CN105439831A - Method for producing 1,3-dihydroxyacetone through catalytic oxidation with supported gold catalyst - Google Patents
Method for producing 1,3-dihydroxyacetone through catalytic oxidation with supported gold catalyst Download PDFInfo
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- CN105439831A CN105439831A CN201510817848.8A CN201510817848A CN105439831A CN 105439831 A CN105439831 A CN 105439831A CN 201510817848 A CN201510817848 A CN 201510817848A CN 105439831 A CN105439831 A CN 105439831A
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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
- C07C45/39—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 secondary hydroxyl group
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/005—Spinels
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/007—Mixed salts
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/66—Silver or gold
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8926—Copper and noble metals
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Abstract
The invention discloses a method for producing 1,3-dihydroxyacetone through catalytic oxidation with a supported gold catalyst. According to the method, a glycerin aqueous solution and oxygen are used as raw materials, ZnO, Cu-Al hydrotalcite or spinel supported gold is used as the catalyst, and high selectivity conversion from glycerin to the 1,3-dihydroxyacetone in an oxidation manner is realized in the absence of alkali. The method is performed in the absence of alkali, has low requirement for reaction equipment and is low in investment; the catalyst preparation technology is simple, reaction raw materials are easy to obtain, the reaction process is mild, the method is environment-friendly and free of pollution, the catalyst has advantages of convenience in recovery, long service life and the like, and the industrial prospect is bright.
Description
Technical field
The invention belongs to the preparing technical field of 1,3-Dihydroxyacetone, be specifically related to a kind of method of load type gold catalyst catalyzed oxidation glycerol production 1,3-Dihydroxyacetone.
Background technology
Day by day reduce at fossil class Nonrenewable resources reserves, today that the deterioration of the ecological environment that price increase, Greenhouse effect cause is day by day serious, receive increasing concern with the research that the renewable resourcess such as biomass are Material synthesis fuels and chemicals.Glycerine is as a kind of important platform chemicals, it mainly comes from the by product produced in the production process of biofuel, because biofuel production capacity constantly expands, there is the situation that supply exceed demand in glycerine, how to be translated into the downstream chemical product (as R-Glyceric acid, Glycerose, otan, lactic acid etc.) of high added value, to become study hotspot.
1,3-Dihydroxyacetone (being called for short DHA) is the simplest three carbon ketoses, in foodstuff additive, makeup sun-screening agent, pharmaceutical intermediate and Chemical Manufacture, have extensive use.At present, the production of DHA has biological process and chemical method, and the former is mainly by fermentative action, but the productive rate that there is fermentative production bacterial classification is low, fermentation period long, the separating-purifying high in cost of production shortcoming of product.And chemical method because of its there is reaction conditions gentleness, the low and advantages such as simple, product yield is high and purity is high, reaction process environmentally safe to production unit requirement, enjoy people to pay close attention to.
Obtain 1,3-Dihydroxyacetone the most direct mode be under catalyzer and oxygen existence condition by glycerine by single step reaction.Such as, HiroshiKimura etc. adopt Pt/C, Pt-Bi/C and Pt-Bi-Ce/C catalyst oxidation glycerine to prepare 1,3-Dihydroxyacetone, achieve certain catalytic effect (Appl.Catal., A, 1993,96:217-228.); WenbinHu etc. are by improving composition and the conversion unit of Pt-Bi/C catalyzer, obtain that productive rate is 48% in acid condition 1,3-otan and 80% glycerol conversion yield (Ind.Eng.Chem.Res., 2010,49 (21): 10876-10882.); LingDan etc. are by changing composition and the reaction system of Pt-Bi/C catalyzer, under neutrallty condition, achieve the selectivity (Chin.J.Catal. of 1,3-Dihydroxyacetone of high glycerol conversion yield (91.5%) and 49%, 2011,32:1831-1837.); Pt-Sb loads on multi-walled carbon nano-tubes by RenfengNie etc., under alkali-free condition, be oxidized glycerine, and under 90% transformation efficiency, 1,3-Dihydroxyacetone selectivity is 51.4% (Appl.Catal.B, 2012,127:212-220.).It is catalyzer that nearest Shu-SenLiu etc. find with Au/CuO, under neutrallty condition, when glycerine and golden mol ratio 1000, obtain 1 compared with highly selective, 3-otan (82.3%), but glycerol conversion yield lower (20%), when improving glycerine and (100) during golden ratio, glycerine all transforms, but 1, comparatively large (54.6%) (ACSCatal., 2014,4:2226-2230.) of the selectivity range of decrease of 3-otan.Therefore, how to improve the productive rate of 1,3-Dihydroxyacetone, become the object that investigators are common.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of simple to operate, and under alkali-free condition, load type gold catalyst catalyzed oxidation glycerine high conversion, highly selective produce the method for 1,3-Dihydroxyacetone.
Solving the problems of the technologies described above adopted technical scheme is: by glycerine and oxygen under load type gold catalyst katalysis, react in autoclave, obtain 1,3-otan, the carrier of described load type gold catalyst is ZnO, copper aluminum hydrotalcite, copper aluminum ratio are any one in the spinel of 5:1 or 1:3.
In above-mentioned load type gold catalyst, the charge capacity of gold is preferably 1% ~ 3%, and carrier preferably copper aluminum ratio is the spinel of 5:1.
In above-mentioned preparation method, glycerine is 100 ~ 1000 with the mol ratio of gold, preferably glycerine is 100 with the mol ratio of gold, described temperature of reaction is 60 ~ 80 DEG C, the reaction times is 2 ~ 5 hours, oxygen pressure is 1 ~ 2MPa, and preferable reaction temperature is 80 DEG C, the reaction times is 2 ~ 3 hours, oxygen pressure is 1 ~ 2MPa.
Load type gold catalyst of the present invention adopts deposition-precipitation method to prepare, and concrete preparation method is: by HAuCl
4add in distilled water, mix, then add urea and corresponding carrier, be heated with stirring to 70 ~ 80 DEG C, keep 6 ~ 8 hours, be down to room temperature, keep 16 ~ 20 hours, suction filtration, to be washed to without Cl
-exist, 100 ~ 110 DEG C of dryings 4 ~ 6 hours, then in fluidizing air, be warming up to 200 DEG C with 1 ~ 2 DEG C/min, constant temperature calcining 4 ~ 5 hours, after naturally cooling, obtains load type gold catalyst.
The present invention, using aqueous glycerin solution and oxygen as raw material, with ZnO, copper aluminum hydrotalcite or copper aluminate gold-supported for catalyzer, under the condition of alkali-free, is achieved glycerine and is transformed by the highly selective of mode of oxidizing to 1,3-Dihydroxyacetone.The inventive method is carried out under alkali-free condition, low to the requirement of conversion unit, invests little; Catalyst preparation process is simple, and reaction raw materials is easy to get, and reaction process is gentle, environmentally friendly, pollution-free, and catalyzer possesses advantages such as reclaiming conveniently, the life-span is long, has good industrial prospect.
Embodiment
Below in conjunction with embodiment, the present invention is described in more detail, but protection scope of the present invention is not limited only to these embodiments.
Embodiment 1
According to the mol ratio 100:1 of glycerine with gold, 24mL0.1mol/L aqueous glycerin solution, 0.1576g3%Au/ spinel (in spinel, copper al mole ratio is 5:1) are joined in 50mL autoclave, airtight completely after, emptying three times are carried out with high purity oxygen gas under room temperature, then 1.0MPa high purity oxygen gas is filled with, be heated with stirring to 80 DEG C, isothermal reaction 2 hours, after reaction terminates, be cooled with an ice bath to room temperature, centrifugal, filtration, reaction solution carries out high performance liquid chromatography detection, measure the transformation efficiency of glycerine and the productive rate of 1,3-Dihydroxyacetone.Analysis draws, glycerol conversion yield is 76.7%, and 1,3-Dihydroxyacetone selectivity is 97.3%.
Embodiment 2
According to the mol ratio 100:1 of glycerine with gold, 24mL0.1mol/L aqueous glycerin solution, 0.1576g3%Au/ZnO are joined in 50mL autoclave, airtight completely after, emptying three times are carried out with high purity oxygen gas under room temperature, then be filled with 1.0MPa high purity oxygen gas, be heated with stirring to 80 DEG C, isothermal reaction 2 hours, after reaction terminates, be cooled with an ice bath to room temperature, centrifugal, filtration, reaction solution carries out high performance liquid chromatography detection, measure the transformation efficiency of glycerine and the productive rate of 1,3-Dihydroxyacetone.Analysis draws, glycerol conversion yield is 87.1%, and 1,3-Dihydroxyacetone selectivity is 74.8%.
Embodiment 3
According to the mol ratio 100:1 of glycerine with gold, 24mL0.1mol/L aqueous glycerin solution, 0.1576g3%Au/ copper aluminum hydrotalcite are joined in 50mL autoclave, airtight completely after, emptying three times are carried out with high purity oxygen gas under room temperature, then be filled with 1.0MPa high purity oxygen gas, be heated with stirring to 80 DEG C, isothermal reaction 2 hours, after reaction terminates, be cooled with an ice bath to room temperature, centrifugal, filtration, reaction solution carries out high performance liquid chromatography detection, measure the transformation efficiency of glycerine and the productive rate of 1,3-Dihydroxyacetone.Analysis draws, glycerol conversion yield is 61.5%, and 1,3-Dihydroxyacetone selectivity is 98.0%.
Embodiment 4
According to the mol ratio 100:1 of glycerine with gold, 24mL0.1mol/L aqueous glycerin solution, 0.1576g3%Au/ spinel (in spinel, copper al mole ratio is 1:3) are joined in 50mL autoclave, airtight completely after, emptying three times are carried out with high purity oxygen gas under room temperature, then 1.0MPa high purity oxygen gas is filled with, be heated with stirring to 80 DEG C, isothermal reaction 2 hours, after reaction terminates, be cooled with an ice bath to room temperature, centrifugal, filtration, reaction solution carries out high performance liquid chromatography detection, measure the transformation efficiency of glycerine and the selectivity of 1,3-Dihydroxyacetone.Analysis draws, glycerol conversion yield is 68.4%, and 1,3-Dihydroxyacetone selectivity is 94.7%.
Embodiment 5
According to the mol ratio 100:1 of glycerine with gold, 24mL0.1mol/L aqueous glycerin solution, 0.1576g3%Au/ spinel (in spinel, copper al mole ratio is 5:1) are joined in 50mL autoclave, airtight completely after, emptying three times are carried out with high purity oxygen gas under room temperature, then 2.0MPa high purity oxygen gas is filled with, be heated with stirring to 60 DEG C, isothermal reaction 4.5 hours, after reaction terminates, be cooled with an ice bath to room temperature, centrifugal, filtration, reaction solution carries out high performance liquid chromatography detection, measure the transformation efficiency of glycerine and the selectivity of 1,3-Dihydroxyacetone.Analysis draws, glycerol conversion yield is 66.6%, and 1,3-Dihydroxyacetone selectivity is 97.3%.
Embodiment 6
According to the mol ratio 500:1 of glycerine with gold, 24mL0.1mol/L aqueous glycerin solution, 0.0315g3%Au/ spinel (in spinel, copper al mole ratio is 5:1) are joined in 50mL autoclave, airtight completely after, emptying three times are carried out with high purity oxygen gas under room temperature, then 1.0MPa high purity oxygen gas is filled with, be heated with stirring to 80 DEG C, isothermal reaction 2 hours, after reaction terminates, be cooled with an ice bath to room temperature, centrifugal, filtration, reaction solution carries out high performance liquid chromatography detection, measure the transformation efficiency of glycerine and the selectivity of 1,3-Dihydroxyacetone.Analysis draws, glycerol conversion yield is 42.4%, and 1,3-Dihydroxyacetone selectivity is 96.6%.
Embodiment 7
According to the mol ratio 1000:1 of glycerine with gold, 24mL0.1mol/L aqueous glycerin solution, 0.0158g3%Au/ spinel (in spinel, copper al mole ratio is 5:1) are joined in 50mL autoclave, airtight completely after, emptying three times are carried out with high purity oxygen gas under room temperature, then 1.0MPa high purity oxygen gas is filled with, be heated with stirring to 80 DEG C, isothermal reaction 2 hours, after reaction terminates, be cooled with an ice bath to room temperature, centrifugal, filtration, reaction solution carries out high performance liquid chromatography detection, measure the transformation efficiency of glycerine and the selectivity of 1,3-Dihydroxyacetone.Analysis draws, glycerol conversion yield is 21.6%, and 1,3-Dihydroxyacetone selectivity is 94.8%.
Claims (8)
1. a load type gold catalyst catalyzed oxidation glycerol production 1, the method of 3-otan, it is characterized in that: by glycerine and oxygen under load type gold catalyst katalysis, react in autoclave, obtain 1,3-otan, the carrier of described load type gold catalyst is ZnO, copper aluminum hydrotalcite, copper aluminum ratio are any one in the spinel of 5:1 or 1:3.
2. the method for load type gold catalyst catalyzed oxidation glycerol production 1,3-Dihydroxyacetone according to claim 1, is characterized in that: the spinel of the carrier of described load type gold catalyst to be copper aluminum ratio be 5:1.
3. the method for load type gold catalyst catalyzed oxidation glycerol production 1,3-Dihydroxyacetone according to claim 1, is characterized in that: in described load type gold catalyst, the charge capacity of gold is 1% ~ 3%.
4. the method for the load type gold catalyst catalyzed oxidation glycerol production 1,3-Dihydroxyacetone according to claims 1 to 3 any one, is characterized in that: described glycerine is 100 ~ 1000 with the mol ratio of gold.
5. the method for the load type gold catalyst catalyzed oxidation glycerol production 1,3-Dihydroxyacetone according to claims 1 to 3 any one, is characterized in that: described glycerine is 100 with the mol ratio of gold.
6. the method for load type gold catalyst catalyzed oxidation glycerol production 1,3-Dihydroxyacetone according to claim 5, is characterized in that: the temperature of described reaction is 60 ~ 80 DEG C, the time is 2 ~ 5 hours, oxygen pressure is 1 ~ 2MPa.
7. the method for load type gold catalyst catalyzed oxidation glycerol production 1,3-Dihydroxyacetone according to claim 5, is characterized in that: the temperature of described reaction is 80 DEG C, the time is 2 ~ 3 hours, oxygen pressure is 1 ~ 2MPa.
8. the method for load type gold catalyst catalyzed oxidation glycerol production 1,3-Dihydroxyacetone according to claim 1, is characterized in that: described load type gold catalyst adopts deposition-precipitation method to prepare, by HAuCl
4add in distilled water, mix, then add urea and corresponding carrier, be heated with stirring to 70 ~ 80 DEG C, keep 6 ~ 8 hours, be down to room temperature, keep 16 ~ 20 hours, suction filtration, to be washed to without Cl
-exist, 100 ~ 110 DEG C of dryings 4 ~ 6 hours, then in fluidizing air, be warming up to 200 DEG C with 1 ~ 2 DEG C/min, constant temperature calcining 4 ~ 5 hours, after naturally cooling, obtains load type gold catalyst.
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108273502A (en) * | 2018-03-28 | 2018-07-13 | 北京化工大学 | One kind preparing C3H6O3 catalyst and preparation method thereof by glycerine |
| CN108686682A (en) * | 2018-05-16 | 2018-10-23 | 扬州工业职业技术学院 | A kind of method of green oxidation synthetic glycerine aldehyde |
| CN109400461A (en) * | 2018-09-17 | 2019-03-01 | 南京工程学院 | The method and its application of hydrogen peroxide catalyzed glycerol |
| CN109503340A (en) * | 2018-12-22 | 2019-03-22 | 江西师范大学 | A kind of preparation process of C3H6O3 |
| CN110102293A (en) * | 2019-06-14 | 2019-08-09 | 北方民族大学 | Gold/oxide catalyst and the application in DHA is prepared in catalysis oxidation glycerol |
| CN110227450A (en) * | 2019-06-26 | 2019-09-13 | 北京化工大学 | A kind of metal cooperates with efficient catalytic glycerol to prepare the catalyst and preparation method thereof of DHA with carrier alkalinity |
| CN110252298A (en) * | 2019-06-26 | 2019-09-20 | 北京化工大学 | A kind of metal oxide supported golden efficient catalytic glycerol prepares catalyst of DHA and preparation method thereof |
| CN110872215A (en) * | 2019-11-25 | 2020-03-10 | 北方民族大学 | Mesoporous CuO-CeO2Application of composite oxide supported Au catalyst in catalytic oxidation of glycerol |
| CN114029058A (en) * | 2021-11-30 | 2022-02-11 | 中国石油大学(华东) | Catalyst for preparing 1,3-dihydroxyacetone by glycerol oxidation and method thereof |
| CN114689704A (en) * | 2020-12-26 | 2022-07-01 | 四川汇宇制药股份有限公司 | Method for detecting 1,3-dihydroxyacetone and related impurities |
| CN116809063A (en) * | 2023-06-12 | 2023-09-29 | 安徽师范大学 | Oxidation catalyst, preparation method and application thereof |
-
2015
- 2015-11-23 CN CN201510817848.8A patent/CN105439831B/en not_active Expired - Fee Related
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| ALBERTO VILLA ET AL.: "Au on MgAl2O4 spinels: The effect of support surface properties in glycerol oxidation", 《JOURNAL OF CATALYSIS》 * |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108273502A (en) * | 2018-03-28 | 2018-07-13 | 北京化工大学 | One kind preparing C3H6O3 catalyst and preparation method thereof by glycerine |
| CN108686682A (en) * | 2018-05-16 | 2018-10-23 | 扬州工业职业技术学院 | A kind of method of green oxidation synthetic glycerine aldehyde |
| CN108686682B (en) * | 2018-05-16 | 2020-08-25 | 扬州工业职业技术学院 | Green oxidation synthesis method of glyceraldehyde |
| CN109400461A (en) * | 2018-09-17 | 2019-03-01 | 南京工程学院 | The method and its application of hydrogen peroxide catalyzed glycerol |
| CN109503340A (en) * | 2018-12-22 | 2019-03-22 | 江西师范大学 | A kind of preparation process of C3H6O3 |
| CN110102293A (en) * | 2019-06-14 | 2019-08-09 | 北方民族大学 | Gold/oxide catalyst and the application in DHA is prepared in catalysis oxidation glycerol |
| CN110252298A (en) * | 2019-06-26 | 2019-09-20 | 北京化工大学 | A kind of metal oxide supported golden efficient catalytic glycerol prepares catalyst of DHA and preparation method thereof |
| CN110227450A (en) * | 2019-06-26 | 2019-09-13 | 北京化工大学 | A kind of metal cooperates with efficient catalytic glycerol to prepare the catalyst and preparation method thereof of DHA with carrier alkalinity |
| CN110252298B (en) * | 2019-06-26 | 2021-06-25 | 北京化工大学 | Catalyst for preparing DHA (docosahexaenoic acid) by efficiently catalyzing glycerol through metal oxide supported gold and preparation method thereof |
| CN110872215A (en) * | 2019-11-25 | 2020-03-10 | 北方民族大学 | Mesoporous CuO-CeO2Application of composite oxide supported Au catalyst in catalytic oxidation of glycerol |
| CN114689704A (en) * | 2020-12-26 | 2022-07-01 | 四川汇宇制药股份有限公司 | Method for detecting 1,3-dihydroxyacetone and related impurities |
| CN114029058A (en) * | 2021-11-30 | 2022-02-11 | 中国石油大学(华东) | Catalyst for preparing 1,3-dihydroxyacetone by glycerol oxidation and method thereof |
| CN116809063A (en) * | 2023-06-12 | 2023-09-29 | 安徽师范大学 | Oxidation catalyst, preparation method and application thereof |
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