CN106008414A - Method for preparing 2,5-dihydroxymethyl furan through 5-hydroxymethyl furfural catalytic transfer hydrogenation - Google Patents
Method for preparing 2,5-dihydroxymethyl furan through 5-hydroxymethyl furfural catalytic transfer hydrogenation Download PDFInfo
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Abstract
The invention discloses a method for preparing 2,5-dihydroxymethyl furan through 5-hydroxymethyl furfural catalytic transfer hydrogenation. The method uses magnetic zirconium hydroxide as a catalyst, uses low carbon alcohol as a reaction solvent and a hydrogen donor, 5-hydroxymethyl furfural is selectively converted into the 2,5-dihydroxymethyl furan through Meerwein-Ponndorf-Verley (MPV) transfer hydrogenation reaction in a high-pressure reaction kettle, and the highest yield is up to 91.5%. The raw materials for the used catalyst are low in price, the preparation process is simple, and the catalytic performance is good. In addition, the 2,5-dihydroxymethyl furan has strong magnetism and is easy to separate, recycle and reuse. Furthermore, the used low carbon alcohol can serve as the in-situ hydrogen donor, hydrogen usage is omitted, and the safety of the reaction process is further improved. Moreover, the 2,5-dihydroxymethyl furan can also serve as a reaction solvent, introduction of exogenous substances is reduced, the production costs are further reduced, and the method has a high application value and a good industrialized prospect.
Description
Technical field
The invention belongs to biomass energy chemical field, be specifically related to a kind of 5 hydroxymethyl furfural catalysis transfer hydrogenation and prepare
The method of 2,5-dihydroxymethyl furan.
Background technology
In recent years, the selectivity from the big component of the pretreatment of raw material of lignocellulose to three splits again to the orientation of each component
Conversion had become as utilize one of maximally effective approach of biomass resource (Chemical Reviews, 2011,111:
397-417).Wherein, convert, for raw material orientation, the 5 hydroxymethyl furfural obtained with cellulosic component to be arranged as base by USDOE
One of ten large platform compounds in biomass resource, be also considered as contacting the bridge of biomass resource and petroleum base industry and
Key substance (Chemical Engineering Science, 2016,142:318-346).It addition, obtained by HMF hydrogenation
2,5-dihydroxymethyl furan be also a kind of particularly important organic compound (ChemSusChem, 2013,6:1659-
1667), it both can make as softening agent, wetting agent, binding agent, plasticizer, surfactant and medicine intermediate etc.
With, it is also possible to as the monomer (ACS of the polymeric materials such as synthetic resin material, fibrous material, foamed materials and crown ether material
Catalysis, 2015,5:722-733), there is boundless application prospect.
In the research work of early stage, it is 2 by 5 hydroxymethyl furfural hydro-conversion, the side that 5-dihydroxymethyl furan is used
Method great majority are all using hydrogen as hydrogen donor, using gold, ruthenium, platinum and iridium etc. as catalyst (ChemCatChem, 2013,
5: 2822-2826; RSC Advances, 2013, 3: 1033-1036; Dalton Transactions, 2014,
43,10224-10234).It is important to note that hydrogen currently mainly derives from non-renewable fossil resource, hydrogen manufacturing becomes
This is higher, and hydrogen has polymolecularity and inflammability, is difficult to store and transport, furthermore the dissolving that hydrogen is in various solvents
Spending the highest, atom utilization is relatively low, therefore, 5 hydroxymethyl furfural carries out Hydrogenation for 2 with hydrogen for hydrogen donor, 5-dihydroxy first
Base furan is uneconomic and has bigger potential safety hazard.Meanwhile, gold, ruthenium, platinum and iridium etc. belong to noble metal catalyst, valency
Lattice are expensive, and reclaim not good enough with repeat performance, and these deficiencies all greatly limit 2,5-dihydroxymethyl furan
Actual production and subsequent applications.
Summary of the invention
It is an object of the invention to: provide a kind of 5 hydroxymethyl furfural catalysis transfer hydrogenation to prepare 2,5-dihydroxymethyl furan
Method, the method is using cheap and have the zirconium hydroxide of Magneto separate characteristic as catalyst, with environmental protection and have
The low-carbon alcohols of difunctional feature is as hydrogen donor and reaction dissolvent, and then utilizes MPV transfer hydrogenation by 5 hydroxymethyl furfural
It is selectively converted to 2,5-dihydroxymethyl furan.
The technical solution of the present invention is: with magnetic zirconium hydroxide as catalyst, with low-carbon alcohols as reaction dissolvent with hydrogen
Donor, passes through Meerwein-Ponndorf-Verley(MPV in autoclave) transfer hydrogenation is by 5-methylol bran
Aldehyde is selectively converted to 2,5-dihydroxymethyl furan；It includes step in detail below:
(1) synthesis of magnetic zirconium hydroxide catalyst: under nitrogen atmosphere a certain amount of nano ferriferrous oxide is joined use
Deionized deoxygenated water preparation containing in certain density zirconium chloride or zirconyl chloride solution, mechanical agitation 30 ~ 90 min, ultrasonic
Dispersion 10 ~ 60 min；Under mechanical agitation, in above-mentioned solution, dropwise drip ammonia spirit until pH=9 ~ 11, continue to stir
Mix 30 min, still aging 24 h；By Magnet, solid precipitation is separated, and with deionized water cyclic washing precipitation until
Exist without chloride ion；By solid precipitation 105 DEG C vacuum drying 12 h after washing, and ground to 200 mesh, obtained magnetic
Property zirconium hydroxide catalyst；
(2) MPV transfer hydrogenation: a certain amount of magnetic zirconium hydroxide catalyst, 5 hydroxymethyl furfural and low-carbon alcohols are added
In 100 mL Parr autoclaves, with air in nitrogen displacement still after sealing；Nitrogen pressure is adjusted to reaction pressure,
It is warming up to assigned temperature under certain mechanical agitation speed, after the reaction stipulated time, obtains 2,5-dihydroxymethyl furan.
Wherein, the zirconates concentration described in step (1) is 50 ~ 100 g/L, and ferrum is 1:1 ~ 1:6 with the mol ratio of zirconium.
Wherein, the mechanical agitation speed described in step (1) is 200 ~ 600 rpm, and ammonia rate of addition is 3 ~ 6 mL/
min。
Wherein, the low-carbon alcohols described in step (2) is in ethanol, normal propyl alcohol, isopropanol, n-butyl alcohol or sec-butyl alcohol
Kind, its consumption is 20 ~ 50 g.
Wherein, 1 ~ 5 wt% that 5 hydroxymethyl furfural consumption is low-carbon alcohols consumption described in step (2), described magnetic
Zirconium hydroxide consumption is 20 ~ 100 wt% of 5 hydroxymethyl furfural consumption.
Wherein, the nitrogen pressure described in step (2) is 1 ~ 10 bar, and described mixing speed is 200 ~ 600 rpm, institute
The reaction temperature stated is 130 ~ 180 DEG C, and the described response time is 2 ~ 8 h.
The invention have the advantage that the catalyst not only manufacturing process of use is simple, catalytic performance is excellent, and is easily isolated
Reclaim and reuse；The low-carbon alcohols used can not only substitute hydrogen as in-situ hydrogen donor, can increase course of reaction
Safety and high efficiency, but also can be directly as the solvent of transfer hydrogenation, it is to avoid the use of other external source solvents, enter
One step reduces production cost, has stronger economic advantages and industrial prospect.
Accompanying drawing explanation
Fig. 1 is the Zr (OH) of embodiment 1 preparation4@Fe3O4(1:1) x-ray diffraction pattern；
Fig. 2 is the Zr (OH) of embodiment 2 preparation4@Fe3O4(3:1) infrared spectrogram；
Fig. 3 is the Zr (OH) of embodiment 4 preparation4@Fe3O4(2:1) Magneto separate design sketch.
Detailed description of the invention
Below in conjunction with embodiment, technical scheme is described further, the following stated, is only the present invention
Preferred embodiment, not does the restriction of other form to the present invention, any those skilled in the art possibly also with
The technology contents of the disclosure above is changed to the Equivalent embodiments changed on an equal basis.Every without departing from the present invention program content, depend on
Any simple modification done following example according to the technical spirit of the present invention or equivalent variations, all fall within the protection of the present invention
In the range of.
Embodiment 1: be that 1:1 joins and goes with deoxidation by nano ferriferrous oxide by ferrum/zirconium mol ratio under nitrogen atmosphere
In the zirconium chloride solution containing 50 g/L of ionized water preparation, mechanical agitation 30 min, ultrasonic disperse 10 min；In mechanical agitation
Speed is under the conditions of 200 rpm to be that 3 mL/min dropwise drip ammonia spirit until pH=9 by rate of addition in above-mentioned solution,
Continue stirring 30 min, still aging 24 h；By Magnet, solid precipitation is separated, and sink with deionized water cyclic washing
Form sediment until existing without chloride ion；Solid precipitation after washing is vacuum dried 12 h at 105 DEG C, and is ground to 200
Mesh, obtains magnetic zirconium hydroxide catalyst, referred to as Zr (OH)4@Fe3O4(1:1)；It follows that by 20 g ethanol, 0.2 g 5-hydroxyl
Methyl furfural and 0.04 g Zr (OH)4@Fe3O4(1:1) join in 100 mL Parr autoclaves, after sealing, use nitrogen
Air in displacement still；Nitrogen pressure being adjusted to 1 bar, is warming up to 130 DEG C under mechanical agitation speed is 200 rpm, MPV is anti-
2,5-dihydroxymethyl furan is i.e. can get after answering 8 h；Understanding through gas chromatograph detection, the yield of 2,5-dihydroxymethyl furan reaches
To 72.9%.
It addition, Zr (OH)4@Fe3O4(1:1) X-ray diffraction analysis as it is shown in figure 1, wherein, 2 θ are 30.2 °, 35.6 °,
Diffraction maximum at 43.2 °, 53.5 °, 57.2 ° and 62.7 ° is respectively belonging to Fe3O4(220), (311), (400), (422),
(511) and (440) crystal face, it is to match with the magnetic iron ore crystal structure collection of illustrative plates (JCPDS Card No. 19-0629) of standard
, this explanation Fe in the preparation process of magnetic zirconium hydroxide catalyst3O4The structure of component is the most significantly affected；Separately
Outward, X-ray diffracting spectrum does not find obvious Zr (OH)4Diffraction maximum, this explanation Zr (OH)4Have well without fixed
Type structure is also being dispersed in Fe3O4Core surfaces.
Embodiment 2: be that 1:3 joins and goes with deoxidation by nano ferriferrous oxide by ferrum/zirconium mol ratio under nitrogen atmosphere
In the zirconyl chloride solution containing 75 g/L of ionized water preparation, mechanical agitation 60 min, ultrasonic disperse 30 min；Stir at machinery
Mixing speed is under the conditions of 400 rpm to be that 4 mL/min dropwise drip ammonia spirit until pH=by rate of addition in above-mentioned solution
10, continue stirring 30 min, still aging 24 h；By Magnet, solid precipitation is separated, and repeatedly wash with deionized water
Wash precipitation until existing without chloride ion；Will washing after solid precipitation 105 DEG C be vacuum dried 12 h, and ground to
200 mesh, obtain magnetic zirconium hydroxide catalyst, referred to as Zr (OH)4@Fe3O4(3:1)；It follows that by 30 g n-butyl alcohol, 0.9 g
5 hydroxymethyl furfural and 0.54 g Zr (OH)4@Fe3O4(3:1) join in 100 mL Parr autoclaves, use after sealing
Air in nitrogen displacement still；Nitrogen pressure is adjusted to 5 bar, under mechanical agitation speed is 400 rpm, is warming up to 160 DEG C,
MPV i.e. can get 2,5-dihydroxymethyl furan after reacting 4 h；Understand through gas chromatograph detection, 2,5-dihydroxymethyl furan
Yield reaches 83.7%.
It addition, Zr (OH)4@Fe3O4(3:1) Fourier infrared spectrum analysis as in figure 2 it is shown, wherein, 586 cm–1Ownership
In the stretching vibration peak of Fe O, illustrate in magnetic zirconium hydroxide catalyst containing Fe3O4Component；1090 cm–1The absworption peak at place is returned
Belong to the stretching vibration peak of Zr O, relevant with the acidic site of magnetic zirconium hydroxide catalyst surface；1334 cm¯1, 1450
cm¯1、1545 cm¯1、1626 cm¯1With 3400 cm1The absworption peak at place belongs to Zr (OH)4The stretching vibration of middle O H
Peak, relevant with the basic site of magnetic zirconium hydroxide catalyst surface.
Embodiment 3: be that 1:6 joins and goes with deoxidation by nano ferriferrous oxide by ferrum/zirconium mol ratio under nitrogen atmosphere
In the zirconium chloride solution containing 100 g/L of ionized water preparation, mechanical agitation 90 min, ultrasonic disperse 60 min；Stir at machinery
Mixing speed is under the conditions of 600 rpm to be that 6 mL/min dropwise drip ammonia spirit until pH=by rate of addition in above-mentioned solution
11, continue stirring 30 min, still aging 24 h；By Magnet, solid precipitation is separated, and repeatedly wash with deionized water
Wash precipitation until existing without chloride ion；Solid precipitation after washing is vacuum dried 12 h at 105 DEG C, and is ground
To 200 mesh, obtain magnetic zirconium hydroxide catalyst, referred to as Zr (OH)4@Fe3O4(6:1)；It follows that by 50 g isopropanols, 2.5
G 5 hydroxymethyl furfural and 2.5 g Zr (OH)4@Fe3O4(6:1) join in 100 mL Parr autoclaves, use after sealing
Air in nitrogen displacement still；Nitrogen pressure is adjusted to 10 bar, under mechanical agitation speed is 600 rpm, is warming up to 180 DEG C,
MPV i.e. can get 2,5-dihydroxymethyl furan after reacting 2 h；Understand through gas chromatograph detection, 2,5-dihydroxymethyl furan
Yield reaches 87.8%.
Embodiment 4: be that 1:2 joins and goes with deoxidation by nano ferriferrous oxide by ferrum/zirconium mol ratio under nitrogen atmosphere
In the zirconyl chloride solution containing 80 g/L of ionized water preparation, mechanical agitation 50 min, ultrasonic disperse 40 min；Stir at machinery
Mixing speed is under the conditions of 500 rpm to be that 5 mL/min dropwise drip ammonia spirit until pH=by rate of addition in above-mentioned solution
10, continue stirring 30 min, still aging 24 h；By Magnet, solid precipitation is separated, and repeatedly wash with deionized water
Wash precipitation until existing without chloride ion；Solid precipitation after washing is vacuum dried 12 h at 105 DEG C, and is ground
To 200 mesh, obtain magnetic zirconium hydroxide catalyst, referred to as Zr (OH)4@Fe3O4(2:1)；It follows that by 40 g sec-butyl alcohols, 0.8
G 5 hydroxymethyl furfural and 0.64 g Zr (OH)4@Fe3O4(2:1) join in 100 mL Parr autoclaves, after sealing
With air in nitrogen displacement still；Nitrogen pressure is adjusted to 1 bar, under mechanical agitation speed is 500 rpm, is warming up to 150 DEG C,
MPV i.e. can get 2,5-dihydroxymethyl furan after reacting 6 h；Understand through gas chromatograph detection, 2,5-dihydroxymethyl furan
Yield reaches 91.5%.
It addition, reactant liquor deionized water dilutes, and isolate Zr (OH) with additional Magnet4@Fe3O4(2:1) (Fig. 3), so
After washed and dried directly carried out MPV reaction next time by above-mentioned reaction condition；Result shows: Zr (OH)4@Fe3O4(2:
1) there is higher catalysis activity and catalytic stability, as Zr (OH)4@Fe3O4(2:1) after recycling three times, 2,5-dihydroxy first
The yield of base furan remains able to reach 88.6%.
Claims (6)
1.5-Hydroxymethylfurfural catalysis transfer hydrogenation prepares 2, and the method for 5-dihydroxymethyl furan is characterized in that: with magnetic hydrogen-oxygen
Change zirconium is catalyst, with low-carbon alcohols as reaction dissolvent with hydrogen donor, passes through Meerwein-Ponndorf-in autoclave
Verley(MPV) 5 hydroxymethyl furfural is selectively converted to 2,5-dihydroxymethyl furan by transfer hydrogenation；It includes following
Concrete steps:
(1) synthesis of magnetic zirconium hydroxide catalyst: under nitrogen atmosphere a certain amount of nano ferriferrous oxide is joined use
Deionized deoxygenated water preparation containing in certain density zirconium chloride or zirconyl chloride solution, mechanical agitation 30 ~ 90 min, ultrasonic
Dispersion 10 ~ 60 min；Under mechanical agitation, in above-mentioned solution, dropwise drip ammonia spirit until pH=9 ~ 11, continue to stir
Mix 30 min, still aging 24 h；By Magnet, solid precipitation is separated, and with deionized water cyclic washing precipitation until
Exist without chloride ion；By solid precipitation 105 DEG C vacuum drying 12 h after washing, and ground to 200 mesh, obtained magnetic
Property zirconium hydroxide catalyst；
(2) MPV transfer hydrogenation: a certain amount of magnetic zirconium hydroxide catalyst, 5 hydroxymethyl furfural and low-carbon alcohols are added
In 100 mL Parr autoclaves, with air in nitrogen displacement still after sealing；Nitrogen pressure is adjusted to reaction pressure,
It is warming up to assigned temperature under certain mechanical agitation speed, after the reaction stipulated time, obtains 2,5-dihydroxymethyl furan.
5 hydroxymethyl furfural the most according to claim 1 catalysis transfer hydrogenation prepares 2, the method for 5-dihydroxymethyl furan,
It is characterized in that: the zirconates concentration described in step (1) is 50 ~ 100 g/L, ferrum is 1:1 ~ 1:6 with the mol ratio of zirconium.
5 hydroxymethyl furfural the most according to claim 1 catalysis transfer hydrogenation prepares 2, the method for 5-dihydroxymethyl furan,
It is characterized in that: the mechanical agitation speed described in step (1) is 200 ~ 600 rpm, ammonia rate of addition is 3 ~ 6 mL/min.
5 hydroxymethyl furfural the most according to claim 1 catalysis transfer hydrogenation prepares 2, the method for 5-dihydroxymethyl furan,
It is characterized in that: the low-carbon alcohols described in step (2) is the one in ethanol, normal propyl alcohol, isopropanol, n-butyl alcohol or sec-butyl alcohol, its
Consumption is 20 ~ 50 g.
5 hydroxymethyl furfural the most according to claim 1 catalysis transfer hydrogenation prepares 2, the method for 5-dihydroxymethyl furan,
It is characterized in that: 1 ~ 5 wt% that 5 hydroxymethyl furfural consumption is low-carbon alcohols consumption described in step (2), described magnetic hydrogen-oxygen
Change 20 ~ 100 wt% that zirconium consumption is 5 hydroxymethyl furfural consumption.
5 hydroxymethyl furfural the most according to claim 1 catalysis transfer hydrogenation prepares 2, the method for 5-dihydroxymethyl furan,
It is characterized in that: the nitrogen pressure described in step (2) is 1 ~ 10 bar, described mixing speed is 200 ~ 600 rpm, described
Reaction temperature is 130 ~ 180 DEG C, and the described response time is 2 ~ 8 h.
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| CN106946820A (en) * | 2017-03-29 | 2017-07-14 | 厦门大学 | The synthetic method of 2,5 furyl dimethyl carbinols and its etherification product |
| CN107442177A (en) * | 2017-07-31 | 2017-12-08 | 淮阴师范学院 | The method that 5 hydroxymethylfurfural selective hydrogenations synthesize 2,5 furyl dimethyl carbinols |
| CN108067304A (en) * | 2016-11-17 | 2018-05-25 | 南京农业大学 | A kind of mesoporous function hybrid material and preparation method and application |
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| US8324409B2 (en) * | 2010-04-23 | 2012-12-04 | The Board Of Trustees Of The University Of Illinois | Efficient method for preparing 2,5-dimethylfuran |
| WO2013049711A1 (en) * | 2011-09-29 | 2013-04-04 | Bio Architecture Lab, Inc. | Methods for preparing 2,5-furandicarboxylic acid |
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| CN114573527A (en) * | 2022-03-11 | 2022-06-03 | 湖南师范大学 | Method for preparing 2, 5-dihydroxymethyl furan by transfer hydrogenation of 5-hydroxymethylfurfural |
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