CN111116526A - Method for preparing furfuryl alcohol by catalyzing hydrogenation of bio-based furfural through MOF-based catalyst - Google Patents
Method for preparing furfuryl alcohol by catalyzing hydrogenation of bio-based furfural through MOF-based catalyst Download PDFInfo
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- CN111116526A CN111116526A CN201911296598.2A CN201911296598A CN111116526A CN 111116526 A CN111116526 A CN 111116526A CN 201911296598 A CN201911296598 A CN 201911296598A CN 111116526 A CN111116526 A CN 111116526A
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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
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Abstract
The invention discloses a method for preparing furfuryl alcohol by catalyzing hydrogenation of bio-based furfural through an MOF (metal organic framework) based catalyst, which comprises the steps of taking furfural as a substrate, taking low-polyhydric alcohol as a reaction medium and a hydrogenation reagent, taking a porous carbon-supported non-noble metal as a heterogeneous catalyst, filling nitrogen into a high-pressure kettle reactor for protection, and stirring and reacting for 4-48 hours at 100-180 ℃ to directly generate a product furfuryl alcohol. The porous carbon supported non-noble metal catalytic material is a porous carbon supported Mn catalyst obtained by pyrolyzing Mn-MOF at high temperature in an inert atmosphere. Compared with the prior art, the method has the advantages of simple catalyst preparation and easy separation and recovery, and the catalytic system has mild reaction conditions, high efficiency and environmental protection, and has high selectivity and yield.
Description
Technical Field
The invention belongs to the field of biomass catalysis, and particularly relates to a method for preparing furfuryl alcohol by catalyzing hydrogenation of bio-based furfural by using an MOF (metal organic framework) based non-noble metal catalyst.
Background
Furfural is an industrially unsaturated organic chemical prepared from carbohydrates, with a global yield of about 30 million tons per year, and the maximum yield in china, which accounts for about two thirds. The furfural can be obtained from various agricultural and sideline products, and particularly can be obtained by utilizing production waste materials, such as corn cobs, wheat bran of oat and wheat, and the like. Furfuryl alcohol is one of the most valuable derivatives of furfural, with 65% of the furfural yield being used to make furfuryl alcohol. The selective hydrogenation of furfural to prepare furfuryl alcohol is a very important reaction in the hydrogenation process of furfural, and is receiving increasing attention (chemical world, 2013, (12): 740). In 1929, first reported by gas phase process using Cu/SiO2 as catalyst [ U.S. patent, 1, 739, 919[ P ].1929-12-17 ], followed by Nemours in 1937 using copper chromite as catalyst and obtaining the related patent [ U.S. patent, 2, 077, 422[ P ].1937-4-20 ]. The catalytic hydrogenation method in China mainly comprises liquid-phase catalytic hydrogenation, the reaction temperature is 190-210 ℃, the pressure is 5.9-7.6 MPa, and Cu-Cr oxides are mainly used as catalysts [ industrial catalysis, 2005, 13 (10): 47-50]. Cu-Cr catalysts have been in history for over fifty years as the most successful commercial catalysts for current furfural hydrogenation processes. However, since the Cu-Cr catalyst is expensive, the catalyst is difficult to regenerate, and the toxicity of chromium is high and the pollution is serious, the research on the furfural hydrogenation catalyst is more focused on the chromium-free catalyst. In addition, noble metal catalysts such as Pt, Pd, Ru, Au, etc. are also present in the process of preparing furfuryl alcohol by catalytic hydrogenation of furfural. Although the present furfural selective hydrogenation for preparing furfuryl alcohol is industrialized, research hot spots are still focused on developing high-efficiency non-noble metal catalysts.
Conventional hydrogen sources are primarily derived from high pressure hydrogen gas, but can have many adverse effects, such as expensive price, low solubility, complex reactor design, and difficult transport. Transfer hydrogenation reactions using organic compounds (alcohols or acids) as hydrogen donors or sources have been gaining increasing attention from researchers.
In view of the above, the present inventors have made extensive studies on the above-mentioned drawbacks of the prior art, and have made this invention.
Disclosure of Invention
Technical problem to be solved
Aiming at the defects of the prior art, the invention provides a porous carbon supported non-noble metal catalyst prepared by taking MOF as a precursor through high-temperature pyrolysis, which has the advantages of simple preparation and uniform metal dispersion, can remarkably improve the stability and prevent metal particles from agglomerating, and utilizes alcohols as a hydrogen source and a reaction solvent to catalyze the hydrogenation of bio-based furfural to prepare furfuryl alcohol, in order to overcome the problems of high pressure danger of hydrogen, complicated preparation of metal catalysts and easy polymerization of metal catalysts in the prior art of preparing furfuryl alcohol by utilizing hydrogen to catalyze the hydrogenation of furfural.
(II) technical scheme
In order to achieve the purpose, the invention is realized by the following technical scheme:
a method for preparing furfuryl alcohol by catalyzing hydrogenation of bio-based furfural through an MOF (metal organic framework) based catalyst comprises the steps of taking furfural as a substrate, taking low-polyhydric alcohol as a reaction medium and a hydrogenation reagent, taking a porous carbon-supported non-noble metal as a heterogeneous catalyst, filling nitrogen into a high-pressure kettle reactor for protection, and stirring and reacting for 4-48 hours at 100-180 ℃ to directly generate a product furfuryl alcohol.
In order to further optimize the technical scheme, one solvent of methanol, ethanol, isopropanol, 1-butanol and 2-butanol is used as a reaction medium and a hydrogenation reagent, and the volume of the solvent is 5-15 ml.
In order to further optimize the technical scheme, the reaction concentration of the furfural is preferably 0.1-0.5 mmol/ml.
In order to further optimize the technical scheme, the reaction temperature is preferably 130-150 ℃; the reaction time is preferably 6-8 h.
In order to further optimize the technical scheme, the porous carbon supported non-noble metal Mn catalytic material is a porous carbon supported non-noble metal manganese catalyst obtained by pyrolyzing Mn MOF at high temperature in an inert atmosphere. Performing high-temperature carbonization at 900 ℃ by using a tubular furnace on Mn MOF (Wangying, etc., China science, edition B: chemistry, 2009, 39 (10): 1159) precursor, wherein the carbonized gas flow is selected from one of nitrogen and argon, the gas flow rate is 1-20 ml/min, and the carbonization time is 18 h; and cooling to room temperature to obtain the corresponding porous carbon supported metal catalytic material Mn/C-T (T is the calcining temperature).
In order to further optimize the technical scheme, the carbonization reaction temperature of the porous carbon supported non-noble metal manganese catalyst is preferably 600-700 ℃; the reaction time is preferably 2-4 h.
In order to further optimize the technical scheme, argon is preferably selected as the inert atmosphere for carbonizing the porous carbon-supported non-noble metal manganese catalyst, and the gas flow rate is preferably 5-10 ml/min.
(III) advantageous effects
The method for preparing furfuryl alcohol by catalyzing hydrogenation of bio-based furfural by using the MOF-based catalyst is a transfer hydrogenation reaction by using an organic compound (alcohol or acid) as a hydrogen donor or a hydrogen source, and a considerable part of alcohol (such as methanol, ethanol and the like) can be obtained from biomass conversion [ Chemical Reviews, 1985, 85 (2): 129]. Compared with hydrogen, the method has the advantages of low cost, convenient storage and transportation, safety and the like by using alcohol as a hydrogen source. In addition, there are two additional advantages to using alcohols as the hydrogen source: in the reaction system, alcohol is used as a reaction hydrogen source and a reaction solvent, so that the reaction system is simple; after hydrogen donation by alcohols, carbonyl compounds are formed, which can be separated by simple distillation and subsequently used as starting or auxiliary chemicals for the production of high value-added chemicals [ Chemical Society Reviews, 2006, 35 (3): 226].
Therefore, the invention provides a cheap, efficient, simple and fast prepared non-noble metal catalyst, which is used for catalyzing the hydrogenation of bio-based furfural to prepare furfuryl alcohol by using alcohols as a hydrogen source and a reaction solvent.
The method has the following beneficial effects: the method is characterized in that the porous carbon supported non-noble metal manganese composite catalytic material is prepared by adopting a method of pyrolyzing Mn-MOF at high temperature, has the advantages of simplicity, convenience and uniform metal dispersion, can be recycled and reused, and has practical significance.
In the application of catalyzing the hydrogenation of the bio-based furfural to prepare furfuryl alcohol, the invention utilizes alcohols as a hydrogen source and a reaction solvent, belongs to an environment-friendly green process, is beneficial to environmental protection, and also has the advantage of simple reaction system.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a transmission electron microscope image of the composite material Mn/C-600 of the present invention;
FIG. 2 is a powder XPS diffractogram of the composite Mn/C-600 of the present invention;
FIG. 3 is a powder X-ray diffraction pattern of the Mn/C-T composite material of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to fig. 1, fig. 2, and fig. 3 in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The present invention will be described in further detail with reference to examples and specific embodiments.
Example 1
1. Preparation of porous carbon supported non-noble metal catalyst
The porous carbon supported non-noble metal Mn catalytic material is a porous carbon supported non-noble metal manganese catalyst obtained by pyrolyzing Mn-MOF at high temperature in an inert atmosphere. Performing high-temperature carbonization on Mn-MOF (Wangying, etc., China science B edition: 2009, 39 (10): 1159) precursors at 600 ℃ by using a tube furnace, wherein the carbonization gas flow is argon, the gas flow rate is 5ml/min, and the carbonization time is 4 h; and cooling to room temperature to obtain the corresponding nitrogen-doped porous carbon loaded metal catalytic material Mn/C-600.
2. Furfuryl alcohol prepared by hydrogenation of furfural under catalysis of porous carbon-supported non-noble metal Mn catalyst
(1) Putting 50mg of porous carbon supported non-noble metal Mn catalyst Mn/C-600 into a 25ml high-pressure autoclave reactor, adding 1mmol of furfural and 5ml of isopropanol, introducing 2MPa of nitrogen for protection, stirring at 140 ℃, and reacting for 8 h. After the reaction, the selectivity of furfuryl alcohol was 99.5% and the yield was 97.7% as determined by gas chromatography.
(2) And (2) filtering reaction liquid, washing the recovered porous carbon supported non-noble metal Mn catalyst with isopropanol for three times, adding furfural and isopropanol, and performing a circular catalysis experiment under the reaction condition in the step (1). The furfuryl alcohol selectivity was 99.3% and the yield was 96.9% as determined by gas chromatography.
Example 2
1. Preparation of porous carbon supported non-noble metal catalyst
The porous carbon supported non-noble metal Mn catalytic material is a porous carbon supported non-noble metal manganese catalyst obtained by pyrolyzing Mn-MOF at high temperature in an inert atmosphere. Performing high-temperature carbonization on Mn-MOF (Wangying, etc., China science B edition: 2009, 39 (10): 1159) precursors at 600 ℃ by using a tube furnace, wherein the carbonization gas flow is argon, the gas flow rate is 5ml/min, and the carbonization time is 4 h; and cooling to room temperature to obtain the corresponding nitrogen-doped porous carbon loaded metal catalytic material Mn/C-600.
2. Furfuryl alcohol prepared by hydrogenation of furfural under catalysis of porous carbon-supported non-noble metal Mn catalyst
(1) Putting 50mg of porous carbon supported non-noble metal Mn catalyst Mn/C-600 into a 25ml high-pressure autoclave reactor, adding 0.5mmol of furfural and 5ml of isopropanol, introducing 2MPa of nitrogen for protection, stirring at 140 ℃, and reacting for 8 h. After the reaction, the selectivity of furfuryl alcohol was 99.8% and the yield was 99.6% as determined by gas chromatography.
(2) And (2) filtering reaction liquid, washing the recovered porous carbon supported non-noble metal Mn catalyst with isopropanol for three times, adding furfural and isopropanol, and performing a circular catalysis experiment under the reaction condition in the step (1). The furfuryl alcohol selectivity was 99.4% and the yield was 99.4% as determined by gas chromatography.
Example 3
1. Preparation of porous carbon supported non-noble metal catalyst
The porous carbon supported non-noble metal Mn catalytic material is a porous carbon supported non-noble metal manganese catalyst obtained by pyrolyzing Mn-MOF at high temperature in an inert atmosphere. Performing high-temperature carbonization on Mn-MOF (Wangying, etc., China science B edition: 2009, 39 (10): 1159) precursors at 600 ℃ by using a tube furnace, wherein the carbonization gas flow is argon, the gas flow rate is 10ml/min, and the carbonization time is 3 h; and cooling to room temperature to obtain the corresponding nitrogen-doped porous carbon loaded metal catalytic material Mn/C-600.
2. Furfuryl alcohol prepared by hydrogenation of furfural under catalysis of porous carbon-supported non-noble metal Mn catalyst
(1) Putting 50mg of porous carbon supported non-noble metal Mn catalyst Mn/C-600 into a 25ml high-pressure autoclave reactor, adding 2mmol of furfural and 10ml of isopropanol, introducing 2MPa of nitrogen for protection, stirring at 150 ℃, and reacting for 8 h. After the reaction, the selectivity of furfuryl alcohol was 99.6% and the yield was 98.7% as determined by gas chromatography.
(2) And (2) filtering reaction liquid, washing the recovered porous carbon supported non-noble metal Mn catalyst with isopropanol for three times, adding furfural and isopropanol, and performing a circular catalysis experiment under the reaction condition in the step (1). The furfuryl alcohol selectivity was 99.1% and the yield was 96.9% as determined by gas chromatography.
Example 4
1. Preparation of porous carbon supported non-noble metal catalyst
The porous carbon supported non-noble metal Mn catalytic material is a porous carbon supported non-noble metal manganese catalyst obtained by pyrolyzing Mn-MOF at high temperature in an inert atmosphere. Performing high-temperature carbonization on Mn-MOF (Wangying, etc., China science B edition: 2009, 39 (10): 1159) precursors at 600 ℃ by using a tube furnace, wherein the carbonization gas flow is argon, the gas flow rate is 10ml/min, and the carbonization time is 3 h; and cooling to room temperature to obtain the corresponding nitrogen-doped porous carbon loaded metal catalytic material Mn/C-600.
2. Furfuryl alcohol prepared by hydrogenation of furfural under catalysis of porous carbon-supported non-noble metal Mn catalyst
(1) Putting 50mg of porous carbon supported non-noble metal Mn catalyst Mn/C-600 into a 25ml high-pressure autoclave reactor, adding 1mmol of furfural and 10ml of isopropanol, introducing 2MPa of nitrogen for protection, stirring at 150 ℃, and reacting for 8 h. After the reaction, the selectivity of furfuryl alcohol was 99.6% and the yield was 98.4% as determined by gas chromatography.
(2) And (2) filtering reaction liquid, washing the recovered porous carbon supported non-noble metal Mn catalyst with isopropanol for three times, adding furfural and isopropanol, and performing a circular catalysis experiment under the reaction condition in the step (1). The furfuryl alcohol selectivity was 99.2% and the yield was 97.9% as determined by gas chromatography.
The method for preparing furfuryl alcohol by hydrogenating the bio-based furfural through the MOF-based catalyst adopts a method for pyrolyzing Mn-MOF at high temperature to prepare the porous carbon-supported non-noble metal manganese composite catalytic material, has the advantages of simplicity, convenience and uniform metal dispersion, can be recycled and reused, and has practical significance.
In the application of catalyzing the hydrogenation of the bio-based furfural to prepare furfuryl alcohol, the invention utilizes alcohols as a hydrogen source and a reaction solvent, belongs to an environment-friendly green process, is beneficial to environmental protection, and also has the advantage of simple reaction system.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various changes and modifications can be made without departing from the inventive concept of the present invention, and these changes and modifications are all within the scope of the present invention.
Claims (7)
1. A method for preparing furfuryl alcohol by catalyzing hydrogenation of bio-based furfural by an MOF-based catalyst is characterized by comprising the following steps: the method comprises the steps of taking furfural as a substrate, taking low-polyol as a reaction medium and a hydrogenation reagent, taking a porous carbon supported non-noble metal as a heterogeneous catalyst, and stirring to react for 4-48 hours at the temperature of T00-180 ℃ to directly generate a product furfuryl alcohol.
2. The method for preparing furfuryl alcohol by the hydrogenation of bio-based furfural through the MOF-based catalyst according to claim 1, wherein the MOF-based catalyst comprises: one solvent of methanol, ethanol, isopropanol, 1-butanol and 2-butanol is used as a reaction medium and a hydrogenation reagent, and the volume of the solvent is 5-15 ml.
3. The method for preparing furfuryl alcohol by the hydrogenation of bio-based furfural through the MOF-based catalyst according to claim 1, wherein the MOF-based catalyst comprises: the reaction concentration of the furfural is preferably 0.1-0.5 mmol/ml.
4. The method for preparing furfuryl alcohol by the hydrogenation of bio-based furfural through the MOF-based catalyst according to claim 1, wherein the MOF-based catalyst comprises: the reaction temperature is preferably 130-150 ℃; the reaction time is preferably 6-8 h.
5. The method for preparing furfuryl alcohol by the hydrogenation of bio-based furfural through the MOF-based catalyst according to claim 1, wherein the MOF-based catalyst comprises: the porous carbon supported non-noble metal Mn catalytic material is a porous carbon supported non-noble metal catalyst obtained by pyrolyzing Mn-MOF at high temperature in an inert atmosphere. Performing high-temperature carbonization at 900 ℃ by using a tubular furnace on Mn-MOF (Wangying, etc., China science, edition B: chemistry, 2009, 39 (10): 1159) precursors, wherein the carbonized gas flow is selected from one of nitrogen and argon, the gas flow rate is 1-20 ml/min, and the carbonization time is 18 h; after cooling to room temperature, the corresponding porous carbon supported metal catalytic material Mn/C-T can be obtained (T is the calcining temperature).
6. The method for preparing furfuryl alcohol by the hydrogenation of bio-based furfural through the MOF-based catalyst according to claim 1, wherein the MOF-based catalyst comprises: the reaction temperature is preferably 600-700 ℃; the reaction time is preferably 2-4 h.
7. The method for preparing furfuryl alcohol by the hydrogenation of bio-based furfural through the MOF-based catalyst according to claim 1, wherein the MOF-based catalyst comprises: argon is preferably selected as the inert atmosphere, and the gas flow rate is preferably 5-10 ml/min.
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