CN117843469A - Method for preparing methane triacetic acid from ketoglutaric acid and glyoxylic acid - Google Patents
Method for preparing methane triacetic acid from ketoglutaric acid and glyoxylic acid Download PDFInfo
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- CN117843469A CN117843469A CN202311854022.XA CN202311854022A CN117843469A CN 117843469 A CN117843469 A CN 117843469A CN 202311854022 A CN202311854022 A CN 202311854022A CN 117843469 A CN117843469 A CN 117843469A
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- acid
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- carboxymethyl
- hydroxy
- hydrodeoxygenation
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- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 title claims abstract description 28
- XYKQMCAWQYSNKA-UHFFFAOYSA-N 3-(carboxymethyl)pentanedioic acid Chemical compound OC(=O)CC(CC(O)=O)CC(O)=O XYKQMCAWQYSNKA-UHFFFAOYSA-N 0.000 title claims abstract description 18
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- 229910010413 TiO 2 Inorganic materials 0.000 claims abstract description 23
- -1 3-carboxymethyl-2-hydroxy-4-oxo glutaric acid Chemical compound 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 238000005882 aldol condensation reaction Methods 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910004298 SiO 2 Inorganic materials 0.000 claims abstract description 3
- 239000004480 active ingredient Substances 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000011068 loading method Methods 0.000 claims description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- QRNPTSGPQSOPQK-UHFFFAOYSA-N magnesium zirconium Chemical compound [Mg].[Zr] QRNPTSGPQSOPQK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000002028 Biomass Substances 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 2
- 239000003638 chemical reducing agent Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 9
- 239000012018 catalyst precursor Substances 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 5
- KPGXRSRHYNQIFN-UHFFFAOYSA-L 2-oxoglutarate(2-) Chemical compound [O-]C(=O)CCC(=O)C([O-])=O KPGXRSRHYNQIFN-UHFFFAOYSA-L 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- AUZFRUHVDNDVJI-UHFFFAOYSA-N 3-acetylpentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)C(C)=O AUZFRUHVDNDVJI-UHFFFAOYSA-N 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012621 metal-organic framework Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- 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
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a method for preparing methane triacetic acid from ketoglutaric acid and glyoxylic acid. The method comprises the following steps: s1, performing aldol condensation on ketoglutaric acid and glyoxalic acid to obtain 3-carboxymethyl-2-hydroxy-4-oxo glutaric acid; s2, obtaining methane triacetic acid through hydrodeoxygenation of the 3-carboxymethyl-2-hydroxy-4-oxo-glutaric acid; the hydrodeoxygenation is performed in the presence of hydrogen and a catalyst; the catalyst is a supported catalyst, and the carrier is TiO 2 、SiO 2 、ZrO 2 、CeO 2 、Al 2 O 3 And active carbon, wherein the active ingredients are metal and oxide. The raw materials adopted by the method of the invention are derived from biomass, and the used solvent is H 2 O，H 2 As a reducing agent, the reaction process is green, and byproducts harmful to the environment are not generated.
Description
Technical Field
The invention relates to a method for preparing methane triacetic acid from ketoglutaric acid and glyoxylic acid, belonging to the technical field of organic synthesis.
Background
Methane triacetic acid is used as a precursor for synthesizing metal-organic framework materials, organometallic complex catalysts, pharmaceuticals, and the like. At present, the main production process of methane triacetic acid is that citric acid and cyanoacetic acid sequentially undergo dehydration reaction, condensation reaction, hydrogenation reaction and hydrolysis reaction. However, toxic cyanoacetic acid and a large amount of organic solvents are required for the reaction, and the reaction process is inefficient. Therefore, the synthesis of methane triacetic acid by the process of catalytic conversion using renewable biomass existing in large quantities in nature as a raw material has received attention.
Disclosure of Invention
The invention aims to provide a method for preparing methane triacetic acid from ketoglutaric acid and glyoxylic acid, wherein the ketoglutaric acid and glyoxylic acid raw materials used by the method are derived from renewable biomass, and the preparation process is environment-friendly and pollution-free.
The preparation method of the methane triacetic acid provided by the invention comprises the following steps:
s1, performing aldol condensation on ketoglutaric acid and glyoxalic acid to obtain 3-carboxymethyl-2-hydroxy-4-oxo glutaric acid;
s2, obtaining methane triacetic acid through hydrodeoxygenation of the 3-carboxymethyl-2-hydroxy-4-oxo-glutaric acid.
In the preparation method of the invention, in the step S1, the aldol condensation is carried out in the presence of a base catalyst;
the dosage of the base catalyst is 5-120% of the mass of the ketoglutaric acid;
the alkali catalyst can be NaOH, KOH, ammonia water, mgO, caO or magnesium-zirconium composite oxide;
in step S1, the solvent used for aldol condensation is preferably water, and the reaction conditions are as follows:
the temperature is 30-70 ℃ and the time is 1-24 h.
In the preparation method of the invention, in the step S2, the hydrodeoxygenation is carried out under the condition that hydrogen and a catalyst exist;
the catalyst is a supported catalyst, and the carrier is TiO 2 、SiO 2 、ZrO 2 、CeO 2 、Al 2 O 3 And active carbon, wherein the active ingredients are metal and oxide;
the metal is at least one of Pd, pt, rh, ru and Ni;
the oxide is ReO x And/or MoO x ，x＝1～3；
The loading of the metal is 0.5-5%, and the loading of the oxide is 1-15%.
In the preparation method of the invention, in the step S2, the dosage of the catalyst is 10-200% of the mass of the 3-carboxymethyl-2-hydroxy-4-oxoglutarate.
In the preparation method of the invention, in the step S2, the reaction conditions of the hydrodeoxygenation are as follows:
the temperature is 180-220 ℃, the time is 4-24 h, H 2 The pressure is 1-4 MPa.
In the preparation method of the invention, in the step S2, the solvent used for hydrodeoxygenation is water.
Compared with the prior art, the invention has the following advantages:
the raw materials adopted by the method of the invention are derived from biomass, and the used solvent is H 2 O，H 2 As a reducing agent, the reaction process is green, and byproducts harmful to the environment are not generated.
Detailed Description
The experimental methods used in the following examples are conventional methods unless otherwise specified.
Materials, reagents and the like used in the examples described below are commercially available unless otherwise specified.
In the following examples, specific catalysts were prepared as follows:
1. supported Pd/TiO 2 Preparation of the catalyst
Pd/TiO with 2% loading 2 The preparation of the catalyst is illustrated by way of non-limiting example.
To a 100mL round bottom flask with stirrer was added 2mL of [ Pd (NH) 3 ) 4 ](NO 3 ) 2 The aqueous solution (Pd concentration 10 mg/mL) and 10mL deionized water were stirred well. Further, 1g of TiO 2 Added to the solution and stirred at 600rpm at room temperature for 6h. After evaporating the water, the solid sample was dried in an oven at 110 ℃ for 12 hours to obtain a catalyst precursor. Transferring the catalyst precursor into a quartz tube, roasting for 3h in flowing air, and further heating in 20% H 2 /N 2 Roasting for 2 hours at the temperature of 500 ℃ to obtain the supported 2% Pd/TiO 2 A catalyst.
2. Supported MoO x /TiO 2 Preparation of the catalyst
In MoO x MoO with loading of 10% respectively x /TiO 2 The preparation of the catalyst is illustrated by way of non-limiting example.
To a 100mL round bottom flask with stirrer was added 5mL (NH 4 ) 6 Mo 7 O 24 The aqueous solution (Mo concentration 20 mg/mL) and 10mL deionized water were stirred well. Further, 1g of TiO 2 Added to the solution and stirred at 600rpm at room temperature for 6h. After evaporating the water, the solid sample was dried in an oven at 110 ℃ for 12 hours to obtain a catalyst precursor. Transferring the catalyst precursor into a quartz tube, and roasting for 3h in flowing air to obtain the supported 10% MoO x /TiO 2 A catalyst.
3. Supported Pd-MoO x /TiO 2 Preparation of the catalyst
In Pd and MoO x Pd-MoO with loading of 2% and 10% respectively x /TiO 2 The preparation of the catalyst is illustrated by way of non-limiting example.
To a 100mL round bottom flask with stirrer was added 5mL (NH 4 ) 6 Mo 7 O 24 Aqueous solution) Mo concentration of 20 mg/mL), 2mL [ Pd (NH) 3 ) 4 ](NO 3 ) 2 The aqueous solution (Pd concentration 10 mg/mL) and 10mL deionized water were stirred well. Further, 1g of TiO 2 Added to the solution and stirred at 600rpm at room temperature for 6h. After evaporating the water, the solid sample was dried in an oven at 110 ℃ for 12 hours to obtain a catalyst precursor. Transferring the catalyst precursor into a quartz tube, and roasting for 3h in flowing air to obtain the supported Pd-MoO x /TiO 2 Catalysts, wherein Pd and MoO x The loadings of (2) and (10) respectively.
4. Supported ReO x //TiO 2 Preparation of the catalyst
With ReO of x ReO with 10% loading x /TiO 2 The preparation of the catalyst is illustrated by way of non-limiting example.
To a 100mL round bottom flask with stirrer was added 5mL of HReO 4 The aqueous solution (Re concentration 20 mg/mL) and 10mL deionized water were stirred well. Further, 1g of TiO 2 Added to the solution and stirred at 600rpm at room temperature for 6h. After evaporating the water, the solid sample was dried in an oven at 110 c for 12 hours,obtaining the catalyst precursor. Transferring the catalyst precursor into a quartz tube, and roasting for 3 hours in flowing air to obtain the supported 10% ReO x /TiO 2 A catalyst.
Example 1,
The reaction equation for preparing methane triacetic acid is as follows:
1. conversion of ketoglutarate and glyoxylate to 3-carboxymethyl-2-hydroxy-4-oxoglutarate
A NaOH catalyst is used as an example for non-limiting illustration.
Into a 50mL autoclave, 6.72g of KOH (which was used in an amount of 115% by mass of ketoglutaric acid), 5.84g of ketoglutaric acid, 2.96g of glyoxylic acid, 20mL of deionized water were added. After the reaction kettle is closed, the reaction kettle is placed in a heating furnace to be heated to 50 ℃, and the stirring speed of the reaction kettle is controlled to be 600rpm. After 5 hours, the heating was stopped and cooled to room temperature. The reaction solution was fixed to a volume of 100mL, and the reaction product was analyzed by high performance liquid chromatography (column ShodexSUGAR SH 1011). The substrates ketoglutarate and glyoxylate were completely converted, the yield of 3-carboxymethyl-2-hydroxy-4-oxoglutarate reached 97%. The resulting 3-carboxymethyl-2-hydroxy-4-oxoglutarate solution was used directly in the next reaction without isolation.
2. Conversion of 3-carboxymethyl-2-hydroxy-4-oxoglutarate to methane triacetate
In Pd and MoO x Pd/TiO loading of 2% and 10%, respectively 2 And MoO x /TiO 2 The catalysts are illustrated by way of non-limiting example.
In a 50mL autoclave, 1mL of 3-carboxymethyl-2-hydroxy-4-oxoglutarate solution, 13mL of deionized water, 6mL of hydrochloric acid solution (1.0 mol/L), 50mg of Pd/TiO were added in this order 2 Catalyst and 0.1g of MoO x /TiO 2 Catalyst (catalyst amount was 23% of the mass of 3-carboxymethyl-2-hydroxy-4-oxoglutarate). After the reaction kettle is closed, 1MPa of H is flushed in 2 To replace the air in the reaction kettle,repeatedly inflating and deflating for three times, and inflating with H of 2MPa 2 The reaction kettle was placed in a heating furnace and heated to 200 ℃, and the stirring rate of the reaction kettle was controlled to 600rpm. Stopping heating after 24 hours, cooling to room temperature and cooling H in the reaction kettle 2 And (5) discharging. The reaction solution and the catalyst were separated by filtration under reduced pressure. The filtrate was fixed to a volume of 100mL, and the reaction product was analyzed by high performance liquid chromatography (column ShodexSUGARSH 1011). The conversion of the substrate 3-carboxymethyl-2-hydroxy-4-oxoglutarate was 100% and the yield of methane triacetic acid was 89%.
According to the above results, the total yield of methane triacetic acid was 86% after two-step reaction using ketoglutaric acid and glyoxylic acid as raw materials. The method is an effective methane triacetic acid synthesis method.
EXAMPLE 2,
1. Conversion of ketoglutarate and glyoxylate to 3-carboxymethyl-2-hydroxy-4-oxoglutarate
The MgO catalyst is taken as an example for non-limiting illustration.
Into a 50mL autoclave, 0.3g of MgO (which is used in an amount of 5% by mass of ketoglutaric acid), 5.84g of ketoglutaric acid, 2.96g of glyoxylic acid, 4.80g of NaOH, and 20mL of deionized water were added. After the reaction kettle is closed, the reaction kettle is placed in a heating furnace to be heated to 50 ℃, and the stirring speed of the reaction kettle is controlled to be 600rpm. After 3h, the heating was stopped and cooled to room temperature. The reaction mixture was fixed to a volume of 100mL, and the reaction product was analyzed by high performance liquid chromatography (column ShodexSUGARSH 1011). The substrates ketoglutarate and glyoxylate were completely converted, the yield of 3-carboxymethyl-2-hydroxy-4-oxoglutarate reached 97%. The resulting 3-carboxymethyl-2-hydroxy-4-oxoglutarate solution was used directly in the next reaction without isolation.
2. Conversion of 3-carboxymethyl-2-hydroxy-4-oxoglutarate to methane triacetate
In Pd and ReO x Pd/TiO loading of 2% and 10%, respectively 2 And ReO x /TiO 2 The catalysts are illustrated by way of non-limiting example.
1mL of 3-carboxymethyl-2-hydroxy-4-oxoglutarate solution and 13mL of deionized water were sequentially added to a 50mL autoclaveDeionized water, 6mL hydrochloric acid solution (1.0 mol/L), 50mg Pd/TiO 2 Catalyst and 0.8g of ReO x /TiO 2 Catalyst (the catalyst amount is 182% of the mass of 3-carboxymethyl-2-hydroxy-4-oxoglutarate). After the reaction kettle is closed, 1MPa of H is flushed in 2 Replace the air in the reaction kettle, repeatedly charge and discharge air for three times, and charge H of 2MPa 2 The reaction kettle was placed in a heating furnace and heated to 200 ℃, and the stirring rate of the reaction kettle was controlled to 600rpm. Stopping heating after 12H, cooling to room temperature and cooling H in the reaction kettle 2 And (5) discharging. The reaction solution and the catalyst were separated by filtration under reduced pressure. The filtrate was fixed to a volume of 100mL, and the reaction product was analyzed by high performance liquid chromatography (column ShodexSUGARSH 1011). The conversion of the substrate 3-carboxymethyl-2-hydroxy-4-oxoglutarate was 100% and the yield of methane triacetic acid was 80%.
Claims (9)
1. A method for preparing methane triacetic acid, comprising the following steps:
s1, performing aldol condensation on ketoglutaric acid and glyoxalic acid to obtain 3-carboxymethyl-2-hydroxy-4-oxo glutaric acid;
s2, obtaining methane triacetic acid through hydrodeoxygenation of the 3-carboxymethyl-2-hydroxy-4-oxo-glutaric acid.
2. The method of manufacturing according to claim 1, characterized in that: in step S1, the aldol condensation is performed in the presence of a base catalyst;
the dosage of the base catalyst is 5-120% of the mass of the ketoglutaric acid.
3. The preparation method according to claim 2, characterized in that: the alkali catalyst is NaOH, KOH, ammonia water, mgO, caO or magnesium-zirconium composite oxide.
4. A production method according to any one of claims 1 to 3, characterized in that: in the step S1, the solvent adopted by aldol condensation is water, and the reaction conditions are as follows:
the temperature is 30-70 ℃ and the time is 1-24 h.
5. The method according to any one of claims 1 to 4, wherein: in step S2, the hydrodeoxygenation is performed in the presence of hydrogen and a catalyst;
the catalyst is a supported catalyst, and the carrier is TiO 2 、SiO 2 、ZrO 2 、CeO 2 、Al 2 O 3 And active carbon, wherein the active ingredients are metal and oxide.
6. The method of manufacturing according to claim 5, wherein: the metal is at least one of Pd, pt, rh, ru and Ni;
the oxide is ReO x And/or MoO x ，x＝1～3；
The loading of the metal is 0.5-5%, and the loading of the oxide is 1-15%.
7. The method of manufacturing according to claim 5 or 6, characterized in that: in the step S2, the dosage of the catalyst is 10-200% of the mass of the 3-carboxymethyl-2-hydroxy-4-oxoglutarate.
8. The production method according to any one of claims 1 to 7, characterized in that: in step S2, the reaction conditions of the hydrodeoxygenation are as follows:
the temperature is 180-220 ℃, the time is 4-24 h, H 2 The pressure is 1-4 MPa.
9. The production method according to any one of claims 1 to 8, characterized in that: in step S2, the solvent used for hydrodeoxygenation is water.
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| CN202311854022.XA CN117843469A (en) | 2023-12-29 | 2023-12-29 | Method for preparing methane triacetic acid from ketoglutaric acid and glyoxylic acid |
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| CN202311854022.XA CN117843469A (en) | 2023-12-29 | 2023-12-29 | Method for preparing methane triacetic acid from ketoglutaric acid and glyoxylic acid |
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