CN108752309A - A kind of method of catalysis oxidation synthetic glycerine aldehyde contracting acetone - Google Patents
A kind of method of catalysis oxidation synthetic glycerine aldehyde contracting acetone Download PDFInfo
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- CN108752309A CN108752309A CN201810472193.9A CN201810472193A CN108752309A CN 108752309 A CN108752309 A CN 108752309A CN 201810472193 A CN201810472193 A CN 201810472193A CN 108752309 A CN108752309 A CN 108752309A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/057—Selenium or tellurium; Compounds thereof
- B01J27/0573—Selenium; Compounds thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
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Abstract
The present invention relates to a kind of methods of catalysis oxidation synthetic glycerine aldehyde contracting acetone, specifically comprise the following steps：Glyceryl alcohol contracting acetone is dissolved in acetone, suitable fullerene zinc oxide selenium (C is added60/ ZnO/Se) composite material, at room temperature, be passed through oxygen reaction, until reaction solution in without glyceryl alcohol contracting acetone, be centrifuged off fullerene zinc oxide selenium (C60/ ZnO/Se) composite material, supernatant is through being concentrated under reduced pressure, being drying to obtain glyceraldehyde acetonide.
Description
Technical field
The invention belongs to organic synthesis and catalytic fields, and in particular to a kind of side of catalysis oxidation synthetic glycerine aldehyde contracting acetone
Method.
Background technology
Glyceraldehyde is a kind of optical activity aldose compound found earliest, contains a pair of of asymmetric carbon atom, i.e. D in molecule
Type and L-type optical isomer, are commonly used for the standard of calibration carbohydrate configuration.Racemic modification D, L- glyceraldehyde has anti-sugared ferment
Solution acts on, and is a kind of good Preservative of blood glucose, while as a kind of important organic synthesis intermediate, in medicine, chemurgy
Occupy considerable status in product and natural products synthesis, chiral source can be used as to carry out asymmetric conjunction in organic synthesis
At especially it contains active functional group-aldehyde radical, can generate a plurality of types of derivatives, therefore opening in chiral drug
It is had a very important significance in hair.In food medicine and chemical industry, mainly as a kind of cheap chiral induction monomer
It is used for synthesizing the important as precursors of some chiral drugs and natural products with optical activation for the synthesis of chiral molecules.
The conventional production methods of glyceraldehyde, by chemical oxidization method synthetic glycerine aldehyde, are commonly used mainly using glycerine as raw material
Oxidant be generally：Hydrogen peroxide, peroxy acid, dust technology, chromium oxide, activated manganese dioxide, dimethyl sulfoxide etc. are as oxidation
Agent prepares glyceraldehyde.But the problems such as hydrogen peroxide, peroxy acid etc. are strong oxidizer, inflammable, explosive, and there are transport, storages,
The environmental pollutions such as chromium oxide, dimethyl sulfoxide, therefore seek high efficiency, low cost, environment amenable new preparation process
It is still the important goal of current research.Reaction equation is as follows：
[O]=H2O2,ROOOH,HNO3, Collins reagents, Pcc, MnO2,DMSO……
There is the anhydrous ZnCl of document report Lewis acid2As catalytic dehydrating agent, PEARLITOL 25C reacts synthesis with condensation of acetone
Diisopropylidene condensation product, then uses NaIO4It aoxidizes scission of link and prepares D- (R)-glyceraldehyde acetonide, then slough acetone and prepare glycerine
Aldehyde.This method high, inexpensive, advantages of environment protection with yield.But it is lacked since cost of material is higher, reaction step is complicated etc.
Point is unsuitable for industrialized production selection.Reaction is as follows：
Also document report uses Synthesis of Glyceraldehydes by Indirect Electro-oxidation by raw material of glycerine, although there is the method reaction to walk
The features such as rapid simple, product yield is high, but energy consumption is larger in reaction, and need UF membrane etc., it is also not suitable for industrialized production.This
Invention overcome the deficiencies in the prior art develops a kind of fullerene zinc oxide selenium (C60/ ZnO/Se) composite material as catalyst,
Catalyzing glycerol, glyceryl alcohol contracting acetone in the presence of oxygen, are leniently converted into glyceraldehyde, glyceraldehyde acetonide, the operation
Simplicity, mild condition, conversion ratio and high selectivity, it is environmentally safe, environmentally protective, be easy to industrialized production.
Invention content
The present invention provides a kind of fullerene zinc oxide selenium (C60/ ZnO/Se) composite material, it is characterised in that the fullerene
The preparation method of zinc oxide selenium composite material includes the following steps：
(1) after mixing by fullerene, zinc solution, ammonium hydroxide, natural after being warming up to 120-130 DEG C of reaction 18-20h
It is cooled to room temperature, it is post-treated to obtain fullerene zinc oxide (C60/ ZnO) material；
(2) the fullerene zinc oxide (C for obtaining step (1)60/ ZnO) material be added volume fraction be 5%-10% second
After stirring 10-15min in alcoholic solution, the hydrazine hydrate containing selenium is added, continues after stirring 10-15min, is warming up to 160-180 DEG C instead
After answering 12-16h, cooled to room temperature is post-treated up to the fullerene zinc oxide selenium (C60/ ZnO/Se) composite material.
Every gram of fullerene uses zinc salt 2-3mmol in step (1), and the molar ratio of zinc salt and ammonium hydroxide is 1：1.2-1.5, zinc salt
A concentration of 1-2mol/L of solution, a concentration of 1mol/L of ammonium hydroxide；The preferred C of fullerene60、C70One or both of it is mixed
It closes；The zinc salt is selected from one or more of zinc chloride, zinc nitrate, zinc sulfate or its hydrate.
Every gram of fullerene zinc oxide (C in step (2)60/ ZnO) materials'use ethanol solution 120-180mL, using containing selenium
Hydrazine hydrate 10-15mL；The hydrazine hydrate containing selenium is 6-10mg containing selenium in every milliliter of hydrazine hydrate.
The reaction of step (1), (2) of the present invention carries out preferably in autoclave；Place after step (1), (2) are described
After reason is filtering, precipitation deionized water, ethyl alcohol wash, 6-10h is dried in vacuo at 60-80 DEG C.
Another embodiment of the present invention provides a kind of fullerene zinc oxide selenium (C60/ ZnO/Se) composite material preparation side
Method, it is characterised in that include the following steps：
(1) after mixing by fullerene, zinc solution, ammonium hydroxide, natural after being warming up to 120-130 DEG C of reaction 18-20h
It is cooled to room temperature, it is post-treated to obtain fullerene zinc oxide (C60/ ZnO) material；
(2) the fullerene zinc oxide (C for obtaining step (1)60/ ZnO) material be added volume fraction be 5%-10% second
After stirring 10-15min in alcoholic solution, the hydrazine hydrate containing selenium is added, continues after stirring 10-15min, is warming up to 160-180 DEG C instead
After answering 12-16h, cooled to room temperature is post-treated up to the fullerene zinc oxide selenium (C60/ ZnO/Se) composite material.
Every gram of fullerene uses zinc salt 2-3mmol in step (1), and the molar ratio of zinc salt and ammonium hydroxide is 1：1.2-1.5, zinc salt
A concentration of 1-2mol/L of solution, a concentration of 1mol/L of ammonium hydroxide；The preferred C of fullerene60、C70One or both of it is mixed
It closes；The zinc salt is selected from one or more of zinc chloride, zinc nitrate, zinc sulfate or its hydrate.
Every gram of fullerene zinc oxide (C in step (2)60/ ZnO) materials'use ethanol solution 120-180mL, using containing selenium
Hydrazine hydrate 10-15mL；The hydrazine hydrate containing selenium is 6-10mg containing selenium in every milliliter of hydrazine hydrate.
The reaction of step (1), (2) of the present invention carries out preferably in autoclave；Place after step (1), (2) are described
After reason is filtering, precipitation deionized water, ethyl alcohol wash, 6-10h is dried in vacuo at 60-80 DEG C.
Another embodiment of the present invention provides above-mentioned fullerene zinc oxide selenium (C60/ ZnO/Se) composite material conduct catalysis
The application of agent, preferably as the application of oxidation reaction catalyst.
Another embodiment of the present invention provides above-mentioned fullerene zinc oxide selenium (C60/ ZnO/Se) composite material is in selectivity
Aoxidize the application in primary hydroxyl, the preferably application in selective oxidation primary hydroxyl is aldehyde radical.
Another embodiment of the present invention provides above-mentioned fullerene zinc oxide selenium (C60/ ZnO/Se) composite material prepare it is sweet
Application in oily aldehyde.
Another embodiment of the present invention provides above-mentioned fullerene zinc oxide selenium (C60/ ZnO/Se) composite material catalysis oxygen
Change glycerine and prepares the application in glyceraldehyde.
Another embodiment of the present invention provides above-mentioned fullerene zinc oxide selenium (C60/ ZnO/Se) composite material prepare it is sweet
Application in oily aldehyde contracting acetone.
Another embodiment of the present invention provides above-mentioned fullerene zinc oxide selenium (C60/ ZnO/Se) composite material catalysis oxygen
Change glyceryl alcohol contracting acetone and prepares the application in glyceraldehyde acetonide.
Another embodiment of the present invention provides a kind of preparation method of glyceraldehyde, it is characterised in that includes the following steps：
Suitable above-mentioned fullerene zinc oxide selenium (C is added into glycerine water solution60/ ZnO/Se) composite material, it is warming up to
After 45-50 DEG C, it is passed through oxygen, after reacting 5-8 hours, is centrifuged off fullerene zinc oxide selenium (C60/ ZnO/Se) composite material, on
Clear liquid is added absolute ethyl alcohol crystallization, is filtered, washed, is drying to obtain glyceraldehyde after vacuum distillation removes water.
Wherein, a concentration of 0.4-0.6mol/L of glycerine water solution, fullerene zinc oxide selenium (C60/ ZnO/Se) composite material
Dosage be per mole of glycerin use 40-50mg fullerene zinc oxide selenium (C60/ ZnO/Se) composite material；The flow velocity of oxygen is
120-150mL/min。
In above-mentioned preparation method, the yield of glyceraldehyde is 90% or more.
Another technical solution of the present invention provides a kind of preparation method of glyceraldehyde acetonide, it is characterised in that including as follows
Step：
Glyceryl alcohol contracting acetone is dissolved in acetone, suitable above-mentioned fullerene zinc oxide selenium (C is added60/ ZnO/Se) composite wood
Material is passed through oxygen reaction at room temperature, until being centrifuged off fullerene zinc oxide selenium (C without glyceryl alcohol contracting acetone in reaction solution60/
ZnO/Se) composite material, supernatant is through being concentrated under reduced pressure, being drying to obtain glyceraldehyde acetonide.
Wherein, fullerene zinc oxide selenium (C60/ ZnO/Se) dosage of composite material is use per mole of glycerin alcohol contracting acetone
25-30mg fullerene zinc oxide selenium (C60/ ZnO/Se) composite material；The flow velocity of oxygen is 180-200mL/min.The dosage of acetone
It is advisable so that reactant can be mixed well, preferably uses 1.5-2.0L acetone per mole of glycerin alcohol contracting acetone.
The above-mentioned reaction for preparing glyceraldehyde acetonide is green reaction, and (reaction time, preferred 20-24 was small after reaction
When) without complicated purification process, only it need to remove catalysts --- fullerene zinc oxide selenium (C by centrifugation60/ZnO/Se)
Composite material, supernatant concentration, drying can be obtained high-purity glycerol aldehyde contracting acetone (HPLC purity is 98.6% or more).
The advantage of the invention is that：Overcome the deficiencies in the prior art of the present invention develops a kind of fullerene zinc oxide selenium
(C60/ ZnO/Se) as catalyst, catalyzing glycerol, glyceryl alcohol contracting acetone in the presence of oxygen, are leniently converted into composite material
Glyceraldehyde, glyceraldehyde acetonide are operation simplicity, mild condition, conversion ratio and the high selectivity, environmentally safe, green
Colour circle is protected, is easy to industrialized production.
Description of the drawings
Fig. 1 present invention prepares the easy reaction installation drawing of glyceraldehyde；
The SEM of Fig. 2 products A, B scheme.
Specific implementation mode
For the ease of a further understanding of the present invention, examples provided below has done more detailed description to it.But
It is that these embodiments are only not supposed to be a limitation to the present invention or implementation principle for being better understood from invention, reality of the invention
The mode of applying is not limited to the following contents.
Embodiment 1
(1) C is taken60Fullerene (1.0g), the zinc nitrate solution (2mL) of 1mol/L, 1mol/L ammonium hydroxide (2.4mL) in high pressure
In kettle after mixing, it after being warming up to 120-125 DEG C of reaction 20h, is cooled to room temperature, filters, precipitation deionized water, second naturally
After alcohol washing, vacuum drying 6h obtains fullerene zinc oxide (C at 80 DEG C60/ ZnO) material (hereinafter referred to as product a)；
(2) product a (1.0g) is taken to be added in the ethanol solution (120mL) that volume fraction is 10% after stirring 10-15min,
The hydrazine hydrate (15mL contains selenium 150mg) containing selenium is added, continues after stirring 10-15min, after being warming up to 175-180 DEG C of reaction 12h,
Cooled to room temperature after filtering, precipitation deionized water, ethyl alcohol wash, is dried in vacuo 10h up to the fowler at 70 DEG C
Alkene zinc oxide selenium (C60/ ZnO/Se) composite material (hereinafter referred to as product A).
Embodiment 2
(1) C is taken70Fullerene (1.0g), the solution of zinc sulfate (1.5mL) of 2mol/L, 1mol/L ammonium hydroxide (4.5mL) in height
Press kettle in after mixing, be warming up to 125-130 DEG C reaction 18h after, be cooled to room temperature naturally, filter, precipitation deionized water,
After ethyl alcohol washing, vacuum drying 10h obtains fullerene zinc oxide (C at 60 DEG C70/ ZnO) material (hereinafter referred to as product b)；
(2) it takes product b (1.0g) to be added in the ethanol solution (180mL) that volume fraction is 5% after stirring 10-15min, adds
Enter the hydrazine hydrate (10mL contains selenium 60mg) containing selenium, continues after stirring 10-15min, after being warming up to 160-165 DEG C of reaction 16h, from
It is so cooled to room temperature, filters, after precipitation deionized water, ethyl alcohol wash, 6h is dried in vacuo at 80 DEG C up to the fullerene
Zinc oxide selenium (C70/ ZnO/Se) composite material (hereinafter referred to as product B).
Embodiment 3
(1) take the ammonium hydroxide (2.4mL) of graphene (1.0g), the zinc nitrate solution (2mL) of 1mol/L, 1mol/L in autoclave
In after mixing, be warming up to 120-125 DEG C reaction 20h after, be cooled to room temperature, filter, precipitation deionized water, ethyl alcohol naturally
After washing, vacuum drying 6h obtains graphene zinc oxide material (hereinafter referred to as product c) at 80 DEG C；
(2) product c (1.0g) is taken to be added in the ethanol solution (120mL) that volume fraction is 10% after stirring 10-15min,
The hydrazine hydrate (15mL contains selenium 150mg) containing selenium is added, continues after stirring 10-15min, after being warming up to 175-180 DEG C of reaction 12h,
Cooled to room temperature after filtering, precipitation deionized water, ethyl alcohol washs, 10h is dried in vacuo at 70 DEG C and obtains graphene oxidation
Zinc selenium composite material (hereinafter referred to as products C).
Embodiment 4
It takes zinc oxide (1.0g) to be added in the ethanol solution (120mL) that volume fraction is 10% after stirring 10-15min, adds
Enter the hydrazine hydrate (15mL contains selenium 150mg) containing selenium, continues after stirring 10-15min, after being warming up to 175-180 DEG C of reaction 12h, from
It is so cooled to room temperature, filters, after precipitation deionized water, ethyl alcohol wash, 10h is dried in vacuo at 70 DEG C and obtains product D.
Embodiment 5
To product A (8mg) is added in glycerine water solution (0.4mol/L, 500mL), after being warming up to 45-50 DEG C, it is passed through oxygen
(flow velocity 150mL/min) after reacting 5 hours, is centrifuged off product A, and anhydrous second is added after vacuum distillation removes water in supernatant
Alcohol crystallizes, and is filtered, washed, is drying to obtain glyceraldehyde (16.4g, yield 91.0%), structural identification data and known report one
It causes.
Embodiment 6
To product B (15mg) is added in glycerine water solution (0.6mol/L, 500mL), after being warming up to 45-50 DEG C, it is passed through oxygen
Gas (flow velocity 120mL/min) after reacting 8 hours, is centrifuged off product B, and supernatant is added anhydrous after vacuum distillation removes water
Alcohol crystal is filtered, washed, is drying to obtain glyceraldehyde (24.4g, yield 90.2%), structural identification data and known report
Unanimously.
Embodiment 7
According to the method that embodiment 5 is recorded, product a, b, c, C, D substitute products A is respectively adopted, reaction takes after 5 hours
Clear liquid carries out quantitative analysis, chromatographic condition using high performance liquid chromatography by external standard method：Using Aminex HPX-87H chromatographies
Column, 60 DEG C of column temperature, with the H of 0.01mol/L2SO4Solution is as mobile phase, flow velocity 0.5mL/min, UV detector (UVD) and shows
Poor refraction detector (RID) is used in series.The result shows that only detecting 15% glycerine in the reaction supernatant using products C
Aldehyde, 13% C3H6O3；Using glycerine is only detected in the reaction supernatant of product a, b, c, D, glycerine is not found
Aldehyde.
Embodiment 8
Glyceryl alcohol contracting acetone (0.1mol) is dissolved in addition product A (2.5mg) in acetone (150mL) and is passed through oxygen at room temperature
Solid/liquid/gas reactions (flow velocity 200mL/min), until being centrifuged off product without glyceryl alcohol contracting acetone (reaction about 24 hours) in reaction solution
A, through being concentrated under reduced pressure, being drying to obtain glyceraldehyde acetonide, (12.9g, HPLC purity are 98.6%) structural identification data to supernatant
It is consistent with known report.
Embodiment 9
Glyceryl alcohol contracting acetone (0.1mol) is dissolved in addition product B (3mg) in acetone (200mL) and is passed through oxygen at room temperature
It reacts (flow velocity 180mL/min), until it is centrifuged off product B without glyceryl alcohol contracting acetone (reaction about 20 hours) in reaction solution,
Supernatant through be concentrated under reduced pressure, be drying to obtain glyceraldehyde acetonide (12.8g, HPLC purity be 98.8%), structural identification data with
Known report is consistent.
Embodiment 10
According to the method that embodiment 8 is recorded, product a, b, c, C, D substitute products A is respectively adopted, reaction takes after 24 hours
Clear liquid carries out quantitative analysis, as a result, it has been found that using the reaction supernatant of product a, b, c, D using high performance liquid chromatography by external standard method
Glyceraldehyde acetonide is not detected in liquid, using detecting glyceraldehyde acetonide in the reaction supernatant of products C, but still has big
Measure glyceryl alcohol contracting acetone unreacted.
Claims (7)
1. a kind of preparation method of glyceraldehyde acetonide, it is characterised in that include the following steps：
Glyceryl alcohol contracting acetone is dissolved in acetone, suitable fullerene zinc oxide selenium (C is added60/ ZnO/Se) composite material, room temperature
Under, it is passed through oxygen reaction, until being centrifuged off fullerene zinc oxide selenium (C without glyceryl alcohol contracting acetone in reaction solution60/ZnO/Se)
Composite material, supernatant is through being concentrated under reduced pressure, being drying to obtain glyceraldehyde acetonide.
2. preparation method described in claim 1, it is characterised in that the fullerene zinc oxide selenium (C60/ ZnO/Se) composite material
Dosage be that 25-30mg fullerene zinc oxide selenium (C is used per mole of glycerin alcohol contracting acetone60/ ZnO/Se) composite material.
3. claim 1-2 any one of them preparation methods, it is characterised in that the flow velocity of oxygen is 180-200mL/min.
4. claim 1-3 any one of them preparation methods, it is characterised in that per mole of glycerin alcohol contracting acetone it is preferable to use
1.5-2.0L acetone.
5. claim 1-4 any one of them preparation methods, it is characterised in that the fullerene zinc oxide selenium (C60/ZnO/Se)
The preparation method of composite material includes the following steps：
(1) after mixing by fullerene, zinc solution, ammonium hydroxide, it after being warming up to 120-130 DEG C of reaction 18-20h, is down to naturally
It is post-treated to obtain fullerene zinc oxide (C after room temperature60/ ZnO) material；
(2) the fullerene zinc oxide (C for obtaining step (1)60/ ZnO) material be added volume fraction be 5%-10% ethyl alcohol it is molten
After stirring 10-15min in liquid, the hydrazine hydrate containing selenium is added, continues after stirring 10-15min, is warming up to 160-180 DEG C of reaction 12-
After 16h, cooled to room temperature is post-treated up to the fullerene zinc oxide selenium (C60/ ZnO/Se) composite material.
6. fullerene zinc oxide selenium (C prepared by the preparation method described in claim 560/ ZnO/Se) composite material prepare it is sweet
Application in oily aldehyde contracting acetone.
7. fullerene zinc oxide selenium (C prepared by the preparation method described in claim 560/ ZnO/Se) composite material catalysis oxygen
Change glyceryl alcohol contracting acetone and prepares the application in glyceraldehyde acetonide.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1875014A (en) * | 2003-10-28 | 2006-12-06 | 帝斯曼知识产权资产管理有限公司 | Process for the preparation of glyceraldehyde acetonide |
| CN104829584A (en) * | 2015-05-19 | 2015-08-12 | 江苏福瑞生物医药有限公司 | Synthesis method of (R)-glyceraldehyde acetonide compound |
| WO2016026132A1 (en) * | 2014-08-22 | 2016-02-25 | Rhodia Operations | Process for oxidation of alcohols |
| CN106466613A (en) * | 2016-08-15 | 2017-03-01 | 青岛科技大学 | A kind of copper-zinc-tin-selenium graphene oxide photocatalysis adsorbing material and preparation method thereof |
-
2018
- 2018-05-16 CN CN201810472193.9A patent/CN108752309B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1875014A (en) * | 2003-10-28 | 2006-12-06 | 帝斯曼知识产权资产管理有限公司 | Process for the preparation of glyceraldehyde acetonide |
| WO2016026132A1 (en) * | 2014-08-22 | 2016-02-25 | Rhodia Operations | Process for oxidation of alcohols |
| CN104829584A (en) * | 2015-05-19 | 2015-08-12 | 江苏福瑞生物医药有限公司 | Synthesis method of (R)-glyceraldehyde acetonide compound |
| CN106466613A (en) * | 2016-08-15 | 2017-03-01 | 青岛科技大学 | A kind of copper-zinc-tin-selenium graphene oxide photocatalysis adsorbing material and preparation method thereof |
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