CN112371150B - Nickel-aluminum bimetal nitrogen-carbon doped catalyst, preparation method thereof and application thereof in catalyzing levulinic acid hydrogenation to prepare gamma-valerolactone - Google Patents
Nickel-aluminum bimetal nitrogen-carbon doped catalyst, preparation method thereof and application thereof in catalyzing levulinic acid hydrogenation to prepare gamma-valerolactone Download PDFInfo
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
Abstract
The invention discloses a nickel-aluminum bimetallic nitrogen-carbon doped catalyst, a preparation method thereof and application thereof in catalyzing levulinic acid to prepare gamma-valerolactone through hydrogenation. The Ni-Al-NC non-noble metal nitrogen-carbon doped catalyst is prepared based on a nitrogen-carbon doping principle derived from a metal-organic framework structure, has excellent performance, can use water as a solvent, and can efficiently catalyze and hydrogenate levulinic acid to reduce gamma-valerolactone under mild conditions.
Description
Technical Field
The invention relates to the technical field of organic compounds, in particular to preparation of gamma-valerolactone.
Background
Due to a series of environmental problems caused by the development and utilization of fossil resources and the non-regenerability of fossil resources, people are prompted to develop and utilize renewable resources to realize sustainable development of social economy. Biomass energy, second only to coal, petroleum and natural gas, is the only renewable carbon resource, and is receiving increasing attention from researchers. A range of high value-added chemicals, biofuels and materials can be obtained from biomass by means of chemical conversion of biomass. Wherein, the biomass-based platform compound gamma-valerolactone has higher boiling point (207 ℃), flash point (96 ℃), higher energy density and lower saturated vapor pressure, thus being a gasoline and diesel oil oxygenator and fuel additive with excellent performance; gamma valerolactone can also be used as a flavor and food additive, and a green solvent; the gamma-valerolactone can also be used as a raw material to convert and prepare various chemicals with high added values and monomers of high molecular polymeric materials.
It is known that levulinic acid can be obtained after cellulose biological hyaluronic acid is subjected to catalytic hydrolysis, and gamma-valerolactone can be synthesized by reducing the levulinic acid through catalytic hydrogenation, which is the gamma-valerolactone synthesis way with the most application prospect at present. By passingThe non-noble metal catalyst can be used for catalyzing levulinic acid to synthesize gamma valerolactone under mild reaction conditions, so that the production cost of the gamma valerolactone can be effectively reduced, and the industrial large-scale production of the gamma valerolactone can be promoted. However, the conventional non-noble metal catalyst usually needs an organic solvent such as 1, 4-dioxane or alcohol as a reaction medium. It should be noted that these organic solvents are expensive in raw materials and management, and have a potential risk of environmental pollution during their use. Compared with the prior art, water is a cheap and green solvent, and if levulinic acid can be efficiently catalyzed in a water phase to be subjected to hydrogenation reduction to synthesize gamma valerolactone, the industrial production of the gamma valerolactone is greatly promoted. However, since levulinic acid has stronger acidity in the aqueous phase, carboxylic acid groups in levulinic acid molecules have the advantage of competitive adsorption on the surface of the catalyst relative to carbonyl groups, and the catalytic efficiency of levulinic acid hydrogenation in the aqueous phase for synthesizing gamma-valerolactone is generally low. At present, only a small part of noble metal catalysts can efficiently catalyze levulinic acid to reduce and synthesize gamma-valerolactone in a water phase system under mild conditions. However, the noble metal catalyst has high cost, so that the preparation cost of the gamma-valerolactone is greatly increased, and the industrial production of the gamma-valerolactone is not facilitated. The activity of the prior non-noble metal catalyst for catalyzing the hydrogenation of levulinic acid in an aqueous phase is poor, and the prior non-noble metal catalyst can effectively catalyze the hydrogenation of the levulinic acid under the severe catalysis condition (>200℃，>3MPa H2And 2-12 h). Therefore, the development of a high-efficiency stable non-noble metal catalyst for realizing the high-efficiency hydrogenation reduction of levulinic acid in a water phase under mild conditions becomes a technical difficulty for the economic large-scale production of gamma-valerolactone.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a nickel-aluminum bimetallic nitrogen-carbon doped catalyst, a preparation method thereof and application thereof in catalyzing levulinic acid to prepare gamma-valerolactone through hydrogenation. The nitrogen-carbon doped nickel-aluminum bimetallic catalyst provided by the invention can efficiently catalyze levulinic acid to hydrogenate and synthesize gamma-valerolactone in a water phase under mild conditions.
One of the technical schemes adopted by the invention for solving the technical problems is as follows:
a preparation method of a nickel-aluminum bimetallic nitrogen-carbon doped catalyst comprises the steps of mixing a methanol solution containing nickel nitrate and aluminum nitrate with a methanol solution containing 2-methylimidazole, reacting for 3-5 hours at 115-125 ℃, carrying out solid-liquid separation, drying and grinding a solid part, and calcining for 2-4 hours at 500-900 ℃ in a protective gas to obtain the nickel-aluminum bimetallic nitrogen-carbon doped catalyst.
The catalyst is marked as NiaAlb-NC-T, wherein a represents the molar proportion of nickel in the metal element in the catalyst, b represents the molar proportion of aluminum in the metal element in the catalyst, and T represents the calcination temperature for the preparation of the catalyst.
Further, the molar ratio of nickel to aluminum is 0.4-0.7: 0.3 to 0.6.
Further, the molar ratio of nickel to aluminum to 2-methylimidazole is 0.4-0.7: 0.3-0.6: 6 to 6.2.
Under the conditions, a is 0.4-0.7; b is 0.3-0.6; and T is 500-900 ℃.
Preferably, the molar ratio of nickel to aluminum is 0.5-0.6: 0.4 to 0.5; under the condition, the catalytic activity of the catalyst is better. Further, the molar ratio of nickel to aluminum to 2-methylimidazole is 0.5-0.6: 0.4-0.5: 6.05-6.15.
Preferably, the calcining temperature is 580-620 ℃. The catalyst prepared under the condition has better catalytic activity.
Further, in the methanol solution containing nickel nitrate and aluminum nitrate, the concentration of the nickel nitrate is 0.25-0.5 mol/L, and the concentration of the aluminum nitrate is 0.2-0.4 mol/L; in the methanol solution containing 2-methylimidazole, the concentration of 2-methylimidazole is 5.5-6.5 mol/L.
The second technical scheme adopted by the invention for solving the technical problems is as follows:
a nickel-aluminum bimetallic nitrogen-carbon doped catalyst prepared by the preparation method. The catalyst can be described as NiaAlb-NC-T, wherein a represents the molar proportion of nickel in the metal element in the catalyst, and a is 0.4 to 0.7; b represents the molar ratio of aluminum in the metal element in the catalyst, and b is 0.3-0.6; t represents the calcination temperature for the catalyst preparation,T＝500～900℃。
the third technical scheme adopted by the invention for solving the technical problems is as follows:
an application of the nickel-aluminum bimetallic nitrogen-carbon doped catalyst in preparation of gamma-valerolactone.
The fourth technical scheme adopted by the invention for solving the technical problems is as follows:
the method for preparing gamma-valerolactone by using the nickel-aluminum bimetallic nitrogen-carbon doped catalyst comprises the steps of mixing levulinic acid with water, adding the nickel-aluminum bimetallic nitrogen-carbon doped catalyst, and reacting in hydrogen under a sealed condition, wherein the reaction temperature is 120-190 ℃, the reaction time is 4-9 h, and the hydrogen pressure is 0.5-4 MPa.
Preferably, in the raw materials for preparing the nickel-aluminum bimetallic nitrogen-carbon doped catalyst, the molar ratio of nickel to aluminum is 0.5-0.6: 0.4-0.5 (further, the molar ratio of nickel, aluminum and 2-methylimidazole is 0.5-0.6: 0.4-0.5: 6.05-6.15), and the calcination temperature in the preparation process is 580-620 ℃; the reaction temperature for preparing the gamma-valerolactone by the catalysis of the nickel-aluminum bimetallic nitrogen-carbon doped catalyst is 148-152 ℃, the reaction time is 5-8 h, and the hydrogen pressure is 0.8-1.2 MPa. Under the conditions, the yield of the gamma-valerolactone can exceed 90 percent. More preferably, the reaction time is 6-8 h, and the yield of the gamma-valerolactone can exceed 95%.
In addition, in the raw materials for preparing the nickel-aluminum bimetallic nitrogen-carbon doped catalyst, the molar ratio of nickel to aluminum is 0.5-0.6: 0.4-0.5 (the molar ratio of nickel, aluminum and 2-methylimidazole is 0.5-0.6: 0.4-0.5: 6.05-6.15), and the calcination temperature in the preparation process is 580-620 ℃; the reaction temperature for preparing gamma-valerolactone by catalysis of the nickel-aluminum bimetallic nitrogen-carbon doped catalyst is 158-162 ℃, the reaction time is 4.5-5.5 h, and the hydrogen pressure is 3.5-4 MPa, or the reaction temperature for preparing gamma-valerolactone by catalysis of the nickel-aluminum bimetallic nitrogen-carbon doped catalyst is 170-180 ℃, the reaction time is 4.5-5.5 h, and the hydrogen pressure is 0.8-1.2 MPa, under the above conditions, the yield of gamma-valerolactone is about 90-90.3%.
The equipment, reagents, processes, parameters and the like related to the invention are conventional equipment, reagents, processes, parameters and the like except for special description, and no embodiment is needed.
All ranges recited herein include all point values within the range.
As used herein, "about" or "about" and the like refer to a range or value within plus or minus 20 percent of the stated range or value.
In the invention, the room temperature, namely the normal environment temperature, can be 10-30 ℃.
Compared with the background technology, the technical scheme has the following advantages:
1. the invention designs a nitrogen-carbon doped nickel-aluminum bimetallic catalyst which can efficiently catalyze levulinic acid to hydrogenate and synthesize gamma-valerolactone in a water phase under mild conditions. 2-methylimidazole, Ni and Al metal salt are used to form a metal-organic framework structure precursor, and the precursor is calcined to obtain the nitrogen-carbon doped Ni-Al bimetallic catalyst. The catalyst has high catalytic activity, and is at 150 deg.C and 1MPa H2Under the catalytic reaction condition of (2), the yield of the gamma-valerolactone can exceed 95 percent. While other non-noble metal catalysts reported today typically require 200 ℃ and 3MPa H2The above reaction conditions can achieve similar catalytic effects.
2. The Ni-Al-NC non-noble metal nitrogen-carbon doped catalyst is prepared based on a nitrogen-carbon doping principle derived from a metal-organic framework structure, has excellent performance, can use water as a solvent, and can efficiently catalyze and hydrogenate levulinic acid to reduce gamma-valerolactone under mild conditions.
Detailed Description
The present invention will be described in detail with reference to the following examples:
examples 1 to 5
3.20g (0.011mol) of nickel nitrate hexahydrate and 3.375g (0.009mol) of aluminum nitrate nonahydrate were dissolved in 30mL of methanol, and 10g of 2-methylimidazole was dissolved in 20mL of methanol; mixing and stirring the two parts of methanol solution, reacting for 4 hours at 120 ℃, and separating to obtain solid precipitate; grinding the dried solid into powder, and forging at 500 deg.C, 600 deg.C, 700 deg.C, 800 deg.C, and 900 deg.C respectively in nitrogen atmosphereAnd sintering for 3 hours to obtain the nickel-aluminum-nitrogen-carbon doped catalyst. The catalysts are respectively marked as Ni0.55Al0.45-NC-500、Ni0.55Al0.45-NC-600、Ni0.55Al0.45-NC-700、Ni0.55Al0.45-NC-800、Ni0.55Al0.45-NC-900。
Into a 100mL autoclave were charged 0.5g of levulinic acid and 20g of water (2.5 wt%), followed by addition of 0.3g of Ni0.55Al0.45-NC-500、Ni0.55Al0.45-NC-600、Ni0.55Al0.45-NC-700、Ni0.55Al0.45-NC-800、Ni0.55Al0.45And (3) sealing the reaction kettle by using NC-900 as a catalyst, introducing hydrogen to enable the pressure to be 4MPa, mechanically stirring, heating to 160 ℃ and keeping for 5 hours, cooling to room temperature after the reaction is finished, sampling and detecting, wherein the detection results are listed as the serial numbers 1-5 in the table 1.
Example 6
2.33g (0.008mol) of nickel nitrate hexahydrate and 4.5g (0.012mol) of aluminum nitrate nonahydrate were dissolved in 30mL of methanol, and 10g of 2-methylimidazole was dissolved in 20mL of methanol; mixing and stirring the two parts of methanol solution, reacting for 4 hours at 120 ℃, and separating to obtain solid precipitate; grinding the dried solid into powder, and then calcining the powder for 3 hours at the temperature of 600 ℃ in the nitrogen atmosphere to obtain the nickel-aluminum-nitrogen-carbon doped catalyst. The above catalyst is denoted as Ni0.4Al0.6-NC-600。
A100 mL autoclave was charged with 0.5g levulinic acid and 20g water (2.5 wt%), followed by 0.3g Ni0.4Al0.6NC-600 as a catalyst, sealing the reaction kettle, introducing hydrogen to make the pressure of the reaction kettle be 4MPa, mechanically stirring, heating to 160 ℃ and keeping for 5 hours, cooling to room temperature after the reaction is finished, sampling and detecting, wherein the detection result is shown as serial number 6 in Table 1.
Example 7
3.20g (0.011mol) of nickel nitrate hexahydrate and 3.375g (0.009mol) of aluminum nitrate nonahydrate were dissolved in 30mL of methanol, and then 10g of 2-methylimidazole was dissolved in 20mL of methanol; mixing the two methanol solutions, stirring, reacting at 120 deg.C for 4 hr, and separating to obtain solid precipitatePrecipitating; grinding the dried solid into powder, and then calcining the powder for 3 hours at the temperature of 600 ℃ in the nitrogen atmosphere to obtain the nickel-aluminum-nitrogen-carbon doped catalyst. The above catalyst is labeled as: ni0.55Al0.45-NC-600。
A100 mL autoclave was charged with 0.5g levulinic acid and 20g water (2.5 wt%), followed by 0.3g Ni0.55Al0.45NC-600 as a catalyst, sealing the reaction kettle, introducing hydrogen to make the pressure of the reaction kettle be 4MPa, mechanically stirring, heating to 160 ℃ and keeping for 5 hours, cooling to room temperature after the reaction is finished, sampling and detecting, wherein the detection result is shown as a serial number 7 in Table 1.
Example 8
4.10g (0.014mol) of nickel nitrate hexahydrate and 2.25g (0.006mol) of aluminum nitrate nonahydrate were dissolved in 30mL of methanol, and then 10g of 2-methylimidazole was dissolved in 20mL of methanol; mixing and stirring the two parts of methanol solution, reacting for 4 hours at 120 ℃, and separating to obtain solid precipitate; grinding the dried solid into powder, and then calcining the powder for 3 hours at the temperature of 600 ℃ in the nitrogen atmosphere to obtain the nickel-aluminum-nitrogen-carbon doped catalyst. The above catalyst is labeled as: ni0.7Al0.3-NC-600。
A100 mL autoclave was charged with 0.5g levulinic acid and 20g water (2.5 wt%), followed by 0.3g Ni0.7Al0.3NC-600 as a catalyst, sealing the reaction kettle, introducing hydrogen to make the pressure of the reaction kettle be 4MPa, mechanically stirring, heating to 160 ℃ and keeping for 5 hours, cooling to room temperature after the reaction is finished, sampling and detecting, wherein the detection result is shown as a serial number 8 in the table 1.
Examples 9 to 13
3.20g (0.011mol) of nickel nitrate hexahydrate and 3.375g (0.009mol) of aluminum nitrate nonahydrate were dissolved in 30mL of methanol, and then 10g of 2-methylimidazole was dissolved in 20mL of methanol; mixing and stirring the two parts of methanol solution, reacting for 4 hours at 120 ℃, and separating to obtain solid precipitate; grinding the dried solid into powder, and then calcining the powder for 3 hours at the temperature of 600 ℃ in the nitrogen atmosphere to obtain the nickel-aluminum-nitrogen-carbon doped catalyst. The above catalyst is labeled as: ni0.55Al0.45-NC-600。
To a 100mL autoclave was added 0.5g of acetopropylAcid and 20g of water (2.5 wt.%), 0.3g of Ni was added0.55Al0.45And (3) sealing the reaction kettle by using NC-600 as a catalyst, introducing hydrogen to ensure that the pressure is 0.5MPa, 1MPa, 2MPa, 3MPa or 4MPa, mechanically stirring, heating to 160 ℃ and keeping for 5 hours, cooling to room temperature after the reaction is finished, sampling and detecting, wherein the detection result is listed as the serial number of 9-13 in the table 1.
Examples 14 to 20
3.20g (0.011mol) of nickel nitrate hexahydrate and 3.375g (0.009mol) of aluminum nitrate nonahydrate were dissolved in 30mL of methanol, and then 10g of 2-methylimidazole was dissolved in 20mL of methanol; mixing and stirring the two parts of methanol solution, reacting for 4 hours at 120 ℃, and separating to obtain solid precipitate; grinding the dried solid into powder, and then calcining the powder for 3 hours at the temperature of 600 ℃ in the nitrogen atmosphere to obtain the nickel-aluminum-nitrogen-carbon doped catalyst. The above catalyst is labeled as: ni0.55Al0.45-NC-600。
A100 mL autoclave was charged with 0.5g levulinic acid and 20g water (2.5 wt%), followed by 0.3g Ni0.55Al0.45-NC-600 is used as a catalyst, the reaction kettle is sealed, hydrogen is introduced to ensure that the pressure is 1MPa, the mechanical stirring is carried out, the reaction kettle is heated to 120 ℃, 130 ℃, 140 ℃, 150 ℃, 160 ℃, 170 ℃ or 180 ℃ and is kept for 5 hours, the reaction is finished, the reaction kettle is cooled to room temperature, sampling detection is carried out, and the detection result is listed as the serial number of 14-20 in the table 1.
Examples 21 to 25
3.20g (0.011mol) of nickel nitrate hexahydrate and 3.375g (0.009mol) of aluminum nitrate nonahydrate were dissolved in 30mL of methanol, and then 10g of 2-methylimidazole was dissolved in 20mL of methanol; mixing and stirring the two parts of methanol solution, reacting for 4 hours at 120 ℃, and separating to obtain solid precipitate; grinding the dried solid into powder, and then calcining the powder for 3 hours at the temperature of 600 ℃ in the nitrogen atmosphere to obtain the nickel-aluminum-nitrogen-carbon doped catalyst. The above catalyst is labeled as: ni0.55Al0.45-NC-600。
A100 mL autoclave was charged with 0.5g levulinic acid and 20g water (2.5 wt%), followed by 0.3g Ni0.55Al0.45-NC-600 as catalyst, sealing the reaction kettle, introducing hydrogen to make the pressure of the reaction kettle be 1MPa, mechanically stirring, addingHeating to 150 ℃ and keeping for 4, 5, 6, 7 or 8 hours, cooling to room temperature after the reaction is finished, sampling and detecting, wherein the detection results are listed as serial numbers 21-25 in Table 1.
TABLE 1 test results in examples
The above description is only a preferred embodiment of the present invention, and therefore should not be taken as limiting the scope of the invention, which is defined by the appended claims and their equivalents.
Claims (8)
1. A preparation method of a nickel-aluminum bimetallic nitrogen-carbon doped catalyst for catalyzing levulinic acid hydrogenation to prepare gamma-valerolactone is characterized by comprising the following steps of: mixing a methanol solution containing nickel nitrate and aluminum nitrate with a methanol solution containing 2-methylimidazole, wherein the molar ratio of the nickel nitrate to the aluminum nitrate to the 2-methylimidazole is 0.4-0.7: 0.3-0.6: 6-6.2, reacting for 3-5 h at 115-125 ℃, carrying out solid-liquid separation, drying and grinding the solid part, and calcining for 2-4 h at 500-900 ℃ in protective gas to obtain the nickel-aluminum bimetallic nitrogen-carbon doped catalyst.
2. The method of claim 1, wherein: the molar ratio of the nickel nitrate to the aluminum nitrate is 0.5-0.6: 0.4 to 0.5.
3. The method of claim 2, wherein: the calcining temperature is 580-620 ℃.
4. The method of claim 1, wherein: in the methanol solution containing nickel nitrate and aluminum nitrate, the concentration of the nickel nitrate is 0.25-0.5 mol/L, and the concentration of the aluminum nitrate is 0.2-0.4 mol/L; in the methanol solution containing 2-methylimidazole, the concentration of 2-methylimidazole is 5.5-6.5 mol/L.
5. The nickel-aluminum bimetallic nitrogen-carbon doped catalyst for catalyzing hydrogenation of levulinic acid to prepare gamma valerolactone, prepared by the preparation method according to any one of claims 1 to 4.
6. The application of the nickel-aluminum bimetallic nitrogen-carbon doped catalyst in the preparation of gamma-valerolactone by catalyzing levulinic acid hydrogenation according to claim 5.
7. A method for preparing gamma-valerolactone by utilizing the nickel-aluminum bimetallic nitrogen-carbon doped catalyst of claim 5 to catalyze the hydrogenation of levulinic acid, is characterized by comprising the following steps: mixing levulinic acid and water, adding the nickel-aluminum bimetallic nitrogen-carbon doped catalyst, and reacting in hydrogen under a sealed condition, wherein the reaction temperature is 120-190 ℃, the reaction time is 4-9 h, and the hydrogen pressure is 0.5-4 MPa.
8. The method of claim 7, wherein: the nickel-aluminum bimetallic nitrogen-carbon doped catalyst is prepared according to the preparation method of claim 3; the reaction temperature of the nickel-aluminum bimetallic nitrogen-carbon doped catalyst for catalyzing levulinic acid to prepare gamma-valerolactone through hydrogenation is 148-152 ℃, the reaction time is 5-8 h, and the hydrogen pressure is 0.8-1.2 MPa.
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| EP3683224A1 (en) * | 2017-09-12 | 2020-07-22 | Universitat de València | Iron zeolitic imidazolate framework, production method thereof and nancomposite derived from same |
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