CN110354886A - A kind of nitrogen-doped carbon nickel-loaded cobalt dual-metal nanocatalyst, preparation method and application - Google Patents
A kind of nitrogen-doped carbon nickel-loaded cobalt dual-metal nanocatalyst, preparation method and application Download PDFInfo
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- CN110354886A CN110354886A CN201910711234.XA CN201910711234A CN110354886A CN 110354886 A CN110354886 A CN 110354886A CN 201910711234 A CN201910711234 A CN 201910711234A CN 110354886 A CN110354886 A CN 110354886A
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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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
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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
- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
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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
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- 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 discloses a kind of methods for preparing furfuryl alcohol by furfural catalysis transfer hydrogenation.In the presence of non-precious metal catalyst and Organic Alcohol, control reaction temperature is 100-250 DEG C, and furfurol reaction object obtains furfuryl alcohol by being catalyzed transfer hydrogenation 1-24h in inert atmosphere；The catalyst is nitrogen-doped carbon supported bi-metallic nanocatalyst, which be prepared by hydrothermal synthesis method, and expression formula is XY/NC, and wherein NC is nitrogen-doped carbon carrier, and X is nickel, and Y is cobalt.Method provided by the invention is that high pressure hydrogen is replaced using Organic Alcohol as hydrogen source, and safety coefficient is high, using economic and environment-friendly non-precious metal catalyst, preparation process is simple, and low production cost, catalyst is easily isolated, good cycling stability has good industrial applications prospect.
Description
Technical field
The invention belongs to biomass catalyzing transformation technology field, it is related to a kind of nitrogen-doped carbon nickel-loaded cobalt dual-metal nanometer and urges
The method that agent and the catalyst prepare furfuryl alcohol for furfural catalysis transfer hydrogenation.
Background technique
With the consumption of fossil resource and the exacerbation of energy problem, realized using reproducible biomass resource additional to height
The conversion of value fuels and chemicals has caused the extensive concern of people.Inedible lignocellulosic material because reserves are big,
It is at low cost, to become the desirable feedstock of sustainable energy.Furfural is by lignocellulosic material by simple hydrolysis process
After obtain, be one of 12 kinds of platform chemicals that U.S. Department of Energy filters out, there is yield big, source and widely used excellent
Point.In furfural hydrogenation reaction most important product first is that furfuryl alcohol, the furfural in the annual whole world about 65% prepares chaff for production
Alcohol.Furfuryl alcohol has broad application prospects, and can be used for preparing macromolecule resin, plasticizer, fuel and wetting agent, the phenol of casting
Urea formaldehyde and Lauxite etc..
Catalysis transfer hydrogenation is an effective way of catalytic hydrogenation, and this method is using alcohol or organic acid as solvent
And hydrogen donor, activated hydrogen species are generated under the action of catalyst, and then are transferred in substrate molecule and are realized its unsaturated group
Hydrogenation process, and this process, without using high pressure hydrogen, safety coefficient is high.Furfural can be obtained by being catalyzed transfer hydrogenation
Furfuryl alcohol, current research are focused primarily upon using the single or compound noble metal catalyst of support type, metal oxide oxidation catalyst
Agent and a small number of non-precious metal catalysts, but these catalyst manufacture at high cost, preparation process complexity, and hydrogenation conditions are severe
It carves, the yield and selectivity of target product furfuryl alcohol are to be improved, and catalyst easily occurs to be lost, reunite etc. and inactivate.
Summary of the invention
The main purpose of the present invention is to provide a kind of nitrogen-doped carbon supported bi-metallic nanocatalysts.
Nitrogen-doped carbon supported bi-metallic nanocatalyst of the present invention is the system as obtained by hydrothermal synthesis method preparation
Standby step includes: that mixing that cobalt nitrate, nickel nitrate and sodium ethylene diamine tetracetate are dissolved in first alcohol and water according to a certain percentage is molten
In agent, liquid after mixing is placed in progress hydro-thermal reaction 10-48h at 180 ~ 250 DEG C of insulating box.After reaction, it passes through
It washs, be dried to obtain EDTA-CoNi metal complex presoma.The presoma is roasted in 350 ~ 650 DEG C in an inert atmosphere
1-6h to get arrive the catalyst.
The present invention also provides a kind of economic and environment-friendly methods for preparing furfuryl alcohol by furfural catalysis transfer hydrogenation.
A kind of method that furfural catalysis transfer hydrogenation prepares furfuryl alcohol: in the presence of non-precious metal catalyst and Organic Alcohol, chaff
Aldehyde reaction object obtains furfuryl alcohol by being catalyzed transfer hydrogenation in inert atmosphere；The non-precious metal catalyst is N doping
Carbon supported bi-metallic nanocatalyst, expression formula are XY/NC, and wherein NC is nitrogen-doped carbon carrier, and X is nickel, and Y is cobalt.
Reaction temperature of the present invention is 100-250 DEG C, reaction time 1-24h.
Organic Alcohol of the present invention is methanol, ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol, isobutanol or the tert-butyl alcohol, is somebody's turn to do
Organic Alcohol is as reaction dissolvent and hydrogen donor.
The mass ratio of furfural and catalyst of the present invention is 2-25:1.
The content of X is two kinds of components of 5-60wt%, X and Y of catalyst total amount in catalyst XY/NC of the present invention
Molar ratio nX:nYFor 1:(0.1-5), n represents molal quantity.
Inert reaction atmosphere of the present invention is nitrogen.
The invention has the following advantages that
1. the present invention uses Organic Alcohol to replace high pressure hydrogen, safe and environment-friendly economy as hydrogen source.
2. the present invention uses non-precious metal catalyst, realizes high activity from furfural to furfuryl alcohol and highly selective conversion from, urge
Agent preparation process is simple, low manufacture cost, is suitble to mass production.
3. catalyst is easily isolated, good cycling stability, there is good prospects for commercial application.
Specific embodiment
Embodiment 1
NiCo/NC (wherein Ni:24.1wt%, nNi:nCo=1:1) catalyst preparation: weigh respectively 6.985g cobalt nitrate,
6.979g nickel nitrate and 9.988gNa4EDTA is dissolved in 20mL methanol and 40mL deionized water in the mixed solvent.Mixing
Liquid after uniformly pours into water heating kettle, and hydro-thermal reaction is for 24 hours at 200 DEG C.After reaction, liquid in kettle centrifugation is carried out to wash
It washs, is dried in vacuum overnight at 100 DEG C to get EDTA-CoNi metal complex presoma.In an inert atmosphere by the presoma
475 DEG C of roasting 3h to get arrive NiCo/NC (wherein Ni:24.1wt%, nNi:nCo=1:1) catalyst.
Embodiment 2
NiCo/NC (wherein Ni:12.9wt%, nNi:nCo=1:3) catalyst preparation: weigh respectively 10.479g cobalt nitrate,
3.490g nickel nitrate and 9.988gNa4EDTA is dissolved in 20mL methanol and 40mL deionized water in the mixed solvent.Mixing
Liquid after uniformly pours into water heating kettle, and hydro-thermal reaction is for 24 hours at 200 DEG C.After reaction, liquid in kettle centrifugation is carried out to wash
It washs, is dried in vacuum overnight at 100 DEG C to get EDTA-CoNi metal complex presoma.In an inert atmosphere by the presoma
475 DEG C of roasting 3h to get arrive NiCo/NC (wherein Ni:12.9wt%, nNi:nCo=1:3) catalyst.
Embodiment 3
NiCo/NC (wherein Ni:31wt%, nNi:nCo=3:1) catalyst preparation: weigh respectively 3.493g cobalt nitrate,
10.469g nickel nitrate and 9.988gNa4EDTA is dissolved in 20mL methanol and 40mL deionized water in the mixed solvent.Mixed
Liquid after closing uniformly pours into water heating kettle, and hydro-thermal reaction is for 24 hours at 200 DEG C.After reaction, liquid in kettle centrifugation is carried out to wash
It washs, is dried in vacuum overnight at 100 DEG C to get EDTA-CoNi metal complex presoma.By the presoma in an inert atmosphere in
475 DEG C of roasting 3h to get arrive NiCo/NC (wherein Ni:31wt%, nNi:nCo=3:1) catalyst.
Embodiment 4-10
By 0.01,0.02 or 0.03g NiCo/NC (wherein Ni:24.1wt%, nNi:nCo=1:1) catalyst, 0.048g furfural
It is added in 50mL teat glass with 2mL isopropanol, is replaced the air in above-mentioned teat glass using high pure nitrogen, heat
To 160,170 or 180 DEG C, 4,6 or 8h is kept to be rapidly cooled to room temperature after reaction, reaction solution is then subjected to centrifugation point
From, take supernatant fluid carry out gas chromatographic detection.Specific catalyst amount, experimental temperature, reaction pressure, reaction time and inspection
Survey the results are shown in Table 1 serial number 4-10.
Embodiment 11
By 0.02g NiCo/NC (wherein Ni:12.9wt%, nNi:nCo=1:3) catalyst, 0.048g furfural and 2mL isopropyl
Alcohol is added in 50mL teat glass, is replaced the air in above-mentioned teat glass using high pure nitrogen, heats 180 DEG C, protects
6h is held, after reaction, is rapidly cooled to room temperature, then reaction solution is centrifuged, supernatant fluid is taken to carry out gas phase color
Spectrum detection.Testing result shows that the yield of furfuryl alcohol is 90%.
Embodiment 12
By 0.02g NiCo/NC (wherein Ni:31wt%, nNi:nCo=3:1) catalyst, 0.048g furfural and 2mL isopropanol
It is added in 50mL teat glass, is replaced the air in above-mentioned teat glass using high pure nitrogen, heat 180 DEG C, keep
6h is rapidly cooled to room temperature after reaction, and then reaction solution is centrifuged, and supernatant fluid is taken to carry out gas-chromatography
Detection.Testing result shows that the yield of furfuryl alcohol is 85%.
Embodiment 13
By 0.02g NiCo/NC (wherein Ni:39wt%, nNi:nCo=4:1) catalyst, 0.048g furfural and 2mL isopropanol
It is added in 50mL teat glass, is replaced the air in above-mentioned teat glass using high pure nitrogen, heat 180 DEG C, keep
6h is rapidly cooled to room temperature after reaction, and then reaction solution is centrifuged, and supernatant fluid is taken to carry out gas-chromatography
Detection.Testing result shows that the yield of furfuryl alcohol is 81%.
Embodiment 14
By 0.02g NiCo/NC (wherein Ni:24.1wt%, nNi:nCo=1:1) catalyst, 0.048g furfural and 2mL methanol
It is added in 50mL teat glass, is replaced the air in above-mentioned teat glass using high pure nitrogen, heat 180 DEG C, keep
6h is rapidly cooled to room temperature after reaction, and then reaction solution is centrifuged, and supernatant fluid is taken to carry out gas-chromatography
Detection.Testing result shows that the yield of furfuryl alcohol is 90%.
Embodiment 15
By 0.02g NiCo/NC (wherein Ni:24.1wt%, nNi:nCo=1:1) catalyst, 0.048g furfural and 2mL isobutyl
Alcohol is added in 50mL teat glass, is replaced the air in above-mentioned teat glass using high pure nitrogen, heats 180 DEG C, protects
6h is held, after reaction, is rapidly cooled to room temperature, then reaction solution is centrifuged, supernatant fluid is taken to carry out gas phase color
Spectrum detection.Testing result shows that the yield of furfuryl alcohol is 94%.
Embodiment 16
By 0.02g NiCo/NC (wherein Ni:24.1wt%, nNi:nCo=1:1) catalyst, 0.048g furfural and 2mL isopropyl
Alcohol is added in 50mL teat glass, is replaced the air in above-mentioned teat glass using high pure nitrogen, heats 180 DEG C, protects
6h is held, after reaction, is rapidly cooled to room temperature, then reaction solution is centrifuged, supernatant fluid is taken to carry out gas phase color
Spectrum detection.Testing result shows that the yield of furfuryl alcohol is 93%.Catalyst after above-mentioned reaction is used isopropanol centrifuge washing 5 times,
Then 40 DEG C of dry 10h in vacuum oven are placed it in.Catalyst after drying is directly used in the second secondary response, according to
The reaction step of first time carries out the cyclical stability test of catalyst, after 6 loop tests, gas chromatographic detection result table
Bright, the yield of furfuryl alcohol is still up to 89%.
Claims (10)
1. a kind of nitrogen-doped carbon nickel-loaded cobalt dual-metal nanocatalyst, which is characterized in that pass through method comprising the following steps
It obtains:
It cobalt source, nickel source, the dispersion of sodium ethylene diamine tetracetate will be dispersed with is placed at 180 ~ 250 DEG C of insulating box and carry out hydro-thermal reaction
Or solvent thermal reaction, EDTA-CoNi metal complex presoma is obtained, by the presoma in a vacuum or inert atmosphere 350 ~ 650
DEG C roasting 1-6h to get arrive a kind of nitrogen-doped carbon nickel-loaded cobalt dual-metal nanocatalyst.
2. a kind of nitrogen-doped carbon nickel-loaded cobalt dual-metal nanocatalyst according to claim 1, which is characterized in that cobalt source
For cobalt nitrate；Nickel source is nickel nitrate；The solvent of dispersion is Methanol+Water.
3. a kind of preparation method of nitrogen-doped carbon nickel-loaded cobalt dual-metal nanocatalyst, which comprises the following steps:
It cobalt source, nickel source, the dispersion of sodium ethylene diamine tetracetate will be dispersed with is placed at 180 ~ 250 DEG C of insulating box and carry out hydro-thermal reaction
Or solvent thermal reaction, EDTA-CoNi metal complex presoma is obtained, by the presoma in a vacuum or inert atmosphere 350 ~ 650
DEG C roasting 1-6h to get arrive a kind of nitrogen-doped carbon nickel-loaded cobalt dual-metal nanocatalyst.
4. a kind of nitrogen-doped carbon nickel-loaded cobalt dual-metal nanocatalyst of any of claims 1 or 2 is for being catalyzed transfer hydrogenation
Application.
5. a kind of nitrogen-doped carbon nickel-loaded cobalt dual-metal nanocatalyst according to claim 4 is for being catalyzed transfer hydrogenation
Application, which is characterized in that catalysis transfer hydrogenation refer to that furfural catalytic hydrogenation in the presence of Organic Alcohol prepares the reaction of furfuryl alcohol.
6. nitrogen-doped carbon nickel-loaded cobalt dual-metal nanocatalyst according to claim 4 is for being catalyzed answering for transfer hydrogenation
With, which is characterized in that expression formula XY/NC, wherein NC is nitrogen-doped carbon carrier, and X is nickel, and Y is cobalt；The content of X is catalyst
The molar ratio n of two kinds of components of 5-60wt%, X and Y of total amountX:nYFor 1:(0.1-5).
7. a kind of method for preparing furfuryl alcohol by furfural catalysis transfer hydrogenation, which comprises the steps of:
In the presence of Organic Alcohol, catalysis transfer is carried out with nitrogen-doped carbon nickel-loaded cobalt dual-metal nanocatalyst catalysis furfural and is added
Hydrogen reaction, obtains furfuryl alcohol.
8. a kind of method for preparing furfuryl alcohol by furfural catalysis transfer hydrogenation according to claim 7, which is characterized in that nitrogen is mixed
Miscellaneous carbon load nickel cobalt dual-metal nanocatalyst be as hydrothermal synthesis method preparation obtained by, preparation step include: by cobalt nitrate,
Nickel nitrate and sodium ethylene diamine tetracetate are dissolved in the in the mixed solvent of first alcohol and water, and liquid after mixing is placed in insulating box
Hydro-thermal reaction 10-48h is carried out at 180 ~ 250 DEG C；After reaction, washed, be dried to obtain EDTA-CoNi metal complex before
Drive body；By the presoma in an inert atmosphere in 350 ~ 650 DEG C of roasting 1-6h to get arrive the catalyst.
9. a kind of method for preparing furfuryl alcohol by furfural catalysis transfer hydrogenation according to claim 7, which is characterized in that described
Organic Alcohol be methanol, ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol, isobutanol or the tert-butyl alcohol, the Organic Alcohol is as reaction dissolvent
And hydrogen donor；The mass ratio of the furfural and catalyst is 2-25:1；The inert reaction atmosphere is nitrogen.
10. a kind of method for preparing furfuryl alcohol by furfural catalysis transfer hydrogenation according to claim 7, which is characterized in that tool
Body step includes: in the presence of nitrogen-doped carbon nickel-loaded cobalt dual-metal nanocatalyst and Organic Alcohol, and control reaction temperature is
100-250 DEG C, furfurol reaction object obtains furfuryl alcohol by being catalyzed transfer hydrogenation 1-24h in inert atmosphere.
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Cited By (6)
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| 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 |
| CN111085232A (en) * | 2019-12-16 | 2020-05-01 | 西南林业大学 | Method for preparing furfuryl alcohol by catalyzing furfural through nitrogen-doped porous carbon-coated non-noble metal catalyst |
| CN111732977A (en) * | 2020-05-22 | 2020-10-02 | 浙江大学 | Method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein |
| CN113247900A (en) * | 2021-05-20 | 2021-08-13 | 济南大学 | Method for preparing NiFe-P-C material |
| CN116060013A (en) * | 2023-02-20 | 2023-05-05 | 中国科学院兰州化学物理研究所 | Method for preparing carbon-coated bimetallic hydrogenation catalyst through hydrothermal carbonization |
| EP4066938A4 (en) * | 2019-11-26 | 2024-01-24 | Consejo Superior Investigacion | Catalyst for the hydrogenation of co2 to methane at low temperatures |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111085232B (en) * | 2019-12-16 | 2022-08-02 | 西南林业大学 | Method for preparing furfuryl alcohol by catalyzing furfural through nitrogen-doped porous carbon-coated non-noble metal catalyst |
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| CN111732977A (en) * | 2020-05-22 | 2020-10-02 | 浙江大学 | Method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein |
| CN113247900A (en) * | 2021-05-20 | 2021-08-13 | 济南大学 | Method for preparing NiFe-P-C material |
| CN116060013A (en) * | 2023-02-20 | 2023-05-05 | 中国科学院兰州化学物理研究所 | Method for preparing carbon-coated bimetallic hydrogenation catalyst through hydrothermal carbonization |
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Application publication date: 20191022 |