CN106946956A - A kind of recrystallization method of acetic acid esters of sucrose 6 and its application - Google Patents
A kind of recrystallization method of acetic acid esters of sucrose 6 and its application Download PDFInfo
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- CN106946956A CN106946956A CN201710156158.1A CN201710156158A CN106946956A CN 106946956 A CN106946956 A CN 106946956A CN 201710156158 A CN201710156158 A CN 201710156158A CN 106946956 A CN106946956 A CN 106946956A
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- cane sugar
- acetic ester
- sucrose
- recrystallization method
- recrystallization
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
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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
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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
- C07H1/06—Separation; Purification
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- 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- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
Abstract
The invention discloses a kind of recrystallization method of acetic acid esters of sucrose 6 and its application, the recrystallization method includes:Add solvent in the acetate mixture of sucrose 6 obtained to sucrose esterification, stirring, dissolving, then through filtering, dry the acetic acid esters of sucrose 6, wherein the solvent is the mixture of nitrile solvents and ether solvent.The recrystallization method can improve the purity of the acetic acid esters of sucrose 6, to reach the adverse effect reduced to follow-up chloro technique.
Description
Technical field
The present invention relates to Sucralose production technology, the recrystallization method of specially a kind of cane sugar-6-acetic ester and its should
With.
Background technology
Sucralose (the entitled chloro- deoxidation sucraloses of 4,1', 6'- tri- of 4,1', 6'- tri- of chemistry), is a kind of unique with sugarcane
Sugar is the feature novel sweetener of raw material, and sugariness is up to 600 times of sucrose, and with noenergy, sugariness is high, sweet taste is pure, height
The features such as spending safety, anti-caries tooth, have a wide range of application.Cane sugar-6-acetic ester is that first step esterification is anti-in Sucralose synthesis technique
The product answered, is a very important intermediate, and its quality is directly connected to the chlorination yield of next step to influence
To the quality and yield of Sucralose product.
Sucralose synthesis technique now is not crystallized typically to cane sugar-6-acetic ester, but esterification is mixed
Close solution and be added directly into next step reaction, the accessory substance of esterif iotacation step can be not only brought into next step work by such technique
Skill so that side reaction increases, consumes more chlorination reagents, and can produce some impurity that can not be recycled, and causes
Sugar charcoal in chlorinating step, improves cost, increases environmental pressure.
CN103554196A disclose in the case of the ultrasonic flow of specified temp add petroleum ether can cause sucrose-
The crystallization of 6- acetic acid esters is more regular, and then cane sugar-6-acetic ester is recrystallized using ethyl acetate, but sucrose -6- acetic acid
Solubility of the ester in ethyl acetate is very small, while pretreatment process is more complicated, is unfavorable for industrialized production.
CN103936799A is disclosed to be terminated to remove aqueous solvent and dimethylformamide in esterification, adds acetone and first
The mixed solvent of alcohol carries out the recrystallization of cane sugar-6-acetic ester, and this method needs DMF being evaporated before crystallization, and does not have
Provide the benefit that the purity and zone of a crystal of final products are come.
Other are few about the report of cane sugar-6-acetic ester recrystallization technology, and these recrystallization methods can draw mostly
Enter the larger solvent of toxicity, or dissolvent residual can be caused, have influence on chloridization process yield or the Sucralose production of next step
Quality.
The content of the invention
It is an object of the invention to provide a kind of recrystallization method of cane sugar-6-acetic ester, the recrystallization method can be carried
The purity of high-sucrose -6- acetic acid esters, to reach the adverse effect reduced to follow-up chloro technique.
A kind of recrystallization method of cane sugar-6-acetic ester, including:The cane sugar-6-acetic ester obtained to sucrose esterification
Add solvent in mixture, stirring, dissolving, then through cooling, filtering, dry cane sugar-6-acetic ester, wherein the solvent is nitrile
The mixture of class solvent and ether solvent.
Described sucrose esterification refers to, Dibutyltin oxide and hexamethylene is added in the DMF solution of sucrose, one
Reflux water-dividing reacts under constant temperature degree;Question response terminates, cooling, and acetic anhydride is added dropwise, and room temperature is warming up to after half an hour, continues to stir anti-
Should;Reaction, which is finished, adds water, and vacuum distillation after stirring half an hour removes water and hexamethylene and major part DMF, obtains described sugarcane
Sugar -6- acetate mixtures.The cane sugar-6-acetic ester mixture is the mixture of cane sugar-6-acetic ester, DMF and impurity.
The present invention makees mixed crystallization solvent using nitrile and ethers, cane sugar-6-acetic ester is recrystallized, and pass through one
A little subsequent techniques obtain cane sugar-6-acetic ester crystal.This method has hypotoxicity, low cost, the advantage easily reclaimed, and obtains
Recrystallisation solvent residual it is few, be difficult the moisture absorption, more resistant to preservation, next step chloridization process not adversely affected.
Nitrile solvents and the specific species of ether solvent influence whether the effect of recrystallization, using different solvent combinations,
Different impurity can be optionally removed, preferably, described nitrile solvents are acetonitrile, propionitrile, butyronitrile, isobutyronitrile and different
At least one in propionitrile.
Preferably, described ether solvent is in ether, tetrahydrofuran, glycol dimethyl ether and t-butyl methyl ether
It is at least one.
In addition, the amount ratio of solvent also can produce influence to crystallization effect, preferably, described nitrile solvents and ethers
The volume ratio of solvent is 1:1~10:1.
Preferably, whipping temp is 40~80 DEG C.
Preferably, mixing speed is 400~1000 revs/min.
The temperature of recrystallization can produce large effect to the yield and purity of product, preferably, recrystallization temperature for-
5 DEG C~0 DEG C.
Preferably, the recrystallization time is 1~2h.
It is relatively difficult to eliminate as the DMF of reaction dissolvent, handles simple using the crystallizing system of the present invention, it is not necessary to by institute
Some DMF is removed, and can also obtain good crystallization effect, cane sugar-6-acetic ester mixture by reaction solution remove water, hexamethylene and
More than 85% DMF is obtained.
Present invention also offers a kind of preparation method of Sucralose, including:
(1) sucrose carries out the cane sugar-6-acetic ester mixture that esterification is obtained;
(2) cane sugar-6-acetic ester is obtained according to described recrystallization method;
(3) cane sugar-6-acetic ester carries out chlorination reaction and obtains Sucralose.
In the present invention, after esterification terminates, by using special solvent combination to cane sugar-6-acetic ester mixture
Recrystallized, then carry out follow-up chlorination reaction, can efficiently against chlorination charing phenomenon, reduce impurity and contain
Amount, improves product quality, with more preferable industrial value.
Compared with the existing technology, beneficial effects of the present invention are embodied in:
(1) present invention is by using the mixture of nitrile solvents and ether solvent as recrystallisation solvent, and operating process is simple,
The low easy crystalline product purity height for reclaiming, obtaining of solvent cost, dissolvent residual is few, the moisture absorption is difficult, more resistant to preservation;
(2) when the cane sugar-6-acetic ester obtained using the method for crystallising of the present invention is used for next step reaction, it is possible to reduce secondary
Reaction and the consumption of chlorinating agent, prevent sugar charcoal.
Embodiment
Embodiment 1
500g sucrose and 2L DMF solutions are added in a 5L four-hole boiling flask, agitating paddle, thermometer are installed and carried
The condenser pipe of water knockout drum.60 DEG C are heated to, treats that sucrose dissolves, 375g Dibutyltin oxides and 1.5L hexamethylenes, heating is added
To 90-95 DEG C of reflux water-dividing, 5 hour reactions terminate, and be cooled to 5 DEG C, 157.5g acetic anhydrides are added dropwise, room is warming up to after half an hour
Temperature, continues to stir 4h, adds 150mL water, and vacuum distillation after stirring half an hour removes water and hexamethylene and major part DMF, obtained
To 700g reactant mixtures, its composition is analyzed using efficient liquid phase, 1 is the results are shown in Table.
Said mixture 20g is weighed, 45 DEG C are heated to, 10mL acetonitriles are added while stirring using 450 revs/min of speed
With 5mL ether, thing to be concentrated is all after dissolving, and white precipitate occurs in slow cooling.2h, mistake are stood under the conditions of -5 DEG C~0 DEG C
Filter, drying, obtains white powder crystal 14.09g.Detected through efficient liquid phase, its cane sugar-6-acetic ester content is 98.6%,
Concrete analysis the results are shown in Table 2.
Embodiment 2
500g sucrose and 2L DMF solutions are added in a 5L four-hole boiling flask, agitating paddle and thermometer, and band are installed
There is the condenser pipe of water knockout drum.60 DEG C are heated to, treats that sucrose dissolves, 375g Dibutyltin oxides and 1.5L hexamethylenes is added, plus
Heat to 90-95 DEG C of reflux water-dividing, 5 hour reactions terminate, are cooled to 5 DEG C, 157.5g acetic anhydrides are added dropwise, are warming up to after half an hour
Room temperature, continues to stir 4h, adds 150mL water, and vacuum distillation after stirring half an hour removes water and hexamethylene and major part DMF,
Obtain 700g reactant mixtures.
Said mixture 50g is weighed, 40 DEG C are heated to, 15mL propionitrile is added while stirring using 500 revs/min of speed
With 7.5mL ether, thing to be concentrated is all after dissolving, and white precipitate occurs in slow cooling.2h is stood under the conditions of -5 DEG C~0 DEG C,
Filtering, drying, obtains white powder crystal 35.29g.Detected through efficient liquid phase, its cane sugar-6-acetic ester content is
98.4%, concrete analysis the results are shown in Table 2.
Embodiment 3
500g sucrose and 2L DMF solutions are added in a 5L four-hole boiling flask, agitating paddle and thermometer, and band are installed
There is the condenser pipe of water knockout drum.60 DEG C are heated to, treats that sucrose dissolves, 375g Dibutyltin oxides and 1.5L hexamethylenes is added, plus
Heat to 90-95 DEG C of reflux water-dividing, 5 hour reactions terminate, are cooled to 5 DEG C, 157.5g acetic anhydrides are added dropwise, are warming up to after half an hour
Room temperature, continues to stir 4h, adds 150mL water, and vacuum distillation after stirring half an hour removes water and hexamethylene and major part DMF,
Obtain 700g reactant mixtures.
Said mixture 50g is weighed, 45 DEG C are heated to, 40mL butyronitrile is added while stirring using 500 revs/min of speed
With 8mL ether, thing to be concentrated is all after dissolving, and white precipitate occurs in slow cooling.1.5h is stood under the conditions of -5 DEG C~0 DEG C,
Filtering, drying, obtains white powder crystal 35.66g.Detected through efficient liquid phase, its cane sugar-6-acetic ester content is
97.4%, concrete analysis the results are shown in Table 2.
Embodiment 4
500g sucrose and 2LDMF solution are added in a 5L four-hole boiling flask, agitating paddle and thermometer are installed, and carry
The condenser pipe of water knockout drum.60 DEG C are heated to, treats that sucrose dissolves, 375g Dibutyltin oxides and 1.5L hexamethylenes, heating is added
To 90-95 DEG C of reflux water-dividing, 5 hour reactions terminate, and be cooled to 5 DEG C, 157.5g acetic anhydrides are added dropwise, room is warming up to after half an hour
Temperature, continues to stir 4h, adds 150mL water, and vacuum distillation after stirring half an hour removes water and hexamethylene and major part DMF, obtained
To 700g reactant mixtures.
Said mixture 20g is weighed, 70 DEG C are heated to, 12mL isobutyls are added while stirring using 600 revs/min of speed
Nitrile and 4mL tetrahydrofurans, thing to be concentrated is all after dissolving, and white precipitate occurs in slow cooling.It is quiet under the conditions of -5 DEG C~0 DEG C
1.5h is put, is filtered, drying obtains white powder crystal 14.20g.Detected through efficient liquid phase, its cane sugar-6-acetic ester content
For 97.8%, concrete analysis the results are shown in Table 2.
Embodiment 5
500g sucrose and 2L DMF solutions are added in a 5L four-hole boiling flask, agitating paddle and thermometer, and band are installed
There is the condenser pipe of water knockout drum.60 DEG C are heated to, treats that sucrose dissolves, 375g Dibutyltin oxides and 1.5L hexamethylenes is added, plus
Heat to 90-95 DEG C of reflux water-dividing, 5 hour reactions terminate, are cooled to 5 DEG C, 157.5g acetic anhydrides are added dropwise, are warming up to after half an hour
Room temperature, continues to stir 4h, adds 150mL water, and vacuum distillation after stirring half an hour removes water and hexamethylene and major part DMF,
Obtain 700g reactant mixtures.
Said mixture 30g is weighed, 65 DEG C are heated to, 12mL acetonitriles are added when being stirred using 550 revs/min of speed
With 6mL tetrahydrofurans, thing to be concentrated is all after dissolving, and white precipitate occurs in slow cooling.Stood under the conditions of -5 DEG C~0 DEG C
2h, is filtered, and drying obtains white powder crystal 21.18g.Detected through efficient liquid phase, its cane sugar-6-acetic ester content is
98.4%, concrete analysis the results are shown in Table 2.
Embodiment 6
500g sucrose and 2L DMF solutions are added in a 5L four-hole boiling flask, agitating paddle and thermometer, and band are installed
There is the condenser pipe of water knockout drum.60 DEG C are heated to, treats that sucrose dissolves, 375g Dibutyltin oxides and 1.5L hexamethylenes is added, plus
Heat to 90-95 DEG C of reflux water-dividing, 5 hour reactions terminate, are cooled to 5 DEG C, 157.5g acetic anhydrides are added dropwise, are warming up to after half an hour
Room temperature, continues to stir 4h, adds 150mL water, and vacuum distillation after stirring half an hour removes water and hexamethylene and major part DMF,
Obtain 700g reactant mixtures.
Said mixture 30g is weighed, 65 DEG C are heated to, 21mL isopropyls are added while stirring using 750 revs/min of speed
Nitrile and 5mL glycol dimethyl ethers, thing to be concentrated is all after dissolving, and white precipitate occurs in slow cooling.In -5 DEG C~0 DEG C condition
Lower standing 2h, is filtered, and drying obtains white powder crystal 21.28g.Detected through efficient liquid phase, its cane sugar-6-acetic ester contains
Measure as 97.9%, concrete analysis the results are shown in Table 2.
Embodiment 7
500g sucrose and 2L DMF solutions are added in a 5L four-hole boiling flask, agitating paddle and thermometer, and band are installed
There is the condenser pipe of water knockout drum.60 DEG C are heated to, treats that sucrose dissolves, 375g Dibutyltin oxides and 1.5L hexamethylenes is added, plus
Heat to 90-95 DEG C of reflux water-dividing, 5 hour reactions terminate, are cooled to 5 DEG C, 157.5g acetic anhydrides are added dropwise, are warming up to after half an hour
Room temperature, continues to stir 4h, adds 150mL water, and vacuum distillation after stirring half an hour removes water and hexamethylene and major part DMF,
Obtain 700g reactant mixtures.
Said mixture 100g is weighed, 80 DEG C are heated to, 40mL fourths are added while stirring using 800 revs/min of speed
Nitrile and 10mL t-butyl methyl ethers, thing to be concentrated is all after dissolving, and white precipitate occurs in slow cooling.In -5 DEG C~0 DEG C condition
Lower standing 2h, is filtered, and drying obtains white powder crystal 70.75g.Detected through efficient liquid phase, its cane sugar-6-acetic ester contains
Measure as 98.2%, concrete analysis the results are shown in Table 2.
Table 1 crystallizes preceding mix ingredients content information
Material | Remaining sugar | Monoesters impurity | Dibasic acid esters impurity | Cane sugar-6-acetic ester |
Mass percent | 3.5% | 4.8% | 5.1% | 86.6% |
Sample composition content information after the crystallization of table 2
Material | Remaining sugar | Monoesters impurity | Dibasic acid esters impurity | Cane sugar-6-acetic ester |
Example 1 | 1.11% | 0.23% | 0.08% | 98.58% |
Example 2 | 1.34% | 0.21% | 0.04% | 98.41% |
Example 3 | 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% |
Follow-up chlorination is used for the crystallized product of embodiment 7
White crystals 11.5g is weighed, is added in 500mL there-necked flask, 210mLDMF solution is added ,-15-20
Stirred at DEG C, dissolve esterification liquid mixture, be slowly added to triphosgene 48g, maintenance reaction temperature is in-15-5 DEG C of scopes
It is interior.After charging is finished, reaction 0.5h is stirred at room temperature, using temperature programming, chlorination reaction liquid is obtained.Sampling dilution, centrifugation,
Supernatant liquid carries out efficient liquid phase detection, obtained testing result such as table 3.
Comparative example 8
500g sucrose and 2L DMF solutions are added in a 5L four-hole boiling flask, agitating paddle and thermometer, and band are installed
There is the condenser pipe of water knockout drum.60 DEG C are heated to, treats that sucrose dissolves, 375g Dibutyltin oxides and 1.5L hexamethylenes is added, plus
Heat to 90-95 DEG C of reflux water-dividing, 5 hour reactions terminate, are cooled to 5 DEG C, 157.5g acetic anhydrides are added dropwise, are warming up to after half an hour
Room temperature, continues to stir 4h, adds 150mL water, and vacuum distillation after stirring half an hour removes water and hexamethylene and major part DMF,
Obtain 700g reactant mixtures.
Above-mentioned reaction liquid mixture 28g is weighed, is added in 500mL there-necked flask, 200mLDMF solution is added ,-
Stirred at 15-20 DEG C, dissolve esterification liquid mixture, be slowly added to three smooth 54g, maintenance reaction temperature is at-15-5 DEG C
In the range of.After charging is finished, reaction 0.5h is stirred at room temperature, using temperature programming, chlorination reaction liquid is obtained.Sampling dilution,
Centrifugation, supernatant liquid carries out efficient liquid phase detection, obtained testing result such as table 3.
The example 7 of table 3 and 8 chlorination Comparative results
As shown in Table 3, after using the method for crystallising processing of the present invention, the use of chlorination reagent can substantially be reduced
Amount, reduces charing phenomenon, increases chlorination yield, while the content of chlorinated impurities is reduced, with more preferable industrial application value.
Claims (10)
1. a kind of recrystallization method of cane sugar-6-acetic ester, it is characterised in that including:The sucrose obtained to sucrose esterification-
Add solvent in 6- acetate mixtures, stirring, dissolving, then through cooling, filtering, dry cane sugar-6-acetic ester, wherein described
Solvent is the mixture of nitrile solvents and ether solvent.
2. the recrystallization method of cane sugar-6-acetic ester according to claim 1, it is characterised in that described nitrile solvents
For at least one in acetonitrile, propionitrile, butyronitrile, isobutyronitrile and isopropyl nitrile.
3. the recrystallization method of cane sugar-6-acetic ester according to claim 1, it is characterised in that described ether solvent
For at least one in ether, tetrahydrofuran, glycol dimethyl ether and t-butyl methyl ether.
4. the recrystallization method of cane sugar-6-acetic ester according to claim 1, it is characterised in that described nitrile solvents
Volume ratio with ether solvent is 1:1~10:1.
5. the recrystallization method of cane sugar-6-acetic ester according to claim 1, it is characterised in that whipping temp is 40~
80℃。
6. the recrystallization method of cane sugar-6-acetic ester according to claim 1, it is characterised in that mixing speed is 400~
1000 revs/min.
7. the recrystallization method of cane sugar-6-acetic ester according to claim 1, it is characterised in that recrystallization temperature is -5
DEG C~0 DEG C.
8. the recrystallization method of cane sugar-6-acetic ester according to claim 1, it is characterised in that the recrystallization time is 1~
2h。
9. the recrystallization method of cane sugar-6-acetic ester according to claim 1, it is characterised in that described sucrose -6- second
Acid ester mixtures remove water, hexamethylene and more than 85% DMF by reaction solution and obtained.
10. a kind of preparation method of Sucralose, it is characterised in that including:
(1) sucrose carries out the cane sugar-6-acetic ester mixture that esterification is obtained;
(2) cane sugar-6-acetic ester is obtained according to the recrystallization method described in any one of claim 1~9;
(3) cane sugar-6-acetic ester carries out chlorination reaction and obtains Sucralose.
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
CN111647023A (en) * | 2020-05-22 | 2020-09-11 | 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 |
CN114437146A (en) * | 2022-01-10 | 2022-05-06 | 福州大学 | Production process of sucralose-6-acetate |
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CN1528772A (en) * | 2003-10-01 | 2004-09-15 | 常州市牛塘化工厂 | Method for preparing sucrose-6-ethyl ester |
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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CN1528772A (en) * | 2003-10-01 | 2004-09-15 | 常州市牛塘化工厂 | Method for preparing sucrose-6-ethyl ester |
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 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
CN111647023A (en) * | 2020-05-22 | 2020-09-11 | 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 |
CN114437146A (en) * | 2022-01-10 | 2022-05-06 | 福州大学 | Production process of sucralose-6-acetate |
CN114437146B (en) * | 2022-01-10 | 2023-12-08 | 福州大学 | Production process of sucralose-6-acetate |
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