CN112547071B - Catalyst for preparing tetrahydrofuran by hydrogenation of furan and preparation method and application thereof - Google Patents
Catalyst for preparing tetrahydrofuran by hydrogenation of furan and preparation method and application thereof Download PDFInfo
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- CN112547071B CN112547071B CN202011494123.7A CN202011494123A CN112547071B CN 112547071 B CN112547071 B CN 112547071B CN 202011494123 A CN202011494123 A CN 202011494123A CN 112547071 B CN112547071 B CN 112547071B
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- 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
- B01J23/74—Iron group metals
- B01J23/755—Nickel
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/024—Multiple impregnation or coating
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
- B01J37/082—Decomposition and pyrolysis
- B01J37/088—Decomposition of a metal salt
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/16—Reducing
- B01J37/18—Reducing with gases containing free hydrogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D307/08—Preparation of tetrahydrofuran
Abstract
The invention provides a catalyst for preparing tetrahydrofuran by furan hydrogenation, a preparation method and application thereof; the preparation method comprises the following steps: a) Loading Ni source on TiO by dipping method 2 ‑Al 2 O 3 On the composite carrier, obtaining the catalyst in an oxidation state; b) Reducing the oxidation state catalyst obtained in the step a) in a hydrogen atmosphere to obtain the catalyst for preparing tetrahydrofuran by furan hydrogenation. Compared with the prior art, the catalyst prepared by the preparation method is suitable for preparing tetrahydrofuran by furan hydrogenation, has the characteristics of strong adaptability, long service life, high activity, good selectivity and the like, and has the advantages of simple preparation, low cost and wide application prospect compared with the problems of expensive noble metal Pd/C and Raney Ni equivalent, sensitive catalyst and the like adopted by the traditional catalyst. Experimental results show that the catalyst prepared by the preparation method is used for preparing tetrahydrofuran by hydrogenation of furan, the conversion rate of furan is as high as 98.31%, and the selectivity of tetrahydrofuran is as high as 92.50%.
Description
Technical Field
The invention relates to the technical field of catalysts, in particular to a catalyst for preparing tetrahydrofuran by furan hydrogenation and a preparation method and application thereof.
Background
Tetrahydrofuran (THF) is an organic solvent with excellent performance widely used in industrial production, has the characteristics of low toxicity, low boiling point, good fluidity, excellent solubility and the like, is a universal solvent, is also an important organic synthesis raw material, and has wide application.
The method for producing tetrahydrofuran mainly comprises a Reppe method and a furfural method; the preparation of tetrahydrofuran by furan hydrogenation is a technological process for producing tetrahydrofuran by a furfural method. At present, catalysts for preparing tetrahydrofuran by hydrogenating furan mainly comprise Pd/C and Raney Ni, and mainly adopt kettle type production, wherein the Pd/C catalyst has high price, and the furan conversion rate is less than 95 percent; while the Raney Ni catalyst is generally used in an amount of 8-12%, the furan conversion is high, but the selectivity is poor.
Disclosure of Invention
In view of the above, the present invention aims to provide a catalyst for preparing tetrahydrofuran by furan hydrogenation, and a preparation method and an application thereof.
The invention provides a preparation method of a catalyst for preparing tetrahydrofuran by furan hydrogenation, which comprises the following steps:
a) Loading Ni source on TiO by dipping method 2 -Al 2 O 3 On the composite carrier, obtaining the catalyst in an oxidation state;
b) Reducing the oxidation state catalyst obtained in the step a) in a hydrogen atmosphere to obtain the catalyst for preparing tetrahydrofuran by furan hydrogenation.
Preferably, the Ni source in step a) is selected from one or more of nickel nitrate, nickel acetate and basic nickel carbonate.
Preferably, the TiO in step a) 2 -Al 2 O 3 The specific surface area of the composite carrier is 160m 2 /g～240m 2 The pore volume is 0.42 ml/g-0.48 ml/g, and the particle strength is 100N/cm-140N/cm.
Preferably, the Ni source is loaded on TiO by adopting an impregnation method in the step a) 2 -Al 2 O 3 The process on the composite carrier is specifically as follows:
a1 Preparing an aqueous solution of Ni source, dipping in TiO in two times 2 -Al 2 O 3 On the composite carrier, drying for 3-6 h at 80-120 ℃ after first impregnation, and then roasting for 3-6 h at 480-540 ℃ to obtain a roasted product;
a2 A) carrying out second impregnation on the roasted product obtained in the step a 1), then drying for 3-6 h at the temperature of 80-120 ℃, and finally roasting for 2-6 h at the temperature of 480-540 ℃ to obtain the oxidation state catalyst.
Preferably, the hydrogen partial pressure of the hydrogen atmosphere in the step b) is 0.4 to 0.6MPa, and the gas-to-agent ratio is (1200 to 1800): 1.
preferably, the temperature of the reduction in the step b) is 180-200 ℃ and the time is 36-60 h.
Preferably, the Ni content of the catalyst for preparing tetrahydrofuran by hydrogenating furan in the step b) is 16-22 wt%, and the Ti content is 6-10 wt%.
The invention also provides a catalyst for preparing tetrahydrofuran by furan hydrogenation, which is prepared by the preparation method of the technical scheme.
The invention also provides a method for preparing tetrahydrofuran, which comprises the following steps:
on a fixed bed reactor, the catalyst for preparing tetrahydrofuran by hydrogenating furan according to the technical scheme is adopted, and tetrahydrofuran is obtained by reacting furan liquid with hydrogen.
Preferably, the volume space velocity of the furan liquid is 1.0h -1 ～2.0h -1 The molar ratio of hydrogen to oil is (800-1000): 1, the reaction pressure is 1.0MPa to 3.0MPa, and the reaction temperature is 160 ℃ to 210 ℃.
The invention provides a catalyst for preparing tetrahydrofuran by furan hydrogenation, a preparation method and application thereof; the preparation method comprises the following steps: a) Loading Ni source on TiO by dipping method 2 -Al 2 O 3 On the composite carrier, obtaining the catalyst in an oxidation state; b) Reducing the oxidation state catalyst obtained in the step a) in a hydrogen atmosphere to obtain the catalyst for preparing tetrahydrofuran by furan hydrogenation. Compared with the prior art, the catalyst prepared by the preparation method is suitable for preparing tetrahydrofuran by furan hydrogenation, has the characteristics of strong adaptability, long service life, high activity, good selectivity and the like, and has the advantages of simple preparation, low cost and wide application prospect compared with the problems of expensive noble metal Pd/C and Raney Ni equivalent, sensitive catalyst and the like adopted by the traditional catalyst. Experimental results show that the preparation method provided by the inventionThe catalyst obtained by the method is used for preparing tetrahydrofuran by hydrogenating furan, the conversion rate of the furan is as high as 98.31%, and the selectivity of the tetrahydrofuran is as high as 92.50%.
Meanwhile, the preparation method provided by the invention is simple to operate, easy to control conditions and suitable for industrial production and application.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without making any creative effort based on the embodiments in the present invention, belong to the protection scope of the present invention.
The invention provides a preparation method of a catalyst for preparing tetrahydrofuran by furan hydrogenation, which comprises the following steps:
a) Loading Ni source on TiO by dipping method 2 -Al 2 O 3 On the composite carrier, obtaining the catalyst in an oxidation state;
b) Reducing the oxidation state catalyst obtained in the step a) in a hydrogen atmosphere to obtain the catalyst for preparing tetrahydrofuran by furan hydrogenation.
The invention firstly adopts the dipping method to load the Ni source on the TiO 2 -Al 2 O 3 And (4) obtaining the catalyst in an oxidation state on the composite carrier. In the present invention, the Ni source is preferably selected from one or more of nickel nitrate, nickel acetate, and basic nickel carbonate, and more preferably nickel nitrate. The source of the Ni source is not particularly limited in the present invention, and commercially available products of the above nickel nitrate, nickel acetate and basic nickel carbonate, which are well known to those skilled in the art, may be used. In a preferred embodiment of the invention, the Ni source is Ni (NO) 3 ) 2 ·6H 2 O。
In the present invention, the TiO is 2 -Al 2 O 3 The specific surface area of the composite carrier is preferably 160m 2 /g～240m 2 The pore volume is preferably 0.42ml/g to 0.48ml/g, and the particle strength is preferably 100N/cm to 140N/cm. The invention is directed to the TiO 2 -Al 2 O 3 The source of the composite carrier is not particularly limited, and commercially available products or self-prepared products known to those skilled in the art may be used. In a preferred embodiment of the invention, the TiO is 2 -Al 2 O 3 The composite carrier is in particular 18wt% TiO 2 -82wt％Al 2 O 3 (ii) a The amount thereof can be determined according to the final content of each component in the catalyst.
In the invention, the Ni source is loaded on TiO by adopting an immersion method 2 -Al 2 O 3 The process on the composite carrier is preferably embodied as follows:
a1 Preparing an aqueous solution of Ni source, dipping in TiO in two times 2 -Al 2 O 3 On the composite carrier, drying for 3-6 h at 80-120 ℃ after first impregnation, and then roasting for 3-6 h at 480-540 ℃ to obtain a roasted product;
a2 A) carrying out second impregnation on the roasted product obtained in the step a 1), then drying for 3-6 h at the temperature of 80-120 ℃, and finally roasting for 2-6 h at the temperature of 480-540 ℃ to obtain the oxidation state catalyst.
More preferably:
a1 Preparing an aqueous solution of Ni source, dipping in TiO in two times 2 -Al 2 O 3 On the composite carrier, drying for 4 hours at 110 ℃ after first impregnation, and then roasting for 4 hours at 520 ℃ to obtain a roasted product;
a2 A second impregnation of the calcined product obtained in step a 1), followed by drying at 110 ℃ for 4h and finally calcination at 500 ℃ for 3h, gives the catalyst in the oxidized state.
After the catalyst in the oxidation state is obtained, the catalyst in the oxidation state is reduced in a hydrogen atmosphere to obtain the catalyst for preparing tetrahydrofuran by furan hydrogenation. In the present invention, the hydrogen partial pressure of the hydrogen atmosphere is preferably 0.4 to 0.6MPa, more preferably 0.5MPa; the gas-to-agent ratio (volume ratio of hydrogen to catalyst in an oxidized state) of the hydrogen atmosphere is preferably (1200 to 1800): 1, more preferably 1500:1.
in the present invention, the temperature of the reduction is preferably 180 ℃ to 200 ℃, and more preferably 190 ℃; the reduction time is preferably 36 to 60 hours, more preferably 48 hours.
In the present invention, the above-mentioned process of reducing the obtained catalyst in an oxidized state in a hydrogen atmosphere may be carried out in a fixed bed reactor well known to those skilled in the art, and the present invention is not particularly limited thereto; meanwhile, after the reduction, the obtained catalyst can be directly used for preparing tetrahydrofuran by furan hydrogenation.
In the invention, the Ni content of the catalyst for preparing tetrahydrofuran by hydrogenating furan is preferably 16-22 wt%, and more preferably 20-22 wt%; the Ti content of the catalyst for preparing tetrahydrofuran by furan hydrogenation is preferably 6-10 wt%, and more preferably 6-8 wt%; the remaining component is mainly alumina, and the present invention is not particularly limited thereto.
The preparation method provided by the invention is simple to operate, easy to control conditions and suitable for industrial production and application.
The invention also provides a catalyst for preparing tetrahydrofuran by furan hydrogenation, which is prepared by the preparation method of the technical scheme. In the invention, the catalyst for preparing tetrahydrofuran by furan hydrogenation is a nickel-based catalyst; the specific surface area of the powder is 140m 2 /g～200m 2 The volume of the pores is 0.42 ml/g-0.48 ml/g, and the strength of the particles is 80N/cm-120N/cm.
The invention develops the use of TiO 2 -Al 2 O 3 The composite carrier is prepared into the nickel-based catalyst with good dispersion by combining an impregnation method and a specific reduction process, so that the cost of the catalyst in the prior art is reduced, the conversion rate of furan and the selectivity of tetrahydrofuran are considered, the operation difficulty of an industrial device is simplified, and the preparation method has wide application prospects.
The invention also provides a method for preparing tetrahydrofuran, which comprises the following steps:
on a fixed bed reactor, the catalyst for preparing tetrahydrofuran by furan hydrogenation according to the technical scheme is adopted, and tetrahydrofuran is obtained by reacting furan liquid with hydrogen.
In the invention, the fixed bed reactor is adopted to realize the continuous production of tetrahydrofuran; the fixed bed reactor is not particularly limited, and the preparation process of the catalyst is carried out in the fixed bed reactor, so that the prepared catalyst can be directly used for preparing tetrahydrofuran.
The catalyst for preparing tetrahydrofuran by furan hydrogenation according to the technical scheme is not repeated herein. The source of the hydrogen and furan liquid is not particularly limited in the present invention, and commercially available products or self-products known to those skilled in the art may be used.
In the invention, the volume space velocity of the furan liquid is preferably 1.0h -1 ～2.0h -1 More preferably 1.0h -1 (ii) a The hydrogen-oil (hydrogen gas, furan liquid) molar ratio is preferably (800-1000): 1, more preferably 1000:1; the reaction pressure is preferably 1.0 to 3.0MPa, more preferably 2.0 to 3.0MPa, and more preferably 3.0MPa; the reaction temperature is preferably 160 ℃ to 210 ℃, more preferably 200 ℃ to 210 ℃.
The invention provides a catalyst for preparing tetrahydrofuran by furan hydrogenation, a preparation method and application thereof; the preparation method comprises the following steps: a) Loading Ni source on TiO by dipping method 2 -Al 2 O 3 On the composite carrier, obtaining the catalyst in an oxidation state; b) Reducing the oxidation state catalyst obtained in the step a) in a hydrogen atmosphere to obtain the catalyst for preparing tetrahydrofuran by furan hydrogenation. Compared with the prior art, the catalyst prepared by the preparation method is suitable for preparing tetrahydrofuran by furan hydrogenation, has the characteristics of strong adaptability, long service life, high activity, good selectivity and the like, and has the advantages of simple preparation, low cost and wide application prospect compared with the problems of expensive noble metal Pd/C and Raney Ni equivalent, sensitive catalyst and the like adopted by the traditional catalyst. Experimental results show that when the catalyst prepared by the preparation method is used for preparing tetrahydrofuran by furan hydrogenation, the furan conversion rate is up to 98.31%, and the tetrahydrofuran selectivity is up to 92.50%.
Meanwhile, the preparation method provided by the invention is simple to operate, easy to control conditions and suitable for industrial production and application.
To further illustrate the present invention, the following examples are provided for illustration. The starting materials used in the following examples of the present invention are all commercially available products.
Example 1
(1) 98.48g of Ni (NO) are weighed out 3 ) 2 ·6H 2 O was prepared as a 50ml aqueous solution and impregnated twice into the composite support (18wt% TiO) 2 -82wt％Al 2 O 3 ) After the first dipping, drying the mixture in an oven at 110 ℃ for 4h, and then roasting the mixture in a muffle furnace at 520 ℃ for 4h; and (3) carrying out second impregnation on the roasted product, drying the product in an oven at 110 ℃ for 4h, and roasting the product in a muffle furnace at 500 ℃ for 3h to obtain the oxidized catalyst.
(2) Reducing the oxidation state catalyst obtained in the step (1) in a hydrogen atmosphere, wherein the hydrogen partial pressure is 0.5MPa, and the gas-agent ratio is 1500:1, the reduction temperature is 190 ℃, the reduction time is 48h, and the catalyst for preparing tetrahydrofuran by furan hydrogenation is obtained.
The detection proves that the catalyst is a nickel-based catalyst, wherein the Ni content is 20wt%, the Ti content is 8wt%, and the specific surface area is 170m 2 The pore volume was 0.45ml/g, and the particle strength was 100N/cm.
Examples 2 to 5
By adopting the preparation method provided by the embodiment 1, the catalyst for preparing tetrahydrofuran by hydrogenating furan is obtained; the difference is the Ni content and Ti content, as shown in table 2.
Application example 1
Tetrahydrofuran was prepared over a 10ml fixed bed reactor using the catalyst provided in example 1:
under the condition of hydrogen, the volume space velocity of furan liquid is 1.0h -1 The molar ratio of hydrogen to oil is 1000:1, the reaction pressure is 3.0MPa, the reaction temperature is 210 ℃, and the tetrahydrofuran is prepared.
The detection proves that the conversion rate of furan is 98.09%, and the selectivity of tetrahydrofuran is 92.01%.
Application examples 2 to 5
The tetrahydrofuran was prepared by the method provided in application example 1, and the specific conditions and parameters, furan conversion, and tetrahydrofuran selectivity are shown in table 1.
TABLE 1 conditions and parameters, furan conversion, tetrahydrofuran selectivity of the application examples 1 to 5 of the present invention
Application examples 6 to 9
Tetrahydrofuran was prepared by the method provided in application example 1 except that the catalysts of examples 2 to 5 were respectively used instead of the catalyst of example 1, and the specific catalysts, furan conversion and tetrahydrofuran selectivity were as shown in table 2.
TABLE 2 catalysts, furan conversion, tetrahydrofuran Selectivity of the invention using examples 1, 6 to 9
| Catalyst and process for preparing same | Furan conversion/% | Tetrahydrofuran selectivity/%) | |
| Application example 6 | 16wt％Ni@Ti-Al 2 O 3 (Ti content 6 wt%) | 90.02 | 90.11 |
| Application example 7 | 18wt％Ni@Ti-Al 2 O 3 (Ti content 6 wt%) | 90.33 | 90.17 |
| Application example 8 | 20wt％Ni@Ti-Al 2 O 3 (Ti content 6 wt%) | 96.78 | 91.45 |
| Application example 1 | 20wt％Ni@Ti-Al 2 O 3 (Ti content 8 wt%) | 98.09 | 92.01 |
| Application example 9 | 22wt％Ni@Ti-Al 2 O 3 (Ti content 8 wt%) | 98.31 | 90.12 |
Note: the above Ti content means the content thereof in the catalyst
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (1)
1. A process for the preparation of tetrahydrofuran comprising the steps of:
on a 10ml fixed bed reactor, adopting a catalyst for preparing tetrahydrofuran by furan hydrogenation, and reacting furan liquid through hydrogen to obtain tetrahydrofuran;
the preparation method of the catalyst for preparing tetrahydrofuran by hydrogenating furan comprises the following steps:
(1) 98.48g of Ni (NO) are weighed out 3 ) 2 ·6H 2 O was prepared as a 50ml aqueous solution and impregnated twice into the composite carrier at 18wt% of TiO 2 -82wt%Al 2 O 3 After the first dipping, drying the mixture in an oven at 110 ℃ for 4h, and then roasting the mixture in a muffle furnace at 520 ℃ for 4h; the roasted product is dipped for the second time, then dried for 4 hours in an oven at 110 ℃, and finally roasted for 3 hours in a muffle furnace at 500 ℃ to obtain the oxidation state catalyst;
(2) Reducing the oxidation-state catalyst obtained in the step (1) in a hydrogen atmosphere, wherein the hydrogen partial pressure is 0.5MPa, and the gas-to-agent ratio is 1500: the reduction temperature is 190 ℃, the reduction time is 48 hours, and the catalyst for preparing tetrahydrofuran by furan hydrogenation is obtained, wherein the Ni content is 20wt%, the Ti content is 8wt%, and the specific surface area is 170m 2 The volume of pores is 0.45ml/g, and the strength of particles is 100N/cm;
the process of reacting furan liquid with hydrogen comprises the following specific steps:
under the condition of hydrogen, the volume space velocity of furan liquid is 1.0h -1 The molar ratio of hydrogen to oil is 1000:1, preparing tetrahydrofuran at the reaction pressure of 3.0MPa and the reaction temperature of 210 ℃;
the detection proves that the conversion rate of furan is 98.09%, and the selectivity of tetrahydrofuran is 92.01%.
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