CN110229124B - Catalytic system for efficiently preparing 5-hydroxymethylfurfural and application thereof - Google Patents
Catalytic system for efficiently preparing 5-hydroxymethylfurfural and application thereof Download PDFInfo
- Publication number
- CN110229124B CN110229124B CN201910450609.1A CN201910450609A CN110229124B CN 110229124 B CN110229124 B CN 110229124B CN 201910450609 A CN201910450609 A CN 201910450609A CN 110229124 B CN110229124 B CN 110229124B
- Authority
- CN
- China
- Prior art keywords
- hydroxymethylfurfural
- catalytic system
- reaction
- yield
- application
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 title claims abstract description 34
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 230000003197 catalytic effect Effects 0.000 title abstract description 35
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052751 metal Inorganic materials 0.000 claims abstract description 9
- 239000002184 metal Substances 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000002028 Biomass Substances 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 8
- 229930091371 Fructose Natural products 0.000 claims description 7
- 239000005715 Fructose Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- MEYVLGVRTYSQHI-UHFFFAOYSA-L cobalt(2+) sulfate heptahydrate Chemical group O.O.O.O.O.O.O.[Co+2].[O-]S([O-])(=O)=O MEYVLGVRTYSQHI-UHFFFAOYSA-L 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- BJHIKXHVCXFQLS-UYFOZJQFSA-N fructose group Chemical group OCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 claims 1
- 239000000706 filtrate Substances 0.000 abstract description 5
- 239000007788 liquid Substances 0.000 abstract description 4
- 238000011049 filling Methods 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 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 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 229920001202 Inulin Polymers 0.000 description 3
- 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 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 3
- 229940029339 inulin Drugs 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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
- GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 description 2
- POTRNMJIMIESGR-UHFFFAOYSA-L cobalt(2+);diacetate;hexahydrate Chemical compound O.O.O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O POTRNMJIMIESGR-UHFFFAOYSA-L 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- RRIWRJBSCGCBID-UHFFFAOYSA-L nickel sulfate hexahydrate Chemical compound O.O.O.O.O.O.[Ni+2].[O-]S([O-])(=O)=O RRIWRJBSCGCBID-UHFFFAOYSA-L 0.000 description 2
- 229940116202 nickel sulfate hexahydrate Drugs 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- RZLVQBNCHSJZPX-UHFFFAOYSA-L zinc sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Zn+2].[O-]S([O-])(=O)=O RZLVQBNCHSJZPX-UHFFFAOYSA-L 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 1
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- -1 lanthanum sulfate hexahydrate Chemical compound 0.000 description 1
- HDFVHNGCHRTSJC-UHFFFAOYSA-H lanthanum(3+);trisulfate;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[La+3].[La+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O HDFVHNGCHRTSJC-UHFFFAOYSA-H 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
The invention relates to a catalytic system for efficiently preparing 5-hydroxymethylfurfural and application thereof. The catalytic system is obtained by fully and uniformly mixing biomass derivatives, metal salts and organic or inorganic liquid, and filling nitrogen with certain pressure into the catalytic system. The catalytic system is filtered after a certain time of reaction at a high temperature, and the filtrate is distilled under reduced pressure to obtain the 5-hydroxymethylfurfural with the yield of 35-88%. The invention has low cost, simple operation, easy purification of the product and high yield, and has the prospect of industrial production.
Description
Technical Field
The invention relates to a catalytic system for efficiently preparing 5-hydroxymethylfurfural and application thereof, belonging to the field of organic synthesis.
Background
5-hydroxymethylfurfural is a very important fine chemical and pharmaceutical intermediate, and can be used as a drug for effectively preventing and treating neurodegenerative diseases, cognitive impairment and cardiovascular diseases of myocardial ischemia. It derives from the catalytic conversion of the sugar, the largest component of biomass derivatives in nature. The raw materials are cheap and easy to obtain, the reaction is simple, and the method has the potential of large-scale industrialization. However, there are three problems with sugars in the catalytic conversion to 5-hydroxymethylfurfural: firstly, the catalyst has too high acidity or too strong activity so that side reactions such as polymerization reaction or decomposition reaction and the like occur vigorously, thereby leading to lower yield of the 5-hydroxymethylfurfural; secondly, the generated 5-hydroxymethyl furfural cannot exist stably in the existing catalytic system, and can generate irreversible byproducts with a solvent or generate excessive decomposition reaction with the solvent to reduce the yield; thirdly, the separation and purification process of the 5-hydroxymethylfurfural from the existing catalytic system, especially the catalytic system containing high boiling point solvent, is complex, and the production cost is increased. CN103113329B discloses a method for preparing 5-hydroxymethylfurfural by catalyzing saccharides with solid superacid, and the obtained 5-hydroxymethylfurfural has 40-60% of yield. CN106810517a discloses a method for continuously synthesizing 5-hydroxymethylfurfural, which uses a metal salt with weak acidity to inhibit side reactions, but has strong interaction between ionic liquid serving as a solvent and 5-hydroxymethylfurfural to separate products, so that an additional extractant is required, and the cost for separating the 5-hydroxymethylfurfural from the extractant is increased.
The problems are caused by the fact that the catalyst, the solvent and the reaction raw materials in the catalytic system do not play a synergistic effect, and the invention relates to a catalytic system for efficiently preparing 5-hydroxymethylfurfural.
Disclosure of Invention
Aiming at the conditions that the yield of the 5-hydroxymethylfurfural is low and the large-scale production is difficult at present, the invention provides a catalytic system for efficiently preparing the 5-hydroxymethylfurfural.
In order to achieve the above purpose, the invention adopts the following technical scheme: a catalyst system for preparing 5-hydroxymethyl furfural by mutual synergistic action of catalyst, solvent and raw materials under nitrogen atmosphere is prepared from cellulose, inulin, sucrose, fructose or glucose as raw materials, organic or inorganic liquid as solvent, metal salt as catalyst, filling nitrogen gas into a closed reactor, taking out after a certain time at high temperature, filtering to obtain output, and vacuum distilling the filtrate to obtain 5-hydroxymethyl furfural.
A catalytic system for preparing high-yield 5-hydroxymethylfurfural is characterized by comprising biomass derivatives, metal salts, organic or inorganic liquid and gas with a certain pressure.
The preparation method of the catalytic system comprises the following steps: after biomass derivative, metal salt and organic or inorganic liquid are fully and uniformly mixed, nitrogen with certain pressure is filled into a catalytic system.
The metal salt in the catalyst system is one or more of cobalt acetate hexahydrate, cobalt chloride hexahydrate and cobalt sulfate heptahydrate;
the solvent in the catalyst system is one or more of dimethyl sulfoxide, tetrahydrofuran, furfural, acetone and water;
the biomass derivative in the catalyst system is one or more of cellulose, inulin, sucrose, glucose and fructose;
the catalyst in the catalyst system may be replaced by one or more of nickel sulfate hexahydrate, zinc sulfate heptahydrate, lanthanum sulfate nonahydrate.
The mass fraction of the catalyst in the catalytic system is 0.15% -15%.
The mass fraction of the raw materials in the catalytic system is 2% -10%.
The reaction conditions required for the catalyst system are: the reaction temperature is 150-200 ℃, the pressure of nitrogen gas is 2-5 MPa, and the reaction time is 1-4 h.
Drawings
FIG. 1 is the yield of 5-hydroxymethylfurfural of examples and comparative examples of the present invention.
Detailed Description
Comparative example
The comparative catalyst system of the present invention was prepared according to the following steps: after 6.3 g fructose, 2.5 g cobalt sulfate and 36.0g tetrahydrofuran were thoroughly mixed, 3 MPa of nitrogen was introduced. The catalytic system of this example was placed in a heating mantle and reacted at 170℃with 4h. After the reaction was completed, the reaction solution was cooled to room temperature, and the yield of 5-hydroxymethylfurfural was 3.7% by filtration.
Example 1
The catalytic system of the embodiment of the invention is prepared according to the following steps: 1.9 g cellulose, 6.3 g cobalt acetate hexahydrate, 30.0 g water and 6.0g dimethyl sulfoxide are put into a 70mL stainless steel reaction kettle to be fully and uniformly mixed, and then nitrogen with the pressure of 4.5 MPa is filled. The catalytic system of this example was placed in a heating mantle and reacted at 200℃with 4h. After the reaction was completed, the reaction solution was cooled to room temperature, and the yield of 5-hydroxymethylfurfural was measured to be 35.5%.
Example 2
The catalytic system of the embodiment of the invention is prepared according to the following steps: after 6.3 g fructose, 4.0 g cobalt sulfate heptahydrate and 36.0g tetrahydrofuran were thoroughly mixed, 4 MPa of nitrogen gas was introduced. The catalytic system of this example was placed in a heating mantle and reacted at 170℃with 2 h. After the reaction is completed, cooling the reaction solution to room temperature, filtering to obtain 88.0 percent of 5-hydroxymethylfurfural yield, and distilling the filtrate under reduced pressure to obtain yellow 5-hydroxymethylfurfural.
Example 3
The catalytic system of the embodiment of the invention is prepared according to the following steps: 4.1 g g glucose, 3.5g cobalt chloride hexahydrate and 36.0g dimethyl sulfoxide were put into a 70mL stainless steel reaction vessel, and after thoroughly mixing, 2MPa of nitrogen gas was introduced. The catalytic system of this example was placed in a heating mantle and reacted at 180℃3 h. After the reaction was completed, the reaction solution was cooled to room temperature, and the yield of 5-hydroxymethylfurfural was found to be 65.7%.
Example 4
The catalytic system of the embodiment of the invention is prepared according to the following steps: 3.5g sucrose, 4.0 g zinc sulfate heptahydrate and 36.0g furfural are put into a 70mL stainless steel reaction kettle to be fully and uniformly mixed, and then 3 MPa of nitrogen is filled. The catalytic system of this example was placed in a heating mantle and reacted at 140℃2 h. After the reaction was completed, the reaction solution was cooled to room temperature, and the yield of 5-hydroxymethylfurfural was 45.9%.
Example 5
The catalytic system of the embodiment of the invention is prepared according to the following steps: 6.3 g inulin, 4.0 g lanthanum sulfate hexahydrate and 36.0g acetone are put into a 70mL stainless steel reaction kettle to be fully and uniformly mixed, and then 5MPa of nitrogen gas is filled. The catalytic system of this example was placed in a heating mantle and reacted at 190℃with 4h. After the reaction is completed, cooling the reaction solution to room temperature, filtering to obtain 55.9 percent of 5-hydroxymethylfurfural yield, and distilling the filtrate under reduced pressure to obtain yellow 5-hydroxymethylfurfural.
Example 6
The catalytic system of the embodiment of the invention is prepared according to the following steps: 6.3 g fructose, 4.0 g nickel sulfate hexahydrate and 36.0g tetrahydrofuran are put into a 70mL stainless steel reaction kettle to be fully and uniformly mixed, and then 3 MPa of nitrogen is filled. The catalytic system of this example was placed in a heating mantle and reacted at 150℃to 0.5. 0.5 h. After the reaction is completed, cooling the reaction solution to room temperature, filtering to obtain the yield of the 5-hydroxymethylfurfural of 79.0%, and distilling the filtrate under reduced pressure to obtain the yellow 5-hydroxymethylfurfural.
Example 7
The catalytic system of the embodiment of the invention is prepared according to the following steps: after 6.3 g fructose, 4.0 g cobalt sulfate heptahydrate and 36.0g water were thoroughly mixed, 1 MPa nitrogen gas was introduced. The catalytic system of this example was placed in a heating mantle and reacted at 170℃with 4h. After the reaction was completed, the reaction solution was cooled to room temperature, and the yield of 5-hydroxymethylfurfural was 1.0%.
Of course, the above description is not limited to the above examples, and the technical features of the present invention that are not described may be implemented by or by using the prior art, which is not described herein again; the above examples and drawings are only for illustrating the technical scheme of the present invention and not for limiting the same, and the present invention has been described in detail with reference to the preferred embodiments, and it should be understood by those skilled in the art that changes, modifications, additions or substitutions made by those skilled in the art without departing from the spirit of the present invention and the scope of the appended claims.
Claims (2)
1. A method for preparing 5-hydroxymethylfurfural is characterized in that biomass derivatives, metal salt catalysts and solvents are fully and uniformly mixed, and nitrogen with certain pressure is filled into a reaction system; the metal salt catalyst is selected from cobalt sulfate heptahydrate; the solvent is tetrahydrofuran; the biomass derivative is fructose; the reaction temperature is 100-200 ℃, the pressure of the nitrogen gas is 1-5 MPa, and the reaction time is 0.5-4 h; the mass fraction of the metal salt catalyst in the reaction system is 0.15% -15%; the mass fraction of the biomass in the reaction system is 2% -10%.
2. The method according to claim 1, wherein the reaction temperature is 150 to 200 ℃, the pressure of the nitrogen gas is 2 to 5MPa, and the reaction time is 1 to 4 hours.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910450609.1A CN110229124B (en) | 2019-05-28 | 2019-05-28 | Catalytic system for efficiently preparing 5-hydroxymethylfurfural and application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910450609.1A CN110229124B (en) | 2019-05-28 | 2019-05-28 | Catalytic system for efficiently preparing 5-hydroxymethylfurfural and application thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110229124A CN110229124A (en) | 2019-09-13 |
CN110229124B true CN110229124B (en) | 2024-01-02 |
Family
ID=67858578
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910450609.1A Active CN110229124B (en) | 2019-05-28 | 2019-05-28 | Catalytic system for efficiently preparing 5-hydroxymethylfurfural and application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110229124B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113398879A (en) * | 2021-05-18 | 2021-09-17 | 济南大学 | Method for preparing cobalt-based composite material by using biomass and diatomite |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101475543A (en) * | 2009-02-11 | 2009-07-08 | 中国科学院山西煤炭化学研究所 | Method for preparing hydroxymethyl-furfural from glucide under low temperature and normal pressure |
KR20100121080A (en) * | 2009-05-08 | 2010-11-17 | 동아대학교 산학협력단 | Production process of 5-hydroxymethyl-2-furaldehyde from raw biomass using the same |
CN105906588A (en) * | 2016-05-13 | 2016-08-31 | 中盐安徽红四方股份有限公司 | Method for preparing 5-hydroxymethyl furfural from sugar |
-
2019
- 2019-05-28 CN CN201910450609.1A patent/CN110229124B/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101475543A (en) * | 2009-02-11 | 2009-07-08 | 中国科学院山西煤炭化学研究所 | Method for preparing hydroxymethyl-furfural from glucide under low temperature and normal pressure |
KR20100121080A (en) * | 2009-05-08 | 2010-11-17 | 동아대학교 산학협력단 | Production process of 5-hydroxymethyl-2-furaldehyde from raw biomass using the same |
CN105906588A (en) * | 2016-05-13 | 2016-08-31 | 中盐安徽红四方股份有限公司 | Method for preparing 5-hydroxymethyl furfural from sugar |
Non-Patent Citations (1)
Title |
---|
生物油基小分子在催化反应中聚合反应机制研究;孙恺;《中国博士学位论文全文数据库 工程科技I辑》(第03期);1-148 * |
Also Published As
Publication number | Publication date |
---|---|
CN110229124A (en) | 2019-09-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104557801B (en) | Method for preparing gamma-valerolactone from furfural on metal/solid acid catalyst | |
EP3325457B1 (en) | Process for preparing furan-2,5-dicarboxylic acid | |
EP2647631B1 (en) | Preparation method of catalyzing carbohydrate into 5-hydroxymethylfurfural | |
JP2015083559A (en) | Method for producing 2,5-furan dicarboxylic acid | |
CN108164481A (en) | A kind of preparation method of 5 hydroxymethyl furfural | |
KR101336981B1 (en) | The method of aromatic compounds production using tungsten oxide titania catalyst for hydrodeoxygenation of Guaiacol | |
CA2998975A1 (en) | Process for the preparation of glycols | |
CN110229124B (en) | Catalytic system for efficiently preparing 5-hydroxymethylfurfural and application thereof | |
CN103275096A (en) | Method for preparing isosorbide based on cellulose | |
DE102012200086A1 (en) | Process for the preparation of furan compounds from renewable raw materials | |
CN109134230B (en) | Method for preparing D-configuration excessive lactic acid by catalytic conversion of xylose, glucose, xylan, microcrystalline cellulose and corn straw | |
CN114591171A (en) | Preparation method of pharmaceutical grade ultra-high purity ethyl pyruvate | |
US20180272319A1 (en) | Process for the preparation of a hydrogenation catalyst and its use for the preparation of glycols | |
CN101830787B (en) | Method for synthesizing methyl isobutyl ketone and diisobutyl ketone by acetone gas-phase one-step method | |
CN113292522A (en) | Method for preparing 5-hydroxymethylfurfural by catalyzing biomass sugar with organic acid | |
CN111170840B (en) | Application of supported bifunctional catalyst in preparation of 3-acetyl propanol from furfural | |
CN109647388B (en) | Hydrogenation catalyst, preparation method thereof and preparation method of tetrahydrofurfuryl alcohol | |
CN106748750B (en) | Method for preparing lactic acid from hemicellulose in corn straws | |
CN1089035C (en) | Catalyst for preparing 2-methylfuran by gas-phase hydrogenation of furaldehyde and its application | |
CN110002939B (en) | Efficient adamantane synthesis method | |
KR101504727B1 (en) | A method to dehydrate polyols | |
NL2024500A (en) | Method for preparing 4-(3-hydroxyphenyl)-4-oxobutanoic acid from lignin | |
CN107185571B (en) | Cobalt catalyst, preparation method thereof and application thereof in catalytic synthesis of 2,3, 5-trimethylbenzoquinone | |
CN111499497A (en) | Preparation method of thymol | |
CN110981691A (en) | Method for synthesizing 1, 6-hexanediol by using monosaccharide |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |