CN107814779A - A kind of method that diformyl furans of catalytic ammoxidation 2,5 prepares 2,5 furans dioximes - Google Patents
A kind of method that diformyl furans of catalytic ammoxidation 2,5 prepares 2,5 furans dioximes Download PDFInfo
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- CN107814779A CN107814779A CN201610822122.8A CN201610822122A CN107814779A CN 107814779 A CN107814779 A CN 107814779A CN 201610822122 A CN201610822122 A CN 201610822122A CN 107814779 A CN107814779 A CN 107814779A
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- 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
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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Abstract
The invention belongs to organic synthesis field, and in particular to a kind of diformyl furans of catalytic ammoxidation 2,5 prepares 2; the method of 5 furans dioximes, this method is with 2,5 diformyl furans for raw material; hydrogen peroxide is oxidant, and ammoniacal liquor is nitrogen source, under catalyst action; 30 120 DEG C carry out the 24h of ammoxidation reaction 0.5; catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent, recrystallization purifying; obtain 2,5 furans dioxime products.This method product yield high, product are easily isolated, and have good application prospect.
Description
Technical field
The present invention relates to Green Chemistry and energy field, in particular it relates to 2,5- diformyl furans catalytic ammoxidation systems
The method of standby 2,5- furans dioximes.
Background technology
In order to realize sustainable development, reproducible, rich reserves biomass resources are developed, to substitute or mend
The shortage of fossil resource is filled, is had very important significance, by the extensive concern and attention of domestic and international scientific circles and industrial quarters.
Wherein biomass resource is a kind of reproducible energy resources of green, and widely distributed in nature.Biomass is nature
Organic carbon resource of unique recyclable regenerative, and the important form of solar energy conversion and storage.Cellulose, hemicellulose, Portugal
The carbohydrate such as grape sugar are one of most important biomass resources, recyclable regenerative, and stock number is big.Using carbohydrate as original
Material, by chemical conversion process such as dehydrations, the important compounds such as 5 hydroxymethyl furfural can be obtained, the compound has become life
One of Important Platform compound in thing refining.5 hydroxymethyl furfural aoxidizes to obtain 2,5- diformyl furans.In the last few years, Xu
Outstanding research team is around 5 hydroxymethyl furfural oxidation (ChemSusChem 2011,4,51；Appl.Catal.A-Gen.2014,
482,231；Chem.-Eur.J.2013,19,14215；Green Chem.2011,13,554.), hydrogenation (ChemCatChem
2013,5,2822；ChemSusChem 2014,7,1352.), etherificate (Bioresour.Technol.2012,119,433；
J.Energy Chem.2013,22,93.) etc., carry out substantial amounts of research.Recently, we have developed 5 hydroxymethyl furfural
Catalytic ammoxidation-Pinner addition cascade reactions prepare 2,5- furans dimethyleneimine acid esters method (Green Chem.2016,
18,974.)。
In chemical field and biological field, oxime is all a kind of important compound, available for essences such as medicine, agricultural chemicals
In the synthesis of thin chemicals.Specifically, as acetaldoxime can be used as anti oxidation layer, it can also be used to medicine, the intermediate of pesticide synthesis.
And cyclohexanone oxime is intermediate important in caprolactam building-up process.The 2 of catalytic ammoxidation 2,5- diformyls furans preparation,
5- furans dioxime can be further converted to 2,5- furans dimethylamine.And 2,5- furans dimethylamine is the important monomer of polyamide.
At present, the synthesis of oxime is reacted to obtain by aldehyde, ketone and hydroxylamine hydrochloride or HAS more, caused hydrochloric acid or sulphur in course of reaction
Acid, it is often necessary in the sodium hydroxide of equimolar amounts and remove, reaction of atomic is less economical, seriously polluted.Therefore, new environment
Friendly building-up process is urgently developed.The aldehyde of molecular sieve catalytic, ketone and azanol reaction generation oxime caused by original position be a green,
The good route of Atom economy.
The Research Thinking of the present invention is to develop a catalytic ammoxidation 2, and 5- diformyls furans prepares 2,5- furans dioximes
New method.Specifically, using hydrogen peroxide as oxidant, using ammoniacal liquor as nitrogen source, azanol is produced under catalyst action, 2,5- bis-
Formylfuran occurs condensation reaction with azanol caused by original position and prepares 2,5- furans dioximes.
The content of the invention
The object of the present invention is to develop a kind of catalytic ammoxidation 2,5- diformyls furans prepares the skill of 2,5- furans dioximes
Art and method.
The technical solution adopted by the present invention is:Using hydrogen peroxide as oxidant, using ammoniacal liquor as nitrogen source, produced under catalyst action
Raw azanol, 2,5- diformyl furans occur condensation reaction with azanol caused by original position and prepare 2,5- furans dioximes.
According to method provided by the invention, reaction product 2,5- furans dioximes, it is characterized in that containing furan in molecular structure
Mutter ring and oximido, be the precursor of 2,5- furans dimethylamine, there is very big potential using value.
According to method provided by the invention, the catalyst is TS-1, TS-2, Ti-MWW, Ti-SBA-15, Ti-SBA-
16、Ti-MCM-41、Ti-MCM-22、Ti-MCM-48、Ti-KIT-6、Ti-MOR、Ti-FER、Ti-Beta、Ti-Y、Ti-X、
One or two or more kinds in ZSM-5, B-ZSM-5, Al-ZSM-5, MCM-41, B-MCM-41, Al-MCM-41；Catalyst amount
For the 5-20wt% of 2,5- diformyl furans amounts.
According to method provided by the invention, hydrogen peroxide is oxidant, and the concentration of hydrogen peroxide is 30-70wt%, hydrogen peroxide with
The mol ratio of 2,5- diformyl furans is 2-10:1；The mol ratio of preferable hydrogen peroxide and 2,5- diformyl furans is 3-5:1.
According to method provided by the invention, ammoniacal liquor is nitrogen source, and nitrogen source and the mol ratio of 2,5- diformyl furans are 2-10:
1；Preferable nitrogen source and the mol ratio of 2,5- diformyl furans are 3-6:1.
According to method provided by the invention, the reaction temperature of 2,5- diformyl furans ammoxidation reactions is 30-120 DEG C,
Reaction time is 0.5-24h；Preferable reaction temperature is 50-80 DEG C, and the preferable reaction time is 1-10h.
According to method provided by the invention, the reaction dissolvent of 2,5- diformyl furans ammoxidation reactions is water, methanol, second
One or two or more kinds in alcohol, normal propyl alcohol, isopropanol, n-butanol, isobutanol, the tert-butyl alcohol.
According to method provided by the invention, during concrete operations, catalyst, solvent, ammoniacal liquor, hydrogen peroxide are put into tri- mouthfuls of 50mL
In bottle, 30-120 DEG C is warming up to, the solution of 2,5- diformyl furans is slowly dropped in above-mentioned there-necked flask, at this temperature
Continue to react 0.5-24h, 2,5- diformyl furans are 2,5- furans dioximes by ammoxidation.
According to method provided by the invention, the separation method of 2, the 5- diformyls furans ammoxidation reaction products is,
After reaction terminates, mixture is cooled down, is centrifuged off catalyst, is evaporated under reduced pressure and removes solvent, then fully washed with saturated aqueous common salt
Solid is washed, is filtered, recrystallization purifying obtains 2,5- furans dioximes.
The qualitative of product is analyzed using high performance liquid chromatography, NMR, and is compared with the retention time of standard sample.
Beneficial effects of the present invention:
The present invention develops one kind with biomass-based derivative 2, and 5- diformyls furans is raw material, using water or alcohol as reaction
Medium, with hydrogen peroxide oxygen source, using ammoniacal liquor as ammonia source, the methods and techniques of 2,5- furans dioximes are produced under catalytic action.This is urged
Agent is cheap and easy to get, is easily separated with product.Excellent product performance, purity are high.This technology path is for alleviating petroleum resources
Shortage, the dependence of chemical products and energy chemistry product to fossil resources such as oil is reduced, is had great importance.
Embodiment
The present invention is described in detail with specific embodiment below, but the present invention implements to be not limited to these embodiments：
Embodiment 1：By 248mg Ti-MWW, 5mL water, 20mmol ammoniacal liquor and 20mmol 30wt% hydrogen peroxide are added to
In 50mL there-necked flasks, 70 DEG C are heated to, by 10mL 1mol/L 2, the aqueous solution of 5- diformyl furans is slowly dropped into above-mentioned three
In mouth bottle, continue to react 2h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent, then use saturated aqueous common salt
Fully washing solid, filtering, recrystallization purifying obtain 2,5- furans dioximes, separation yield 98%.
Embodiment 2：By 200mg Ti-MOR, 5mL methanol, 70mmol ammoniacal liquor and 80mmol 60wt% hydrogen peroxide are added to
In 50mL there-necked flasks, 60 DEG C are heated to, by 10mL 1mol/L 2, the methanol solution of 5- diformyl furans is slowly dropped into above-mentioned
In there-necked flask, continue to react 2.5h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent, then eaten with saturation
Salt solution fully washs solid, and filtering, recrystallization purifying obtains 2,5- furans dioximes, separation yield 91%.
Embodiment 3：By 100mg Ti-Beta, 5mL ethanol, 100mmol ammoniacal liquor and 100mmol 55wt% hydrogen peroxide add
Into 50mL there-necked flasks, 30 DEG C are heated to, by 10mL 1mol/L 2, the ethanol solution of 5- diformyl furans is slowly dropped into
State in there-necked flask, continue to react 24h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent, then eaten with saturation
Salt solution fully washs solid, and filtering, recrystallization purifying obtains 2,5- furans dioximes, separation yield 78%.
Embodiment 4：By 80mg Ti-FER, 5mL water and ethanol (volume ratio 1:1), 40mmol ammoniacal liquor and 50mmol
50wt% hydrogen peroxide is added in 50mL there-necked flasks, is heated to 55 DEG C, by 10mL1mol/L 2, the ethanol of 5- diformyl furans
Solution is slowly dropped into above-mentioned there-necked flask, continues to react 8h at such a temperature.Catalyst is centrifuged off, it is molten to be evaporated under reduced pressure removing
Agent, solid is fully then washed with saturated aqueous common salt, filtered, recrystallization purifying obtains 2,5- furans dioximes, separation yield 95%.
Embodiment 5：By 150mg TS-1,5mL water and methanol (volume ratio 1:1), 60mmol ammoniacal liquor and 60mmol 30wt%
Hydrogen peroxide is added in 50mL there-necked flasks, is heated to 50 DEG C, by 10mL 1mol/L 2, the ethanol solution of 5- diformyl furans
It is slowly dropped into above-mentioned there-necked flask, continues to react 2h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent, so
Solid is fully washed with saturated aqueous common salt afterwards, is filtered, recrystallization purifying obtains 2,5- furans dioximes, separation yield 93%.
Embodiment 6：By 62mg Ti-SBA-15,5mL n-butanols, 30mmol ammoniacal liquor and 40mmol 40wt% hydrogen peroxide add
Enter into 50mL there-necked flasks, be heated to 40 DEG C, by 10mL 1mol/L 2, the butanol solution of 5- diformyl furans slowly drips
Enter in above-mentioned there-necked flask, continue to react 3.5h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent, Ran Houyong
Saturated aqueous common salt fully washs solid, and filtering, recrystallization purifying obtains 2,5- furans dioximes, separation yield 58%.
Embodiment 7：By 70mg Ti-SBA-16,5mL ethanol, 50mmol ammoniacal liquor and 50mmol 35wt% hydrogen peroxide add
Into 50mL there-necked flasks, 65 DEG C are heated to, by 10mL 1mol/L 2, the ethanol solution of 5- diformyl furans is slowly dropped into
State in there-necked flask, continue to react 8h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent, then eaten with saturation
Salt solution fully washs solid, and filtering, recrystallization purifying obtains 2,5- furans dioximes, separation yield 85%.
Embodiment 8：By 80mg Ti-MCM-41,5mL methanol, 80mmol ammoniacal liquor and 35mmol 70wt% hydrogen peroxide add
Into 50mL there-necked flasks, 75 DEG C are heated to, by 10mL 1mol/L 2, the methanol solution of 5- diformyl furans is slowly dropped into
State in there-necked flask, continue to react 4h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent, then eaten with saturation
Salt solution fully washs solid, and filtering, recrystallization purifying obtains 2,5- furans dioximes, separation yield 90%.
Embodiment 9：By 70mg Ti-MCM-22,5mL n-butanols, 100mmol ammoniacal liquor and 45mmol60wt% hydrogen peroxide add
Enter into 50mL there-necked flasks, be heated to 55 DEG C, by 10mL 1mol/L 2, the butanol solution of 5- diformyl furans slowly drips
Enter in above-mentioned there-necked flask, continue to react 15h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent, then with full
Solid is fully washed with saline solution, is filtered, recrystallization purifying obtains 2,5- furans dioximes, separation yield 93%.
Embodiment 10：By 85mg Ti-MCM-48,5mL n-butanols, 35mmol ammoniacal liquor and 55mmol40wt% hydrogen peroxide add
Enter into 50mL there-necked flasks, be heated to 60 DEG C, by 10mL 1mol/L 2, the butanol solution of 5- diformyl furans slowly drips
Enter in above-mentioned there-necked flask, continue to react 20h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent, then with full
Solid is fully washed with saline solution, is filtered, recrystallization purifying obtains 2,5- furans dioximes, separation yield 86%.
Embodiment 11：By 65mg Al-ZSM-5 and Ti-MOR (mass ratioes 1:1), 5mL ethanol, 45mmol ammoniacal liquor and
70mmol 65wt% hydrogen peroxide is added in 50mL there-necked flasks, is heated to 75 DEG C, by 10mL 1mol/L 2,5- diformyl furans
The ethanol solution muttered is slowly dropped into above-mentioned there-necked flask, continues to react 12h at such a temperature.Catalyst is centrifuged off, decompression is steamed
Solvent is removed in distillation, then fully washs solid with saturated aqueous common salt, and filtering, recrystallization purifying obtains 2,5- furans dioximes, separates
Yield 88%.
Embodiment 12：By 130mg ZSM-5 and Ti-Beta (mass ratioes 1:1), 5mL water, 55mmol ammoniacal liquor and 25mmol
70wt% hydrogen peroxide is added in 50mL there-necked flasks, is heated to 80 DEG C, by 10mL1mol/L 2,5- diformyl furans it is water-soluble
Liquid is slowly dropped into above-mentioned there-necked flask, continues to react 10h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent,
Then solid is fully washed with saturated aqueous common salt, filtered, recrystallization purifying obtains 2,5- furans dioximes, separation yield 80%.
Embodiment 13：By 240mg B-ZSM-5,5mL isobutanols, 60mmol ammoniacal liquor and 70mmol30wt% hydrogen peroxide add
Into 50mL there-necked flasks, 50 DEG C are heated to, by 10mL 1mol/L 2, the isobutanol solution of 5- diformyl furans is slowly dropped into
In above-mentioned there-necked flask, continue to react 24h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent, then use saturation
Saline solution fully washs solid, and filtering, recrystallization purifying obtains 2,5- furans dioximes, separation yield 86%.
Embodiment 14：By 180mg Al-MCM-41, the 5mL tert-butyl alcohols, 90mmol ammoniacal liquor and 80mmol35wt% hydrogen peroxide add
Enter into 50mL there-necked flasks, be heated to 110 DEG C, by 10mL 1mol/L 2, the t-butanol solution of 5- diformyl furans is slowly dripped
Enter in above-mentioned there-necked flask, continue to react 3h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent, then with full
Solid is fully washed with saline solution, is filtered, recrystallization purifying obtains 2,5- furans dioximes, separation yield 73%.
Embodiment 15：By 160mg MCM-41 and Ti-X (mass ratioes 1:1), 5mL n-butanols, 40mmol ammoniacal liquor and 60mmol
55wt% hydrogen peroxide is added in 50mL there-necked flasks, is heated to 120 DEG C, and by 10mL 1mol/L 2,5- diformyls furans is just
Butanol solution is slowly dropped into above-mentioned there-necked flask, continues to react 0.5h at such a temperature.Catalyst is centrifuged off, vacuum distillation removes
Solvent is removed, then fully washs solid with saturated aqueous common salt, is filtered, recrystallization purifying obtains 2,5- furans dioximes, separation yield
95%.
Embodiment 16：By 140mg B-MCM-41,5mL isopropanols, 65mmol ammoniacal liquor and 50mmol45wt% hydrogen peroxide add
Enter into 50mL there-necked flasks, be heated to 65 DEG C, by 10mL 1mol/L 2, the aqueous isopropanol of 5- diformyl furans slowly drips
Enter in above-mentioned there-necked flask, continue to react 6h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent, then with full
Solid is fully washed with saline solution, is filtered, recrystallization purifying obtains 2,5- furans dioximes, separation yield 98%.
Embodiment 17：By 220mg Ti-X, 5mL water and n-butanol (volume ratio 1:1), 55mmol ammoniacal liquor and 80mmol
65wt% hydrogen peroxide is added in 50mL there-necked flasks, is heated to 80 DEG C, by 10mL1mol/L 2,5- diformyl furans it is water-soluble
Liquid is slowly dropped into above-mentioned there-necked flask, continues to react 2h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent,
Then solid is fully washed with saturated aqueous common salt, filtered, recrystallization purifying obtains 2,5- furans dioximes, separation yield 78%.
Embodiment 18：By 200mg Ti-Y, 5mL normal propyl alcohols, 55mmol ammoniacal liquor and 90mmol 60wt% hydrogen peroxide are added to
In 50mL there-necked flasks, 90 DEG C are heated to, by 10mL 1mol/L 2, the normal propyl alcohol solution of 5- diformyl furans is slowly dropped into
State in there-necked flask, continue to react 2.5h at such a temperature.Catalyst is centrifuged off, is evaporated under reduced pressure and removes solvent, then use saturation
Saline solution fully washs solid, and filtering, recrystallization purifying obtains 2,5- furans dioximes, separation yield 75%.
Embodiment 19：By 150mg Ti-KIT-6,5mL water and normal propyl alcohol (volume ratio 1:1), 70mmol ammoniacal liquor and 55mmol
40wt% hydrogen peroxide is added in 50mL there-necked flasks, is heated to 100 DEG C, by 10mL 1mol/L 2, the water of 5- diformyl furans
Alcoholic solution is slowly dropped into above-mentioned there-necked flask, continues to react 5h at such a temperature.Catalyst is centrifuged off, it is molten to be evaporated under reduced pressure removing
Agent, solid is fully then washed with saturated aqueous common salt, filtered, recrystallization purifying obtains 2,5- furans dioximes, separation yield 94%.
Embodiment 20：By 170mg TS-1,5mL water and n-butanol (volume ratio 1:1), 30mmol ammoniacal liquor and 45mmol
40wt% hydrogen peroxide is added in 50mL there-necked flasks, is heated to 70 DEG C, by 10mL1mol/L 2, the positive fourth of 5- diformyl furans
Alcoholic solution is slowly dropped into above-mentioned there-necked flask, continues to react 6h at such a temperature.Catalyst is centrifuged off, it is molten to be evaporated under reduced pressure removing
Agent, solid is fully then washed with saturated aqueous common salt, filtered, recrystallization purifying obtains 2,5- furans dioximes, separation yield 88%.
Claims (8)
1. a kind of catalytic ammoxidation 2, the method that 5- diformyls furans prepares 2,5- furans dioximes, it is characterised in that：With 2,5-
Diformyl furans is raw material, and hydrogen peroxide is oxidant, and ammoniacal liquor is nitrogen source, under catalyst action, 2,5- diformyl furans
By ammoxidation reaction, by purifies and separates, 2,5- furans dioximes are obtained；
The catalyst is：TS-1、TS-2、Ti-MWW、Ti-SBA-15、Ti-SBA-16、Ti-MCM-41、Ti-MCM-22、Ti-
MCM-48, Ti-KIT-6, Ti-MOR, Ti-FER, Ti-Beta, Ti-Y, Ti-X, ZSM-5, B-ZSM-5, Al-ZSM-5, MCM-
41st, the one or two or more kinds in B-MCM-41, Al-MCM-41.
2. according to the method for claim 1, it is characterised in that：Catalyst amount is the 5- of 2,5- diformyl furans
20wt%.
3. according to the method for claim 1, it is characterised in that：Hydrogen peroxide is oxidant, and the concentration of hydrogen peroxide is 30-
The mol ratio of 70wt%, hydrogen peroxide and 2,5- diformyl furans is 2-10:1；Preferable hydrogen peroxide and 2,5- diformyl furans
Mol ratio be 3-5:1.
4. according to the method for claim 1, it is characterised in that：Ammoniacal liquor is nitrogen source, nitrogen source and 2,5- diformyl furans
Mol ratio is 2-10:1；Preferable nitrogen source and the mol ratio of 2,5- diformyl furans are 3-6:1.
5. according to the method for claim 1, it is characterised in that：The reaction temperature of 2,5- diformyl furans ammoxidation reactions
For 30-120 DEG C, reaction time 0.5-24h；Preferable reaction temperature is 50-80 DEG C, and the preferable reaction time is 1-10h.
6. according to the method for claim 1, it is characterised in that：The reaction dissolvent of 2,5- diformyl furans ammoxidation reactions
For the one or two or more kinds in water, methanol, ethanol, normal propyl alcohol, isopropanol, n-butanol, isobutanol, the tert-butyl alcohol.
7. according to the method for claim 1, it is characterised in that：During concrete operations, by catalyst, solvent, ammoniacal liquor, hydrogen peroxide
Putting into 50mL there-necked flasks, be warming up to 30-120 DEG C, the solution of 2,5- diformyl furans is slowly dropped in above-mentioned there-necked flask,
Continue to react 0.5-24h at this temperature, 2,5- diformyl furans are 2,5- furans dioximes by ammoxidation.
8. according to the method for claim 1, it is characterised in that：The 2,5- diformyls furans ammoxidation reaction products
Separation method is, after reaction terminates, cools down mixture, is centrifuged off catalyst, is evaporated under reduced pressure and removes solvent, then eaten with saturation
Salt solution fully washs solid, and filtering, recrystallization purifying obtains 2,5- furans dioximes.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112011205B (en) * | 2020-10-23 | 2021-02-02 | 中国科学院宁波材料技术与工程研究所 | Environment-friendly antifouling agent, antifouling paint, multilayer protective film structure and application thereof |
| CN112830912A (en) * | 2020-06-02 | 2021-05-25 | 中国科学院宁波材料技术与工程研究所 | Method for continuously preparing 2, 5-furan dicarboxaldehyde oxime by solid acid catalysis |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112830912A (en) * | 2020-06-02 | 2021-05-25 | 中国科学院宁波材料技术与工程研究所 | Method for continuously preparing 2, 5-furan dicarboxaldehyde oxime by solid acid catalysis |
| CN112011205B (en) * | 2020-10-23 | 2021-02-02 | 中国科学院宁波材料技术与工程研究所 | Environment-friendly antifouling agent, antifouling paint, multilayer protective film structure and application thereof |
| WO2022082850A1 (en) * | 2020-10-23 | 2022-04-28 | 中国科学院宁波材料技术与工程研究所 | Environmentally-friendly anti-fouling agent, anti-fouling paint, multilayer protective film structure, and application thereof |
| US11773274B2 (en) | 2020-10-23 | 2023-10-03 | Ningbo Institute Of Materials Technology & Engineering, Chinese Academy Of Sciences | Environmental-friendly antifouling agent and antifouling paint, multi-layer protective film structure and use thereof |
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