CN113582952B - Method for preparing 2, 5-furandicarboxylic acid by using straw - Google Patents
Method for preparing 2, 5-furandicarboxylic acid by using straw Download PDFInfo
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- CN113582952B CN113582952B CN202111014207.0A CN202111014207A CN113582952B CN 113582952 B CN113582952 B CN 113582952B CN 202111014207 A CN202111014207 A CN 202111014207A CN 113582952 B CN113582952 B CN 113582952B
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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
- C07D307/34—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
- C07D307/56—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/16—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J29/166—Y-type faujasite
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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
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
- B01J2229/186—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself not in framework positions
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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Abstract
The invention discloses a method for preparing 2, 5-furandicarboxylic acid by using straws, which mixes a chromium-manganese loaded USY molecular sieve integral catalyst and straws with a mixed solvent consisting of dimethyl sulfoxide and water, and carries out a catalytic reaction by heating to obtain the 2, 5-furandicarboxylic acid, wherein the chromium-manganese loaded USY molecular sieve integral catalyst takes a USY molecular sieve as a carrier and is loaded with chromium element and manganese element, and the chromium element and the manganese element exist in a form of metal oxide. The chromium-manganese supported USY molecular sieve integral catalyst has the advantages of high catalytic efficiency, high yield, strong stability, high recovery efficiency, low raw material cost, low energy consumption and the like, is used for generating 2, 5-furandicarboxylic acid, has the yield of 67 percent, is suitable for large-scale batch production, and has good market prospect.
Description
Technical Field
The invention belongs to the fields of chemical technology and agricultural waste recycling, relates to the field of biorefinery, and in particular relates to a method for preparing 2, 5-furandicarboxylic acid by using straws.
Background
With the rapid development of industry, the increasing exhaustion of energy sources such as fossil fuels and the like makes people start to search for new sustainable energy sources, and the preparation of biomass into high-value platform compounds is one of important ways for realizing the effective utilization of biomass resources. 2, 5-furandicarboxylic acid is listed by the U.S. department of energy as one of the twelve most representative biobased platform compounds as an important furan compound and is also considered the most suitable alternative to the petroleum derivative terephthalic acid. The 2, 5-furandicarboxylic acid has a structure similar to terephthalic acid, and can replace terephthalic acid as a raw material of polyethylene terephthalate which is widely used, thereby reducing the dependence on fossil fuel. However, the current research on the synthesis of 2, 5-furandicarboxylic acid is mostly based on 5-hydroxymethylfurfural, fructose, glucose and the like, and the technical development route is very limited. Among them, the synthesis of 2, 5-furandicarboxylic acid from 5-hydroxymethylfurfural oxygen (HMF) is the most important technical route, and is generally obtained by the oxidative synthesis of refined 5-hydroxymethylfurfural oxygen (HMF) or by the dehydration of 5-hydroxymethylfurfural oxygen (HMF) with hexose. However, the production route based on the refined product has high cost, and is difficult to popularize and apply in a large range. Therefore, the search for direct production of high-value 2, 5-furandicarboxylic acid based on lignocellulosic biomass is a new direction.
At present, research on the preparation of value-added chemicals by biomass has attracted attention, but the structure of lignocellulose biomass is complex, the conversion rate of target products is very low, and the research on the production of 2, 5-furandicarboxylic acid by biomass is less. Therefore, how to directly prepare high-value 2, 5-furandicarboxylic acid chemicals through biomass has great significance for improving the utilization rate of biomass.
Disclosure of Invention
The invention aims to solve the technical problems of overcoming the defects of the prior art and providing the method for preparing the 2, 5-furandicarboxylic acid by using the straws, which has the advantages of high catalytic efficiency, high yield, strong stability, high recovery efficiency, low raw material cost and low energy consumption.
In order to solve the technical problems, the invention adopts the following technical scheme.
A method for preparing 2, 5-furandicarboxylic acid by using straws comprises the following steps: mixing a chromium-manganese loaded USY molecular sieve integral catalyst, straw and a mixed solvent, heating to 120-240 ℃ for biomass catalytic reaction to obtain 2, 5-furandicarboxylic acid; the chromium-manganese supported USY molecular sieve integral catalyst takes a USY molecular sieve as a carrier, chromium element and manganese element are supported on the USY molecular sieve, the chromium element and the manganese element exist in a metal oxide form, and the mixed solvent consists of dimethyl sulfoxide and water.
In the method for preparing 2, 5-furandicarboxylic acid by using straws, preferably, the ratio of the chromium-manganese supported USY molecular sieve monolithic catalyst to the straws to the mixed solvent is 0.3 g-1.1 g:0.5 g-2 g:50 mL, and the volume ratio of dimethyl sulfoxide to water in the mixed solvent is 1:1.
In the method for preparing 2, 5-furandicarboxylic acid by using the straw, preferably, the straw is rice straw.
In the method for preparing 2, 5-furandicarboxylic acid by using straw, preferably, ultrasonic treatment is performed before heating, the ultrasonic treatment time is 30-60 min, and the biomass catalytic reaction time is 4-6 h.
In the method for preparing 2, 5-furandicarboxylic acid by using straw, preferably, the loading amount of the chromium element is 3-9% of the mass of the chromium-manganese loaded USY molecular sieve monolithic catalyst, and the loading amount of the manganese element is 3-9% of the mass of the chromium-manganese loaded USY molecular sieve monolithic catalyst.
In the method for preparing 2, 5-furandicarboxylic acid by using straw, preferably, the preparation method of the chromium-manganese supported USY molecular sieve monolithic catalyst comprises the following steps:
(1) Dissolving a manganese nitrate solution, chromium nitrate nonahydrate and a silica sol solution in water and stirring to obtain a mixed solution;
(2) Adding USY molecular sieve material into the mixed solution, carrying out ultrasonic treatment, dipping and drying, and calcining at 300-500 ℃ to obtain the chromium-manganese supported USY molecular sieve integral catalyst.
In the method for preparing 2, 5-furandicarboxylic acid by using straw, preferably, the manganese nitrate is dissolvedThe proportion of the solution, the chromium nitrate nonahydrate, the silica sol solution, the water and the USY molecular sieve material is 0.52-6.18 mL:1.16-3.46 g:1 mL:100 mL:5 g, the mass fraction of the manganese nitrate solution is 50%, and the SiO in the silica sol solution is the same as that of the solution 2 The mass fraction of (2) is 29-31%. More preferably, the molar ratio of chromium element in the chromium nitrate nonahydrate to manganese element in the manganese nitrate solution is 1:1, 1:2 or 2:1.
In the method for preparing 2, 5-furandicarboxylic acid by using straw, preferably, in the step (2), the ultrasonic treatment time is 10-30 min, the soaking temperature is 80-100 ℃, the soaking time is 5-7 h, the drying temperature is 100-105 ℃, and the drying time is 1-2 h.
In the method for preparing 2, 5-furandicarboxylic acid by using straw, preferably, in the step (2), the calcination time is 3-5 h.
Compared with the prior art, the invention has the advantages that:
(1) The invention provides a method for preparing 2, 5-furandicarboxylic acid by using straws, which realizes the purpose of directly catalyzing and producing 2, 5-furandicarboxylic acid from straws of agricultural and forestry wastes and avoids the use of high-cost raw materials. In the invention, the chromium-manganese loaded USY molecular sieve monolithic catalyst takes a USY molecular sieve as a carrier, and chromium element and manganese element are loaded on the USY molecular sieve; the USY molecular sieve is used as a good solid acid carrier, can be effectively combined with Cr and Mn metal elements, and the Cr and Mn metal elements exist in a metal oxide form on the surface of the catalyst after impregnation and calcination, so that the surface of the catalyst has good oxygen mobility, the conversion from straw, hexose, 5-hydroxymethylfurfural, 2, 5-furandicarboxylic acid can be better realized, and the rate of each stage of reaction in the process of producing 2, 5-furandicarboxylic acid by straw catalysis is improved. That is, the chromium-manganese bimetallic loading in the chromium-manganese loaded USY molecular sieve monolithic catalyst can realize the direct catalysis of the straw to generate high-value 2, 5-furandicarboxylic acid. Compared with the existing synthesis method of 2, 5-furandicarboxylic acid, the method for preparing 2, 5-furandicarboxylic acid by using the straw has the advantages of low raw material cost, simplicity in operation, low energy consumption, short time consumption, high yield and the like, is suitable for large-scale batch production, and has good market prospect.
(2) In the method, the chromium-manganese supported USY molecular sieve integral catalyst is adopted, the design of the integral catalyst increases the material contact area, and the method has the advantages of high catalytic efficiency, strong stability, high recovery efficiency and the like.
Drawings
FIG. 1 is a graph (XPS graph) showing the valence analysis of Cr element of the chromium-manganese supported USY molecular sieve monolithic catalyst prepared in example 1 of the present invention.
Fig. 2 is a valence analysis chart (XPS chart) of Mn element of the chromium-manganese supported USY molecular sieve monolithic catalyst prepared in example 1 of the present invention.
FIG. 3 is an XRD pattern of the chromium-manganese supported USY molecular sieve monolith catalyst prepared in example 1 of the present invention.
FIG. 4 is a graph showing the effect of different catalyst addition amounts on the yield of 2, 5-furandicarboxylic acid in example 2 of the present invention.
FIG. 5 is a graph showing the effect of different amounts of straw added on the yield of 2, 5-furandicarboxylic acid in example 2 of the present invention.
FIG. 6 is a graph showing the effect of different catalytic reaction temperatures on the yield of 2, 5-furandicarboxylic acid in example 2 of the present invention.
FIG. 7 is a graph showing the variation of the yield of 2, 5-furandicarboxylic acid produced by catalyzing rice straw to recycle the chromium-manganese supported USY molecular sieve monolithic catalyst in example 3 of the present invention.
Detailed Description
The invention is further described below in connection with the drawings and the specific preferred embodiments, but the scope of protection of the invention is not limited thereby. The materials and instruments used in the examples below are all commercially available.
Example 1:
the invention relates to a method for preparing 2, 5-furandicarboxylic acid by using straws, in particular to a method for directly generating 2, 5-furandicarboxylic acid by using chromium-manganese loaded USY molecular sieve integral catalyst to catalyze straws, which comprises the following steps:
mixing 0.7g of chromium-manganese supported USY molecular sieve integral catalyst with 1g of rice straw, pouring the mixture into a mixed solvent medium consisting of 50mL of dimethyl sulfoxide and water, carrying out ultrasonic pretreatment for 30min, heating to 180 ℃ for catalytic reaction for 5h, and carrying out solid-liquid separation by a circulating vacuum pump after the reaction is completed to obtain 2, 5-furandicarboxylic acid. The concentration of 2, 5-furandicarboxylic acid in the solution obtained by solid-liquid separation was detected, and the result showed that the yield of 2, 5-furandicarboxylic acid was 67%.
In the embodiment, the integral catalyst of the USY molecular sieve loaded with chromium and manganese is prepared by taking a USY molecular sieve as a carrier, loading chromium element and manganese element on the USY molecular sieve, wherein the chromium element and the manganese element exist in the form of metal oxide, namely Cr 2 O 3 、CrO 3 、MnO 2 、Mn 2 O 3 、Mn 3 O 4 Wherein the loading amounts of the chromium element and the manganese element are respectively 6 percent of the total mass of the chromium-manganese loaded USY molecular sieve monolithic catalyst.
In the embodiment, the preparation method of the chromium-manganese supported USY molecular sieve monolithic catalyst comprises the following steps:
(1) 2.31g of chromium nitrate nonahydrate, 2.06mL of manganese nitrate solution and 1mL of silica sol solution are placed in a beaker, the mass fraction of the manganese nitrate solution is 50%, and SiO in the silica sol solution 2 29-31% of the mass fraction, adding 100mL of ultrapure water, and completely dissolving to form chromium-manganese mixed solution;
(2) 5g of USY molecular sieve is added into the chromium-manganese mixed solution, ultrasonic treatment is carried out for 20min under the stirring state, heating and soaking are carried out for 6h at 80 ℃, and the mixture is dried for 1h at 105 ℃ in an oven after the soaking is finished, thus obtaining the mixture. And (3) placing the mixture in a muffle furnace to calcine for 4h at 400 ℃ to obtain the chromium-manganese supported USY molecular sieve integral catalyst.
FIGS. 1 and 2 are XPS graphs of Cr and Mn, respectively, in a chromium-manganese supported USY molecular sieve monolithic catalyst prepared in example 1. As can be seen from the figure, cr exists in +3, +6 valence and Mn exists in +2, +3, +4 valence, which side reflects the good redox of the catalyst surface.
FIG. 3 is an XRD pattern of the chromium-manganese supported USY molecular sieve monolith catalyst prepared in example 1. As can be seen from the figure, cr and Mn metal elements exist in the form of oxides on the surface of the catalyst after being calcined, so that the speed of each stage of reaction in the process of producing 2, 5-furandicarboxylic acid by straw catalysis can be improved.
Example 2:
the influence of different reaction parameters on the yield of 2, 5-furandicarboxylic acid is examined, and the method specifically comprises the step of catalyzing straws to generate 2, 5-furandicarboxylic acid by adopting the chromium-manganese supported USY molecular sieve monolithic catalyst prepared in the example 1.
(1) Different catalyst addition amounts
Mixing 0.3g, 0.5g, 0.7g, 0.9g and 1.1g of chromium-manganese supported USY molecular sieve integral catalyst with 1g of rice straw, pouring the mixture into a mixed solvent medium consisting of 50mL of dimethyl sulfoxide and water, carrying out ultrasonic pretreatment for 30min in the mixed solvent, heating, carrying out catalytic reaction for 5h at the reaction temperature of 180 ℃, carrying out solid-liquid separation through a circulating vacuum pump after the reaction is completed, and detecting the concentration of 2, 5-furandicarboxylic acid in the solution obtained by the solid-liquid separation.
(2) Different straw feeding amounts
Mixing 0.7g of chromium-manganese supported USY molecular sieve monolithic catalyst with 0.5g, 1g, 1.5g and 2g of rice straw respectively, pouring the mixture into a mixed solvent medium consisting of 50mL of dimethyl sulfoxide and water, carrying out ultrasonic pretreatment for 30min, heating, carrying out catalytic reaction for 5h at the reaction temperature of 180 ℃, carrying out solid-liquid separation by a circulating vacuum pump after the reaction is finished to obtain 2, 5-furandicarboxylic acid, and detecting the concentration of 2, 5-furandicarboxylic acid in a solution obtained by solid-liquid separation.
(3) Different catalytic reaction temperatures
Mixing 0.7g of chromium-manganese supported USY molecular sieve monolithic catalyst with 1g of rice straw, pouring the mixture into a mixed solvent medium consisting of 50mL of dimethyl sulfoxide and water, carrying out ultrasonic pretreatment for 30min, heating, respectively carrying out catalytic reaction for 5h at the reaction temperature of 120 ℃ and 150 ℃, 180 ℃, 210 ℃ and 240 ℃, carrying out solid-liquid separation by a circulating vacuum pump after the reaction is finished, obtaining 2, 5-furandicarboxylic acid, and detecting the concentration of 2, 5-furandicarboxylic acid in a solution obtained by the solid-liquid separation.
Fig. 4 to 6 are graphs showing the effect of different reaction parameters on the yield of 2, 5-furandicarboxylic acid in example 2, wherein fig. 4 shows the effect of different catalyst addition amounts on the yield, fig. 5 shows the effect of different straw addition amounts on the yield, and fig. 6 shows the effect of different catalytic reaction temperatures on the yield. As can be seen from the graph, the yield of the 2, 5-furandicarboxylic acid can reach 67% under the conditions of 0.7g of catalyst dosage, 1g of straw dosage, 180 ℃ of reaction temperature and 5h of reaction time.
Example 3:
the reusability of the chromium-manganese loaded USY molecular sieve monolithic catalyst in the process of catalyzing and generating 2, 5-furandicarboxylic acid is examined. The monolithic catalyst after the reaction in the example 1 is simply washed by pure water, dried and used for the next catalytic reaction, and the preparation steps are the same as those in the example 1, namely, the reaction parameters are that the catalyst addition amount is 0.7g, the straw addition amount is 1g, the reaction temperature is 180 ℃, and the reaction time is 5 hours. After the reaction is completed, the next cycle is carried out.
FIG. 7 is a graph showing the variation of yield of 2, 5-furandicarboxylic acid produced from rice straw by recycling the chromium-manganese supported USY molecular sieve monolithic catalyst in example 3. The graph shows that the chromium-manganese supported USY molecular sieve integral catalyst has good recycling property, and the catalytic effect basically keeps unchanged in 6 times of recycling, so that the catalyst is a novel catalytic material with good stability and high efficiency, and has wide application prospect.
The above description is only of the preferred embodiment of the present invention, and is not intended to limit the present invention in any way. While the invention has been described in terms of preferred embodiments, it is not intended to be limiting. Any person skilled in the art can make many possible variations and modifications to the technical solution of the present invention or equivalent embodiments using the method and technical solution disclosed above without departing from the spirit and technical solution of the present invention. Therefore, any simple modification, equivalent substitution, equivalent variation and modification of the above embodiments according to the technical substance of the present invention, which do not depart from the technical solution of the present invention, still fall within the scope of the technical solution of the present invention.
Claims (9)
1. A method for preparing 2, 5-furandicarboxylic acid by using straws, which is characterized by comprising the following steps: mixing a chromium-manganese loaded USY molecular sieve integral catalyst, straw and a mixed solvent, heating to 120-240 ℃ for biomass catalytic reaction to obtain 2, 5-furandicarboxylic acid; the chromium-manganese supported USY molecular sieve integral catalyst takes a USY molecular sieve as a carrier, chromium element and manganese element are supported on the USY molecular sieve, the chromium element and the manganese element exist in a metal oxide form, and the mixed solvent consists of dimethyl sulfoxide and water.
2. The method for preparing 2, 5-furandicarboxylic acid by using straws according to claim 1, wherein the chromium-manganese loaded USY molecular sieve monolithic catalyst and the ratio of the straws to the mixed solvent are 0.3 g-1.1 g:0.5 g-2 g:50 mL, and the volume ratio of dimethyl sulfoxide to water in the mixed solvent is 1:1.
3. The method for preparing 2, 5-furandicarboxylic acid from straw according to claim 1, wherein the straw is rice straw.
4. The method for preparing 2, 5-furandicarboxylic acid by using straw according to claim 1, wherein the ultrasonic treatment is performed before heating, the ultrasonic treatment time is 30-60 min, and the biomass catalytic reaction time is 4-6 h.
5. The method for preparing 2, 5-furandicarboxylic acid by using straw according to any one of claims 1 to 4, wherein the loading amount of the chromium element is 3 to 9% of the mass of the chromium-manganese loaded USY molecular sieve monolithic catalyst, and the loading amount of the manganese element is 3 to 9% of the mass of the chromium-manganese loaded USY molecular sieve monolithic catalyst.
6. The method for preparing 2, 5-furandicarboxylic acid by using straw according to any one of claims 1 to 4, wherein the preparation method of the chromium-manganese supported USY molecular sieve monolithic catalyst comprises the following steps:
(1) Dissolving a manganese nitrate solution, chromium nitrate nonahydrate and a silica sol solution in water and stirring to obtain a mixed solution;
(2) Adding USY molecular sieve material into the mixed solution, carrying out ultrasonic treatment, dipping and drying, and calcining at 300-500 ℃ to obtain the chromium-manganese supported USY molecular sieve integral catalyst.
7. The method for preparing 2, 5-furandicarboxylic acid from straw according to claim 6, wherein the ratio of manganese nitrate solution, chromium nitrate nonahydrate, silica sol solution, water and USY molecular sieve material is 0.52-6.18 mL:1.16-3.46 g:1 mL:100 mL:5 g, the mass fraction of the manganese nitrate solution is 50%, and the silica sol solution contains SiO 2 The mass fraction of (2) is 29-31%.
8. The method for preparing 2, 5-furandicarboxylic acid from straw according to claim 6, wherein in the step (2), the ultrasonic treatment is performed for 10 to 30 minutes, the impregnation temperature is 80 to 100 ℃, the impregnation time is 5 to 7 hours, the drying temperature is 100 to 105 ℃, and the drying time is 1 to 2 hours.
9. The method for preparing 2, 5-furandicarboxylic acid from straw according to claim 6, wherein in the step (2), the calcination time is 3 to 5 hours.
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