CN101157601A - Method for synthesizing 2,2-dimethoxypropane - Google Patents
Method for synthesizing 2,2-dimethoxypropane Download PDFInfo
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- CN101157601A CN101157601A CNA2007101568182A CN200710156818A CN101157601A CN 101157601 A CN101157601 A CN 101157601A CN A2007101568182 A CNA2007101568182 A CN A2007101568182A CN 200710156818 A CN200710156818 A CN 200710156818A CN 101157601 A CN101157601 A CN 101157601A
- Authority
- CN
- China
- Prior art keywords
- reaction
- acetone
- dimethyl acetal
- propanal dimethyl
- trimethyl orthoformate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 230000000694 effects Effects 0.000 claims abstract description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 34
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical group [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- 238000010189 synthetic method Methods 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 6
- 238000006386 neutralization reaction Methods 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 3
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 238000012545 processing Methods 0.000 claims description 2
- 238000000066 reactive distillation Methods 0.000 abstract description 2
- 238000004821 distillation Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000012423 maintenance Methods 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- -1 hydrosulfate Chemical compound 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- JXJIQCXXJGRKRJ-KOOBJXAQSA-N pseudoionone Chemical compound CC(C)=CCC\C(C)=C\C=C\C(C)=O JXJIQCXXJGRKRJ-KOOBJXAQSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
Classifications
-
- 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
- Y02P20/10—Process efficiency
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for synthesizing 2, 2-dimethyoxypropane. Under the effect of catalyst, acetone and trimethyl orthofomate are synthesized through reactive distillation; and the invention has the feeding mol ratio that the proportion between the acetone and the trimethyl orthofomate is 1:10 to 10:1. The reaction utilizes the dynamics balance principle, and continuously transforms a product in the reaction process by a reaction distillation device, to lead the reaction to go along the direction of producing. The method, realizing high conversion, has the advantages of simple device and small corrosivity as well as being easy for large-scale producing and environment-friendly.
Description
Technical field
The present invention relates to a kind of 2, the synthetic method of 2-Propanal dimethyl acetal.
Background technology
2; 2-Propanal dimethyl acetal (English name 2; 2-dimethoxy propane; be called for short DMP); in the development of fine chemical products such as medicine, agricultural chemicals, natural product and industrial production, has purposes widely; it is methoxyl group propylene, citrylideneacetone, and the key intermediate of medicine such as jononeionone, different vegetable alcohol, vitamin A, vitamin-E, chemical industry, feeds product can be used as the composition of cyclizing agent, condensing agent, dewatering agent, protective material and superpolymer catalyzer etc.
The synthetic method that DMP is traditional has acetone and methyl alcohol direct synthesis technique and indirect method synthesis method, above-mentioned two kinds of method complex process, facility investment is bigger, long reaction time, yield is low, methyl alcohol and product azeotropic, the catalyzer that the more difficult .DMP building-up reactions of the separation and purification of product is traditional is sulfuric acid, hydrochloric acid etc., but because corrodibility is strong, reason such as environmental pollution is serious makes its application receive restriction.Calendar year 2001 Yang Shumin etc. reported with acetone and trimethyl orthoformate synthetic DMP under the effect of solid acid, but since solid acid prepare loaded down with trivial details, to equipment corrosion by force, cost is also high, makes its application be subjected to certain restriction.And patent report under storng-acid cation exchange resin, synthesize DMP with acetone and trimethyl orthoformate direct reaction.We test and data shows, acetone and trimethyl orthoformate are balanced reactions, under the system of relative closure, even excessive 10 times of the amount of acetone, the transformation efficiency of trimethyl orthoformate also has only about 70%, and under the temperature as the post-reaction treatment of this patent statement, product D MP can decompose and produces many by products this also makes its yield greatly reduce, and is difficult to reach the yield in the document.
Summary of the invention
The purpose of this invention is to provide a kind ofly 2, the synthetic method of 2-Propanal dimethyl acetal is to be starting raw material with acetone and trimethyl orthoformate, under the tart catalyzer, and controlled temperature, pressure, the method by reactive distillation is synthesized into.
The technical solution used in the present invention is:
Acetone and trimethyl orthoformate are packed in the reactor, and under the effect of catalyzer, controlled temperature is-10～60 ℃, is synthesized into by reaction rectification method; Its molar ratio is that the ratio of acetone and trimethyl orthoformate is 1: 10～10: 1.
Described catalyzer is ammonium chloride, dihydrogen phosphate, hydrosulfate, hydrosulphite, sulfonic acid resin or tosic acid, and the mol ratio of catalyzer and acetone is 0.005: 1～0.3: 1.
The reaction of acetone and trimethyl orthoformate generates 2, in 2-Propanal dimethyl acetal and the methyl-formiate reaction system, adopts the method for rectifying, constantly removes lower boiling methyl-formiate and balanced reaction is moved to the direction of producing product.
After reaction was finished, after first filtering recovering catalyst or the catalyst neutralisation, remaining material carried out the processing mode of rectifying again, and temperature is controlled at-10～60 ℃ in the reactor, and pressure remains on 0.5mmHg～50mmHg, and rectifying obtains product.
An acidic catalyst with cheapness, take reaction and rectification device, produce in the reaction system of methyl-formiate and DMP at acetone and trimethyl orthoformate reaction, constantly remove lower boiling methyl-formiate, so that react completely, thereby high yield obtain DMP, obtained important chemical intermediate methyl-formiate simultaneously.Reaction equation is as follows:
Acetone and trimethyl orthoformate molar ratio bifurcation 1: 10～10: 1, desirable molar ratio 0.8: 1～1.2: 1, ammonium chloride, dihydrogen phosphate, hydrosulfate, hydrosulphite, sulfonic resin, tosic acid, etc. under an acidic catalyst, controlled temperature is preferably in 10～40 ℃ at-10～60 ℃, utilizes the kinetic balance principle, by adding thermal rectification, the methyl-formiate that constantly produces is collected in the circulation cooling, helps to reduce the loss of lower boiling methyl-formiate like this.Trimethyl orthoformate is by being added drop-wise in the reaction flask, and this process is the reaction of a heat release, according to the situation of heat release, the speed that control drips, dripping generally needs 1～2h. reaction by vapor detection, with the amount of acetone not till changing.After reaction finishes, filtering catalyst or catalyst neutralisation, rectifying.Rectifying need be under certain pressure, and temperature in the controlling reactor is collected product.Controlled temperature is because the product poor heat stability is decomposed polymerization easily under acidity or pyritous situation.
The beneficial effect that the present invention has is:
1) utilizes the kinetic balance principle,, in reaction process, constantly migrate out a kind of resultant, reaction is carried out to the direction of producing product, realize high transformation efficiency by this method by reaction and rectification device.
2) equipment requirements is simple, is easy to mass-producing.
3) corrodibility is little, and is environmentally friendly.
Embodiment
Embodiment 1:
Take reactor band rectifier unit, in reactor, add agent of 20g Catalyzed by p-Toluenesulfonic Acid and 500mL acetone, start stirring, drip trimethyl orthoformate 825mL, controlled temperature is at 30～40 ℃, the overhead collection methyl-formiate reacted 3～4 hours, reaction solution add in the yellow soda ash and after, rectification under vacuum (30mmHg), temperature is at 30～35 ℃ in the maintenance reactor, and circulating frozen medium cooling cut is collected DMP, product content＞95%, yield 85～92%.
Embodiment 2:
Take reactor band rectifier unit, in reactor, add 30g catalyzer Potassium hydrogen sulfite and 700mL acetone, start stirring, drip trimethyl orthoformate 120mL, the controlling reactor temperature is at 10～15 ℃, control pressure (50mmHg), methyl-formiate is collected in the cooling of cat head circulating frozen medium, reacts 7～8 hours, filters out catalyzer, filtrate adds the yellow soda ash neutralization, rectification under vacuum (25mHg), temperature is at 25～30 ℃ in the maintenance reactor, and the circulating frozen medium cools off cut, thing and product D MP boil in the collection, in the thing that boils can apply mechanically product D MP content＞95%, yield 85～90%.
Embodiment 3:
Take 1 same apparatus, must operate the acetone of 15g catalyzer ammonium chloride and 75mL with identical with embodiment, drip trimethyl orthoformate 1000mL, the controlling reactor temperature is at 30～40 ℃, the overhead collection methyl-formiate, reaction 3～4h, filtering catalyst, filtrate neutralizes with yellow soda ash, rectification under vacuum (40mmHg), temperature is at 35～40 ℃ in the maintenance reactor, product D MP is collected in the cooling of circulating frozen medium, and substrate is recycled.Product D MP content＞95%, yield 85～92%
Embodiment 4:
Take reaction unit, apply mechanically ingredient proportion, make catalyzer, 50～60 ℃ of controlled temperature, reaction 3～4h, overhead collection methyl-formiate with the potassium primary phosphate of 25g with example 1 with embodiment 1.Filtering catalyst, filtrate add the yellow soda ash neutralization, rectification under vacuum (50mmHg), and temperature is at 55～60 ℃ in the maintenance reactor, and last yield gets 75～80%.
Embodiment 5:
Apply mechanically the ingredient proportion with example 1, make catalyzer with the tosic acid resin of 5g, react in band rectifier unit reactor, controlled temperature is-5～-10 ℃ of collections, and control pressure is at 5mmHg, and methyl-formiate is collected in the cooling of circulating frozen medium, reacts 10～12 hours.Filtering catalyst, filtrate add the yellow soda ash neutralization, rectification under vacuum (2mmHg), and temperature is at-5～-10 ℃ in the maintenance reactor, and product is collected in the cooling of circulating frozen medium, and last yield gets 85～90%.Catalyst recovery is utilized.
Claims (4)
1. one kind 2, the synthetic method of 2-Propanal dimethyl acetal is characterized in that: acetone and trimethyl orthoformate are packed in the reactor, and under the effect of catalyzer, controlled temperature is-10～60 ℃, is synthesized into by reaction rectification method; Its molar ratio is that the ratio of acetone and trimethyl orthoformate is 1: 10～10: 1.
2. according to claim 1 a kind of 2, the synthetic method of 2-Propanal dimethyl acetal, it is characterized in that: described catalyzer is ammonium chloride, dihydrogen phosphate, hydrosulfate, hydrosulphite, sulfonic acid resin or tosic acid, and the mol ratio of catalyzer and acetone is 0.005: 1～0.3: 1.
3. according to claim 1 a kind of 2, the synthetic method of 2-Propanal dimethyl acetal, it is characterized in that: acetone and trimethyl orthoformate reaction generate 2, in 2-Propanal dimethyl acetal and the methyl-formiate reaction system, adopt the method for rectifying, constantly remove lower boiling methyl-formiate and balanced reaction is moved to the direction of producing product.
4. according to claim 1 a kind of 2, the synthetic method of 2-Propanal dimethyl acetal, it is characterized in that: after reaction is finished, after elder generation's filtering recovering catalyst or the catalyst neutralisation, remaining material carries out the processing mode of rectifying again, temperature is controlled at-10～60 ℃ in the reactor, and pressure remains on 0.5mmHg～50mmHg, and rectifying obtains product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007101568182A CN101157601A (en) | 2007-11-12 | 2007-11-12 | Method for synthesizing 2,2-dimethoxypropane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007101568182A CN101157601A (en) | 2007-11-12 | 2007-11-12 | Method for synthesizing 2,2-dimethoxypropane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101157601A true CN101157601A (en) | 2008-04-09 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007101568182A Pending CN101157601A (en) | 2007-11-12 | 2007-11-12 | Method for synthesizing 2,2-dimethoxypropane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101157601A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103360438A (en) * | 2013-07-30 | 2013-10-23 | 济南卡博唐生物科技有限公司 | Preparation method of bispropylidenesulfoglucoside compound |
-
2007
- 2007-11-12 CN CNA2007101568182A patent/CN101157601A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103360438A (en) * | 2013-07-30 | 2013-10-23 | 济南卡博唐生物科技有限公司 | Preparation method of bispropylidenesulfoglucoside compound |
| CN103360438B (en) * | 2013-07-30 | 2016-08-10 | 济南尚博生物科技有限公司 | A kind of preparation method of pair of propylidene thio glycoside compound |
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Open date: 20080409 |