CN113559861A - Cu-Ni bimetallic catalyst for directly converting furfural into tetrahydrofurfuryl alcohol, preparation method and application - Google Patents
Cu-Ni bimetallic catalyst for directly converting furfural into tetrahydrofurfuryl alcohol, preparation method and application Download PDFInfo
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- 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
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- 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
Abstract
A Cu-Ni bimetallic catalyst for directly converting furfural into tetrahydrofurfuryl alcohol, a preparation method and application thereof belong to the technical field of biomass catalytic conversion. The method utilizes a layered structure with high specific surface area of hydrotalcite as a carrier to load Cu and Ni, directly uses hydrogen molecules to activate a Cu-Ni bimetallic precursor loaded based on an MgAl-LDH precursor without roasting, and prepares the novel Cu-Ni bimetallic catalyst with high metal loading and high dispersion of active metal. The catalyst can be used for hydrogenating furfural to tetrahydrofurfuryl alcohol in one step, and the yield of the tetrahydrofurfuryl alcohol can reach 94%. The Cu-Ni bimetallic catalyst has the advantages of uniform distribution of active sites, small crystal grains, large specific surface area, capability of inhibiting sintering and good stability. In addition, the method has the advantages of simple and convenient process, low production cost, mild reaction conditions, high yield of target products, low energy consumption, continuous use of the catalyst and the like, and has good industrial application prospect.
Description
Technical Field
The invention relates to a method for preparing tetrahydrofurfuryl alcohol, in particular to a preparation method and application of a Cu-Ni bimetallic catalyst for directly converting furfural into tetrahydrofurfuryl alcohol, and belongs to the technical field of biomass catalytic conversion.
Background
Furfural is one of typical representatives of alpha, beta-unsaturated aldehyde, is an important biomass-based platform molecule, has very special research significance, and is widely applied to various industries such as medicine, pesticide, daily chemical industry, petroleum and the like. Industrially, furfural is mainly obtained by acid-catalyzed hydrolysis of plant fibers, and is a few biomass-based platform chemicals produced in large-scale commercialization by taking lignocellulose biomass as a raw material. Furfural can be hydrogenated to prepare various chemical raw materials and fine chemicals with high added values, so that the hydrogenation process is more and more concerned. Due to the unique molecular structure of furfural, the reaction path is complex and products are numerous in the hydrogenation process, so that the selection of a proper catalyst and a proper reaction system to obtain a target product with high selectivity is a challenge in research.
As one of the products of selective hydrogenation of furfural, tetrahydrofurfuryl alcohol (also known as tetrahydrofurfuryl alcohol) has degradability, low toxicity and strong stability, is an important organic synthetic raw material and green solvent, is also an important platform molecular compound, and has important application in agriculture, printing industry and industry.
Currently, tetrahydrofurfuryl alcohol is mainly produced industrially by a two-step process, i.e. furfural is first selectively hydrogenated to obtain furfuryl alcohol, and then furfuryl alcohol is further selectively hydrogenated to obtain tetrahydrofurfuryl alcohol. But because of higher energy consumption (1 ton tetrahydrofurfuryl alcohol production average consumption furfural 1.5-2 ton, hydrogen consumption 1000m3The reaction temperature is 170-200 ℃ and the pressure is 4.0-6.0MPa), so that the production cost is high. Furthermore, the traditional industry uses copper-chromium based catalysts for the two-step production of tetrahydrofurfuryl alcohol, as disclosed in the traditional copper-chromium systems of patents US2094975, CN1978051 and CN 1562477. In the catalytic system, the metal active component is easy to lose andcan cause serious chromium pollution and cause great harm to the environment. At present, skeleton nickel catalysts are mostly used in the industry, and can obtain higher furfural conversion rate and tetrahydrofurfuryl alcohol selectivity, for example, in patent CN1847234A, molybdenum modified skeleton nickel catalysts are adopted to catalyze furfural hydrogenation to prepare tetrahydrofurfuryl alcohol under milder conditions (1.5-2.0MPa, 30-80 ℃), and the yield is 99.5%. The patent CN1789257 uses a supported NiCoB alloy catalyst to obtain tetrahydrofurfuryl alcohol with a purity of 99% under the reaction conditions of 110 ℃ and 3 MPa. However, the skeletal nickel catalyst is unstable, easy to catch fire when exposed to air, poor in safety, complex in preparation process and limited in application to a certain extent.
In order to reduce the production cost, various catalysts for preparing tetrahydrofurfuryl alcohol by furfural through one-step hydrogenation have been developed, for example, patent CN102489315A discloses a Ru/Al catalyst2O3The catalyst can be used for preparing tetrahydrofurfuryl alcohol with the purity of 99 percent at the temperature of 80 ℃ and the hydrogen pressure of 1 MPa. Ru/TiO disclosed in patent CN109647388A2-ZnO2-ZrO2The catalyst has furfural conversion rate of over 95% and tetrahydrofurfuryl alcohol selectivity of 94% at 105 deg.c and 2MPa hydrogen pressure. Therefore, the method has the advantages that the method for preparing the tetrahydrofurfuryl alcohol by the furfural through one-step hydrogenation already obtains better results, and the preparation process of the catalyst is too complex because the catalytic active components are all noble metals although the reaction conditions are mild, so that the production cost and the separation difficulty are further improved. In order to further reduce the cost and the separation difficulty of the product, patent CN105693659 discloses a supported Ni/Al modified by alkaline earth metal (Mg, Ca, Sr, Ba)2O3The catalyst reacts for 4 hours at 140 ℃ and 4MPa, the yield of the tetrahydrofurfuryl alcohol is 98 percent, but the catalyst has poor water phase stability and is difficult to realize large-scale application.
Disclosure of Invention
The invention aims to overcome the defects of high production cost, poor stability, unstable framework nickel catalyst and the like in the prior art, and provides a method for preparing tetrahydrofurfuryl alcohol by one-step hydrogenation of furfural in a reaction system under mild conditions by using a non-noble metal catalyst. The Cu-Ni bimetallic catalyst which is prepared by directly reducing the catalyst precursor has the advantages of simple preparation process, high dispersion of double-active metal components, easy recovery and good stability, can be used for preparing tetrahydrofurfuryl alcohol under mild conditions, has the advantages of low production cost, high product yield and the like, and meets the requirement of green chemistry.
In order to achieve the above object, a first aspect of the present invention provides a Cu-Ni bimetallic catalyst comprising a carrier on which one or both of metals Cu, Ni are supported; wherein the carrier is a mixture of aluminum oxide and magnesium oxide, and the mass ratio of the metal to the carrier is 1/(1-2); the molar ratio of the double-active center Cu/Ni in the catalyst is 3/1-1/3.
The second aspect of the invention provides a preparation method of the novel Cu-Ni bimetallic catalyst, which comprises the following specific steps: dissolving four metal salts respectively containing copper, nickel, magnesium and aluminum in deionized water, dropwise adding the mixed metal salt solution and the alkali solution into an anhydrous sodium carbonate solution, controlling the pH value to be 9-13, stirring, and sequentially washing, drying and grinding the obtained precipitate to obtain a catalyst precursor; the precursor is directly reduced in a hydrogen atmosphere and then passivated in an argon-oxygen mixed gas.
The third aspect of the invention provides a method for directly preparing tetrahydrofurfuryl alcohol by furfural through one-step hydrogenation. The method is carried out in a kettle type stirrer, one of isopropanol, water or ethanol is taken as a solvent, and the mass ratio of the solvent to furfural is (0-99)/1. In the reaction, the reaction temperature is 60-150 ℃, the reaction pressure is 0.1-5MPa, and the reaction time is 0.1-15 hours.
The invention has the beneficial effects that:
(1) the novel Cu-Ni bimetallic catalyst can be used for directly hydrogenating to generate tetrahydrofurfuryl alcohol in one step, so that the intermediate step and the separation of an intermediate product are avoided, and the production cost is effectively reduced.
(2) The catalyst has the advantages of simple preparation process, good dispersion degree of active metals, higher activity and tetrahydrofurfuryl alcohol selectivity.
(3) When the catalyst is used for furfural hydrogenation, the production cost is low, the reaction condition is mild, and the green and economical reaction is realized.
Drawings
FIG. 1 is H of Cu-Ni bimetallic catalyst precursor2-TPR spectrum.
Detailed Description
The technical scheme of the invention is clearly and completely described by combining the embodiment. The described embodiments are only a part of the embodiments of the present invention, not all of them, and the present invention is not limited thereto, and any changes and variations made by those skilled in the art within the scope of the present disclosure are covered within the protection scope of the present invention.
Example 1 preparation and Performance testing of Cu/MgAlO catalyst
1) Preparation and performance test of catalyst precursor
Pouring 120ml of deionized water into a dry and clean 200ml beaker, and adding 4.8g of NaOH to completely dissolve the deionized water; 60ml of deionized water was poured into a dry, clean 120ml beaker, and 6.38g of Al (NO) was added sequentially3)3·9H2O、5.19g Cu(NO3)2·3H2O and 3.21g Mg (NO)3)2·6H2O, stirring until the mixed solution is clear; 8.5ml of deionized water was poured into a dry, clean 500ml four-necked round bottom flask, and 0.9g of anhydrous Na was added2CO3And stirring to completely dissolve the mixture. The mixed solution and the NaOH solution were slowly added dropwise to the 500ml four-necked round-bottomed flask at the same time, and the dropping rates of the two were controlled so that the dropping rates of the mixed solution and the NaOH solution were 1: 2. The pH value of the solution during the dripping process is recorded in real time by using a pH meter and is controlled between 11 and 13.
After the dropwise addition is finished, the obtained suspension is quickly transferred into an oil bath kettle at the temperature of 60 ℃, and is stirred and crystallized for 12 hours; washing precipitates in the crystallized suspension by using deionized water until the pH value of the washing liquid is approximately equal to 7; and drying the washed precipitate at 80 ℃ for 20 hours, grinding the obtained solid, and screening the ground solid by using a 100-mesh screen to obtain a catalyst precursor, which is recorded as Cu/MgAl-LDH.
2) Direct reduction and passivation of the precursor
And (2) reducing the Cu/MgAl-LDH precursor in a tube furnace by using hydrogen under the reduction conditions: heating to 450 ℃ at the temperature rise rate of 5 ℃/min under normal pressure and in the hydrogen atmosphere with the volume flow rate of 40ml/min, and keeping for 3 hours; and after the reduction is finished and the temperature is reduced to the room temperature, switching the gas circuit to argon gas with the volume flow rate of 40ml/min, purging for 1 hour, introducing oxygen with the volume flow rate of 10ml/min for passivation, and marking the passivation time as Cu/MgAlO after 3 hours.
3) Test for catalytic Performance
(1) The Cu/MgAlO catalyst prepared in this example needs to be reduced before hydrogenation reaction, and the reduction conditions are as follows: under normal pressure, in a hydrogen-argon mixed atmosphere with a volume flow rate of 80ml/min (the volume flow rate ratio of hydrogen to argon is 1:1), the mixture was heated to 400 ℃ at a temperature rise rate of 5 ℃/min and held for 2 hours.
(2) In this example, the purchased furfural reactant needs to be subjected to vacuum distillation to remove the oxidative condensation products and other impurities before hydrogenation reaction.
(3) Adding 20ml of isopropanol, 0.48g of furfural subjected to reduced pressure distillation in the step (2), 0.19g of 1, 2-propylene glycol (internal standard substance) and 50mg of Cu/MgAlO catalyst subjected to reduction in the step (1) into a 50ml stainless steel high-pressure reaction kettle, closing the reaction kettle, replacing air in the kettle for 3 times by using hydrogen, and starting timing after heating and raising the temperature to a target temperature. The hydrogenation reaction of furfural is carried out at the temperature of 100 ℃ and 150 ℃ and the H pressure of 3MPa2800rpm for 0 to 6 hours. The reaction results are shown in table 1.
Example 2Cu3Ni1Preparation and performance test of/MgAlO catalyst
1) Preparation of catalyst precursor
Preparation of catalyst precursor was substantially the same as in example 1 except that "5.19 g of Cu (NO) in example 1 was used3)2·3H2O and 3.21g Mg (NO)3)2·6H2O' changed to 3.62g Cu (NO)3)2·3H2O、3.59g Mg(NO3)2·6H2O and 1.45g Ni(NO3)2·6H2O' and is denoted as Cu3Ni1/MgAl-LDH。
2) Direct reduction and passivation of the precursor
The precursor was directly reduced and passivated as in example 1, and the resulting catalyst was noted as Cu3Ni1/MgAlO。
3) Test for catalytic Performance
Cu prepared by the above method3Ni1The specific operation steps and reaction conditions of the MgAlO catalyst for catalyzing furfural hydrogenation to prepare tetrahydrofurfuryl alcohol are the same as those in the example 1. The reaction results are shown in table 1.
Example 3Cu1Ni1Preparation and performance test of/MgAlO catalyst
1) Preparation of catalyst precursor
Preparation of catalyst precursor was substantially the same as in example 1 except that "5.19 g of Cu (NO) in example 1 was used3)2·3H2O and 3.21g Mg (NO)3)2·6H2O 'changed to' 2.42g Cu (NO)3)2·3H2O、3.59g Mg(NO3)2·6H2O and 2.91g Ni (NO)3)2·6H2O' and is denoted as Cu1Ni1/MgAl-LDH。
2) Direct reduction and passivation of the precursor
The precursor was directly reduced and passivated as in example 1, and the resulting catalyst was noted as Cu1Ni1/MgAlO。
3) Test for catalytic Performance
Cu prepared by the above method1Ni1The specific operation steps and reaction conditions of the MgAlO catalyst for catalyzing furfural hydrogenation to prepare tetrahydrofurfuryl alcohol are the same as those in the example 1. The reaction results are shown in table 1.
Example 4Cu1Ni3Preparation and performance test of/MgAlO catalyst
1) Preparation of catalyst precursor
Preparation of catalyst precursor was substantially the same as in example 1 except that "5.19 g of Cu (NO) in example 1 was used3)2·3H2O and 3.21g Mg (NO)3)2·6H2O "changed to" 1.38g Cu (NO)3)2·3H2O、2.87g Mg(NO3)2·6H2O and 4.97g Ni (NO)3)2·6H2O' and is denoted as Cu1Ni3/MgAl-LDH。
2) Direct reduction and passivation of the precursor
The precursor was directly reduced and passivated as in example 1, and the resulting catalyst was noted as Cu1Ni3/MgAlO。
3) Test for catalytic Performance
Cu prepared by the above method1Ni3The specific operation steps and reaction conditions of the MgAlO catalyst for catalyzing furfural hydrogenation to prepare tetrahydrofurfuryl alcohol are the same as those in the example 1. The reaction results are shown in table 1.
Example 5 preparation and Performance testing of Ni/MgAlO catalyst
1) Preparation of catalyst precursor
Preparation of catalyst precursor was substantially the same as in example 1 except that "5.19 g of Cu (NO) in example 1 was used3)2·3H2O and 3.21g Mg (NO)3)2·6H2Changing O "to" 2.92g Mg (NO)3)2·6H2O and 6.57g Ni (NO)3)2·6H2O' and is recorded as Ni/MgAl-LDH.
2) Direct reduction and passivation of the precursor
The precursor was directly reduced and passivated as in example 1 and the resulting catalyst was designated as Ni/MgAlO.
3) Test for catalytic Performance
The specific operation steps and reaction conditions for preparing tetrahydrofurfuryl alcohol by catalyzing furfural hydrogenation by using the prepared Ni/MgAlO catalyst are the same as those in the example 1. The reaction results are shown in table 1.
Comparative example 1 preparation and Performance test of MgAlO catalyst
1) Preparation of catalyst precursor
Preparation of catalyst precursor was essentially the same as in example 1, except that"5.19 g of Cu (NO) in example 13)2·3H2O and 3.21g Mg (NO)3)2·6H2Changing O "to" 8.72g Mg (NO)3)2·6H2O' and is recorded as MgAl-LDH.
2) Direct reduction and passivation of the precursor
The precursor was directly reduced and passivated as in example 1 and the resulting catalyst was designated as MgAlO.
3) Test for catalytic Performance
The MgAlO catalyst prepared by the method is used for catalyzing furfural hydrogenation to prepare tetrahydrofurfuryl alcohol, and the specific operation steps and the reaction conditions are the same as those in the example 1. The reaction results are shown in table 1.
Claims (4)
1. A Cu-Ni bimetallic catalyst for directly converting furfural into tetrahydrofurfuryl alcohol is characterized in that: the Cu-Ni bimetallic catalyst comprises a carrier and metal Cu and Ni loaded on the carrier; wherein the carrier is a mixture of aluminum oxide and magnesium oxide, and the mass ratio of the metal to the carrier is 1/(1-2); the molar ratio of the double-active center Cu/Ni in the catalyst is 3/1-1/3.
2. A preparation method of a Cu-Ni bimetallic catalyst for directly converting furfural into tetrahydrofurfuryl alcohol is characterized by comprising the following steps: dissolving four metal nitrates respectively containing copper, nickel, magnesium and aluminum in deionized water, dropwise adding the mixed metal salt solution into an anhydrous sodium carbonate solution, controlling the pH value to be 9-13, stirring, and sequentially washing, drying and grinding the obtained precipitate to obtain a catalyst precursor; and directly reducing the obtained catalyst precursor in a hydrogen atmosphere, and then passivating in an argon-oxygen mixed gas to obtain the Cu-Ni bimetallic catalyst.
3. The preparation method of claim 1, wherein the mass ratio of the active metal to the carrier in the Cu-Ni bimetallic catalyst is 1/(1-2), the molar ratio of Cu/Ni is 3/1-1/3, and the molar ratio of magnesium to aluminum is 2-4.8.
4. Use of a Cu-Ni bimetallic catalyst as claimed in claim 1, characterized in that: in the hydrogen atmosphere, the prepared Cu-Ni bimetallic catalyst is adopted, the reaction temperature is 60-150 ℃, the reaction pressure is 0.1-5MPa, the reaction time is 0.1-15 hours, and one of isopropanol, water and ethanol is taken as a solvent, so that one-step hydrogenation of furfural is realized to directly prepare tetrahydrofurfuryl alcohol.
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Cited By (3)
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| CN114591271A (en) * | 2022-03-22 | 2022-06-07 | 大连理工大学 | Method for preparing tetrahydrofurfuryl alcohol by furfural one-step hydrogenation under low-temperature condition |
| CN114713236A (en) * | 2022-03-30 | 2022-07-08 | 郑州大学 | Ni-ReOx/TiO2Bimetallic catalyst, preparation method thereof and application thereof in biomass aldehyde selective hydrogenation |
| CN115069255A (en) * | 2022-07-28 | 2022-09-20 | 齐鲁工业大学 | Nickel-based bimetallic catalytic material and preparation method and application thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114591271A (en) * | 2022-03-22 | 2022-06-07 | 大连理工大学 | Method for preparing tetrahydrofurfuryl alcohol by furfural one-step hydrogenation under low-temperature condition |
| CN114713236A (en) * | 2022-03-30 | 2022-07-08 | 郑州大学 | Ni-ReOx/TiO2Bimetallic catalyst, preparation method thereof and application thereof in biomass aldehyde selective hydrogenation |
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Application publication date: 20211029 |