WO2022141229A1 - Procédé de préparation de sucralose, solution de produit brut et sucralose - Google Patents

Procédé de préparation de sucralose, solution de produit brut et sucralose Download PDF

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Publication number
WO2022141229A1
WO2022141229A1 PCT/CN2020/141531 CN2020141531W WO2022141229A1 WO 2022141229 A1 WO2022141229 A1 WO 2022141229A1 CN 2020141531 W CN2020141531 W CN 2020141531W WO 2022141229 A1 WO2022141229 A1 WO 2022141229A1
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sucralose
ethyl ester
reaction
distillation
solution
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PCT/CN2020/141531
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English (en)
Chinese (zh)
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张正颂
赵金刚
李正华
杨志健
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安徽金禾实业股份有限公司
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Priority to PCT/CN2020/141531 priority Critical patent/WO2022141229A1/fr
Priority to CN202080004019.7A priority patent/CN112771059A/zh
Publication of WO2022141229A1 publication Critical patent/WO2022141229A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Definitions

  • the invention belongs to the technical field of fine chemicals, and particularly relates to a preparation method of sucralose, a crude product solution and sucralose.
  • Sucralose belongs to a new generation of sweeteners, which has the advantages of high sweetness, no calories, good stability and high safety, and has a very broad market prospect. Regarding the synthesis process of sucralose, great progress has been made since the advent of sucralose.
  • the mainstream synthesis process is the single-group protection method: the 6-position hydroxyl group with the highest activity of sucrose is selectively protected, usually in the form of acetate, that is, to generate sucrose-6-ethyl ester, sucrose-6-ethyl ester
  • sucrose-6-ethyl ester The three hydroxyl groups at the 4, 1' and 6' positions of sucralose are selectively chlorinated to generate sucralose-6-ethyl ester, and the sucralose-6-ethyl ester is deacetylated to generate sucralose.
  • the existing technology basically adopts a catalytic amount of sodium methoxide (MeONa) as a catalyst, and alcoholysis is carried out in methanol (MeOH) to remove the acetyl group to generate sucralose, and by-product methyl acetate etc. .
  • MeONa/MeOH catalytic system has the advantages of mild conditions, rapid reaction and high yield, but it also has certain disadvantages. For example, MeONa is relatively expensive and cannot be recycled, which increases the production cost; the generated methyl acetate can not be used as a by-product.
  • the types of materials that need to be operated in the technological process are added.
  • sucralose-6-ethyl ester as the reaction raw material often contains a small amount of water
  • hydrolysis reaction as a side reaction, which competes with the main reaction of alcoholysis, which not only causes a large amount of waste of catalyst MeONa, but also generates sodium acetate.
  • the cationic resin is exchanged to generate acetic acid, and the acetic acid remains in the sucralose product, which makes the product have an obvious acidic odor, which seriously affects the product quality.
  • the present application is proposed in order to provide a preparation method of sucralose, its crude product solution and sucralose which overcome the above problems or at least partially solve the above problems.
  • a preparation method of sucralose comprising:
  • Dissolving step dissolving sucralose-6-ethyl ester in ethanol to form a sucralose-6-ethyl ester reaction solution;
  • Distillation step distilling the sucralose-6-ethyl ester reaction solution to remove moisture therein;
  • Catalysis step adding an alkaline catalyst to the sucralose-6-ethyl ester reaction solution obtained in the distillation step, and reacting under preset conditions, so that the sucralose-6-ethyl ester undergoes a deacylation reaction , forming a mixed solution of sucralose;
  • the step of removing impurities filtering the mixed solution of sucralose to obtain a crude product solution of sucralose.
  • a crude sucralose product solution is provided, which is prepared by the above-mentioned preparation method, wherein the by-product acetic acid content is less than or equal to 230 ppm.
  • a sucralose is provided, which is obtained by crystallizing and refining the above-mentioned sucralose crude product solution.
  • the beneficial effects of the present application are as follows: the present application adopts ethanol as a solvent, and the by-product ethyl acetate is a species originally used in the sucralose production process flow, and can be applied to the process, thereby reducing the number of The types of materials to be treated in the sucralose generation process significantly reduce the difficulty and cost of post-treatment; and the water in the reaction system can be removed by azeotropic distillation to avoid the occurrence of hydrolysis side reactions, which greatly reduces the The content of the by-product acetic acid improves the product quality of sucralose; and the catalyst in the present application can be recycled through simple treatment, thereby reducing the production cost of sucralose.
  • FIG. 1 shows a schematic flowchart of a method for preparing sucralose according to an embodiment of the present application.
  • MeONa/MeOH represents the coexistence of the two, specifically using MeONa as a catalyst and MeOH as a solvent
  • MeONa/MeOH represents the coexistence of the two, specifically using MeONa as a catalyst and MeOH as a solvent
  • MeONa/MeOH represents the coexistence of the two, specifically using MeONa as a catalyst and MeOH as a solvent
  • the MeONa/MeOH system is widely used.
  • As a catalyst there are many drawbacks, such as large catalyst consumption and difficult recovery; and the by-product methyl acetate increases the material types of the overall reaction system, and increases the difficulty and workload of post-processing.
  • MeONa can be replaced by many different types of bases, which can be strong bases, weak bases, organic bases or inorganic bases, etc., and also include bases
  • bases which can be strong bases, weak bases, organic bases or inorganic bases, etc., and also include bases
  • the deacetylation process can be smoothly catalyzed by bases in immobilized form such as anion resins.
  • the present application uses ethanol (EtOH) as a solvent, and cheaper and readily available bases as catalysts, such as sodium hydroxide (NaOH), potassium hydroxide (KOH), etc., to successfully realize sucralose-6-
  • EtOH ethanol
  • bases such as sodium hydroxide (NaOH), potassium hydroxide (KOH), etc.
  • the catalytic deacetylation process of ethyl ester makes up for many deficiencies of the MeONa/MeOH catalytic system.
  • the inventor also found that, because the sucralose-6-ethyl ester as the reaction raw material often contains a small amount of water, in the presence of MeONa, the hydrolysis of the sucralose-6-ethyl ester will be caused, and the hydrolysis reaction is used as a side reaction. , competes with the main reaction of alcoholysis, will consume a large amount of catalyst MeONa, and generate sodium acetate (AcONa), and sodium acetate is exchanged with acidic cation resin to generate acetic acid (HOAc). In the sucralose product, the product has an obvious acidic odor, which seriously affects the product quality. In view of the above problems, the present application adopts the means of distillation to remove the water in the reaction system by azeotroping of ethanol and water, so as to avoid the side reaction of hydrolysis to generate acetic acid.
  • Fig. 1 shows the schematic flow sheet of the preparation method of sucralose according to an embodiment of the present application, including:
  • Dissolving step S110 Dissolving sucralose-6-ethyl ester in ethanol to form a sucralose-6-ethyl ester reaction solution.
  • sucralose-6-acetate the chemical reaction process is shown in the reaction formula (1).
  • the 6-position hydroxyl group has the highest activity of sucrose.
  • sucrose and acetic anhydride are used for protection.
  • the esterification reaction produces sucrose-6-ethyl ester.
  • the deacylation reaction is carried out to finally generate sucralose. protection to avoid substitution of the hydroxyl group at the 6-position by a chlorine atom.
  • the present application mainly improves the step of deacetylation.
  • sodium methoxide (MeONa) is usually used as a catalyst and methanol (MeOH) is used as a solvent for the deacetylation reaction.
  • MeOH methanol
  • a side reaction of hydrolysis will occur, which will compete with the main reaction of alcoholysis, such as the reaction process such as the reaction formula ( 2) shown.
  • reaction formula (2) From the prior art shown in reaction formula (2), in the MeONa/MeOH catalytic system process, there is competition between the main reaction of alcoholysis and the side reaction of hydrolysis, and the hydrolysis reaction will consume the catalyst MeONa, and generate sodium acetate, and the sodium acetate is processed by The acid cation resin exchanges to produce acetic acid, which remains in the final product and affects the odor and taste of sucralose. Moreover, methyl acetate is generated by using methanol as a solvent, which increases the types of materials in the reaction system and increases the burden for post-processing.
  • the application adopts ethanol as solvent, it should be noted that the ethanol adopted in the application is dehydrated alcohol, rather than the mixed solution of ethanol and water, and a commercially available product is used.
  • Distillation step S120 Distill the sucralose-6-ethyl ester reaction solution to remove water therein.
  • Ethanol and water can be azeotroped, and the water in the system can be brought out by azeotropic distillation of the ethanolic solution of the sucralose-6-ethyl ester containing water.
  • the present application is relatively The technology adds a distillation step to remove a small amount of water in the sucralose-6-ethyl ester reaction solution.
  • One or more of the existing techniques can be used for the distillation method.
  • Catalysis step S130 adding an alkaline catalyst to the sucralose-6-ethyl ester reaction solution obtained in the distillation step, and reacting under preset conditions, so that the sucralose-6-ethyl ester undergoes a deacylation reaction to form trichlorosucralose-6-ethyl ester. Sucrose mixed solution.
  • the basic catalyst is added to the obtained sucralose-6-ethyl ester reaction solution.
  • the basic catalyst can be a strong base, a weak base, an organic base, an inorganic base, or a Supported forms of bases such as basic anion resins.
  • the acyl group at the 6-position of sucralose-6-ethyl ester is removed to become a hydroxyl group, and the sucralose-6-ethyl ester is reduced to sucralose.
  • the three-filtered sucrose mixed solution obtained above is filtered to remove the basic catalyst, and the catalyst can be recovered and reused.
  • the method for removing the catalyst is very simple, and only requires conventional means such as simple filtration, which greatly saves the process cost.
  • the application uses ethanol as a solvent, and the ethyl acetate of the by-product is a species originally applied in the sucralose production process flow, and can be applied in the process, thereby reducing the generation of sucralose.
  • the types of materials to be treated in the process flow significantly reduce the difficulty and cost of post-processing; and the water in the reaction system can be removed by azeotropic distillation, avoiding the occurrence of hydrolysis side reactions, and greatly reducing the content of by-product acetic acid , the product quality of sucralose is improved; and the catalyst in the present application can be recycled through simple treatment, which reduces the production cost of sucralose.
  • the step of removing impurities further includes: adding an acidic cationic resin to the sucralose mixed solution, and under the condition that the sucralose mixed solution is in a neutral condition , filtered to obtain a crude product solution of sucralose.
  • acidic cationic resin can be added to it, and the acidic cationic resin can exchange with metal cations and adsorb with other impurities.
  • the sucralose mixed solution is under neutral conditions and filtered to obtain a crude product solution of sucralose with higher purity.
  • the ethanol used as the solvent may be commercially available anhydrous ethanol, and in order to further remove the water therein, distillation may also be performed before use.
  • the amount of ethanol is not limited. In other embodiments, the amount of ethanol is 5-15 mL by volume based on each gram of sucralose-6-ethyl ester. If the consumption of ethanol is less than 5mL by volume, then the consumption of ethanol is insufficient, and the sucralose-6-ethyl ester cannot be completely dissolved; if the consumption of ethanol is greater than 15mL by volume, then the consumption of ethanol is excessive, causing unnecessary waste. , and can not bring other beneficial effects, and will increase the disposal amount of solvent removal in the subsequent sucralose crystallization process.
  • the distillation method and distillation conditions are not limited.
  • the distillation in the distillation step, the distillation is atmospheric distillation, the distillation temperature is 78-110° C., and the distillation time is 0.5- 6h.
  • Ethanol and a small amount of water in the sucralose-6-ethyl ester solution can azeotrope. Under the condition of distillation, ethanol and water azeotrope, thereby removing the water in the sucralose-6-ethyl ester reaction solution.
  • the distillation may be atmospheric distillation, the distillation temperature may be 78-110° C., and the distillation time may be 0.5-6 h. If the distillation temperature is less than 78° and the distillation time is less than 0.5h, the distillation temperature is too low and the distillation time is too short to effectively remove the moisture in the sucralose-6-ethyl ester reaction solution; if the distillation temperature is greater than 110°, the distillation time More than 6h, the distillation temperature is too high, the distillation time is too long, and the solvent ethanol will be taken away in large quantities, which cannot provide a sufficient solvent environment for the subsequent deacylation reaction of sucralose-6-ethyl ester, and the excessively high temperature and overheating. Long distillation times may cause decomposition of the reactants.
  • the moisture content in the sucralose-6-ethyl ester reaction solution may be distilled to ⁇ 5000 ppm, preferably ⁇ 2000 ppm.
  • the type of the basic catalyst is not limited.
  • the basic catalyst is sodium hydroxide and/or potassium hydroxide.
  • Sodium hydroxide and/or potassium hydroxide are cheap and easy to obtain, and have very low solubility in the sucralose-6-ethyl ester reaction solution. After the reaction is completed, it can be separated from the reaction system by a simple filtration process, and Recycling reduces the production cost of sucralose.
  • the amount of the basic catalyst is not limited. In other embodiments, the amount of basic catalyst is based on per gram of sucralose-6-ethyl ester by mass. 0.01 ⁇ 0.1g. If the amount of the basic catalyst is less than 0.01 g by mass, the amount of the catalyst is too small to catalyze the complete deacylation of sucralose-6-ethyl ester in a short time; if the amount of the basic catalyst is greater than 0.1 g by mass g, the amount of catalyst is too much, there is no obvious benefit, and the alkaline environment of the reaction solution is too strong, which may lead to unnecessary side reactions.
  • the preset conditions are not limited, as long as the deacylation reaction can be achieved; in other embodiments, the preset conditions are: under stirring conditions, The reaction temperature was set to 10-60°C, and the reaction time was set to 0.5-24 h. Among them, stirring helps the reactant and the catalyst to mix uniformly, so that the reaction proceeds smoothly. If the reaction temperature is less than 10°C and the reaction time is less than 0.5h, the reaction conditions are too mild, the time is too short, and the deacylation reaction cannot proceed completely; if the reaction temperature is higher than 60°C and the reaction time is longer than 6h, the reaction conditions are too intense, And if the time is too long, it may cause unnecessary side effects.
  • Sucralose-6-ethyl ester can be obtained by using the existing single-group protection method to produce sucralose, or can be a commercially available product, which is not limited in this application.
  • Reaction formula (3) shows the reaction process of the preparation method of sucralose according to another embodiment of the present application, as can be seen from reaction formula (3), sucralose-6-ethyl ester contains a small amount of water, Sucralose-6-ethyl ester is dissolved in ethanol and distilled, and water and ethanol are azeotroped to remove a small amount of water to suppress the side reaction of hydrolysis.
  • Deacylation is carried out by adding sodium hydroxide and/or potassium hydroxide as a catalyst to generate a mixed solution of sucralose, and the mixed solution of sucralose includes sodium hydroxide and/or potassium hydroxide and the by-products ethyl acetate, acetic acid Ethyl ester is a material type in the original sucralose production process, which can be recycled and applied, so after simple filtration, the crude sucralose product solution can be obtained.
  • test instruments and test conditions of the high performance liquid chromatography involved in this application are as follows:
  • high performance liquid chromatography can be used to determine the contents of sucralose-6-ethyl ester, acetic acid and sucralose, which will not be repeated in each embodiment.
  • the judging criterion for the complete conversion of sucralose-6-ethyl ester is: sampling the reaction system, and in the high-performance liquid chromatography of the measured sample, excluding the solvent peak, it is displayed on the chromatogram. Among the remaining other species, the relative peak area of sucralose-6-ethyl ester was ⁇ 0.5%.
  • the reaction yield is: the percentage of the actual yield of sucralose measured by the external standard method of high performance liquid chromatography to the theoretical yield of the reaction.
  • the crude product solution of sucralose obtained by any of the above-mentioned methods can obtain a crude product with less acetic acid content compared to the prior art, and reduce or even avoid the negative impact of acetic acid.
  • the acetic acid content in the obtained crude product solution of sucralose is less than or equal to 230ppm, or even lower.
  • the above method may further include: a refining step: crystallizing and purifying the crude sucralose product solution to obtain sucralose crystals.
  • the obtained crude product solution of sucralose is purified by crystallization to obtain high-purity sucralose crystals. Crystallization can be achieved by one or a combination of methods in the prior art.
  • the reaction system cools to 25°C, add 1 g of NaOH to the reaction solution, maintain the reaction at 25°C for 24 hours, determine the residual sucralose-6-ethyl ester by high performance liquid chromatography ⁇ 0.5% (relative peak area), stop stirring .
  • the catalyst is removed by filtration, the obtained filtrate contains the crude sucralose product, and the acetic acid content in the filtrate measured by high performance liquid chromatography is below the detection limit.
  • the sucralose product can be further purified according to conventional methods, and the obtained sucralose There is no acidic odor in the finished product.
  • the yield of sucralose from the deacetylation reaction of sucralose-6-ethyl ester determined by high performance liquid chromatography was 90%.
  • the reaction system cools to 40°C, add 2 g of KOH to the reaction solution, maintain the reaction at 40°C for 12 hours, determine the residual sucralose-6-ethyl ester by high performance liquid chromatography ⁇ 0.5% (relative peak area), stop stirring .
  • the catalyst is removed by filtration, the obtained filtrate contains the crude sucralose product, and the acetic acid content in the filtrate measured by high performance liquid chromatography is below the detection limit.
  • the sucralose product can be further purified according to conventional methods, and the obtained sucralose There is no acidic odor in the finished product.
  • the yield of sucralose by deacetylation of sucralose-6-ethyl ester determined by high performance liquid chromatography was 93%.
  • the sucralose product can be further purified according to conventional methods, and the obtained sucralose finished product has no acidic odor.
  • the yield of sucralose from the deacetylation reaction of sucralose-6-ethyl ester determined by high performance liquid chromatography was 85%.
  • the sucralose product can be further purified according to conventional methods, and the obtained sucralose finished product has no acidic odor.
  • the yield of sucralose from the deacetylation of sucralose-6-ethyl ester was determined to be 89% by high performance liquid chromatography.
  • Embodiment 5 (recovery catalyst is applied mechanically)
  • the reaction system was cooled to 25 ° C, the catalyst recovered in Example 4 was added to the reaction solution, and after maintaining the reaction at 25 ° C for 4 hours, the residual sucralose-6-ethyl ester was determined by high performance liquid chromatography. ⁇ 0.5% (relative peak area ), stop stirring. Filter to remove the catalyst, then use a small amount of acidic cation resin to adjust the pH of the filtrate to neutral, filter to remove the resin, the obtained filtrate contains the crude product of sucralose, and the acetic acid content in the filtrate determined by high performance liquid chromatography is below the detection limit, further, The sucralose product can be further purified according to conventional methods, and the obtained sucralose finished product has no acidic odor. The yield of sucralose produced by deacetylation of sucralose-6-ethyl ester was determined by high performance liquid chromatography, and the yield was 84%.
  • the resin is removed by filtration, the obtained filtrate contains the crude product of sucralose, and the filtrate is determined by high performance liquid chromatography to contain acetic acid, and the content is higher than 230ppm. Further, the sucralose product can be further purified according to conventional methods, and the obtained sucralose The finished product has a distinct acidic odor.
  • the yield of sucralose from the deacetylation of sucralose-6-ethyl ester was determined to be 89% by high performance liquid chromatography.
  • the beneficial effect of the present application is that the present application uses ethanol as a solvent, and the generated ethyl acetate is a species originally used in the production process of sucralose, and can be applied in the process, thereby reducing three
  • the types of materials to be treated in the production process of chlorosucrose significantly reduce the difficulty and cost of post-treatment; and the water in the reaction system can be removed by azeotropic distillation, avoiding the occurrence of hydrolysis side reactions, and greatly reducing by-products
  • the content of acetic acid improves the product quality of sucralose; and the catalyst in the present application can be recycled through simple treatment, thereby reducing the production cost of sucralose.

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Abstract

La présente invention concerne un procédé de préparation de sucralose, une solution de produit brut et du sucralose, le procédé comprenant les étapes consistant à : dissoudre un ester de sucralose-6-éthyle dans de l'éthanol pour former une solution de réaction d'ester de sucralose-6-éthyle ; distiller la solution de réaction d'ester de sucralose-6-éthyle pour éliminer l'humidité contenue dans celle-ci ; ajouter un catalyseur alcalin tel que de l'hydroxyde de sodium ou l'hydroxyde de potassium à la solution de réaction d'ester de sucralose-6-éthyle pour former une solution mixte de sucralose ; et filtrer la solution mixte de sucralose pour obtenir une solution de produit brut de sucralose.
PCT/CN2020/141531 2020-12-30 2020-12-30 Procédé de préparation de sucralose, solution de produit brut et sucralose WO2022141229A1 (fr)

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PCT/CN2020/141531 WO2022141229A1 (fr) 2020-12-30 2020-12-30 Procédé de préparation de sucralose, solution de produit brut et sucralose
CN202080004019.7A CN112771059A (zh) 2020-12-30 2020-12-30 三氯蔗糖的制备方法、粗产品溶液及三氯蔗糖

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CN113767109A (zh) * 2021-08-04 2021-12-07 安徽金禾实业股份有限公司 三氯蔗糖的制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5034551A (en) * 1990-04-23 1991-07-23 Noramco, Inc. Process for recovery of organotin esters from reaction mixtures containing the same and re-use of the recovered organotin compounds
CN101121736A (zh) * 2007-09-05 2008-02-13 江苏天禾药物研究所有限公司 三氯蔗糖的制备方法
CN104004032A (zh) * 2014-06-14 2014-08-27 福州大学 一种三氯蔗糖-6-乙酸酯连续脱乙酰基制三氯蔗糖的方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5034551A (en) * 1990-04-23 1991-07-23 Noramco, Inc. Process for recovery of organotin esters from reaction mixtures containing the same and re-use of the recovered organotin compounds
CN101121736A (zh) * 2007-09-05 2008-02-13 江苏天禾药物研究所有限公司 三氯蔗糖的制备方法
CN104004032A (zh) * 2014-06-14 2014-08-27 福州大学 一种三氯蔗糖-6-乙酸酯连续脱乙酰基制三氯蔗糖的方法

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