CN105170099B - A kind of amino functional ionic liquid base adsorption catalyst and preparation method thereof - Google Patents
A kind of amino functional ionic liquid base adsorption catalyst and preparation method thereof Download PDFInfo
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- CN105170099B CN105170099B CN201510659633.8A CN201510659633A CN105170099B CN 105170099 B CN105170099 B CN 105170099B CN 201510659633 A CN201510659633 A CN 201510659633A CN 105170099 B CN105170099 B CN 105170099B
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
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- Y02C20/40—Capture or disposal of greenhouse gases of CO2
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/151—Reduction of greenhouse gas [GHG] emissions, e.g. CO2
Abstract
The invention discloses a kind of amino functional ionic liquid base adsorption catalyst, it with mesopore molecular sieve SBA 16 is carrier to be, with amino functional ionic liquid 1 (3 aminopropyl) 3 [3 (three ethoxy silylation) propyl group] 4,5 pairs of hydrogen imidazolium chlorides are active component, the grafting of amino functional ionic liquid is constituted on the carrier, wherein, 1~10mmol amino functional ionic liquids are loaded with adsorption catalyst described in every 1g.Adsorption catalyst of the present invention integrates absorption capture and catalyzed conversion function, can realize CO2Synchronous absorption and convert, reduce CUU technical costs.
Description
Technical field
The present invention relates to a kind of CO2Absorption-catalyst, more particularly to a kind of based on ionic liquid active component, collection
Capture and the efficient CO of catalysis2Absorption-catalyst, and the absorption-catalyst preparation method.
Background technology
Global warming turns into the environmental problem received much concern, with CO2Based on greenhouse gases largely discharge, be to lead
Cause the main cause of greenhouse effects aggravation.Said from recycling angle, CO2It is C again1Carbon resource the most cheap and abundant in family,
No matter from the point of view of the utilization of resources or environmental protection, relevant CO2The research and development of fixed and chemical conversion all have
Significance.Therefore, CO2Trapping is with utilizing (CCU) technology to turn into the current hot spot technology urgently developed.
CO2Inertia is very big, is difficult to be activated, and realizes that its chemistry is fixed and it is extremely difficult to convert, thus adsorbent and catalysis
The performance issue of agent further constrains the application and development of CCU technologies.If design one kind collects capture and catalysis in one
Absorption-catalyst of body, by CO2Efficiently converted in-situ is the higher product of added value after trapping, then can simplify technology path,
Cost is reduced, promotes the development of CCU technologies.
Ionic liquid is to be made up of completely anions and canons, the organic salt being in a liquid state in less than 100 DEG C of temperature ranges.From
The peculiar property such as there is sub- liquid steam to force down, nonflammable, heat endurance is high, solvability is strong, structure and property are adjustable.
These characteristics cause ionic liquid turns into substitute traditional fixed CO of organic amine solvent trapping2New type ideal solvent.In addition, unique
Catalytic performance also cause ionic liquid in a mild condition i.e. to a variety of CO2Conversion reaction show excellent catalytic activity and
Selectivity.Therefore, the ionic liquid of design specific structure will be expected to realize CO as active component2Trapping and conversion integration.
However, ionic liquid has the shortcomings of viscosity is big, cost is high again, its application is seriously constrained.
The content of the invention
Integrate trapping and the amino functional ionic liquid base suction of catalysis it is an object of the invention to provide a kind of
Attached-catalyst, and the absorption-catalyst preparation method, to realize CO2Synchronous absorption and convert, reduction CUU technologies into
This.
Amino functional ionic liquid base absorption-catalyst of the present invention be using mesopore molecular sieve SBA-16 as carrier,
With the double hydrogen imidazolium chlorides of amino functional ionic liquid 1- (3- aminopropyls) -3- [3- (three ethoxy silylation) propyl group] -4,5-
For active component, amino functional ionic liquid is grafted what is constituted on the carrier, wherein, absorption-catalysis described in per 1g
1~10mmol amino functional ionic liquids are loaded with agent.
The present invention and then there is provided a kind of method for preparing the amino functional ionic liquid base absorption-catalyst, be
In anhydrous acetonitrile dicyandiamide solution under nitrogen protection, first byNThe double hydrogen imidazoles of-[3- (three ethoxy silylation) propyl group] -4,5- with
3- chloro propyl amine hydrochloric acid salt heating reflux reactions obtain amino functional ionic liquid, then by amino functional ionic liquid and pure silicon
Mesopore molecular sieve SBA-16 carries out heating reflux reaction, will react obtained solid and is scattered in absolute ethyl alcohol, regulation pH value to
Alkalescent, obtains the amino functional ionic liquid base absorption-catalyst.
It is described in the above-mentioned preparation method of the present inventionNThe double hydrogen imidazoles of-[3- (three ethoxy silylation) propyl group] -4,5- and 3- chlorine
The mole dosage ratio preferably 1: 1~2 of propylamin hydrochloride.
Further, it is describedNThe double hydrogen imidazoles of-[3- (three ethoxy silylation) propyl group] -4,5- and 3- chloro propyl amine hydrochloric acid salts
Reaction time is 24~72 hours, and reaction product, which is removed, is washed with absolute ethyl alcohol after acetonitrile, dried, you can obtain amino functional
Ionic liquid.
The reaction time of the pure silicon mesopore molecular sieve SBA-16 and amino functional ionic liquid is preferably 24~72 small
When.
More specifically, the present invention is that amino functional ionic liquid and pure silicon mesopore molecular sieve SBA-16 is reacted anti-
Answer after thing filtering, washing, drying, carried by solvent rope of dichloromethane 48 hours, then be dispersed in absolute ethyl alcohol, with
0.25mol/L KHCO3Solution adjusts pH value to 8 or so, and amino functional ionic liquid is obtained after filtering, washing, dry
Base absorption-catalyst light yellow solid.
Amino functional ionic liquid base absorption-catalyst prepared by the present invention can be applied to absorption capture and catalyzed conversion
CO2。
Utilize amino functional ionic liquid base absorption-catalyst traps of the present invention and conversion CO2Specific method be：
Under 25~75 DEG C of adsorption temp, with the amino functional ionic liquid base absorption-Catalyst Adsorption capture CO2, then at anti-
Answer at pressure 2Mpa, 50~120 DEG C of temperature with epoxide carry out cycloaddition reaction, synthesizing annular carbonate.
Usually, the reaction time of the cycloaddition reaction is 3~40 hours.
Preferably, epoxide of the present invention is epoxychloropropane, the cyclic carbonate of synthesis for 4- chloromethyls-
[1,3] the amyl- 2- ketone of dioxy ring.
Amino functional ionic liquid active component is grafted to larger ratio by the present invention using the method for chemical bonding
On the three-dimensional mesoporous silicon dioxide molecular sieve SBA-16 carriers of surface area and pore volume, a kind of collection absorption capture has been prepared with urging
Change transformation function, capacity is big, activity is high and cyclic utilization rate good efficient CO2Heterogeneous absorption-catalyst, is realized
CO2High power capacity, the Efficient Conversion of low energy consumption trapping and cyclic carbonate, be CO2Fixed conversion particularly flue gas in
CO2Industrial utilization provide effective method.
By ionic liquid supported on the big porous carrier of specific surface area, ionic liquid consumption can be substantially reduced, is reduced
CO2Resistance to mass tranfer, and be easily isolated and reuse, it is thus possible to significantly improve adsoption catalysis efficiency and recycling rate.
SBA-16 is as a member of mesopore molecular sieve, and compared with MCM-41, the SBA-15 in straight hole road, its three-dimensional cubic pore void structure is not
Easily block and have more preferable transmission performance, with more superiority, possess higher application in fields such as absorption, separation, catalysis and dive
Power, can as solid-loaded ionic-liquid excellent carrier.
Absorption-catalyst prepared by the present invention has concentrated the good trapping performance and excellent catalyzed conversion of ionic liquid
Can, simultaneously because with the synergy of ionic liquid and porous carrier to acid gas adsorption, to typical flue gas temperature model
Enclose interior CO2With preferable absorption property, to epoxide and CO2Between cycloaddition reaction also have high conversion rate, choosing
Selecting property is good, reusable edible the advantages of.
Absorption-catalyst prepared by the present invention can efficient absorption CO under normal pressure, effluent gas temperature2, and in a constant temperature
By CO under degree, pressure2Cyclic carbonate is converted into, shows that activity is high, the good, reaction condition of selectivity is gentle, be easily isolated, can
The advantages of recycling, can realize CO2Synchronous absorption and convert, reduce CUU technical costs.
Embodiment
Embodiment 1
Weigh 0.274g (1mmol)NThe double hydrogen imidazoles of-[3- (three ethoxy silylation) propyl group] -4,5-, 0.156g
(1.2mmol) 3- chloro propyl amine hydrochloric acid salts, are added in 5mL anhydrous acetonitriles, lead to nitrogen protection, and 80 DEG C of backflows are heated under stirring
Reaction 24 hours.After reaction terminates, revolving removes solvent acetonitrile, and obtained product is washed with absolute ethyl alcohol, and room temperature in vacuo is dried,
Obtain amino functional ionic liquid 0.4g.
1g pure silicon mesopore molecular sieve SBA-16 are weighed, are disperseed together with the above-mentioned amino functional ionic liquid prepared
In 50mL anhydrous acetonitriles, lead to nitrogen protection, 80 DEG C of back flow reactions are heated under stirring 24 hours.Reaction is filtrated to get after terminating
Solid product, washed with absolute ethyl alcohol, dry after, add apparatus,Soxhlet's in, with dichloromethane extract 48 hours, vacuum do
It is dry, it is dispersed in 30mL absolute ethyl alcohols, 0.25mol/L KHCO is added dropwise3Solution, adjusts the pH value of dispersion liquid to 8 or so,
Filter, with water, absolute ethyl alcohol washing, vacuum drying, obtain amino functional ionic liquid base absorption-catalyst light yellow solid
1.3g, labeled as SBA-16@IL-1.
Embodiment 2
Weigh 0.822g (3mmol)NThe double hydrogen imidazoles of-[3- (three ethoxy silylation) propyl group] -4,5-, 0.546g
(4.2mmol) 3- chloro propyl amine hydrochloric acid salts, are added in 15mL anhydrous acetonitriles, lead to nitrogen protection, and 80 DEG C of backflows are heated under stirring
Reaction 36 hours.After reaction terminates, revolving removes solvent acetonitrile, and obtained product is washed with absolute ethyl alcohol, and room temperature in vacuo is dried,
Obtain amino functional ionic liquid 1.2g.
1g pure silicon mesopore molecular sieve SBA-16 are weighed, are disperseed together with the above-mentioned amino functional ionic liquid prepared
In 50mL anhydrous acetonitriles, lead to nitrogen protection, 80 DEG C of back flow reactions are heated under stirring 48 hours.Reaction is filtrated to get after terminating
Solid product, washed with absolute ethyl alcohol, dry after, add apparatus,Soxhlet's in, with dichloromethane extract 48 hours, vacuum do
It is dry, it is dispersed in 30mL absolute ethyl alcohols, 0.25mol/L KHCO is added dropwise3Solution, adjusts the pH value of dispersion liquid to 8 or so,
Filter, with water, absolute ethyl alcohol washing, vacuum drying, obtain amino functional ionic liquid base absorption-catalyst light yellow solid
2.0g, labeled as SBA-16@IL-3.
Embodiment 3
Weigh 1.370g (5mmol)NThe double hydrogen imidazoles of-[3- (three ethoxy silylation) propyl group] -4,5-, 1.040g
(8.0mmol) 3- chloro propyl amine hydrochloric acid salts, are added in 25mL anhydrous acetonitriles, lead to nitrogen protection, and 80 DEG C of backflows are heated under stirring
Reaction 48 hours.After reaction terminates, revolving removes solvent acetonitrile, and obtained product is washed with absolute ethyl alcohol, and room temperature in vacuo is dried,
Obtain amino functional ionic liquid 2.0g.
1g pure silicon mesopore molecular sieve SBA-16 are weighed, are disperseed together with the above-mentioned amino functional ionic liquid prepared
In 50mL anhydrous acetonitriles, lead to nitrogen protection, 80 DEG C of back flow reactions are heated under stirring 60 hours.Reaction is filtrated to get after terminating
Solid product, washed with absolute ethyl alcohol, dry after, add apparatus,Soxhlet's in, with dichloromethane extract 48 hours, vacuum do
It is dry, it is dispersed in 30mL absolute ethyl alcohols, 0.25mol/L KHCO is added dropwise3Solution, adjusts the pH value of dispersion liquid to 8 or so,
Filter, with water, absolute ethyl alcohol washing, vacuum drying, obtain amino functional ionic liquid base absorption-catalyst light yellow solid
2.4g, labeled as SBA-16@IL-5.
Embodiment 4
Weigh 2.740g (10mmol)NThe double hydrogen imidazoles of-[3- (three ethoxy silylation) propyl group] -4,5-, 2.340g
(18mmol) 3- chloro propyl amine hydrochloric acid salts, are added in 25mL anhydrous acetonitriles, lead to nitrogen protection, and 80 DEG C of backflows are heated under stirring
Reaction 60 hours.After reaction terminates, revolving removes solvent acetonitrile, and obtained product is washed with absolute ethyl alcohol, and room temperature in vacuo is dried,
Obtain amino functional ionic liquid 4.0g.
1g pure silicon mesopore molecular sieve SBA-16 are weighed, are disperseed together with the above-mentioned amino functional ionic liquid prepared
In 50mL anhydrous acetonitriles, lead to nitrogen protection, 80 DEG C of back flow reactions are heated under stirring 72 hours.Reaction is filtrated to get after terminating
Solid product, washed with absolute ethyl alcohol, dry after, add apparatus,Soxhlet's in, with dichloromethane extract 48 hours, vacuum do
It is dry, it is dispersed in 30mL absolute ethyl alcohols, 0.25mol/L KHCO is added dropwise3Solution, adjusts the pH value of dispersion liquid to 8 or so,
Filter, with water, absolute ethyl alcohol washing, vacuum drying, obtain amino functional ionic liquid base absorption-catalyst light yellow solid
2.4g, labeled as SBA-16@IL-10.
Following application examples uses thermogravimetric analyzer, using pure molecular sieve SBA-16 as control (comparative example 1~3), determines ratio
Compared with above-described embodiment prepare amino functional ionic liquid base absorption-catalyst to sour gas CO2Absorption property.
Application examples 1
Weigh about 10mg SBA-16@IL-5 to be placed in thermogravimetric analyzer crucible, in 80cm3Under/min nitrogen stream, from room
Temperature starts, and 130 DEG C of holding constant temperature, purging to constant weight are warming up to 10 DEG C/min heating rate；Suction is cooled in nitrogen atmosphere
25 DEG C of enclosure temperature, is passed through pure CO2Gas carries out adsorption reaction 60min, computer software automatic data collection.The CO of sample2Adsorbance
Calculated according to TGA measurement results, be 39.60mg/g.
Application examples 2
Determination sample SBA-16@IL-10, CO under similarity condition2Adsorbance is 47.08mg/g.
Application examples 3
CO2Adsorption reaction temperature is 50 DEG C, and other conditions are with application examples 1, CO2Adsorbance is 27.31mg/g.
Application examples 4
With 50 DEG C of CO2Adsorption reaction temperature measuring SBA-16@IL-10, other conditions are with application examples 1, CO2Adsorbance is
31.87mg/g。
Application examples 5
CO2Adsorption reaction temperature is 75 DEG C, and other conditions are with application examples 1, CO2Adsorbance is 25.00mg/g.
Application examples 6
With 75 DEG C of CO2Adsorption reaction temperature measuring SBA-16@IL-10, other conditions are with application examples 1, CO2Adsorbance is
29.33mg/g。
Comparative example 1
Weigh the pure molecular sieve SBA-16 of about 10mg to be placed in thermogravimetric analyzer crucible, in 80cm3Under/min nitrogen stream,
Since room temperature, 130 DEG C of holding constant temperature, purging to constant weight are warming up to 10 DEG C/min heating rate；Cool in nitrogen atmosphere
To 25 DEG C of adsorption temp, pure CO is passed through2Gas carries out adsorption reaction 60min, computer software automatic data collection.The CO of sample2Inhale
Attached amount is calculated according to TGA measurement results, is 29.48mg/g.
Comparative example 2
CO2Adsorption reaction temperature is 50 DEG C, and other conditions are with comparative example 1, CO2Adsorbance is 11.98mg/g.
Comparative example 3
CO2Adsorption reaction temperature is 75 DEG C, and other conditions are with comparative example 1, CO2Adsorbance is 10.45mg/g.
Above-mentioned application examples and comparative example determination data is summarized in table 1.As can be seen from Table 1, under similarity condition, this
Absorption-the catalyst prepared is invented to CO2Absorption property be significantly better than pure molecular sieve SBA-16.
Application examples 7
1g absorption-catalyst SBA-16@IL-1,9.25g (100mmol) epoxy chlorine is added in 100mL autoclaves
Propane, it is closed, with 1.0Mpa CO2Air in kettle is displaced completely, 120 DEG C are to slowly warm up to, and controls the reaction pressure to be
2.0Mpa reacts 6 hours.After the cooling of question response kettle, remaining CO is slowly released2, supernatant liquor is taken after products obtained therefrom is centrifuged
GC analyses are carried out, the yield of 4- chloromethyls-amyl- 2- ketone of [1,3] dioxy ring is 90.1%, selectivity 95.2%.
Application examples 8
1g absorption-catalyst SBA-16@IL-3 are added, other conditions are identical with application examples 7, measure 4- chloromethyls-[1,3]
The yield of the amyl- 2- ketone of dioxy ring is 96.0%, selectivity 96.9%.
Application examples 9
1g absorption-catalyst SBA-16@IL-5 are added, other conditions are identical with application examples 7, measure 4- chloromethyls-[1,3]
The yield of the amyl- 2- ketone of dioxy ring is 96.0%, selectivity 97.9%.
Application examples 10
Add 1g absorption-catalyst SBA-16@IL-10, other conditions are identical with application examples 7, measure 4- chloromethyls-[1,
3] yield of the amyl- 2- ketone of dioxy ring is 95.5%, selectivity 97.4%.
Application examples 11
Addition 1g absorption-catalyst SBA-16@IL-10,100 DEG C of reaction temperature, other conditions are identical with application examples 7, survey
The yield for obtaining 4- chloromethyls-amyl- 2- ketone of [1,3] dioxy ring is 72.3%, selectivity 96.8%.
Application examples 12
1g absorption-catalyst SBA-16@IL-10 are added, in 3 hours reaction time, other conditions are identical with application examples 7, surveyed
The yield for obtaining 4- chloromethyls-amyl- 2- ketone of [1,3] dioxy ring is 82.6%, selectivity 95.9%.
Application examples 13
1g absorption-catalyst SBA-16@IL-10 are added, in 4 hours reaction time, other conditions are identical with application examples 7, surveyed
The yield for obtaining 4- chloromethyls-amyl- 2- ketone of [1,3] dioxy ring is 92.9%, selectivity 96.9%.
Application examples 14
Add 1g absorption-catalyst SBA-16@IL-10,100 DEG C of reaction temperature, 12 hours reaction time, other conditions with
Application examples 7 is identical, and the yield for measuring 4- chloromethyls-amyl- 2- ketone of [1,3] dioxy ring is 82.0%, selectivity 95.9%.
Application examples 15
Add 1g absorption-catalyst SBA-16@IL-10,100 DEG C of reaction temperature, 20 hours reaction time, other conditions with
Application examples 7 is identical, and the yield for measuring 4- chloromethyls-amyl- 2- ketone of [1,3] dioxy ring is 95.2%, selectivity 98.6%.
Application examples 16
Add 1g absorption-catalyst SBA-16@IL-10,75 DEG C of reaction temperature, 40 hours reaction time, other conditions with
Application examples 7 is identical, and the yield for measuring 4- chloromethyls-amyl- 2- ketone of [1,3] dioxy ring is 72.0%, selectivity 95.9%.
Comparative example 4
The pure molecular sieve SBA-16 of 1g are added in 100mL autoclaves, 9.25g (100mmol) epoxychloropropane is close
Close, with 1.0Mpa CO2Air in kettle is displaced completely, 120 DEG C are to slowly warm up to, and it is 2.0Mpa reactions 6 to control reaction pressure
Hour.After the cooling of question response kettle, remaining CO is slowly released2, take supernatant liquor to carry out GC analyses after products obtained therefrom is centrifuged,
4- chloromethyls-amyl- 2- ketone of [1,3] dioxy ring is not detected, and yield and selectivity are 0.
Application examples 17
Absorption-the catalyst being collected by centrifugation after being reacted in application examples 10 washs colourless to supernatant with absolute methanol, very
Reused after empty 80 DEG C of dryings, method is with application examples 10.Recycle result as shown in table 2.
Claims (10)
1. amino functional ionic liquid base absorption-catalyst, is using mesopore molecular sieve SBA-16 as carrier, with amino functional
The double hydrogen imidazolium chlorides of ionic liquid 1- (3- aminopropyls) -3- [3- (three ethoxy silylation) propyl group] -4,5- are active component, will
The grafting of amino functional ionic liquid is constituted on the carrier, wherein, it is loaded with 1 in absorption-catalyst described in per 1g~
10mmol amino functional ionic liquids.
2. the preparation method of amino functional ionic liquid base absorption-catalyst, is under nitrogen protection described in claim 1
In anhydrous acetonitrile dicyandiamide solution, first byNThe double hydrogen imidazoles of-[3- (three ethoxy silylation) propyl group] -4,5- and 3- chloro propyl amine hydrochloric acid salts
Heating reflux reaction obtains amino functional ionic liquid, then by amino functional ionic liquid and pure silicon mesopore molecular sieve SBA-
16 carry out heating reflux reaction, and the solid that reaction is obtained is scattered in absolute ethyl alcohol, and regulation pH value obtains described to alkalescent
Amino functional ionic liquid base absorption-catalyst.
3. preparation method according to claim 2, it is characterized in that describedN- [3- (three ethoxy silylation) propyl group] -4,5-
The mole dosage ratio of double hydrogen imidazoles and 3- chloro propyl amine hydrochloric acid salts is 1: 1~2.
4. preparation method according to claim 2, it is characterized in that describedN- [3- (three ethoxy silylation) propyl group] -4,5-
The reaction time of double hydrogen imidazoles and 3- chloro propyl amine hydrochloric acid salts is 24~72 hours.
5. preparation method according to claim 2, it is characterized in that the pure silicon mesopore molecular sieve SBA-16 and amino functional
The reaction time for changing ionic liquid is 24~72 hours.
6. preparation method according to claim 2, it is characterized in that with KHCO3Solution adjusts the pH value of dispersion liquid.
7. amino functional ionic liquid base absorption-catalyst described in claim 1 is in absorption capture and catalyzed conversion CO2On
Using.
8. application according to claim 7, it is characterized in that under 25~75 DEG C of adsorption temp, with the amino functional
Ionic liquid base absorption-Catalyst Adsorption capture CO2, with epoxy compound at reaction pressure 2MPa, 50~120 DEG C of temperature
Thing carries out cycloaddition reaction synthesizing annular carbonate.
9. application according to claim 8, it is characterized in that described epoxide is epoxychloropropane.
10. application according to claim 8, it is characterized in that the time of the cycloaddition reaction is 3~40 hours.
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| CN113842888B (en) * | 2021-09-26 | 2024-03-26 | 武汉工程大学 | SBA-15 molecular sieve adsorbent loaded with amino acid ionic liquid and preparation method and application thereof |
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