CN115141164B - Preparation method of 5-hydroxymethylfurfural - Google Patents
Preparation method of 5-hydroxymethylfurfural Download PDFInfo
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- CN115141164B CN115141164B CN202210826548.6A CN202210826548A CN115141164B CN 115141164 B CN115141164 B CN 115141164B CN 202210826548 A CN202210826548 A CN 202210826548A CN 115141164 B CN115141164 B CN 115141164B
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- hydroxymethylfurfural
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- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 title claims abstract description 32
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- 239000002028 Biomass Substances 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 150000001720 carbohydrates Chemical class 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 13
- 230000003647 oxidation Effects 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 10
- 230000035484 reaction time Effects 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 239000007789 gas Substances 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 8
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 8
- 229930091371 Fructose Natural products 0.000 claims description 6
- 239000005715 Fructose Substances 0.000 claims description 6
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 4
- 239000003570 air Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000011161 development Methods 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000003912 environmental pollution Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- PJVXUVWGSCCGHT-ZPYZYFCMSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(3s,4r,5r)-1,3,4,5,6-pentahydroxyhexan-2-one Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO PJVXUVWGSCCGHT-ZPYZYFCMSA-N 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- -1 and more preferably Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010812 external standard method Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
Abstract
The invention relates to the fields of catalytic chemistry and biomass resource utilization, in particular to a preparation method of 5-hydroxymethylfurfural. The preparation method comprises the steps of adding saccharide biomass, a solvent and an oxidation catalyst into a reaction kettle for chemical reaction, wherein the reaction temperature is 90-200 ℃, and the reaction time is 10-600 min, so as to obtain the 5-hydroxymethylfurfural. The raw materials, the solvent and the catalyst are all green and environment-friendly, the obtained reaction solution is green and environment-friendly, the reaction solution can be used for subsequent derivative development after simple impurity removal, and the preparation method has the characteristics of simple process, environment-friendly and environment-friendly, stable production, low investment and the like, and provides a new technical route for industrialized low-cost green and environment-friendly production of 5-hydroxymethylfurfural.
Description
Technical Field
The invention relates to the fields of catalytic chemistry and biomass resource utilization, in particular to a preparation method of 5-hydroxymethylfurfural.
Background
Due to the growing shortage of traditional petrochemical resources and environmental pollution problems, people aim at biomass materials gradually so as to prepare chemical raw materials capable of replacing the traditional petrochemical resources. Among them, 5-Hydroxymethylfurfural (HMF) is expected to be an important intermediate compound connecting biomass and chemical raw materials, and 5-hydroxymethylfurfural can be synthesized into a series of other novel furan derivatives with high added value through chemical actions such as hydrogenation, oxidation, esterification and the like, and is finally applied to various aspects such as medical intermediates, synthetic plastics, synthetic rubber, pesticides, surfactants and the like.
At present, the 5-hydroxymethylfurfural is mainly prepared by acid catalytic dehydration, however, common acids in the preparation method are sulfuric acid, hydrochloric acid and the like, the acids have large corrosion to equipment, and the reaction liquid has serious environmental pollution; after that, various solid acid resins are developed to replace acid, but the preparation method is still limited by high cost of the catalyst required by the preparation method and serious environmental pollution of reaction liquid, so that the realization of large-scale production of 5-hydroxymethylfurfural still faces great challenges.
In view of the above, the present invention provides a method for preparing 5-hydroxymethylfurfural, which aims at overcoming the shortcomings of the prior art.
Disclosure of Invention
(1) Technical problem to be solved
The invention aims to provide a preparation method of 5-hydroxymethylfurfural, which aims to solve the problems of severe requirements on equipment, poor environmental protection and high production cost in the production of 5-hydroxymethylfurfural.
(2) Technical proposal
In order to solve the problems, the invention provides a preparation method of 5-hydroxymethylfurfural, which specifically comprises the following steps:
Adding saccharide biomass, a solvent and an oxidation catalyst into a reaction kettle for chemical reaction, wherein the reaction temperature is 90-200 ℃, and the reaction time is 10-600 min, so as to obtain the 5-hydroxymethylfurfural.
Preferably, the oxidation catalyst is at least one of oxygen-containing gas and sodium hypochlorite.
Preferably, the saccharide biomass is at least one of glucose, fructose, sucrose, maltose and fructose-glucose syrup.
Preferably, the solvent is at least one of water, methanol, and ethanol.
Preferably, the mass ratio of the saccharide biomass to the solvent is 1:0.3 to 100.
Preferably, the mass ratio of the saccharide biomass to the catalyst is 5-150: 1.
Preferably, the reaction temperature is 120 ℃ to 160 ℃.
Preferably, the reaction time is 10min to 240min.
Preferably, the oxygen-containing gas in the oxidation catalyst is a mixed gas of air, oxygen and inert gas or a mixed gas of oxygen and CO 2.
Preferably, the concentration of the sodium hypochlorite solution is 4-10wt%.
(3) Advantageous effects
In summary, the technical scheme of the invention has the following advantages:
The method adopts the oxidation catalyst oxygen-containing gas or sodium hypochlorite to directly oxidize biomass to prepare HMF, adds the saccharide biomass, the solvent and the oxidation catalyst into a reaction kettle, and carries out chemical reaction at the set reaction temperature and time to obtain the HMF. The raw materials, the solvent and the catalyst are all green and environment-friendly, the obtained reaction solution is green and environment-friendly, the reaction solution can be used for subsequent derivative development after simple impurity removal, and the preparation method has the characteristics of simple process, environment-friendly and environment-friendly, stable production, low investment and the like, and provides a new technical route for industrialized low-cost green and environment-friendly production of 5-hydroxymethylfurfural.
Detailed Description
Embodiments of the present invention are described in further detail below with reference to examples. The following detailed description of the embodiments is provided to illustrate the principles of the invention and is not intended to limit the scope of the invention, i.e., the invention is not limited to the embodiments described.
In order that the above objects, features and advantages of the invention will be more clearly understood, a further description of the invention will be made. It should be noted that, without conflict, the embodiments of the present invention and features in the embodiments may be combined with each other.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced otherwise than as described herein; it will be apparent that the embodiments in the specification are only some, but not all, embodiments of the invention.
Preferred embodiments of the present invention will be described in detail below with reference to examples. It is to be understood that the following examples are given for illustrative purposes only and are not intended to limit the scope of the present invention. Various modifications and alterations of this invention may be made by those skilled in the art without departing from the spirit and scope of this invention.
The invention provides a preparation method of 5-hydroxymethylfurfural, which specifically comprises the following steps:
Adding saccharide biomass, a solvent and an oxidation catalyst into a reaction kettle for chemical reaction, wherein the reaction temperature is 90-200 ℃, and the reaction time is 10-600 min, so as to obtain the 5-hydroxymethylfurfural.
Preferably, the reaction temperature is 140 ℃ or 150 ℃, and the reaction time is 60min.
Preferably, the oxidation catalyst is at least one of oxygen-containing gas and sodium hypochlorite. More preferably, the oxygen-containing gas may be a mixed gas of air, oxygen and inert gas, and of course, may be a mixed gas of oxygen and CO 2.
More preferably, the inert gas is nitrogen.
In order to achieve better effect of catalytic oxidation reaction, the concentration of the sodium hypochlorite solution is 4-10wt%.
Preferably, the saccharide biomass is at least one of glucose, fructose, sucrose, maltose and fructose-glucose syrup, and more preferably, the saccharide biomass is fructose.
Preferably, the solvent is at least one of water, methanol, ethanol, and more preferably, the solvent is water.
Preferably, the mass ratio of the saccharide biomass to the solvent is 1:0.3 to 100.
Preferably, the mass ratio of the saccharide biomass to the catalyst is 5-150: 1.
Preferably, the reaction temperature is 120 ℃ to 160 ℃.
Preferably, the reaction time is 10min to 240min.
The experimental methods used in the following examples are conventional methods unless otherwise specified.
Materials, reagents and the like used in the examples described below are commercially available unless otherwise specified.
In the embodiment of the invention, 5-hydroxymethylfurfural is detected by Waters 2695 and 2489 liquid chromatograph, and is quantified by an external standard method.
The yield of 5-Hydroxymethylfurfural (HMF) was calculated based on its molecular mole number according to the following formula:
Example 1
6G of fructose and 20g of water are weighed into a 50ml high-pressure reaction kettle liner, the high-pressure reaction kettle is closed, the pressure of the mixed gas of oxygen and nitrogen in the system is kept to be 2mpa, and the reaction is carried out for 60min at 150 ℃. After the reaction is finished, the reaction kettle is cooled to room temperature, and substances in the high-pressure reaction kettle are detected and analyzed, so that the yield of the 5-hydroxymethylfurfural is 30%.
Example 2
6G of fructose, 20g of water and 4g of 8wt% sodium hypochlorite are weighed into a 50ml high-pressure reaction kettle liner, the high-pressure reaction kettle is closed, the pressure of the mixed gas of oxygen and carbon dioxide in the system is kept to be 2mpa, and the reaction is carried out for 60min at 140 ℃. After the reaction is finished, the reaction kettle is cooled to room temperature, and substances in the high-pressure reaction kettle are detected and analyzed, so that the yield of the 5-hydroxymethylfurfural is 15%.
It is to be understood that this invention is not limited to the particular steps and structures described above. Also, a detailed description of known method techniques is omitted here for the sake of brevity.
The above description is only an example of the present application and is not limited to the present application. Various modifications and alterations of this application will become apparent to those skilled in the art without departing from the scope of this application. Any modification, equivalent replacement, improvement, etc. which come within the spirit and principles of the application are to be included in the scope of the claims of the present application.
Claims (5)
1. A preparation method of 5-hydroxymethylfurfural is characterized by comprising the following steps: adding saccharide biomass, a solvent and an oxidation catalyst into a reaction kettle for chemical reaction, wherein the reaction temperature is 90-140 ℃, and the reaction time is 10 min-600 min, so as to obtain the 5-hydroxymethylfurfural;
The oxidation catalyst is at least one of oxygen-containing gas and sodium hypochlorite, and the oxygen-containing gas in the oxidation catalyst is a mixed gas of air, oxygen and inert gas or a mixed gas of oxygen and CO 2;
the saccharide biomass is fructose, and the mass ratio of the saccharide biomass to the catalyst is 5-150: 1, a step of;
the solvent is at least one of water, methanol and ethanol.
2. The method for preparing 5-hydroxymethylfurfural according to claim 1, wherein: the mass ratio of the saccharide biomass to the solvent is 1:0.3 to 100.
3. The method for preparing 5-hydroxymethylfurfural according to claim 1, wherein: the reaction temperature is 120-140 ℃.
4. The method for preparing 5-hydroxymethylfurfural according to claim 1, wherein: the reaction time is 10 min-240 min.
5. The method for preparing 5-hydroxymethylfurfural according to claim 1, wherein: the concentration of the sodium hypochlorite solution is 4-wt wt%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210826548.6A CN115141164B (en) | 2022-07-14 | 2022-07-14 | Preparation method of 5-hydroxymethylfurfural |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210826548.6A CN115141164B (en) | 2022-07-14 | 2022-07-14 | Preparation method of 5-hydroxymethylfurfural |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115141164A CN115141164A (en) | 2022-10-04 |
| CN115141164B true CN115141164B (en) | 2024-05-17 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202210826548.6A Active CN115141164B (en) | 2022-07-14 | 2022-07-14 | Preparation method of 5-hydroxymethylfurfural |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2197865A2 (en) * | 2007-09-07 | 2010-06-23 | Furanix Technologies B.V | Hydroxymethylfurfural ethers from hmf and olefins |
| CN102702144A (en) * | 2012-06-15 | 2012-10-03 | 复旦大学 | Method for preparing furan or furfural compound from biomass cellulose |
| CN103183653A (en) * | 2011-12-29 | 2013-07-03 | 广西科学院 | Green method for preparation of 5-hydroxymethylfurfural |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9162998B2 (en) * | 2011-12-13 | 2015-10-20 | Basf Se | Preparation of 5-hydroxymethylfurfural (HMF) from saccharide solutions in the presence of a solvent having a boiling point greater than 60° C. and less than 200° C. (at standard pressure, called low boiler for short) |
-
2022
- 2022-07-14 CN CN202210826548.6A patent/CN115141164B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2197865A2 (en) * | 2007-09-07 | 2010-06-23 | Furanix Technologies B.V | Hydroxymethylfurfural ethers from hmf and olefins |
| CN103183653A (en) * | 2011-12-29 | 2013-07-03 | 广西科学院 | Green method for preparation of 5-hydroxymethylfurfural |
| CN102702144A (en) * | 2012-06-15 | 2012-10-03 | 复旦大学 | Method for preparing furan or furfural compound from biomass cellulose |
Non-Patent Citations (2)
| Title |
|---|
| Glucose Conversion into 5-Hydroxymethylfurfural over Niobium Oxides Supported on Natural Rubber-Derived Carbon/Silica Nanocomposite;Rujeeluk Khumho et al.;Catalysts;第11卷;887 * |
| 铌类固体酸催化糖转化5－羟甲基糠醛研究进展;杨凤丽 等;现代化工;第38卷(第9期);28-32 * |
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| CN115141164A (en) | 2022-10-04 |
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