CN106946956B - Recrystallization method and application of sucrose-6-acetate - Google Patents
Recrystallization method and application of sucrose-6-acetate Download PDFInfo
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- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
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Abstract
The invention discloses a recrystallization method of sucrose-6-acetate and application thereof, wherein the recrystallization method comprises the following steps: adding a solvent into a sucrose-6-acetate mixture obtained by sucrose esterification reaction, stirring, dissolving, filtering, and drying to obtain sucrose-6-acetate, wherein the solvent is a mixture of a nitrile solvent and an ether solvent. The recrystallization method can improve the purity of the sucrose-6-acetate so as to reduce the adverse effect on the subsequent chlorination process.
Description
Technical Field
The invention relates to a sucralose production process, in particular to a recrystallization method of sucrose-6-acetate and application thereof.
Background
Sucralose (chemical name is 4,1',6' -trichloro-4, 1',6' -trideoxygalactosucrose) is a novel functional sweetener only taking sucrose as a raw material, has sweetness which can be 600 times that of the sucrose, and has the characteristics of no energy, high sweetness, pure sweetness, high safety, caries resistance, wide application range and the like. Sucrose-6-acetate is a product of the first esterification reaction in the sucralose synthesis process, is a very important intermediate, and the quality of the intermediate is directly related to the chlorination yield of the next step, so that the quality and the yield of the sucralose product are influenced.
The existing sucralose synthesis process does not generally crystallize sucrose-6-acetate, but directly adds the esterification reaction mixed solution to the next step for reaction, so that the by-products in the esterification step are brought to the next step, side reactions are increased, more chlorinating agents are consumed, impurities which cannot be reused are generated, sugar in the chlorination step is carbonized, the cost is increased, and the environmental pressure is increased.
CN103554196A discloses that the crystallization of sucrose-6-acetate can be relatively regular by adding petroleum ether under the condition of ultrasonic flow at a specific temperature, and then the sucrose-6-acetate is recrystallized by using ethyl acetate, but the solubility of the sucrose-6-acetate in the ethyl acetate is very small, and the pretreatment process is relatively complex and is not beneficial to industrial production.
CN103936799A discloses the removal of solvent water and dimethylformamide at the end of the esterification reaction, and the addition of a mixed solvent of acetone and methanol for recrystallization of sucrose-6-acetate, which requires the evaporation of DMF to dryness prior to crystallization and does not give the purity of the final product and the benefits of crystallization.
Other recrystallization techniques of sucrose-6-acetate are not reported in many cases, and most of the recrystallization methods introduce solvents with high toxicity or cause solvent residues to influence the yield of the next chlorination process or the quality of sucralose products.
Disclosure of Invention
The invention aims to provide a recrystallization method of sucrose-6-acetate, which can improve the purity of the sucrose-6-acetate so as to reduce the adverse effect on the subsequent chlorination process.
A method for recrystallization of sucrose-6-acetate comprising: adding a solvent into a sucrose-6-acetate mixture obtained by sucrose esterification reaction, stirring, dissolving, cooling, filtering and drying to obtain the sucrose-6-acetate, wherein the solvent is a mixture of a nitrile solvent and an ether solvent.
The sucrose esterification reaction is that dibutyltin oxide and cyclohexane are added into a DMF solution of sucrose, and reflux water-splitting reaction is carried out at a certain temperature; cooling after the reaction is finished, dripping acetic anhydride, heating to room temperature after half an hour, and continuously stirring for reaction; after the reaction is finished, adding water, stirring for half an hour, then carrying out reduced pressure distillation, removing water and cyclohexane and most of DMF, and obtaining the sucrose-6-acetate mixture. The sucrose-6-acetate mixture is a mixture of sucrose-6-acetate, DMF and impurities.
The invention uses nitrile and ether as mixed crystallization solvent to recrystallize sucrose-6-acetate, and obtains sucrose-6-acetate crystal through some subsequent processes. The method has the advantages of low toxicity, low cost and easy recovery, and the obtained crystallization solvent has less residue, is not easy to absorb moisture, is more durable for storage, and has no adverse effect on the next chlorination process.
The specific kind of the nitrile solvent and the ether solvent may affect the recrystallization effect, and different impurities may be selectively removed using different combinations of solvents, and preferably, the nitrile solvent is at least one of acetonitrile, propionitrile, butyronitrile, isobutyronitrile, and isopropylnitrile.
Preferably, the ether solvent is at least one of diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether and tert-butyl methyl ether.
The amount ratio of the solvent is preferably 1:1 to 10:1, because the crystallization effect is also affected by the amount ratio of the nitrile solvent to the ether solvent.
Preferably, the stirring temperature is 40 to 80 ℃.
Preferably, the stirring speed is 400 to 1000 rpm.
The recrystallization temperature has a great influence on the yield and purity of the product, and is preferably-5 ℃ to 0 ℃.
Preferably, the recrystallization time is 1 to 2 hours.
DMF as a reaction solvent is difficult to remove completely, the crystallization system is simple to process, all DMF does not need to be removed, and good crystallization effect can be obtained, and the sucrose-6-acetate mixture is obtained by removing water, cyclohexane and more than 85% of DMF from a reaction solution.
The invention also provides a preparation method of sucralose, which comprises the following steps:
(1) carrying out esterification reaction on sucrose to obtain a sucrose-6-acetate mixture;
(2) obtaining sucrose-6-acetate according to the recrystallization method;
(3) and (3) carrying out chlorination reaction on the sucrose-6-acetate to obtain the sucralose.
According to the invention, after the esterification reaction is finished, the sucrose-6-acetate mixture is recrystallized by adopting a special solvent combination, and then the subsequent chlorination reaction is carried out, so that the carbonization phenomenon of the chlorination reaction can be effectively overcome, the impurity content is reduced, the product quality is improved, and the method has a better industrial value.
Compared with the prior art, the invention has the beneficial effects that:
(1) according to the invention, the mixture of the nitrile solvent and the ether solvent is used as the crystallization solvent, the operation process is simple, the solvent cost is low, the solvent is easy to recover, the obtained crystallization product has high purity, the solvent residue is less, the moisture absorption is not easy, and the storage is more durable;
(2) when the sucrose-6-acetate obtained by the crystallization method is used for the next reaction, the side reaction and the consumption of chlorinated reagent can be reduced, and the sugar carbonization can be prevented.
Detailed Description
Example 1
500g of sucrose and 2L of DMF solution were introduced into a 5L four-necked flask equipped with a stirring paddle, a thermometer and a condenser tube with a water separator. Heating to 60 ℃, adding 375g of dibutyltin oxide and 1.5L of cyclohexane after sucrose is dissolved, heating to 90-95 ℃, refluxing and water diversion, finishing the reaction for 5 hours, cooling to 5 ℃, dropwise adding 157.5g of acetic anhydride, heating to room temperature after half an hour, continuously stirring for 4 hours, adding 150mL of water, stirring for half an hour, carrying out reduced pressure distillation, removing water, cyclohexane and most of DMF (dimethyl formamide) to obtain 700g of reaction mixture, and analyzing the components by adopting high-efficiency liquid, wherein the results are shown in Table 1.
20g of the mixture is weighed, heated to 45 ℃, 10mL of acetonitrile and 5mL of diethyl ether are added with stirring at a speed of 450 rpm, and after the concentrate is completely dissolved, the temperature is slowly reduced, and white precipitate appears. Standing for 2h at the temperature of between 5 ℃ below zero and 0 ℃, filtering and drying to obtain 14.09g of white powdery crystals. The content of sucrose-6-acetate is 98.6% by high performance liquid detection, and the specific analysis result is shown in table 2.
Example 2
500g of sucrose and 2L of DMF solution were charged into a 5L four-necked flask equipped with a stirring paddle and a thermometer, and a condenser tube with a water separator. Heating to 60 ℃, adding 375g of dibutyltin oxide and 1.5L of cyclohexane after sucrose is dissolved, heating to 90-95 ℃, refluxing and water dividing, finishing the reaction for 5 hours, cooling to 5 ℃, dropwise adding 157.5g of acetic anhydride, heating to room temperature after half an hour, continuously stirring for 4 hours, adding 150mL of water, stirring for half an hour, carrying out reduced pressure distillation, and removing water, cyclohexane and most of DMF to obtain 700g of reaction mixture.
50g of the mixture is weighed, heated to 40 ℃ and stirred at 500 rpm with the addition of 15mL of propionitrile and 7.5mL of diethyl ether, and after the concentrate has completely dissolved, the temperature is slowly reduced and a white precipitate appears. Standing for 2h at-5-0 ℃, filtering and drying to obtain 35.29g of white powdery crystals. The content of sucrose-6-acetate is 98.4% by high performance liquid detection, and the specific analysis result is shown in table 2.
Example 3
500g of sucrose and 2L of DMF solution were charged into a 5L four-necked flask equipped with a stirring paddle and a thermometer, and a condenser tube with a water separator. Heating to 60 ℃, adding 375g of dibutyltin oxide and 1.5L of cyclohexane after sucrose is dissolved, heating to 90-95 ℃, refluxing and water dividing, finishing the reaction for 5 hours, cooling to 5 ℃, dropwise adding 157.5g of acetic anhydride, heating to room temperature after half an hour, continuously stirring for 4 hours, adding 150mL of water, stirring for half an hour, carrying out reduced pressure distillation, and removing water, cyclohexane and most of DMF to obtain 700g of reaction mixture.
Weighing 50g of the mixture, heating to 45 ℃, adding 40mL of butyronitrile and 8mL of diethyl ether while stirring at the speed of 500 r/min, and slowly cooling to obtain white precipitate after the concentrate is completely dissolved. Standing for 1.5h at the temperature of between 5 ℃ below zero and 0 ℃, filtering and drying to obtain 35.66g of white powdery crystals. The content of sucrose-6-acetate is 97.4% by high performance liquid detection, and the specific analysis result is shown in Table 2.
Example 4
500g of sucrose and 2LDMF solution were charged into a 5L four-necked flask equipped with a stirring paddle and a thermometer, and a condenser tube with a water separator. Heating to 60 ℃, adding 375g of dibutyltin oxide and 1.5L of cyclohexane after sucrose is dissolved, heating to 90-95 ℃, refluxing and water dividing, finishing the reaction for 5 hours, cooling to 5 ℃, dropwise adding 157.5g of acetic anhydride, heating to room temperature after half an hour, continuously stirring for 4 hours, adding 150mL of water, stirring for half an hour, carrying out reduced pressure distillation, and removing water, cyclohexane and most of DMF to obtain 700g of reaction mixture.
20g of the mixture was weighed, heated to 70 ℃ and stirred at 600 rpm with 12mL of isobutyronitrile and 4mL of tetrahydrofuran, and after the concentrate had dissolved completely, the temperature was slowly reduced to give a white precipitate. Standing for 1.5h at-5-0 ℃, filtering and drying to obtain 14.20g of white powdery crystals. The content of sucrose-6-acetate is 97.8% by high performance liquid detection, and the specific analysis result is shown in Table 2.
Example 5
500g of sucrose and 2L of DMF solution were charged into a 5L four-necked flask equipped with a stirring paddle and a thermometer, and a condenser tube with a water separator. Heating to 60 ℃, adding 375g of dibutyltin oxide and 1.5L of cyclohexane after sucrose is dissolved, heating to 90-95 ℃, refluxing and water dividing, finishing the reaction for 5 hours, cooling to 5 ℃, dropwise adding 157.5g of acetic anhydride, heating to room temperature after half an hour, continuously stirring for 4 hours, adding 150mL of water, stirring for half an hour, carrying out reduced pressure distillation, and removing water, cyclohexane and most of DMF to obtain 700g of reaction mixture.
30g of the mixture is weighed, heated to 65 ℃, and 12mL of acetonitrile and 6mL of tetrahydrofuran are added while stirring at a speed of 550 rpm, and after the concentrate is completely dissolved, the temperature is slowly reduced, and a white precipitate appears. Standing for 2h at-5-0 ℃, filtering and drying to obtain 21.18g of white powdery crystals. The content of sucrose-6-acetate is 98.4% by high performance liquid detection, and the specific analysis result is shown in table 2.
Example 6
500g of sucrose and 2L of DMF solution were charged into a 5L four-necked flask equipped with a stirring paddle and a thermometer, and a condenser tube with a water separator. Heating to 60 ℃, adding 375g of dibutyltin oxide and 1.5L of cyclohexane after sucrose is dissolved, heating to 90-95 ℃, refluxing and water dividing, finishing the reaction for 5 hours, cooling to 5 ℃, dropwise adding 157.5g of acetic anhydride, heating to room temperature after half an hour, continuously stirring for 4 hours, adding 150mL of water, stirring for half an hour, carrying out reduced pressure distillation, and removing water, cyclohexane and most of DMF to obtain 700g of reaction mixture.
30g of the mixture was weighed, heated to 65 ℃ and 21mL of isopropionitrile and 5mL of ethylene glycol dimethyl ether were added with stirring at 750 rpm, and after the concentrate had dissolved completely, the temperature was slowly reduced to give a white precipitate. Standing for 2h at-5-0 ℃, filtering and drying to obtain 21.28g of white powdery crystals. The content of sucrose-6-acetate is 97.9% by high performance liquid detection, and the specific analysis result is shown in Table 2.
Example 7
500g of sucrose and 2L of DMF solution were charged into a 5L four-necked flask equipped with a stirring paddle and a thermometer, and a condenser tube with a water separator. Heating to 60 ℃, adding 375g of dibutyltin oxide and 1.5L of cyclohexane after sucrose is dissolved, heating to 90-95 ℃, refluxing and water dividing, finishing the reaction for 5 hours, cooling to 5 ℃, dropwise adding 157.5g of acetic anhydride, heating to room temperature after half an hour, continuously stirring for 4 hours, adding 150mL of water, stirring for half an hour, carrying out reduced pressure distillation, and removing water, cyclohexane and most of DMF to obtain 700g of reaction mixture.
100g of the mixture was weighed, heated to 80 ℃ and 40mL of butyronitrile and 10mL of tert-butyl methyl ether were added with stirring at 800 rpm, and after the concentrate had dissolved completely, the temperature was slowly reduced and a white precipitate appeared. Standing for 2h at the temperature of between 5 ℃ below zero and 0 ℃, filtering and drying to obtain 70.75g of white powdery crystals. The content of sucrose-6-acetate is 98.2% by high performance liquid detection, and the specific analysis result is shown in table 2.
TABLE 1 ingredient content information of mixture before crystallization
| Substance(s) | Residual sugar | Monoester impurities | Diester impurities | Sucrose-6-acetate |
| Mass percent | 3.5％ | 4.8％ | 5.1％ | 86.6％ |
TABLE 2 information on the contents of components of the sample after crystallization
| Substance(s) | Residual sugar | Monoester impurities | Diester impurities | Sucrose-6-acetate |
| Example 1 | 1.11％ | 0.23％ | 0.08％ | 98.58％ |
| Example 2 | 1.34％ | 0.21％ | 0.04％ | 98.41％ |
| Examples of the invention3 | 2.45％ | 0.15％ | 0.02％ | 97.38％ |
| Example 4 | 1.98％ | 0.16％ | 0.03％ | 97.83％ |
| Example 5 | 1.27％ | 0.25％ | 0.10％ | 98.38％ |
| Example 6 | 1.85％ | 0.20％ | 0.03％ | 97.92％ |
| Example 7 | 1.57％ | 0.21％ | 0.05％ | 98.17％ |
The crystalline product of example 7 was used for the subsequent chlorination reaction
Weighing 11.5g of white crystals, adding the white crystals into a 500mL three-necked flask, adding 210mL of the solution of the mixed solution of the obtained. After the addition is finished, stirring and reacting for 0.5h at room temperature, and raising the temperature by using a program to obtain chlorination reaction liquid. Sampling, diluting, centrifuging, and performing high performance liquid chromatography on supernatant to obtain detection results shown in Table 3.
Comparative example 8
500g of sucrose and 2L of DMF solution were charged into a 5L four-necked flask equipped with a stirring paddle and a thermometer, and a condenser tube with a water separator. Heating to 60 ℃, adding 375g of dibutyltin oxide and 1.5L of cyclohexane after sucrose is dissolved, heating to 90-95 ℃, refluxing and water dividing, finishing the reaction for 5 hours, cooling to 5 ℃, dropwise adding 157.5g of acetic anhydride, heating to room temperature after half an hour, continuously stirring for 4 hours, adding 150mL of water, stirring for half an hour, carrying out reduced pressure distillation, and removing water, cyclohexane and most of DMF to obtain 700g of reaction mixture.
Weighing 28g of the reaction liquid mixture, adding the mixture into a 500mL three-necked flask, adding 200mL of the LDMF solution, stirring at the temperature of between 15 ℃ below zero and 20 ℃ to dissolve the esterification reaction liquid mixture, slowly adding 54g of the triton, and maintaining the reaction temperature within the range of between 15 ℃ below zero and 5 ℃. After the addition is finished, stirring and reacting for 0.5h at room temperature, and raising the temperature by using a program to obtain chlorination reaction liquid. Sampling, diluting, centrifuging, and performing high performance liquid chromatography on supernatant to obtain detection results shown in Table 3.
Table 3 comparison of chlorination results for examples 7 and 8
As can be seen from the results in Table 3, the crystallization method of the present invention can significantly reduce the amount of chlorination reagent, reduce carbonization, increase chlorination yield, and reduce the content of chlorinated impurities, thereby having better industrial application value.
Claims (7)
1. A method for preparing sucrose-6-acetate, comprising: :
(1) adding dibutyltin oxide and cyclohexane into a DMF solution of cane sugar, and carrying out reflux water-splitting reaction at a certain temperature; cooling after the reaction is finished, dripping acetic anhydride, heating to room temperature after half an hour, and continuously stirring for reaction; adding water after the reaction is finished, stirring for half an hour, then carrying out reduced pressure distillation, removing water and cyclohexane and most of DMF, and obtaining the sucrose-6-acetate mixture;
(2) adding a solvent into a sucrose-6-acetate mixture obtained by sucrose esterification reaction, stirring, dissolving, cooling, filtering and drying to obtain sucrose-6-acetate, wherein the solvent is a mixture of a nitrile solvent and an ether solvent;
the volume ratio of the nitrile solvent to the ether solvent is 1: 1-10: 1;
the nitrile solvent is at least one of acetonitrile, propionitrile, butyronitrile, isobutyronitrile and isopropylnitrile;
the ether solvent is at least one of diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether and tert-butyl methyl ether.
2. The method for producing sucrose-6-acetate as described in claim 1, wherein the stirring temperature is 40 to 80 ℃.
3. The method for producing sucrose-6-acetate as described in claim 1, wherein the stirring speed is 400 to 1000 rpm.
4. The method of claim 1, wherein the recrystallization temperature is from-5 ℃ to 0 ℃.
5. The method for producing sucrose-6-acetate as described in claim 1, wherein the recrystallization time is 1 to 2 hours.
6. The method of claim 1, wherein the sucrose-6-acetate mixture is obtained from the reaction mixture by removing water, cyclohexane and 85% or more of DMF.
7. A method for preparing sucralose, comprising:
(1) obtaining sucrose-6-acetate according to the method of any one of claims 1 to 6;
(2) and (3) carrying out chlorination reaction on the sucrose-6-acetate to obtain the sucralose.
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| CN109593107A (en) * | 2018-12-10 | 2019-04-09 | 安徽金禾实业股份有限公司 | A kind of method of purification of cane sugar-6-acetic ester |
| CN111647023B (en) * | 2020-05-22 | 2022-02-11 | 安徽金禾实业股份有限公司 | Industrial recovery method of sucralose waste sucrose acetate |
| CN113214330A (en) * | 2021-05-13 | 2021-08-06 | 安徽金禾化学材料研究所有限公司 | Purification and chlorination process of sucrose-6-ethyl ester |
| CN114437146B (en) * | 2022-01-10 | 2023-12-08 | 福州大学 | Production process of sucralose-6-acetate |
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| CN101132705A (en) * | 2005-02-22 | 2008-02-27 | 法马德医疗保险私人有限公司 | Tin mediated regioselective synthesis of sucrose-6-esters |
| CN101274949A (en) * | 2007-03-27 | 2008-10-01 | 苏州开元民生化学科技有限公司 | Preparation for sucrose-6-ester |
| CN103554196A (en) * | 2013-11-22 | 2014-02-05 | 长沙理工大学 | Crystallization method of sucrose-6-acetate |
| CN103936799A (en) * | 2014-04-24 | 2014-07-23 | 南京工业大学 | Synthesis method of cane sugar-6-acetic acid ester |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1295237C (en) * | 2003-10-01 | 2007-01-17 | 常州市牛塘化工厂 | Method for preparing sucrose-6-ethyl ester |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101132705A (en) * | 2005-02-22 | 2008-02-27 | 法马德医疗保险私人有限公司 | Tin mediated regioselective synthesis of sucrose-6-esters |
| CN101274949A (en) * | 2007-03-27 | 2008-10-01 | 苏州开元民生化学科技有限公司 | Preparation for sucrose-6-ester |
| CN103554196A (en) * | 2013-11-22 | 2014-02-05 | 长沙理工大学 | Crystallization method of sucrose-6-acetate |
| CN103936799A (en) * | 2014-04-24 | 2014-07-23 | 南京工业大学 | Synthesis method of cane sugar-6-acetic acid ester |
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