CN109759113B - Preparation method of solid catalyst for catalyzing glucose dehydration - Google Patents
Preparation method of solid catalyst for catalyzing glucose dehydration Download PDFInfo
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Abstract
The invention belongs to the technical field of catalyst preparation, and particularly relates to a preparation method of a solid catalyst for catalyzing glucose dehydration. Adding chitosan and SBA-15 into water, uniformly mixing, and evaporating water under the condition of heating and stirring to obtain dry solid particles; roasting the solid particles to obtain black solid powder; soaking black solid powder in a hydrogen fluoride solution, filtering, and drying to obtain a mesoporous carbon-nitrogen material; and soaking the prepared mesoporous carbon nitrogen material in an acid solution, filtering, cleaning and drying to obtain the solid catalyst for catalyzing glucose dehydration. The mesoporous carbon-nitrogen material has certain alkalinity, can chemically adsorb acid at low temperature, can release acid to catalyze glucose to dehydrate at high temperature to prepare 5-HMF, and can recover the acid after the reaction.
Description
Technical Field
The invention belongs to the technical field of catalyst preparation, and particularly relates to a preparation method of a solid catalyst for catalyzing glucose dehydration.
Background
The biomass is considered as the most ideal substitute of fossil resources due to wide distribution, abundant reserves, short renewable period, low price and easy acquisition. 5-HMF is identified as one of the ten most valuable chemicals for the synthesis of various chemicals and biofuels. Glucose is the most abundant and least costly monosaccharide, and because it is readily available through hemicellulose and cellulose, the dehydration of glucose to 5-HMF is of great interest.
The catalysts for preparing 5-HMF by glucose dehydration are mainly divided into two types, one is a homogeneous catalyst, and the other is a heterogeneous catalyst. Homogeneous catalysts such as hydrochloric acid, sulfuric acid, heteropolyacids, ionic liquids, metal chlorides and the like. The homogeneous catalyst shows better catalytic activity in the aspect of catalyzing glucose dehydration, but has serious defects such as difficult recycling of the catalyst, difficult separation of a product and the catalyst, corrosion of equipment, poor product selectivity, environmental pollution and the like, and limits further application of the homogeneous catalyst in glucose dehydration. Heterogeneous catalysts such as sulfonated carbon, H-type molecular sieves, metal oxides, and the like. Because heterogeneous catalysis has the unique advantages of easy product separation, reusable catalyst, less corrosion, less environmental pollution and the like, more and more researchers focus on the heterogeneous catalyst to catalyze the dehydration of monosaccharide to prepare 5-HMF.
Chinese patent CN108610311A discloses a method for preparing 5-hydroxymethylfurfural by using boehmite to catalyze glucose at low temperature. Specifically, boehmite gamma-AlOOH and glucose are added into dimethyl sulfoxide to be mixed and stirred for reaction, deionized water is added into reaction liquid after the reaction is finished to carry out quenching treatment, centrifugation is carried out, and upper-layer liquid is collected to obtain the degradation liquid containing 5-hydroxymethylfurfural.
Chinese patent CN107629027A discloses a method for preparing 5-hydroxymethylfurfural by catalyzing biomass with a phosphorylated composite oxide. The method adopts the phosphorylation composite oxide solid acid as the catalyst, and adjusts the acidity of the catalyst by adjusting the adding amount of phosphoric acid and the proportion of Ti/Si components, thereby optimizing the catalytic performance of the preparation of HMF by glucose and biomass dehydration.
Chinese patent CN107337657A discloses a method for preparing 5-hydroxymethylfurfural in green by using monosaccharide. Glucose and fructose are used as reaction raw materials, zirconium phosphate, niobium phosphate and sulfated zirconia which are low in price and free of environmental pollution are used as catalysts, and a fixed bed is used as a reactor to catalyze monosaccharide to prepare HMF.
Chinese patent CN105797711A discloses a preparation method of a catalyst for catalyzing glucose dehydration to generate 5-hydroxymethylfurfural. The catalyst is prepared by synthesizing alumina nano-fiber by a hydrothermal method and loading tungsten oxide on the alumina nano-fiber by an isometric impregnation method.
The above patents all refer to heterogeneous catalysts, and the solid-liquid reaction between glucose and the catalyst still has mass transfer problem in the solid-liquid reaction.
At present, the search for a solid catalyst with reusable catalyst, less corrosion and less environmental pollution is very important for the early realization of industrialization of 5-hydroxymethylfurfural.
Disclosure of Invention
The invention aims to provide a preparation method of a solid catalyst for catalyzing glucose dehydration, which is scientific, reasonable, simple and feasible, the prepared solid catalyst for catalyzing glucose dehydration can realize homogeneous reaction of acid released in high-temperature reaction and glucose, and the catalyst can recover the released acid after the reaction is finished.
The preparation method of the solid catalyst for catalyzing glucose dehydration comprises the following steps:
(1) preparation of mesoporous carbon-nitrogen material
Adding chitosan and SBA-15 into water, uniformly mixing, and evaporating water under the condition of heating and stirring to obtain dry solid particles; grinding the solid particles, and roasting in a nitrogen atmosphere to obtain black solid powder; soaking black solid powder in a hydrogen fluoride solution to remove SBA-15, then filtering, cleaning and drying to obtain a mesoporous carbon-nitrogen material;
(2) preparation of solid catalyst for catalyzing dehydration of glucose
And soaking the prepared mesoporous carbon nitrogen material in an acid solution, filtering, cleaning and drying to obtain the solid catalyst for catalyzing glucose dehydration.
The mass ratio of the chitosan to the SBA-15 in the step (1) is 1:0.1-10, and the preferable mass ratio is 1: 1.
the heating temperature in the step (1) is 80-90 ℃.
The roasting temperature in the step (1) is 400-900 ℃, the preferred roasting temperature is 500 ℃, the heating rate is 1-10 ℃/min, and the preferred heating rate is 5 ℃/min.
The mass concentration of the hydrogen fluoride solution in the step (1) is 5-40%, preferably 10 wt%.
The drying temperature in the step (1) is 80-130 ℃, and the drying time is 8-24 hours.
The acidic solution in the step (2) is one of a hydrochloric acid solution, a sulfuric acid solution, a phosphoric acid solution, a phosphotungstic acid solution or a formic acid solution.
The concentration of the acidic solution in the step (2) is 0.1-10 mol/L.
The soaking time in the step (2) is 10-30 h.
The drying temperature in the step (2) is 80-130 ℃, and the drying time is 10-12 hours.
The strong acid with trace concentration has little corrosion to equipment, so the invention constructs a weak alkaline solid and trace inorganic strong acid combined catalytic high-efficiency glucose dehydration system. The invention provides a research idea of utilizing carbon-nitrogen materials to adsorb acid at low temperature and release acid at high temperature for catalytic reaction, and constructs heterogeneous glucose directional conversion guided by an N-doped carbon solid catalyst with multiple catalytic active centers.
According to the invention, chitosan and SBA-15 are used as precursors, a carbon-nitrogen material is prepared after roasting, SBA-15 is removed to adsorb acid to obtain a solid acid catalyst which has temperature response and releases acid and is used for catalyzing glucose dehydration, and then the catalytic effect of the solid acid catalyst is discussed through a catalytic reaction of converting glucose into 5-hydroxymethylfurfural in one step.
The application of the solid catalyst for catalyzing the glucose dehydration prepared by the invention is as follows:
dissolving glucose in water, adding a solid catalyst for catalyzing glucose dehydration into a reaction kettle, carrying out catalytic reaction in an oil bath kettle, and measuring the conversion rate of the glucose and the yield of the 5-hydroxymethylfurfural by using high performance liquid chromatography.
The invention has the following beneficial effects:
the mesoporous carbon-nitrogen material has certain alkalinity, can chemically adsorb acid at low temperature, can release acid to catalyze glucose for dehydration at high temperature, and can recover the acid after the reaction is finished to prepare the solid catalyst for catalyzing glucose, which can release the acid through temperature response.
Drawings
FIG. 1 is a diagram of the catalytic dehydration of glucose to produce 5-HMF of example 1.
FIG. 2 is an infrared image of the catalyst of example 1.
FIG. 3 is example 1CO2TPD measures the alkaline bitmap of the carbon-nitrogen material.
FIG. 4 is a catalyst recycling diagram of example 1.
Detailed Description
The present invention is further described below with reference to examples.
The percentages in the following examples are by weight unless otherwise specified.
Example 1
First, chitosan and SBA-15 were mixed at a ratio of 1: 1 adding the mixture into water, and slowly evaporating water under the condition of stirring at 80 ℃ to obtain solid particles; grinding the solid particles, and roasting at 500 ℃ in a nitrogen atmosphere (the heating rate is 5 ℃/min, and the heat preservation is carried out for 1h) to obtain black solid powder. Soaking black solid powder in 5% HF solution to remove SBA-15, filtering, washing with deionized water for multiple times until hydrofluoric acid is cleaned, and finally drying in an oven at 80 ℃ for 10 hours to obtain the mesoporous carbon nitrogen material. Soaking the prepared carbon and nitrogen material in 5mol/L hydrochloric acid for 24h, filtering, washing with deionized water for multiple times until redundant acid is washed, and finally drying in an oven at 90 ℃ for 12 h to obtain the solid catalyst for catalyzing glucose dehydration.
Analysis and test of catalytic performance:
0.1g of glucose was dissolved in 4ml of water and 8ml of methyl isobutyl ketone, then 0.2g of a solid catalyst for catalyzing dehydration of glucose was added to the reaction vessel, a catalytic reaction was carried out in an oil bath at 160 ℃ for 6.5 hours, and the remaining glucose and the produced 5-hydroxymethylfurfural were measured by high performance liquid chromatography.
The conversion of glucose was determined to be 100% and the yield of 5-hydroxymethylfurfural was determined to be 58.5%.
FIG. 1 is a diagram of the catalytic dehydration of glucose to 5-HMF. As can be seen from the figure, the conversion rate of glucose and the yield of 5-HMF are gradually increased along with the increase of the temperature, the conversion rate of glucose can reach 100% when the reaction time reaches 6h, the yield of 5-HMF reaches the maximum value of 58.5% when the reaction time is 6.5h, and the 5-HMF is unstable and continues to be decomposed in the next step when the reaction temperature is continuously increased.
FIG. 2 is an infrared image of the catalyst. As can be seen from the figure, 3353cm-1In the form of an N-H functional group, 2168cm-1Where is-N ═ C ═ O functional group, 1421 and 1321cm-1The peaks are respectively attributed to C ═ N and N ═ N, and the infrared graph shows that the catalyst has certain alkalinity, and the main source of alkalinity is a functional group containing nitrogen elements.
FIG. 3 is CO2TPD measures the alkaline bitmap of the carbon-nitrogen material. As can be seen from the figure, the carbon-nitrogen material has a certain weak alkaline site and can adsorb CO at low temperature when the absorption peak is wide at 100-200 DEG C2Desorption at high temperatures is possible, which may prove to be feasible in response to temperature in the acid-releasing catalyst.
Fig. 4 is a catalyst recycling map. As can be seen from the figure, the catalyst has good reusability, and the catalyst still has good catalytic effect after being recycled for 4 times. Meanwhile, the carbon and nitrogen material is proved to be capable of effectively recovering the released acid when the acid released at high temperature is reacted.
Example 2
First, chitosan and SBA-15 were mixed at a ratio of 1: 3 adding the mixture into water, and slowly evaporating water under the condition of stirring at 82 ℃ to obtain solid particles; grinding the solid particles, and roasting at 500 ℃ in a nitrogen atmosphere (the heating rate is 2 ℃/min, and the temperature is kept for 1h) to obtain black solid powder. Soaking black solid powder in 8% HF solution to remove SBA-15, filtering, washing with deionized water for multiple times until hydrofluoric acid is cleaned, and finally drying in an oven at 86 ℃ for 15 hours to obtain the mesoporous carbon nitrogen material. Soaking the prepared carbon and nitrogen material in 5mol/L hydrochloric acid for 26h, filtering, washing with deionized water for multiple times until redundant acid is washed, and finally drying in an oven at 80 ℃ for 10 h to obtain the solid catalyst for catalyzing glucose dehydration.
Analysis and test of catalytic performance:
0.1g of glucose was dissolved in 4ml of water and 8ml of methyl isobutyl ketone, then 0.2g of a solid catalyst for catalyzing dehydration of glucose was added to the reaction vessel, a catalytic reaction was carried out in an oil bath at 160 ℃ for 6.5 hours, and the remaining glucose and the produced 5-hydroxymethylfurfural were measured by high performance liquid chromatography.
It was found that the conversion of glucose was 98.8% and the yield of 5-hydroxymethylfurfural was 57.1%.
Example 3
First, chitosan and SBA-15 were mixed at a ratio of 1: 2, after adding into water, slowly evaporating water under the condition of stirring at 85 ℃ to obtain solid particles; grinding the solid particles, and roasting at 400 ℃ in a nitrogen atmosphere (the heating rate is 6 ℃/min, and the heat preservation is carried out for 1h) to obtain black solid powder. Soaking black solid powder in 6% HF solution to remove the SBA-15 template, then filtering, washing with deionized water for multiple times until hydrofluoric acid is cleaned, and finally drying in an oven at 90 ℃ for 18 hours to obtain the mesoporous carbon nitrogen material. Soaking the prepared carbon and nitrogen material in 5mol/L hydrochloric acid for 24h, filtering, washing with deionized water for multiple times until redundant acid is washed, and finally drying in an oven at 100 ℃ for 12 h to obtain the solid catalyst for catalyzing glucose dehydration.
Analysis and test of catalytic performance:
0.1g of glucose was dissolved in 4ml of water and 8ml of methyl isobutyl ketone, then 0.2g of a solid catalyst for catalyzing dehydration of glucose was added to the reaction vessel, a catalytic reaction was carried out in an oil bath at 160 ℃ for 6.5 hours, and the remaining glucose and the produced 5-hydroxymethylfurfural were measured by high performance liquid chromatography.
It was found that the conversion of glucose was 98.5% and the yield of 5-hydroxymethylfurfural was 56.7%.
Example 4
First, chitosan and SBA-15 were mixed at a ratio of 1:0.1 adding into water, slowly evaporating water under stirring at 86 deg.C to obtain solid particles; grinding the solid particles, and roasting at 450 ℃ in a nitrogen atmosphere (the heating rate is 8 ℃/min, and the temperature is kept for 1h) to obtain black solid powder. Soaking black solid powder in 10% HF solution to remove the SBA-15 template, then filtering, washing with deionized water for multiple times until hydrofluoric acid is cleaned, and finally drying in an oven at 90 ℃ for 24 hours to obtain the mesoporous carbon nitrogen material. Soaking the prepared carbon and nitrogen material in 3mol/L hydrochloric acid for 18h, filtering, washing with deionized water for multiple times until redundant acid is washed, and finally drying in an oven at 80 ℃ for 11 h to obtain the solid catalyst for catalyzing glucose dehydration.
Analysis and test of catalytic performance:
0.1g of glucose was dissolved in 4ml of water and 8ml of methyl isobutyl ketone, then 0.2g of a solid catalyst for catalyzing dehydration of glucose was added to the reaction vessel, a catalytic reaction was carried out in an oil bath at 160 ℃ for 6.5 hours, and the remaining glucose and the produced 5-hydroxymethylfurfural were measured by high performance liquid chromatography.
It was found that the conversion of glucose was 90.8% and the yield of 5-hydroxymethylfurfural was 52.1%.
Example 5
First, chitosan and SBA-15 were mixed at a ratio of 1: 1 adding the mixture into water, and slowly evaporating water under the condition of stirring at 80 ℃ to obtain solid particles; grinding the solid particles, and roasting at 900 ℃ in a nitrogen atmosphere (the heating rate is 5 ℃/min, and the temperature is kept for 1h) to obtain black solid powder. Soaking black solid powder in 5% HF solution to remove the SBA-15 template, then filtering, washing with deionized water for multiple times until hydrofluoric acid is cleaned, and finally drying in an oven at 95 ℃ for 12 hours to obtain the mesoporous carbon nitrogen material. Soaking the prepared carbon and nitrogen material in 5mol/L hydrochloric acid for 26h, filtering, washing with deionized water for multiple times until redundant acid is washed, and finally drying in an oven at 130 ℃ for 10 h to obtain the solid catalyst for catalyzing glucose dehydration.
Analysis and test of catalytic performance:
0.1g of glucose was dissolved in 4ml of water and 8ml of methyl isobutyl ketone, then 0.2g of a solid catalyst for catalyzing dehydration of glucose was added to the reaction vessel, a catalytic reaction was carried out in an oil bath at 160 ℃ for 6.5 hours, and the remaining glucose and the produced 5-hydroxymethylfurfural were measured by high performance liquid chromatography.
It was found that the conversion of glucose was 94.3% and the yield of 5-hydroxymethylfurfural was 53.2%.
Example 6
First, chitosan and SBA-15 were mixed at a ratio of 1: 3 adding the mixture into water, and slowly evaporating water under the condition of stirring at 90 ℃ to obtain solid particles; grinding the solid particles, and roasting at 600 ℃ in a nitrogen atmosphere (the heating rate is 3 ℃/min, and the heat preservation is carried out for 1h) to obtain black solid powder. Soaking black solid powder in 7% HF solution to remove SBA-15, filtering, washing with deionized water for multiple times until hydrofluoric acid is cleaned, and finally drying in an oven at 100 ℃ for 16 hours to obtain the mesoporous carbon nitrogen material. Soaking the prepared carbon and nitrogen material in 5mol/L phosphotungstic heteropoly acid for 24h, filtering, washing with deionized water for multiple times until redundant acid is washed, and finally drying in an oven at 100 ℃ for 12 h to obtain the solid catalyst for catalyzing glucose dehydration.
Analysis and test of catalytic performance:
0.1g of glucose was dissolved in 4ml of water and 8ml of methyl isobutyl ketone, then 0.2g of a solid catalyst for catalyzing dehydration of glucose was added to the reaction vessel, a catalytic reaction was carried out in an oil bath at 160 ℃ for 6.5 hours, and the remaining glucose and the produced 5-hydroxymethylfurfural were measured by high performance liquid chromatography.
It was found that the conversion of glucose was 96.1% and the yield of 5-hydroxymethylfurfural was 53.9%.
Example 7
First, chitosan and SBA-15 were mixed at a ratio of 1: 10 adding the mixture into water, and slowly evaporating water under the condition of stirring at 82 ℃ to obtain solid particles; grinding the solid particles, and roasting at 520 ℃ in a nitrogen atmosphere (the heating rate is 9 ℃/min, and the temperature is kept for 1h) to obtain black solid powder. Soaking black solid powder in 9% HF solution to remove SBA-15, filtering, washing with deionized water for multiple times until hydrofluoric acid is cleaned, and finally drying in an oven at 90 ℃ for 9 hours to obtain the mesoporous carbon nitrogen material. Soaking the prepared carbon and nitrogen material in 5mol/L formic acid for 24h, filtering, washing with deionized water for multiple times until redundant acid is washed, and finally drying in an oven at 100 ℃ for 12 h to obtain the solid catalyst for catalyzing glucose dehydration.
Analysis and test of catalytic performance:
0.1g of glucose was dissolved in 4ml of water and 8ml of methyl isobutyl ketone, then 0.2g of a solid catalyst for catalyzing dehydration of glucose was added to the reaction vessel, a catalytic reaction was carried out in an oil bath at 160 ℃ for 6.5 hours, and the remaining glucose and the produced 5-hydroxymethylfurfural were measured by high performance liquid chromatography.
It was found that the conversion of glucose was 88.6% and the yield of 5-hydroxymethylfurfural was 48.7%.
Example 8
First, chitosan and SBA-15 were mixed at a ratio of 1: 0.5 adding into water, slowly evaporating water under stirring at 88 deg.C to obtain solid particles; grinding the solid particles, and roasting at 500 ℃ in a nitrogen atmosphere (the heating rate is 5 ℃/min, and the heat preservation is carried out for 1h) to obtain black solid powder. Soaking black solid powder in 10% HF solution to remove the SBA-15 template, then filtering, washing with deionized water for multiple times until hydrofluoric acid is cleaned, and finally drying in an oven at 100 ℃ for 15 hours to obtain the mesoporous carbon nitrogen material. Soaking the prepared carbon and nitrogen material in 2mol/L hydrochloric acid for 28h, filtering, washing with deionized water for multiple times until redundant acid is washed, and finally drying in an oven at 110 ℃ for 12 h to obtain the solid catalyst for catalyzing glucose dehydration.
Analysis and test of catalytic performance:
0.1g of glucose was dissolved in 4ml of water and 8ml of methyl isobutyl ketone, then 0.2g of a solid catalyst for catalyzing dehydration of glucose was added to the reaction vessel, a catalytic reaction was carried out in an oil bath at 160 ℃ for 6.5 hours, and the remaining glucose and the produced 5-hydroxymethylfurfural were measured by high performance liquid chromatography.
It was found that the conversion of glucose was 96.8% and the yield of 5-hydroxymethylfurfural was 55.7%.
Example 9
First, chitosan and SBA-15 were mixed at a ratio of 1: 1, after adding into water, slowly evaporating water under the condition of stirring at 82 ℃ to obtain solid particles; grinding the solid particles, and roasting at 480 ℃ in a nitrogen atmosphere (the heating rate is 10 ℃/min, and the heat preservation is carried out for 1h) to obtain black solid powder. Soaking black solid powder in 6% HF solution to remove the SBA-15 template, then filtering, washing with deionized water for multiple times until hydrofluoric acid is cleaned, and finally drying in an oven at 100 ℃ for 20 hours to obtain the mesoporous carbon nitrogen material. Soaking the prepared carbon and nitrogen material in 10mol/L hydrochloric acid for 30h, filtering, washing with deionized water for multiple times until redundant acid is washed, and finally drying in an oven at 80 ℃ for 11 h to obtain the solid catalyst for catalyzing glucose dehydration.
Analysis and test of catalytic performance:
0.1g of glucose was dissolved in 4ml of water and 8ml of methyl isobutyl ketone, then 0.2g of a solid catalyst for catalyzing dehydration of glucose was added to the reaction vessel, a catalytic reaction was carried out in an oil bath at 160 ℃ for 6.5 hours, and the remaining glucose and the produced 5-hydroxymethylfurfural were measured by high performance liquid chromatography.
The conversion of glucose was determined to be 100% and the yield of 5-hydroxymethylfurfural was determined to be 56.2%.
Claims (9)
1. A preparation method of a solid catalyst for catalyzing glucose dehydration is characterized by comprising the following steps:
(1) preparation of mesoporous carbon-nitrogen material
Adding chitosan and SBA-15 into water, uniformly mixing, and evaporating water under the condition of heating and stirring to obtain dry solid particles; grinding the solid particles, and roasting in a nitrogen atmosphere to obtain black solid powder; soaking black solid powder in a hydrogen fluoride solution to remove SBA-15, then filtering, cleaning and drying to obtain a mesoporous carbon-nitrogen material;
(2) preparation of solid catalyst for catalyzing dehydration of glucose
Soaking the prepared mesoporous carbon nitrogen material in an acid solution, filtering, cleaning and drying to obtain a solid catalyst for catalyzing glucose dehydration;
the acidic solution in the step (2) is one of a hydrochloric acid solution, a sulfuric acid solution, a phosphoric acid solution, a phosphotungstic acid solution or a formic acid solution.
2. The method for preparing a solid catalyst for catalyzing dehydration of glucose according to claim 1, wherein the mass ratio of chitosan to SBA-15 in step (1) is 1: 0.1-10.
3. The method for preparing a solid catalyst for catalytic dehydration of glucose according to claim 1, characterized in that the heating temperature in step (1) is 80-90 ℃.
4. The method for preparing a solid catalyst for catalyzing dehydration of glucose according to claim 1, wherein the calcination temperature in step (1) is 400-900 ℃.
5. The method for preparing a solid catalyst for catalyzing dehydration of glucose according to claim 1, wherein said hydrogen fluoride solution in step (1) has a mass concentration of 5 to 40%.
6. The method for preparing a solid catalyst for catalytic dehydration of glucose according to claim 1, characterized in that the drying temperature in step (1) is 80-130 ℃ and the drying time is 8-24 hours.
7. The method for preparing a solid catalyst for catalytic dehydration of glucose according to claim 1, characterized in that the concentration of said acidic solution in step (2) is 0.1-10 mol/L.
8. The method for preparing a solid catalyst for catalyzing dehydration of glucose according to claim 1, characterized in that said soaking time in step (2) is 10-30 h.
9. The method for preparing a solid catalyst for catalytic dehydration of glucose according to claim 1, characterized in that the drying temperature in step (2) is 80-130 ℃ and the drying time is 10-12 hours.
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