A method for preparing alkyl ethers by catalyzing 5-hydroxymethylfurfural in a one-step process using dual catalysts

Abstract

The invention discloses a method for preparing an alkyl ether by catalyzing 5-hydroxymethylfurfural using a dual-catalyst synergistic one-step process. A raw material containing 5-hydroxymethylfurfural is contacted with a catalyst A and a catalyst B, and etherified by hydrogenation under a hydrogen atmosphere to obtain 2,5-furan dimethanol alkyl ether. The one-step process is prepared in the same mixed system, with catalysts A and B uniformly dispersed and non-interfering with each other, while simultaneously catalyzing the two steps of preparing the alkyl ether. The method for preparing 2,5-furan dimethanol alkyl ether adopted by the present invention has strong reaction activity, high selectivity, dual catalyst synergy, accelerated reaction process, good reusability, and is safe and pollution-free.

Description

Technical Field

[0001] The invention belongs to the technical field of chemical industry, and particularly relates to a method for preparing alkyl ether by catalyzing 5-hydroxymethylfurfural in a one-step process with dual catalysts. Background Art

[0002] The energy crisis has become an unavoidable problem in today's society. Currently, many countries around the world are experiencing shortages of energy sources such as coal, oil, and natural gas. Renewable resources such as biomass energy and solar energy can effectively solve today's energy crisis. Biomass energy is an inexpensive renewable resource with the characteristics of wide distribution, low resource cost, and environmental friendliness. It can replace fossil energy to produce chemicals and fuels, thereby reducing the greenhouse effect and environmental pollution. 2,5-furan dimethanol alkyl ether (BRMF), a derivative of 5-hydroxymethylfurfural hydroetherification, is considered a potential biodiesel additive and is expected to partially replace petroleum-based fuels. Therefore, studying the catalytic process for preparing BRMF using HMF as raw material is of great significance for the utilization of new renewable resources.

[0003] 5-Hydroxymethylfurfural (HMF), obtained from biomass-derived sugars through dehydration, contains furan rings, hydroxyl groups, and aldehyde groups. Through chemical reactions such as oxidation, hydrogenation, esterification, halogenation, and polymerization, HMF can be used to produce polymer monomers, liquid fuels, and green solvents, as well as to transform into pharmaceuticals, fuel intermediates, and other high-value chemicals. For this reason, the U.S. Department of Energy has designated HMF as one of the top ten key platform compounds for biofuels. 5-Hydroxymethylfurfural (HMF) has also been identified as a key platform compound for the synthesis of 2,5-furandicarboxylic acid (FDCA), levulinic acid (LA), furfuryl ethers, and other high-value chemicals. Among various biomass-derived liquid fuels, 2,5-dihydroxymethylfuran dialkyl ethers (BAMF) prepared from HMF or its derivative, 2,5-dihydroxymethylfuran (BHMF), exhibit excellent properties such as high energy density, high cetane number, moderate boiling point, and strong stability, making it a promising candidate for use as a novel biodiesel additive.

[0004] Currently, most methods involve first hydrogenating HMF to produce BHMF, and then etherifying BHMF to produce BAMF (a two-step process). The separation of the intermediate products inevitably results in additional costs and operational difficulties. Summary of the Invention

[0005] The purpose of this section is to summarize some aspects of the embodiments of the present invention and briefly introduce some preferred embodiments. Some simplifications or omissions may be made in this section and the abstract and title of this application to avoid obscuring the purpose of this section, the abstract and the title of the invention, and such simplifications or omissions should not be used to limit the scope of the present invention.

[0006] In view of the above problems and / or the problems existing in the prior art, the present invention is proposed.

[0007] Therefore, the purpose of the present invention is to overcome the deficiencies in the prior art and provide a method for preparing alkyl ethers by catalyzing 5-hydroxymethylfurfural in a one-step process using dual catalysts.

[0008] In order to solve the above technical problems, the present invention provides the following technical solution: a method for preparing alkyl ethers by catalyzing 5-hydroxymethylfurfural in a one-step process using dual catalysts, comprising:

[0009] Using 5-hydroxymethylfurfural as a raw material and a low-carbon alcohol as a reaction solvent, catalyst A and catalyst B are added, and the 2,5-furan dimethanol alkyl ether is prepared by catalytic hydrogenation etherification under a hydrogen pressure atmosphere;

[0010] The catalyst A is a bimetallic supported catalyst, in which two metals are supported on a carrier to efficiently catalyze the hydrogenation of 5-hydroxymethylfurfural to produce the intermediate 2,5-furan dimethanol;

[0011] The catalyst B is a silicon-aluminum molecular sieve, and the intermediate obtained by etherification in the mixed system is used to prepare 2,5-furan dimethanol alkyl ether.

[0012] As a preferred embodiment of the method of the present invention, the bimetallic supported catalyst comprises a carrier, a metal component X and a metal component Y supported on the carrier;

[0013] Wherein, the metal component X includes a transition metal element and is a hydrogenation active center;

[0014] The metal component Y includes an alkali metal element or an alkaline earth metal element, and is a modifying component.

[0015] As a preferred embodiment of the method of the present invention, the carrier comprises one or more of silicon oxide, magnesium oxide, aluminum oxide, titanium oxide, cerium oxide, zinc oxide, calcium oxide, and barium oxide;

[0016] The metal component X is selected from any one or more of Cu, Ni, Co, and Fe;

[0017] The metal component Y is selected from alkali metal elements or alkaline earth metal elements, and the alkali metal elements or alkaline earth metal elements include any one or more of Na, Mg, K, Ca, Cs, and Ba.

[0018] As a preferred embodiment of the method of the present invention, the metal component X loaded on the catalyst A is one or more of the sulfate, nitrate, acetate, phosphate, and chloride of the corresponding metal, and the metal loading amount is 0.1 wt% to 20 wt%;

[0019] The metal component Y loaded on the catalyst A is a salt compound of a corresponding alkaline metal, and the metal loading amount is 0.01 wt% to 15 wt%.

[0020] As a preferred embodiment of the method of the present invention, the catalyst A is loaded with the metal component X and the metal component Y by pressure impregnation, and the loading order is first loading the active metal component X, then drying and calcining it after loading, crushing it evenly, and then loading the modified metal component Y.

[0021] As a preferred embodiment of the method of the present invention, the pressure impregnation method has an impregnation pressure of 0.1 MPa to 2 MPa, a load temperature of 50° C. to 150° C., and a load time of 3 h to 12 h.

[0022] As a preferred embodiment of the method of the present invention, the calcination temperature is 200-800° C., and the calcination time is 1 h to 20 h.

[0023] As a preferred embodiment of the method of the present invention, the silicon-aluminum molecular sieve is Al-MCM-41 molecular sieve, and the silicon-aluminum ratio is 25:1.

[0024] As a preferred embodiment of the method of the present invention, the reaction temperature is 50-200° C., the reaction time is 0.5-10 h, the concentration of 5-hydroxymethylfurfural in the reaction solution is 0.1-3000 mM, and the hydrogen pressure is 0.1 MPa-8 MPa.

[0025] As a preferred embodiment of the method of the present invention, the reaction solvent is one of methanol, ethanol, n-propanol, isopropanol, and n-butanol, the mass ratio of catalyst A to catalyst B is 10:1 to 1:1, and the mass ratio of 5-hydroxymethylfurfural to the total mass of the two catalysts is 1:1 to 30:1.

[0026] Beneficial effects of the present invention:

[0027] (1) The method for preparing 2,5-furan dimethanol alkyl ether provided by the present invention can realize large-scale industrial production because the preparation is more economical and efficient and the raw material 5-hydroxymethylfurfural can be prepared from sufficient renewable sources (such as fructose, sucrose, glucose, straw, etc.), which is widely available and inexpensive, and conforms to the technical and economic production mode.

[0028] (2) The hydrogenation activity of the bimetallic supported catalyst prepared by the present invention is non-noble metal nanoparticles, and its alkali metal particles are modified components. The bimetallic interaction adjusts the composition of the active center, improves the dispersion of the hydrogenation active metal nanoparticles, adjusts the size, electron cloud density and crystallinity of the hydrogenation active metal nanoparticles, reduces the acidity of the catalyst, and thus improves the selectivity and reaction rate of the hydrogenation of HMF to BHMF.

[0029] (3) Compared with traditional supported catalysts, the bimetallic supported catalyst prepared by the present invention adopts the pressure impregnation method to support the supported bimetallic components, which can be better anchored on the support, not easy to fall off, not easy to deactivate, and has strong regeneration, reducing the cost of production and use. The loading method is easy to operate and can be adaptively adjusted according to actual conditions. It has strong operability, low price, simple synthesis, and is safe and reliable.

[0030] (4) The dual catalysts in the reaction of the present invention act synergistically to accelerate the forward reaction process. The bimetallic supported catalyst selectively hydrogenates HMF in the reaction system to prepare the intermediate BHMF. The silica-alumina molecular sieve then etherifies the intermediate BHMF to obtain 2,5-furan dimethanol alkyl ether. The use of a bimetallic catalyst system ensures the high selectivity of the intermediate product BHMF, thereby improving the yield of the final etherification reaction. Different from the traditional two-step separate reaction, the additional cost and operational difficulty of the intermediate product separation are reduced. Different from the novel single catalyst one-step preparation, the target is clearer and the specificity is stronger. It also avoids the large amount of by-products that are inevitably produced by the dual action of hydrogenation and etherification in a single catalyst, which affects the final yield.

[0031] (5) The reaction process for preparing 2,5-furan dimethanol alkyl ether of the present invention has a faster reaction rate, a higher conversion rate, a controllable reaction process (changing different reaction condition parameters), a very strong selectivity, avoiding the interference of various intermediate products, effectively improving the yield of the reaction, reducing the difficulty of separation, improving the yield, and being easy to implement on a large scale; the method for preparing 2,5-furan dimethanol alkyl ether provided by the present invention has a higher conversion rate, and its bio-based raw materials based on renewable sources are easy to post-process, environmentally friendly, and clean. BRIEF DESCRIPTION OF THE DRAWINGS

[0032] In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the following briefly introduces the drawings required for describing the embodiments. Obviously, the drawings described below are only some embodiments of the present invention. Those skilled in the art can also derive other drawings based on these drawings without inventive effort. Among them:

[0033] Figure 1This is a transmission electron microscope (TEM) image of the carrier Al2O3.

[0034] Figure 2 This is the TEM characterization of the bimetallic supported catalyst Cu(5%)-K(0.5%) / Al2O3 with Al2O3 as the carrier.

[0035] Figure 3 Transmission electron microscope scanning (TEM, 500nm) image of silicon-aluminum etherified molecular sieve Al-MCM-41

[0036] Figure 4 This is a transmission electron microscope scanning (TEM, 100nm) image of the silicon-aluminum etherified molecular sieve Al-MCM-41.

[0037] Figure 5 This is the XRD pattern of silicon-aluminum etherified molecular sieve Al-MCM-41.

[0038] Figure 6 This is the pore size distribution curve of the silicon-aluminum etherified molecular sieve Al-MCM-41.

[0039] Figure 7 This is the N2 adsorption and desorption isotherm of the silica-alumina etherified molecular sieve Al-MCM-41.

[0040] Figure 8 This is the NH3-TPD diagram of the silica-alumina etherified molecular sieve Al-MCM-41. DETAILED DESCRIPTION

[0041] In order to make the above-mentioned objects, features and advantages of the present invention more obvious and easy to understand, the specific implementation methods of the present invention are described in detail below in conjunction with the embodiments of the specification.

[0042] In the following description, many specific details are set forth to facilitate a full understanding of the present invention. However, the present invention may also be implemented in other ways different from those described herein. Those skilled in the art may make similar generalizations without violating the connotation of the present invention. Therefore, the present invention is not limited to the specific embodiments disclosed below.

[0043] Secondly, the term "one embodiment" or "embodiment" herein refers to a specific feature, structure, or characteristic that may be included in at least one implementation of the present invention. The phrase "in one embodiment" appearing in various places throughout this specification does not necessarily refer to the same embodiment, nor does it refer to a separate or selective embodiment that is mutually exclusive of other embodiments.

[0044] Unless otherwise specified, the experimental materials used in the following examples can be purchased from conventional biochemical reagent companies.

[0045] The analysis method in the embodiment of the present invention is as follows:

[0046] In the examples, the products of the 5-hydroxymethylfurfural synthesis reaction were analyzed using an Agilent LC1260 high performance liquid chromatograph, and the external standard method was used for quantification.

[0047] Time-of-flight mass spectrometry (TOF) was used to qualitatively analyze the products in the 5-hydroxymethylfurfural synthesis reaction.

[0048] X-ray powder diffractometer (XRD) was used to qualitatively analyze the silica-alumina molecular sieve.

[0049] The specific surface area of ​​the prepared Al2O3 supported catalyst was qualitatively and quantitatively analyzed using a specific surface area absorption analyzer (BET).

[0050] The temperature programmed chemical adsorption analyzer TPD / TPR / TPO was used to perform qualitative and quantitative analysis on the acid content of silica-alumina molecular sieves.

[0051] Transmission electron microscopy (TEM) was used to characterize the morphology of the prepared bimetallic supported catalyst and silica-alumina molecular sieve.

[0052] The calculation method in the embodiments of the present application is as follows:

[0053] The calculation formulas for catalyst selectivity, 5-hydroxymethylfurfural conversion rate and 2,5-furan dimethanol alkyl ether yield are as follows:

[0054] Yield of 2,5-furandimethanol alkyl ether = (mass of 2,5-furandimethanol alkyl ether in the product / theoretical mass of 2,5-furandimethanol alkyl ether produced) × 100%;

[0055] HMF conversion rate = (mass of 5-HMF actually involved in the reaction / mass of 5-HMF in the raw material) × 100%;

[0056] Total selectivity of dual catalysts = (yield of 2,5-furan dimethanol alkyl ether / conversion of 5-hydroxymethylfurfural) × 100%.

[0057] The carriers in the present invention are all pretreated. The pretreatment process of the carriers is as follows: under negative pressure, the carriers are placed in a vacuum drying and degassing treatment at 100°C for 6 hours for use;

[0058] Determination of saturated water absorption capacity of carrier: Take 10g of spare carrier and place it in a beaker, slowly and evenly add deionized water until 10g of carrier is saturated with adsorption and the surface of the carrier is just soaked with water; the amount of water adsorbed by the carrier at this time is the saturated water absorption capacity of the carrier.

[0059] Example 1

[0060] (1) Add 10 ml of water and 1.92 g of copper nitrate trihydrate to a beaker and dissolve thoroughly to prepare a Cu(NO3)2 solution.

[0061] 10g of Al2O3 carrier particles were slowly poured into the prepared Cu(NO3)2 solution, and the liquid and powder were mixed evenly and then allowed to stand at room temperature for 3h. The transmission electron microscope (TEM) image of the carrier Al2O3 was shown in Fig. Figure 1 .

[0062] (2) The mixture was then transferred to a high-pressure reactor, nitrogen was introduced to 1 MPa, the temperature was raised to 120°C, and the mixture was pressurized and impregnated for 3 h;

[0063] (3) After cooling, the sample was taken out and placed in an oven until completely dry. Finally, the sample was placed in a muffle furnace and calcined at 550°C for 12 hours. After cooling, the sample was taken out to obtain an oxidized metal-supported catalyst. The catalyst was then reduced in a tubular furnace at 500°C for 8 hours under a hydrogen atmosphere to obtain a Cu (5%) / Al2O3-supported catalyst with a Cu content of 5% wt, which was designated as 1#.

[0064] Example 2

[0065] (1) Add 4.5 ml of water and 1.92 g of copper nitrate trihydrate to a beaker and dissolve thoroughly to prepare a Cu(NO3)2 solution.

[0066] Slowly pour 10g of CeO2 carrier particles into the prepared Cu(NO3)2 solution, mix the liquid and powder evenly, and then let it stand at room temperature for 3h;

[0067] (2) Then transfer it to a high-pressure reactor, introduce nitrogen to 1 MPa, raise the temperature to 120°C and pressurize and immerse for 3 hours.

[0068] (3) After cooling, the sample was taken out and placed in an oven until completely dry. Finally, the sample was placed in a muffle furnace and calcined at 550°C for 12 hours. After cooling, the sample was taken out to obtain an oxidized metal-supported catalyst. The catalyst was then reduced in a tubular furnace at 500°C for 8 hours under a hydrogen atmosphere to obtain a Cu(5%) / CeO2-supported catalyst with a Cu content of 5%wt, which was recorded as 2#.

[0069] Example 3

[0070] (1) Add 12.5 ml of water and 1.92 g of copper nitrate trihydrate to a beaker and dissolve thoroughly to prepare a Cu(NO3)2 solution.

[0071] Slowly pour 10g of TiO2 carrier particles into the prepared Cu(NO3)2 solution, mix the liquid and powder evenly, and then let it stand at room temperature for 3h;

[0072] (2) Then transfer it to a high-pressure reactor, introduce nitrogen to 1 MPa, raise the temperature to 120°C and pressurize and immerse for 3 hours.

[0073] (3) After cooling, the sample was taken out and placed in an oven until completely dry. Finally, the sample was placed in a muffle furnace and calcined at 550°C for 12 hours. After cooling, the sample was taken out to obtain an oxidized metal-supported catalyst. The catalyst was then reduced in a tubular furnace at 500°C for 8 hours under a hydrogen atmosphere to obtain a Cu (5%) / TiO2-supported catalyst with a Cu content of 5% wt, which was recorded as 3#.

[0074] Example 4

[0075] (1) Add 10 ml of water and 2.478 g of nickel nitrate hexahydrate to a beaker and dissolve them thoroughly to prepare a Ni(NO3)2 solution;

[0076] Slowly pour 10g of Al2O3 carrier particles into the prepared Ni(NO3)2 solution, mix the liquid and powder evenly, and then let it stand at room temperature for 3h;

[0077] (2) Then transfer it to a high-pressure reactor, introduce nitrogen to 1 MPa, raise the temperature to 120°C and pressurize and immerse for 3 hours.

[0078] (3) After cooling, the sample was taken out and placed in an oven until completely dry. Finally, the sample was placed in a muffle furnace and calcined at 550°C for 12 hours. After cooling, the sample was taken out to obtain an oxidized metal-supported catalyst. The catalyst was then reduced in a tubular furnace at 500°C for 8 hours under a hydrogen atmosphere to obtain a Ni(5%)-Al2O3-supported catalyst. The mass content of Ni was 5% wt and was recorded as 4#.

[0079] Example 5

[0080] (1) Add 10 ml of water and 1.152 g of copper nitrate trihydrate to a beaker and dissolve thoroughly to prepare a Cu(NO3)2 solution.

[0081] Slowly pour 10g of Al2O3 carrier particles into the prepared Cu(NO3)2 solution, mix the liquid and powder evenly, and then let it stand at room temperature for 3h;

[0082] (2) Then transfer it to a high-pressure reactor, introduce nitrogen to 1 MPa, raise the temperature to 120°C and pressurize and immerse for 3 hours.

[0083] (3) After cooling, the sample was taken out and placed in an oven until completely dry. Finally, the sample was placed in a muffle furnace and calcined at 550°C for 12 hours. After cooling, the sample was taken out to obtain an oxidized metal-supported catalyst. The catalyst was then reduced in a tubular furnace at 500°C for 8 hours under a hydrogen atmosphere to obtain a Cu (3%) / Al2O3-supported catalyst with a Cu content of 3% wt, which was designated as 5#.

[0084] Example 6

[0085] (1) Add 10 ml of water and 2.688 g of copper nitrate trihydrate to a beaker and dissolve thoroughly to prepare a Cu(NO3)2 solution.

[0086] Slowly pour 10g of Al2O3 carrier particles into the prepared Cu(NO3)2 solution, mix the liquid and powder evenly, and then let it stand at room temperature for 3h;

[0087] (2) Then transfer it to a high-pressure reactor, introduce nitrogen to 1 MPa, raise the temperature to 120°C and pressurize and immerse for 3 hours.

[0088] (3) After cooling, the sample was taken out and placed in an oven until completely dry. Finally, the sample was placed in a muffle furnace and calcined at 550°C for 12 hours. After cooling, the sample was taken out to obtain an oxidized metal-supported catalyst. The catalyst was then reduced in a tubular furnace at 500°C for 8 hours under a hydrogen atmosphere to obtain a Cu (7%) / Al2O3-supported catalyst with a Cu content of 7% wt, which was designated as 6#.

[0089] Example 7

[0090] (1) Add 10 ml of water and 1.92 g of copper nitrate trihydrate to a beaker and dissolve thoroughly to prepare a Cu(NO3)2 solution.

[0091] Using the equal volume impregnation method, 10g of Al2O3 carrier particles were slowly poured into the prepared Cu(NO3)2 solution. After the liquid and powder were evenly mixed, the mixture was allowed to stand at room temperature for 3h. The mixture was then transferred to a high-pressure reactor, nitrogen was introduced to 1MPa, and the temperature was raised to 120℃ for pressure impregnation for 3h.

[0092] After cooling, the sample was placed in an oven until completely dry, and finally the sample was taken out and placed in a muffle furnace for calcination at 550° C. for 12 h. After cooling, the oxidized Cu (5%) / Al 2 O 3 supported catalyst was taken out and crushed for preparation.

[0093] (2) Add 10 ml of water and 0.129 g of potassium nitrate to the beaker and dissolve them thoroughly to prepare a KNO3 solution;

[0094] Slowly pour the crushed catalyst into the prepared KNO3 solution, mix the liquid and powder evenly, let it stand at room temperature for 3 hours, then transfer it to a high-pressure reactor, introduce nitrogen to 1MPa, heat to 120℃ and impregnate under pressure for 3 hours.

[0095] (3) After cooling, the sample was taken out and placed in an oven until completely dry. Finally, the sample was placed in a muffle furnace and calcined at 350°C for 10 hours. After cooling, the sample was taken out to obtain an oxidized bimetallic supported catalyst. The sample was then reduced in a tubular furnace at 300°C for 6 hours under a hydrogen atmosphere to obtain a Cu(5%)-K(0.5%) / Al2O3 bimetallic supported catalyst. The mass content of Cu was 5%wt and the mass content of K was 0.5%wt. It was recorded as 7#. The oxidation state of sample 7# was scanned by TEM electron microscope. The results showed that Figure 2 As shown in the figure, it can be seen that the bimetallic is evenly dispersed on the carrier Al2O3.

[0096] Example 8

[0097] (1) Add 10 ml of water and 1.92 g of copper nitrate trihydrate into a beaker and fully dissolve to prepare a Cu(NO3)2 solution; slowly pour 10 g of Al2O3 carrier particles into the prepared Cu(NO3)2 solution to mix the liquid and powder evenly, then let it stand at room temperature for 3 hours, then transfer it to a high-pressure reactor, introduce nitrogen to 1 MPa, heat to 120°C and pressurize for 3 hours;

[0098] After cooling, the sample was taken out and placed in an oven until completely dry. Finally, the sample was placed in a muffle furnace and calcined at 550° C. for 12 h. After cooling, the oxidized Cu (5%) / Al 2 O 3 supported catalyst was taken out and crushed for preparation.

[0099] (2) Add 10 ml of water and 0.185 g of sodium nitrate to the beaker and dissolve them fully to prepare a NaNO3 solution. Slowly pour the crushed catalyst into the prepared NaNO3 solution to mix the liquid and powder evenly. Let it stand at room temperature for 3 hours, then transfer it to a high-pressure reactor, introduce nitrogen to 1 MPa, heat to 120°C and impregnate under pressure for 3 hours.

[0100] (3) After cooling, the sample was removed and placed in an oven until completely dry. Finally, the sample was placed in a muffle furnace and calcined at 350°C for 10 h. After cooling, the sample was removed to obtain an oxidized bimetallic supported catalyst. The catalyst was then reduced in a tubular furnace at 300°C for 6 h under a hydrogen atmosphere to obtain a Cu(5%)-Na(0.5%) / Al2O3 bimetallic supported catalyst. The Cu content was 5% by weight, and the Na content was 0.5% by weight, designated as 8#.

[0101] Example 9

[0102] (1) Add 10 ml of water and 1.92 g of copper nitrate trihydrate into a beaker and dissolve them fully to prepare a Cu(NO3)2 solution; slowly pour 10 g of Al2O3 carrier particles into the prepared Cu(NO3)2 solution, mix the liquid and powder evenly, and let it stand at room temperature for 3 hours, then transfer it to a high-pressure reactor, introduce nitrogen to 1 MPa, heat to 120°C and impregnate under pressure for 3 hours; after cooling, place the sample in an oven until it is completely dry, and finally take out the sample and place it in a muffle furnace for calcination at 550°C for 12 hours. After cooling, take out the sample to obtain the oxidized Cu(5%) / Al2O3 supported catalyst, and crush it for preparation.

[0103] (2) Add 10 ml of water and 0.073 g of cesium nitrate to the beaker and dissolve them fully to prepare a CsNO3 solution. Slowly pour the crushed catalyst into the prepared CsNO3 solution to mix the liquid and powder evenly. Let it stand at room temperature for 3 hours, then transfer it to a high-pressure reactor, introduce nitrogen to 1 MPa, heat to 120°C and impregnate under pressure for 3 hours.

[0104] (3) After cooling, the sample was removed and placed in an oven until completely dry. Finally, the sample was placed in a muffle furnace and calcined at 350°C for 10 h. After cooling, the sample was removed to obtain an oxidized bimetallic supported catalyst. The catalyst was then reduced in a tube furnace at 300°C for 6 h under a hydrogen atmosphere to obtain a Cu(5%)-Cs(0.5%) / Al2O3 bimetallic supported catalyst. The Cu content was 5% by weight, and the Cs content was 0.5% by weight, designated as 9#.

[0105] Example 10

[0106] Compared with Example 7, this example adopts the same loading method, but changes the loading amount in the secondary loading stage of alkali metal particles:

[0107] The 0.129 g of potassium nitrate in step (2) of Example 7 was replaced with 0.077 g of potassium nitrate. Other conditions were the same as in Example 7 to prepare a Cu(5%)-K(0.3%) / Al2O3 bimetallic supported catalyst. The Cu content was 5% by weight, and the K content was 0.3% by weight. This catalyst was designated as 10#.

[0108] Example 11

[0109] Example 11 is compared with Example 7, using the same loading method, but changing the loading amount in the secondary loading stage of alkali metal particles:

[0110] The 0.129 g of potassium nitrate in step (2) of Example 7 was replaced with 0.026 g of potassium nitrate. Other conditions were the same as in Example 7 to prepare a Cu(5%)-K(0.1%) / Al2O3 bimetallic supported catalyst. The Cu content was 5% by weight and the K content was 0.1% by weight. This catalyst was designated as 11#.

[0111] Example 12

[0112] Example 12 is compared with Example 7, using the same loading method, but changing the loading amount in the secondary loading stage of alkali metal particles:

[0113] In step (2) of Example 7, 0.129 g of potassium nitrate was replaced with 0.258 g. Other conditions were the same as in Example 7 to prepare a Cu(5%)-K(1%) / Al2O3 bimetallic supported catalyst. The Cu content was 5% by weight, and the K content was 1% by weight. This catalyst was designated as 12#.

[0114] Example 13

[0115] Example 13 is compared with Example 7, using the same loading method, but changing the loading amount in the secondary loading stage of alkali metal particles:

[0116] A Cu(5%)-K(2%) / Al2O3 bimetallic supported catalyst was prepared by replacing 0.129g of potassium nitrate in step (2) of Example 7 with 0.516g of potassium nitrate. Other conditions were the same as in Example 7. The Cu content was 5% by weight and the K content was 2% by weight. The catalyst was designated as 13#.

[0117] Example 14

[0118] Example 14 is compared with Example 7, using the same loading method, but changing the calcination temperature after loading the bimetallic element:

[0119] The calcination temperature at 700°C for 10 h in step (3) of Example 7 was changed from 350°C for 10 h. Other conditions remained the same as in Example 7, yielding a Cu(5%)-K(0.5%) / Al2O3 bimetallic supported catalyst. The Cu content was 5% by weight, and the K content was 0.5% by weight. The catalyst was designated #14.

[0120] Example 15

[0121] Example 14 is compared with Example 7, using the same loading method, but changing the reduction temperature after loading the bimetallic element:

[0122] The reduction at 300°C for 6 h in step (3) of Example 7 was modified to reduction at 650°C for 6 h. Other conditions were the same as in Example 7 to prepare a Cu(5%)-K(0.5%) / Al2O3 bimetallic supported catalyst. The Cu content was 5% by weight and the K content was 0.5% by weight, and the catalyst was designated as 15#.

[0123] Example 16

[0124] Example 14 is compared with Example 7, using the same loading method, but shortening the roasting time after loading the bimetallic element:

[0125] The calcination at 350°C for 10 h in step (3) of Example 7 was modified to calcination at 350°C for 2 h. Other conditions remained the same as in Example 7, yielding a Cu(5%)-K(0.5%) / Al2O3 bimetallic supported catalyst. The Cu content was 5% by weight, and the K content was 0.5% by weight. The catalyst was designated #16.

[0126] Example 17

[0127] Example 17 is compared with Example 7, using the same loading method, but changing the reduction time after loading the bimetallic element, thereby shortening the reduction time:

[0128] The reduction at 300°C for 6 h in step (3) of Example 7 was modified to a reduction at 300°C for 2 h. Other conditions were the same as in Example 7, to produce a Cu(5%)-K(0.5%) / Al2O3 bimetallic supported catalyst. The Cu content was 5% by weight, and the K content was 0.5% by weight. This catalyst was designated #17.

[0129] Example 18

[0130] The hydrogenation catalyst used in this example is a single metal supported catalyst, which is synergistically used with the etherification dual catalyst of the silica-alumina molecular sieve to synthesize 2,5-furan dimethanol diisopropyl ether (BPMF) in a one-step process in an isopropanol solvent system:

[0131] (1) Add 35 ml of isopropanol and 2.0 g of HMF to the inner liner and stir thoroughly to ensure that the raw materials are evenly dispersed and stably distributed in the reaction system. At this point, the concentration of HMF in the solution system is 454 mM. Take a sample as the initial reaction concentration;

[0132] (2) Then, 0.3 g of the prepared catalyst No. 1 Cu (5%) / Al2O3 and 0.5 g of the prepared silicon-aluminum molecular sieve Al-MCM-41 were added. The transmission electron microscopy of the silicon-aluminum etherified molecular sieve Al-MCM-41 is shown in FIG. Figure 3 and Figure 4As can be seen from the figure, the hexagonal phase of Al-MCM-41 molecular sieve can be observed. It presents directional channels and contains an interconnected internal hexagonal structure. The XRD pattern of silicon-aluminum etherified molecular sieve Al-MCM-41 can be found in Figure 5 As can be seen from the figure, Al-MCM-41 molecular sieve has an obvious characteristic diffraction broad peak at 2θ=22.60°, which is a typical feature of the amorphous nature of silicon materials;

[0133] The pore size distribution curve of silicon-aluminum etherified molecular sieve Al-MCM-41 can be found in Figure 6 The N2 adsorption and desorption isotherms of Al-MCM-41 etherified molecular sieves can be found in Figure 7 ,Depend on Figure 6 and Figure 7 It can be seen that the mesopore diameters of Al-MCM-41 and MCM-22 molecular sieves are 0.67 cm3·g-1 and 0.29 cm3·g-1, respectively. Both show type IV hysteresis loop isotherms. The adsorption capacity suddenly increases at very low P / Po, which is a typical feature of zeolites. When the relative pressure is higher than 0.92, the sharp increase in N2 absorption is associated with a small hysteresis loop, which indicates that N2 condenses in the interstitial voids generated by the molecular sieve particles, which is a typical feature of mesoporous materials. For the NH3-TPD diagram of the silica-alumina etherified molecular sieve Al-MCM-41, see Figure 8 As can be seen from the figure, there are three peaks in the spectrum, namely high temperature, medium temperature and low temperature, which are attributed to the desorption of NH3 molecules adsorbed on strong acid, medium strong acid and weak acid sites respectively.

[0134] At the same time, the substrate HMF and dual catalysts were transferred to the hydrogenation reactor at a total mass ratio of 5:2. After three nitrogen replacements, hydrogen was introduced to 1.5 MPa. The speed was adjusted to 800 rpm and a temperature program was started, with the reaction temperature at 80°C and the reaction time at 2 hours.

[0135] (3) After the reaction was completed, the mixture was cooled to room temperature and the contents in the reaction solution were analyzed by LC. The results are shown in Table 1.

[0136] Example 19

[0137] Compared with Example 18, Example 19 uses a single metal supported hydrogenation catalyst with a different supported carrier: Catalyst 2# is selected in step (2), and all other conditions are changed.

[0138] Example 20

[0139] Compared with Example 18, this example changes the loaded carrier: 3# catalyst is selected in step (2), and the other conditions are changed.

[0140] Example 21

[0141] Compared with Example 18, this example changes the loaded carrier: 4# catalyst is selected in step (2), and the other conditions are changed.

[0142] Example 22

[0143] Compared with Example 18, this example changes the loaded carrier: 5# catalyst is selected in step (2), and the other conditions are changed.

[0144] Example 23

[0145] Compared with Example 18, this example changes the loaded carrier: 6# catalyst is selected in step (2), and the other conditions are changed.

[0146] Example 24

[0147] Compared with Example 18, this example changes the loaded carrier: 7# catalyst is selected in step (2), and the other conditions are changed.

[0148] Example 25

[0149] Compared with Example 18, this example changes the loaded carrier: 8# catalyst is selected in step (2), and the other conditions are changed.

[0150] Example 26

[0151] Compared with Example 18, this example changes the loaded carrier: 9# catalyst is selected in step (2), and the other conditions are changed.

[0152] Example 27

[0153] Compared with Example 18, this example changes the loaded carrier: 10# catalyst is selected in step (2), and the other conditions are changed.

[0154] Example 28

[0155] Compared with Example 18, this example changes the loaded carrier: 11# catalyst is selected in step (2), and the other conditions are changed.

[0156] Example 29

[0157] Compared with Example 18, this example changes the loaded carrier: 12# catalyst is selected in step (2), and the other conditions are changed.

[0158] Example 30

[0159] Compared with Example 18, this example changes the loaded carrier: 13# catalyst is selected in step (2), and the other conditions are changed.

[0160] Table 1 Reaction results of Examples 18-30

[0161]

[0162]

[0163] From the reaction data of Examples 18-30 in Table 1, it can be seen that when the reaction conditions remain unchanged and the catalysts used for etherification are all silica-alumina molecular sieves, the single metal hydrogenation catalyst with Al2O3 as the carrier loaded with Cu has the best effect. At the same time, the most preferred Cu loading amount is 5%. As the loading amount decreases, the reaction effect decreases significantly, and as the loading amount increases, the reaction effect does not increase significantly, which is not in line with economic benefits.

[0164] The effect of bimetallic loaded catalyst is significantly better than that of monometallic loaded catalyst, and the effect of loaded alkali metal K is the best. At the same time, the loading amount of alkali metal is most preferably 0.5%. As the loading amount decreases, the reaction effect decreases significantly. As the loading amount increases, the reaction effect does not increase significantly, and it is not in line with economic benefits.

[0165] Example 31

[0166] Compared with Example 18, this example changes the loaded carrier: 14# catalyst is selected in step (2), and the other conditions are changed.

[0167] Table 2 Reaction results of Example 31

[0168] Example BPMF yield HMF conversion Total selectivity of dual catalysts 31 57 63 90

[0169] Compared with Example 24, the catalyst sample used in Example 31 was changed from 7# to 14#, that is, in the process of preparing the bimetallic supported catalyst, the calcination temperature was changed from 550°C to 700°C, and the other preparation conditions were unchanged. The final HMF conversion rate and BHMF yield decreased significantly. It can be seen that excessively high calcination temperature will cause the bimetallic particles loaded on the carrier to react with each other, agglomerate, and reduce the dispersion, thereby affecting the hydrogenation performance and HMF conversion in the final catalytic reaction, and further affecting the BPMF yield.

[0170] Example 32

[0171] Compared with Example 18, this example changes the loaded carrier: 15# catalyst is selected in step (2), and the other conditions are changed.

[0172] Table 3 Reaction results of Example 32

[0173] Example BPMF yield HMF conversion Total selectivity of dual catalysts 32 64 69 93

[0174] During the preparation of the bimetallic supported catalyst, the reduction temperature was changed from 300°C to 650°C, while the other preparation conditions remained unchanged. The final HMF conversion rate and BHMF yield decreased significantly. This shows that excessively high reduction temperature will cause the bimetallic particles loaded on the carrier to react with each other and agglomerate, thereby affecting the hydrogenation performance and HMF conversion in the final catalytic reaction, and further affecting the BPMF yield.

[0175] Example 33

[0176] Compared with Example 18, this example changes the loaded carrier: 16# catalyst is selected in step (2), and the other conditions are changed.

[0177] Table 4 Reaction results of Example 33

[0178] Example BPMF yield HMF conversion Total selectivity of dual catalysts 33 79 87 91

[0179] During the preparation of the bimetallic supported catalyst, the calcination time was changed from 10 h to 2 h, and the other preparation conditions remained unchanged. The final HMF conversion rate and BHMF yield decreased significantly. This shows that the insufficient calcination time resulted in unclear interaction between the bimetallic particles, thereby affecting the hydrogenation performance and HMF conversion in the final catalytic reaction. Compared with the single metal catalytic reaction, there was no significant improvement.

[0180] Example 34

[0181] Compared with Example 18, this example changes the loaded carrier: 17# catalyst is selected in step (2), and the other conditions are changed.

[0182] Table 5 Reaction results of Example 34

[0183] Example BPMF yield HMF conversion Total selectivity of dual catalysts 34 63 75 84

[0184] During the preparation of the bimetallic supported catalyst, the reduction time was changed from 6 h to 2 h, and the other preparation conditions remained unchanged. The final HMF conversion rate and BHMF yield decreased significantly. This shows that the insufficient reduction time resulted in weak interaction between the bimetallic particles after they were converted to the reduced state, thereby affecting the hydrogenation performance and HMF conversion in the final catalytic reaction, and further affecting the BPMF yield.

[0185] Example 35

[0186] Example 35 Compared with Example 24, the mass of HMF in the raw materials used in this example was changed, while the other conditions remained unchanged. The difference was that the HMF in step (1) was changed to 4.0 g. The results are shown in Table 6.

[0187] Table 6 Reaction results of Example 35

[0188] Example BPMF yield HMF conversion Total selectivity of dual catalysts 35 73 83 89

[0189] It can be seen that as the mass of HMF in the raw material increases, the concentration of HMF in the reaction solution increases, and the final BPMF yield decreases. This shows that continuously increasing the concentration of the raw material in the system does not necessarily increase the BPMF yield. Excessive raw material causes the reaction system to be densely distributed, inhibiting the activity of the catalyst, resulting in a decrease in yield and a decline in catalyst selectivity.

[0190] Example 36

[0191] Compared with Example 24, the mass of HMF in the raw materials used in Example 36 was changed, and the other conditions remained unchanged. The difference was that: HMF in step (1) was changed to 1.0 g.

[0192] Table 7 Reaction results of Example 36

[0193] Example BPMF yield HMF conversion Total selectivity of dual catalysts 36 92 100 93

[0194] As the mass of HMF in the feedstock decreases, the HMF concentration in the reaction solution decreases, and the final BPMF yield increases. This suggests that reducing the feedstock concentration while maintaining the catalyst mass effectively reduces the feedstock HMF-to-catalyst ratio, increasing BPMF yield. The extremely small amount of feedstock results in an extremely dispersed reaction system, which in turn effectively reduces the feedstock HMF-to-catalyst ratio, resulting in more complete contact between the catalyst and feedstock, leading to increased yield and enhanced catalyst selectivity. However, since the bimetallic catalytic hydrogenation performance has already reached its maximum, the effect of increasing BPMF yield is solely attributable to the etherified molecular sieve Al-MCM-41. Therefore, an excessive amount of bimetallic catalyst under these conditions is not economically efficient. Therefore, an appropriate feedstock HMF concentration and an optimal catalyst ratio are optimal for experimental efficiency.

[0195] Example 37

[0196] Compared with Example 24, Example 37 of this example has a change in the final constant reaction temperature, while the other conditions remain unchanged: the reaction temperature in step (2) is adjusted to 60°C and the reaction time is 2h.

[0197] Table 8 Reaction results of Example 37

[0198] Example BPMF yield HMF conversion Total selectivity of dual catalysts 37 63 87 72

[0199] As the final constant reaction temperature decreases, HMF conversion is incomplete, the catalyst selectivity is also weak, and the final BPMF yield decreases. This shows that decreasing temperature leads to a decrease in catalyst activity, affecting HMF conversion and selectivity, and ultimately reducing BPMF yield. This demonstrates that an appropriate temperature increases catalyst activity, accelerates HMF conversion, and ultimately improves BPMF yield.

[0200] Example 38

[0201] Compared with Example 24, Example 38 has the following characteristics: the final constant reaction temperature of this example has changed, and the other conditions have not changed: the reaction temperature of step (2) is adjusted to 110°C, and the reaction time is 2h.

[0202] Table 9 Reaction results of Example 38

[0203] Example BPMF yield HMF conversion Total selectivity of dual catalysts 38 87 100 87

[0204] As the final constant reaction temperature increases, HMF is essentially completely converted, but the final BPMF yield actually decreases. This suggests that HMF conversion accelerates with increasing temperature before the final constant temperature is reached. However, due to the high heat, some of the raw HMF is undirectedly directed toward both the product BPMF and polymerization. Simultaneously, the instability of the intermediate yield, BHMF, also occurs due to excessively high temperatures, which promotes side reactions such as polymerization. This results in a decrease in catalyst selectivity and BPMF yield. This demonstrates that maintaining the stability of the raw HMF and product BPMF at an appropriate temperature, while ensuring catalyst selectivity, is key to improving BPMF yield.

[0205] Example 39

[0206] Compared with Example 24, Example 39 is different in that the hydrogenation catalyst used in this example is changed, and the amount of the bimetallic hydrogenation catalyst is increased: in step (2), 0.5 g of the prepared 7# catalyst is added instead, and other conditions remain unchanged.

[0207] Table 10 Reaction results of Example 39

[0208] Example BPMF yield HMF conversion Total selectivity of dual catalysts 39 91 100 91

[0209] In this example, the hydrogenation catalyst used was changed by increasing the amount of bimetallic hydrogenation catalyst, resulting in a change in the ratio of substrate to bicatalyst. All other conditions remained unchanged. The increased amount of hydrogenation catalyst resulted in more complete contact between the catalyst and the feedstock. While HMF conversion had already reached an optimal level, the increased amount of hydrogenation catalyst accelerated the conversion of HMF to the intermediate BHMF, improving selectivity and preventing the intermediate BHMF from converting to other byproducts over time due to its inherent instability. This, in turn, increased the BPMF yield during the etherification process. Furthermore, because the addition of an excess amount of hydrogenation catalyst did not significantly increase the final BPMF yield, selecting an appropriate bicatalyst ratio was crucial for improving experimental and pilot-scale efficiency and economic efficiency.

[0210] Example 40

[0211] Compared with Example 24, the hydrogenation catalyst used in Example 40 was changed, and the amount of the bimetallic hydrogenation catalyst was increased: 0.1 g of the prepared 7# catalyst was added in step (2), and other conditions remained unchanged.

[0212] Table 11 Reaction results of Example 40

[0213] Example BPMF yield HMF conversion Total selectivity of dual catalysts 40 67 71 94

[0214] In this example, the hydrogenation catalyst used was changed, reducing the amount of bimetallic hydrogenation catalyst, resulting in a change in the ratio of substrate to bimetallic catalyst. All other conditions remained unchanged. However, with the reduction in the amount of hydrogenation catalyst used, the catalyst content in the same system was significantly reduced, resulting in low conversion efficiency of HMF to the intermediate BHMF, ultimately affecting etherification efficiency and causing a serious shortage of BPMF yield. This demonstrates that an appropriate catalyst content is essential for the reaction to proceed.

[0215] Example 41

[0216] Compared with Example 24, Example 41 differs in that the etherification catalyst used in this example is changed: 0.8 g of the prepared silicon-aluminum molecular sieve Al-MCM-41 is added in step (2), and other conditions remain unchanged.

[0217] Table 12 Reaction results of Example 41

[0218] Example BPMF yield HMF conversion Total selectivity of dual catalysts 41 93 100 93

[0219] Increasing the amount of etherification catalyst changes the ratio of substrate to dual catalyst, while other conditions remain unchanged. This results in more complete contact between the catalyst and feedstock, allowing efficient etherification to proceed simultaneously with the hydrogenation of HMF to the intermediate BHMF. Increasing the amount of etherification catalyst accelerates the etherification of the intermediate BHMF, improving selectivity and preventing the intermediate BHMF from converting to other byproducts over time due to its inherent instability, which increases the BPMF yield during the etherification process. Therefore, selecting the appropriate dual catalyst ratio is key to improving experimental and pilot-scale efficiency and economic efficiency.

[0220] Example 42

[0221] Compared with Example 24, Example 42 differs in that the etherification catalyst used in this example is changed: 0.2 g of prepared silicon-aluminum molecular sieve Al-MCM-41 is added in step (2), and other conditions remain unchanged.

[0222] Table 13 Reaction results of Example 42

[0223] Example BPMF yield HMF conversion Total selectivity of dual catalysts 42 70 100 70

[0224] Reducing the amount of etherification catalyst changes the ratio of substrate to dual catalyst, while keeping all other conditions unchanged. While the amount of etherification catalyst used decreases, the amount of hydrogenation catalyst remains unchanged, resulting in a 100% HMF conversion. However, the etherification catalyst content in the same system is significantly reduced, leading to a low conversion efficiency of the intermediate BHMF to the final product BPMF. This ultimately affects the etherification efficiency and results in a severely insufficient BPMF yield. This demonstrates that an appropriate catalyst content is essential to support the reaction.

[0225] Example 43

[0226] Compared with Example 24, the reaction time of Example 43 was changed, while the other conditions remained unchanged: the reaction time in step (2) was changed to 6 h.

[0227] Table 14 Reaction results of Example 43

[0228] Example BPMF yield HMF conversion Total selectivity of dual catalysts 43 87 100 87

[0229] As the reaction time increases, HMF is completely converted, but the yield of BPMF decreases. This suggests that HMF is completely converted to BHMF, but as time goes on and under high temperature conditions, the reaction begins to shift from BPMF to other reactions, leading to a decrease in BPMF yield. Therefore, an appropriate reaction time is essential to ensure efficient HMF conversion and high BPMF yield.

[0230] Example 44

[0231] Example Compared with Example 24, the solvent in step (1) of this example was replaced with ethanol, and the other conditions remained unchanged.

[0232] Table 15 Reaction results of Example 44

[0233] Example BEMF yield HMF conversion Total selectivity of dual catalysts 45 81 100 81

[0234] The dual-catalyst system of the present invention can be used to etherify HMF in various alcohol solvents, such as ethanol, to produce 2,5-furan dimethanol diethyl ether. This yields highly effective results, and excellent experimental results can be achieved simply by selecting appropriate reaction conditions.

[0235] Example 45

[0236] Example Compared with Example 24, the solvent in step (1) of this example is replaced by methanol, and the other conditions remain unchanged.

[0237] Table 16 Reaction results of Example 45

[0238] Example BMMF yield HMF conversion Total selectivity of dual catalysts 46 85 100 85

[0239] As can be seen, the dual-catalyst system of the present invention is highly effective in the etherification of HMF in various alcohol solvents, such as methanol, to produce 2,5-furan dimethanol dimethyl ether. This yields excellent experimental results, as demonstrated by simply selecting appropriate reaction conditions.

[0240] Example 46

[0241] Example Compared with Example 24, the silicon-alumina molecular sieve Al-MCM-41 in step (2) of this example is replaced by silicon-alumina molecular sieve β25, and the other conditions are unchanged.

[0242] Table 17 Reaction results of Example 46

[0243] Example BPMF yield HMF conversion Total selectivity of dual catalysts 47 46 88 52

[0244] Example 47

[0245] Example Compared with Example 24, the silicon-aluminum molecular sieve Al-MCM-41 in step (2) of this example is replaced by silicon-aluminum molecular sieve MCM-22, and the other conditions remain unchanged.

[0246] Table 18 Reaction results of Example 47

[0247] Example BPMF yield HMF conversion Total selectivity of dual catalysts 48 33 96 34

[0248] Example 48

[0249] Example Compared with Example 24, the silicon-aluminum molecular sieve Al-MCM-41 in step (2) of this example is replaced by silicon-aluminum molecular sieve ZSM-5, and the other conditions are unchanged.

[0250] Table 19 Reaction results of Example 48

[0251] Example BPMF yield HMF conversion Total selectivity of dual catalysts 49 78 100 78

[0252] It can be seen from the experimental data of Example 46, Example 47 and Example 48 that the etherification yields of other silica-alumina molecular sieves β25, MCM-22 and ZSM-5 in the one-step etherification reaction process do not reach the etherification effect of the etherification catalyst used in the present invention.

[0253] It should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and are not intended to limit the present invention. Although the present invention has been described in detail with reference to the preferred embodiments, those skilled in the art should understand that the technical solutions of the present invention may be modified or replaced by equivalents without departing from the spirit and scope of the technical solutions of the present invention, and all of these should be included in the scope of the present invention.

Claims

1. A method for preparing alkyl ethers by catalyzing 5-hydroxymethylfurfural using a dual-catalyst synergistic one-step process, characterized in that: include, Using 5-hydroxymethylfurfural as a raw material and a low-carbon alcohol as a reaction solvent, catalyst A and catalyst B are added, and the 2,5-furan dimethanol alkyl ether is prepared by catalytic hydrogenation etherification under a hydrogen pressure atmosphere; The catalyst A is a bimetallic supported catalyst, in which two metals are supported on a carrier to catalyze the hydrogenation of 5-hydroxymethylfurfural to produce the intermediate 2,5-furan dimethanol, wherein the bimetallic supported catalyst comprises a carrier, a metal component X and a metal component Y supported on the carrier; Wherein, the carrier is alumina; the metal component X is selected from Cu; the metal component Y is selected from alkali metal elements, and the alkali metal element is any one of Na, K, and Cs; The metal loading amount of the metal component X loaded on the catalyst A is 0.1 wt% to 20 wt%, and the metal loading amount of the metal component Y loaded on the catalyst A is 0.01 wt% to 15 wt%; The catalyst B is a silica-alumina molecular sieve, and the intermediate obtained by etherification in the mixed system is used to prepare 2,5-furan dimethanol alkyl ether, wherein the silica-alumina molecular sieve is Al-MCM-41 molecular sieve with a silica-alumina ratio of 25:1; The reaction solvent is one of methanol, ethanol, n-propanol, isopropanol, and n-butanol; the mass ratio of catalyst A to catalyst B is 10:1 to 1:1; and the mass ratio of 5-hydroxymethylfurfural to the total mass of the two catalysts is 1:1 to 30:

1. The catalyst A is loaded with metal component X and metal component Y by pressure impregnation, and the loading order is first loading the active metal component X, drying and calcining after loading, crushing it evenly, and then loading the modified metal component Y; wherein, the pressure impregnation method has an impregnation pressure of 0.1MPa~2MPa, a loading temperature of 50℃~150℃, and a loading time of 3h~12h.

2. The method according to claim 1, wherein: The reaction temperature is 50-200° C., the reaction time is 0.5-10 hours, the concentration of 5-hydroxymethylfurfural in the reaction solution is 0.1-3000 mM, and the hydrogen pressure is 0.1 MPa-8 MPa.

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