CN104650015A - Method for preparing furyl aldehyde by using efficient catalytic oxidation of furfural and fatty alcohol - Google Patents
Method for preparing furyl aldehyde by using efficient catalytic oxidation of furfural and fatty alcohol Download PDFInfo
- Publication number
- CN104650015A CN104650015A CN201510029528.6A CN201510029528A CN104650015A CN 104650015 A CN104650015 A CN 104650015A CN 201510029528 A CN201510029528 A CN 201510029528A CN 104650015 A CN104650015 A CN 104650015A
- Authority
- CN
- China
- Prior art keywords
- furfural
- nano gold
- furyl
- fatty alcohol
- type nano
- 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.)
- Granted
Links
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a method for preparing furyl aldehyde by using efficient catalytic oxidation of furfural and fatty alcohol. Furyl aldehyde is prepared from furfural as a substrate and supported nano gold as a catalyst. The method comprises the following specific steps: dissolving furfural into an organic solvent, adding to the supported nano gold and an assistant, and reacting at 25-170 DEG C for 1-15 hours in a 0.01-05MPa oxygen atmosphere under the condition that the stirring speed is 100-5,000r/min; and carrying out selective catalytic oxidation on furfural and fatty alcohol through the supported nano gold, so as to prepare furyl aldehyde. The preparation method is simple and easy to operate, generates few by-products and is friendly to environment. A supported nano gold catalyst is adopted, is mild in condition, good in catalysis effect, easy to recover, and can be repeatedly used; the supported nano gold catalyst can be used for efficiently catalyzing oxidation of furfural with high selectivity to generate furyl aldehyde; and the product is easy to separate, the production cost is low, and technical and economic effects are remarkable, and therefore the method has a good application prospect.
Description
Technical field
The present invention relates to the method that biomass-based furfural effectively utilizes, particularly relate to a kind of method utilizing efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare furyl aldehyde.
Background technology
At present, along with worldwide petrochemical resource supply and demand contradiction, find and develop a kind of major issue that the method for fossil resources can be replaced to become chemical field face.In order to avoid causing certain burden to environment, avoiding discharging any harmful pollution substance; people are making great efforts to explore the natural energy resources that can utilize to excavate available green material; see: Y. Roman-Leshkov; J. N. Chheda; J. A. Dumesic, Science, 2006; 312,1933; C. Zhou, X. Xia, C. Lin, D. Tong, J. Beltramini, Chem. Soc. Rev., 2011,40,5588; J. C. Serrano-Ruiz, J. A. Dumesic, Energy Environ. Sci., 2011,4,83.Biomass are maximum renewable carbon resources on earth, and the consumption reducing mineral wealth with its chemical needed for raw material production has become a development trend of chemical field.
Furfural always gets more and more people's extensive concerning as a kind of important biomass resource, annual production is more than 200 000 tons, see Biorefineries-Industrial Processes and Products, ed. B. Kamm, P. R. Gruber and M. Kamm, Wiley-VCH, Weinheim, 2006.Utilize furfural condensation to produce the method for furyl aldehyde; it not only protects ecotope; decrease the consumption of mineral wealth simultaneously; furfural is that a kind of cheapness can obtain product, and can generate pentose under the action of an acid by pentosan, pentose is again through cyclisation; see: K. J. Zeitsch; The Chemistry and Technology of Furfural and its Many By-Products, Elsevier Science, 2000; S. Lima, M. Pillinger, A. A. Valente,
catal. Commun., 2008,
9, 2144, therefore utilizing furfural to produce furyl aldehyde, is an important channel of Appropriate application furfural.
Summary of the invention
The object of the invention is to for above-mentioned technical Analysis and existing problems, a kind of method utilizing efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare furyl aldehyde is provided, this preparation method's catalyzer make that simple consumption is few, product yield is high and be easy to be separated, reaction conditions is gentle, production cost is low, safety is environmentally friendly without hidden danger.
Technical scheme of the present invention:
A kind of method utilizing efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare furyl aldehyde, be substrate with furfural, take load type nano gold as catalyst preparing furyl aldehyde, concrete grammar is: be dissolved in by furfural in organic solvent, add load type nano gold and auxiliary agent, temperature be 25-170 DEG C, under oxygen atmosphere is 0.01-5MP, mixing speed 100-5000 rev/min condition, reaction 1-15 hour, by load type nano gold optionally catalyzed oxidation furfural and fatty alcohol, obtained furyl aldehyde.
Described organic solvent is the fatty alcohol of C1-C15, and the amount ratio of furfural and organic solvent is 0.2 g:15 mL.
Described load type nano gold adopts coprecipitation method preparation, and carrier is hydroxyapatite, the hydroxyapatite of load iron, cerium oxide, Z 250, tricobalt tetroxide, niobium oxides, aluminum oxide or hydrotalcite; Gold loading is 1-10wt%, and activation temperature is 400 DEG C, and soak time is 3 hours; The add-on of load type nano gold is the 5-40% of furfural quality.
Described auxiliary agent has salt of wormwood, saleratus, sodium carbonate, volatile salt or sodium hydroxide, and the mass ratio of auxiliary agent and furfural is 0.004-1: 1.
Advantage of the present invention is: this preparation method is simple to operation, the few and environmental friendliness of by product.Adopt load type nano gold catalyst, mild condition, excellent catalytic effect, be easy to reclaim and can reuse; Load type nano gold catalyst high-level efficiency, the oxidation of highly selective catalysis furfural can prepare furyl aldehyde, and product is easy to be separated, production cost is low, has significant techno-economic effect, has good application prospect.
Embodiment
Further instruction is given to the present invention below by example.In embodiment, described load type nano gold adopts coprecipitation method preparation, and gold loading is 5wt%, and activation temperature is 400 DEG C, and soak time is 3 hours.
embodiment 1:
One utilizes efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare 3-(2-furyl) method of propenal, take furfural as substrate, take ethanol as solvent, the load type nano gold being carrier with the hydroxyapatite of load iron is catalyzer, take oxygen as oxygen source, preparation 3-(2-furyl) propenal, concrete grammar is: be dissolved in by 0.2 g furfural in 15 mL ethanol, the hydroxyapatite of load iron is the load type nano gold 0.05 gram of carrier, 0.05 gram, auxiliary agent salt of wormwood, oxygen atmosphere is 0.3MP, it is 140 DEG C in temperature, under mixing speed 120 revs/min of conditions, react 4 hours, by load type nano gold optionally catalyzed oxidation furfural and the ethanol that the hydroxyapatite of load iron is carrier, obtained 3-(2-furyl) propenal.With gas chromatograph-mass spectrometer (GC-MS) and gas chromatographic analysis reaction result; The transformation efficiency of furfural is 95.75%, 3-(2-furyl) selectivity of propenal is 94.02%.
embodiment 2:
One utilizes efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare 3-(2-furyl) method of propenal, take furfural as substrate, take ethanol as solvent, take Z 250 as the load type nano gold of carrier be catalyzer, take oxygen as oxygen source, preparation 3-(2-furyl) propenal, concrete grammar is: be dissolved in by 0.2 g furfural in 15 mL ethanol, take Z 250 as the load type nano gold 0.05 gram of carrier, 0.05 gram, auxiliary agent salt of wormwood, oxygen atmosphere is 0.3MP, it is 140 DEG C in temperature, under mixing speed 120 revs/min of conditions, react 4 hours, by load type nano gold optionally catalyzed oxidation furfural and the ethanol that Z 250 is carrier, obtained 3-(2-furyl) propenal.With gas chromatograph-mass spectrometer (GC-MS) and gas chromatographic analysis reaction result; The transformation efficiency of furfural is 88.76%, 3-(2-furyl) selectivity of propenal is 84.34%.
embodiment 3:
One utilizes efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare 3-(2-furyl) method of propenal, take furfural as substrate, take ethanol as solvent, take Z 250 as the load type nano gold of carrier be catalyzer, take oxygen as oxygen source, preparation 3-(2-furyl) propenal, concrete grammar is: be dissolved in by 0.2 g furfural in 15 mL ethanol, take Z 250 as the load type nano gold 0.05 gram of carrier, 0.05 gram, auxiliary agent sodium hydroxide, oxygen atmosphere is 0.3MP, it is 140 DEG C in temperature, under mixing speed 120 revs/min of conditions, react 4 hours, by load type nano gold optionally catalyzed oxidation furfural and the ethanol that Z 250 is carrier, obtained 3-(2-furyl) propenal.With gas chromatograph-mass spectrometer (GC-MS) and gas chromatographic analysis reaction result; The transformation efficiency of furfural is 71.89%, 3-(2-furyl) selectivity of propenal is 62.51%.
embodiment 4:
One utilizes efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare 3-(2-furyl) method of propenal, take furfural as substrate, take ethanol as solvent, take hydrotalcite as the load type nano gold of carrier be catalyzer, take oxygen as oxygen source, preparation 3-(2-furyl) propenal, concrete grammar is: be dissolved in by 0.2 g furfural in 15 mL ethanol, take hydrotalcite as the load type nano gold 0.05 gram of carrier, 0.05 gram, auxiliary agent salt of wormwood, oxygen atmosphere is 0.3MP, it is 140 DEG C in temperature, under mixing speed 120 revs/min of conditions, react 4 hours, by taking hydrotalcite as load type nano gold optionally catalyzed oxidation furfural and the ethanol of carrier, obtained 3-(2-furyl) propenal.With gas chromatograph-mass spectrometer (GC-MS) and gas chromatographic analysis reaction result; The transformation efficiency of furfural is 80.44%, 3-(2-furyl) selectivity of propenal is 89.61%.
embodiment 5:
One utilizes efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare 2-methyl-3-(2-furyl) method of propenal, take furfural as substrate, take n-propyl alcohol as solvent, the load type nano gold being carrier with the hydroxyapatite of load iron is catalyzer, take oxygen as oxygen source, preparation 2-methyl-3-(2-furyl) propenal, concrete grammar is: be dissolved in by 0.2 g furfural in 15 mL n-propyl alcohols, the load type nano gold being carrier with the hydroxyapatite of load iron 0.05 gram, 0.05 gram, auxiliary agent salt of wormwood, oxygen atmosphere is 0.3MP, it is 140 DEG C in temperature, under mixing speed 120 revs/min of conditions, react 4 hours, by load type nano gold optionally catalyzed oxidation furfural and the n-propyl alcohol that the hydroxyapatite of load iron is carrier, obtained 2-methyl-3-(2-furyl) propenal.With gas chromatograph-mass spectrometer (GC-MS) and gas chromatographic analysis reaction result; The transformation efficiency of furfural is 93.95%, 2-methyl-3-(2-furyl) selectivity of propenal is 97.23%.
embodiment 6:
One utilizes efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare 2-methyl-3-(2-furyl) method of propenal, take furfural as substrate, take n-propyl alcohol as solvent, take hydroxyapatite as the load type nano gold of carrier be catalyzer, take oxygen as oxygen source, preparation 2-methyl-3-(2-furyl) propenal, concrete grammar is: be dissolved in by 0.2 g furfural in 15 mL n-propyl alcohols, take hydroxyapatite as the load type nano gold 0.05 gram of carrier, 0.05 gram, auxiliary agent salt of wormwood, oxygen atmosphere is 0.3MP, it is 140 DEG C in temperature, under mixing speed 120 revs/min of conditions, react 4 hours, by load type nano gold optionally catalyzed oxidation furfural and the n-propyl alcohol that hydroxyapatite is carrier, obtained 2-methyl-3-(2-furyl) propenal.With gas chromatograph-mass spectrometer (GC-MS) and gas chromatographic analysis reaction result; The transformation efficiency of furfural is 85.51%, 2-methyl-3-(2-furyl) selectivity of propenal is 90.38%.
embodiment 7:
One utilizes efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare 2-methyl-3-(2-furyl) method of propenal, take furfural as substrate, take n-propyl alcohol as solvent, take Z 250 as the load type nano gold of carrier be catalyzer, take oxygen as oxygen source, preparation 2-methyl-3-(2-furyl) propenal, concrete grammar is: be dissolved in by 0.2 g furfural in 15 mL n-propyl alcohols, take Z 250 as the load type nano gold 0.05 gram of carrier, 0.05 gram, auxiliary agent salt of wormwood, oxygen atmosphere is 0.3MP, it is 140 DEG C in temperature, under mixing speed 120 revs/min of conditions, react 4 hours, by load type nano gold optionally catalyzed oxidation furfural and the n-propyl alcohol that Z 250 is carrier, obtained 2-methyl-3-(2-furyl) propenal.With gas chromatograph-mass spectrometer (GC-MS) and gas chromatographic analysis reaction result; The transformation efficiency of furfural is 86.65%, 2-methyl-3-(2-furyl) selectivity of propenal is 96.57%.
embodiment 8:
One utilizes efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare 2-methyl-3-(2-furyl) method of propenal, take furfural as substrate, take n-propyl alcohol as solvent, take cerium oxide as the load type nano gold of carrier be catalyzer, take oxygen as oxygen source, preparation 2-methyl-3-(2-furyl) propenal, concrete grammar is: be dissolved in by 0.2 g furfural in 15 mL n-propyl alcohols, take cerium oxide as the load type nano gold 0.05 gram of carrier, 0.05 gram, auxiliary agent salt of wormwood, oxygen atmosphere is 0.3MP, it is 140 DEG C in temperature, under mixing speed 120 revs/min of conditions, react 4 hours, by load type nano gold optionally catalyzed oxidation furfural and the n-propyl alcohol that cerium oxide is carrier, obtained 2-methyl-3-(2-furyl) propenal.With gas chromatograph-mass spectrometer (GC-MS) and gas chromatographic analysis reaction result; The transformation efficiency of furfural is 88.19%, 2-methyl-3-(2-furyl) selectivity of propenal is 97.14%.
embodiment 9:
One utilizes efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare 3-methyl-3-(2-furyl) method of propenal, take furfural as substrate, take Virahol as solvent, the load type nano gold being carrier with the hydroxyapatite of load iron is catalyzer, take oxygen as oxygen source, preparation 3-methyl-3-(2-furyl) propenal, concrete grammar is: be dissolved in by 0.2 g furfural in 15 mL Virahols, the load type nano gold being carrier with the hydroxyapatite of load iron 0.05 gram, 0.05 gram, auxiliary agent salt of wormwood, oxygen atmosphere is 0.3MP, it is 140 DEG C in temperature, under mixing speed 120 revs/min of conditions, react 4 hours, by load type nano gold optionally catalyzed oxidation furfural and the Virahol that the hydroxyapatite of load iron is carrier, obtained 3-methyl-3-(2-furyl) propenal.With gas chromatograph-mass spectrometer (GC-MS) and gas chromatographic analysis reaction result; The transformation efficiency of furfural is 91.96%, 2-methyl-3-(2-furyl) selectivity of propenal is 96.08%.
The above embodiments show: adopt in the present invention the method provided, and high conversion, highly selective furfuraldehyde through catalytic oxidation can be generated furyl aldehyde; Catalyzer cheaper starting materials, be easy to get, reaction conditions is gentle, and reaction process is simple, and can meet the requirement of Technological Economy, is a catalyst system with application prospect.
Claims (4)
1. the method utilizing efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare furyl aldehyde, it is characterized in that: be substrate with furfural, take load type nano gold as catalyst preparing furyl aldehyde, concrete grammar is: be dissolved in by furfural in organic solvent, add load type nano gold and auxiliary agent, temperature be 25-170 DEG C, under oxygen atmosphere is 0.01-5MP, mixing speed 100-5000 rev/min condition, reaction 1-15 hour, by load type nano gold optionally catalyzed oxidation furfural and fatty alcohol, obtained furyl aldehyde.
2. utilize efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare the method for furyl aldehyde according to claim 1, it is characterized in that: described organic solvent is the fatty alcohol of C1-C15, the amount ratio of furfural and organic solvent is 0.2 g:15 mL.
3. utilize efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare the method for furyl aldehyde according to claim 1, it is characterized in that: described load type nano gold adopts coprecipitation method preparation, carrier is hydroxyapatite, the hydroxyapatite of load iron, cerium oxide, Z 250, tricobalt tetroxide, niobium oxides, aluminum oxide or hydrotalcite; Gold loading is 1-10wt%, and activation temperature is 400 DEG C, and soak time is 3 hours; The add-on of load type nano gold is the 5-40% of furfural quality.
4. utilize efficiently catalyzing and oxidizing furfural and fatty alcohol to prepare the method for furyl aldehyde according to claim 1, it is characterized in that: described auxiliary agent has salt of wormwood, saleratus, sodium carbonate, volatile salt or sodium hydroxide, the mass ratio of auxiliary agent and furfural is 0.004-1: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510029528.6A CN104650015B (en) | 2015-01-21 | 2015-01-21 | A kind of method that furyl aldehyde is prepared using efficiently catalyzing and oxidizing furfural and fatty alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510029528.6A CN104650015B (en) | 2015-01-21 | 2015-01-21 | A kind of method that furyl aldehyde is prepared using efficiently catalyzing and oxidizing furfural and fatty alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104650015A true CN104650015A (en) | 2015-05-27 |
| CN104650015B CN104650015B (en) | 2018-04-03 |
Family
ID=53241715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510029528.6A Active CN104650015B (en) | 2015-01-21 | 2015-01-21 | A kind of method that furyl aldehyde is prepared using efficiently catalyzing and oxidizing furfural and fatty alcohol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104650015B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107556272A (en) * | 2017-10-09 | 2018-01-09 | 天津理工大学 | A kind of method for being catalyzed furfural and oxidation of ethanol condensation 2 furacroleins of preparation |
| CN112876434A (en) * | 2021-02-08 | 2021-06-01 | 中国科学院长春应用化学研究所 | Method for synthesizing 2-vinyl furan by catalyzing furfural and derivatives thereof to convert |
-
2015
- 2015-01-21 CN CN201510029528.6A patent/CN104650015B/en active Active
Non-Patent Citations (6)
| Title |
|---|
| ELSA LASSEUGUETTE，ET AL.: "Photoreactive furan derivatives", 《JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A: CHEMISTRY》 * |
| FERNANDO CAGIDE-FAGÍN，ET AL.: "A Cascade Annulation Based Convergent Approach to Racemic Tetrodotoxin", 《EUR.J.ORG.CHEM.》 * |
| L.DI NUNNO，ET AL.: "SELECTIVE REDUCTION OF ALDEHYDES TO THE CORRESPONDING PRIMARY ALCOHOLS BY LITHIUM ENOLATE OF ACETALDEHYDE", 《TETRAHEDRON》 * |
| WEN CHEN,ET AL.: "Upgrading of Bio-oil in Supercritical Ethanol: Using Furfural and Acetic Acid as Model Compounds", 《BIORESOURCES》 * |
| XINLI TONG，ET AL.: "A tunable process: catalytic transformation of renewable furfural with aliphatic alcohols in the presence of molecular oxygen", 《CHEM.COMMUN.》 * |
| YU.M.SHAPIRO: "Reactions of aldehydes of the furan series. 4. Redox interaction of furfural with monohydric alcohols", 《CHEMISTRY OF HETEROCYCLIC COMPOUNDS》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107556272A (en) * | 2017-10-09 | 2018-01-09 | 天津理工大学 | A kind of method for being catalyzed furfural and oxidation of ethanol condensation 2 furacroleins of preparation |
| CN112876434A (en) * | 2021-02-08 | 2021-06-01 | 中国科学院长春应用化学研究所 | Method for synthesizing 2-vinyl furan by catalyzing furfural and derivatives thereof to convert |
| CN112876434B (en) * | 2021-02-08 | 2023-10-10 | 中国科学院长春应用化学研究所 | Method for synthesizing 2-vinyl furan by catalyzing conversion of furfural and derivatives thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104650015B (en) | 2018-04-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2518371C1 (en) | Method of obtaining ethyleneglycol from polyoxy compounds | |
| Njagi et al. | High-yield selective conversion of carbohydrates to methyl levulinate using mesoporous sulfated titania-based catalysts | |
| CN106279080B (en) | A kind of method that 5 hydroxymethyl furfural photocatalysis prepares 2,5- furandicarboxylic acids | |
| Tong et al. | Direct hydrogenolysis of biomass-derived furans over Pt/CeO2 catalyst with high activity and stability | |
| Li et al. | Pt nanoparticles over TiO2–ZrO2 mixed oxide as multifunctional catalysts for an integrated conversion of furfural to 1, 4-butanediol | |
| CN105289592A (en) | Method for preparing gamma-valerolactone by acetylpropionic acid catalytic hydrogenation | |
| CN104277020B (en) | Aqueous catalysis 5 hydroxymethyl furfural prepares the method for 2,5-furandicarboxylic acid | |
| CN112645908B (en) | Method for preparing maleic anhydride | |
| Wang et al. | Efficient and selective conversion of hexose to 5-hydroxymethylfurfural with tin–zirconium-containing heterogeneous catalysts | |
| Elsayed et al. | Catalytic hydrogenation and etherification of 5-Hydroxymethylfurfural into 2-(alkoxymethyl)-5-methylfuran and 2, 5-bis (alkoxymethyl) furan as potential biofuel additives | |
| Akinnawo et al. | Eco-friendly synthesis of valuable fuel bio-additives from glycerol | |
| Ashokraju et al. | Formic acid assisted hydrogenation of levulinic acid to\upgamma γ-valerolactone over ordered mesoporous Cu/Fe _ 2 O _ 3 Cu/Fe 2 O 3 catalyst prepared by hard template method | |
| Cui et al. | A catalytic oxidative valorization of biomass-derived furfural with ethanol by copper/azodicarboxylate system | |
| Murru et al. | Ruthenium (II) sulfoxides-catalyzed hydrogenolysis of glycols and epoxides | |
| Tong et al. | Efficient and selective transformation of biomass-derived furfural with aliphatic alcohols catalyzed by a binary Cu-Ce oxide | |
| CN104650014A (en) | Method for preparing methyl furoate by efficient catalytic oxidizing of furfural | |
| JP2007137785A (en) | Method for dehydration of polyhydridic alcohol | |
| CN111253212B (en) | Method for preparing 2, 5-hexanediol | |
| Zhang et al. | Highly efficient catalytic valorization of biomass-derived furfural in methanol and ethanol | |
| CN104650015A (en) | Method for preparing furyl aldehyde by using efficient catalytic oxidation of furfural and fatty alcohol | |
| CN112961123B (en) | Method for preparing 3- (2-furyl) -2-methyl-2-acrolein by catalyzing oxidation condensation of furfural and n-propanol | |
| CN114105914A (en) | Method for preparing 2, 5-furandimethanol by using 5-chloromethyl furfural | |
| CN107286006B (en) | Method for preparing vanillone and acetosyringone by catalytic alcoholysis of lignin | |
| CN104190401A (en) | Molybdenum-based composite metal oxide catalyst for synthesizing propenyl alcohol by glycerol and preparation method of molybdenum-based composite metal oxide catalyst | |
| CN105859662A (en) | Method for catalyzing selective oxidation of 5-hydroxymethyl furfural through manganese oxide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |