CN108752309B - Method for synthesizing glyceraldehyde acetonide through catalytic oxidation - Google Patents

Method for synthesizing glyceraldehyde acetonide through catalytic oxidation Download PDF

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CN108752309B
CN108752309B CN201810472193.9A CN201810472193A CN108752309B CN 108752309 B CN108752309 B CN 108752309B CN 201810472193 A CN201810472193 A CN 201810472193A CN 108752309 B CN108752309 B CN 108752309B
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fullerene
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陈柯全
刘伟
罗志臣
左志芳
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Yangzhou Polytechnic Institute
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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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    • 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
    • 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 invention relates to a method for synthesizing glyceraldehyde acetonide by catalytic oxidation, which comprises the following steps: dissolving glycerol acetonide in acetone, and adding appropriate amount of fullerene zinc oxide selenium (C)60Introducing oxygen to react at room temperature until glycerol acetonide is absent in the reaction solution, and centrifuging to remove fullerene zinc oxide selenium (C)60ZnO/Se) composite material, and concentrating and drying the supernatant fluid under reduced pressure to obtain the glyceraldehyde acetonide.

Description

Method for synthesizing glyceraldehyde acetonide through catalytic oxidation
Technical Field
The invention belongs to the field of organic synthesis and catalysis, and particularly relates to a method for synthesizing glyceraldehyde acetonide by catalytic oxidation.
Background
Glyceraldehyde is the first optically active aldose compound found, and the molecule contains a pair of chiral carbon atoms, i.e. D-type and L-type optical isomers, and is commonly used as the standard for calibrating the configuration of carbohydrate. The racemate D, L-glyceraldehyde has the glycolysis resistance, is a good blood sugar protective agent, is an important organic synthesis intermediate, plays a very important role in the synthesis of medicines, agricultural chemicals and natural products, can be used as a chiral source for asymmetric synthesis in organic synthesis, particularly contains active functional groups, namely aldehyde groups, and can generate various derivatives, thereby having very important significance in the development of chiral medicines. In the food, medicine and chemical industry, the chiral compound is mainly used as an inexpensive chiral inducing monomer for synthesizing chiral molecules to synthesize some chiral drugs and important precursors of natural products with optical activity.
The traditional production method of glyceraldehyde mainly uses glycerol as a raw material, and glyceraldehyde is synthesized by a chemical oxidation method, wherein common oxidants are as follows: hydrogen peroxide, peroxy acid, dilute nitric acid, chromium oxide, activated manganese dioxide, dimethyl sulfoxide and the like are used as oxidizing agents to prepare glyceraldehyde. However, hydrogen peroxide, peroxy acid and the like are strong oxidizers, are inflammable and explosive, have the problems of transportation, storage and the like, and have the problem of environmental pollution caused by chromium oxide, dimethyl sulfoxide and the like, so that the search for a novel preparation method which is high in efficiency, low in cost and environment-friendly is still an important target of current research. The reaction formula is as follows:
Figure BDA0001662314010000011
[O]＝H2O2,ROOOH,HNO3collins reagent, Pcc, MnO2,DMSO……
There are reports of anhydrous ZnCl with Lewis acid2As a catalytic dehydrating agent, D-mannitol and acetone are subjected to condensation reaction to synthesize a diisopropylidene condensate, and then NaIO is used4Oxidizing and breaking bonds to prepare D- (R) -glyceraldehyde acetonide, and then removing the acetone to prepare glyceraldehyde. The method has the advantages of high yield, low cost, environmental friendliness and the like. But the method is not suitable for industrial production due to the defects of high raw material price, complex reaction steps and the like. The reaction is as follows:
Figure BDA0001662314010000021
the literature reports that glycerol is used as a raw material to synthesize glyceraldehyde by adopting an indirect electrooxidation method, and although the method has the characteristics of simple reaction steps, high product yield and the like, the method has high energy consumption in the reaction, needs membrane separation and the like, and is not suitable for industrial production. The invention overcomes the defects of the prior art and develops fullerene zinc selenium (C)60the/ZnO/Se) composite material is used as a catalyst to catalyze glycerol and glycerol acetonide to be mildly converted into glyceraldehyde and glycerol acetonide in the presence of oxygen, and the reaction has the advantages of simple and convenient operation, mild conditions, high conversion rate and selectivity, no environmental pollution, environmental protection and easy industrial mass production.
Disclosure of Invention
The invention provides fullerene zinc oxide selenium (C)60the/ZnO/Se) composite material is characterized in that the preparation method of the fullerene zinc oxide selenium composite material comprises the following steps:
(1) uniformly mixing fullerene, zinc salt solution and ammonia water, heating to 120-130 ℃, reacting for 18-20h, naturally cooling to room temperature, and performing post-treatment to obtain fullerene zinc oxide (C)60/ZnO) material;
(2) the zinc (C) fullerene oxide obtained in the step (1)60ZnO) material is added into ethanol solution with volume fraction of 5-10 percent and stirred for 10-15min, then hydrazine hydrate containing selenium is added and stirred continuouslyStirring for 10-15min, heating to 160-60/ZnO/Se) composite material.
In the step (1), 2-3mmol of zinc salt is used per gram of fullerene, and the molar ratio of the zinc salt to ammonia water is 1: 1.2-1.5, wherein the concentration of the zinc salt solution is 1-2mol/L, and the concentration of the ammonia water is 1 mol/L; the fullerene is preferably C60、C70One or two of the components are mixed; the zinc salt is selected from one or more of zinc chloride, zinc nitrate, zinc sulfate or hydrates thereof.
Per gram of fullerene zinc oxide (C) in step (2)60ZnO) material uses 120-180mL of ethanol solution and 10-15mL of selenium-containing hydrazine hydrate; the selenium-containing hydrazine hydrate contains 6-10mg of selenium per ml of hydrazine hydrate.
The reactions of the steps (1) and (2) are preferably carried out in a high-pressure reaction kettle; the post-treatment in the steps (1) and (2) is filtering, washing the precipitate with deionized water and ethanol, and then drying in vacuum for 6-10h at the temperature of 60-80 ℃.
Another embodiment of the present invention provides a fullerene zinc selenium (C)60The preparation method of the/ZnO/Se) composite material is characterized by comprising the following steps:
(1) uniformly mixing fullerene, zinc salt solution and ammonia water, heating to 120-130 ℃, reacting for 18-20h, naturally cooling to room temperature, and performing post-treatment to obtain fullerene zinc oxide (C)60/ZnO) material;
(2) the zinc (C) fullerene oxide obtained in the step (1)60Adding ZnO) material into 5-10% ethanol solution, stirring for 10-15min, adding hydrazine hydrate containing selenium, stirring for 10-15min, heating to 160-180 deg.C, reacting for 12-16h, naturally cooling to room temperature, and post-treating to obtain the fullerene zinc-selenium oxide (C)60/ZnO/Se) composite material.
In the step (1), 2-3mmol of zinc salt is used per gram of fullerene, and the molar ratio of the zinc salt to ammonia water is 1: 1.2-1.5, wherein the concentration of the zinc salt solution is 1-2mol/L, and the concentration of the ammonia water is 1 mol/L; the fullerene is preferably C60、C70One or two of the components are mixed; the zinc salt is selected from chlorideOne or more of zinc, zinc nitrate, zinc sulfate or hydrate thereof.
Per gram of fullerene zinc oxide (C) in step (2)60ZnO) material uses 120-180mL of ethanol solution and 10-15mL of selenium-containing hydrazine hydrate; the selenium-containing hydrazine hydrate contains 6-10mg of selenium per ml of hydrazine hydrate.
The reactions of the steps (1) and (2) are preferably carried out in a high-pressure reaction kettle; the post-treatment in the steps (1) and (2) is filtering, washing the precipitate with deionized water and ethanol, and then drying in vacuum for 6-10h at the temperature of 60-80 ℃.
Another embodiment of the present invention provides the above fullerene zinc selenium (C)60/ZnO/Se) composite material as a catalyst, preferably as an oxidation catalyst.
Another embodiment of the present invention provides the above fullerene zinc selenium (C)60/ZnO/Se) composite material, preferably for selectively oxidizing primary hydroxyl groups to aldehyde groups.
Another embodiment of the present invention provides the above fullerene zinc selenium (C)60The application of the/ZnO/Se) composite material in preparing glyceraldehyde.
Another embodiment of the present invention provides the above fullerene zinc selenium (C)60The application of the/ZnO/Se) composite material in preparing glyceraldehyde by catalytic oxidation of glycerol.
Another embodiment of the present invention provides the above fullerene zinc selenium (C)60/ZnO/Se) composite material in the preparation of glyceraldehyde acetonide.
Another embodiment of the present invention provides the above fullerene zinc selenium (C)60/ZnO/Se) composite material in the preparation of glyceraldehyde acetonide by catalytic oxidation of glyceraldehyde acetonide.
Another embodiment of the present invention provides a method for producing glyceraldehyde, which is characterized by comprising the steps of:
adding appropriate amount of above fullerene zinc oxide selenium (C) into glycerol aqueous solution60/ZnO/Se) composite material, heating to 45-50 deg.C, introducing oxygen, reacting for 5-8 hr, centrifuging to remove fullereneZinc selenium (C) alkyleneoxide60the/ZnO/Se) composite material, adding absolute ethyl alcohol for crystallization after supernatant fluid is subjected to reduced pressure distillation and water removal, filtering, washing and drying to obtain glyceraldehyde.
Wherein the concentration of glycerol aqueous solution is 0.4-0.6mol/L, and the fullerene zinc oxide selenium (C)60The amount of the/ZnO/Se composite material is 40-50mg of fullerene zinc selenium oxide (C) per mol of glycerol60/ZnO/Se) composite material; the flow rate of oxygen was 120-150 mL/min.
In the above preparation method, the yield of glyceraldehyde is more than 90%.
The invention also provides a preparation method of glyceraldehyde acetonide, which is characterized by comprising the following steps:
dissolving glycerol acetonide in acetone, adding appropriate amount of above fullerene zinc oxide selenium (C)60Introducing oxygen to react at room temperature until glycerol acetonide is absent in the reaction solution, and centrifuging to remove fullerene zinc oxide selenium (C)60ZnO/Se) composite material, and concentrating and drying the supernatant fluid under reduced pressure to obtain the glyceraldehyde acetonide.
Wherein the fullerene zinc oxide selenium (C)60the/ZnO/Se) composite material is prepared by using 25-30mg fullerene zinc selenium oxide (C) per mol glycerol acetonide60/ZnO/Se) composite material; the flow rate of oxygen was 180-200 mL/min. The amount of acetone is preferably such that the reactants are well mixed, preferably 1.5-2.0L of acetone per mole of glycerol acetonide.
The reaction for preparing glyceraldehyde acetonide is green, and after the reaction is finished (the reaction time is preferably 20-24 hours), no complicated purification operation is needed, and only the reaction catalyst, namely fullerene zinc selenium oxide (C), is removed by centrifugation60the/ZnO/Se) composite material, concentrating and drying the supernatant to obtain the high-purity glyceraldehyde acetonide (the HPLC purity is more than 98.6 percent).
The invention has the advantages that: the invention overcomes the defects of the prior art and develops fullerene zinc selenium (C)60/ZnO/Se) composite material as a catalyst for catalyzing glycerol and glycerol acetonide to be mildly converted into glyceraldehyde and glycerol acetonide in the presence of oxygenThe reaction has the advantages of simple operation, mild condition, high conversion rate and selectivity, no environmental pollution, environmental protection and easy industrialized mass production.
Drawings
FIG. 1 is a diagram of a simple reaction apparatus for preparing glyceraldehyde according to the present invention;
fig. 2 SEM image of product A, B.
Detailed Description
In order to facilitate a further understanding of the invention, the following examples are provided to illustrate it in more detail. However, these examples are only for better understanding of the present invention and are not intended to limit the scope or the principle of the present invention, and the embodiments of the present invention are not limited to the following.
Example 1
(1) Get C60Fullerene (1.0g), 1mol/L zinc nitrate solution (2mL) and 1mol/L ammonia water (2.4mL) are uniformly mixed in an autoclave, heated to 120 ℃ and 125 ℃ for reaction for 20h, naturally cooled to room temperature, filtered, precipitated, washed by deionized water and ethanol, and dried in vacuum at 80 ℃ for 6h to obtain fullerene zinc oxide (C)60a/ZnO material (hereinafter referred to as product a);
(2) adding the product a (1.0g) into 10 volume percent ethanol solution (120mL), stirring for 10-15min, adding selenium-containing hydrazine hydrate (15mL, containing 150mg of selenium), continuing stirring for 10-15min, heating to 175-180 ℃, reacting for 12h, naturally cooling to room temperature, filtering, washing precipitate with deionized water and ethanol, and vacuum drying at 70 ℃ for 10h to obtain the fullerene zinc oxide selenium (C)60a/ZnO/Se composite material (hereinafter referred to as product A).
Example 2
(1) Get C70Fullerene (1.0g), 2mol/L zinc sulfate solution (1.5mL) and 1mol/L ammonia water (4.5mL) are uniformly mixed in an autoclave, heated to 125 ℃ for reaction for 18h, naturally cooled to room temperature, filtered, precipitated, washed by deionized water and ethanol, and dried in vacuum at 60 ℃ for 10h to obtain the fullerene zinc oxide (C)70a/ZnO material (hereinafter referred to as product b);
(2) adding product b (1.0g) into 5% ethanol solution (180mL), and stirring for 10-15%After min, adding hydrazine hydrate containing selenium (10mL, 60mg containing selenium), continuing stirring for 10-15min, heating to 160-165 ℃ for reaction for 16h, naturally cooling to room temperature, filtering, washing precipitate with deionized water and ethanol, and vacuum drying at 80 ℃ for 6h to obtain the fullerene zinc oxide selenium (C)70a/ZnO/Se composite material (hereinafter referred to as product B).
Example 3
(1) Uniformly mixing graphene (1.0g), 1mol/L zinc nitrate solution (2mL) and 1mol/L ammonia water (2.4mL) in an autoclave, heating to 120-125 ℃ for reaction for 20h, naturally cooling to room temperature, filtering, washing precipitates with deionized water and ethanol, and vacuum-drying at 80 ℃ for 6h to obtain a graphene zinc oxide material (hereinafter referred to as a product c);
(2) and adding the product C (1.0g) into an ethanol solution (120mL) with the volume fraction of 10%, stirring for 10-15min, adding hydrazine hydrate containing selenium (15mL and 150mg containing selenium), continuously stirring for 10-15min, heating to 175-180 ℃, reacting for 12h, naturally cooling to room temperature, filtering, washing precipitates with deionized water and ethanol, and drying in vacuum at 70 ℃ for 10h to obtain the graphene zinc oxide selenium composite material (hereinafter referred to as product C).
Example 4
Adding zinc oxide (1.0g) into an ethanol solution (120mL) with the volume fraction of 10%, stirring for 10-15min, adding hydrazine hydrate containing selenium (15mL, containing 150mg of selenium), continuing stirring for 10-15min, heating to 175-180 ℃, reacting for 12h, naturally cooling to room temperature, filtering, washing precipitates with deionized water and ethanol, and vacuum drying at 70 ℃ for 10h to obtain a product D.
Example 5
Adding the product A (8mg) into a glycerol aqueous solution (0.4mol/L, 500mL), heating to 45-50 ℃, introducing oxygen (the flow rate is 150mL/min), reacting for 5 hours, centrifuging to remove the product A, removing water from supernate through reduced pressure distillation, adding absolute ethyl alcohol for crystallization, filtering, washing and drying to obtain glyceraldehyde (16.4g, the yield is 91.0%), and the structure confirmation data is consistent with the known report.
Example 6
Adding the product B (15mg) into a glycerol aqueous solution (0.6mol/L, 500mL), heating to 45-50 ℃, introducing oxygen (the flow rate is 120mL/min), reacting for 8 hours, centrifuging to remove the product B, removing water from supernate through reduced pressure distillation, adding absolute ethyl alcohol for crystallization, filtering, washing and drying to obtain glyceraldehyde (24.4g, the yield is 90.2%), and the structure confirmation data is consistent with the known report.
Example 7
The product a, b, C and D were used in place of the product a, respectively, according to the method described in example 5, and after 5 hours of reaction, the supernatant was collected and subjected to quantitative analysis by external standard method using high performance liquid chromatography, under the chromatography conditions: using Aminex HPX-87H chromatographic column, at 60 deg.C, with 0.01mol/L of H2SO4The solution was used as a mobile phase at a flow rate of 0.5mL/min with an ultraviolet detector (UVD) and a Refractive Index Detector (RID) in series. The results showed that 15% glyceraldehyde, 13% 1, 3-dihydroxyacetone were detected only in the reaction supernatant using product C; only glycerol was detected in the reaction supernatants using products a, b, c, D, and no glyceraldehyde was found.
Example 8
Dissolving glycerol acetonide (0.1mol) in acetone (150mL), adding product A (2.5mg), introducing oxygen at room temperature to react (the flow rate is 200mL/min) until the reaction solution contains no glycerol acetonide (the reaction time is about 24 hours), centrifuging to remove product A, concentrating the supernatant under reduced pressure, and drying to obtain glycerol acetonide (12.9g, the HPLC purity is 98.6%), wherein the structure confirmation data is consistent with known reports.
Example 9
Dissolving glycerol acetonide (0.1mol) in acetone (200mL), adding product B (3mg), introducing oxygen at room temperature to react (the flow rate is 180mL/min) until the reaction solution contains no glycerol acetonide (the reaction time is about 20 hours), centrifuging to remove product B, concentrating the supernatant under reduced pressure, and drying to obtain glycerol acetonide (12.8g, the HPLC purity is 98.8%), wherein the structure confirmation data is consistent with the known report.
Example 10
According to the method described in example 8, the products a, b, C and D were used in place of the product a, and after 24 hours of reaction, the supernatant was taken and subjected to quantitative analysis by external standard method using high performance liquid chromatography, whereby it was found that glyceraldehyde acetonide was not detected in the reaction supernatant using the products a, b, C and D, and glyceraldehyde acetonide was detected in the reaction supernatant using the product C, but a large amount of glyceraldehyde acetonide was still unreacted.

Claims (7)

1. The preparation method of glyceraldehyde acetonide is characterized by comprising the following steps:
dissolving glycerol acetonide in acetone, adding appropriate amount of fullerene zinc oxide selenium C60Introducing oxygen to react at room temperature until glycerol acetonide is absent in the reaction solution, and centrifuging to remove fullerene, zinc oxide and selenium C60And concentrating the supernatant fluid of the/ZnO/Se composite material under reduced pressure, and drying to obtain the glyceraldehyde acetonide.
2. The method of claim 1, wherein said fullerene zinc selenide C60The amount of the/ZnO/Se composite material is 25-30mg of fullerene zinc oxide selenium C per mol of glycerol acetonide60a/ZnO/Se composite material.
3. The method of claim 1, wherein the flow rate of oxygen is 180-200 mL/min.
4. The method according to claim 1, wherein 1.5 to 2.0L of acetone is used per mole of glycerol acetonide.
5. The method of claim 1, wherein said fullerene zinc selenide C60The preparation method of the/ZnO/Se composite material comprises the following steps:
(1) uniformly mixing fullerene, zinc salt solution and ammonia water, heating to 120-130 ℃, reacting for 18-20h, naturally cooling to room temperature, and performing post-treatment to obtain fullerene zinc oxide C60a/ZnO material;
(2) the fullerene zinc oxide C obtained in the step (1)60Adding ZnO material into 5-10% ethanol solution, stirring for 10-15min, adding hydrazine hydrate containing selenium, stirring for 10-15min, heatingReacting at 160-180 ℃ for 12-16h, naturally cooling to room temperature, and performing post-treatment to obtain the fullerene zinc oxide selenium C60a/ZnO/Se composite material.
6. Fullerene zinc selenium oxide C prepared by the preparation method of claim 560Application of the/ZnO/Se composite material in preparation of glyceraldehyde acetonide.
7. Fullerene zinc selenium oxide C prepared by the preparation method of claim 560Application of the/ZnO/Se composite material in preparing glyceraldehyde acetonide by catalytic oxidation of glyceraldehyde acetonide.
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