CN112295599A - Application of restricted-domain multi-site ionic liquid catalyst in synthesis of cyclic carbonate - Google Patents
Application of restricted-domain multi-site ionic liquid catalyst in synthesis of cyclic carbonate Download PDFInfo
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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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
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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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/08—Silica
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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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0285—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre also containing elements or functional groups covered by B01J31/0201 - B01J31/0274
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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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
- B01J37/10—Heat treatment in the presence of water, e.g. steam
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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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/324—Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions
- B01J2231/328—Cycloadditions involving more than 2 components or moieties, e.g. intra-/intermolecualar [2+2+2] or [2+2+1], e.g. Pauson-Khand type
Abstract
The invention provides a catalyst for synthesizing cyclic carbonate, a preparation method and a preparation method of the cyclic carbonate, wherein the catalyst is a heterogeneous catalyst of a compound shown in a limited domain formula I; the catalyst for synthesizing the cyclic carbonate is a heterogeneous catalyst with multi-site ionic liquid limited; active group R (R) in the catalyst1、R2、R3) Can generate a synergistic catalytic action with halogen atoms, so that the high-selectivity generation of the cyclic carbonate can be realized under mild reaction conditions without adding other auxiliary agents and catalysts, and the catalysts can be separated by simple filtrationIs used for catalyzing the synthesis of the cyclic carbonate. Compared with the same amount of bulk phase ionic liquid, the heterogeneous catalyst in the invention has higher catalytic activity and huge industrialization potential.
Description
Technical Field
The invention belongs to the field of catalysts, relates to a catalyst for synthesizing cyclic carbonate, a preparation method and a preparation method of the cyclic carbonate, and particularly relates to preparation of a limited-area multi-active-site ionic liquid catalyst and preparation of the cyclic carbonate.
Background
The proliferation of human production activities has led to a dramatic increase in the demand for fossil energy over the new century. Environmental problems such as warming of climate, rising of sea level, etc. are becoming more serious while causing energy shortage. During the use of fossil fuels, a large amount of CO2Emissions are the leading culprit in causing climate warming.
CO2Is a linear molecule formed by carbon-oxygen double bonds, and the carbon atom is in the highest valence state and has thermodynamic and kinetic stability. Cyclic carbonates are very important chemical products, and their excellent physicochemical properties such as high boiling point, high polarity, and good biodegradability and solubility make them widely used in printing and dyeing, textile, and electrochemical applications. In addition, the cyclic carbonate can also be used for the aspects of drug synthesis, production of fine chemical intermediates and the like.
The synthetic routes of cyclic carbonates reported or applied at present mainly include traditional phosgene method, ester exchange method and CO2Transformation synthesis method. By introducing CO2The cycloaddition reaction for converting and synthesizing the cyclic carbonate is a green chemical reaction with high atom utilization rate, and the product cyclic carbonate has high added value and is CO at present2One of the most promising approaches for resource utilization.
At present, against CO2Catalysts that have been developed for cycloaddition reactions with epoxides include homogeneous catalysts such as metal complexes, metal halides, organic bases, and Ionic Liquids (IL), and heterogeneous catalysts such as metal oxides, polyionic liquids, supported ionic liquids, organometallic frameworks (MOFs), and carbon materials, and the like. More or less of these catalytic systems are presentSuch as low catalytic activity, harsh reaction conditions, use of highly toxic organic solvents, high catalyst cost, etc.
CN101108843A discloses a method for synthesizing cyclic carbonate ester in aqueous system, which takes epoxide and carbon dioxide as raw materials, uses bidentate ionic liquid and alkali metal salt (not added) as catalyst, and reacts for 0-6 hours under the conditions of 0.1-10.0MPa and 313.15-483.15K to synthesize the cyclic carbonate ester. Compared with the traditional method, the synthesis method has the advantages of environmental friendliness, mild reaction conditions, stable catalyst heat, low cost, easy synthesis, high selectivity, reusability, high activity maintenance and the like, and has a very strong industrial application prospect. However, the bidentate ionic liquid catalyst used in the method has low catalytic efficiency of the methyl imidazole ring, and needs to add a cocatalyst, so that the catalytic system is complex.
CN108484568A discloses a method for preparing monothio propylene carbonate by using ionic liquid as a catalyst, which takes carbonyl sulfide and propylene oxide as raw materials and ionic liquid as a catalyst to react in a high-pressure reaction kettle to obtain the monothio propylene carbonate. The ionic liquid used in the method comprises 1-butyl-3-methylimidazole bromoborate, 1-butyl-3-methylimidazole fluoroborate, 1-butyl-3-methylimidazole fluorophosphate, 1-ethyl-3-methylimidazole fluoroborate and n-butyl pyridine fluoroborate, and the reaction conditions of the method are harsh.
CN107954971A discloses a method for preparing propylene carbonate by chemically fixing carbon dioxide, which takes propylene oxide and carbon dioxide as raw materials, adds a catalyst and a cocatalyst, and reacts in an organic reaction medium to synthesize the propylene carbonate. The method uses an inorganic Lewis acid catalyst, the surface of the catalyst has hydroxyl groups and Lewis acid site active centers, and potassium iodide, tetrabutyl ammonium bromide or tetraphenyl phosphine bromide are used as a cocatalyst to catalyze propylene oxide to prepare propylene carbonate.
Therefore, a novel catalyst is developed, so that the catalyst has multiple active sites, is limited in a molecular sieve, can catalyze the cycloaddition reaction to synthesize the cyclic carbonate ester with high efficiency and high selectivity under the condition of not adding other auxiliary agents and catalysts, can be easily recycled through filtration and separation, and has important significance for large-scale application.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a catalyst for synthesizing cyclic carbonate, a preparation method and a preparation method of the cyclic carbonate, so as to improve the conversion efficiency of the cyclic carbonate, reduce the dosage of the catalyst and simultaneously improve the recycling performance of the catalyst.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a catalyst for the synthesis of cyclic carbonates, said catalyst being a heterogeneous catalyst which confines a compound of formula i:
wherein R is1、R2、R3The halogen-free flame-retardant polyester resin is independently selected from hydrogen, substituted or unsubstituted C1-C20 straight chain or branched chain alkyl, carboxyl, hydroxyl, amino, sulfydryl and imino, n takes 1-4, and X is one of halogen.
The catalyst for synthesizing the cyclic carbonate is a catalyst with multi-site ionic liquid limited, and an active group R group of the ionic liquid and a halogen atom can generate a synergistic catalytic action, so that the cyclic carbonate can be synthesized by a high-efficiency and high-selectivity catalytic cycloaddition reaction under a mild condition without adding other auxiliary agents and catalysts.
Preferably, the catalyst is any one of the following compounds:
preferably, it is
In a second aspect, the present invention provides a method for preparing a catalyst having a multi-site ionic liquid confined therein, the method comprising: the catalyst with different limited ionic liquid amounts is synthesized by using the preferable multi-site ionic liquid as a template agent and tetraethyl orthosilicate as a silicon source and adjusting the ratio of the ionic liquid to the silicon source and the pH value of the solution.
Preferably, the ratio of the ionic liquid to the silicon source is 0.2 to 1.0, such as 0.2, 0.4, 0.6, etc.
Preferably, ammonia is used to adjust the pH of the solvent system.
The catalyst of the present invention is prepared by a method generally using water as a solvent. The reaction is generally carried out in a sealed hydrothermal kettle and is kept at 110 ℃ for 24h without stirring.
In a third aspect, the present invention provides a method for preparing a cyclic carbonate, the method comprising: under the condition of existence of a limited ionic liquid catalyst, carbon dioxide and an epoxy compound undergo a cycloaddition reaction to obtain cyclic carbonate.
The preparation method of the cyclic carbonate has the following reaction general formula:
wherein R is1Representation H, CH3、CH2Cl、C2H3、C4H9、C7H7O、C8H7O or C6H5Etc. R2Represents H, or R1、R2And also ethyl or phenyl, etc.
Preferably, the epoxy compound comprises any one of ethylene oxide, propylene oxide, butylene oxide, epichlorohydrin, styrene oxide, cyclohexane oxide or cyclopentane oxide or a combination of at least two thereof.
The epoxy compound of the present invention is not limited to the above-exemplified epoxy compounds, and any epoxy compound can be reacted with CO2Any structure that undergoes a cycloaddition reaction to produce a cyclic carbonate may be used as a reaction raw material.
Preferably, the pressure of the cycloaddition reaction is 1 to 10MPa, and may be, for example, 1MPa, 2MPa, 3MPa, 4MPa or 5 MPa.
Preferably, the temperature of the cycloaddition reaction is 60 to 150 ℃, for example, 80 ℃, 90 ℃, 100 ℃, 110 ℃, 120 ℃, 130 ℃, 140 ℃ or 150 ℃ and the like.
Preferably, the time of the cycloaddition reaction is 1 to 10 hours, for example, 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours or 8 hours, etc.
Compared with the prior art, the invention has the following beneficial effects:
the catalyst for synthesizing the cyclic carbonate is a catalyst with multi-site ionic liquid limited, and an active group R group of the ionic liquid and a halogen atom can generate a synergistic catalysis effect, so that the cyclic carbonate can be synthesized by efficiently and selectively catalyzing cycloaddition reaction under mild conditions without adding other auxiliary agents and catalysts. Compared with the same amount of bulk phase ionic liquid, the heterogeneous catalyst in the invention has higher catalytic activity and huge industrialization potential.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
In this example, a catalyst with a multi-site ionic liquid confined therein was prepared by the following method, and the specific test method was as follows:
using an ionic liquid of formula II [ IMCA ]]2Br2As a templating agent, tetraethyl orthosilicate was used as a silicon source.
First 0.056g of [ IMCA ]]2Br2(IL/Si ═ 0.2), 0.6g of 1,3, 5-trimethylbenzene and 2.6g of potassium chloride were added to 30ml of a 2mol/L hydrochloric acid solution. The mixed solution was stirred at room temperature for 2 hours, and then 2.08g of a silicon source was added to the solution. The mixture was stirred for 24h and then transferred to a hydrothermal kettle and held at 110 ℃ for 24h without stirring. And after the reaction is finished, cooling the mixed solution to room temperature, fully filtering the product, and drying the product in a vacuum drying oven at 80 ℃ for 24 hours. Through the synthesis steps, the catalyst with limited ionic liquid is prepared and named as 0.2[ IMCA]2Br2@mSiO2(H)。
Example 2
This example prepared a multi-site ionic liquid-limited catalyst by substituting only the mass of the ionic liquid added to example 1 with 0.112g (IL/Si ═ 0.4) and the resulting catalyst was named 0.4[ IMCA [ IMCA ] ] -0.4]2Br2@mSiO2(H)。
Example 3
This example prepared a multi-site ionic liquid-limited catalyst by substituting only the mass of the ionic liquid added to example 1 with 0.168g (IL/Si ═ 0.6) and the resulting catalyst was named 0.6[ IMCA [ IMCA ] ] -0.6]2Br2@mSiO2(H)。
Example 4
This example prepared a catalyst having a multi-site ionic liquid confined by replacing only the hydrochloric acid solution with deionized water and adjusting the pH of the solution to 8.5 using ammonia before adding the silicon source, the resulting catalyst being named 0.2[ IMCA ] by the method described in reference example 1]2Br2@mSiO2(OH)。
Example 5
This example prepared a domain-limited multi-site separation by the following methodCatalyst for subphase liquid, preparation method referring to example 4, the mass of the ionic liquid added was simply replaced with 0.112g (IL/Si ═ 0.4), and the resulting catalyst was named 0.4[ IMCA []2Br2@mSiO2(OH)。
Example 6
This example prepared a multi-site ionic liquid-limited catalyst by substituting the mass of the ionic liquid added to example 4 with 0.168g (IL/Si ═ 0.6) only and the resulting catalyst was named 0.6[ IMCA ═ 0.6 ]]2Br2@mSiO2(OH)。
Example 7
This example provides a method for preparing cyclic carbonates, the reaction scheme is as follows:
wherein T represents temperature, P represents pressure, and cat represents catalyst.
In a 25ml stainless steel reactor, 0.2[ IMCA ] was added]2Br2@mSiO2(H)250mg of 28.6mmol of propylene oxide, sealing the reaction kettle, filling carbon dioxide with proper pressure, controlling the temperature to slowly rise to 120 ℃ by a temperature controller, then controlling the pressure of the carbon dioxide to be 2.5MPa, and reacting for 8 hours to obtain a product propylene carbonate with the yield of 37.6%.
Example 8
This example differs from example 7 in that the catalyst used was 0.4[ IMCA ]]2Br2@mSiO2(H) And others are unchanged. The product cyclic carbonate was obtained in a yield of 46.7% propylene carbonate.
Example 9
This example differs from example 7 in that the catalyst used was 0.6[ IMCA ]]2Br2@mSiO2(H) And others are unchanged. The product cyclic carbonate was obtained in 83.0% yield of propylene carbonate.
Example 10
The difference between this example and example 7 is thatThe catalyst used was 0.2[ IMCA ]]2Br2@mSiO2(OH), others were unchanged. The product cyclic carbonate was obtained in a yield of 36.4% propylene carbonate.
Example 11
This example differs from example 7 in that the catalyst used was 0.4[ IMCA ]]2Br2@mSiO2(OH), others were unchanged. The product cyclic carbonate was obtained in 39.0% yield of propylene carbonate.
Example 12
This example differs from example 7 in that the catalyst used was 0.6[ IMCA ]]2Br2@mSiO2(OH), others were unchanged. The product cyclic carbonate was obtained in 28.5% yield of propylene carbonate.
Comparative example 1
This comparative example differs from example 7 in that the catalyst used is [ IMCA ]]2Br2The amount added was 4mg of the ionic liquid whose elemental analysis gave the limitation of the catalyst used in example 7, and the other was unchanged, giving propylene carbonate as a product with a yield of 23.5%.
Example 12
This comparative example differs from example 10 in that the catalyst used is [ IMCA ]]2Br2The amount of the ionic liquid added was 2.2mg, which was found by elemental analysis to be limited by the catalyst used in example 10, and the yield of propylene carbonate was 21.0% when the amount was unchanged.
The applicant states that the catalyst, the preparation method and the preparation method of the cyclic carbonate ester according to the present invention are described in the above examples, but the present invention is not limited to the above detailed methods, that is, the present invention is not meant to be implemented depending on the above detailed methods. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. A catalyst for the synthesis of cyclic carbonates, characterized in that it is a heterogeneous catalyst which confines a compound of formula i:
characterized in that R is1、R2、R3The halogen-free flame-retardant polyester resin is independently selected from hydrogen, substituted or unsubstituted C1-C20 straight chain or branched chain alkyl, carboxyl, hydroxyl, amino, sulfydryl and imino, n takes 1-4, and X is one of halogen.
2. The catalyst of claim 1, wherein the catalyst is any one of the following compounds:
3. the method for preparing the catalyst according to any one of claims 1 to 2, wherein the method for preparing the catalyst comprises: the multi-site ionic liquid in the formula I is used as a template agent, and tetraethyl orthosilicate is used as a silicon source. Synthesizing a confined catalyst which confines different amounts of ionic liquid by adjusting the ratio of ionic liquid to silicon source under different solvent environments, wherein the ranges of X, R and n are in accordance with claim 1.
4. The preparation method according to claim 3, wherein the mass ratio of the multi-site ionic liquid to the silicon source is 0.2-1.0.
5. The method of claim 3, wherein the solvent environment is one of an acidic or basic environment.
6. A method for preparing cyclic carbonate, the method comprising: performing cycloaddition reaction of carbon dioxide and epoxy compound in the presence of the catalyst of any one of claims 1-2 to obtain cyclic carbonate.
7. The method according to claim 6, wherein the epoxy compound is any one or a combination of at least two of ethylene oxide, propylene oxide, butylene oxide, epichlorohydrin, styrene oxide, cyclohexane oxide, and cyclopentane oxide.
8. The method according to claim 6, wherein the pressure of the cycloaddition reaction is 1 to 10 MPa.
9. The method according to claim 6, wherein the temperature of the cycloaddition reaction is 60 to 150 ℃.
10. The preparation method according to claim 6, wherein the time of the cycloaddition reaction is 1-10 h.
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