CN113332984B - Preparation method and application of cobalt-carbon catalyst prepared by polymerization reaction - Google Patents

Preparation method and application of cobalt-carbon catalyst prepared by polymerization reaction Download PDF

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CN113332984B
CN113332984B CN202110550292.6A CN202110550292A CN113332984B CN 113332984 B CN113332984 B CN 113332984B CN 202110550292 A CN202110550292 A CN 202110550292A CN 113332984 B CN113332984 B CN 113332984B
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cobalt
carbon catalyst
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reaction
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CN113332984A (en
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胡勋
孙恺
孙艺凡
邵月文
高国明
李庆银
张丽君
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University of Jinan
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/74—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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/08—Heat treatment
    • B01J37/082—Decomposition and pyrolysis
    • 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
    • B01J37/08—Heat treatment
    • B01J37/10—Heat treatment in the presence of water, e.g. steam
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • 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

Abstract

The invention relates to the technical field of catalysts, in particular to a preparation method and application of a cobalt-carbon catalyst prepared by polymerization reaction. The catalyst is applied to hydrogenation reaction of furfuryl alcohol in an organic solvent to prepare 1,2 pentanediol, the reaction is carried out for 10 hours at the hydrogen pressure of 8MPa and the temperature of 180 ℃, the conversion rate of the furfuryl alcohol is 100 percent, and the yield of 1,4 pentanediol is 80.1 percent.

Description

Preparation method and application of cobalt-carbon catalyst prepared by polymerization reaction
Technical Field
The invention relates to a preparation method and application of a cobalt-carbon catalyst.
Background
Furfuryl alcohol is a very useful biomass-based platform compound, has wide sources and low cost, can be used as a raw material to further prepare high-value-added chemicals such as gamma-valerolactone, 1,2 pentanediol, 1,4 pentanediol, 1,5 pentanediol and the like through hydrogenation reaction, and has important application prospects and commercial values. The existing furfuryl alcohol hydrogenation process mainly uses expensive noble metal catalysts, not only has high cost, but also is easy to inactivate in an acid reaction system, and the industrial application is greatly limited.
The carbon material has rich pore structure and good adsorption effect, and can quickly adsorb the raw materials of the hydrogenation reaction to the surface of the carbon material for the hydrogenation reaction. Meanwhile, the carbon carrier has good dispersion effect on the metal active sites, so that the carbon carrier can still keep higher dispersion under the acidic condition. The carbon material is prepared from the biomass-based derivative, the raw material source is rich and cheap, the preparation of 1,2 pentanediol from furfuryl alcohol through high-efficiency and high-selectivity catalytic conversion can be realized, and the catalyst is simple in preparation process and has a good industrial prospect.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a preparation method of a cobalt-carbon catalyst prepared by polymerization reaction and application of the cobalt-carbon catalyst in furfuryl alcohol hydrogenation reaction.
In order to achieve the purpose, the invention provides the following technical scheme:
a preparation method of a cobalt-carbon catalyst prepared by polymerization reaction comprises the following steps: uniformly mixing 0-10 parts by mass of vanillin, 0-20 parts by mass of furfural, 0-5 parts by mass of organic acid, 1-10 parts by mass of cobalt salt and 20-200 parts by mass of water, stirring the mixture for 0.5-5h, then placing the mixture into a high-pressure reaction kettle, heating the mixture for 0.5-8 hours under the nitrogen atmosphere, centrifugally washing and drying the reacted suspension, placing the dried mixture into a tubular furnace, and calcining the dried mixture for 1-8 hours at 450-800 ℃ under the hydrogen atmosphere to obtain the cobalt-carbon catalyst.
The cobalt-carbon catalyst is characterized in that the organic acid comprises one of nitroformic acid, acetic acid, propionic acid and citric acid.
The cobalt-carbon catalyst is characterized in that the cobalt salt comprises one of cobalt nitrate, cobalt acetate and cobalt chloride.
The cobalt-carbon catalyst is characterized in that the initial pressure of nitrogen is 0.1-4MPa.
The cobalt-carbon catalyst is characterized in that the calcination temperature in the hydrogen atmosphere is 450-800 ℃, and the calcination time is 1-8h.
The application of the cobalt-carbon catalyst is characterized in that: the catalyst is applied to the hydrogenation reaction of furfuryl alcohol in an organic solvent to prepare 1,2 pentanediol, the temperature of the hydrogenation reaction is 130-220 ℃, the reaction time is 6-36h, and the hydrogen pressure is 3-10 MPa.
The preparation method of the invention has the following advantages and beneficial effects:
the solid acid catalyst developed by the invention is applied to the preparation of 1,2 pentanediol by furfural hydrogenation, and has the advantages of high hydrogenation activity, high stability and high selectivity.
Drawings
FIG. 1 is a flow chart of the preparation of a cobalt carbon catalyst.
Detailed Description
In order to make those skilled in the art better understand the technical solution of the present invention, the technical solution in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be obtained by a person skilled in the art without making creative efforts based on the embodiments of the present invention, shall fall within the protection scope of the present invention.
Comparative example 1
Uniformly mixing 10g of vanillin, 5g of organic acid, 5g of cobalt oxalate and 20g of water, stirring for 0.5h, putting into a high-pressure reaction kettle, flushing nitrogen with pressure of 4Mpa, heating for 0.5h, centrifugally washing the reacted suspension, drying at 100 ℃ for 10h to obtain a precursor of the cobalt-carbon catalyst, grinding the precursor into powder, putting into a tubular furnace, calcining at 450 ℃ for 8h under the atmosphere of hydrogen, cooling to room temperature, introducing nitrogen for 30min, and taking out a black solid, namely the cobalt-carbon catalyst;
adding 5g of furfuryl alcohol, 50mL of isopropanol and 0.5g of cobalt-carbon catalyst into a reaction kettle, reacting at 130 ℃ for 6h under the hydrogen pressure of 3MPa, taking out a suspension, centrifuging, taking a supernatant, adding acetone to dilute by 10 times, and testing by GC-MS, wherein the conversion rate of the furfuryl alcohol is 100%, and the yield of 1,4 pentanediol is 8.5%.
Comparative example 2
Uniformly mixing 6.3g of furfural, 5g of organic acid, 5g of cobalt oxalate and 20g of water, stirring for 0.5h, placing the mixture into a high-pressure reaction kettle, flushing nitrogen with pressure of 4Mpa, heating for 0.5h, centrifugally washing the reacted suspension, drying at 100 ℃ for 10h to obtain a precursor of the cobalt-carbon catalyst, grinding the precursor into powder, placing the powder into a tubular furnace, calcining at 450 ℃ for 8h under the atmosphere of hydrogen, cooling to room temperature, introducing nitrogen for 30min, and taking out a black solid, namely the cobalt-carbon catalyst;
adding 5g of furfuryl alcohol, 50mL of isopropanol and 0.5g of cobalt-carbon catalyst into a reaction kettle, reacting at 130 ℃ for 6h under the hydrogen pressure of 3MPa, taking out a suspension, centrifuging, taking a supernatant, adding acetone to dilute by 10 times, and testing by GC-MS, wherein the conversion rate of the furfuryl alcohol is 100%, and the yield of 1,2 pentanediol is 5.1%.
Example 1
Uniformly mixing 5.0g of vanillin, 3.2g of furfural, 3g of cobalt oxalate and 70g of water, stirring for 2 hours, putting the mixture into a high-pressure reaction kettle, flushing nitrogen with 3Mpa, heating for 8 hours, centrifugally washing the suspension after reaction, drying for 10 hours at 100 ℃ to obtain a precursor of the cobalt-carbon catalyst, grinding the precursor into powder, putting the powder into a tubular furnace, calcining for 4 hours at 600 ℃ under a hydrogen atmosphere, cooling to room temperature, introducing nitrogen for 30 minutes, and taking out black solid, namely the cobalt-carbon catalyst;
adding 5g of furfuryl alcohol, 50mL of isopropanol and 0.5g of cobalt-carbon catalyst into a reaction kettle, reacting at 180 ℃ for 10h under the hydrogen pressure of 8MPa, taking out a suspension, centrifuging, taking a supernatant, adding acetone to dilute by 10 times, and testing by GC-MS, wherein the conversion rate of the furfuryl alcohol is 100%, and the yield of 1,4 pentanediol is 78.0%.
Example 2
Uniformly mixing 5.0g of vanillin, 1.6g of furfural, 0.5g of organic acid, 3g of cobalt oxalate and 70g of water, stirring for 2 hours, putting into a high-pressure reaction kettle, flushing with 3Mpa of nitrogen, heating for 8 hours, centrifugally washing the reacted suspension, drying at 100 ℃ for 6 hours to obtain a precursor of the cobalt-carbon catalyst, grinding the precursor into powder, putting into a tube furnace, calcining at 700 ℃ for 3 hours under a hydrogen atmosphere, cooling to room temperature, introducing nitrogen for 30 minutes, and taking out a black solid, namely the cobalt-carbon catalyst;
10g of furfuryl alcohol, 50mL of isopropanol and 1.0g of cobalt-carbon catalyst are added into a reaction kettle, the hydrogen pressure is 6MPa, the mixture is taken out after reaction for 20 hours at 190 ℃, suspension is taken out and centrifuged, supernatant is taken, acetone is added to dilute the supernatant by 10 times, and then the supernatant is tested by GC-MS, the conversion rate of the furfuryl alcohol is 100 percent, and the yield of 1,4 pentanediol is 65.2 percent.
Example 3
Uniformly mixing 2.5g of vanillin, 3.2g of furfural, 0.5g of organic acid, 3g of cobalt oxalate and 70g of water, stirring for 2 hours, putting the mixture into a high-pressure reaction kettle, flushing 2Mpa of nitrogen, heating for 3 hours, centrifugally washing the suspension after reaction, drying for 8 hours at 100 ℃ to obtain a precursor of the cobalt-carbon catalyst, grinding the precursor into powder, putting the powder into a tubular furnace, calcining for 2 hours at 500 ℃ in a hydrogen atmosphere, cooling to room temperature, introducing nitrogen for 30 minutes, and taking out a black solid, namely the cobalt-carbon catalyst;
adding 5g of furfuryl alcohol, 50mL of isopropanol and 0.5g of cobalt-carbon catalyst into a reaction kettle, reacting at 210 ℃ for 10h under the hydrogen pressure of 6MPa, taking out a suspension, centrifuging, taking a supernatant, adding acetone to dilute by 10 times, and testing by GC-MS, wherein the conversion rate of the furfuryl alcohol is 100%, and the yield of 1,4 pentanediol is 50.5%.
Example 4
Uniformly mixing 5.0g of vanillin, 3.2g of furfural, 0.5g of organic acid, 3g of cobalt oxalate and 70g of water, stirring for 2 hours, putting the mixture into a high-pressure reaction kettle, flushing nitrogen with 3Mpa, heating for 8 hours, centrifugally washing the suspension after reaction, drying for 10 hours at 100 ℃ to obtain a precursor of the cobalt-carbon catalyst, grinding the precursor into powder, putting the powder into a tubular furnace, calcining for 4 hours at 600 ℃ under a hydrogen atmosphere, cooling to room temperature, introducing nitrogen for 30 minutes, and taking out a black solid, namely the cobalt-carbon catalyst;
adding 5g of furfuryl alcohol, 50mL of isopropanol and 0.5g of cobalt carbon catalyst into a reaction kettle, reacting at 180 ℃ for 10 hours under the hydrogen pressure of 8MPa, taking out a suspension, centrifuging, taking a supernatant, diluting by 10 times by adding acetone, and testing by GC-MS, wherein the conversion rate of the furfuryl alcohol is 100%, and the yield of 1,4 pentanediol is 80.1%.
Example 5
Uniformly mixing 10g of vanillin, 20g of furfural, 5g of organic acid, 1g of cobalt oxalate and 200g of water, stirring for 5 hours, putting into a high-pressure reaction kettle, flushing nitrogen with the pressure of 0.5Mpa, heating for 8 hours, centrifugally washing the reacted suspension, drying at 100 ℃ for 6 hours to obtain a precursor of the cobalt-carbon catalyst, grinding the precursor into powder, putting into a tubular furnace, calcining at 800 ℃ for 1 hour under the atmosphere of hydrogen, cooling to room temperature, introducing nitrogen for 30min, and taking out a black solid to obtain the cobalt-carbon catalyst;
adding 5g of furfuryl alcohol, 50mL of isopropanol and 1.0g of cobalt-carbon catalyst into a reaction kettle, reacting at 190 ℃ for 36h under the hydrogen pressure of 10MPa, taking out a suspension, centrifuging, taking a supernatant, adding acetone to dilute by 10 times, and testing by using GC-MS, wherein the conversion rate of the furfuryl alcohol is 100%, and the yield of 1,4 pentanediol is 22.7%.
Example 6
Uniformly mixing 5.0g of vanillin, 3.2g of furfural, 0.5g of organic acid, 4g of cobalt nitrate and 70g of water, stirring for 2 hours, putting into a high-pressure reaction kettle, flushing with 3Mpa of nitrogen, heating for 8 hours, centrifugally washing the reacted suspension, drying at 100 ℃ for 8 hours to obtain a precursor of the cobalt-carbon catalyst, grinding the precursor into powder, putting into a tube furnace, calcining at 550 ℃ for 5 hours under a hydrogen atmosphere, cooling to room temperature, introducing nitrogen for 30 minutes, and taking out a black solid, namely the cobalt-carbon catalyst;
adding 5g of furfuryl alcohol, 50mL of isopropanol and 0.5g of cobalt carbon catalyst into a reaction kettle, reacting at 180 ℃ for 10 hours under the hydrogen pressure of 8MPa, taking out a suspension, centrifuging, taking a supernatant, diluting by 10 times by adding acetone, and testing by GC-MS, wherein the conversion rate of the furfuryl alcohol is 100%, and the yield of 1,4 pentanediol is 77.1%.
Example 7
Uniformly mixing 5.0g of vanillin, 3.2g of furfural, 1.5g of organic acid, 4g of cobalt chloride and 70g of water, stirring for 2 hours, putting the mixture into a high-pressure reaction kettle, flushing nitrogen with 3Mpa, heating for 8 hours, centrifugally washing the suspension after reaction, drying for 8 hours at 100 ℃ to obtain a precursor of the cobalt-carbon catalyst, grinding the precursor into powder, putting the powder into a tubular furnace, calcining for 5 hours at 550 ℃ under a hydrogen atmosphere, cooling to room temperature, introducing nitrogen for 30 minutes, and taking out a black solid, namely the cobalt-carbon catalyst;
adding 5g of furfuryl alcohol, 50mL of isopropanol and 0.5g of cobalt-carbon catalyst into a reaction kettle, reacting at 180 ℃ for 10h under the hydrogen pressure of 8MPa, taking out a suspension, centrifuging, taking a supernatant, adding acetone to dilute by 10 times, and testing by GC-MS, wherein the conversion rate of the furfuryl alcohol is 100%, and the yield of 1,4 pentanediol is 77.1%.

Claims (3)

1. The application of the cobalt-carbon catalyst prepared by polymerization reaction is characterized in that: the cobalt-carbon catalyst is applied to hydrogenation reaction of furfuryl alcohol in an organic solvent to prepare 1,2 pentanediol, the temperature of the hydrogenation reaction is 130-220 ℃, the reaction time is 6-36h, and the hydrogen pressure is 3-10MPa; mixing and stirring 0-10 parts by mass of vanillin, 0-20 parts by mass of furfural, 0-5 parts by mass of organic acid, 1-10 parts by mass of cobalt salt and 20-200 parts by mass of water for 0.5-5 hours, then placing the mixture into a high-pressure reaction kettle, heating the mixture for 0.5-8 hours under the nitrogen atmosphere, centrifugally washing and drying the reacted suspension, placing the mixture into a tubular furnace, and calcining the mixture for 1-8 hours at 450-800 ℃ under the hydrogen atmosphere to obtain the cobalt-carbon catalyst; the mass part of the vanillin is not 0, and the mass part of the furfural is not 0; the organic acid comprises one of acetic acid, propionic acid and citric acid.
2. Use according to claim 1, wherein the cobalt salt comprises one of cobalt nitrate, cobalt acetate, cobalt chloride.
3. Use according to claim 1, characterized in that the initial pressure of nitrogen is 0.1-4MPa.
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CN102923687A (en) * 2011-08-11 2013-02-13 北京大学 Middle-pore carbon material and its preparation method
CN104370702A (en) * 2013-08-16 2015-02-25 中国科学院兰州化学物理研究所 Method for preparing 1,2-pentanediol by furfuryl alcohol liquid phase selectivity and hydrogenolysis
CN111087370A (en) * 2019-12-19 2020-05-01 华南理工大学 Method for preparing furfuryl alcohol by catalyzing furfural transfer hydrogenation through nitrogen-doped carbon loaded by non-noble metal
CN112403472A (en) * 2020-12-26 2021-02-26 齐鲁工业大学 Method for preparing carbon-based transition metal hydrogenation catalyst based on pyrolysis bio-oil

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