CN114573527B - Method for preparing 2, 5-dimethylolfuran by transferring and hydrogenating 5-hydroxymethylfurfural - Google Patents
Method for preparing 2, 5-dimethylolfuran by transferring and hydrogenating 5-hydroxymethylfurfural Download PDFInfo
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Abstract
The method for preparing 2, 5-dimethylolfuran by transferring and hydrogenating 5-hydroxymethylfurfural takes 5-hydroxymethylfurfural as a reaction substrate, cuO/Bhm as a catalyst and alcohol as a hydrogen donor, and performs transferring and hydrogenating reaction under the nitrogen atmosphere of 0.05-0.15 mpa to obtain the 2, 5-dimethylolfuran. The method has mild reaction conditions, no need of additional hydrogen introduction, simple operation and high product selectivity; the catalytic activity of the used CuO/Bhm catalyst is high; the catalyst is prepared from non-noble metal, and has the advantages of low production cost, simple preparation process, easy separation and high catalytic activity.
Description
Technical Field
The invention relates to a method for preparing 2, 5-dimethylolfuran, in particular to a method for preparing 2, 5-dimethylolfuran by transferring and hydrogenating 5-hydroxymethylfurfural.
Background
2, 5-dimethylol furan (BHMF) is taken as a hydrogenation product of biomass carbohydrate derivative HMF, has both an oxygen-containing rigid cyclic structure and a symmetrical diol functional group, can be used as an intermediate of synthetic drugs and crown ether, and has great application potential in the fields of synthetic resins, polyesters, artificial fibers and the like. Therefore, the preparation of BHMF from biomass carbohydrate conversion for the production of bio-based new materials has a very important strategic meaning for achieving fossil resource replacement.
5-Hydroxymethylfurfural (HMF), which is the main product of biomass carbohydrate deoxygenation, can produce bulk chemicals such as aldehydes, acids, esters, alcohols, ethers, etc. through oxidation, hydrogenation, etherification, etc., is considered to be one of the most promising platform chemicals in biorefinery.
Catalytic hydrogenation reduction of 5-hydroxymethylfurfural is one of the important methods for preparing BHMF. However, the existing preparation method has the defects of harsh reaction conditions, high catalyst cost, poor reaction selectivity,The product is difficult to separate, the production period is long, and the like. The current research of biomass HMF hydrogenation reduction mostly uses hydrogen as a hydrogen source, noble metals Ru, pt, au, ir, pd and supported catalysts thereof, and the used carriers mainly comprise carbon nanotubes, activated carbon, metal oxides and the like. For example, the reaction under the hydrogen atmosphere of HMF catalyzed by Pt/C catalyst can obtain 82% of BHMF yield, but the reaction time is 18 hours, and the production period is longer (see "Etherification and reductive etherification of 5- (hydroxyymethyl) furals and2,5-bis (alkoxymethyl) furans as potential bio-diesel candidates", balakrishanan, green chem.,2012,14,1626-1634). When Ru/ZnAlZr-LDH is used for catalyzing HMF hydrogenation reduction, 94 percent of BHMF yield can be obtained, but the reaction temperature is as high as 200 ℃, the energy consumption is high, and the reaction is dangerous (see 'Heterogeneous zirconia-supported ruthenium catalyst for highly selective hydrogenation of-hydroxyymethyl-2-furaldehyde to 2,5-bis (hydroxymethyl) furans in various n-alcohol solvents', han, RSC adv.,2016,6,93394-93397). The high cost of noble metals is not beneficial to the industrial production of BHMF. In addition, some non-noble metal catalysts can also achieve efficient conversion of HMF to BHMF, e.g., cu/Al 2 O 3 For the catalytic reduction of HMF by the catalyst in a hydrogen atmosphere, 90% BHMF yield can be obtained, however, the main source of hydrogen required for these reactions is petroleum cracking, which is unfavorable for getting rid of the increasingly serious problem of fossil energy depletion, and the safety problem of hydrogen storage and transportation is still a big problem.
CN110698440A discloses a method for preparing 2, 5-dimethylolfuran by solvent-free 5-hydroxymethylfurfural, the used catalyst comprises noble metal catalysts such as Ru/C, pd/C or Pt/C, the reaction temperature is 80-140 ℃, the reaction time is 1-3 h, the hydrogen pressure is 3-6 Mpa, and the yield of the obtained 2, 5-dimethylolfuran is 14.9-93.7%. The method has the advantages of high catalyst cost, high requirement on high-pressure hydrogen, high technical requirement on production equipment and high potential safety hazard.
CN106008414A discloses a method for preparing 2, 5-dimethylolfuran by catalytic transfer hydrogenation of 5-hydroxymethylfurfural, which uses magnetic zirconium hydroxide as a catalyst and low-carbon alcohol5-hydroxymethylfurfural was selectively converted to 2, 5-dimethylolfuran by Meerwein-Ponndorf-Verley (MPV) transfer hydrogenation in an autoclave at a reaction temperature of 150℃with a maximum yield of 91.5% for the reaction solvent and hydrogen donor. However, the method requires a pressure of 1MPa N 2 The reaction is carried out after pressurization, the equipment investment is large, and the operation has safety risks.
Disclosure of Invention
The invention aims to solve the technical problems and overcome the defects in the prior art, and provides the method for preparing the 2, 5-dimethylolfuran, which has the advantages of mild reaction conditions, short reaction time, simple process, high product selectivity and low production cost.
The technical scheme adopted for solving the technical problems is that the method for preparing 2, 5-dimethylolfuran by transferring and hydrogenating 5-hydroxymethylfurfural takes 5-hydroxymethylfurfural as a reaction substrate, takes CuO/Bhm (Boehmite, english: boehmite, bhm for short) as a catalyst, takes alcohol as a hydrogen donor, and performs transferring and hydrogenating reaction to obtain the 2, 5-dimethylolfuran.
Further, in the CuO/Bhm catalyst, the mass fraction of CuO is 10-50wt%; preferably 20 to 40% by weight.
Further, the alcohol includes, but is not limited to, one or more of methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, preferably ethanol.
Further, the temperature of the transfer hydrogenation reaction is 140 to 180 ℃, preferably 150 to 160 ℃.
Further, the transfer hydrogenation reaction time is 1 to 5 hours, preferably 2 to 4 hours.
Further, the transfer hydrogenation reaction is carried out under a nitrogen atmosphere of 0.05 to 0.15Mpa, preferably 0.1Mpa.
Further, the amount of the CuO/Bhm catalyst is 50-180% by mass, preferably 70-140% by mass of the 5-hydroxymethylfurfural. Too small a mass ratio may result in insufficient active centers, resulting in reduced HMF conversion, and too large a mass ratio may result in reduced selectivity of the reaction product.
Further, the CuO/Bhm catalyst is prepared by the following method:
(1) Dissolving copper salt in deionized water, adding Bhm, and mixing to obtain suspension; regulating the suspension to be alkaline, heating and stirring, then carrying out solid-liquid separation, collecting solids, and drying the solids to obtain a CuO/Bhm catalyst precursor;
(2) And (3) roasting the CuO/Bhm catalyst precursor obtained in the step (1) in a nitrogen atmosphere to obtain the CuO/Bhm catalyst.
Further, in the step (1), the heating temperature is 50 to 70 ℃, preferably 55 to 65 ℃, more preferably 58 to 62 ℃, still more preferably 60 ℃; the heating time is 3 to 6 hours, preferably 3.5 to 4.5 hours, more preferably 4 hours.
Further, in the step (2), the baking temperature is 350 to 600 ℃, preferably 380 to 420 ℃, more preferably 400 ℃; the calcination time is 1 to 3 hours, preferably 1.5 to 2.5 hours, more preferably 2 hours.
Further, in the step (1), the alkaline means a pH of 7.5 to 9.0, preferably 7.8 to 8.2, more preferably 8.
Further, in step (1), the copper salt is copper nitrate trihydrate.
Reaction mechanism: the CuO/Bhm catalyst used in the present invention contains Lewis base (O) 2- ) And Lewis acid (Al) 3+ ) The Lewis base and the Lewis acid cooperate with each other to realize the professional hydrogenation reaction of the substrate: first, HMF and alcohol are adsorbed on the catalyst surface, and then the oxygen atom and hydrogen atom of the alcohol hydroxyl group are respectively adsorbed on O on the catalyst 2- And Al 3+ Activated, while the oxygen and carbon atoms on the aldehyde group of HMF are respectively replaced by O 2- And Al 3+ Activating, and then forming a six-membered ring intermediate by hydroxyl on alcohol and aldehyde on HMF, and completing catalytic transfer hydrogenation reaction to BHMF along with electron transfer; at the same time, protonic acid (H on hydroxy group) contained in Bhm + ) Firstly, forming oxonium with hydroxyl on BHMF, forming carbonium ion after dehydration, then reacting with alcohol for etherification to form byproduct 2-hydroxymethyl-5-ethoxymethyl furan (HEMF), and reducing the amount of proton acid on Bhm surface by introducing CuO.
Compared with the prior art, the invention has the following beneficial effects: (1) According to the invention, cuO/Bhm is used as a catalyst, alcohol is used as a hydrogen donor, the transfer hydrogenation of 5-hydroxymethylfurfural is efficiently catalyzed to 2, 5-dimethylolfuran, no additional hydrogen is needed in the reaction, the reaction can be performed in a nitrogen atmosphere of 0.05-0.15 Mpa after air is replaced by nitrogen, the reaction condition is mild, the operation is simple and convenient, the safety coefficient is high, the selectivity and conversion rate of the product are high, the conversion rate is up to 98.4%, and the selectivity is up to 95.9%; (2) The raw materials used for manufacturing the catalyst CuO/Bhm are all non-noble metals, so that the production cost of the catalyst is greatly reduced, the economic benefit of BHMF production is improved, the efficient conversion of biomass resources is realized, and practical support is provided for comprehensive utilization and industrialization of biomass resources.
Drawings
FIG. 1 is an X-ray diffraction pattern of CuO/Bhm catalysts of varying copper oxide content.
Fig. 2 is a schematic diagram of the mechanism of HMF hydrogenation reduction at the catalyst surface active sites.
FIG. 3 is Bhm and 40wt.% CuO/Bhm O 1s X-ray photoelectron spectroscopy analysis graph.
Fig. 4 is a standard graph of HMF.
Fig. 5 is a standard graph of BHMF.
Note that: a in fig. 4 and 5 i And A is a s Respectively the peak area of the gas chromatogram standard sample and the peak area of the internal standard substance, m i And m is equal to s The mass of the standard sample and the mass of the internal standard substance are respectively.
Detailed Description
The invention will be further described with reference to the drawings and the specific examples.
The chemical reagents used in the examples were obtained from conventional commercial sources, unless otherwise specified.
Quantitative analysis of the product: and (5) calculating the contents of the HMF and BHMF components by adopting an internal standard method.
The standard solution was subjected to gas phase analysis by the test, and a standard curve was drawn (see fig. 4 to 5). The content of the component to be measured can be calculated by using a standard curve.
The calculation formula is as follows:
HMF conversion = converted HMF molar mass/HMF feed mass
BHMF selectivity = moles of BHMF converted/moles of tetrahydrofuran converted
Yield of BHMF = mole amount of BHMF converted/HMF feed
Example 1
The operation steps of this embodiment are: preparing 126mg of 5-hydroxymethylfurfural and 10mL of ethanol into a reaction substrate solution, adding 100mg of 10wt.% (namely, 10% of the copper oxide by mass of the total catalyst) of a CuO/Bhm catalyst into the reaction substrate solution, mixing, placing the mixture into a closed reaction kettle, performing transfer hydrogenation reaction for 3h at 160 ℃ in a nitrogen atmosphere of 0.1Mpa after replacing air with nitrogen, and controlling the stirring speed to be 400r/min to obtain 2, 5-dimethylolfuran; the consumption of the CuO/Bhm catalyst is 79.3% of the mass of the 5-hydroxymethylfurfural;
wherein, the CuO/Bhm catalyst is prepared by the following steps:
(1) 0.8804g of copper nitrate trihydrate is dissolved in 200mL of deionized water, stirred for 10min, uniformly mixed, added with 2gBhm and stirred to obtain a suspension; then dropwise adding 0.1mol/L NaOH aqueous solution into the suspension, adjusting the pH value of the suspension to 8, stirring at 60 ℃ for reaction for 4 hours, and suction filtering to obtain a catalyst precursor;
(2) And (3) heating the CuO/Bhm catalyst precursor obtained in the step (1) from 50 ℃ to 400 ℃ at a heating rate of 5 ℃ per minute in a nitrogen atmosphere, and roasting for 2 hours to obtain the CuO/Bhm catalyst.
The conversion rate of the 2, 5-dimethylolfuran prepared by transferring and hydrogenating the 5-hydroxymethylfurfural in the embodiment is 72.7%, and the selectivity of the product is 87.8%. Details are shown in Table 1.
Example 2
This example differs from example 1 in that the mass fraction of CuO in the CuO/Bhm catalyst used was increased to 20wt.%, i.e. 100mg of 20wt.% CuO/Bhm catalyst was used instead of 100mg of 10wt.% CuO/Bhm catalyst in example 1, as in example 1.
The conversion rate of the 2, 5-dimethylolfuran prepared by transferring and hydrogenating the 5-hydroxymethylfurfural in the embodiment is 71.6 percent and the selectivity of the product is 91.2 percent.
Example 3
This example differs from example 1 in that the mass fraction of CuO in the CuO/Bhm catalyst used was increased to 30wt.%, i.e. 100mg 30wt.% CuO/Bhm catalyst was used instead of 100mg10wt.% CuO/Bhm catalyst in example 1, as in example 1.
The conversion rate of the 2, 5-dimethylolfuran prepared by transferring and hydrogenating the 5-hydroxymethylfurfural in the embodiment is 72.5%, and the product selectivity is 90.2%.
Example 4
This example differs from example 1 in that the mass fraction of CuO in the CuO/Bhm catalyst is increased to 40wt.%, and 100mg of the 40wt.% CuO/Bhm catalyst is substituted for 100mg of the 10wt.% CuO/Bhm catalyst in example 1, as in example 1.
The conversion rate of the 2, 5-dimethylolfuran prepared by transferring and hydrogenating the 5-hydroxymethylfurfural in the embodiment is 69.4%, and the product selectivity is 96.9%.
Example 5
The difference between this example and example 4 is that the temperature of the transfer hydrogenation reaction is reduced to 140 ℃, the reaction time is unchanged, and the reaction time is still 3 hours; example 4 is followed.
The conversion rate of the 2, 5-dimethylolfuran prepared by transferring and hydrogenating the 5-hydroxymethylfurfural in the embodiment is 56.0%, and the product selectivity is 98.9%.
Example 6
The difference between this example and example 4 is that the temperature of the transfer hydrogenation is increased to 180 ℃, the reaction time is unchanged and is still 3 hours; example 4 is followed.
The conversion rate of the 2, 5-dimethylolfuran prepared by transferring and hydrogenating the 5-hydroxymethylfurfural in the embodiment is 91.7%, and the product selectivity is 93.8%.
Example 7
The difference between this example and example 4 is that ethanol was replaced with n-propanol, in an unchanged amount, still 10mL; example 4 is followed.
The conversion rate of the 2, 5-dimethylolfuran prepared by transferring and hydrogenating the 5-hydroxymethylfurfural in the embodiment is 22.6 percent and the product selectivity is 87.3 percent.
Example 8
The difference between this example and example 4 is that ethanol is replaced with isopropanol, in an unchanged amount, still 10mL; example 4 is followed.
The conversion rate of the 2, 5-dimethylolfuran prepared by transferring and hydrogenating the 5-hydroxymethylfurfural in the embodiment is 40.3%, and the product selectivity is 94.2%.
Example 9
This example differs from example 4 in that the ethanol was replaced with n-butanol, in an unchanged amount, still 10mL, as in example 4.
The conversion rate of the 2, 5-dimethylolfuran prepared by transferring and hydrogenating the 5-hydroxymethylfurfural in the embodiment is 28.3%, and the product selectivity is 63.0%.
Example 10
This example differs from example 4 in that ethanol was replaced with isobutanol, in an unchanged amount, still 10mL, with the remainder being the same as example 4.
The conversion rate of the 2, 5-dimethylolfuran prepared by transferring and hydrogenating the 5-hydroxymethylfurfural in the embodiment is 21.8%, and the product selectivity is 70.6%.
Example 11
This example differs from example 4 in that the amount of 40wt.% CuO/Bhm catalyst was reduced to 75mg, the CuO/Bhm catalyst being used in an amount of 59.5% of the mass of 5-hydroxymethylfurfural; the duration of the transfer hydrogenation reaction is reduced to 2 hours, and the reaction temperature is kept at 160 ℃; the procedure was as in example 4.
The conversion rate of the 2, 5-dimethylolfuran prepared by transferring and hydrogenating the 5-hydroxymethylfurfural in the embodiment is detected to be 51.5%, and the selectivity of the product is 98.52%.
Example 12
This example differs from example 11 in that the amount of 40wt.% CuO/Bhm catalyst was increased to 125mg, the CuO/Bhm catalyst being used in an amount of 99.2% of the mass of 5-hydroxymethylfurfural; example 11 is followed.
The conversion rate of the 2, 5-dimethylolfuran prepared by transferring and hydrogenating the 5-hydroxymethylfurfural in the embodiment is 73.9%, and the product selectivity is 97.3%.
Example 13
This example differs from example 11 in that the amount of 40wt.% CuO/Bhm catalyst was increased to 175mg, the CuO/Bhm catalyst being used in an amount of 138.9% by mass of 5-hydroxymethylfurfural; example 11 is followed.
The conversion rate of the 2, 5-dimethylolfuran prepared by transferring and hydrogenating the 5-hydroxymethylfurfural in the embodiment is 98.4%, and the product selectivity is 95.9%.
Example 14
This example differs from example 11 in that the amount of 40wt.% CuO/Bhm catalyst is increased to 225mg, the CuO/Bhm catalyst being used in an amount of 178.5% by mass of 5-hydroxymethylfurfural; example 11 is followed.
The conversion rate of the 2, 5-dimethylolfuran prepared by transferring and hydrogenating the 5-hydroxymethylfurfural in the embodiment is 99.5%, and the product selectivity is 77.1%.
TABLE 1 detection results of the reaction conditions and the obtained parameters related to 2, 5-dimethylolfuran for examples 1 to 14 of the present invention
Claims (10)
1. A method for preparing 2, 5-dimethylolfuran by transferring hydrogenation of 5-hydroxymethylfurfural is characterized in that the 2, 5-dimethylolfuran is obtained by transferring hydrogenation reaction of 5-hydroxymethylfurfural serving as a reaction substrate and CuO/Bhm serving as a catalyst and alcohol serving as a hydrogen donor; the Bhm is boehmite.
2. The method for preparing 2, 5-dimethylolfuran by transferring and hydrogenating 5-hydroxymethylfurfural according to claim 1, wherein the mass fraction of CuO in the CuO/Bhm catalyst is 10-50wt%。
3. The method for preparing 2, 5-dimethylolfuran by transferring hydrogenation of 5-hydroxymethylfurfural according to claim 1, wherein the alcohol is one or more of methanol, ethanol, n-propanol, isopropanol, n-butanol and isobutanol.
4. A method for preparing 2, 5-dimethylolfuran by transfer hydrogenation of 5-hydroxymethylfurfural according to one of claims 1 to 3, characterized in that the temperature of the transfer hydrogenation reaction is 140 to 180 ℃; the transfer hydrogenation reaction time is 1-5 h.
5. The method for preparing 2, 5-dimethylolfuran by transferring hydrogenation of 5-hydroxymethylfurfural according to one of claims 1 to 3, wherein the transferring hydrogenation reaction is performed in a nitrogen atmosphere of 0.05 to 0.15 MPa.
6. The method for preparing 2, 5-dimethylolfuran by transferring hydrogenation of 5-hydroxymethylfurfural according to one of claims 1 to 3, wherein the amount of CuO/Bhm catalyst is 50 to 180% of the mass of 5-hydroxymethylfurfural.
7. A method for preparing 2, 5-dimethylolfuran by transferring hydrogenation of 5-hydroxymethylfurfural according to one of claims 1 to 3, characterized in that the CuO/Bhm catalyst is prepared by the following method:
(1) Dissolving copper salt in deionized water, adding Bhm, and mixing to obtain suspension; regulating the suspension to be alkaline, heating and stirring, then carrying out solid-liquid separation, collecting solids, and drying the solids to obtain a CuO/Bhm catalyst precursor;
(2) And (3) roasting the CuO/Bhm catalyst precursor obtained in the step (1) in a nitrogen atmosphere to obtain the CuO/Bhm catalyst.
8. The method for preparing 2, 5-dimethylolfuran by transferring hydrogenation of 5-hydroxymethylfurfural according to claim 7, wherein in the step (1), the heating temperature is 50-70 ℃; and the heating time is 3-6 hours.
9. The method for preparing 2, 5-dimethylolfuran by transferring hydrogenation of 5-hydroxymethylfurfural according to claim 7, wherein in the step (2), the roasting temperature is 400-600 ℃; and the roasting time is 1-3 hours.
10. The method for preparing 2, 5-dimethylolfuran by transferring hydrogenation of 5-hydroxymethylfurfural according to claim 7, wherein in the step (1), the alkalinity means a pH value of 8-9.
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| EP2487170B1 (en) * | 2007-09-07 | 2015-02-18 | Furanix Technologies B.V | 5-substituted 2-(alkoxymethyl)furans |
| CN105143211A (en) * | 2013-04-25 | 2015-12-09 | 阿彻丹尼尔斯米德兰德公司 | Catalytic synthesis of reduced furan derivatives |
| JP6369828B2 (en) * | 2014-06-05 | 2018-08-08 | 国立研究開発法人産業技術総合研究所 | Method for reducing hydroxymethylfurfural |
| CN106008414B (en) * | 2016-07-13 | 2018-04-10 | 淮阴师范学院 | The method that 5 hydroxymethylfurfurals catalysis transfer hydrogenation prepares 2,5 dihydroxymethyl furans |
| KR102133304B1 (en) * | 2018-11-16 | 2020-07-13 | 한국생산기술연구원 | Method of preparing 2,5-furandimethanol and 2,5-tetrahydrofuran dimethanol from 5-hydroxymethylfurfural |
| KR102293261B1 (en) * | 2019-11-15 | 2021-08-23 | 한양대학교 산학협력단 | Supported Copper Catalyst and Selective Hydrogenation of Furan-based Compounds Using the Same |
| CN111875566B (en) * | 2020-08-21 | 2022-11-29 | 湖南师范大学 | Method for preparing 2, 5-dimethylfuran |
| CN112536038B (en) * | 2020-12-04 | 2022-06-28 | 东南大学 | Alpha, beta-unsaturated aldehyde selective hydrogenation conversion catalyst, and preparation method and application thereof |
| CN114105914B (en) * | 2021-11-04 | 2023-03-17 | 厦门大学 | Method for preparing 2, 5-furandimethanol by using 5-chloromethyl furfural |
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