CN104607202A - Magnetic nanomaterial supported ruthenium catalyst and application of magnetic nanomaterial supported ruthenium catalyst in preparation of 2, 5-dimethylfuran by catalyzing 5-hydroxymethylfurfural - Google Patents

Magnetic nanomaterial supported ruthenium catalyst and application of magnetic nanomaterial supported ruthenium catalyst in preparation of 2, 5-dimethylfuran by catalyzing 5-hydroxymethylfurfural Download PDF

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Publication number
CN104607202A
CN104607202A CN201510023301.0A CN201510023301A CN104607202A CN 104607202 A CN104607202 A CN 104607202A CN 201510023301 A CN201510023301 A CN 201510023301A CN 104607202 A CN104607202 A CN 104607202A
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catalyst
application
hydrogenolysis
supported ruthenium
ruthenium
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张泽会
刘冰
王树国
吕康乐
任永申
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South Central Minzu University
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South Central University for Nationalities
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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 relates to the technical field of preparation and application of a novel catalyst material, in particular to a magnetic nanomaterial supported ruthenium catalyst and an application of the magnetic nanomaterial supported ruthenium catalyst in preparation of 2, 5-dimethylfuran by catalyzing 5-hydroxymethylfurfural. The magnetic nanomaterial supported ruthenium salt Fe3O4@C-Ru is taken as a catalyst, and a magnetic nanomaterial can be easier to recycle under the external magnetic field, so that the problem of production cost increase caused by the fact that the catalyst is difficult to recycle in the process of 2, 5-dimethylfuran preparation through hydrogenation reduction of 5-hydroxymethylfurfural; the catalyst has the numerous advantages that the catalytic reaction yield is high, products are easy to separate, the catalyst is simple and convenient to recycle and the like, and has a wide application prospect.

Description

Magnetic Nano material supported ruthenium catalyst and prepare the application in 2,5-dimethyl furan at catalysis 5 hydroxymethyl furfural
Technical field
The present invention relates to the preparations and applicatio technical field of new catalysts materials, be specifically related to a kind of magnetic Nano material supported ruthenium catalyst and prepare the application in 2,5-dimethyl furan at catalysis 5 hydroxymethyl furfural.
Background technology
Along with the day by day exhausted of fossil resource and the continuous of Global Emissions of Greenhouse Gas amount are risen, received by the fuel of reproducible biomass resource production high added value and pay close attention to widely, become the hot fields of contemporary scientific research.
2,5-dimethyl furan (DMF) is the very promising regeneratable liquors biomass fuel of one, the features such as compared with ethanol, have energy density high, boiling point is high, and explosion-proof performance is good.
Current DMF is mainly prepared by catalytic hydrogenation 5 hydroxymethyl furfural (HMF).First such as Roman-Leshkov etc. use hydrochloric acid catalysis fructose to generate HMF in diphasic system, then use Cu:Ru/C catalyst to transform 5-HMF and generate DMF, wherein DMF productive rate is 79% (Nature [J], 2007,447:982 ~ 986).Rauchfuss etc. are using formic acid as acid and hydrogen source, and as catalyst, fructose one kettle way is catalytically converted into DMF using palladium carbon (Pd/C), productive rate is 51% (Angew.Chem.Int.Ed [J] .2010,49,6616 ~ 6618.).
The discoveries such as nearest Hu, L, using Ru/C as catalyst, using molecular hydrogen as hydrogen source, after 200 DEG C of reaction 2h, the maximum output of catalysis HMF conversion generation DMF can reach 94.7%, and the conversion ratio of HMF can reach 100%.And this catalyst can be recycled three times and catalytic activity declines (Ind.Eng.Chem.Res [J] .2014,53,3056-3064) hardly.
But in the preparation DMF method disclosed in prior art, major part all employ noble metal catalyst, and catalyst recovery is inconvenient, is unfavorable for large-scale production.
Summary of the invention
For the deficiencies in the prior art, the object of this invention is to provide a kind of magnetic Nano material load ruthenium (Fe 3o 4@C-Ru) catalyst and prepare the application in 2,5-dimethyl furan at catalysis 5 hydroxymethyl furfural, wherein, the carrier magnetic Nano material of catalyst is carbon parcel Fe 3o 4core-shell type magnetic nano material, referred to as Fe 3o 4@C, Fe 3o 4@C can conventionally be prepared.
First, the invention provides a kind of magnetic Nano material Fe 3o 4@C load ruthenium (Fe 3o 4@C-Ru) catalyst, in described catalyst, active component ruthenium is nano metal particles, and in described catalyst, ruthenium element mass fraction is 1% ~ 10%;
Preferably, the step of the synthetic method of described catalyst is as follows:
(1), by FeCl 36H 2o, polyvinylpyrrolidone and sodium acetate join in ethylene glycol, obtain Fe by solvent thermal reaction 3o 4nano material.
(2), by the Fe obtained by step (1) 3o 4nano material and glucose carry out solvolytic reaction and obtain Fe 3o 4@C.
(3), by the Fe obtained by step (2) 3o 4@C ultrasonic (ultrasonic time is 0.5h) is distributed in ethylene glycol, adds hydrate ruthenium trichloride RuCl 3xH 2o heats after after a period of time and obtains Fe 3o 4@C-Ru catalyst.
Preferred, in step (3), heating-up temperature is 25 ~ 150 DEG C;
Preferred, in step (3), the heat time is 2-12h;
By the Fe prepared by the present invention 3o 4@C-Ru catalyst is used for catalysis 5 hydroxymethyl furfural and prepares 2,5-dimethyl furan, and its step is as follows: at Fe 3o 4under the effect of@C-Ru catalyst, 5 hydroxymethyl furfural is carried out in a solvent hydrogenolysis and obtain 2,5-dimethyl furan.
Preferably, the temperature of described hydrogenolysis is: 25 ~ 150 DEG C;
Preferably, the pressure of described hydrogenolysis is 1bar ~ 30bar;
Preferably, described Fe 3o 4the mass ratio of@C-Ru catalyst and 5 hydroxymethyl furfural is 1.2-1.3:1.
Compared with prior art, the advantage of catalyst of the present invention and application thereof and beneficial effect are:
1, relative to other precious metal palladium, platinum etc., the active component of used catalyst of the present invention is the metal Ru of relative low price;
2, the active component ruthenium load of catalyst of the present invention is at magnetic carbon material surface, and this carbon material surface contains abundant electron rich group as hydroxyl, carboxyl etc., and can be used for stable ruthenium nano metal particles, therefore catalyst stability of the present invention is high, not easy in inactivation;
3, catalyst activity of the present invention is high, (under normal temperature, normal pressure) can realize catalytic hydrogenation living beings platform chemicals 5 hydroxymethyl furfural synthesising biological fuel 2,5-dimethyl furan under relatively mild condition;
4, catalyst recovery of the present invention and reuse simple to operate, only need under the effect of externally-applied magnetic field, can separate from reaction system rapidly, the complex separations method not needing routines such as filtering, centrifugal and the catalyst reclaimed can be recycled, simple to operate.
Accompanying drawing explanation
Fig. 1 is the Fe of embodiment 1 step 2 gained 3o 4the transmission electron microscope figure of@C magnetic Nano material.
Fig. 1 illustrates carrier Fe 3o 4@C is typical nucleocapsid structure, and that intermediate colors is dark is Fe 3o 4core, and exterior color more shallow be carbon-coating, this layer thickness is approximately 30nm, and this figure shows prepared hud typed Fe 3o 4@C nano material is successful.
Fig. 2 is the Fe of embodiment 1 step 3 gained 3o 4the transmission electron microscope figure of@C-Ru catalyst.
Fig. 2 illustrates at Fe 3o 4the outer surface of@C magnetic Nano material, has successfully prepared ruthenium nano-particle, and the particle diameter of this nano particle is about 10nm.This figure shows Fe 3o 4@C magnetic Nano material surface Absorbable organic halogens ground load ruthenium nano metal particles.
Fig. 3 is the Fe of embodiment 1 step 3 gained 3o 4@C-Ru catalyst hysteresis graph.
As seen from the figure, the saturation magnetic field intensity of this catalyst under the room temperature of-30000 to+30000Oe magnetic field ranges reaches 43emug -1, this figure shows that catalyst of the present invention has stronger magnetic, under externally-applied magnetic field, can be separated rapidly.
Fig. 4 is hydrogenation reaction device of the present invention.
As seen from the figure, Fe of the present invention 3o 4it is simple that@C-Ru catalyst to catalyzing hydrogenating and reducing 5 hydroxymethyl furfural prepares 2,5-dimethyl furan device, is easy to operation.
Fig. 5 is after catalytic reaction completes, catalyst separating effect schematic diagram under externally-applied magnetic field in reaction system.
As seen from the figure, Fe 3o 4@C-Ru catalyst is under additional magnet effect, can separate from reaction system rapidly, this figure shows that catalyst of the present invention has stronger magnetic, can under externally-applied magnetic field, separate from reaction system fast, therefore the recycling of catalyst of the present invention is simple and easy to do.
Detailed description of the invention
Below list some specific embodiments to be further described the present invention, but be not used for limiting the scope of the invention.
Embodiment 1
A kind of magnetic Nano material load ruthenium (Fe 3o 4@C-Ru) preparation method of catalyst, its step is as follows:
1, Fe 3o 4the preparation of nano material: according to the people such as Diao Guowang (J Phys Chem C 2011; 115:18923-34.) synthesis of the method that designs.By 1.5g FeCl 36H 2o, 1g polyvinylpyrrolidone (mean molecule quantity is 1300000) and 2g sodium acetate join in 30mL ethylene glycol, vigorous stirring 2h, then gained mixture is transferred in polytetrafluoroethyllining lining stainless steel autoclave, 8h is reacted at 200 DEG C, gained black precipitate is collected with magnet, and 60 DEG C of vacuum drying 24h after washing 2 times with ethanol, obtain black solid, be Fe 3o 4nano material.
2, Fe 3o 4the preparation of@C magnetic Nano material: according to (Langmuir2010 such as Li Shenghai; Method synthesis 26:6676-80.) designed.By the Fe obtained by step 1 3o 4nano material is immersed in 0.1M HNO 3in 5 minutes, isolate Fe with magnet afterwards 3o 4and wash 3 times by deionized water.Afterwards by Fe 3o 4nano material (0.002mol), glucose (0.005mol) and urea (0.05mol) join in 40mL water, vigorous stirring is transferred to 50mL polytetrafluoroethyllining lining stainless steel autoclave after 10 minutes, at 200 DEG C, react 15h.Products therefrom is separated with magnet after cooling to room temperature, and successively washs in 40 DEG C of vacuum drying 12h after solid product with deionized water and ethanol, and products obtained therefrom is Fe 3o 4@C magnetic Nano material.
3, Fe 3o 4the preparation of@C-Ru catalyst: by the Fe obtained by step 2 3o 4@C magnetic Nano material (80mg) joins in 50mL ethylene glycol, ultrasonic 30 minutes, then drips containing 20mgRuCl in gained solution 3xH 2(wherein Ru element quality accounts for RuCl to O 3xH 240% of O gross mass) 5mL ethylene glycol solution.By gained mixture with vigorous stirring in 105 DEG C of reaction 5h, collect products obtained therefrom with magnet after being chilled to room temperature, and in 50 DEG C of dried in vacuo overnight after washing three times by deionized water, obtain Fe 3o 4@C-Ru magnetic nano-catalyst, wherein the mass percentage content of metal Ru is 8%.
Embodiment 2
Utilize Fe prepared by embodiment 1 3o 4@C-Ru catalyst hydro-reduction 5 hydroxymethyl furfural prepares 2,5-dimethyl furan:
By Fe prepared by HMF (50.4mg), oxolane (THF, 12mL) and embodiment 1 3o 4@C-Ru catalyst (65mg) joins in 50mL stainless steel cauldron, after hydrogen exchange air three times, by gained mixture under 1 ~ 30bar Hydrogen Vapor Pressure, is heated to 130 DEG C of stirring reactions 6 hours.Detect through high performance liquid chromatography, HMF conversion ratio and gained DMF productive rate are as following table.
Hydrogen Vapor Pressure HMF conversion ratio (%) DMF productive rate (%)
1bar 10.2 8.6
10bar 45.2 36.6
15bar 87.6 77.7
30bar 98.9 87.3
The Fe of the different ruthenium mass fraction of embodiment 3 3o 4the preparation of@C-Ru catalyst and catalytic activity thereof
The Fe of different ruthenium mass fraction 3o 4the preparation method of@C-Ru catalyst, with embodiment 1, only changes RuCl in step 3 3xH 2the addition (2.5-25mg) of O, can obtain activity component metal ruthenium mass percent 1% ~ 10% Fe 3o 4@C-Ru catalyst.
Be the Fe of 1% ~ 10% by HMF (50.4mg), THF (12mL) and above-mentioned ruthenium mass fraction 3o 4@C-Ru catalyst (65mg) joins in 50mL stainless steel cauldron, after hydrogen exchange air three times, by gained mixture under 15bar Hydrogen Vapor Pressure, is heated to 130 DEG C of stirring reactions 6 hours.Detect through high performance liquid chromatography, HMF conversion ratio and gained DMF productive rate are as following table:
The mass fraction of Ru in catalyst HMF conversion ratio (%) DMF productive rate (%)
1％ 12.4 9.2
4％ 41.8 35.5
8％ 87.6 77.7
10％ 97.6 86.9
Fe under embodiment 4 different temperatures 3o 4the catalytic activity of@C-Ru catalyst
Ruthenium mass fraction HMF (50.4mg), THF (12mL) and embodiment 1 prepared is the Fe of 8% 3o 4@C-Ru catalyst (65mg) joins in 50mL stainless steel cauldron, after hydrogen exchange air three times, by gained mixture under 15bar Hydrogen Vapor Pressure, and stirring reaction 6 hours under different temperatures.Detect through high performance liquid chromatography, HMF conversion ratio and gained DMF productive rate are as following table:
Reaction temperature (DEG C) HMF conversion ratio (%) DMF productive rate (%)
25 2.6 2.2
50 34.3 29.5
100 67.6 60.3
130 87.6 77.7
150 100 34.2
The recovery of embodiment 5 catalyst
Recycled by the catalyst of recovery, the method recycled is as follows:
Ruthenium mass fraction HMF (50.4mg), THF (12mL) and embodiment 1 prepared is the Fe of 8% 3o 4@C-Ru catalyst (65mg) joins in 50mL stainless steel cauldron, after hydrogen exchange air three times, by gained mixture under 15bar Hydrogen Vapor Pressure, and stirring reaction 6 hours at 130 DEG C.After completion of the reaction, mixture in reactor is imported in reaction bulb, with magnet by catalyst separation, pour out reaction liquid, then catalyst is washed 3-4 time respectively with deionized water and ethanol successively, and by gained catalyst in 50 DEG C of vacuum drying 24h, namely can be used for carrying out recycling next time, so repeatedly several times.Catalyst to recycle result as shown in the table:
Recycle number of times HMF conversion ratio (%) DMF productive rate (%)
1 87.6 77.7
2 87.5 76.7
3 86.4 77.0
4 85.9 75.5
5 86.3 76.2

Claims (8)

1. a magnetic Nano material Fe 3o 4@C supported ruthenium catalyst, in described catalyst, active component ruthenium is nano metal particles, and in described catalyst, ruthenium element content is 1% ~ 10%.
2. catalyst according to claim 1, is characterized in that, the preparation method of described catalyst is as follows: by 80 mg Fe 3o 4@C magnetic Nano material joins in 50 mL ethylene glycol, ultrasonic 30 minutes, then in gained solution, drip the 5 mL ruthenium trichloride ethylene glycol solutions containing Ru 1-10mg, by gained mixture with vigorous stirring in 105 DEG C of reaction 5 h, products obtained therefrom is collected with magnet after being chilled to room temperature, and in 50 DEG C of dried in vacuo overnight after washing three times by deionized water.
3. the application of the catalyst described in claim 1 or 2 in catalytic hydrogenation.
4. the catalyst described in claim 1 or 2 prepares the application in 2,5-dimethyl furan at catalysis 5 hydroxymethyl furfural.
5. application according to claim 4, is characterized in that, operates as follows: under the effect of described catalyst, 5 hydroxymethyl furfural is carried out in a solvent hydrogenolysis and obtains 2,5-dimethyl furan;
The temperature of described hydrogenolysis is: 25 ~ 150 DEG C;
The pressure of described hydrogenolysis is 1 ~ 30 bar;
Described Fe 3o 4the mass ratio of@C-Ru catalyst and 5 hydroxymethyl furfural is 1.2-1.3:1.
6. application according to claim 5, is characterized in that: the pressure of described hydrogenolysis is 15 ~ 30 bar.
7. application according to claim 5, is characterized in that: the temperature of described hydrogenolysis is 100 ~ 150 DEG C.
8. application according to claim 7, is characterized in that: the temperature of described hydrogenolysis is 130 DEG C.
CN201510023301.0A 2015-01-16 2015-01-16 Magnetic nanomaterial supported ruthenium catalyst and application of magnetic nanomaterial supported ruthenium catalyst in preparation of 2, 5-dimethylfuran by catalyzing 5-hydroxymethylfurfural Pending CN104607202A (en)

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CN109876823A (en) * 2019-03-12 2019-06-14 华东理工大学 A kind of Mn-Fe composite metal catalyst and its preparation method and application
CN110252402A (en) * 2019-07-18 2019-09-20 青岛科技大学 A kind of metal ruthenium nano particle hydrogenation catalyst that magnetism alkali lignin is amine stabilized
EP3427822A4 (en) * 2016-03-07 2020-01-01 Korea Institute of Industrial Technology Catalyst for preparing 2,5-furancarboxylic acid and method for preparing 2,5-furancarboxylic acid using catalyst
CN113121481A (en) * 2019-12-31 2021-07-16 中国石油化工股份有限公司 Ruthenium-based catalyst and method for preparing 2, 5-furandicarboxylic acid by using same
CN114105914A (en) * 2021-11-04 2022-03-01 厦门大学 Method for preparing 2, 5-furandimethanol by using 5-chloromethyl furfural

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Cited By (9)

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Publication number Priority date Publication date Assignee Title
EP3427822A4 (en) * 2016-03-07 2020-01-01 Korea Institute of Industrial Technology Catalyst for preparing 2,5-furancarboxylic acid and method for preparing 2,5-furancarboxylic acid using catalyst
US10661252B2 (en) 2016-03-07 2020-05-26 Korea Institute Of Industrial Technology Catalyst for preparing 2,5-furancarboxylic acid and a method for preparing 2,5-furancarboxylic acid using the catalyst
CN109876823A (en) * 2019-03-12 2019-06-14 华东理工大学 A kind of Mn-Fe composite metal catalyst and its preparation method and application
CN109876823B (en) * 2019-03-12 2022-01-18 华东理工大学 Mn-Fe composite metal catalyst and preparation method and application thereof
CN110252402A (en) * 2019-07-18 2019-09-20 青岛科技大学 A kind of metal ruthenium nano particle hydrogenation catalyst that magnetism alkali lignin is amine stabilized
CN110252402B (en) * 2019-07-18 2022-03-18 青岛科技大学 Magnetic alkali lignin amine stable metal ruthenium nanoparticle hydrogenation catalyst
CN113121481A (en) * 2019-12-31 2021-07-16 中国石油化工股份有限公司 Ruthenium-based catalyst and method for preparing 2, 5-furandicarboxylic acid by using same
CN114105914A (en) * 2021-11-04 2022-03-01 厦门大学 Method for preparing 2, 5-furandimethanol by using 5-chloromethyl furfural
WO2023077822A1 (en) * 2021-11-04 2023-05-11 厦门大学 Method for preparing 2,5-bishydroxymethylfuran by using 5-chloromethylfurfural

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Application publication date: 20150513