CN113292520B - Synthesis method and application of magnetic catalyst for preparing furfuryl alcohol by catalytic hydrogenation of furfural - Google Patents

Synthesis method and application of magnetic catalyst for preparing furfuryl alcohol by catalytic hydrogenation of furfural Download PDF

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CN113292520B
CN113292520B CN202110620335.3A CN202110620335A CN113292520B CN 113292520 B CN113292520 B CN 113292520B CN 202110620335 A CN202110620335 A CN 202110620335A CN 113292520 B CN113292520 B CN 113292520B
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catalyst
furfural
reaction
furfuryl alcohol
hydrogen
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CN113292520A (en
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林鹿
田野
闫贵花
陈高峰
彭志清
唐兴
孙勇
曾宪海
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Xiamen University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D307/34—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
    • C07D307/38—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 with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C07D307/44—Furfuryl alcohol
    • 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
    • B01J23/74—Iron group metals
    • B01J23/75—Cobalt
    • 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
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/847—Vanadium, niobium or tantalum or polonium
    • B01J23/8474—Niobium
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/16—Reducing
    • B01J37/18—Reducing with gases containing free hydrogen
    • 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
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention discloses a method for preparing furfuryl alcohol by catalytic hydrogenation of furfural and a magnetic catalyst thereof. The magnetic catalyst is a supported catalyst, the active component Co of the magnetic catalyst is from a corresponding non-noble metal salt solution, and the catalyst carrier is an oxide selected from oxides of Al or Nb. The catalyst is prepared by a simple excessive impregnation method, and the loading amount of the active components is 20% of the mass of the corresponding carrier. The method adopts biomass hydrolysate furfural as a raw material, commercial hydrogen as a hydrogen source and deionized water as a solvent, and the reaction time is 1-4 h at the reaction temperature of 100-140 ℃ under the hydrogen pressure of 1-2 MPa and the stirring speed of 400 rpm. Under the optimal condition, the conversion rate of the furfural is close to 100%, and the furfuryl alcohol selectivity is 96.89%. The catalyst has the advantages of simple preparation method, low price, circularity, environment-friendly catalytic system, renewable reaction substrates, mild reaction conditions, low cost and wide industrial application prospect.

Description

Synthesis method and application of magnetic catalyst for preparing furfuryl alcohol by catalytic hydrogenation of furfural
Technical Field
The invention belongs to the technical field of fine chemical engineering, in particular to a method for preparing furfuryl alcohol by catalytic hydrogenation of furfural and a magnetic catalyst thereof, and more particularly relates to a method for preparing furfuryl alcohol by liquid-phase hydrogenation of furfural by a cobalt-based single-metal catalyst.
Background
At present, furfural is prepared from biomass corncob serving as a raw material, is hydrolyzed into pentose under the action of dilute acid, and is subjected to dehydration and cyclization to obtain the produced furfural which is industrially produced, wherein about 65% of the produced furfural is used as the raw material for synthesizing furfuryl alcohol. Furfuryl alcohol is mainly used for producing synthetic fibers, constant-temperature resins, corrosion-resistant glass fibers, pesticides, foundry binders, rocket fuels, fragrances and the like, and can also be used for synthesizing important intermediate chemicals such as lysine, vitamin C, lubricants, dispersants, plasticizers, tetrahydrofurfuryl alcohol, levulinic acid and the like (K.Fulajt rova Applied Catalysis A: general,2015, 502, 78-85).
The improved Adkins catalyst is industrially adopted, and the catalyst is mainly prepared by taking ammonia water, sodium dichromate and copper nitrate as raw materials and adopting a classical precipitation method. The method is used for catalyzing selective hydrogenation of furfural to prepare furfuryl alcohol. However, such catalysts contain the carcinogen Cr ion, which not only causes injury to operators during the process of catalyst preparation and during post-deactivation disposal, but also causes serious environmental pollution (m.m., villaverde Catalysis Communications,2015, 58,6-10).
In general, in gas-phase or liquid-phase hydrogenation systems, furfural can be catalytically converted to hydrogenation to furfuryl alcohol. In view of the stability of liquid phase hydrogenation systems and the lack of need for higher hydrogen pressures and purer products, liquid phase hydrogenation systems are generally preferred (R.V. Shalma Applied Catalysis A: general,2013, 454, 127-136). Because furfural is easy to open into cyclopentanone and cyclopentanol in the water phase, the catalytic reaction of furfurol in the water solution is less studied. In particular, non-noble single metal catalysts. Although related systems have been studied, the requirements are severe and the time is long (Catalysis Today 367 (2021) 177-188).
Disclosure of Invention
Based on the background, the invention provides a simple impregnation method for preparing a single-metal catalyst from cheap non-noble metal cobalt and solid oxide, which is used for synthesizing furfuryl alcohol which is a high-added-value fine chemical product by carrying out water-phase catalytic hydrogenation on furfuraldehyde by a one-pot method. The method provides a simple, low-cost, high-efficiency, environment-friendly and industrial production method for converting the furfural into the furfuryl alcohol.
The invention provides a method for preparing furfuryl alcohol by catalytic hydrogenation of furfural, which is characterized by comprising the following steps:
adding furfural, solvent and metal catalyst into an intermittent closed high-pressure reaction kettle, and carrying out catalytic selective hydrogenation reaction under stirring;
the metal catalyst is a non-noble metal supported catalyst, wherein the catalyst carrier is Al in two metal oxides 2 O 3 、Nb 2 O 5 One of the following; the active component of the catalyst is transition metal Co; the preparation method comprises the following steps: a metal salt containing a transition metal Co (preferably Co (NO 3 ) 2 ) Adding the aqueous solution of (C) into a catalyst carrier, stirring overnight, drying in a drying oven, roasting at 400-600 ℃ for 2-6h, and reducing in a hydrogen atmosphere before use.
In a specific embodiment, the ratio of furfural to solvent is 0.2g:3 to 20ml, preferably 0.2g:5 to 15ml, more preferably: 0.2g: 5-10 ml; the dosage of the metal catalyst is 1/1 to 1/4, preferably 1/2, of the mass of the furfural, the initial pressure of the hydrogen is 1 to 2MPa, the reaction temperature is 100 to 140 ℃, preferably 110 to 130 ℃, and the reaction time is 1 to 6 hours, preferably 3 to 5 hours.
Further, after the reaction is finished, the catalyst is subjected to cold water bath and pressure relief, and after the catalyst is separated by the magnet, ethyl acetate is used for extraction.
Preferably, the solvent is deionized water.
In one embodiment, the active component loading of the metal catalyst is 20%, and the catalyst carrier is Nb 2 O 5 。
The preparation steps of the metal catalyst are as follows: the aqueous solution of metal salt containing transition metal Co is added into the catalyst carrier, stirred overnight, dried in a drying oven at 100 ℃, baked for 4 hours at 500 ℃ and reduced in hydrogen atmosphere before use. The operation mode of the reduction in the hydrogen atmosphere is that the reduction is carried out for 2 to 6 hours in a tubular furnace with the temperature of 400 to 600 ℃ and the hydrogen is preferably carried out for 4 hours in a tubular furnace with the temperature of 500 ℃ and the hydrogen is introduced.
The inventionThe preparation process includes adding metal salt water solution containing transition metal Co into catalyst carrier, stirring overnight, stoving in a drier, roasting at 400-600 deg.c for 2-6 hr, and reduction in hydrogen atmosphere before use. The catalyst carrier is Al in two metal oxides 2 O 3 、Nb 2 O 5 One of the following; the active component of the catalyst is Co (NO 3 ) 2 ·6H 2 O。
Wherein the operation mode of the reduction in the hydrogen atmosphere is to reduce in a tubular furnace with the temperature of 400-600 ℃ for 2-6h, preferably in a tubular furnace with the temperature of 500 ℃ for 4h.
Further, the invention also provides the non-noble metal supported catalyst prepared by the preparation method of the non-noble metal supported catalyst.
The non-noble single-metal catalyst is used for preparing furfuryl alcohol by liquefying and hydrogenating furfural, and deionized water is used as a solvent, so that the production cost is reduced, and the environment is protected. Low requirements on equipment, simple operation, renewable raw material furfural, high product selectivity and wide market application prospect. Compared with the catalyst for converting furfuryl alcohol by industrial furfural, the catalyst adopted by the invention has lower toxicity and reduces the harm to human bodies in industrial production environment.
The catalyst prepared from the non-noble metal is low in cost, does not need the processes of re-roasting, reduction and the like, can be directly recycled after being dried, and has the obvious advantages that the yield is basically kept unchanged.
Drawings
FIG. 1 is a non-noble single metal catalyzed Co-Nb 2 O 5 A reaction principle for preparing furfuryl alcohol by catalyzing water phase hydrogenation of furfural.
FIG. 2 is a gas chromatogram of furfuryl alcohol product by aqueous hydrogenation of furfural at a reaction temperature of 120deg.C, a reaction pressure of 2MPa, a reaction-to-liquid ratio of 0.2g/5ml, a reaction time of 4h, and a stirring speed of 400 rpm.
FIG. 3 is a mass spectrum of furfuryl alcohol product prepared by aqueous hydrogenation of furfural at 120℃and 2MPa reaction pressure, 0.2g/5ml reaction to feed ratio, 4h reaction time and 400rpm stirring speed.
FIG. 4 is a graph showing the effect of separating the metal catalyst of the present invention by a magnet after the completion of the reaction.
Detailed Description
The invention is further illustrated with reference to examples. Unless otherwise specified, reagents and equipment used in the following examples are commercially available products. The specific implementation cases are as follows:
example 1
0.004mol of Co (NO) 3 ) 2 ·6H 2 O was dissolved in 0.2mol of water, and the aqueous solution was added with 0.01mol of Al 2 O 3 After stirring overnight, drying in a drying oven at 100 ℃, roasting in a muffle furnace at 500 ℃ for 4 hours, and reducing in a tube furnace at 500 ℃ for 4 hours before use, thus obtaining the corresponding single-metal catalyst.
0.2g of furfural and 5mL of water were weighed and put into a 40mL reaction kettle, and 0.1g of catalyst (Co-Al was added 2 O 3 Wherein Al is 2 O 3 The active component is Co, and the weight percentage of the active component Co is 20 percent. The air in the kettle is replaced by hydrogen three to four times, the hydrogen is filled to the initial pressure of 2MPa, a stirring device is started at 400rpm, the reaction is carried out for 4 hours at the temperature of 120 ℃, the product is cooled, separated by a magnet, extracted by ethyl acetate, subjected to qualitative analysis by gas chromatography (GC-MS, thermo Scientific) and subjected to quantitative analysis by gas chromatography (GC, agilent 7890A). The result is that: the conversion of furfural was 99.47% and the yield of furfuryl alcohol was 64.90%.
Example 2
0.004mol of Co (NO) 3 ) 2 ·6H 2 O was dissolved in 0.2mol of water and the aqueous solution was added to 0.004mol of Nb 2 O 5 After stirring overnight, drying in a drying oven at 100 ℃, roasting at 500 ℃ for 4 hours, and reducing in a tubular furnace at 500 ℃ with hydrogen for 4 hours before use, thus obtaining the corresponding single-metal catalyst.
0.2g of furfural and 5mL of water were weighed and put into a 40mL reaction kettle, and 0.1g of catalyst (Co-Nb) 2 O 5 Wherein Nb is 2 O 5 The active component is Co, and the weight percentage of the active component Co is 20 percent. The air in the kettle is replaced by hydrogen three to four times, the hydrogen is filled to the initial pressure of 2MPa, a stirring device is started at 400rpm, the reaction is carried out for 4 hours at the temperature of 120 ℃, the product is cooled, separated by a magnet, extracted by ethyl acetate, subjected to qualitative analysis by gas chromatography (GC-MS, thermo Scientific) and subjected to quantitative analysis by gas chromatography (GC, agilent 7890A). The result is that: the conversion of furfural was 99.52% and the yield of furfuryl alcohol was 96.42%.
Example 3
The corresponding monometal catalyst was prepared as in example 2 for further use.
The reaction was carried out as in example 2 except that the reaction temperature was 100 ℃. The reaction gave the following results: the conversion of furfural was 98.52% and the yield of furfuryl alcohol was 66.72%.
Example 4
The corresponding monometal catalyst was prepared as in example 2 for further use.
The reaction was carried out as in example 2, except that the reaction temperature was 140 ℃. The reaction gave the following results: the conversion of furfural was 99.48% and the yield of furfuryl alcohol was 10.68%.
Example 5
The corresponding monometal catalyst was prepared as in example 2 for further use.
The reaction was carried out as in example 2 except that hydrogen was charged therein to an initial pressure of 1MPa. The reaction gave the following results: the conversion of furfural was 95.0% and the yield of furfuryl alcohol was 92.15%.
Example 6
The corresponding monometal catalyst was prepared as in example 2 for further use.
The reaction was carried out as in example 2, except that the reaction time was 1h. The reaction gave the following results: the conversion of furfural was 91.83% and the yield of furfuryl alcohol was 54.95%.
Example 7
The corresponding monometal catalyst was prepared as in example 2 for further use.
The reaction was carried out as in example 2, except that the reaction time was 2 hours. The result obtained by the reaction is 89.18% conversion of furfural and 44.47% yield of furfuryl alcohol.
Example 8
The corresponding monometal catalyst was prepared as in example 2 for further use.
The reaction was carried out as in example 2, except that the reaction time was 3 hours. The result obtained by the reaction is 99.20% conversion of furfural and 63.04% yield of furfuryl alcohol.
Example 9
The corresponding monometal catalyst was prepared as in example 2 for further use.
The reaction was carried out as in example 2 except that the reaction time was 6 hours. The reaction gave the following results: the conversion of furfural was 99.6% and the yield of furfuryl alcohol was 44.60%.
Example 10
The corresponding monometal catalyst was prepared as in example 2 for further use.
A reaction was conducted as described in example 2 except that 0.2g of furfural and 3mL of water were weighed and put into a 40mL reaction vessel. The reaction gave the following results: the conversion of furfural was 99.70% and the yield of furfuryl alcohol was 27.64%.
Example 11
The corresponding monometal catalyst was prepared as in example 2 for further use.
A reaction was conducted as described in example 2 except that 0.2g of furfural and 10mL of water were weighed and put into a 40mL reaction vessel. The reaction gave the following results: the conversion of furfural was 97.28% and the yield of furfuryl alcohol was 25.68%.
Example 12
The corresponding monometal catalyst was prepared as in example 2 for further use.
A reaction was conducted as described in example 2 except that 0.2g of furfural and 15mL of water were weighed and put into a 40mL reaction vessel. The reaction gave the following results: the conversion of furfural was 97.68% and the yield of furfuryl alcohol was 19.45%.
Example 13
The corresponding monometal catalyst was prepared as in example 2 for further use.
A reaction was conducted as described in example 2 except that 0.2g of furfural and 20mL of water were weighed and put into a 40mL reaction vessel. The reaction gave the following results: the conversion of furfural was 97.88% and the yield of furfuryl alcohol was 22.22%.
Example 14
The catalyst recovered from example 2 by magnet separation was washed directly with water, placed in a dry box overnight and used for the second conversion reaction. The liquefaction hydrogenation process and the test method are the same as in example 2. The result is that: the conversion of furfural was 99.55% and the yield of furfuryl alcohol was 94.77%.
The results are summarized in the following table:
TABLE 1 influence of different types of catalysts and process variables on conversion and selectivity of furfuryl alcohol prepared by aqueous hydrogenation of Furfural
According to the results of the specific examples, the metal catalyst provided by the invention can be effectively used for preparing high-added-value fine chemical furfuryl alcohol by liquid-phase hydrogenation of furfural, and can be recycled. Under the optimal conditions, namely the reaction temperature is 120 ℃, the reaction time is 4 hours, the hydrogen pressure is 2MPa, the feed-liquid ratio is 0.2/5 (g/ml), and the stirring speed is 400rpm, the conversion rate of furfural is close to 100 percent, and the yield of furfuryl alcohol is close to 97 percent.
The specific examples of the present invention are for illustrative purposes only, and the catalyst is applicable to hydrogenation reactions of furfural, furfuryl alcohol, and tetrahydrofurfuryl alcohol as substrates. It is not intended to limit the scope of the invention in any way, and a person skilled in the art can modify or change the invention according to the description above, all such modifications and changes being intended to fall within the scope of the appended claims.

Claims (1)

1. The method for preparing furfuryl alcohol by catalytic hydrogenation of furfural is characterized by comprising the following steps:
adding furfural, solvent and metal catalyst into an intermittent closed high-pressure reaction kettle, and carrying out catalytic selective hydrogenation reaction under the stirring of 400rpm, wherein the temperature of the hydrogenation reaction is 120 ℃; wherein, the initial pressure of hydrogen in hydrogenation reaction is 2MPa, and the reaction time is 4 hours; after the reaction is finished, carrying out cold water bath and pressure relief, and extracting the metal catalyst by using ethyl acetate after separating the metal catalyst by using a magnet;
the solvent is deionized water; the ratio of the furfural to the solvent is 0.2g:5ml; the dosage of the metal catalyst is 1/2 of the mass of the furfural;
the metal catalyst is non-noble metal supported catalyst Co-Nb 2 O 5 The preparation method comprises the following steps: to a metal salt Co (NO) containing a transition metal Co 3 ) 2 ·6H 2 Adding a catalyst carrier Nb into an aqueous solution of O 2 O 5 Stirring overnight, drying at 100deg.C in a drying oven, roasting at 500deg.C for 4 hr, and reducing in hydrogen atmosphere before use, wherein the loading amount of active component Co is 20wt%;
the operation mode of the reduction in the hydrogen atmosphere is that the reduction is carried out for 4 hours in a tubular furnace with the temperature of 500 ℃ and the hydrogen is introduced.
CN202110620335.3A 2021-06-03 2021-06-03 Synthesis method and application of magnetic catalyst for preparing furfuryl alcohol by catalytic hydrogenation of furfural Active CN113292520B (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102387857A (en) * 2009-03-26 2012-03-21 约翰森·马瑟公开有限公司 Method for producing a supported metal nitrate
CN106955707A (en) * 2017-04-13 2017-07-18 济南大学 A kind of cobalt-based reforming catalyst and its modification method for preparing
CN107011107A (en) * 2017-05-16 2017-08-04 中国科学技术大学 A kind of method that use load type metal catalyst prepares alcohol
CN109942378A (en) * 2019-01-25 2019-06-28 华东理工大学 A kind of method that wooden vegetable oil prepares alkylphenol and alkyl diphenol
CN110496614A (en) * 2018-05-16 2019-11-26 中国科学院大连化学物理研究所 Metallic catalyst, preparation method and the application in furfuryl alcohol is prepared in aqueous catalysis furfural hydrogenation
CN112774682A (en) * 2019-11-11 2021-05-11 中国科学院城市环境研究所 Aluminum-cobalt composite catalyst and preparation method and application thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102387857A (en) * 2009-03-26 2012-03-21 约翰森·马瑟公开有限公司 Method for producing a supported metal nitrate
CN106955707A (en) * 2017-04-13 2017-07-18 济南大学 A kind of cobalt-based reforming catalyst and its modification method for preparing
CN107011107A (en) * 2017-05-16 2017-08-04 中国科学技术大学 A kind of method that use load type metal catalyst prepares alcohol
CN110496614A (en) * 2018-05-16 2019-11-26 中国科学院大连化学物理研究所 Metallic catalyst, preparation method and the application in furfuryl alcohol is prepared in aqueous catalysis furfural hydrogenation
CN109942378A (en) * 2019-01-25 2019-06-28 华东理工大学 A kind of method that wooden vegetable oil prepares alkylphenol and alkyl diphenol
CN112774682A (en) * 2019-11-11 2021-05-11 中国科学院城市环境研究所 Aluminum-cobalt composite catalyst and preparation method and application thereof

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