherical polyurethane graft modified polyacrylate macroporous anion resin, a preparation method thereof and application thereof in taurine production.

Background

The industrial synthesis of taurine is a main production mode of taurine at present, and the production process of taurine is accompanied by the generation of impurities, for example, the industrial preparation of taurine by using an ethylene oxide method cannot achieve 100% conversion in production, and is also accompanied by the generation of impurities, such as ethylene glycol, ethanolamine, unreacted intermediates (sodium hydroxyethyl sulfonate) and polymers thereof, so that the production rate of taurine is greatly reduced, and resources are wasted. Aiming at the impurities, currently, impurity removal modes such as activated carbon and ion exchange resin are mainly adopted, but the defects of single impurity removal mode, high cost, difficult subsequent activated carbon treatment and the like exist in the activated carbon impurity removal. The impurity removal mode of the ion exchange resin is to adsorb taurine on the surface of the resin, then desorb the taurine to obtain a pure taurine product, and the resin is regenerated after being processed to realize the recycling.

The macroporous resin applied to the compound separation technology of the sulfonic acid system is mainly polystyrene resin. Styrene ion exchange resin is synthesized mainly through suspension copolymerization of styrene and divinylbenzene in water phase to obtain copolymer bead and introducing ionizable group into the copolymer. Polystyrene as a molecular skeleton has strong hydrophobic property and a high cross-linked network structure, in the process of adsorbing a compound with a sulfonic acid group, a polar group on a polymer molecule is interfered by main chain resistance, the utilization rate of an effective active group is greatly reduced, meanwhile, the hydrophobic property of the polystyrene is opposite to the hydrophilic property of the compound with the sulfonic acid group, and the compound with the sulfonic acid group is difficult to adsorb onto resin from an aqueous solution. In addition, impurities can be adsorbed in the process of adsorbing the compound with the sulfonic acid group, so that the effect of specific selective adsorption cannot be achieved.

At present, acrylic resin is also used for separation in ion exchange resin separation technology. The macroporous anion resin prepared by acrylic acid is mostly weak-base anion resin, and the preparation process mainly utilizes the reaction of ester group of acrylate monomer and polyamino. Acrylic resin has many similarities with styrene macroporous resin, amino groups are directly linked with a molecular main chain, and in the process of ion exchange, the activity is interfered by the main chain, and the capacity of full exchange capacity is limited.

Therefore, the application of macroporous adsorption resins with sulfonic acid group compounds is still under study.

Disclosure of Invention

The present invention aims to solve at least to some extent at least one of the technical problems of the prior art. Therefore, the invention provides a novel spherical polyurethane graft modified polyacrylate macroporous anion resin, a preparation method thereof, application of the resin in adsorbing a compound with a sulfonic acid group, a method for producing taurine and a system for purifying the compound with the sulfonic acid group, the resin can specifically and efficiently adsorb the compound with the sulfonic acid group, particularly taurine and salt thereof and isethionic acid and salt thereof, and has the advantages of good hydrophilicity, strong exchange capacity, acid and alkali resistance, pollution resistance, strong thermal stability and the like, and the application prospect is wide.

In one aspect of the invention, a resin is provided. According to an embodiment of the invention, the resin is selected from spherical polyurethane graft modified polyacrylate macroporous anionic resins.

At present, polyurethane is mainly applied to foams, coatings, paints, adhesives and the like, and is rarely applied to macroporous resin, mainly because the antifouling capacity of the macroporous resin prepared directly from the polyurethane is poor, and the physical property of the macroporous resin is poor due to the direct synthesis of the macroporous resin, so that the long-term durable effect cannot be achieved.

According to the invention, polyurethane is grafted on acrylate, and the defects of polyurethane are overcome by utilizing the advantages of acid resistance, alkali resistance, pollution resistance, strong thermal stability and the like of the acrylate. Because of the amino group contained in the grafted polyurethane, the amino group can be dissociated into OH in water^-Ions of H dissociated from compounds having sulfonic acid groups⁺Displacement combination is carried out, so that the sulfonate ions are adsorbed on the resin, and the purpose of separation is realized. In addition, because the polyurethane contains ester groups and is hydrophilic groups, the macroporous resin can be endowed with better hydrophilicity, most of compounds with sulfonic acid groups have better water solubility, particularly taurine and salts thereof, and isethionic acid and salts thereof, the compounds with sulfonic acid groups and the macroporous resin form a uniform system, and the compounds with sulfonic acid groups are conveniently adsorbed in the macroporous resin. In addition, the spherical resin has the largest surface area under the condition of the same volume, which is beneficial to improving the exchange capacity. Therefore, the resin provided by the embodiment of the invention can specifically and efficiently adsorb compounds with sulfonic acid groups, especially taurine and salts thereof and isethionic acid and salts thereof, has good hydrophilicity, has the advantages of acid and alkali resistance, pollution resistance, strong thermal stability and the like, and has a wide application prospect.

According to an embodiment of the present invention, the above resin may further have the following additional technical features:

according to the embodiment of the invention, the particle size of the resin is 50-200 meshes.

According to an embodiment of the invention, the raw materials forming the polyurethane comprise: diisocyanate, polydiol, compound containing double bond and hydroxyl and amine compound.

According to an embodiment of the present invention, the diisocyanate includes at least one of toluene diisocyanate, 4' -diphenylmethane diisocyanate, isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, and dicyclohexylmethane diisocyanate.

According to an embodiment of the present invention, the polymerization degree of the polyglycol is selected from 200 to 800.

According to an embodiment of the present invention, the compound having a double bond and a hydroxyl group includes at least one of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, and pentaerythritol triacrylate.

According to an embodiment of the present invention, the amine compound includes at least one of 2-methyl-4-aminopentane, ethylenediamine, ethylamine, 3-diethylaminopentane, and diethanolamine.

According to an embodiment of the present invention, the monomer of the polyacrylate comprises at least one of methyl methacrylate, ethyl methacrylate, butyl acrylate, 1, 6-ethylene glycol dimethacrylate.

According to an embodiment of the invention, the molar ratio of the polyurethane to the acrylate is (0.3-1.5): 1.

in another aspect of the invention, the invention provides a method of making the aforementioned resin. According to an embodiment of the invention, the method comprises: and carrying out polymerization reaction on the acrylate monomer and the polyurethane prepolymer to obtain the spherical polyurethane graft modified polyacrylate macroporous anion resin. Therefore, the resin obtained by the method provided by the embodiment of the invention can specifically and efficiently adsorb compounds with sulfonic acid groups, especially taurine and salts thereof and isethionic acid and salts thereof, has good hydrophilicity, and has the advantages of acid and alkali resistance, pollution resistance, strong thermal stability and the like. And the method is simple and convenient to operate, low in cost, less in waste water discharge amount and few in byproducts, and is suitable for large-scale production.

According to the embodiment of the invention, the temperature of the polymerization reaction is 80-100 ℃ and the time is 6-12 hours.

According to an embodiment of the present invention, a method of preparing the polyurethane prepolymer includes: carrying out a first polymerization reaction on the diisocyanate and the polyglycol to obtain a first intermediate; carrying out a second polymerization reaction on the first intermediate and the compound with double bonds and hydroxyl groups to obtain a second intermediate; and carrying out a third polymerization reaction on the second intermediate and the amine compound to obtain the polyurethane prepolymer.

According to the embodiment of the invention, the first polymerization reaction temperature and the second polymerization reaction temperature are 50-90 ℃, and the third polymerization reaction temperature is-10 ℃.

According to the embodiment of the invention, the system of the polymerization reaction contains a cross-linking agent, a pore-forming agent, an initiator and a solvent.

According to an embodiment of the invention, the cross-linking agent comprises at least one of styrene, stilbene and polyvinyl alcohol.

According to an embodiment of the invention, the porogen comprises at least one of chlorobenzene and n-heptane.

According to an embodiment of the invention, the initiator comprises at least one of azobisisobutyronitrile and benzoyl peroxide.

According to an embodiment of the present invention, the solvent comprises at least one of toluene, ethyl acetate, butyl acetate, N, N-dimethylformamide, gasoline 200, and isobutanol.

In yet another aspect of the invention, the invention proposes the use of a spherical polyurethane graft-modified polyacrylate macroporous anionic resin for adsorbing compounds having sulfonic acid groups. As mentioned above, the spherical polyurethane graft modified polyacrylate macroporous anion resin can specifically and efficiently adsorb compounds with sulfonic acid groups, especially taurine and salts thereof and isethionic acid and salts thereof, has good hydrophilicity, and has the advantages of acid and alkali resistance, pollution resistance, strong thermal stability and the like, and has wide application prospect.

According to an embodiment of the present invention, said spherical polyurethane graft modified polyacrylate macroporous anion resin is selected from the spherical polyurethane graft modified polyacrylate macroporous anion resins defined in the resins previously described.

According to an embodiment of the present invention, the compound having a sulfonic acid group includes at least one of taurine, taurate, isethionic acid, ethanesulfonic acid, benzenesulfonic acid, 2-aminobenzenesulfonic acid, 4-dodecylbenzenesulfonic acid, 3-aminopropanesulfonic acid.

According to the embodiment of the invention, the spherical polyurethane graft-modified polyacrylate macroporous anion resin is used for adsorbing at least one of taurine, taurine salt, isethionic acid and isethionic acid salt in taurine production.

In yet another aspect of the invention, a method of producing taurine is provided. According to an embodiment of the invention, the method comprises: contacting a reaction liquid in the preparation process of taurine with a spherical polyurethane graft modified polyacrylate macroporous anion resin to ensure that at least one of taurine, taurine salt, isethionic acid and isethionic acid salt in the reaction liquid is adsorbed on the resin; and eluting the resin by using alkali liquor, and collecting eluent to obtain purified liquid containing at least one of taurine, taurine salt, isethionic acid and isethionic acid salt. Therefore, the method provided by the embodiment of the invention can effectively realize the purpose of purifying and removing impurities, and the obtained purified liquid is high in content of taurine and salts thereof and hydroxyethyl sulfonic acid and salts thereof and low in impurity content.

In yet another aspect of the present invention, the present invention provides a system for purifying a compound having a sulfonic acid group. According to an embodiment of the invention, the system comprises a chromatography column comprising: the body is internally provided with a cavity; the liquid inlet is arranged on the body and communicated with the cavity; the liquid outlet is arranged on the body and communicated with the cavity; a filling layer disposed in the cavity and between the liquid inlet and the liquid outlet, wherein the filling layer is formed of the resin. Therefore, the system provided by the embodiment of the invention can be used for adsorbing the compound with the sulfonic acid group in the packed layer, other impurities flow out, then the compound with the sulfonic acid group is desorbed by adding the eluent, and the collected eluent has high yield and good purity of the compound with the sulfonic acid group.

In yet another aspect of the invention, a system for producing taurine is provided. According to an embodiment of the present invention, the system comprises an anion resin adsorption device for separating at least one of taurine, taurine salt, isethionic acid and isethionic acid salt, wherein the anion resin adsorption device is provided with the resin as described above. Therefore, the system provided by the embodiment of the invention can effectively realize the purpose of separation and impurity removal, and the obtained separation liquid has high content of taurine and salts thereof, and high content of isethionic acid and salts thereof, and has less impurities.

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.

Drawings

The above and/or additional aspects and advantages of the present invention will become apparent and readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings of which:

FIG. 1 shows an infrared spectrum of polyurethane according to example 1 of the present invention;

FIG. 2 shows an infrared spectrum of polyurethane according to example 4 of the present invention;

FIG. 3 shows an infrared spectrum of polyurethane according to example 7 of the present invention;

FIG. 4 shows a nuclear magnetic spectrum of polyurethane according to example 1 of the present invention;

FIG. 5 shows a polyurethane NMR spectrum according to example 4 of the present invention;

FIG. 6 shows a polyurethane NMR spectrum according to example 7 of the present invention;

FIG. 7 shows a macroporous resin profile according to example 1 of the present invention;

FIG. 8 shows a macroporous resin profile according to example 4 of the present invention;

FIG. 9 shows a macroporous resin profile according to example 7 of the present invention;

FIG. 10 shows a schematic process flow diagram for taurine production;

FIG. 11 shows a schematic diagram of a system for purifying a compound having a sulfonic acid group.

Detailed Description

The following describes embodiments of the present invention in detail. The following examples are illustrative only and are not to be construed as limiting the invention. The examples, where specific techniques or conditions are not indicated, are to be construed according to the techniques or conditions described in the literature in the art or according to the product specifications. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products commercially available.

The invention provides a resin, a method for preparing the resin, application of a spherical polyurethane graft modified polyacrylate macroporous anion resin in adsorption of a compound with a sulfonic acid group and a method for producing taurine, which are respectively described in detail below.

Resin composition

According to the invention, polyurethane is grafted on acrylate, and the defects of polyurethane are overcome by utilizing the advantages of acid resistance, alkali resistance, pollution resistance, strong thermal stability and the like of the acrylate. Because of the amino group contained in the grafted polyurethane, the amino group can be dissociated into OH in water^-Ions of H dissociated from compounds having sulfonic acid groups⁺Displacement combination is carried out, so that the sulfonate ions are adsorbed on the resin, and the purpose of separation is realized. In addition, because the polyurethane contains ester groups and is hydrophilic groups, the macroporous resin can be endowed with better hydrophilicity, and most of compounds with sulfonic acid groups have better water solubility, particularly taurine and salts thereof, and isethionic acid and salts thereof, the compounds with sulfonic acid groups and the salts thereofThe macroporous resin forms a uniform system, so that the compound with sulfonic acid groups can be conveniently adsorbed in the macroporous resin. Therefore, the resin provided by the embodiment of the invention can specifically and efficiently adsorb compounds with sulfonic acid groups, especially taurine and salts thereof and isethionic acid and salts thereof, has good hydrophilicity, has the advantages of acid and alkali resistance, pollution resistance, strong thermal stability and the like, and has a wide application prospect.

According to an embodiment of the present invention, the polyurethane-forming raw materials include: diisocyanate, polydiol, compound containing double bond and hydroxyl and amine compound.

NCO in diisocyanate can be condensed with OH in polyglycol to obtain a compound (first intermediate) with a long chain structure introduced by the polyglycol. In the resin structure, the acrylate is used as a main chain, the polyurethane is used as a side chain, and the side chain is provided with a long-chain structure, so that the side chain can be less interfered by a main chain in a solvent and can freely move in the solvent, amino in the side chain structure can be more freely and flexibly and fully contacted with a target object (adsorbate), the effective total exchange capacity of the resin is improved, and the adsorption efficiency is improved. The isocyanate having two NCO groups is selected mainly for the purpose of providing NCO groups at both ends of the first intermediate, which facilitates subsequent reaction with hydroxyl groups of the compound having double bonds and hydroxyl groups, respectively, and amino groups of the amine compound. If the NCO number is too large, the system is liable to be excessively crosslinked to produce a gel. In addition, the polyglycol is similar to the ethyl structure on the taurine molecule, and based on the principle of similarity and intermiscibility, the polyglycol contributes to the formation of a homogeneous system of the resin and the taurine, and is convenient for the adsorption and separation of the taurine.

OH in a compound containing double bonds and hydroxyl can be subjected to condensation reaction with NCO in a first intermediate, double bond groups are introduced into the obtained compound (called a second intermediate for short), the double bonds can be opened and can participate in free radical polymerization of acrylate monomers, so that polyurethane is successfully grafted into a polyacrylate system, and a polyurethane-acrylate polymer is formed.

The amine compound is amino introduced into polyurethane, and the amino can be dissociated into OH in water^-Ions which readily dissociate from the sulfonic acid group compoundH of (A) to (B)⁺Displacement combination is carried out, so that the sulfonate ions are adsorbed on the resin, and the purpose of separation is realized.

According to an embodiment of the present invention, the diisocyanate includes at least one of toluene diisocyanate, 4' -diphenylmethane diisocyanate, isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, and dicyclohexylmethane diisocyanate. Therefore, two NCO groups can be provided, the reaction condition with the polyglycol is mild, and the target product is easy to obtain.

According to an embodiment of the present invention, the polymerization degree of the polyglycol is selected from 200 to 800. Therefore, the long side chain structure is introduced, so that the side chain can be less interfered by a main chain in a solvent and can freely move in the solvent, the amino in the side chain structure can be more freely and flexibly contacted with a target object (adsorbate), the effective total exchange capacity of the resin is improved, and the adsorption efficiency is improved. However, if the side chain is too long, the thermal stability of the macroporous resin is reduced, and the abrasion resistance is reduced.

According to an embodiment of the present invention, the compound having a double bond and a hydroxyl group includes at least one of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, and pentaerythritol triacrylate. The acrylate contains a hydroxyl group and a double bond structure, wherein the hydroxyl group reacts with NCO on polyurethane, a double bond group is introduced on the polyurethane, and the double bond provides a reactive group to generate polyurethane-acrylate resin.

According to an embodiment of the present invention, the amine compound includes at least one of 2-methyl-4-aminopentane, ethylenediamine, ethylamine, 3-diethylaminopentane, and diethanolamine. Thus, not only amino groups can be provided for adsorption purposes. Moreover, the structure of the resin is similar to that of ethyl on a taurine molecule, especially ethylenediamine, so that the resin and the taurine form a uniform system based on the similarity and intermiscibility principle, and the purpose of adsorption and separation of the taurine is conveniently realized. Further, the use of the amine compound can also improve the thermal stability of the resulting resin.

According to an embodiment of the present invention, the monomer of the polyacrylate comprises at least one of methyl methacrylate, ethyl methacrylate, butyl acrylate, 1, 6-ethylene glycol dimethacrylate. The acrylate monomer contains a hydroxyl side chain which is a hydrophilic group, so that the hydrophilicity of the macroporous resin is further improved, a uniform system is formed by the compound with the sulfonic group and the macroporous resin, and the compound with the sulfonic group is conveniently adsorbed in the macroporous resin. Moreover, the acrylate is short-chain micromolecule, the anti-fouling performance is good, and the thermal stability of the synthesized resin main chain structure is strong.

According to the embodiment of the invention, the molar ratio of the polyurethane to the acrylate is (0.3-1.5): 1. thus, the comprehensive performance of the macroporous resin can be improved. The acrylic ester monomer is used as a main chain structure, so that the thermal stability, the wear resistance, the acid resistance and the alkali resistance are good, if the long side chain structure proportion in the macroporous resin is too much in the synthesized macroporous resin, the crosslinking degree of the resin is reduced, the mechanical property of the macroporous resin is reduced, and the practical application capability of the macroporous resin is reduced.

According to the embodiment of the invention, the particle size of the resin is 50-200 meshes. Under the condition of the same volume, the spherical resin has the largest surface area and the largest contact area, thereby being beneficial to improving the exchange capacity. The resin particles with the particle size have better adsorption efficiency, antifouling performance and durability. If the particle size of the spherical resin particles is too large, the voids are too large when the spherical resin particles are packed in a column, and the solution of the dissolved adsorbate may flow out directly without coming into contact with the resin balls, resulting in a decrease in adsorption efficiency. If the particle size of the spherical resin particles is too small, the spherical resin particles are too dense when filled into a column, so that the anti-fouling capability of the resin is reduced, and the durability is influenced.

Method for preparing resin

In another aspect of the invention, the invention provides a method of making the aforementioned resin. According to an embodiment of the invention, the method comprises: and carrying out polymerization reaction on the acrylate monomer and the polyurethane prepolymer to obtain the spherical polyurethane graft modified polyacrylate macroporous anion resin.

At present, styrene series macroporous resin is mainly prepared by polymerizing styrene to prepare styrene microspheres, and then synthesizing resin through chloromethylation and amination modification. The method has the advantages of complex operation, multi-step reaction, more byproducts, more solvents for purification and increased wastewater discharge. According to the method provided by the embodiment of the invention, the acrylic ester monomer and the polyurethane prepolymer are subjected to suspension polymerization reaction, so that the amino-carrying macroporous anion resin can be directly synthesized, the resin is not required to be modified subsequently, the experimental steps are simplified, the yield is improved, the generation of byproducts is reduced, and the solvent removal step and the generation of wastewater are reduced. Therefore, the resin obtained by the method provided by the embodiment of the invention can specifically and efficiently adsorb compounds with sulfonic acid groups, especially taurine and salts thereof and isethionic acid and salts thereof, has good hydrophilicity, and has the advantages of acid and alkali resistance, pollution resistance, strong thermal stability and the like. And the method is simple and convenient to operate, low in cost, less in waste water discharge amount and few in byproducts, and is suitable for large-scale production.

For convenience of understanding, a reaction process for producing polyurethane graft-modified polyacrylate by polymerization reaction of methyl methacrylate as an acrylate monomer and a polyurethane prepolymer is provided below, wherein Pu is an abbreviation of polyurethane prepolymer.

According to the embodiment of the invention, the temperature of the polymerization reaction is 80-100 ℃ and the time is 6-12 hours. Therefore, the acrylic ester monomer and the polyurethane prepolymer are subjected to polymerization reaction, and the obtained macroporous resin has high yield and few byproducts.

According to an embodiment of the present invention, a method of preparing a polyurethane prepolymer includes: carrying out a first polymerization reaction on diisocyanate and polydihydric alcohol to obtain a first intermediate; carrying out a second polymerization reaction on the first intermediate and a compound with double bonds and hydroxyl groups to obtain a second intermediate; and carrying out a third polymerization reaction on the second intermediate and an amine compound to obtain a polyurethane prepolymer.

In the first polymerization reaction, two OH groups in the polyglycol are respectively subjected to polycondensation reaction with one NCO in one diisocyanate to obtain twoA first intermediate with isocyanates connected by a long chain structure. In the second polymerization reaction, one NCO in the first intermediate and a hydroxyl in the compound with double bonds and hydroxyl are subjected to condensation reaction to obtain a second intermediate with double bonds. In the third polymerization reaction, NCO in the second intermediate reacts with amine compounds so as to introduce amino in the amine compounds, and polyurethane prepolymer with amino is obtained. For convenience of understanding, a specific process for synthesizing a polyurethane prepolymer, wherein R-R is abbreviated as long chain (-CH)₂-CH₂-) n structure.

According to the embodiment of the invention, the first polymerization reaction temperature and the second polymerization reaction temperature are 50-90 ℃, and the third polymerization reaction temperature is-10 ℃. Therefore, the yield of the target product is high, and the purity is good.

According to the embodiment of the invention, the system of the polymerization reaction contains a cross-linking agent, a pore-forming agent, an initiator and a solvent. The cross-linking agent directly participates in the free radical polymerization reaction of the monomer, and the cross-linking degree of the macroporous resin is improved. The addition of the pore-foaming agent is beneficial to forming a porous structure, increases the contact specific surface area of the resin and a target object, and improves the adsorption efficiency. The addition of the initiator initiates the free radical polymerization of the polymerizing monomers. The addition of the solvent provides a polymerization monomer reaction site.

According to an embodiment of the invention, the cross-linking agent comprises at least one of styrene, stilbene and polyvinyl alcohol. The cross-linking agent directly participates in the free radical polymerization reaction of the monomer, and the cross-linking degree of the macroporous resin is improved.

According to an embodiment of the present invention, the porogen comprises at least one of chlorobenzene and n-heptane. Thus, a porous structure is formed on the obtained resin, the contact specific surface area of the resin and the target is increased, and the adsorption efficiency is improved.

According to an embodiment of the invention, the initiator comprises at least one of azobisisobutyronitrile and benzoyl peroxide. The addition of the above initiator can initiate radical polymerization of the polymerizable monomers.

According to an embodiment of the present invention, the solvent comprises at least one of toluene, ethyl acetate, butyl acetate, N, N-dimethylformamide, gasoline 200, and isobutanol. The reactants may be dissolved in the above-mentioned solvent to provide a polymerization reaction site.

It will be appreciated by those skilled in the art that the features and advantages previously described for the resin apply equally to the method of preparing the resin and will not be described in detail here.

Use of

According to an embodiment of the present invention, the spherical polyurethane graft-modified polyacrylate macroporous anion resin is selected from the spherical polyurethane graft-modified polyacrylate macroporous anion resins defined in the resins previously described.

According to an embodiment of the present invention, the compound having a sulfonic acid group includes at least one of taurine, taurate, isethionic acid, ethanesulfonic acid, benzenesulfonic acid, 2-aminobenzenesulfonic acid, 4-dodecylbenzenesulfonic acid, 3-aminopropanesulfonic acid. The resin according to the embodiment of the invention has good adsorption and desorption effects on the compound with the sulfonic acid group.

According to the embodiment of the invention, the spherical polyurethane graft modified polyacrylate macroporous anion resin is used for adsorbing taurine, taurine salt, isethionic acid and isethionic acid salt in taurine production. The spherical polyurethane graft modified polyacrylate macroporous anion resin can adsorb taurine, taurine salt, isethionic acid and isethionic acid salt from reaction liquid in the preparation process of synthetic taurine to remove impurities, and can also adsorb taurine, taurine salt, isethionic acid and isethionic acid salt from waste liquid to avoid loss and improve yield.

It will be appreciated by those skilled in the art that the features and advantages previously described for the resin apply equally to this application and will not be described in further detail herein.

Method for producing taurine

In yet another aspect of the invention, a method of producing taurine is provided. According to an embodiment of the invention, the method comprises: contacting a reaction liquid in the preparation process of taurine with a spherical polyurethane graft modified polyacrylate macroporous anion resin to ensure that at least one of taurine, taurine salt, isethionic acid and isethionic acid salt in the reaction liquid is adsorbed on the resin; and eluting the resin by using alkali liquor, and collecting eluent to obtain purified liquid containing at least one of taurine, taurine salt, isethionic acid and isethionic acid salt.

The reaction liquid in the preparation process of taurine is contacted with resin, so that at least one of taurine, taurine salt, isethionic acid and isethionic acid salt in the reaction liquid is adsorbed on the resin, and subsequent desorption (elution by alkali liquor) is carried out, so that at least one of taurine, taurine salt, isethionic acid and isethionic acid salt is collected, and the purification purpose is achieved. The contact mode is not strictly limited, the resin can be soaked in the reaction liquid, or the resin can be made into a resin column, so that the reaction liquid flows through the resin column, and both the reaction liquid and the resin column can achieve the adsorption purpose. FIG. 10 shows a general taurine production process, which can separate and purify taurine, taurine salts, isethionic acid and isethionic acid salts by using spherical polyurethane graft-modified polyacrylate macroporous anion resin at one or more of the several "resin removal" positions shown in the figure. Therefore, the method provided by the embodiment of the invention can effectively realize the purpose of purifying and removing impurities, and the obtained purified liquid is high in content of taurine and salts thereof and hydroxyethyl sulfonic acid and salts thereof and low in impurity content.

It will be appreciated by those skilled in the art that the features and advantages described above for the resin apply equally to the method for producing taurine and will not be described in detail here.

System for purifying compounds having sulfonic acid groups

In yet another aspect of the invention, the invention features a system for purifying a compound having a sulfonic acid group. According to an embodiment of the invention, referring to fig. 11, the system comprises a chromatography column comprising: a body 100, a cavity is formed in the body 100; a liquid inlet 200, wherein the liquid inlet 200 is arranged on the body 100 and communicated with the cavity; a liquid outlet 300, the liquid outlet 300 being disposed on the body 100 and communicating with the cavity; and the filling layer 400 is arranged in the cavity and is positioned between the liquid inlet 200 and the liquid outlet 300, wherein the filling layer is added with the resin. Therefore, the system provided by the embodiment of the invention can be used for adsorbing the compound with the sulfonic acid group in the packed layer, other impurities flow out, then the compound with the sulfonic acid group is desorbed by adding the eluent, and the collected eluent has high yield and good purity of the compound with the sulfonic acid group.

It should be noted that the system of the present invention may further comprise other apparatuses or components commonly used in chromatography, such as pumps, connecting pipes, valves, etc.

It will be appreciated by those skilled in the art that the features and advantages previously described for resins apply equally to the system for purifying compounds having sulfonic acid groups and will not be described in further detail herein.

System for preparing taurine

In yet another aspect of the invention, a system for producing taurine is provided. According to an embodiment of the invention, the system comprises an anion resin adsorption device for separating at least one of taurine, taurine salt, isethionic acid and isethionic acid salt, wherein the anion resin adsorption device is internally provided with the resin as described above. Therefore, the system provided by the embodiment of the invention can effectively realize the purpose of separation and impurity removal, and the obtained separation liquid has high content of taurine and salts thereof, and high content of isethionic acid and salts thereof, and has less impurities.

It will be understood by those skilled in the art that the features and advantages described above for the resin are equally applicable to the system for preparing taurine and will not be described in detail herein.

The scheme of the invention will be explained with reference to the examples. It will be appreciated by those skilled in the art that the following examples are illustrative of the invention only and should not be taken as limiting the scope of the invention. The examples, where specific techniques or conditions are not indicated, are to be construed according to the techniques or conditions described in the literature in the art or according to the product specifications. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products commercially available.

Example 1

Preparing a polyurethane prepolymer: 0.02mol of isophorone diisocyanate (IPDI), 0.01mol of polyethylene glycol 400 and 6ml of acetone are put into a three-neck flask provided with a condenser tube and a stirring rod, a few drops of DBTDL are dripped into the three-neck flask, the temperature is raised to 50 ℃, the heat preservation reaction is carried out for 3 hours, after the NCO is measured to the theoretical value by a di-n-butylamine method, 0.01mol of hydroxyethyl methacrylate (HEMA) is added and diluted by 2ml of acetone, the three-neck flask is cooled to the room temperature, 0.01mol of 2-methyl-4-aminopentane is added at the temperature of minus 10 ℃, the continuous reaction is carried out for 3 hours, and the Fourier infrared spectrum is adopted to detect 2270cm^-1If the peak appears, the reaction is complete if no absorption peak appears, the reaction can be stopped, the temperature is reduced, a little solvent is removed by rotary evaporation, and the preparation of the polyurethane carrying double bonds is finished.

Preparing macroporous resin: taking 200ml of deionized water, stirring in a four-neck flask provided with a stirrer, a condenser tube and a dropping funnel, putting a reaction vessel into an oil bath pot, heating to 65 ℃, and adding 8g of gelatin which is swelled in advance; and after the gelatin is completely dissolved, adding 5g of polyvinyl alcohol, uniformly mixing, adding 5g of sodium chloride, and preparing an aqueous phase solution. Under the room temperature environment, 0.01mol of divinylbenzene, 0.01mol of n-heptane, isobutanol, 0.01mol of methacrylate monomer methyl methacrylate, 0.005mol of polyurethane prepolymer and 0.1g of azobisisobutyronitrile are put into a conical flask, stirred on a magnetic stirrer to uniformly mix the components, and an oil phase solution is prepared. Dropwise adding the prepared oil phase into a four-neck flask filled with a water phase through a dropping funnel, and raising the reaction temperature to 70 ℃; keeping the temperature until the dispersed oil globules are qualitative, heating the reaction temperature to 80 ℃, keeping the temperature for reaction for 15h, and cooling to obtain the product. And filtering out beads in the product, washing with a large amount of deionized water, removing the evaporable pore-forming agent by a steam distillation method, drying, screening, alternately treating for 3-5 times with 1N NaOH and 1N HCl, and washing with water to be neutral to obtain the product, namely the resin BPU-1. The reaction scheme is as follows.

Example 2

Preparing a polyurethane prepolymer: 0.02mol of toluene diisocyanate, 0.01mol of polyethylene glycol 400 and 6ml of acetone are put into a three-neck flask provided with a condensing tube and a stirring rod, a few drops of DBTDL are dripped in, the temperature is raised to 60 ℃, the heat preservation reaction is carried out for 2h, after the NCO is measured to the theoretical value by a di-n-butylamine method, 0.01mol of HEMA is added and diluted by 2ml of acetone, the three-neck flask is cooled to the room temperature, 0.01mol of 2-methyl-4-aminopentane is added at the temperature of 0 ℃, the continuous reaction is carried out for 1.5 h, Fourier infrared spectroscopy is adopted to detect whether a peak is generated at 2270cm-1, the reaction is complete if no absorption peak is generated, the reaction can be stopped, the temperature is reduced, a little solvent is removed by rotary evaporation, and the preparation of polyurethane carrying double bonds is finished.

Preparing macroporous resin: taking 200g of deionized water, stirring in a four-neck flask provided with a stirrer, a condenser tube and a dropping funnel, putting a reaction vessel into an oil bath pot, heating to 65 ℃, and adding 8g of gelatin which is swelled in advance; and after the gelatin is completely dissolved, adding 5g of polyvinyl alcohol, uniformly mixing, adding 5g of sodium chloride, and preparing an aqueous phase solution. In a room temperature environment, 0.01mol of divinylbenzene, 0.01mol of n-heptane, isobutanol, 0.01mol of butyl acrylate, 0.01mol of polyurethane prepolymer and 0.1g of azobisisobutyronitrile are put into a conical flask, stirred on a magnetic stirrer, stirred to uniformly mix the components, and an oil phase solution is prepared. Dropwise adding the prepared oil phase into a four-neck flask filled with a water phase through a dropping funnel, and raising the reaction temperature to 70 ℃; keeping the temperature until the dispersed oil globules are qualitative, heating the reaction temperature to 80 ℃, keeping the temperature for reaction for 15h, and cooling to obtain the product. And filtering out beads in the product, washing with a large amount of deionized water, removing the evaporable pore-forming agent by a steam distillation method, drying, screening, alternately treating for 3-5 times with 1N NaOH and 1N HCl, and washing with water to be neutral to obtain the product, namely the resin BPU-2.

Example 3

Preparing a polyurethane prepolymer: 0.02mol of 4,4' -diphenylmethane diisocyanate, 0.01mol of polyethylene glycol 400 and 6ml of acetone are put into a three-neck flask provided with a condensing tube and a stirring rod, a few drops of DBTDL are dripped into the three-neck flask, the temperature is raised to 80 ℃, the heat preservation reaction is carried out for 1h, after the NCO is measured to reach the theoretical value by a di-n-butylamine method, 0.01mol of HEMA is added and diluted by 2ml of acetone, the three-neck flask is cooled to the room temperature, 0.01mol of 2-methyl-4-aminopentane is added at the temperature of 5 ℃, the continuous reaction is carried out for 1h, Fourier infrared spectrum is adopted to detect whether a peak appears at 2270cm & lt-1 & gt, the reaction is complete when no absorption peak appears, the reaction can be stopped, the temperature is reduced, a little solvent is removed by rotary evaporation, and the preparation of polyurethane carrying double bonds is finished.

Preparing macroporous resin: stirring 200g of deionized water in a four-neck flask provided with a stirrer, a condenser tube and a dropping funnel, putting a reaction vessel into an oil bath pot, heating to 65 ℃, and adding 8g of gelatin which is swelled in advance; and after the gelatin is completely dissolved, adding 5g of polyvinyl alcohol, uniformly mixing, adding 5g of sodium chloride, and preparing an aqueous phase solution. Under the room temperature environment, 0.01mol of divinylbenzene, 0.01mol of n-heptane, isobutanol, 0.01mol of 1, 6-glycol dimethacrylate, 0.015mol of polyurethane prepolymer and 0.1g of azobisisobutyronitrile are put into a conical flask, stirred on a magnetic stirrer, stirred to uniformly mix the components, and an oil phase solution is prepared. Dropwise adding the prepared oil phase into a four-neck flask filled with a water phase through a dropping funnel, and raising the reaction temperature to 70 ℃; keeping the temperature until the dispersed oil globules are qualitative, heating the reaction temperature to 80 ℃, keeping the temperature for reaction for 15h, and cooling to obtain the product. And filtering out beads in the product, washing with a large amount of deionized water, removing the evaporable pore-forming agent by a steam distillation method, drying, screening, alternately treating for 3-5 times with 1N NaOH and 1N HCl, and washing with water to be neutral to obtain the product, namely the resin BPU-3.

Example 4

Preparing a polyurethane prepolymer: 0.02mol of IPDI, 0.01mol of polyethylene glycol 600 and 6ml of acetone are taken to be put into a three-neck flask provided with a condensing tube and a stirring rod, a few drops of DBTDL are dripped in, the temperature is raised to 60 ℃, the heat preservation reaction is carried out for 2h, after the NCO is measured to reach the theoretical value by a di-n-butylamine method, 0.01mol of HEMA is added and diluted by 2ml of acetone, the three-neck flask is cooled to the room temperature, 0.01mol of ethylenediamine is added at the temperature of minus 5 ℃, the reaction is continuously carried out for 2h, Fourier infrared spectrum is adopted to detect whether a peak appears at 2270cm < -1 >, the reaction is complete if no absorption peak appears, the reaction can be stopped, the temperature is reduced, a little solvent is removed by rotary evaporation, and the preparation of the polyurethane carrying double bonds is finished.

Preparing macroporous resin: taking 200g of deionized water, stirring in a four-neck flask provided with a stirrer, a condenser tube and a dropping funnel, putting a reaction vessel into an oil bath pot, heating to 50 ℃, and adding 8g of gelatin which is swelled in advance; and after the gelatin is completely dissolved, adding 5g of polyvinyl alcohol, uniformly mixing, adding 5g of sodium chloride, and preparing an aqueous phase solution. In a room temperature environment, 0.01mol of divinylbenzene, 0.01mol of n-heptane, isobutanol, 0.01mol of methyl methacrylate, 0.005mol of polyurethane prepolymer and 0.1g of azobisisobutyronitrile are put into a conical flask, stirred on a magnetic stirrer to uniformly mix the components, and an oil phase solution is prepared. Dropwise adding the prepared oil phase into a four-neck flask filled with a water phase through a dropping funnel, and raising the reaction temperature to 80 ℃; keeping the temperature until the dispersed oil globules are qualitative, heating the reaction temperature to 90 ℃, keeping the temperature for reaction for 10 hours, and cooling to obtain the product. And filtering out beads in the product, washing with a large amount of deionized water, removing the evaporable pore-forming agent by a steam distillation method, drying, screening, alternately treating for 3-5 times with 1N NaOH and 1N HCl, and washing with water to be neutral to obtain the product, namely the resin BPU-4.

Example 5

Preparing a polyurethane prepolymer: 0.02mol of toluene diisocyanate, 0.01mol of polyethylene glycol 600 and 6ml of acetone are put into a three-neck flask provided with a condensing tube and a stirring rod, a few drops of DBTDL are dripped in, the temperature is raised to 60 ℃, the heat preservation reaction is carried out for 2h, after the NCO is measured to the theoretical value by a di-n-butylamine method, 0.01HEMA is added and diluted by 2ml of acetone, the three-neck flask is cooled to the room temperature, 0.01mol of ethylenediamine is added at the temperature of 0 ℃, the reaction is continuously carried out for 1.5 h, Fourier infrared spectrum is adopted to detect whether a peak appears at 2270cm < -1 >, the reaction is complete if no absorption peak appears, the reaction can be stopped, the temperature is reduced, a little solvent is removed by rotary evaporation, and the preparation of the polyurethane carrying double bonds is finished.

Preparing macroporous resin: taking 200g of deionized water, putting the deionized water into a four-neck flask provided with a stirrer, a condenser pipe and a dropping funnel, starting stirring at the rotating speed of 500r/min, putting a reaction vessel into an oil bath pot, heating the reaction vessel to 65 ℃, and adding 8g of gelatin which is swelled in advance; and after the gelatin is completely dissolved, adding 5g of polyvinyl alcohol, uniformly mixing, adding 5g of sodium chloride, and preparing an aqueous phase solution. In a room temperature environment, 0.01mol of divinylbenzene, 0.01mol of n-heptane, isobutanol, 0.01mol of butyl acrylate, 0.01mol of polyurethane prepolymer and 0.1g of azobisisobutyronitrile are put into a conical flask, stirred on a magnetic stirrer, stirred to uniformly mix the components, and an oil phase solution is prepared. Dropwise adding the prepared oil phase into a four-neck flask filled with a water phase through a dropping funnel, and raising the reaction temperature to 80 ℃; keeping the temperature until the dispersed oil globules are qualitative, heating the reaction temperature to 90 ℃, keeping the temperature for reaction for 10 hours, and cooling to obtain the product. And filtering out beads in the product, washing with a large amount of deionized water, removing the evaporable pore-forming agent by a steam distillation method, drying, screening, alternately treating for 3-5 times with 1N NaOH and 1N HCl, and washing with water to be neutral to obtain the product, namely the resin BPU-5.

Example 6

Preparing a polyurethane prepolymer: 0.02mol of 4,4' -diphenylmethane diisocyanate, 0.01mol of polyethylene glycol 600 and 6ml of acetone are put into a three-neck flask provided with a condensing tube and a stirring rod, a few drops of DBTDL are dripped into the three-neck flask, the temperature is raised to 60 ℃, the heat preservation reaction is carried out for 2 hours, after the NCO is measured to reach a theoretical value by a di-n-butylamine method, 0.01mol of HEMA is added and diluted by 2ml of acetone to reach the theoretical value, the three-neck flask is cooled to the room temperature, 0.01mol of ethylenediamine is added at the temperature of 5 ℃, the reaction is continuously carried out for 1 hour, Fourier infrared spectroscopy is adopted to detect whether a peak is generated at 2270cm & lt-1 & gt, the reaction is complete when an absorption peak is not generated, the reaction can be stopped, the temperature is reduced, a little solvent is removed by rotary evaporation, and the preparation of polyurethane carrying double bonds is finished.

Preparing macroporous resin: taking 200g of deionized water, stirring in a four-neck flask provided with a stirrer, a condenser tube and a dropping funnel, putting a reaction vessel into an oil bath pot, heating to 65 ℃, and adding 8g of gelatin which is swelled in advance; and after the gelatin is completely dissolved, adding 5g of polyvinyl alcohol, uniformly mixing, adding 5g of sodium chloride, and preparing an aqueous phase solution. Under the room temperature environment, 0.01mol of divinylbenzene, 0.01mol of n-heptane, isobutanol, 0.01mol of 1, 6-glycol dimethacrylate, 0.015mol of polyurethane prepolymer and 0.1g of azobisisobutyronitrile are put into a conical flask, stirred on a magnetic stirrer, stirred to uniformly mix the components, and an oil phase solution is prepared. Dropwise adding the prepared oil phase into a four-neck flask filled with a water phase through a dropping funnel, and raising the reaction temperature to 80 ℃; keeping the temperature until the dispersed oil globules are qualitative, heating the reaction temperature to 90 ℃, keeping the temperature for reaction for 10 hours, and cooling to obtain the product. And filtering out beads in the product, washing with a large amount of deionized water, removing the evaporable pore-forming agent by a steam distillation method, drying, screening, alternately treating for 3-5 times with 1N NaOH and 1N HCl, and washing with water to be neutral to obtain the product, namely the resin BPU-6.

Example 7

Preparing a polyurethane prepolymer: 0.02mol of IPDI, 0.01mol of polyethylene glycol 800 and 6ml of acetone are taken to be put into a three-neck flask provided with a condensing tube and a stirring rod, a few drops of DBTDL are dripped in, the temperature is raised to 60 ℃, the heat preservation reaction is carried out for 2h, after the NCO is measured to reach the theoretical value by a di-n-butylamine method, 0.01mol of HEMA is added and diluted by 2ml of acetone, the three-neck flask is cooled to the room temperature, 0.01mol of ethylamine is added at the temperature of 10 ℃, the reaction is continuously carried out for 0.5 h, whether a peak appears at 2270cm < -1 > is detected by adopting Fourier infrared spectroscopy, the reaction is complete if no absorption peak appears, the reaction can be stopped, the temperature is reduced, a little solvent is removed by rotary evaporation, and the preparation of polyurethane carrying double bonds is finished.

Preparing macroporous resin: taking 200g of deionized water, stirring in a four-neck flask provided with a stirrer, a condenser tube and a dropping funnel, putting a reaction vessel into an oil bath pot, heating to 65 ℃, and adding 8g of gelatin which is swelled in advance; and after the gelatin is completely dissolved, adding 5g of polyvinyl alcohol, uniformly mixing, adding 5g of sodium chloride, and preparing an aqueous phase solution. Under the room temperature environment, 0.01mol of divinylbenzene, 0.01mol of n-heptane, isobutanol, 0.01mol of methacrylate monomer, 0.005mol of polyurethane prepolymer and 0.1g of azobisisobutyronitrile are put into a conical flask and stirred on a magnetic stirrer to uniformly mix the components to prepare an oil phase solution. Dropwise adding the prepared oil phase into a four-neck flask filled with the water phase through a dropping funnel, and raising the reaction temperature to 90 ℃; keeping the temperature until the dispersed oil globules are qualitative, heating the reaction temperature to 100 ℃, keeping the temperature for reaction for 6 hours, and cooling to obtain the product. And filtering out beads in the product, washing with a large amount of deionized water, removing the evaporable pore-forming agent by a steam distillation method, drying, screening, alternately treating for 3-5 times with 1N NaOH and 1N HCl, and washing with water to be neutral to obtain the product, namely the resin BPU-7.

Example 8

Preparing a polyurethane prepolymer: 0.02mol of toluene diisocyanate, 0.01mol of polyethylene glycol 800 and 6ml of acetone are put into a three-neck flask provided with a condensing tube and a stirring rod, a few drops of DBTDL are dripped in, the temperature is raised to 60 ℃, the heat preservation reaction is carried out for 2h, after the NCO is measured to the theoretical value by a di-n-butylamine method, 0.01mol of HEMA is added and diluted by 2ml of acetone, the three-neck flask is cooled to the room temperature, 0.01mol of ethylamine is added at the temperature of minus 5 ℃, the reaction is continuously carried out for 3h, whether a peak appears at 2270cm < -1 > is detected by adopting Fourier infrared spectroscopy, the reaction is complete if no absorption peak appears, the reaction can be stopped, the temperature is reduced, a little solvent is removed by rotary evaporation, and the preparation of polyurethane carrying double bonds is finished.

Preparing macroporous resin: taking 200g of deionized water, stirring in a four-neck flask provided with a stirrer, a condenser tube and a dropping funnel, putting a reaction vessel into an oil bath pot, heating to 65 ℃, and adding 8g of gelatin which is swelled in advance; and after the gelatin is completely dissolved, adding 5g of polyvinyl alcohol, uniformly mixing, adding 5g of sodium chloride, and preparing an aqueous phase solution. In a room temperature environment, 0.01mol of divinylbenzene, 0.01mol of n-heptane, isobutanol, 0.01mol of methyl methacrylate, 0.01mol of polyurethane prepolymer and 0.1g of azobisisobutyronitrile are put into a conical flask, stirred on a magnetic stirrer to uniformly mix the components to prepare an oil phase solution. Dropwise adding the prepared oil phase into a four-neck flask filled with the water phase through a dropping funnel, and raising the reaction temperature to 90 ℃; keeping the temperature until the dispersed oil globules are qualitative, heating the reaction temperature to 100 ℃, keeping the temperature for reaction for 6 hours, and cooling to obtain the product. And filtering out beads in the product, washing with a large amount of deionized water, removing the evaporable pore-forming agent by a steam distillation method, drying, screening, alternately treating for 3-5 times with 1N NaOH and 1N HCl, and washing with water to be neutral to obtain the product, namely the resin BPU-8.

Example 9

Preparing a polyurethane prepolymer: 0.02mol of 4,4' -diphenylmethane diisocyanate, 0.01mol of polyethylene glycol 800 and 6ml of acetone are put into a three-neck flask provided with a condensing tube and a stirring rod, a few drops of DBTDL are dripped into the three-neck flask, the temperature is raised to 60 ℃, the heat preservation reaction is carried out for 2h, after the NCO is measured to a theoretical value by a di-n-butylamine method, 0.01mol of HEMA is added and diluted by 2ml of acetone, the three-neck flask is cooled to room temperature, 0.01mol of ethylamine is added at 0 ℃, the reaction is continuously carried out for 2h, Fourier transform is adopted to detect whether a peak appears at 2270cm < -1 >, the infrared spectrum peak does not appear, the reaction is complete, the reaction can be stopped, the temperature is reduced, a little solvent is removed by rotary evaporation, and the polyurethane carrying double bonds is prepared.

Preparing macroporous resin: taking 200g of deionized water, stirring in a four-neck flask provided with a stirrer, a condenser tube and a dropping funnel, putting a reaction vessel into an oil bath pot, heating to 65 ℃, and adding 8g of gelatin which is swelled in advance; and after the gelatin is completely dissolved, adding 5g of polyvinyl alcohol, uniformly mixing, adding 5g of sodium chloride, and preparing an aqueous phase solution. Under the room temperature environment, 0.01mol of divinylbenzene, 0.01mol of n-heptane, isobutanol, 0.01mol of methacrylate monomer, 0.015mol of polyurethane prepolymer and 0.1g of azodiisobutyronitrile are put into a conical flask, stirred on a magnetic stirrer, stirred to uniformly mix the components, and an oil phase solution is prepared. Dropwise adding the prepared oil phase into a four-neck flask filled with the water phase through a dropping funnel, and raising the reaction temperature to 90 ℃; keeping the temperature until the dispersed oil globules are qualitative, heating the reaction temperature to 100 ℃, keeping the temperature for reaction for 6 hours, and cooling to obtain the product. And filtering out beads in the product, washing with a large amount of deionized water, removing the evaporable pore-forming agent by a steam distillation method, drying, screening, alternately treating for 3-5 times with 1N NaOH and 1N HCl, and washing with water to be neutral to obtain the product, namely the resin BPU-9.

Example 10

Preparing a polyurethane prepolymer: 0.02mol of isophorone diisocyanate, 0.01mol of polyethylene glycol 400 and 6ml of acetone are put into a three-neck flask provided with a condensing tube and a stirring rod, a few drops of DBT DL are dripped into the three-neck flask, the temperature is raised to 50 ℃, the heat preservation reaction is carried out for 2 hours, after the NCO is measured to reach the theoretical value by a di-n-butylamine method, 0.01mol of HEMA is added and diluted by 2ml of acetone, the three-neck flask is cooled to the room temperature, 0.01mol of ethylamine is added at the temperature of minus 5 ℃, the reaction is continuously carried out for 3 hours, Fourier infrared spectrum is adopted to detect whether a peak appears at 2270cm < -1 >, the reaction is complete if no absorption peak appears, the reaction can be stopped, the temperature is reduced, a little solvent is removed by rotary evaporation, and the preparation of polyurethane carrying double bonds is finished.

Preparing macroporous resin: taking 200g of deionized water, stirring in a four-neck flask provided with a stirrer, a condenser tube and a dropping funnel, putting a reaction vessel into an oil bath pot, heating to 65 ℃, and adding 8g of gelatin which is swelled in advance; and after the gelatin is completely dissolved, adding 5g of polyvinyl alcohol, uniformly mixing, adding 5g of sodium chloride, and preparing an aqueous phase solution. Under the room temperature environment, 0.01mol of divinylbenzene, 0.01mol of n-heptane, isobutanol, 0.01mol of methacrylate monomer, 0.015mol of polyurethane prepolymer and 0.1g of azodiisobutyronitrile are put into a conical flask, stirred on a magnetic stirrer, stirred to uniformly mix the components, and an oil phase solution is prepared. Dropwise adding the prepared oil phase into a four-neck flask filled with the water phase through a dropping funnel, stirring at a constant speed, finishing dropwise adding within 2h, introducing nitrogen for protection, and raising the reaction temperature to 90 ℃; keeping the temperature until the dispersed oil globules are qualitative, heating the reaction temperature to 100 ℃, keeping the temperature for reaction for 4 hours, and cooling to obtain the product. And filtering out beads in the product, washing with a large amount of deionized water, removing the evaporable pore-forming agent by a steam distillation method, drying, screening, alternately treating for 3-5 times with 1N NaOH and 1N HCl, and washing with water to be neutral to obtain the product, namely the resin BPU-10.

Example 11

Preparing a polyurethane prepolymer: 0.02mol of isophorone diisocyanate, 0.01mol of polyethylene glycol 600 and 6ml of acetone are put into a three-neck flask provided with a condensing tube and a stirring rod, a few drops of DBTDL are dripped into the three-neck flask, the temperature is raised to 60 ℃, the heat preservation reaction is carried out for 2 hours, after the NCO is measured to reach the theoretical value by a di-n-butylamine method, 0.01mol of HEMA is added and diluted by 2ml of acetone, the three-neck flask is cooled to the room temperature, 0.01mol of hexamethylenediamine is added at the temperature of 0 ℃, the continuous reaction is carried out for 1 hour, Fourier infrared spectrum is adopted to detect whether a peak appears at 2270cm < -1 >, the reaction is complete if no absorption peak appears, the reaction can be stopped, the temperature is reduced, a little solvent is removed by rotary evaporation, and the preparation of polyurethane carrying double bonds is finished.

Preparing macroporous resin: taking 200g of deionized water, stirring in a four-neck flask provided with a stirrer, a condenser tube and a dropping funnel, putting a reaction vessel into an oil bath pot, heating to 65 ℃, and adding 8g of gelatin which is swelled in advance; and after the gelatin is completely dissolved, adding 5g of polyvinyl alcohol, uniformly mixing, adding 5g of sodium chloride, and preparing an aqueous phase solution. Under the room temperature environment, 0.01mol of divinylbenzene, 0.01mol of n-heptane, isobutanol, 0.01mol of methacrylate monomer, 0.015mol of polyurethane prepolymer and 0.1g of azodiisobutyronitrile are put into a conical flask, stirred on a magnetic stirrer, stirred to uniformly mix the components, and an oil phase solution is prepared. Dropwise adding the prepared oil phase into a four-neck flask filled with a water phase through a dropping funnel, and raising the reaction temperature to 60 ℃; keeping the temperature until the dispersed oil globules are qualitative, heating the reaction temperature to 70 ℃, keeping the temperature for reaction for 18h, and cooling to obtain the product. And filtering out beads in the product, washing with a large amount of deionized water, removing the evaporable pore-forming agent by a steam distillation method, drying, screening, alternately treating for 3-5 times with 1N NaOH and 1N HCl, and washing with water to be neutral to obtain the product, namely the resin BPU-11.

Example 12

Preparing a polyurethane prepolymer: 0.02mol of 4,4' -diphenylmethane diisocyanate, 0.01mol of polyethylene glycol 800 and 6ml of acetone are put into a three-neck flask provided with a condensing tube and a stirring rod, a few drops of DBTDL are dripped into the three-neck flask, the temperature is raised to 60 ℃, the heat preservation reaction is carried out for 2h, after the NCO is measured to reach the theoretical value by a di-n-butylamine method, 0.01mol of HEMA is added and diluted by 2ml of acetone, the three-neck flask is cooled to the room temperature, 0.01mol of hexamethylenediamine is added at the temperature of 0 ℃, the continuous reaction is carried out for 2h, Fourier transform is adopted to detect whether a peak is generated at 2270cm & lt-1 & gt, the reaction is complete without an infrared spectrum absorption peak, the reaction can be stopped, the temperature is reduced, a little solvent is removed by rotary evaporation, and the polyurethane carrying double bonds is prepared.

Preparing macroporous resin: putting 200g of deionized water into a four-neck flask provided with a stirrer, a condenser tube and a dropping funnel, starting stirring at the rotating speed of 900r/min, putting a reaction vessel into an oil bath pot, heating to 65 ℃, and adding 8g of gelatin which is swelled in advance; and after the gelatin is completely dissolved, adding 5g of polyvinyl alcohol, uniformly mixing, adding 5g of sodium chloride, and preparing an aqueous phase solution. Under the room temperature environment, 0.01mol of divinylbenzene, 0.01mol of n-heptane, isobutanol, 0.01mol of methacrylate monomer, 0.02mol of polyurethane prepolymer and 0.1g of azobisisobutyronitrile are put into a conical flask and stirred on a magnetic stirrer to uniformly mix the components to prepare an oil phase solution. Dropwise adding the prepared oil phase into a four-neck flask filled with the water phase through a dropping funnel, and raising the reaction temperature to 90 ℃; keeping the temperature until the dispersed oil globules are qualitative, heating the reaction temperature to 110 ℃, keeping the temperature for reaction for 4 hours, and cooling to obtain the product. And filtering out beads in the product, washing with a large amount of deionized water, removing the evaporable pore-forming agent by a steam distillation method, drying, screening, alternately treating for 3-5 times with 1N NaOH and 1N HCl, and washing with water to be neutral to obtain the product, namely the resin BPU-12.

Description of the invention

In the above examples 1 to 12, the molecular weight distribution of the spherical polyurethane graft modified polyacrylate macroporous anion resin is 30000 to 800000, and the mesh number is 50 to 200.

The reacted monomers in the above examples are only a part of the monomers in the claims, and the unreacted monomers involved therein have the same effects as described above.

Infrared spectroscopic analysis

The polyurethane prepolymers obtained in examples 1, 4 and 7 were subjected to infrared spectroscopic analysis, and the chromatograms are shown in FIGS. 1 to 3. From FIG. 1, it can be seen that the WPU spectrum is 2932cm^-1There is a broad and strong absorption peak, where (-CH) is included₃)，(-CH₂) Has a peak of stretching vibration absorption of 1497cm^-1At 1438cm^-1Respectively shows the bending vibration absorption peak; 3300cm^-1～3400cm^-1The strong single absorption peak appears around the position of the compound is secondary amino (-NH)_-) Upper bending vibration absorption peak, here it is illustrated that amino groups are introduced into the polyurethane molecular chain; the C-O stretching vibration peak appears in 1256cm^-1Here, the appearance of this peak indicates successful introduction of PEG-600 in the system; at 3072cm^-1And absorption peak at 1615cm^-1The absorption peaks appeared here are C-H stretching vibration peak and C ═ C stretching vibration peak, which are typical double bond characteristic peaks, and the peak situation indicates that HEMA is successfully introduced into the polyurethane chain; 2270cm on WPU^-1the-NCO characteristic peak appeared at the position disappears in a WPU-PG diagram, and the-NCO reaction is completely shown; 1086cm^-1And 873cm^-1The shown result is C-O-C asymmetric stretching vibration and symmetric stretching vibration absorption peaks, which all show that HEMA is successfully grafted to a polyurethane molecular chain; the peak position of the characteristic peak of C ═ O is obvious, and the peak intensity is large, 1723cm in the figure^-1Here, this characteristic peak appears, indicating that PWPU forms a carbamate group.

FIG. 2 shows a similar infrared absorption peak wavelength of the radicals in FIG. 1, except that the infrared absorption peak wavelength is 3500cm^-1Two broad absorption peaks appear here, this being a primary amino group (-NH)₂) Typical infrared absorption peaks show that ethylenediamine is successfully introduced into a polyurethane molecular chain, and amino groups are successfully modified into polyurethane.

FIG. 3 is similar to the infrared absorption peak of FIG. 1, and the peak is relatively consistent.

Nuclear magnetic analysis

The results of nuclear magnetic analysis of the polyurethane prepolymers obtained in examples 1, 4 and 7 are shown in FIGS. 4 to 6. FIG. 4 shows a hydrogen spectrum of PU (polyurethane prepolymer). From the figure, the peak (CH) of the methylene proton of the double bond in HEMA can be obtained₂C-) occurs at δ 5.1308ppm and δ 5.3403ppm, the proton front at δ 2.9193ppm is (CH)₂＝CH-CH₂-) proton peaks on carbon atoms ortho to the double bond, indicating successful introduction of HEMA into the polyurethane system; methylene proton peak (- -R- - -CH) attached to ester amino group₂-CH₂The chemical shift δ — R) was 3.672ppm, indicating the incorporation of PEG-600. The proton front at the position of delta-4.3621 ppm is the absorption peak of the proton of the adjacent carbon atom of the carbamate (O-H)₂C-…-CH₂-O), δ 2.8813ppm with a proton front (-NH-CH)₂-) proton fronts on adjacent carbon atoms of the amino polyurethane, indicating the formation of polyurethane; the proton front at 2.0938ppm is the amino-linked proton front, indicating that the polyurethane has amino groups attached. The position where delta is 1.3112ppm and the position where delta is 1.0721ppm has stronger (-CH)₂-CH₂-) and (-CH)₃) And the proton peak is the proton front on the saturated carbon atom on the polyurethane molecule.

FIG. 5 shows nuclear magnetic resonance proton front shift of ethylenediamine-modified polyurethane similar to that of FIG. 4, wherein the absorption peak at δ 3.9212ppm is (-NH-CH) on ethylenediamine₂-NH₂) The proton absorption peak of carbon atom, the stronger single peak appearing at 1.9981 is the proton absorption peak of the free amino group on the ethylenediamine, which indicates that the ethylenediamine is successfully introduced into the polyurethane molecular chain.

The proton absorption peak shift of fig. 6 is similar to that of fig. 4, where the difference is that δ -2.4691 ppm is the proton absorption peak on the (-CH3) carbon atom on ethylamine, the stronger single peak appearing at 2.0789 is the proton absorption peak on the (-NH-) nitrogen atom generated by connecting ethylamine with polyurethane, and surface ethylamine is successfully introduced into the polyurethane molecular chain.

Pore size analysis of macroporous resins

The macroporous resins obtained in examples 1 to 9 were subjected to pore size analysis, wherein the results of examples 1, 4 and 7 are shown in FIGS. 7 to 9, and the results of other examples are close to those of the other examples. The figure shows that the prepared spherical macroporous resin has uniform pore diameter mainly distributed between 50-100 nm, wherein partial transitional pores exist between 20-40 nm.

Example 13

Taurine static adsorption-desorption experiment: the polyurethane-acrylic acid macroporous resin prepared in the examples 1-9 (600 g) and the commercially available styrene series macroporous anion resins D201, D200, D201-717, AB-8, S-8, ADS-17 and D301600 g (D301600 g) are filled into a chromatographic column, and the resin is pretreated under the same conditions and activated for standby.

Static adsorption experiment: quantitatively weighing taurine, adding deionized water, slightly heating for dissolving, transferring into a volumetric flask, preparing taurine aqueous solution, and standing for later use. The wet resin is quantitatively weighed and the weighed resin is transferred into a conical flask with a constant temperature water bath. Accurately transferring the prepared taurine solution (or sample solution) by using a pipette, putting the taurine solution (or sample solution) into a conical flask filled with resin (the ratio of the resin to the solution is 1:5), adding a stirring rotor, starting the machine to uniformly stir for 20min, filtering the resin in the solution after the machine is shut down to achieve balance, quantitatively transferring clear liquid, and analyzing the concentration of taurine in the absorbed solution. And calculating the static adsorption amount of the taurine on various adsorption resins.

Static desorption experiment: washing the resin with saturated adsorption with deionized water, transferring into a conical flask, adding 4% NaOH and a stirring rotor in a constant-temperature water bath, filtering after 24h, measuring the concentration of the eluent, and calculating the desorption amount and the desorption rate of the resin.

The total exchange capacity of the macroporous resin is shown in table 1, and the neutral salt decomposition capacity and the total exchange capacity of the prepared resin BPU-1-9 are good and have good ion exchange capacity. The water content ratio is at a low level, indicating that it has a high crosslinking state and the resin has a high solvent resistance. The grinding ball rate is higher, and the prepared resin is proved to have stronger durability. Wherein if the polymerization temperature and time are not in the range of 70-95 ℃ and 6-12 hours (examples 10-13), the resulting resin has a low balling rate and cannot be used. Thus, the process conditions of examples 1 to 9 are optimal, and the obtained BPU-1 to 9 have the best performance.

TABLE 1

The static adsorption-desorption experimental data of the macroporous resin on taurine are shown in table 2, and it can be seen from table 2 that the prepared macroporous anion resin shows excellent adsorption-desorption performance when adsorbing pure taurine solution, only D201 and D201-717 of the commercially available macroporous anion resin show good adsorption capacity on pure taurine, however, the desorption performance of D201 is poor, the maximum purification rate of D201-717 resin is only 65.48%, loss of the taurine product is large in practical application, production is not facilitated, and the purification rate (adsorption rate x resolution rate) of the macroporous resin prepared by the invention on pure taurine is over 70% and far higher than that of the common commercially available resin, and the macroporous resin has good potential in practical production of taurine.

TABLE 2

Example 14

Taurine dynamic adsorption-desorption experiment in simulation production: 500ml of the resin completely pretreated in example 10 was packed in each case into a chromatography column.

The neutralized taurine simulated solution in taurine production: 0.1g of polyethylene glycol 200, 0.1g of polyethanolamine 200, 1g of ethylene glycol, 1g of ethanolamine, 3g of sodium isethionate and 90g of taurine are dissolved by deionized water to prepare 1L of mixed solution for later use.

Dynamic adsorption experiment: taking taurine simulation solution with the volume twice that of the resin, passing through a chromatographic column at room temperature, passing through the chromatographic column at room temperature, adjusting the rotating speed of a peristaltic pump, controlling the flow rate of the solution to be 2VB/h, washing with deionized water, stopping washing until the PH value of a washing solution to be measured is 5.5-6.5, and measuring the content of taurine and the content of impurities in the collected solution.

Dynamic desorption experiment: slowly flowing 4 times of resin volume through the resin by using 4% NaOH, adjusting the rotating speed of a peristaltic pump, controlling the flow rate of the solution to be 2.5VB/h, washing by using deionized water, stopping washing when the PH value of a washing solution to be measured is 9-10, and measuring the taurine content and the impurity content thereof in a collecting solution.

The data of the simulation experiment of the production-neutralized taurine solution are shown in tables 3 and 4. As can be seen from tables 3 and 4, when impurities which may appear in production are added, the adsorption-desorption rate of the macroporous resin prepared by the invention on taurine is not obviously reduced, the prepared macroporous resin has less adsorption quantity on the impurities, and has the performance of efficiently and specifically and selectively adsorbing taurine, so that the purpose of purifying the taurine in production is achieved. Wherein D201 and D201-717 which show better adsorption performance in the pure taurine do not have specific selective adsorption to the taurine, and a large amount of other impurities are adsorbed while the taurine is adsorbed, thereby achieving the purpose of purifying the taurine.

TABLE 3

TABLE 4

Example 15

The adsorption behavior of resins BPU-1, BPU-4, BPU-7 on other sulfonic acid type compounds was investigated:

the sulfonic acid type compound is selected from homotaurine, isethionic acid, ethylsulfonic acid, benzenesulfonic acid, 2-aminobenzenesulfonic acid, 4-dodecylbenzenesulfonic acid and 3-aminopropanesulfonic acid, 45g of each of which is metered by a 500ml volumetric flask to prepare a pure solution with the content of 8%. Numbers are homotaurine-SA 1, isethionic acid-SA 2, ethylsulfonic acid-SA 3, benzenesulfonic acid-SA 4, 2-aminobenzenesulfonic acid-SA 5, 4-dodecylbenzenesulfonic acid-SA 6 and 3-aminopropanesulfonic acid-SA 7 for standby.

Static adsorption experiment: quantitatively weighing wet resins BPU-1, BPU-4 and BPU-7, and respectively transferring the weighed resins into different conical flasks with constant-temperature water baths. Accurately transferring the prepared taurine solution (or sample solution) by a pipette, putting the solution into a conical flask filled with resin (the ratio of the resin to the solution is 1:5), adding a stirring rotor, starting the machine to uniformly stir for 20min, shutting down the machine, filtering the resin in the solution after the adsorption reaches the balance, quantitatively transferring clear liquid, and analyzing the concentration of each sulfonic acid group compound in the solution after the adsorption. The amount of static adsorption of the compound on the various adsorption resins was calculated.

The saturated adsorption and desorption rates of the resins BPU-1, BPU-4 and BPU-7 to other sulfonic acid group compounds are shown in tables 2 and 5, and the comparative data of the two tables show that the prepared resin has excellent adsorption and desorption performance to taurine and isethionic acid, and simultaneously has better adsorption and desorption performance to other sulfonic acid group-containing compounds, and the purity rate of the resin can show that the finally obtained product is about 60 percent.

TABLE 5

In the description herein, references to the description of the term "one embodiment," "some embodiments," "an example," "a specific example," or "some examples," etc., mean 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. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples. Furthermore, various embodiments or examples and features of different embodiments or examples described in this specification can be combined and combined by one skilled in the art without contradiction.

Although embodiments of the present invention have been shown and described above, it is understood that the above embodiments are exemplary and should not be construed as limiting the present invention, and that variations, modifications, substitutions and alterations can be made to the above embodiments by those of ordinary skill in the art within the scope of the present invention.

Claims

1. A resin, characterized in that the resin is selected from spherical polyurethane graft-modified polyacrylate macroporous anion resins.

2. The resin according to claim 1, wherein the particle size of the resin is 50 to 200 mesh.

3. The resin of claim 1, wherein the raw materials forming the polyurethane comprise:

diisocyanate, polydiol, compound containing double bond and hydroxyl and amine compound;

optionally, the diisocyanate comprises at least one of toluene diisocyanate, 4' -diphenylmethane diisocyanate, isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, and dicyclohexylmethane diisocyanate;

optionally, the polymerization degree of the polyglycol is selected from 200-800;

optionally, the compound having a double bond and a hydroxyl group includes at least one of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, and pentaerythritol triacrylate;

optionally, the amine compound comprises at least one of 2-methyl-4-aminopentane, ethylenediamine, ethylamine, 3-diethylaminopentane, and diethanolamine.

4. The resin of claim 1, wherein the monomers of the polyacrylate comprise at least one of methyl methacrylate, ethyl methacrylate, butyl acrylate, 1, 6-ethylene glycol dimethacrylate;

optionally, the molar ratio of the polyurethane to the acrylate is (0.3-1.5): 1.

5. a method for preparing the resin according to any one of claims 1 to 4, comprising:

and carrying out polymerization reaction on the acrylate monomer and the polyurethane prepolymer to obtain the spherical polyurethane graft modified polyacrylate macroporous anion resin.

6. The method according to claim 5, wherein the polymerization reaction is carried out at a temperature of 80 to 100 ℃ for 6 to 12 hours;

optionally, the method of preparing the polyurethane prepolymer comprises:

carrying out a first polymerization reaction on the diisocyanate and the polyglycol to obtain a first intermediate;

carrying out a second polymerization reaction on the first intermediate and the compound with double bonds and hydroxyl groups to obtain a second intermediate;

performing a third polymerization reaction on the second intermediate and the amine compound to obtain the polyurethane prepolymer;

optionally, the first polymerization reaction and the second polymerization reaction are carried out at the temperature of 50-90 ℃, and the third polymerization reaction is carried out at the temperature of-10 ℃.

7. The method according to claim 5, wherein the system of the polymerization reaction contains a cross-linking agent, a pore-forming agent, an initiator and a solvent;

optionally, the crosslinking agent comprises at least one of styrene, stilbene, and polyvinyl alcohol;

optionally, the porogen comprises at least one of chlorobenzene and n-heptane;

optionally, the initiator comprises at least one of azobisisobutyronitrile and benzoyl peroxide;

optionally, the solvent comprises at least one of toluene, ethyl acetate, butyl acetate, N, N-dimethylformamide, gasoline 200, and isobutanol.

8. Use of a spherical polyurethane graft-modified polyacrylate macroporous anion resin for adsorbing compounds having sulfonic acid groups.

9. The use according to claim 8, wherein the spherical polyurethane graft-modified polyacrylate macroporous anion resin is selected from the group consisting of the spherical polyurethane graft-modified polyacrylate macroporous anion resins in the resins according to any one of claims 1 to 4;

optionally, the compound having a sulfonic acid group includes at least one of taurine, taurate, isethionic acid, ethanesulfonic acid, benzenesulfonic acid, 2-aminobenzenesulfonic acid, 4-dodecylbenzenesulfonic acid, 3-aminopropanesulfonic acid;

optionally, the spherical polyurethane graft-modified polyacrylate macroporous anion resin is used for adsorbing at least one of taurine, taurine salt, isethionic acid and isethionic acid salt in taurine production.

10. A method of producing taurine comprising:

contacting a reaction liquid in the preparation process of taurine with a spherical polyurethane graft modified polyacrylate macroporous anion resin to ensure that at least one of taurine, taurine salt, isethionic acid and isethionic acid salt in the reaction liquid is adsorbed on the resin;

eluting the resin with alkali liquor, and collecting eluent to obtain purified liquid containing at least one of taurine, taurine salt, isethionic acid and isethionic acid salt;

optionally, the spherical polyurethane graft-modified polyacrylate macroporous anion resin is selected from the spherical polyurethane graft-modified polyacrylate macroporous anion resins defined in the resin of any one of claims 1 to 4.

11. A system for purifying a compound having a sulfonic acid group, comprising a chromatography column comprising:

the body is internally provided with a cavity;

the liquid inlet is arranged on the body and communicated with the cavity;

the liquid outlet is arranged on the body and communicated with the cavity;

a filling layer arranged in the cavity and positioned between the liquid inlet and the liquid outlet,

wherein the filling layer is added with the resin as described in any one of claims 1 to 4.

12. A system for preparing taurine, characterized in that the system comprises an anion resin adsorption device for separating at least one of taurine, taurine salt, isethionic acid and isethionic acid salt,

wherein the resin according to any one of claims 1 to 4 is provided in the anion resin adsorption device.