CN104098617A - Preparation method of sucrose-6-acetate - Google Patents
Preparation method of sucrose-6-acetate Download PDFInfo
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- CN104098617A CN104098617A CN201310117548.XA CN201310117548A CN104098617A CN 104098617 A CN104098617 A CN 104098617A CN 201310117548 A CN201310117548 A CN 201310117548A CN 104098617 A CN104098617 A CN 104098617A
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- organic solvent
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- sucrose
- acetic ester
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 19
- 229930006000 Sucrose Natural products 0.000 claims abstract description 18
- 239000005720 sucrose Substances 0.000 claims abstract description 18
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000010992 reflux Methods 0.000 claims abstract description 13
- 150000003606 tin compounds Chemical class 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 14
- 239000003495 polar organic solvent Substances 0.000 claims description 10
- VNRQFTQKKOQJIA-UHFFFAOYSA-L [[acetyloxy(dimethyl)stannyl]oxy-dimethylstannyl] acetate Chemical compound CC(=O)O[Sn](C)(C)O[Sn](C)(C)OC(C)=O VNRQFTQKKOQJIA-UHFFFAOYSA-L 0.000 claims description 5
- MJVUVUZMCZQYLU-UHFFFAOYSA-L chloro-[chloro(dimethyl)stannyl]oxy-dimethylstannane Chemical compound C[Sn](C)(Cl)O[Sn](C)(C)Cl MJVUVUZMCZQYLU-UHFFFAOYSA-L 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- -1 methyl tertbutyl ester Chemical class 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- JLHADLTXDDGZFX-UHFFFAOYSA-L [[acetyloxy(dibutyl)stannyl]oxy-dibutylstannyl] acetate Chemical compound CCCC[Sn](CCCC)(OC(C)=O)O[Sn](CCCC)(CCCC)OC(C)=O JLHADLTXDDGZFX-UHFFFAOYSA-L 0.000 claims 1
- IJQVWOFSFLHPCW-UHFFFAOYSA-L [[benzoyloxy(dibutyl)stannyl]oxy-dibutylstannyl] benzoate Chemical compound C=1C=CC=CC=1C(=O)O[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)OC(=O)C1=CC=CC=C1 IJQVWOFSFLHPCW-UHFFFAOYSA-L 0.000 claims 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 abstract description 5
- 239000004376 Sucralose Substances 0.000 abstract description 4
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 abstract description 4
- 235000019408 sucralose Nutrition 0.000 abstract description 4
- 235000003599 food sweetener Nutrition 0.000 abstract description 3
- 239000000376 reactant Substances 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- 239000003765 sweetening agent Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 238000004064 recycling Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 208000012839 conversion disease Diseases 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 abstract 1
- 238000007670 refining Methods 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000002860 competitive effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 2
- WNVQCJNZEDLILP-UHFFFAOYSA-N dimethyl(oxo)tin Chemical class C[Sn](C)=O WNVQCJNZEDLILP-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- YQZFOYOPOPHYAI-UHFFFAOYSA-M chloro-dimethylstannyloxy-dimethylstannane Chemical compound Cl[Sn](O[SnH](C)C)(C)C YQZFOYOPOPHYAI-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical class C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000000185 sucrose group Chemical group 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
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- Saccharide Compounds (AREA)
Abstract
The invention relates to a preparation method of a key intermediate sucrose-6-acetate of novel sweetener sucralose, which specifically comprises the following process flows: (1) adding sucrose into an organic solvent N, N-dimethylformamide, heating to 80-100 ℃ for dissolution, then cooling to 70 ℃, adding a nonpolar organic solvent and an organic tin compound, refluxing and carrying out water-carrying reaction for 5-8 hours, and controlling the reflux temperature to be 80-100 ℃; (2) cooling the reactant to below 25 ℃, and then dropwise adding acetic anhydride into the reactant for reacting for 2-8 hours; (3) adding a proper amount of water into the reaction solution, extracting the organic tin compounds by using a nonpolar organic solvent, concentrating, recycling, and using the nonpolar organic solvent for azeotropy and carrying water on raffinate to obtain the sucrose-6-acetate solution. The method avoids the problems of solid treatment and low yield of the traditional organic tin process, has simple operation, low labor intensity and high reaction conversion rate, and the reaction liquid is directly used for the next chlorination reaction without refining and separation.
Description
Technical field
The present invention relates to the preparation method of the preparation method's of Chemicals, particularly a kind of New Sweetening Agent Trichlocromethyl Sucrose key intermediate cane sugar-6-acetic ester.
Background technology
Sucralose, chemical name Sucralose, first synthetic by Britain Tate & Lyte company, be that the tool of synthetic is up to now competitive, non-nutritive intensive sweetener.Synthetic full radical protection method, enzyme-chemically method and the single radical protection method of mainly containing of Sucralose; full radical protection method synthetic route is long, cost is high; enzyme-chemically method cost of investment is high, separation difficulty, and single radical protection method synthetic route is short, yield is high, is best suited for industrialized synthetic route.The core of single radical protection method is the 6-position hydroxyl that will protect in sucrose molecules, has at present two kinds of methods of trimethyl orthoacetate method and organotin method, and from low-cost, high yield, organotin method has more competitive power.
Utilize Dibutyltin oxide to carry out selective esterification reaction and have very early bibliographical information mistake, as: J.Org.Chem., 33,2684 (1968) and Tetrahedron, in 41,643 (1985), with regard to Dibutyltin oxide and hydroxy-containing compounds effect, then done detailed elaboration with process and the mechanism of aceticanhydride generation transesterification reaction.The synthetic method of US Patent No. 5023329 disclosed sucrose-6-ethyl esters is: polar organic solvent as dimethyl formamide in; by the organic solvent with water azeotropic, take the water in reaction process out of as hexanaphthene; sucrose reacts with dialkyltin and generates sucrose-organotin mixture (DBSS); react with anhydrides acylating reagent again and generate cane sugar-6-acetic ester; this operational path need to reclaim dialkyltin, exist solids treatment loaded down with trivial details, be difficult to the shortcomings such as serialization production.It is sucrose and 1,3-dialkoxy-1 that US Patent No. 4950746 discloses a kind of method, 1; the reaction of 3,3-tetraalkyl distannoxane generates 1,3-, bis-sucrose-1; 1,3,3-tetraalkyl distannoxane; then generate sucrose-6-ester with acylation reaction, this technique need to recycle 1,3-dialkoxy-1 with alkoxide equally; 1; 3,3-tetraalkyl distannoxane, operational path is loaded down with trivial details.US Patent No. 5470969 discloses and has adopted 1 in addition, 3-diacetoxy-1,1,3,3-tetrabutyldistannoxane (DSDA) is as reaction reagent, DSDA only needs desolvation just can directly apply mechanically, and technique has before been saved recycling step, but DSDA recovery yield is unstable.
Summary of the invention
The preparation method of the cane sugar-6-acetic ester that the invention provides a kind of easy to operate, high yield, can be continuously produced.
The synthetic method of described cane sugar-6-acetic ester comprises following step: (1), sucrose is joined to organic solvent N, in dinethylformamide (DMF), be heated to 80～100 ℃ of dissolvings, then be cooled to 70 ℃, add non-polar organic solvent and organic tin compound to reflux and be with water reaction 5～8 hours, reflux temperature is controlled at 80～100 ℃; (2) above-mentioned reactant is cooled to below 25 ℃, then drips wherein acetic anhydride 2～8 hours; (3) in above-mentioned reaction solution, add appropriate water, with non-polar organic solvent extraction organic tin compound, concentrated rear recovery, raffinate obtains cane sugar-6-acetic ester solution with non-polar organic solvent azeotropic band water again.
As prior art, described sucrose and the mass ratio of DMF are 1: 3～1: 8, are preferably 1: 6, and the volume ratio of non-polar organic solvent and DMF is 1: 3～1: 6.
As prior art, the mol ratio of described sucrose, organic tin compound, aceticanhydride, water is 1: 0.8～1.2: 1.0～1.2: 2～6.
As preferred version, described reflux temperature is 85～90 ℃, and the reaction times that drips aceticanhydride is 3～5 hours.
Embodiment
Below in conjunction with concrete embodiment, further set forth the present invention:
Embodiment 1, to 500mL, be equipped with in mechanical stirring, thermometer and the four-hole round-bottomed flask with the spherical condensation tube of water trap and add 32.0 grams of (0.094mol) sucrose and 180mLDMF solution, be heated to 85～90 ℃ of dissolvings, be cooled to 60 ℃ and add 38.0 grams of (0.099mol) 1,3-bis-chloro-1,1,3,3-tetramethyl-distannoxane and 50mL hexanaphthene, be heated to 90～95 ℃ of azeotropic dehydration reactions 1.5 hours, reaction finishes to be cooled to 0 ℃ and drips 10.4 grams of diacetyl oxides, within 20 minutes, is added dropwise to complete, and continues stirring reaction 3 hours; Add 5mL water, stir 30 minutes, respectively with 80mL hexanaphthene extraction three times; In reaction solution, add hexanaphthene 80mL again, reflux dewatering and other components, reflux 6 hours, finally steam again hexanaphthene, be cooled to the DMF solution that room temperature obtains cane sugar-6-acetic ester, the monoesters of efficient liquid phase chromatographic analysis cane sugar-6-acetic ester content 89.6%, residual sucrose 1.5%, other positions and polyester content 8.9%, this solution can be directly used in next step chlorination.
Embodiment 2, three secondary ring hexane extractions in example 1 are merged mutually, hexanaphthene is deviate from decompression, obtain 37.3 grams of transparent concentrated solutions, concentrated solution is 1, 3-bis-chloro-1, 1, 3, 3-tetramethyl-distannoxane, the rate of recovery can reach more than 98%, take this concentrated solution as catalyzer, repeat embodiment 1, add 0.7 gram 1 simultaneously, 3-bis-chloro-1, 1, 3, 3-tetramethyl-distannoxane, the mol ratio of fixation reaction thing, reaction can obtain the DMF solution of cane sugar-6-acetic ester, efficient liquid phase chromatographic analysis cane sugar-6-acetic ester content 88.4%, residual sucrose 1.8%, the monoesters of other positions and polyester content 9.8%, this solution can be directly used in next step chlorination.
Embodiment 3, repeat embodiment 2, continuous recycled 1, and 3-bis-is chloro-1,1,3,3-tetramethyl-distannoxane, experimental result shows that the stable content of cane sugar-6-acetic ester is more than 88%, illustrate that catalyzer can unlimitedly apply mechanically, and need add a little loss amount.
Embodiment 4,16.5 grams of (0.1mol) dimethyl tin oxides and 22.0 grams of (0.1mol) dimethyltin chlorides are added in 250mL flask, take acetone as solvent, magnetic agitation, oil bath heating reflux reaction to reaction solution is clarified, after filtered while hot, decompressing and extracting solvent obtains 32.6 grams of white solids, through ether/sherwood oil recrystallization, obtain 30.9 grams of white crystals again, this white crystal is 1,3-bis-chloro-1,1,3,3-tetramethyl-distannoxane, as the catalyzer of preparing cane sugar-6-acetic ester.
Embodiment 5, to 500mL, be equipped with in mechanical stirring, thermometer and the four-hole round-bottomed flask with the spherical condensation tube of water trap and add 32.0 grams of (0.094mol) sucrose, 180mLDMF solution, 42.5 grams of (0.098mol) 1,3-diacetoxy-1,1,3,3-tetramethyl-distannoxane and 50mL hexanaphthene, be heated to 90～95 ℃ and dissolve azeotropic dehydration reaction 3 hours, reaction finishes to be cooled to 0 ℃ and drips 9.8 grams of diacetyl oxides, within 20 minutes, is added dropwise to complete, and continues stirring reaction 3 hours; Add 5mL water, stir 30 minutes, respectively with 80mL hexanaphthene extraction three times; In reaction solution, add hexanaphthene 80mL again, reflux dewatering and other components, reflux 6 hours, finally steam again hexanaphthene, be cooled to the DMF solution that room temperature obtains cane sugar-6-acetic ester, the monoesters of efficient liquid phase chromatographic analysis cane sugar-6-acetic ester content 87.0%, residual sucrose 3.5%, other positions and polyester content 9.5%, this solution can be directly used in next step chlorination.
Embodiment 6, three secondary ring hexane extractions in example 3 are merged mutually, hexanaphthene is deviate from decompression, obtain 41.7 grams of transparent concentrated solutions, concentrated solution is 1, 3-diacetoxy-1, 1, 3, 3-tetramethyl-distannoxane, the rate of recovery is 98.1%, take this concentrated solution as catalyzer, repeat embodiment 3, add 0.8 gram 1 simultaneously, 3-diacetoxy-1, 1, 3, 3-tetramethyl-distannoxane, the mol ratio of fixation reaction thing, reaction can obtain the DMF solution of cane sugar-6-acetic ester, efficient liquid phase chromatographic analysis cane sugar-6-acetic ester content 87.3%, residual sucrose 2.1%, the monoesters of other positions and polyester content 10.6%, this solution can be directly used in next step chlorination.
Embodiment 7, repeat embodiment 5, constantly apply mechanically 1,3-diacetoxy-1,1,3,3-tetramethyl-distannoxane, and experimental result shows that the stable content of cane sugar-6-acetic ester is more than 86%, illustrate that catalyzer can unlimitedly apply mechanically, and need add a little loss amount.
Embodiment 8,16.5 grams of (0.1mol) dimethyl tin oxides and 6.0 grams of (0.1mol) Glacial acetic acid are joined in 250mL flask, take hexanaphthene as solvent, magnetic agitation, be heated to 60 ℃, question response liquid clear steams cyclohexane solvent, obtains thickness oily liquids and is 1,3-diacetoxy-1,1,3,3-tetramethyl-distannoxane, can be directly as the catalyzer of preparing cane sugar-6-acetic ester.
Claims (8)
1. the preparation method of a cane sugar-6-acetic ester, it is characterized in that described method is for to join organic solvent N by sucrose, in dinethylformamide, dissolve and add the band water reaction 5～8 hours that refluxes of non-polar organic solvent and organic tin compound after cooling, reflux temperature is controlled at 80～100 ℃, reaction solution is cooled to below 25 ℃, then drip wherein acetic anhydride 2～8 hours, in reaction solution, add appropriate water again, with non-polar organic solvent extraction organic tin compound, recovery after concentrated, raffinate obtains cane sugar-6-acetic ester solution with non-polar organic solvent azeotropic band water again.
2. the preparation method of cane sugar-6-acetic ester as claimed in claim 1, is characterized in that described non-polar organic solvent is a kind of in benzene,toluene,xylene, hexanaphthene, hexahydroaniline, methyl tertbutyl ester.
3. the preparation method of cane sugar-6-acetic ester as claimed in claim 1, is characterized in that described organic solvent DMF and the ratio of non-polar organic solvent are 8: 5～8: 1, is preferably 3: 1～6: 1.
4. the preparation method of cane sugar-6-acetic ester as claimed in claim 1, is characterized in that described organic tin compound is one of following: dibutyl carboxylic acid tin ester, 1, and 3-bis-chloro-1,1,3,3-tetrabutyldistannoxane, 1,3-diacetoxy-1,1,3,3-tetrabutyldistannoxane, 1,3-bis-chloro-1,1,3,3-tetramethyl-distannoxane, 1,3-diacetoxy-1,1,3,3-tetramethyl-distannoxane, 1,3-dibenzoyl Oxy-1,1,3,3-tetrabutyldistannoxane, be preferably 1,3-bis-chloro-1,1,3,3-tetramethyl-distannoxane.
5. the preparation method of cane sugar-6-acetic ester as claimed in claim 1, the consumption that it is characterized in that described organic tin compound is 0.5～1.5 times of sucrose molar weight, is preferably 0.8～1.2 times.
6. the preparation method of cane sugar-6-acetic ester as claimed in claim 1, is characterized in that the reflux temperature of sucrose solution and organic tin compound azeotropic band water is 80～100 ℃.
7. the preparation method of cane sugar-6-acetic ester as claimed in claim 1, the consumption that it is characterized in that described diacetyl oxide is 1.0～1.5 times of sucrose mole number, is preferably 1.0～1.2 times.
8. the preparation method of cane sugar-6-acetic ester as claimed in claim 1, the reaction times that it is characterized in that dripping after aceticanhydride is 2～8 hours, is preferably 3～5 hours.
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Cited By (10)
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| CN106349300A (en) * | 2016-08-30 | 2017-01-25 | 安徽金禾实业股份有限公司 | Method for reaction of sucralose esterified single solvent |
| CN109438533A (en) * | 2018-12-10 | 2019-03-08 | 安徽金禾实业股份有限公司 | A kind of method of Sucralose production high temperature continuous acylation |
| CN109575090A (en) * | 2018-12-10 | 2019-04-05 | 安徽金禾实业股份有限公司 | A kind of preparation method of cane sugar-6-acetic ester |
| WO2019223485A1 (en) * | 2018-05-22 | 2019-11-28 | 山东新和成精化科技有限公司 | Method for synthesizing sucrose-6-ester |
| CN112218874A (en) * | 2020-09-10 | 2021-01-12 | 安徽金禾实业股份有限公司 | Preparation method of sucrose-6-ester |
| CN112384522A (en) * | 2020-09-21 | 2021-02-19 | 安徽金禾实业股份有限公司 | Preparation method of sucrose-6-carboxylate |
| CN112996798A (en) * | 2020-12-28 | 2021-06-18 | 安徽金禾实业股份有限公司 | Chlorination method of sucrose-6-carboxylate |
| CN114133411A (en) * | 2021-11-23 | 2022-03-04 | 安徽金禾实业股份有限公司 | Method for extracting floccules from sucralose |
| WO2022246846A1 (en) * | 2021-05-28 | 2022-12-01 | 安徽金禾实业股份有限公司 | Supported organotin catalyst and preparation method for sucrose-6-carboxylate |
| WO2023000518A1 (en) * | 2021-07-23 | 2023-01-26 | 广州白云山汉方现代药业有限公司 | Method for synthesizing paeoniflorin derivative |
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