CN105170099A - Adsorbing-catalyzing agent based on amino-functionalized ionic liquid and preparation method thereof - Google Patents
Adsorbing-catalyzing agent based on amino-functionalized ionic liquid and preparation method thereof Download PDFInfo
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Abstract
The invention discloses an adsorbing-catalyzing agent based on amino-functionalized ionic liquid. The adsorbing-catalyzing agent is prepared by taking a mesoporous moecular sieve SBA-16 as a carrier and amino-functionalized ionic liquid 1-(3-aminopropyl)-3-[3-(triethoxysilyl)propyl]-4,5-dihydroimidazole chloride as an active component and grafting the amino-functionalized ionic liquid to the carrier, wherein 1-10 mmol of the amino-functionalized ionic liquid is loaded in every 1 g of the adsorbing-catalyzing agent. The adsorbing-catalyzing agent integrates an adsorption capturing function and a catalytic conversion function into a whole and can achieve synchronous adsorption and conversion of CO2 and reduce the cost of a CUU technique.
Description
Technical field
The present invention relates to a kind of CO
2absorption-catalyst, particularly relate to a kind of based on ionic liquid active component, collecting obtains and catalysis efficient CO
2absorption-catalyst, and the preparation method of this absorption-catalyst.
Background technology
Global warming has become the environmental problem received much concern, with CO
2being that main greenhouse gases discharge in a large number, is the main cause causing greenhouse effects to aggravate.From resource angle, CO
2again C
1no matter carbon resource the most cheap and abundant in family, consider from the utilization of resources or the angle of environmental protection, relevant CO
2research and development that are fixing and chemical conversion are all significant.Therefore, CO
2trapping becomes the current hot spot technology urgently developed with (CCU) technology of utilization.
CO
2inertia is very large, is not easily activated, and realize its chemistry and fix and transform very difficult, thus the performance issue of adsorbent and catalyst constrains the application and development of CCU technology further.If design a kind of collecting to obtain and the absorption-catalyst of catalysis in one, by CO
2after efficient trapping, converted in-situ is the product that added value is higher, then can simplify technology path, reduce costs, and promotes the development of CCU technology.
Ionic liquid is made up of anions and canons completely, lower than the organic salt be in a liquid state in 100 DEG C of temperature ranges.Ionic liquid has the peculiar properties such as steam forces down, nonflammable, heat endurance is high, solvability is strong, structures and characteristics is adjustable.These characteristics make ionic liquid become alternative traditional organic amine solvent trapping fixation of C O
2new type ideal solvent.In addition, unique catalytic performance also makes ionic liquid in a mild condition namely to multiple CO
2conversion reaction shows excellent catalytic activity and selective.Therefore, the ionic liquid of design ad hoc structure, as active component, will be expected to realize CO
2trapping and conversion integration.But ionic liquid also exists again that viscosity is large, high in cost of production shortcoming, seriously constrains its application.
Summary of the invention
The object of this invention is to provide a kind of collecting and integrate ion liquid based absorption-catalyst with the amino functional of catalysis, and the preparation method of this absorption-catalyst, to realize CO
2synchronous absorption and conversion, reduce CUU technical costs.
Ion liquid based absorption-the catalyst of amino functional of the present invention is for carrier with mesopore molecular sieve SBA-16, with amino functional ionic liquid 1-(3-aminopropyl)-3-[3-(three ethoxy silylation) propyl group]-4, the two hydrogen imidazolium chloride of 5-is active component, the grafting of amino functional ionic liquid is formed on the carrier, wherein, in absorption-catalyst described in every 1g, load has 1 ~ 10mmol amino functional ionic liquid.
The present invention and then provide a kind of method preparing the ion liquid based absorption-catalyst of described amino functional is in anhydrous acetonitrile dicyandiamide solution under nitrogen protection, first by
n-[3-(three ethoxy silylation) propyl group]-4, the two hydrogen imidazoles of 5-and 3-chloro propyl amine hydrochloric acid salt heating reflux reaction obtain amino functional ionic liquid, heating reflux reaction is carried out again by amino functional ionic liquid and pure silicon mesopore molecular sieve SBA-16, by the solid dispersal that is obtained by reacting in absolute ethyl alcohol, adjust ph, to alkalescent, obtains the ion liquid based absorption-catalyst of described amino functional.
In the above-mentioned preparation method of the present invention, described in
nthe two hydrogen imidazoles of-[3-(three ethoxy silylation) propyl group]-4,5-is preferably 1: 1 ~ 2 with the mole dosage ratio of 3-chloro propyl amine hydrochloric acid salt.
Further, described in
nthe reaction time of the two hydrogen imidazoles of-[3-(three ethoxy silylation) propyl group]-4,5-and 3-chloro propyl amine hydrochloric acid salt is 24 ~ 72 hours, with absolute ethanol washing, drying after product removing acetonitrile, can obtain amino functional ionic liquid.
The reaction time of described pure silicon mesopore molecular sieve SBA-16 and amino functional ionic liquid is preferably 24 ~ 72 hours.
More specifically, amino functional ionic liquid and the reacted reactant of pure silicon mesopore molecular sieve SBA-16 filter, wash, after drying, are that solvent rope carries 48 hours, then are dispersed in absolute ethyl alcohol, with the KHCO of 0.25mol/L with carrene by the present invention
3about solution adjust ph to 8, after filtration, washing, obtain amino functional ion liquid based absorption-catalyst light yellow solid after drying.
Ion liquid based absorption-the catalyst of amino functional prepared by the present invention can be applicable to absorption and catches and catalyzed conversion CO
2.
Utilize the ion liquid based absorption-catalyst traps of amino functional of the present invention and transform CO
2concrete grammar be: under the adsorption temp of 25 ~ 75 DEG C, catch CO with the ion liquid based absorption-Catalyst Adsorption of described amino functional
2, then cycloaddition reaction is carried out, synthesizing annular carbonate with epoxide at reaction pressure 2Mpa, temperature 50 ~ 120 DEG C.
Usually, the reaction time of described cycloaddition reaction is 3 ~ 40 hours.
Preferably, epoxide of the present invention is epoxychloropropane, and the cyclic carbonate of synthesis is 4-chloromethyl-[1,3] dioxy ring penta-2-ketone.
The present invention adopts the method for chemical bonding, amino functional ionic liquid active component is grafted on the three-dimensional mesoporous silicon dioxide molecular sieve SBA-16 carrier that has compared with Large ratio surface sum pore volume, prepare and a kind ofly integrate that absorption catches with catalyzed conversion function, the efficient CO that capacity is large, activity is high and cyclic utilization rate is good
2heterogeneous absorption-catalyst, achieves CO
2high power capacity, low energy consumption trapping and cyclic carbonate Efficient Conversion, be CO
2fixing conversion particularly CO in flue gas
2industrial utilization provide effective method.
By ionic liquid supported on the porous carrier that specific area is large, can significantly reduce ionic liquid consumption, reduce CO
2resistance to mass tranfer, and be easy to be separated and reuse, thus can significantly improve adsoption catalysis efficiency and recycle rate.SBA-16 is as a member of mesopore molecular sieve, compared with MCM-41, the SBA-15 in straight hole road, its three-dimensional cubic pore void structure not easily blocks and has better transmission performance, have more superiority, higher application potential is had in fields such as absorption, separation, catalysis, can as the excellent carrier of solid-loaded ionic-liquid.
Absorption-catalyst prepared by the present invention has concentrated the good trapping performance of ionic liquid and excellent catalyzed conversion performance, simultaneously owing to having ionic liquid and porous carrier to the synergy of acid gas adsorption, to the CO in typical flue gas temperature range
2there is good absorption property, to epoxide and CO
2between cycloaddition reaction also there is the advantages such as high, selective good, the reusable edible of conversion ratio.
Absorption-catalyst prepared by the present invention can efficient adsorption CO under normal pressure, effluent gas temperature
2, and by CO under uniform temperature, pressure
2be converted into cyclic carbonate, show active high, selective good, reaction condition is gentle, be easy to the advantages such as separation, reusable edible, can realize CO
2synchronous absorption and conversion, reduce CUU technical costs
.
Detailed description of the invention
Embodiment 1
Take 0.274g (1mmol)
nthe two hydrogen imidazoles of-[3-(three ethoxy silylation) propyl group]-4,5-, 0.156g (1.2mmol) 3-chloro propyl amine hydrochloric acid salt, joins in 5mL anhydrous acetonitrile, and logical nitrogen protection, is heated to 80 DEG C of back flow reaction 24 hours under stirring.After reaction terminates, revolve and steam removing solvent acetonitrile, the product obtained with absolute ethanol washing, room temperature in vacuo is dry, obtains amino functional ionic liquid 0.4g.
Take 1g pure silicon mesopore molecular sieve SBA-16, be scattered in 50mL anhydrous acetonitrile together with the above-mentioned amino functional ionic liquid prepared, logical nitrogen protection, is heated to 80 DEG C of back flow reaction 24 hours under stirring.Reaction terminates rear filtration and obtains solid product, and after absolute ethanol washing, drying, add in apparatus,Soxhlet's, with carrene extracting 48 hours, vacuum drying, was dispersed in 30mL absolute ethyl alcohol, drips 0.25mol/LKHCO
3solution, regulates the pH value of dispersion liquid to about 8, filters, with water, absolute ethanol washing, vacuum drying, obtains the ion liquid based absorption of amino functional-catalyst light yellow solid 1.3g, be labeled as SBA-16@IL-1.
Embodiment 2
Take 0.822g (3mmol)
nthe two hydrogen imidazoles of-[3-(three ethoxy silylation) propyl group]-4,5-, 0.546g (4.2mmol) 3-chloro propyl amine hydrochloric acid salt, joins in 15mL anhydrous acetonitrile, and logical nitrogen protection, is heated to 80 DEG C of back flow reaction 36 hours under stirring.After reaction terminates, revolve and steam removing solvent acetonitrile, the product obtained with absolute ethanol washing, room temperature in vacuo is dry, obtains amino functional ionic liquid 1.2g.
Take 1g pure silicon mesopore molecular sieve SBA-16, be scattered in 50mL anhydrous acetonitrile together with the above-mentioned amino functional ionic liquid prepared, logical nitrogen protection, is heated to 80 DEG C of back flow reaction 48 hours under stirring.Reaction terminates rear filtration and obtains solid product, and after absolute ethanol washing, drying, add in apparatus,Soxhlet's, with carrene extracting 48 hours, vacuum drying, was dispersed in 30mL absolute ethyl alcohol, drips 0.25mol/LKHCO
3solution, regulates the pH value of dispersion liquid to about 8, filters, with water, absolute ethanol washing, vacuum drying, obtains the ion liquid based absorption of amino functional-catalyst light yellow solid 2.0g, be labeled as SBA-16@IL-3.
Embodiment 3
Take 1.370g (5mmol)
nthe two hydrogen imidazoles of-[3-(three ethoxy silylation) propyl group]-4,5-, 1.040g (8.0mmol) 3-chloro propyl amine hydrochloric acid salt, joins in 25mL anhydrous acetonitrile, and logical nitrogen protection, is heated to 80 DEG C of back flow reaction 48 hours under stirring.After reaction terminates, revolve and steam removing solvent acetonitrile, the product obtained with absolute ethanol washing, room temperature in vacuo is dry, obtains amino functional ionic liquid 2.0g.
Take 1g pure silicon mesopore molecular sieve SBA-16, be scattered in 50mL anhydrous acetonitrile together with the above-mentioned amino functional ionic liquid prepared, logical nitrogen protection, is heated to 80 DEG C of back flow reaction 60 hours under stirring.Reaction terminates rear filtration and obtains solid product, and after absolute ethanol washing, drying, add in apparatus,Soxhlet's, with carrene extracting 48 hours, vacuum drying, was dispersed in 30mL absolute ethyl alcohol, drips 0.25mol/LKHCO
3solution, regulates the pH value of dispersion liquid to about 8, filters, with water, absolute ethanol washing, vacuum drying, obtains the ion liquid based absorption of amino functional-catalyst light yellow solid 2.4g, be labeled as SBA-16@IL-5.
Embodiment 4
Take 2.740g (10mmol)
nthe two hydrogen imidazoles of-[3-(three ethoxy silylation) propyl group]-4,5-, 2.340g (18mmol) 3-chloro propyl amine hydrochloric acid salt, joins in 25mL anhydrous acetonitrile, and logical nitrogen protection, is heated to 80 DEG C of back flow reaction 60 hours under stirring.After reaction terminates, revolve and steam removing solvent acetonitrile, the product obtained with absolute ethanol washing, room temperature in vacuo is dry, obtains amino functional ionic liquid 4.0g.
Take 1g pure silicon mesopore molecular sieve SBA-16, be scattered in 50mL anhydrous acetonitrile together with the above-mentioned amino functional ionic liquid prepared, logical nitrogen protection, is heated to 80 DEG C of back flow reaction 72 hours under stirring.Reaction terminates rear filtration and obtains solid product, and after absolute ethanol washing, drying, add in apparatus,Soxhlet's, with carrene extracting 48 hours, vacuum drying, was dispersed in 30mL absolute ethyl alcohol, drips 0.25mol/LKHCO
3solution, regulates the pH value of dispersion liquid to about 8, filters, with water, absolute ethanol washing, vacuum drying, obtains the ion liquid based absorption of amino functional-catalyst light yellow solid 2.4g, be labeled as SBA-16@IL-10.
Following application examples uses thermogravimetric analyzer, with pure molecular sieve SBA-16 in contrast (comparative example 1 ~ 3), measures and compares the ion liquid based absorption-catalyst of amino functional prepared by above-described embodiment to sour gas CO
2absorption property.
Application examples 1
Take about 10mgSBA-16@IL-5 and be placed in thermogravimetric analyzer crucible, at 80cm
3the nitrogen of/min flows down, and from room temperature, is warming up to 130 DEG C and keeps constant temperature, purge to constant weight with the heating rate of 10 DEG C/min; Be cooled to adsorption temp 25 DEG C in nitrogen atmosphere, pass into pure CO
2gas carries out adsorption reaction 60min, computer software automatic data collection.The CO of sample
2adsorbance calculates according to TGA measurement result, is 39.60mg/g.
Application examples 2
Working sample SBA-16@IL-10, CO under similarity condition
2adsorbance is 47.08mg/g.
Application examples 3
CO
2adsorption reaction temperature is 50 DEG C, and other conditions are with application examples 1, CO
2adsorbance is 27.31mg/g.
Application examples 4
With the CO of 50 DEG C
2adsorption reaction temperature measuring SBA-16@IL-10, other conditions are with application examples 1, CO
2adsorbance is 31.87mg/g.
Application examples 5
CO
2adsorption reaction temperature is 75 DEG C, and other conditions are with application examples 1, CO
2adsorbance is 25.00mg/g.
Application examples 6
With the CO of 75 DEG C
2adsorption reaction temperature measuring SBA-16@IL-10, other conditions are with application examples 1, CO
2adsorbance is 29.33mg/g.
Comparative example 1
Take the pure molecular sieve SBA-16 of about 10mg and be placed in thermogravimetric analyzer crucible, at 80cm
3the nitrogen of/min flows down, and from room temperature, is warming up to 130 DEG C and keeps constant temperature, purge to constant weight with the heating rate of 10 DEG C/min; Be cooled to adsorption temp 25 DEG C in nitrogen atmosphere, pass into pure CO
2gas carries out adsorption reaction 60min, computer software automatic data collection.The CO of sample
2adsorbance calculates according to TGA measurement result, is 29.48mg/g.
Comparative example 2
CO
2adsorption reaction temperature is 50 DEG C, and other conditions are with comparative example 1, CO
2adsorbance is 11.98mg/g.
Comparative example 3
CO
2adsorption reaction temperature is 75 DEG C, and other conditions are with comparative example 1, CO
2adsorbance is 10.45mg/g.
Above-mentioned application examples and comparative example determination data are summarized in table 1.As can be seen from Table 1, under similarity condition, absorption-catalyst prepared by the present invention is to CO
2absorption property be significantly better than pure molecular sieve SBA-16.
Application examples 7
1g absorption-catalyst S BA-16@IL-1 is added, 9.25g (100mmol) epoxychloropropane in 100mL autoclave, airtight, with the CO of 1.0Mpa
2displace air in still completely, be slowly warming up to 120 DEG C, controlling reaction pressure is that 2.0Mpa reacts 6 hours.After the cooling of question response still, slowly release remaining CO
2, get supernatant liquor after products obtained therefrom is centrifugal and carry out GC analysis, the productive rate of 4-chloromethyl-[1,3] dioxy ring penta-2-ketone is 90.1%, selective 95.2%.
Application examples 8
Add 1g absorption-catalyst S BA-16@IL-3, other conditions are identical with application examples 7, and the productive rate recording 4-chloromethyl-[1,3] dioxy ring penta-2-ketone is 96.0%, and selective 96.9%.
Application examples 9
Add 1g absorption-catalyst S BA-16@IL-5, other conditions are identical with application examples 7, and the productive rate recording 4-chloromethyl-[1,3] dioxy ring penta-2-ketone is 96.0%, and selective 97.9%.
Application examples 10
Add 1g absorption-catalyst S BA-16@IL-10, other conditions are identical with application examples 7, and the productive rate recording 4-chloromethyl-[1,3] dioxy ring penta-2-ketone is 95.5%, and selective 97.4%.
Application examples 11
Add 1g absorption-catalyst S BA-16@IL-10, reaction temperature 100 DEG C, other conditions are identical with application examples 7, and the productive rate recording 4-chloromethyl-[1,3] dioxy ring penta-2-ketone is 72.3%, and selective 96.8%.
Application examples 12
Add 1g absorption-catalyst S BA-16@IL-10, in 3 hours reaction time, other conditions are identical with application examples 7, and the productive rate recording 4-chloromethyl-[1,3] dioxy ring penta-2-ketone is 82.6%, and selective 95.9%.
Application examples 13
Add 1g absorption-catalyst S BA-16@IL-10, in 4 hours reaction time, other conditions are identical with application examples 7, and the productive rate recording 4-chloromethyl-[1,3] dioxy ring penta-2-ketone is 92.9%, and selective 96.9%.
Application examples 14
Add 1g absorption-catalyst S BA-16@IL-10, reaction temperature 100 DEG C, in 12 hours reaction time, other conditions are identical with application examples 7, and the productive rate recording 4-chloromethyl-[1,3] dioxy ring penta-2-ketone is 82.0%, and selective 95.9%.
Application examples 15
Add 1g absorption-catalyst S BA-16@IL-10, reaction temperature 100 DEG C, in 20 hours reaction time, other conditions are identical with application examples 7, and the productive rate recording 4-chloromethyl-[1,3] dioxy ring penta-2-ketone is 95.2%, and selective 98.6%.
Application examples 16
Add 1g absorption-catalyst S BA-16@IL-10, reaction temperature 75 DEG C, in 40 hours reaction time, other conditions are identical with application examples 7, and the productive rate recording 4-chloromethyl-[1,3] dioxy ring penta-2-ketone is 72.0%, and selective 95.9%.
Comparative example 4
Pure molecular sieve SBA-16,9.25g (100mmol) epoxychloropropane of 1g is added in 100mL autoclave, airtight, with the CO of 1.0Mpa
2displace air in still completely, be slowly warming up to 120 DEG C, controlling reaction pressure is that 2.0Mpa reacts 6 hours.After the cooling of question response still, slowly release remaining CO
2, get supernatant liquor after products obtained therefrom is centrifugal and carry out GC analysis, do not detect 4-chloromethyl-[1,3] dioxy ring penta-2-ketone, productive rate and be selectively 0.
Application examples 17
By colourless to supernatant for the absorption of collected by centrifugation after reaction in application examples 10-catalyst absolute methanol washing, reuse after vacuum 80 DEG C of dryings, method is with application examples 10.Recycle result as shown in table 2.
Claims (10)
1. the ion liquid based absorption-catalyst of amino functional, for carrier with mesopore molecular sieve SBA-16, with amino functional ionic liquid 1-(3-aminopropyl)-3-[3-(three ethoxy silylation) propyl group]-4, the two hydrogen imidazolium chloride of 5-is active component, the grafting of amino functional ionic liquid is formed on the carrier, wherein, in absorption-catalyst described in every 1g, load has 1 ~ 10mmol amino functional ionic liquid.
2. the preparation method of the ion liquid based absorption-catalyst of amino functional described in claim 1 is in anhydrous acetonitrile dicyandiamide solution under nitrogen protection, first by
n-[3-(three ethoxy silylation) propyl group]-4, the two hydrogen imidazoles of 5-and 3-chloro propyl amine hydrochloric acid salt heating reflux reaction obtain amino functional ionic liquid, heating reflux reaction is carried out again by amino functional ionic liquid and pure silicon mesopore molecular sieve SBA-16, by the solid dispersal that is obtained by reacting in absolute ethyl alcohol, adjust ph, to alkalescent, obtains the ion liquid based absorption-catalyst of described amino functional.
3. preparation method according to claim 2, described in is characterized in that
nthe two hydrogen imidazoles of-[3-(three ethoxy silylation) propyl group]-4,5-is 1: 1 ~ 2 with the mole dosage ratio of 3-chloro propyl amine hydrochloric acid salt.
4. preparation method according to claim 2, described in is characterized in that
nthe reaction time of the two hydrogen imidazoles of-[3-(three ethoxy silylation) propyl group]-4,5-and 3-chloro propyl amine hydrochloric acid salt is 24 ~ 72 hours.
5. preparation method according to claim 2, is characterized in that the reaction time of described pure silicon mesopore molecular sieve SBA-16 and amino functional ionic liquid is 24 ~ 72 hours.
6. preparation method according to claim 2, is characterized in that with KHCO
3solution regulates the pH value of dispersion liquid.
7. the ion liquid based absorption-catalyst of amino functional described in claim 1 is caught and catalyzed conversion CO in absorption
2on application.
8. application according to claim 7, is characterized in that under the adsorption temp of 25 ~ 75 DEG C, catches CO with the ion liquid based absorption-Catalyst Adsorption of described amino functional
2, then cycloaddition reaction synthesizing annular carbonate is carried out with epoxide at reaction pressure 2Mpa, temperature 50 ~ 120 DEG C.
9. application according to claim 8, is characterized in that described epoxide is epoxychloropropane.
10. application according to claim 8, is characterized in that the time of described cycloaddition reaction is 3 ~ 40 hours.
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