CN113402485A - Method for preparing 5-hydroxymethylfurfural by converting cellulose in composite molten salt hydrate - Google Patents
Method for preparing 5-hydroxymethylfurfural by converting cellulose in composite molten salt hydrate Download PDFInfo
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- CN113402485A CN113402485A CN202110584017.6A CN202110584017A CN113402485A CN 113402485 A CN113402485 A CN 113402485A CN 202110584017 A CN202110584017 A CN 202110584017A CN 113402485 A CN113402485 A CN 113402485A
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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
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
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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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/122—Halides of copper
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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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
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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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/138—Halogens; Compounds thereof with alkaline earth metals, magnesium, beryllium, zinc, cadmium or mercury
Abstract
The invention belongs to the technical field of biomass resource utilization, and particularly relates to a method for preparing 5-hydroxymethylfurfural by converting cellulose in a composite molten salt hydrate. Firstly, mixing different types of molten salt hydrates according to a certain proportion to prepare a composite molten salt hydrate, then adding cellulose and an organic solvent to perform catalytic reaction under a hydrothermal condition, cooling, taking the organic phase to separate to obtain the 5-hydroxymethylfurfural. The composite molten salt hydrate is used as a catalyst and a reaction solvent, so that cellulose can be dissolved, the composite molten salt hydrate can provide a catalytic activity center required by cellulose conversion, and the cellulose conversion rate and the product yield are improved.
Description
Technical Field
The invention belongs to the technical field of biomass resource utilization, and particularly relates to a method for preparing 5-hydroxymethylfurfural by converting cellulose in a hydrothermal kettle by taking a composite molten salt hydrate as a catalysis and reaction system.
Background
Biomass generally refers to any substance derived from photosynthesis in nature. Cellulose is used as the biomass energy source with the most extensive sources on the earth, and how to convert the cellulose into a platform compound with useful value is very important. 5-hydroxymethylfurfural is a very valuable chemical, an important component of fuel precursors, and some of its derivatives (e.g., dimethylfuran, ethoxymethylfurfural, etc.) have higher energy density and octane number than traditional fossil fuels. Meanwhile, 5-hydroxymethylfurfural can be converted into valuable chemicals such as 1, 6-hexanediol, polyethylene furan acid, 5-hydroxymethyl-2-furan carboxylic acid, 2, 5-furan dicarboxylic acid and the like. The preparation of 5-hydroxymethylfurfural by taking cellulose as a raw material can reduce the dependence on fossil energy and has very important research value and application prospect.
At present, inorganic acid, solid acid, ionic liquid and the like are used as catalysts for preparing 5-hydroxymethylfurfural by cellulose conversion. Inorganic acids can corrode equipment and separate products during the catalysis process; the solid acid catalyst has the problems of difficult dissolution, small contact area, poor catalytic effect and the like; ionic liquid catalysts are generally expensive and difficult to separate. Therefore, the industrial application of these three catalysts is limited.
Chinese patent 201310204142.5 discloses a method for preparing furfural compounds from biomass. According to the method, biomass or derivatives thereof are mixed with a solid acid catalyst, and a two-phase reaction system of an organic solvent and a saturated inorganic salt aqueous solution is utilized to obtain the 5-hydroxymethylfurfural with the yield of 38.5% under mild conditions.
Chinese patent 201710430078.0 discloses a method for preparing 5-hydroxymethylfurfural by catalyzing biomass with metal sulfate. According to the method, biomass and a metal sulfate catalyst are mixed, a two-phase system of water and an organic solvent is used as a reaction solvent under the condition of protective gas, and the biomass is converted into furfural with high yield of 40-80% under mild reaction conditions.
Chinese patent 201811500129.3 discloses a method for preparing 5-hydroxymethylfurfural based on cellulose conversion. The method adopts cellulose as a raw material and transition metal salt as a catalyst, and prepares the 5-hydroxymethylfurfural in an organic solvent-water two-phase system, wherein the yield is 60-80%.
Chinese patent 202011174015.1 discloses a highly efficient method for the preparation and separation of 5-hydroxymethylfurfural from glucose. The method prepares the 5-hydroxymethylfurfural by mixing choline chloride and glucose at a lower temperature, and simultaneously uses inorganic salts as a catalyst, so that the method has good selectivity on the 5-hydroxymethylfurfural.
Chinese patent 202011154848.1 discloses a method for preparing 5-hydroxymethylfurfural by catalyzing cellulose formate with a dimethyl sulfoxide-water cosolvent system. The method comprises the steps of carrying out acidolysis and formylation modification on cellulose at 120 ℃ by using a green recyclable formic acid solution to synthesize cellulose formate, and directly and efficiently catalyzing the cellulose formate to prepare 5-hydroxymethylfurfural in a dimethyl sulfoxide-water cosolvent system by using hydrochloric acid-aluminum chloride as a combined catalyst, wherein the yield is 50%.
Chinese patent 201811425572.9 discloses a process for the preparation of 5-hydroxymethylfurfural from glucose-containing feedstocks. According to the method, inorganic acid and organic solvent are added into mixed liquid of glucose and fructose to be heated for carrying out primary dehydration reaction, so that the conversion from the fructose to 5-hydroxymethylfurfural is completed, then metal chloride is added into the reaction liquid for carrying out secondary dehydration reaction, so that the conversion of the glucose is realized, and the 5-hydroxymethylfurfural generated by the primary dehydration reaction cannot be damaged in the process. The yield of 5-hydroxymethylfurfural through the two-stage dehydration reaction is 14-80%.
Yingxiong Wang et al studied the direct conversion of chitin to 5-hydroxymethylfurfural in aqueous zinc chloride solution as D-glucosamine (GlcNH)2) Being a reaction model compound, GlcNH2The conversion was 99% and the yield of 5-hydroxymethylfurfural was 21.9% (Bioresource Technology 143(2013)384- & lt 390).).
Tiansheng Deng et al have studied the conversion of cellulose to 5-hydroxymethylfurfural in aqueous solutions of zinc chloride. The results show that ZnCl is altered2In concentrations that produce incompletely coordinated Zn2+Ions can be matched with cellulose to catalyze the fructose and further convert the fructose into 5-hydroxymethylfurfural, and the yield of the 5-hydroxymethylfurfural is about 20 percent under mild reaction conditions (chem.Commun.,2012,48, 5494-5496).
Sudipta De et al studied the microwave-assisted conversion of cellulose to 5-hydroxymethylfurfural in a single aqueous system under the catalysis of zinc chloride. The experimental results show that the yield of 5-hydroxymethylfurfural reaches 40% (Green chem.,2011,13, 28-59).
The main obstacles to the direct conversion of cellulose to 5-hydroxymethylfurfural today are: first, cellulose is difficult to dissolve. In addition, the preparation of 5-hydroxymethylfurfural by cellulose conversion involves multiple steps of reactions, each step needs to be catalyzed by using different acids, byproducts such as humins and levulinic acid are easy to generate, and the yield of 5-hydroxymethylfurfural is low.
Disclosure of Invention
The invention aims to provide a method for preparing 5-hydroxymethylfurfural by converting cellulose in a composite molten salt hydrate, which takes the composite molten salt hydrate as a solvent and a catalytic system, and can accelerate the dissolution of the cellulose on the one hand; on the other hand, the catalyst active center required by cellulose conversion can be provided, so that the selectivity and the yield of the 5-hydroxymethylfurfural are improved.
In order to achieve the purpose, the invention provides the following technical scheme:
(1) mixing the two molten salt hydrates according to a certain volume ratio to obtain a composite molten salt hydrate;
(2) mixing the composite molten salt hydrate obtained in the step (1) with a certain mass of cellulose, and adding a certain volume of organic solvent into the composite molten salt hydrate to obtain a two-phase system mixed solution;
(3) and (3) putting the two-phase mixed solution obtained in the step (2) into a hydrothermal kettle, putting the mixture into the hydrothermal kettle and starting stirring when the temperature in an oil bath kettle reaches a certain temperature, carrying out catalytic reaction, and separating and purifying the organic phase after the reaction is finished to obtain the 5-hydroxymethylfurfural.
Further, in the step (1), the volume ratio of the two molten salt hydrates is 1: 1-3, mixing.
Further, the mass ratio of the cellulose to the composite molten salt hydrate in the step (2) is 1: 50-100.
Further, the organic solvent in the step (2) is selected from any one of methyl isobutyl ketone, methyl isopropyl ketone, dimethyl sulfoxide, tetrahydrofuran, hexane and petroleum ether.
Further, the volume ratio of the composite molten salt hydrate to the organic solvent in the step (2) is 1: 0.5-3.
Further, the reaction temperature in the step (3) is 105-140 ℃, and the reaction time is 30-120 min.
The invention has the beneficial effects that:
1. according to the invention, the composite molten salt hydrate is used as the catalyst and the reaction solvent, so that on one hand, the effect of dissolving cellulose is better, and on the other hand, the composite molten salt hydrate can provide a catalytic activity center required by cellulose conversion, so that the synergetic catalysis among different acids is realized, and the yield of 5-hydroxymethylfurfural is further improved.
2. The use of the organic solvent can continuously extract the reaction product and prevent the generation of byproducts;
3. the composite molten salt hydrate is simple to prepare and low in price.
Detailed Description
Example 1:
(1) reacting ZnCl2·3H2O and FeCl3·6H2O two molten salt hydrates according to 3: 1 volume ratio to obtain a composite molten salt hydrate;
(2) mixing 5ml of composite molten salt hydrate with 0.2g of cellulose, and adding 15ml of methyl isobutyl ketone into the composite molten salt hydrate to obtain a two-phase system mixed solution;
(3) and (3) putting the two-phase mixed solution obtained in the step (2) into a hydrothermal kettle, putting the mixture into the hydrothermal kettle when the temperature in an oil bath kettle reaches 110 ℃, starting stirring, carrying out catalytic reaction for 120min, and separating and purifying the organic phase after the reaction is finished to obtain the 5-hydroxymethylfurfural.
According to the high performance liquid chromatography analysis, the yield of the 5-hydroxymethylfurfural is 47.6 percent.
Example 2:
(1) reacting ZnCl2·3H2O and CuCl2·2H2O two molten salt hydrates according to the ratio of 2: 1 volume ratio to obtain a composite molten salt hydrate;
(2) mixing 5ml of composite molten salt hydrate with 0.15g of cellulose, and then adding 5ml of petroleum ether into the composite molten salt hydrate to obtain a two-phase system mixed solution;
(3) and (3) putting the two-phase mixed solution obtained in the step (2) into a hydrothermal kettle, putting the mixture into the hydrothermal kettle when the temperature in an oil bath kettle reaches 120 ℃, starting stirring, carrying out catalytic reaction for 30min, and separating and purifying the organic phase after the reaction is finished to obtain the 5-hydroxymethylfurfural.
The yield of 5-hydroxymethylfurfural was 20.5% according to high performance liquid chromatography analysis.
Example 3:
(1) FeCl is added3·6H2O and CuCl2·2H2O two molten salt hydrates according to 1.5: 1 volume ratio to obtain a composite molten salt hydrate;
(2) mixing 5ml of composite molten salt hydrate with 0.1g of cellulose, and adding 10ml of hexane into the composite molten salt hydrate to obtain a two-phase system mixed solution;
(3) and (3) putting the two-phase mixed solution obtained in the step (2) into a hydrothermal kettle, putting the mixture into the hydrothermal kettle when the temperature in an oil bath kettle reaches 125 ℃, starting stirring, carrying out catalytic reaction for 45min, and separating and purifying the organic phase after the reaction is finished to obtain the 5-hydroxymethylfurfural.
According to the high performance liquid chromatography analysis, the yield of the 5-hydroxymethylfurfural with 27.8 percent is obtained.
Example 4:
(1) reacting ZnCl2·6H2O and CuCl2·2H2O two molten salt hydrates according to 3: 1 volume ratio to obtain a composite molten salt hydrate;
(2) mixing 5ml of composite molten salt hydrate with 0.3g of cellulose, and adding 2.5ml of methyl isopropyl ketone into the composite molten salt hydrate to obtain a two-phase system mixed solution;
(3) and (3) putting the two-phase mixed solution obtained in the step (2) into a hydrothermal kettle, putting the mixture into the hydrothermal kettle when the temperature in an oil bath kettle reaches 115 ℃, starting stirring, carrying out catalytic reaction for 100min, and separating and purifying the organic phase after the reaction is finished to obtain the 5-hydroxymethylfurfural.
According to the high performance liquid chromatography analysis, the yield of the 5-hydroxymethylfurfural is 49.1 percent.
Example 5:
(1) FeCl is added3·6H2O and LiCl3H2O two molten salt hydrates according to the ratio of 2: 1 volume ratio to obtain a composite molten salt hydrate;
(2) mixing 5ml of composite molten salt hydrate with 0.1g of cellulose, and then adding 5ml of tetrahydrofuran into the composite molten salt hydrate to obtain a two-phase system mixed solution;
(3) and (3) putting the two-phase mixed solution obtained in the step (2) into a hydrothermal kettle, putting the mixture into the hydrothermal kettle when the temperature in an oil bath kettle reaches 105 ℃, starting stirring, carrying out catalytic reaction for 120min, and separating and purifying the organic phase after the reaction is finished to obtain the 5-hydroxymethylfurfural.
According to the high performance liquid chromatography analysis, the yield of the 5-hydroxymethylfurfural with 48.2 percent is obtained.
Example 6:
(1) FeCl is added3·6H2O and ZnCl2·6H2O two molten salt hydrates are mixed according to the weight ratio of 1: 1 volume ratio to obtain a composite molten salt hydrate;
(2) mixing 5ml of composite molten salt hydrate with 0.16g of cellulose, and then adding 2.5ml of dimethyl sulfoxide into the composite molten salt hydrate to obtain a two-phase system mixed solution;
(3) and (3) putting the two-phase mixed solution obtained in the step (2) into a hydrothermal kettle, putting the mixture into the hydrothermal kettle when the temperature in an oil bath kettle reaches 135 ℃, starting stirring, carrying out catalytic reaction for 110min, and separating and purifying the organic phase after the reaction is finished to obtain the 5-hydroxymethylfurfural.
According to the high performance liquid chromatography analysis, the yield of the 5-hydroxymethylfurfural is 53.4 percent.
Example 7:
(1) LiCl.3H2O and CuCl2·2H2O two molten salt hydrates according to 3: 1 volume ratio to obtain a composite molten salt hydrate;
(2) mixing 5ml of composite molten salt hydrate with 0.1g of cellulose, and then adding 5ml of dimethyl sulfoxide into the composite molten salt hydrate to obtain a two-phase system mixed solution;
(3) and (3) putting the two-phase mixed solution obtained in the step (2) into a hydrothermal kettle, putting the mixture into the hydrothermal kettle when the temperature in an oil bath kettle reaches 130 ℃, starting stirring, carrying out catalytic reaction for 90min, and separating and purifying the organic phase after the reaction is finished to obtain the 5-hydroxymethylfurfural.
According to the high performance liquid chromatography analysis, the yield of the 5-hydroxymethylfurfural is 44.7 percent.
Example 8:
(1) LiCl.3H2O and ZnCl2·3H2O two molten salt hydrates are mixed according to the weight ratio of 1: 1 volume ratio to obtain a composite molten salt hydrate;
(2) mixing 5ml of composite molten salt hydrate with 0.18g of cellulose, and adding 7.5ml of methyl isobutyl ketone into the composite molten salt hydrate to obtain a two-phase system mixed solution;
(3) and (3) putting the two-phase mixed solution obtained in the step (2) into a hydrothermal kettle, putting the mixture into the hydrothermal kettle when the temperature in an oil bath kettle reaches 140 ℃, starting stirring, carrying out catalytic reaction for 70min, and separating and purifying the organic phase after the reaction is finished to obtain the 5-hydroxymethylfurfural.
The yield of 5-hydroxymethylfurfural was 33.2% according to high performance liquid chromatography analysis.
The analysis result of the invention for preparing 5-hydroxymethylfurfural by conversion in the composite molten salt hydrate is shown in table 1.
TABLE 1
Claims (7)
1. A method for preparing 5-hydroxymethylfurfural by converting cellulose in a composite molten salt hydrate is characterized by comprising the following steps:
mixing the two molten salt hydrates according to a certain volume ratio to obtain a composite molten salt hydrate;
mixing the composite molten salt hydrate obtained in the step (1) with a certain mass of cellulose, and adding a certain volume of organic solvent into the composite molten salt hydrate to obtain a two-phase system mixed solution;
and (3) putting the two-phase mixed solution obtained in the step (2) into a hydrothermal kettle, putting the mixture into the hydrothermal kettle and starting stirring when the temperature in an oil bath kettle reaches a certain temperature, carrying out catalytic reaction, and separating and purifying the organic phase after the reaction is finished to obtain the 5-hydroxymethylfurfural.
2. The method for preparing 5-hydroxymethylfurfural by converting cellulose in the composite molten salt hydrate as claimed in claim 1, wherein the two molten salt hydrates can be ZnCl2·3H2O、ZnCl2·6H2O、FeCl3·6H2O、CuCl2·2H2O、LiCl·3H2Two or more of O.
3. The method for preparing 5-hydroxymethylfurfural by converting cellulose in the composite molten salt hydrate as claimed in claim 1, wherein the volume ratio of the two molten salt hydrates is 1: 1-3.
4. The method for preparing 5-hydroxymethylfurfural by converting cellulose in the composite molten salt hydrate as claimed in claim 1, wherein the mass ratio of the cellulose to the molten salt hydrate is 1: 50-100.
5. The method for preparing 5-hydroxymethylfurfural by conversion of cellulose in the composite molten salt hydrate as claimed in claim 1, wherein the organic solvent is one or more of methyl isobutyl ketone, methyl isopropyl ketone, dimethyl sulfoxide, tetrahydrofuran, hexane and petroleum ether.
6. The method for preparing 5-hydroxymethylfurfural by conversion of cellulose in the complex molten salt hydrate as claimed in claim 1, wherein the volume ratio of the complex molten salt hydrate to the organic solvent is 1: 0.5-3.
7. The method for preparing 5-hydroxymethylfurfural by converting cellulose in the composite molten salt hydrate as claimed in claim 1, characterized in that the reaction temperature is 105-140 ℃ and the reaction time is 30-120 min.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114621358A (en) * | 2022-04-14 | 2022-06-14 | 中国科学院青岛生物能源与过程研究所 | Method for preparing cellulose ether with low crystallinity and high substitution degree by adopting one-pot method |
| CN115677630A (en) * | 2022-12-05 | 2023-02-03 | 盱眙凹土能源环保材料研发中心 | Method for preparing furfural and 5-hydroxymethyl furfural from straw |
| CN115745925A (en) * | 2022-12-05 | 2023-03-07 | 华南农业大学 | Method for preparing 5-hydroxymethylfurfural by two-step hydrolysis catalysis of corn straw conversion |
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2021
- 2021-05-27 CN CN202110584017.6A patent/CN113402485A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114621358A (en) * | 2022-04-14 | 2022-06-14 | 中国科学院青岛生物能源与过程研究所 | Method for preparing cellulose ether with low crystallinity and high substitution degree by adopting one-pot method |
| CN114621358B (en) * | 2022-04-14 | 2022-12-30 | 中国科学院青岛生物能源与过程研究所 | Method for preparing cellulose ether with low crystallinity and high substitution degree by adopting one-pot method |
| CN115677630A (en) * | 2022-12-05 | 2023-02-03 | 盱眙凹土能源环保材料研发中心 | Method for preparing furfural and 5-hydroxymethyl furfural from straw |
| CN115745925A (en) * | 2022-12-05 | 2023-03-07 | 华南农业大学 | Method for preparing 5-hydroxymethylfurfural by two-step hydrolysis catalysis of corn straw conversion |
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