CN108864030A - A method of carbon dioxide synthesizing annular carbonate is catalyzed with new catalyst - Google Patents
A method of carbon dioxide synthesizing annular carbonate is catalyzed with new catalyst Download PDFInfo
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- CN108864030A CN108864030A CN201810964919.0A CN201810964919A CN108864030A CN 108864030 A CN108864030 A CN 108864030A CN 201810964919 A CN201810964919 A CN 201810964919A CN 108864030 A CN108864030 A CN 108864030A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Abstract
The present invention relates to environment protection fields, particularly with regard to a kind of method with new catalyst catalysis carbon dioxide synthesizing annular carbonate；Disclosed in the method for the present invention it is a kind of with new catalyst catalysis carbon dioxide synthesizing annular carbonate method, this method using epoxide lanthanum modified graphene catalyst, 4-dimethylaminopyridine, calcium hydroxy phosphate, cyclodextrin and ammonium bromide co-catalysis effect under with carbon dioxide synthesizing annular carbonate.This method is low in cost, reaction condition is mild, without using heavy metal catalyst, there is no metal recovery pollution problems, a kind of lanthanum modified graphene catalyst used overcomes the problem that quaternary ammonium salt separation is difficult and activity is low, is a kind of novel, green, efficient, cyclicity and the good carbon-supported catalysts of stability.
Description
Technical field
The present invention relates to environment protection fields, are catalyzed carbon dioxide synthesizing annular carbonate with new catalyst particularly with regard to a kind of
Method.
Background technique
As mankind's activity aggravates, a large amount of fossil fuel is consumed, and atmospheric carbon dioxide levels increase year by year, dioxy
The increase for changing concentration of carbon will lead to the environmental problem of greenhouse effects, and resource utilization carbon dioxide is always that technical research person are closed
The research hotspot of note.
CN107354478A discloses a kind of method that microorganism electro synthesis system realizes Resources of Carbon Dioxide.The invention
A kind of method using microorganism electro synthesis system reducing carbon dioxide is provided, wherein cathode uses mixing anaerobic microorganism, institute
Stating mixing anaerobic microorganism includes Proteobacteria, Firmicutes and Bacteroidetes.The invention also provides one kind
Microorganism electro synthesis system and device, including at least one anode and at least one cathode, wherein cathode uses the micro- life of mixing anaerobic
Object, the mixing anaerobic microorganism includes Proteobacteria, Firmicutes and Bacteroidetes.The invention provides
Method and apparatus can use common electrodes material realize carbon dioxide reduction at volatile fatty acid, in the same of save the cost
When, there is the substance of high added value using the mixed thallus system of domestication enrichment, to reach at three environment, the energy and resource aspects
To good effect.
CN105884605A discloses a kind of method of Resources of Carbon Dioxide, under the conditions of existing for the nano nickel, by two
Oxidation carbon source is reacted with reducing agent, obtains formic acid or acetic acid.Compared with prior art, the invention is using nano nickel as catalyst
The recycling of carbon dioxide is completed, reaction condition is mild；Catalytic selectivity is high, and product only has formic acid or acetic acid, and the two is all
Industrial chemicals is with a wide range of applications；Catalytic efficiency is higher, and catalytic activity is influenced smaller by pH value, and equipment is simple, cost
It is lower.
CN204198863U discloses the device that a kind of phase interface electrochemical catalysis reduction carbon dioxide prepares carbon monoxide,
Belong to Resources of Carbon Dioxide to utilize and renewable energy technical field of energy storage.The device includes phase interface electrolytic cell, electrolyte
The circulatory system and carbon dioxide solubility absorption plant, the carbon dioxide solubility absorption plant catholyte outlet are connected to phase
Interface is electrolysed bottom of pond portion, and catholyte upper outlet connects electrolyte circulation system, electrolyte circulation in phase interface electrolytic cell
System is flowed into carbon dioxide solubility absorption plant by pump.The tank voltage of electrolytic cell is relatively low in the device, electric energy effect
Rate is relatively high.
The above invention or the prior art realize that Resources of Carbon Dioxide is usually to utilize biotechnology or heavy metal catalyst
Agent catalysis, for these technologies there are at high cost, condition is harsh, and metal recovery is difficult and reuse ratio is low, and there are the pollutions of heavy metal
More serious problem.
Summary of the invention
To solve the above-mentioned problems, carbon dioxide synthesis of cyclic carbonic acid is catalyzed with new catalyst the present invention provides a kind of
The method of ester.
A method of it being catalyzed carbon dioxide synthesizing annular carbonate with new catalyst, its technical solution is as follows：
According to mass fraction, by 80-100 parts of epoxide, 1-5 parts of lanthanum modified graphene catalyst, 0.05-0.5 parts
4-dimethylaminopyridine, 0.5-2.8 parts of calcium hydroxy phosphate, 0.6-1.2 parts of cyclodextrin and 0.5-2.8 parts of ammonium bromide add
Enter into autoclave, after mixing evenly ultrasonic disperse 20-30min, be then shut off reaction kettle, vacuumize, uses carbon dioxide
Air in replacement reaction kettle, in triplicate, then keeping pressure in kettle is 0.5-5MPa, keeps pressure steady in reaction process
It is fixed；It is then heated to 130-160 DEG C, reacts 3-8h；Complete the organic solvent lysate after reacting with 200-300 parts, filtering
Then catalyst out is used saturated common salt water washing liquor phase 3 times, with desiccant dryness, then solvent evaporated, can be obtained target production
Object cyclic carbonate.
The lanthanum modified graphene catalyst is prepared according to following scheme：
According to mass fraction, 0.5-2.5 parts of graphene oxide and 100-150 parts of toluene are added in reaction kettle, ultrasound
Disperse 40-60min, 1-5 parts of 5- bromine amyltrimethoxysilane is then added and is heated to 100-120 under nitrogen protection
DEG C, it is stirred to react 1-5h, then 0.5-3.5 parts of potassium bromide of addition and 1.2-5.6 parts of tri-n-butylamine, the three of 0.01-0.1 parts
[bis- (trimethyl silicane) amino] lanthanum, 0.05-0.5 parts of 1- (the chloro- 3- pyridazinyl of 6-) piperidines -4- methyl formates, the three of 0.2-0.8 parts
Fluorine dimethyl disulfide is etherified boron, 0.01-0.1 parts of 6- amino -2,3- dihydro 1-Indanone, 0.01-1 parts of 2- acrylamide base -2-
Methyl propane sulfonic acid, the reaction was continued 15-30h, are then centrifuged for filtering, modified graphene are separated, using dry after ethanol washing, i.e.,
The lanthanum modified graphene catalyst can be obtained.
The epoxide is propylene oxide or methyloxetane or glycidic acid or butadiene monoxide or epoxy third
Amide.
The organic solvent is ethyl acetate or butyl acetate or ether.
The desiccant is anhydrous sodium sulphate or anhydrous magnesium sulfate or anhydrous calcium chloride.
A kind of method with new catalyst catalysis carbon dioxide synthesizing annular carbonate, we disclosed in the method for the present invention
Method is using epoxide in lanthanum modified graphene catalyst, 4-dimethylaminopyridine, calcium hydroxy phosphate, cyclodextrin and ammonium bromide
Co-catalysis acts on lower and carbon dioxide synthesizing annular carbonate.This method is low in cost, and reaction condition is mild, without using a huge sum of money
Metal catalyst, is not present metal recovery pollution problem, and a kind of lanthanum modified graphene catalyst used overcomes quaternary ammonium salt separation difficult
It is a kind of novel, green, efficient, cyclicity and the good carbon-supported catalysts of stability with the low problem of activity.
Specific embodiment
The invention is described further below by specific embodiment：
Embodiment 1
A method of it being catalyzed carbon dioxide synthesizing annular carbonate with new catalyst, its technical solution is as follows：
According to mass fraction, by 90 parts of epoxide, 3 parts of lanthanum modified graphene catalyst, 0.25 part of 4- diformazan ammonia
Yl pyridines, 1.8 parts of calcium hydroxy phosphate, 0.9 part of cyclodextrin and 1.8 parts of ammonium bromide are added in autoclave, stirring
Ultrasonic disperse 25min, is then shut off reaction kettle, vacuumizes after uniformly, with the air in carbon dioxide replacement reaction kettle, repeats three
Secondary, then keeping pressure in kettle is 2.5MPa, keeps pressure to stablize in reaction process；140 DEG C are then heated to, 5h is reacted；It is complete
At the organic solvent lysate after reaction with 250 parts, catalyst is filtered out, is then used saturated common salt water washing liquor phase 3 times, is used
Desiccant dryness, then solvent evaporated, can be obtained target product cyclic carbonate.
The lanthanum modified graphene catalyst is prepared according to following scheme：
According to mass fraction, 1.5 parts of graphene oxide and 120 parts of toluene are added in reaction kettle, ultrasonic disperse
Then 50min is added 3 parts of 5- bromine amyltrimethoxysilane and is heated to 110 DEG C under nitrogen protection, is stirred to react 3h,
Then 2.5 parts of potassium bromide and 3.6 parts of tri-n-butylamine, 0.03 part three [bis- (trimethyl silicane) amino] lanthanums, 0.2 part of 1- are added
(the chloro- 3- pyridazinyl of 6-) piperidines -4- methyl formate, 0.5 part of trifluoro dimethyl disulfide are etherified boron, 0.05 part of 6- amino -2,3-
Dihydro 1-Indanone, 0.3 part of 2- acrylamide base -2- methyl propane sulfonic acid, the reaction was continued 20h, are then centrifuged for filtering, will be modified
The lanthanum modified graphene catalyst can be obtained using drying after ethanol washing in graphene separation.
The epoxide is propylene oxide.
The organic solvent is ethyl acetate.
The desiccant is anhydrous sodium sulphate.
This experiment cyclic carbonate yield is 93.19%, carbon dioxide conversion 97.69%.
Embodiment 2
A method of it being catalyzed carbon dioxide synthesizing annular carbonate with new catalyst, its technical solution is as follows：
According to mass fraction, by 80 parts of epoxide, 1 part of lanthanum modified graphene catalyst, 0.05 part of 4- diformazan ammonia
Yl pyridines, 0.5 part of calcium hydroxy phosphate, 0.6 part of cyclodextrin and 0.5 part of ammonium bromide are added in autoclave, stirring
Ultrasonic disperse 20min, is then shut off reaction kettle, vacuumizes after uniformly, with the air in carbon dioxide replacement reaction kettle, repeats three
Secondary, then keeping pressure in kettle is 0.5MPa, keeps pressure to stablize in reaction process；130 DEG C are then heated to, 3h is reacted；It is complete
At the organic solvent lysate after reaction with 200 parts, catalyst is filtered out, is then used saturated common salt water washing liquor phase 3 times, is used
Desiccant dryness, then solvent evaporated, can be obtained target product cyclic carbonate.
The lanthanum modified graphene catalyst is prepared according to following scheme：
According to mass fraction, 0.5 part of graphene oxide and 100 parts of toluene are added in reaction kettle, ultrasonic disperse
Then 40min is added 1- parts of 5- bromine amyltrimethoxysilane and is heated to 100 DEG C under nitrogen protection, is stirred to react 1h,
Then 0.5 part of potassium bromide and 1.2 parts of tri-n-butylamine, 0.01 part three [bis- (trimethyl silicane) amino] lanthanums, 0.05 part are added
1- (the chloro- 3- pyridazinyl of 6-) piperidines -4- methyl formate, 0.2 part of trifluoro dimethyl disulfide are etherified boron, 0.01 part of amino -2 6-,
3- dihydro 1-Indanone, 0.01 part of 2- acrylamide base -2- methyl propane sulfonic acid, the reaction was continued 15h, are then centrifuged for filtering, will change
Property graphene separation the lanthanum modified graphene catalyst can be obtained using dry after ethanol washing.
The epoxide is methyloxetane.
The organic solvent is butyl acetate.
The desiccant is anhydrous magnesium sulfate.
This experiment cyclic carbonate yield is 92.07%, carbon dioxide conversion 96.97%.
Embodiment 3
A method of it being catalyzed carbon dioxide synthesizing annular carbonate with new catalyst, its technical solution is as follows：
According to mass fraction, by 100 parts of epoxide, 5 parts of lanthanum modified graphene catalyst, 0.5 part of 4- diformazan ammonia
Yl pyridines, 2.8 parts of calcium hydroxy phosphate, 1.2 parts of cyclodextrin and 2.8 parts of ammonium bromide are added in autoclave, stirring
Ultrasonic disperse 30min, is then shut off reaction kettle, vacuumizes after uniformly, with the air in carbon dioxide replacement reaction kettle, repeats three
Secondary, then keeping pressure in kettle is 5MPa, keeps pressure to stablize in reaction process；160 DEG C are then heated to, 8h is reacted；It completes
With 300 parts of organic solvent lysate after reaction, catalyst is filtered out, is then used saturated common salt water washing liquor phase 3 times, with dry
Drying prescription is dry, and then solvent evaporated, can be obtained target product cyclic carbonate.
The lanthanum modified graphene catalyst is prepared according to following scheme：
According to mass fraction, 2.5 parts of graphene oxide and 150 parts of toluene are added in reaction kettle, ultrasonic disperse
Then 60min is added 5 parts of 5- bromine amyltrimethoxysilane and is heated to 120 DEG C under nitrogen protection, is stirred to react 5h,
Then 3.5 parts of potassium bromide and 5.6 parts of tri-n-butylamine, 0.1 part three [bis- (trimethyl silicane) amino] lanthanums, 0.5 part of 1- are added
(the chloro- 3- pyridazinyl of 6-) piperidines -4- methyl formate, 0.8 part of trifluoro dimethyl disulfide are etherified boron, 0.1 part of 6- amino -2,3- two
Hydrogen 1-Indanone, 1 part of 2- acrylamide base -2- methyl propane sulfonic acid, the reaction was continued 30h, are then centrifuged for filtering, by modified graphite
The lanthanum modified graphene catalyst can be obtained using drying after ethanol washing in alkene separation.
The epoxide is glycidic acid.
The organic solvent is ether.
The desiccant is anhydrous calcium chloride.
This experiment cyclic carbonate yield is 94.62%, carbon dioxide conversion 98.79%.
Embodiment 4
A method of it being catalyzed carbon dioxide synthesizing annular carbonate with new catalyst, its technical solution is as follows：
According to mass fraction, by 80 parts of epoxide, 1 part of lanthanum modified graphene catalyst, 0.05 part of 4- diformazan ammonia
Yl pyridines, 0.5 part of calcium hydroxy phosphate, 0.6 part of cyclodextrin and 0.5 part of ammonium bromide are added in autoclave, stirring
Ultrasonic disperse 20min, is then shut off reaction kettle, vacuumizes after uniformly, with the air in carbon dioxide replacement reaction kettle, repeats three
Secondary, then keeping pressure in kettle is 0.5MPa, keeps pressure to stablize in reaction process；130 DEG C are then heated to, 3h is reacted；It is complete
At the organic solvent lysate after reaction with 200 parts, catalyst is filtered out, is then used saturated common salt water washing liquor phase 3 times, is used
Desiccant dryness, then solvent evaporated, can be obtained target product cyclic carbonate.
The lanthanum modified graphene catalyst is prepared according to following scheme：
According to mass fraction, 2.5 parts of graphene oxide and 150 parts of toluene are added in reaction kettle, ultrasonic disperse
Then 60min is added 5 parts of 5- bromine amyltrimethoxysilane and is heated to 120 DEG C under nitrogen protection, is stirred to react 5h,
Then 3.5 parts of potassium bromide and 5.6 parts of tri-n-butylamine, 0.01 part three [bis- (trimethyl silicane) amino] lanthanums, 0.5 part of 1- are added
(the chloro- 3- pyridazinyl of 6-) piperidines -4- methyl formate, 0.2 part of trifluoro dimethyl disulfide are etherified boron, 0.1 part of 6- amino -2,3- two
Hydrogen 1-Indanone, 1 part of 2- acrylamide base -2- methyl propane sulfonic acid, the reaction was continued 30h, are then centrifuged for filtering, by modified graphite
The lanthanum modified graphene catalyst can be obtained using drying after ethanol washing in alkene separation.
The epoxide is butadiene monoxide.
The organic solvent is ether.
The desiccant is anhydrous sodium sulphate.
This experiment cyclic carbonate yield is 93.86%, carbon dioxide conversion 98.07%.
Embodiment 5
A method of it being catalyzed carbon dioxide synthesizing annular carbonate with new catalyst, its technical solution is as follows：
According to mass fraction, by 100 parts of epoxide, 5 parts of lanthanum modified graphene catalyst, 0.5 part of 4- diformazan ammonia
Yl pyridines, 2.8 parts of calcium hydroxy phosphate, 1.2 parts of cyclodextrin and 2.8 parts of ammonium bromide are added in autoclave, stirring
Ultrasonic disperse 30min, is then shut off reaction kettle, vacuumizes after uniformly, with the air in carbon dioxide replacement reaction kettle, repeats three
Secondary, then keeping pressure in kettle is 5MPa, keeps pressure to stablize in reaction process；160 DEG C are then heated to, 8h is reacted；It completes
With 300 parts of organic solvent lysate after reaction, catalyst is filtered out, is then used saturated common salt water washing liquor phase 3 times, with dry
Drying prescription is dry, and then solvent evaporated, can be obtained target product cyclic carbonate.
The lanthanum modified graphene catalyst is prepared according to following scheme：
According to mass fraction, 0.5 part of graphene oxide and 100 parts of toluene are added in reaction kettle, ultrasonic disperse
Then 40min is added 1- parts of 5- bromine amyltrimethoxysilane and is heated to 100 DEG C under nitrogen protection, is stirred to react 1h,
Then 0.5 part of potassium bromide and 1.2 parts of tri-n-butylamine, 0.1 part three [bis- (trimethyl silicane) amino] lanthanums, 0.05 part are added
1- (the chloro- 3- pyridazinyl of 6-) piperidines -4- methyl formate, 0.8 part of trifluoro dimethyl disulfide are etherified boron, 0.01 part of amino -2 6-,
3- dihydro 1-Indanone, 0.01 part of 2- acrylamide base -2- methyl propane sulfonic acid, the reaction was continued 15h, are then centrifuged for filtering, will change
Property graphene separation the lanthanum modified graphene catalyst can be obtained using dry after ethanol washing.
The epoxide is glycidamide.
The organic solvent is butyl acetate.
The desiccant is water calcium chloride.
This experiment cyclic carbonate yield is 93.59%, carbon dioxide conversion 97.28%.
Comparative example 1
Lanthanum modified graphene catalyst, the other the same as in Example 1 is not added.
This experiment cyclic carbonate yield is 75.33%, carbon dioxide conversion 70.57%.
Comparative example 2
Three [bis- (trimethyl silicane) amino] lanthanums, the other the same as in Example 1 is not added.
This experiment cyclic carbonate yield is 81.32%, carbon dioxide conversion 86.39%.
Comparative example 3
1- (the chloro- 3- pyridazinyl of 6-) piperidines -4- methyl formate, the other the same as in Example 1 is not added.
This experiment cyclic carbonate yield is 89.17%, carbon dioxide conversion 91.37%.
Comparative example 4
Trifluoro dimethyl disulfide etherificate boron, the other the same as in Example 1 is not added.
This experiment cyclic carbonate yield is 86.17%, carbon dioxide conversion 89.29%.
Comparative example 5
6- amino -2,3- dihydro 1-Indanone, the other the same as in Example 1 is not added.
This experiment cyclic carbonate yield is 87.29%, carbon dioxide conversion 90.34%.
Comparative example 6
2- acrylamide base -2- methyl propane sulfonic acid, the other the same as in Example 1 is not added.
This experiment cyclic carbonate yield is 87.29%, carbon dioxide conversion 90.34%.
Claims (5)
1. a kind of method with new catalyst catalysis carbon dioxide synthesizing annular carbonate, its technical solution is as follows：
According to mass fraction, by 80-100 parts of epoxide, 1-5 parts of lanthanum modified graphene catalyst, 0.05-0.5 parts
4-dimethylaminopyridine, 0.5-2.8 parts of calcium hydroxy phosphate, 0.6-1.2 parts of cyclodextrin and 0.5-2.8 parts of ammonium bromide add
Enter into autoclave, after mixing evenly ultrasonic disperse 20-30min, be then shut off reaction kettle, vacuumize, uses carbon dioxide
Air in replacement reaction kettle, in triplicate, then keeping pressure in kettle is 0.5-5MPa, keeps pressure steady in reaction process
It is fixed；It is then heated to 130-160 DEG C, reacts 3-8h；Complete the organic solvent lysate after reacting with 200-300 parts, filtering
Then catalyst out is used saturated common salt water washing liquor phase 3 times, with desiccant dryness, then solvent evaporated, can be obtained target production
Object cyclic carbonate.
2. a kind of method with new catalyst catalysis carbon dioxide synthesizing annular carbonate according to claim 1,
It is characterized in that：The lanthanum modified graphene catalyst is prepared according to following scheme：
According to mass fraction, 0.5-2.5 parts of graphene oxide and 100-150 parts of toluene are added in reaction kettle, ultrasound
Disperse 40-60min, 1-5 parts of 5- bromine amyltrimethoxysilane is then added and is heated to 100-120 under nitrogen protection
DEG C, it is stirred to react 1-5h, then 0.5-3.5 parts of potassium bromide of addition and 1.2-5.6 parts of tri-n-butylamine, the three of 0.01-0.1 parts
[bis- (trimethyl silicane) amino] lanthanum, 0.05-0.5 parts of 1- (the chloro- 3- pyridazinyl of 6-) piperidines -4- methyl formates, the three of 0.2-0.8 parts
Fluorine dimethyl disulfide is etherified boron, 0.01-0.1 parts of 6- amino -2,3- dihydro 1-Indanone, 0.01-1 parts of 2- acrylamide base -2-
Methyl propane sulfonic acid, the reaction was continued 15-30h, are then centrifuged for filtering, modified graphene are separated, using dry after ethanol washing, i.e.,
The lanthanum modified graphene catalyst can be obtained.
3. a kind of method with new catalyst catalysis carbon dioxide synthesizing annular carbonate according to claim 1,
It is characterized in that：The epoxide is propylene oxide or methyloxetane or glycidic acid or butadiene monoxide or epoxy third
Amide.
4. a kind of method with new catalyst catalysis carbon dioxide synthesizing annular carbonate according to claim 1,
It is characterized in that：The organic solvent is ethyl acetate or butyl acetate or ether.
5. a kind of method with new catalyst catalysis carbon dioxide synthesizing annular carbonate according to claim 1,
It is characterized in that：The desiccant is anhydrous sodium sulphate or anhydrous magnesium sulfate or anhydrous calcium chloride.
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| CN112844485A (en) * | 2021-01-27 | 2021-05-28 | 湖南工程学院 | Cyclodextrin-metal complex and preparation method and application thereof |
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| CN112844485A (en) * | 2021-01-27 | 2021-05-28 | 湖南工程学院 | Cyclodextrin-metal complex and preparation method and application thereof |
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