CN109603837A - A kind of preparation method of the Cu/Ce/Co catalyst for furfural liquid-phase hydrogenatin - Google Patents
A kind of preparation method of the Cu/Ce/Co catalyst for furfural liquid-phase hydrogenatin Download PDFInfo
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- CN109603837A CN109603837A CN201910046519.6A CN201910046519A CN109603837A CN 109603837 A CN109603837 A CN 109603837A CN 201910046519 A CN201910046519 A CN 201910046519A CN 109603837 A CN109603837 A CN 109603837A
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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
- B01J23/76—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
- B01J23/83—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 rare earths or actinides
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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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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Abstract
The invention discloses a kind of Cu/Ce/Co catalyst for preparing furancarbinol from liquid-phase furol hydrogenation, catalyst Cu load capacity is low, it is active it is high, stability is good.The Cu/Ce/Co catalyst is by Cu, CeO2And Co3O4Composition, wherein the mass percent of each component is Cu:5~35%, CeO in the Cu/Ce/Co catalyst2: 5~35%, Co3O4: 30~70%.And preparation method thereof and in the purposes for preparing furancarbinol from liquid-phase furol hydrogenation.Cu/Ce/Co catalyst according to the present invention is only made of three kinds of inorganic substances, and green non-poisonous, preparation process is simple, cheap, easy to use, and with excellent activity, selectivity and stability, the selectivity of furfural conversion ratio and furfuryl alcohol is significantly improved.
Description
Technical field
The invention belongs to field of catalyst preparation, relate in particular to it is a kind of for preparing furancarbinol from liquid-phase furol hydrogenation by
Cu、CeO2And Co3O4The preparation method and its usage of the catalyst of composition.
Background technique
The non-renewable fossil resource such as petroleum, coal constitutes the foundation stone of the current energy and chemical industry.But fossil resource
Increasingly depleted and use process in caused by environmental pollution and greenhouse gas emission have become restriction society and economy and can hold
The bottleneck of supervention exhibition.Resource and the dual-pressure of environment have pushed people to convert biomass and its derivatives selectively significantly
Research on utilization.The production of furfural is original with the reproducible farm-forestry crop such as bagasse, corncob, rice husk rich in pentosan
Material, has the characteristics that inexhaustible, nexhaustible.Wherein hydrogenation products furfuryl alcohol is a kind of important Organic Chemicals, mainly
For producing furfural resin, furane resins, furfuryl alcohol-pollopas, phenolic resin etc..It is also used for preparing tartaric acid, plasticizer, solvent
With rocket fuel etc..In addition, also having been widely used in industrial departments such as dyestuff, synthetic fibers, rubber, pesticide and castings.With
The rapid development of applied chemistry and fine chemistry industry, the demand to furfuryl alcohol also constantly increasing.Therefore, furfural method production chaff is sought
The Green Sustainable path of alcohol has far-reaching significance and wide prospect.
Containing having carbon-to-carbon double bond on active aldehyde and furan nucleus in Furfural Molecule, determine that its hydrogenation reaction is mainly aldehyde
Carbon-to-carbon double bond adds hydrogen saturation, generation furfuryl alcohol or tetrahydrofurfuryl alcohol on C=O bond and furan nucleus in base.Further, since by phase
The influence of adjacent furan nucleus, the carbon-oxygen bond on furfuryl alcohol side chain are easy to disconnect, and are hydrogenated to 2- methylfuran.Therefore, by constructing not
Same catalyst realizes that the orientation conversion of furfural to furfuryl alcohol on Ni metal base catalyst has great importance.
It is well known that Furfural hydrogenation to furfural alcohol can be divided into liquid phase method and vapor phase method, due to active metal, carrier type, help
The factors such as agent and the interaction of carrier, so that various catalyst show very big difference in furfural hydrogenation reaction.
Furfuraldehyde hydrogenation catalyst mainly has at present:
1) series catalysts of Cu containing chromium: such as Zhu Yu thunder (petrochemical industry, 1992,217,466-469) discloses a kind of total
The Cu-Cr catalyst of precipitation method preparation, the catalyst can make furfural conversion ratio reach 100%, and furfuryl alcohol selectivity and yield are all
98% or more.But contains carcinogen Cr in the catalyst, cause serious pollution of chromium, low chromium or chromium-free catalyst have become
The development trend of furfural production.
2) Chrome-free Cu series catalysts, including CuO-SiO2, Cu-Zn series catalysts, Cu-Al series catalysts etc..Such as Zhou Ya
Bright equal (petrochemical industry, 1997,26 (1): 4-7), which are disclosed, has carried out active testing to Cu-Zn series catalysts,.(the essence such as Li Guoan
Thin petrochemical industry, 1995, (1): 40-) to carrier γ-Al2O3, active carbon, MT grades of white carbon blacks and SiO2It is screened.But these
Catalyst is disadvantageous in that reaction temperature is higher, and copper crystal grain, which is easily grown up, causes sintering of catalyst.
3) skeleton nickel catalyst: Liu Baijun etc. (catalysis journal, 1997,18 (5): 176-178) discovery heteropolyacid salt
Cu3/2PM12O40Modified RNi is disadvantageous in that catalyst easy in inactivation to Furfural hydrogenation to furfural alcohol activity with higher.
4) skeleton Co series catalysts: patent CN1066610 discloses a kind of cobalt for furfural liquid-phase hydrogenatin production furfuryl alcohol
It is skeleton catalyst, but has Cr in the catalyst, causes pollution of chromium.
Therefore a kind of more environmentally friendly and excellent catalytic performance suitable for preparing furancarbinol from liquid-phase furol hydrogenation there is still a need for developing
Catalyst.
Summary of the invention
Based on problems of the prior art, it is an object of the present invention to provide one kind to be used for furfural liquid-phase hydrogenatin
The Cu/Ce/Co catalyst of furfuryl alcohol processed, catalyst Cu load capacity is low, it is active it is high, stability is good.
The catalyst according to the present invention for adding hydrogen for furfural selection, by Cu, CeO2And Co3O4Composition.Wherein, institute
The mass percent for stating each component in Cu/Ce/Co catalyst is Cu:5~35%, CeO2: 5~35%, Co3O4: 30~70%.
Preferably, the mass percent of each component is Cu:15~20%, CeO in the Cu/Ce/Co catalyst2: 10~
25%, Co3O4: 55~75%.
It is another object of the present invention to provide the preparation methods of the Cu/Ce/Co catalyst, include the following steps:
According to the stoichiometric ratio of Cu, Ce and Co, it is 0.5~3mol/L's that the inorganic salts of copper, cerium and cobalt, which are made into concentration,
Mixed-salt aqueous solution；Coprecipitation reaction is carried out with the aqueous slkali of 0.1~2mol/L, after completion of the reaction, mineral salt presoma is through 60
It after DEG C 2~5h of water-bath aging, suction filtration, washing to neutrality, is successively dried, roasting and reduction reaction, obtains the Cu/Ce/
Co catalyst.
The preparation method of copper-based catalysts of the present invention, it is characterised in that: the copper, cerium, cobalt inorganic salts can be nitre
Hydrochlorate and/or hydrochloride.
The preparation method of Cu/Ce/Co catalyst of the present invention, it is characterised in that: the copper, cerium, the inorganic salts of cobalt are dense
Degree is preferably 0.5~1mol/L.
The preparation method of Cu/Ce/Co catalyst of the present invention, it is characterised in that: in the aqueous slkali, alkali is selected from hydrogen-oxygen
Change at least one of sodium and sodium carbonate.
The preparation method of Cu/Ce/Co catalyst of the present invention, it is characterised in that: the alkaline concentration be 0.5~
2.0mol/L。
The preparation method of Cu/Ce/Co catalyst of the present invention, it is characterised in that: in the coprecipitation reaction step, instead
The pH value answered is 9~11, preferably 10~11；Reaction temperature is 50~80 DEG C.
The preparation method of copper-based catalysts of the present invention, it is characterised in that: described in the coprecipitation reaction step
Ageing time is 3~12h；The drying condition are as follows: 30~150 DEG C of temperature, the time is 4~12h；The roasting condition are as follows:
Temperature is 300~550 DEG C, and the time is 2~10h.In the reduction step, reducing atmosphere is high-purity hydrogen, hydrogen (High Purity Hydrogen
Gas) 50~200mL/min of flow, 300~550 DEG C of reduction temperature are risen to by room temperature with the heating rate of 5 DEG C/min, reductase 12~
5h。
It is another object of the present invention to provide the Cu/Ce/Co catalyst by preparing furfuryl alcohol by furfural liquid phase hydrogenation
In application.
It is yet a further object of the present invention to provide a kind of method by preparing furfuryl alcohol by furfural liquid phase hydrogenation, the method packets
It includes:
Enclosed high pressure reaction kettle is added in reaction raw materials furfural, water and Cu/Ce/Co catalyst according to the present invention
In, the initial pressure for filling hydrogen in reaction kettle at room temperature is 1~8MPa, and reaction temperature is 60~180 DEG C, and the reaction time is
10min~10h.The mass ratio of the raw material furfural and water is 1:50~1:10, the matter of the raw material furfural and the catalyst
Amount is than being 1:1~20:1.
Preferably, in the method by preparing furfuryl alcohol by furfural liquid phase hydrogenation, reaction temperature is 90~140 DEG C, at room temperature
Initial hydrogen pressure is 3~6MPa in reaction kettle, and the reaction time is 30min~5h.
Beneficial effect
Cu/Ce/Co catalyst according to the present invention is only made of three kinds of inorganic substances, green non-poisonous, preparation process
Simply, cheap, it is easy to use, there is excellent activity, selectivity and stability, the selectivity of furfural conversion ratio and furfuryl alcohol
It is significantly improved.
Detailed description of the invention
Fig. 1 is X-ray diffraction (XRD) map of Cu/Ce/Co catalyst before restoring in embodiment 1.
Fig. 2 is the XRD spectrum of Cu/Ce/Co catalyst after restoring in embodiment 1.
Specific embodiment
Hereinafter, will be described in detail the present invention.Before doing so, it should be appreciated that in this specification and appended
Claims used in term should not be construed as being limited to general sense and dictionary meanings, and inventor should allowed
On the basis of the appropriate principle for defining term to carry out best interpretations, according to meaning corresponding with technical aspect of the invention and generally
Thought explains.Therefore, description presented herein is not intended to limitation originally merely for the sake of the preferred embodiment for illustrating purpose
The range of invention, it will thus be appreciated that without departing from the spirit and scope of the present invention, it can be obtained by it
His equivalents or improved procedure.
Cu/Ce/Co catalyst according to the present invention is low in cost using cheap metal copper as main active component, together
When exhibit improvements over the furfural selective hydrogenation behavior of Cu/Ce and Cu/Co, and the Cu/Ce/Co catalyst has high stabilization
Property.Catalytic process has very high product yield and selectivity, and under the reaction condition compared with optimization, the yield of furfuryl alcohol be can achieve
90% or more.Thus, it has a good application prospect.
Following embodiment is enumerated only as the example of embodiment of the present invention, does not constitute any limit to the present invention
System, it will be appreciated by those skilled in the art that modification in the range of without departing from essence and design of the invention each falls within the present invention
Protection scope.Unless stated otherwise, reagent and instrument used in the following embodiment are commercially available product.
Embodiment 1
It prepares Cu/Ce/Co catalyst: preparing the Cu (NO that total concentration of metal ions is 2mol/L3)2·3H2O、Ce
(NO3)3·6H2O and Co (NO3)2·6H2O mixed solution, wherein molar ratio Cu:Ce:Co=0.5:1:4, in addition, preparing mol
(NaOH):mol(Na2CO3The mixed ammonium/alkali solutions of)=2:1 (total concentration 3mol/L).Under vigorous stirring, by above-mentioned salting liquid
It is added dropwise in three-necked flask and is co-precipitated simultaneously with aqueous slkali, control precipitated liquid pH 9~10,50 DEG C of precipitation temperature.Precipitating
After aging 5h, be filtered, washed, dry, 400 DEG C of roasting 4h；Again by the catalyst precursor in hydrogen atmosphere with 5 DEG C/
The heating rate of min restores 4h to 300 DEG C, and the flow of hydrogen is 100mL/min, is cooled to room temperature to obtain Cu/Ce/Co catalysis
Agent.
Embodiment 2
It prepares Cu/Ce/Co catalyst: preparing the Cu (NO that total concentration of metal ions is 1.5mol/L3)2·3H2O、Ce
(NO3)3·6H2O and Co (NO3)2·6H2The mixed solution of O, wherein molar ratio Cu:Ce:Co=1:2:5, in addition compound concentration
For the NaOH solution of 2.0mol/L.Under vigorous stirring, above-mentioned salting liquid and aqueous slkali are added dropwise in three-necked flask simultaneously into
Row co-precipitation, the pH of control gained precipitation solution is 9~10,60 DEG C of precipitation temperature.Aging 10h after precipitating is filtered, is washed
Wash, dry, 450 DEG C of roasting 5h, then by the catalyst precursor in hydrogen atmosphere with the heating rate of 5 DEG C/min to 350 DEG C,
5h is restored, the flow of hydrogen is 120mL/min, is cooled to room temperature to obtain Cu/Ce/Co catalyst.
Embodiment 3
It prepares Cu/Ce/Co catalyst: preparing the CuCl that total concentration of metal ions is 2.5mol/L2、Ce(NO3)3·6H2O
With Co (NO3)2·6H2The mixed solution of O, wherein molar ratio Cu:Ce:Co=1:0.5:5, in addition, compound concentration is
The Na of 2.0mol/L2CO3Solution.Under vigorous stirring, above-mentioned salting liquid and aqueous slkali are added dropwise in three-necked flask simultaneously and are carried out
Co-precipitation, control gained precipitated liquid pH is 8~9,70 DEG C of precipitation temperature.Aging 6h after precipitating is filtered, washed, dries,
450 DEG C of roasting 3h, then by the catalyst precursor in hydrogen atmosphere with the heating rate of 5 DEG C/min to 450 DEG C, reductase 12 h,
The flow of hydrogen is 110mL/min, is cooled to room temperature to obtain Cu/Ce/Co catalyst.
Embodiment 4
It prepares Cu/Ce/Co catalyst: preparing the CuCl that total concentration of metal ions is 2.0mol/L2、Ce(NH4)2(NO3)6With
Co(NO3)2·6H2The mixed solution of O, wherein molar ratio Cu:Ce:Co=1:1:6, in addition, compound concentration is 1.5mol/L's
NaOH solution.Under vigorous stirring, above-mentioned salting liquid and aqueous slkali are added dropwise in three-necked flask simultaneously and are co-precipitated, controlled
Precipitated liquid pH is 10~11,80 DEG C of precipitation temperature.Aging 8h after precipitating is filtered, washed, dries, 350 DEG C of roasting 5h, then
By the catalyst precursor in hydrogen atmosphere with the heating rate of 5 DEG C/min to 300 DEG C, restore 4h, the flow of hydrogen is
160mL/min is cooled to room temperature to obtain Cu/Ce/Co catalyst.
Embodiment 5
It prepares Cu/Ce/Co catalyst: preparing the CuCl that total concentration of metal ions is 2.0mol/L2、Ce(NH4)2(NO3)6With
CoCl2·6H2The mixed solution of O, wherein molar ratio Cu:Ce:Co=2:1:5, in addition, compound concentration is 2.0mol/L's
NaOH solution.Under vigorous stirring, above-mentioned salting liquid and aqueous slkali are added dropwise in three-necked flask simultaneously and are co-precipitated, controlled
The pH of acquired solution is precipitated 11~12,40 DEG C of precipitation temperature.Aging 6h after precipitating is filtered, washed, dries, 500 DEG C of roastings
Burn 3h, then by the catalyst precursor in hydrogen atmosphere with the heating rate of 5 DEG C/min to 350 DEG C, restore 3h, the stream of hydrogen
Amount is 150mL/min, is cooled to room temperature to obtain Cu/Ce/Co catalyst.
EXPERIMENTAL EXAMPLE 1: catalysis Furfural hydrogenation to furfural alcohol
It is anti-that the catalyst of the activation prepared in the furfural weighed in advance, embodiment 1 to 5 and water are added to 50mL stainless steel
It answers and carries out hydrogenation reaction in kettle, wherein the mass ratio of cupper-based catalyst and furfural is 1:12, and reaction temperature is 100 DEG C, reaction pressure
For 4MPa, reaction time 5h.The pressure, temperature variation of process is recorded and is monitored by the computer connecting with reactor.
After reaction, stop stirring, room temperature to be down to, pressure release takes the supernatant fluid after being centrifuged, and crosses 0.22 μm of filter membrane, and product uses
Gas-chromatography is analyzed, and is as a result listed in the table below in 1.
Table 1
| Catalyst | Furfural conversion ratio/% | Furfuryl alcohol selectivity/% |
| Embodiment 1 | 100 | 91 |
| Embodiment 2 | 97 | 92 |
| Embodiment 3 | 96 | 88 |
| Embodiment 4 | 100 | 96 |
| Embodiment 5 | 95 | 96% |
As it can be seen that there is activity well to catalysis furfural hydrogenation using metal salt as the Cu/Ce/Co catalyst of precursor preparation
With furfuryl alcohol selectivity；Catalyst is prepared using simple coprecipitation, and raw material is cheap and easy to get, and catalyst is at low cost.Therefore, and now
There is technology to compare, the present invention has advantage and industrial applications prospect economically.
Claims (9)
1. a kind of Cu/Ce/Co catalyst for preparing furancarbinol from liquid-phase furol hydrogenation, the Cu/Ce/Co catalyst is by Cu, CeO2With
Co3O4Composition, wherein the mass percent of each component is Cu:5~35%, CeO in the Cu/Ce/Co catalyst2: 5~
35%, Co3O4: 30~70%.
2. the Cu/Ce/Co catalyst according to claim 1 for preparing furancarbinol from liquid-phase furol hydrogenation, which is characterized in that institute
The mass percent for stating each component in Cu/Ce/Co catalyst is Cu:15~20%, CeO2: 10~25%, Co3O4: 55~
75%.
3. the preparation method of the Cu/Ce/Co catalyst according to claim 1 or 2 for preparing furancarbinol from liquid-phase furol hydrogenation,
Include the following steps:
According to the stoichiometric ratio of Cu, Ce and Co, the inorganic salts of copper, cerium and cobalt are made into the mixing that concentration is 0.5~3mol/L
Saline solution；Coprecipitation reaction is carried out with the aqueous slkali of 0.1~2mol/L, after completion of the reaction, mineral salt presoma is through 60 DEG C of water
It bathes 2~5h of aging, suction filtration, after washing to neutrality, is successively dried, roasting and reduction reaction, obtains the Cu/Ce/Co and urge
Agent.
4. preparation method according to claim 3, which is characterized in that the copper, cerium, cobalt inorganic salts can be nitrate
And/or hydrochloride, the copper, cerium, cobalt inorganic salt concentration be preferably 0.5~1mol/L.
5. preparation method according to claim 3, which is characterized in that the alkali in the aqueous slkali is selected from sodium hydroxide and carbon
At least one of sour sodium, the alkaline concentration are 0.5~2.0mol/L.
6. preparation method according to claim 3, which is characterized in that in the coprecipitation reaction step, the pH value of reaction
It is 9~11, preferably 10~11；Reaction temperature is 50~80 DEG C；The ageing time is 3~12h；The drying condition are as follows:
30~150 DEG C of temperature, the time is 4~12h；The roasting condition are as follows: temperature is 300~550 DEG C, and the time is 2~10h.Institute
It states in reduction step, reducing atmosphere is high-purity hydrogen, 50~200mL/min of hydrogen flowing quantity, with the heating rate of 5 DEG C/min by room
Temperature rise is to 300~550 DEG C of reduction temperature, reductase 12~5h.
7. the Cu/Ce/Co catalyst according to claim 1 or 2 for preparing furancarbinol from liquid-phase furol hydrogenation is by furfural liquid
It is added hydrogen and prepares the application in furfuryl alcohol.
8. a kind of method by preparing furfuryl alcohol by furfural liquid phase hydrogenation, which comprises
By reaction raw materials furfural, water and the Cu/Ce/Co according to claim 1 or 2 for being used for preparing furancarbinol from liquid-phase furol hydrogenation
Catalyst is added in enclosed high pressure reaction kettle, and the initial pressure for filling hydrogen in reaction kettle at room temperature is 1~8MPa, reaction temperature
It is 60~180 DEG C, the reaction time is 10min~10h；The mass ratio of the raw material furfural and water is 1:50~1:10, the original
The mass ratio for expecting furfural and the catalyst is 1:1~20:1.
9. the method according to claim 8 by preparing furfuryl alcohol by furfural liquid phase hydrogenation, which is characterized in that reaction temperature 90
~140 DEG C, initial hydrogen pressure is 3~6MPa in reaction kettle at room temperature, and the reaction time is 30min~5h.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112427038A (en) * | 2020-11-09 | 2021-03-02 | 中国五环工程有限公司 | Preparation method of catalyst for preparing neopentyl glycol by hydrogenation of hydroxypivalaldehyde |
| CN112939904A (en) * | 2019-12-10 | 2021-06-11 | 中国科学院大连化学物理研究所 | Method for preparing furfuryl alcohol by catalyzing furfural hydrogenation with Pt-containing alloy catalyst |
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| CN112939904B (en) * | 2019-12-10 | 2023-01-03 | 中国科学院大连化学物理研究所 | Method for preparing furfuryl alcohol by catalyzing furfural hydrogenation with Pt-containing alloy catalyst |
| CN112427038A (en) * | 2020-11-09 | 2021-03-02 | 中国五环工程有限公司 | Preparation method of catalyst for preparing neopentyl glycol by hydrogenation of hydroxypivalaldehyde |
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| CN109603837B (en) | 2021-12-31 |
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