CN108722495B - Bifunctional catalyst for catalyzing fructose to directly prepare 2, 5-dimethylfuran in one step - Google Patents
Bifunctional catalyst for catalyzing fructose to directly prepare 2, 5-dimethylfuran in one step Download PDFInfo
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Abstract
The invention discloses a bifunctional catalyst for catalyzing fructose to directly prepare 2, 5-dimethylfuran in one step, which is a carbon-based solid acid-coated non-noble metal core-shell type catalyst, wherein the carbon-based solid acid is carbon-based p-toluenesulfonic acid, carbon-based heteropoly acid, carbon-based niobic acid or carbon-based sulfonic acid, and the non-noble metal is at least one of Cu, Co, Ni, Mn, Mo, Fe and Zn. The catalyst provided by the invention is low in cost, the preparation method is simple, the 2, 5-dimethylfuran can be prepared at high yield by catalyzing fructose in one step, the intermediate product 5-hydroxymethylfurfural does not need to be purified, the highest yield of the 2, 5-dimethylfuran reaches 71.1%, and the catalyst is simple and safe to operate and has a good industrial application prospect.
Description
Technical Field
The invention belongs to the technical field of clean and green catalytic synthesis of high value-added chemicals by utilizing biomass resources, and particularly relates to a bifunctional catalyst for catalyzing fructose to directly prepare 2, 5-dimethylfuran and a method for catalytically synthesizing 2, 5-dimethylfuran by using the bifunctional catalyst.
Background
With the increasing shortage of petrochemical resources and the series of environmental problems brought by the use process, people are forced to seek to replace petrochemical resources with renewable resources as raw materials to produce liquid fuels and basic chemicals. The biomass is a renewable resource with wide sources, the preparation of liquid fuel and basic chemicals by using the biomass as a raw material meets the requirements of sustainable development, not only can people get rid of the dependence on petrochemical resources, but also can realize CO2Virtuous circle and environmental problems such as greenhouse effect and the like are reduced.
The 2, 5-dimethylfuran is liquid at normal temperature and has high energy density (30 kJ/cm)3) High boiling point (92-94 ℃), high octane number (120 ℃) and excellent hydrophobicity, and is considered to be an excellent liquid fuel or gasoline additive. The preparation of the 2, 5-dimethylfuran by taking the biomass derivative fructose as the raw material is one of important alternative petroleum energy routes, and is helpful for relieving the current dilemma of increasingly exhausted petroleum resources.
Currently, the majority of 2, 5-dimethylfuran production from fructose uses a two-step process: (1) the fructose is catalyzed and dehydrated by acid to generate 5-hydroxymethyl furfural, and (2) the 5-hydroxymethyl furfural is catalyzed and hydrogenated by a supported metal catalyst to generate 2, 5-dimethyl furan. Although the two-step process can obtain high yield of 2, 5-dimethylfuran, the two-step process is complicated, energy consumption is high, and it is necessary to purify 5-hydroxymethylfurfural from a dehydration reaction mixture at high cost. The one-pot one-step method for preparing 2, 5-dimethylfuran from fructose does not need to purify 5-hydroxymethylfurfural in a dehydration reaction mixture, so that the process steps can be greatly reduced, and the energy consumption and the cost are reduced. Abu-Omar et al (ChemSusChem,2014,7, 3095-S3101) employ ZnCl2the-Pd/C catalyst takes fructose as a raw material, and the fructose is reacted in a tetrahydrofuran solvent at 150 ℃ and under 0.8MPa hydrogen for 8 hours to obtain the yield of 22 mol% 2, 5-dimethylfuran. Zhu et al (ACS Sustain. chem. Eng.,2016,4, 4506-containing 4510) packed HY molecular sieve and CuZnAl catalyst separately in two stages in a fixed bed, and continuously hydrogenated fructose at 240 deg.c to reach 2, 5-dimethyl furan yield of 40.6 mol%. Wei et al (Catal. Sci. Tech.,2016,6,6217-3/H2SO4/H3PO4) And a heterogeneous catalyst Ru/C, taking fructose as a raw material, reacting in hydrogen and N, N-dimethylformamide at 200 ℃ and 1.5MPa for 12h to obtain the yield of 66 mol% of 2, 5-dimethylfuran. The literature reports that the yield of the 2, 5-dimethylfuran prepared by the fructose one-step method is low, the homogeneous catalyst is not favorable for product separation, and the corrosion-prone equipment is not favorable for industrial production. However, Jaehon Kim et al (Green chem.,2017,19,2482-2490) adopt sulfonated graphene oxide coated UiO-66 loaded Pd (4.8Pd/UiO-66@ SGO) to react in tetrahydrofuran solvent at 160 ℃ and 1MPa for 3h to obtain a yield of 70.5% of 2, 5-dimethylfuran, which is the highest yield of fructose one-step method 2, 5-dimethylfuran reported in the literature at present, but they use a high-loaded noble metal Pd catalyst, and the preparation process of the catalyst is complex and the cost is high, so that the catalyst is not beneficial to large-scale industrial application.
Disclosure of Invention
The invention aims to overcome the defects of multiple reaction steps, complex operation, high energy consumption, high catalyst cost and the like in the prior art for preparing 2, 5-dimethylfuran, and provides the bifunctional catalyst which has simple process, low cost and high efficiency and catalyzes fructose to prepare 2, 5-dimethylfuran in one step.
Aiming at the purposes, the bifunctional catalyst is a core-shell type catalyst with non-noble metal wrapped by carbon-based solid acid, wherein the carbon-based solid acid comprises carbon-based p-toluenesulfonic acid, carbon-based heteropolyacid, carbon-based niobic acid, carbon-based sulfonic acid and the like, and the carbon-based heteropolyacid is carbon-based silicotungstic acid, carbon-based phosphotungstic acid, carbon-based phosphomolybdic acid and the like; the non-noble metal comprises one or more than two alloys of Cu, Co, Ni, Mn, Mo, Fe and Zn.
In the above bifunctional catalyst, the carbon-based solid acid is preferably carbon-based p-toluenesulfonic acid, and the non-noble metal is an alloy of Cu and Co.
In the bifunctional catalyst, the mass percentage content of the non-noble metal core is 5-40%.
The preparation method of the bifunctional catalyst comprises the following steps: dissolving non-noble metal soluble salt in deionized water, adding tartaric acid and polyethylene glycol, adding a mixture of glycerol and water in a volume ratio of 4:1, performing ultrasonic dispersion uniformly, then loading into a hydrothermal kettle, performing hydrothermal reaction at 140-160 ℃ for 10-15 h, performing centrifugal separation after the hydrothermal reaction is finished, washing with absolute ethyl alcohol, drying, and treating at 400-800 ℃ for 1-2 h in an inert atmosphere to obtain a carbon-coated non-noble metal core; uniformly dispersing the carbon-coated non-noble metal core and the solid acid in absolute ethyl alcohol according to the mass ratio of 1:1, soaking at room temperature for 10-12 h, and drying after soaking to obtain the carbon-based solid acid-coated non-noble metal core-shell catalyst, namely the bifunctional catalyst.
The non-noble metal soluble salt is one or a mixture of more than two of copper nitrate, cobalt nitrate, nickel nitrate, manganese nitrate, ferric nitrate, zinc nitrate and ammonium molybdate; the solid acid is any one of p-toluenesulfonic acid, heteropoly acid, niobic acid and sulfonic acid, wherein the heteropoly acid is any one of silicotungstic acid, phosphotungstic acid and phosphomolybdic acid.
In the preparation method of the bifunctional catalyst, the ratio of the amount of the metal element in the non-noble metal soluble salt to the amount of the tartaric acid is preferably 1: 1-1: 4; the ratio of the amount of metal elements in the non-noble metal soluble salt to the amount of polyethylene glycol is 10: 1-5: 1, wherein the number average molecular weight of the polyethylene glycol is 6000-10000.
In the above-mentioned method for producing a bifunctional catalyst, the hydrothermal reaction is preferably carried out at 150 ℃ for 12 hours.
In the preparation method of the bifunctional catalyst, the bifunctional catalyst is preferably treated for 2-3 hours at 550-650 ℃ in an inert atmosphere.
The bifunctional catalyst is a core-shell type catalyst, namely the bifunctional catalyst, which is prepared by preparing a carbon-coated non-noble metal precursor by a Pechini sol-gel method, pyrolyzing the precursor in an inert atmosphere to obtain a carbon-coated non-noble metal core, and then impregnating the obtained carbon-coated non-noble metal core with solid acid to obtain the carbon-based solid acid-coated non-noble metal.
The bifunctional catalyst provided by the invention is mainly based on non-noble metal, is cheap and easy to obtain, is low in cost, can be used for preparing 2, 5-dimethylfuran in one step with high yield from fructose, has the reaction process steps of one-pot one-step method, does not need to purify an intermediate product, namely 5-hydroxymethylfurfural, is simple in process and safe to operate, and has a good industrial application prospect.
Detailed Description
The present invention will be described in further detail with reference to examples, but the scope of the present invention is not limited to these examples.
EXAMPLE 1
0.3016g (1.25mmol) Cu (NO) were weighed out3)2·3H2O and 1.0912g (3.75mmol) Co (NO)3)2·6H2Dissolving O in 16mL of deionized water, adding 1.5g (10mmol) of tartaric acid, 4.0g (0.67mmol) of polyethylene glycol with the number average molecular weight of 6000 and 48mL of a mixture of glycerol and water in a volume ratio of 4:1, carrying out ultrasonic treatment for 3h, then placing in an 80mL hydrothermal kettle, and carrying out hydrothermal synthesis at 150 ℃ for 13 h. After the hydrothermal reaction is finished, centrifugal separation is carried out, absolute ethyl alcohol is used for washing for 3 times, drying is carried out at 100 ℃ overnight, and the mixture is subjected to N2Processing for 2h at 600 ℃ in the atmosphere to obtain CuCo @ C, uniformly dispersing CuCo @ C and TsOH with equal mass in absolute ethyl alcohol, soaking for 12h, and drying for 6h at 80 ℃ after soaking is completed to obtain the carbon-based p-toluenesulfonic acid coated copper-cobalt bimetallic catalyst (CuCo @ C-TsOH).
Example 2
In the embodiment, the preparation method of CuCo @ C is the same as that of embodiment 1, CuCo @ C and phosphomolybdic acid (HPMo) with equal mass are uniformly dispersed in absolute ethyl alcohol to be soaked for 12 hours, and after the soaking is finished, the drying is carried out for 6 hours at 80 ℃ to obtain the carbon-based phosphomolybdic acid coated copper-cobalt bimetallic catalyst (CuCo @ C-HPMo).
Example 3
In the embodiment, the preparation method of CuCo @ C is the same as that in embodiment 1, CuCo @ C and silicotungstic acid (HSiW) with equal mass are uniformly dispersed in absolute ethyl alcohol for soaking for 12 hours, and after the soaking is completed, drying is carried out at 80 ℃ for 6 hours, so that the carbon-based silicotungstic acid coated copper-cobalt bimetallic catalyst (CuCo @ C-HSiW) is obtained.
Example 4
In the embodiment, the preparation method of CuCo @ C is the same as that in embodiment 1, CuCo @ C and phosphotungstic acid (HPW) with equal mass are uniformly dispersed in absolute ethyl alcohol to be soaked for 12 hours, and after the soaking is completed, drying is carried out at 80 ℃ for 6 hours, so that the carbon-based phosphotungstic acid coated copper-cobalt bimetallic catalyst (CuCo @ C-HPW) is obtained.
Example 5
In this example, Cu (NO) was not added3)2·3H2And O, the other steps are the same as the example 1, and the carbon-based p-toluenesulfonic acid coated cobalt catalyst (Co @ C-TsOH) is obtained.
Example 6
In example 1, Cu (NO)3)2·3H2O is replaced by equimolar nickel acetate, and other steps are the same as the example 1, so that the carbon-based p-toluenesulfonic acid coated nickel-cobalt catalyst (NiCo @ C-TsOH) is obtained.
Example 7
In example 1, Cu (NO)3)2·3H2O is replaced by equimolar ammonium molybdate, and other steps are the same as the steps in the example 1, so that the carbon-based p-toluenesulfonic acid coated molybdenum cobalt catalyst (MoCo @ C-TsOH) is obtained.
Example 8
In example 1, Cu (NO)3)2·3H2Equimolar Fe (NO) for O3)2·9H2O replacement and other steps are the same as example 1, and a carbon-based p-toluenesulfonic acid coated iron-cobalt catalyst (FeCo @ C-TsOH) is obtained.
In order to prove the beneficial effects of the invention, the inventor uses the catalyst prepared in the embodiment 1-8 to catalyze fructose to prepare 2, 5-dimethylfuran, and the specific method is as follows:
0.2g of catalyst, 0.2g of fructose and 40mL of tetrahydrofuran are put into a 100mL stainless steel reaction kettle, after the reaction kettle is closed, the gas in the reaction kettle is replaced by nitrogen for 3 times, then 3MPa hydrogen is filled, the temperature is raised to 220 ℃, the stirring is started to 500 revolutions per minute, and the reaction is carried out for 10 hours. And cooling the reaction kettle in an ice-water bath after the reaction is finished, filtering to obtain reaction liquid, analyzing the reaction liquid by gas chromatography, and taking n-butanol as an internal standard substance. The reaction results of the examples are shown in Table 1.
TABLE 1 fructose conversion and 2, 5-dimethylfuran yield for different catalysts
As shown in Table 1, the catalyst can be used for preparing 2, 5-dimethylfuran in one step at high yield by catalyzing fructose without purifying an intermediate product, namely 5-hydroxymethylfurfural, and the highest yield of the 2, 5-dimethylfuran reaches 71.1 mol%.
Claims (9)
1. A bifunctional catalyst for catalyzing fructose to directly prepare 2, 5-dimethylfuran in one step is characterized in that: the bifunctional catalyst is a core-shell catalyst with non-noble metal wrapped by carbon-based solid acid, wherein the carbon-based solid acid is any one of carbon-based p-toluenesulfonic acid, carbon-based heteropoly acid, carbon-based niobic acid and carbon-based sulfonic acid, and the non-noble metal is an alloy of more than two of Cu, Co, Ni, Mn, Mo, Fe and Zn;
the preparation method of the bifunctional catalyst comprises the following steps: dissolving non-noble metal soluble salt in deionized water, adding tartaric acid and polyethylene glycol, adding a mixture of glycerol and water in a volume ratio of 4:1, performing ultrasonic dispersion uniformly, then loading into a hydrothermal kettle, performing hydrothermal reaction at 140-160 ℃ for 10-15 h, performing centrifugal separation after the hydrothermal reaction is finished, washing with absolute ethyl alcohol, drying, and treating at 400-800 ℃ for 1-2 h in an inert atmosphere to obtain a carbon-coated non-noble metal core; uniformly dispersing a carbon-coated non-noble metal core and solid acid in absolute ethyl alcohol according to the mass ratio of 1:1, soaking at room temperature for 10-12 h, and drying after soaking to obtain a core-shell catalyst, namely a bifunctional catalyst, of which the carbon-based solid acid coats the non-noble metal;
the non-noble metal soluble salt is a mixture of more than two of copper nitrate, cobalt nitrate, nickel nitrate, manganese nitrate, ferric nitrate, zinc nitrate and ammonium molybdate;
the solid acid is any one of p-toluenesulfonic acid, heteropoly acid, niobic acid and sulfonic acid.
2. Bifunctional catalyst according to claim 1, characterized in that: the carbon-based solid acid is carbon-based p-toluenesulfonic acid, and the non-noble metal is an alloy of Cu and Co.
3. Bifunctional catalyst according to claim 1, characterized in that: the carbon-based heteropolyacid is any one of carbon-based silicotungstic acid, carbon-based phosphotungstic acid and carbon-based phosphomolybdic acid.
4. Bifunctional catalyst according to any of claims 1 to 3 characterized in that: the mass percentage content of non-noble metal cores in the catalyst is 5-40%.
5. Bifunctional catalyst according to claim 1, characterized in that: the heteropoly acid is any one of silicotungstic acid, phosphotungstic acid and phosphomolybdic acid.
6. Bifunctional catalyst according to claim 1, characterized in that: the ratio of the amount of metal elements in the non-noble metal soluble salt to the amount of tartaric acid is 1: 1-1: 4; the ratio of the amount of the metal element to the amount of the polyethylene glycol in the non-noble metal soluble salt is 10:1 to 5: 1.
7. Bifunctional catalyst according to claim 6, characterized in that: the number average molecular weight of the polyethylene glycol is 6000-10000.
8. Bifunctional catalyst according to claim 1, characterized in that: the hydrothermal reaction was carried out at 150 ℃ for 12 hours.
9. Bifunctional catalyst according to claim 1, characterized in that: treating for 2-3 h at 550-650 ℃ in an inert atmosphere.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013535544A (en) * | 2010-07-26 | 2013-09-12 | ウオーターズ・テクノロジーズ・コーポレイシヨン | Surface porous material containing a substantially non-porous hybrid core with narrow particle size distribution |
| CN105251491A (en) * | 2015-11-09 | 2016-01-20 | 中国科学院化学研究所 | Catalyst for preparing 2,5-dimethylfuran through selective hydrogenolysis of 5-hydroxymethylfurfural and preparation method of catalyst |
| CN106215951A (en) * | 2016-07-29 | 2016-12-14 | 中国科学院广州能源研究所 | A kind of core-shell structure magnetic carbon-based solid acid catalyst and preparation method thereof and the application during lignocellulose hydrolysis and saccharification |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013535544A (en) * | 2010-07-26 | 2013-09-12 | ウオーターズ・テクノロジーズ・コーポレイシヨン | Surface porous material containing a substantially non-porous hybrid core with narrow particle size distribution |
| CN105251491A (en) * | 2015-11-09 | 2016-01-20 | 中国科学院化学研究所 | Catalyst for preparing 2,5-dimethylfuran through selective hydrogenolysis of 5-hydroxymethylfurfural and preparation method of catalyst |
| CN106215951A (en) * | 2016-07-29 | 2016-12-14 | 中国科学院广州能源研究所 | A kind of core-shell structure magnetic carbon-based solid acid catalyst and preparation method thereof and the application during lignocellulose hydrolysis and saccharification |
Non-Patent Citations (3)
| Title |
|---|
| Selective and Flexible Transformation of Biomass-Derived Platform Chemicals by a Multifunctional Catalytic System;Frank M. A. Geilen等;《Angewandte Chemie》;20101231;第122卷;全文 * |
| 球形核壳结构磁性碳基固体酸的制备及应用;刘姗姗 等;《应用化工》;20150831;第44卷(第8期);全文 * |
| 选择性热化学催化转化果糖制备5-甲基糠醛和糠醛;徐禄江 等;《科学通报》;20151231;第60卷(第16期);全文 * |
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