CN117447439A - Method for synthesizing cyclic carbonate by catalyzing multi-stage structure polyion liquid - Google Patents

Method for synthesizing cyclic carbonate by catalyzing multi-stage structure polyion liquid Download PDF

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CN117447439A
CN117447439A CN202311399318.7A CN202311399318A CN117447439A CN 117447439 A CN117447439 A CN 117447439A CN 202311399318 A CN202311399318 A CN 202311399318A CN 117447439 A CN117447439 A CN 117447439A
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catalyst
reaction
liquid
formula
cyclic carbonate
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成卫国
苏倩
赵茜萌
付梦倩
许振洋
刘�文
杨子锋
张锁江
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Huizhou Green Energy And New Materials Research Institute
Institute of Process Engineering of CAS
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Huizhou Green Energy And New Materials Research Institute
Institute of Process Engineering of CAS
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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
    • 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
    • B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • 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
    • C07D317/38—Ethylene carbonate

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

The invention provides a method for synthesizing cyclic carbonate by multi-stage structure polyion liquid catalysis, which comprises the following steps: preparation of multi-stage structure polyion liquid catalyst and catalytic CO 2 And synthesizing the cyclic carbonate through cycloaddition reaction with an epoxy compound. The preparation method provided by the invention adjusts the multi-stage structure of the polymerized polyionic liquid through the ionic liquid monomer structure design, so that the catalyst with high activity, high stability and easy separation can be obtained, and various epoxy compounds and CO can be catalyzed 2 The cycloaddition reaction occurs, so that the method has the advantages of high reaction efficiency, less catalyst consumption, simple preparation process and easy separation, and has higher industrial application value.

Description

Method for synthesizing cyclic carbonate by catalyzing multi-stage structure polyion liquid
Technical Field
The invention belongs to the technical field of green catalysis, and relates to a polyion liquid used as an efficient catalyst for catalyzing CO 2 And the method for synthesizing the cyclic carbonate by the epoxy compound is to copolymerize the imidazole ionic liquid and the divinylbenzene cross-linking agent, and realize the purpose of regulating and controlling the multi-stage structure of the polyionic liquid to enhance the stability and activity of the catalyst by regulating the anion type, the chain length of a side chain and the substituent group of the imidazole ionic liquid and the proportion of the imidazole ionic liquid and the divinylbenzene. The specific catalytic reaction is CO 2 And epoxy compound, the reaction temperature is 80-150 ℃, the reaction pressure is 1-5 MPa, the reaction time is 1-8 h, and the catalyst dosage is 0.1-10 wt%. The synthesis method has the advantages of high reaction efficiency, simple catalyst preparation process, small catalyst consumption and easy separation and reuse.
Background
CO 2 As a C1 resource rich in greenhouse gases and sources, efficient capture and conversion is a global strategic issue. Cyclic carbonates are very widely used aprotic, high boiling polar solvents, which can serve as electrolytes in lithium ion batteries, as well as for the synthesis of pharmaceutical and fine chemical intermediates. CO 2 The cycloaddition reaction for synthesizing the cyclic carbonate is a green sustainable route with both environmental benefit and economic benefit, and the currently reported catalysts for synthesizing the cyclic carbonate mainly comprise organic catalysts, ionic liquid (CN 111362901A), metal-organic frameworks (MOFs) (CN 111454434A, CN 105481821A), porous organic polymers (CN 104667974B), transition metal complexes (CN 107827857A, CN107827858A, CN 111215148A), composite catalysts (CN 111393402A, CN 107715918B) and the like. Wherein, homogeneous catalysisThe catalyst has high catalytic activity, but the separation process is relatively complex and the catalyst stability is poor. Although heterogeneous catalysts simplify the separation process, the catalytic activity is relatively low. Therefore, development of heterogeneous catalysts which are efficient, stable and easy to separate is of more interest.
As a novel green nonmetallic medium, the ionic liquid is widely used in the field of catalysis due to its structural design, good stability and solubility. The ionic liquid can have higher activity than the traditional catalyst through anion-cation design. CN101130537 discloses a method for preparing cyclic carbonate from hydroxyl ionic liquid. The hydroxyl is found to be taken as a hydrogen bond donor to promote the activation of epoxide, and CO can be efficiently catalyzed under mild conditions 2 And (3) transformation. The ionic liquid immobilization can effectively simplify separation, and CN102391241A discloses a method for preparing cyclic carbonate by using a chitosan supported catalyst, wherein the chitosan chemically supported catalyst is used in the reaction process, so that CO can be effectively catalyzed 2 And (3) transformation. The synergistic catalysis based on the hydroxyl groups in the carrier enables the efficient and highly selective catalytic synthesis of cyclic carbonates without the need for the addition of further auxiliary agents and cocatalysts. However, the existence of the carrier causes certain interface mass transfer steric hindrance, and the free movement of ions is limited by interface constraint, so that the effective collision between the reaction molecules and the active site is reduced, and the activity of the immobilized ionic liquid is often lower than that of the equivalent ionic liquid.
The polyionic liquid is a special polymer with an ionic liquid unit structure, has stronger stability compared with ionic liquid monomers, has better structural ductility and adjustability compared with immobilized ionic liquid, and can provide better flexibility of active sites by expanding the unit structure. CN109134420a discloses a heterogeneous polymeric ionic liquid for high efficiency catalysis of CO 2 And a process for synthesizing a cyclic carbonate from an epoxide. The quaternary ammonium ionic liquid monomer is synthesized into a heterogeneous catalyst through free radical polymerization. The catalyst is easy to separate, has good activity and can effectively catalyze CO 2 And epoxide synthesis of cyclic carbonates. CN112341394a discloses a hydrogen bond donor functionalized polyionic liquid catalystThe preparation method is characterized in that the imidazole-based ionic liquid monomer and the hydrogen bond donor monomer are polymerized according to a certain proportion, the presence of the hydrogen bond donor greatly improves the catalytic efficiency, and a thought is provided for the regulation and control of the high activity of the polyion liquid. However, the conventional research is seldom compatible with the regulation and control of polyionic liquid molecules and nano-microstructures, so that the polyionic liquid catalyst with both stability and activity is difficult to obtain.
The polyion liquid catalyst with different structures is prepared by copolymerization, cross-linking and polymerization of one or two imidazolyl ionic liquid monomers and a rigid divinylbenzene cross-linking agent. The intrinsic catalytic activity is improved from the molecular level by the ion liquid monomer anion modulation and the hydrogen supply group introduction; through the regulation and control of the chain length of the side chain of the ionic liquid monomer and the proportion of the cross-linking agent, the spatial structure of the polyionic liquid is regulated and controlled from the nano-micro level, so that the stability of the ionic liquid structure is enhanced, and the active sites are fully dispersed and exposed.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a method for synthesizing cyclic carbonate by using polyion liquid catalysis, which has stability and activity, so as to develop the potential of a heterogeneous catalyst in the industrial application of the cyclic carbonate.
To achieve the object, a first object of the present invention is to provide a polyionic liquid catalyst of multistage structure, with which CO is catalyzed 2 And an epoxy compound, the preparation method comprising the following steps:
the multi-stage structure polyionic liquid has a structure shown in a formula I, and the preparation process of the multi-stage structure of the polyionic liquid is shown in a formula II:
wherein m, n and l respectively represent the number of different monomers in the unit structure, and are usually the ratio of the addition amounts of the three monomers in the polymerization reaction, and each is independently selected from any natural number;
R 1 selected from a hydrogen atom or any one of the alkyl groups, such as methyl;
R 2 selected from any hydrogen donating group such as hydroxy;
j. k represents the number of carbon atoms of the alkyl chain, and the number of carbon atoms in j and k are each independently selected from: 2 to 12.
X 1 And X 2 Each independently selected from any one of fluoride ion, chloride ion, bromide ion and iodide ion.
The invention utilizes the advantages of the unit structure of the polyion liquid that the polyion liquid is rich in active ions and the multistage structure enhances the mass transfer of the reaction, and is beneficial to improving the efficiency of catalyzing cycloaddition reaction, thereby ensuring that the cycloaddition reaction condition is relatively mild.
Preferably, the reaction temperature of the addition reaction is 80 to 150 ℃, for example, 85 ℃, 90 ℃, 95 ℃, 100 ℃, 105 ℃, 115 ℃, 125 ℃, 135 ℃, 145 ℃, or the like.
Preferably, the reaction pressure of the addition reaction is 1 to 5MPa, for example, 1.5MPa, 1.8MPa, 2.0MPa, 2.5MPa, 3.2MPa, 3.5MPa, 4.0MPa, 4.5MPa, or the like.
Preferably, the reaction time of the addition reaction is 1 to 8 hours, for example, 1 hour, 1.5 hours, 2 hours, 2.5 hours, 3 hours, 3.5 hours, 4 hours, 4.5 hours, 5 hours, 5.5 hours, 6 hours, 6.5 hours, 7 hours, 7.5 hours, and the like.
Preferably, the particle size of the catalyst is 10 to 500nm, for example 10nm, 20nm, 30nm, 40nm, 50nm, 100nm, 150nm, 200nm, 250nm, 300nm, etc., and the suitable catalyst particle size is advantageous for the dispersion of the active sites, thereby improving the catalytic efficiency.
Preferably, the catalyst mass fraction is 0.1 to 10%, for example, 0.1%, 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, etc.
Preferably, the epoxy-containing compound is any one or a mixture of at least two of ethylene oxide, propylene oxide, butylene oxide, epichlorohydrin, styrene oxide, cyclohexane oxide or cyclopentane oxide.
Preferably, in the structure shown in the formula I, m+n is less than or equal to 136, and the catalytic efficiency is easily reduced due to the excessively high polymerization degree.
Preferably, in the structure shown in formula one, R 1 An alkane group with a carbon number less than or equal to 16 selected from hydrogen atom, methyl, ethyl, propyl, butyl and the like
Preferably, in the structure shown in formula one, R 2 Any one of hydroxyl, amino, carboxyl and thiol groups.
Preferably, in the structure shown in formula one, X 1 And X 2 Each independently selected from any one of fluoride ion, chloride ion, bromide ion and iodide ion.
Preferably, in the structure shown in formula one, the number ratio of carbon atoms in m, n, l is 2:3:0, 1:1:0, 0:3:2, 0:1:1, 1:3:1, 1:3:2, 2:3:1.
Preferably, in the structure shown in formula one, the number of carbon atoms in j, k are each independently selected from: 2 to 12.
Preferably, the preparation method comprises the following steps:
placing the catalyst powder containing epoxy compound and having the particle size of 10-500 nm into a closed reaction kettle, uniformly mixing, maintaining the temperature of the reaction kettle within the range of 80-150 ℃, and continuously introducing CO into the reaction kettle 2 And (3) carrying out addition reaction for 1-8 h by maintaining the pressure of a reaction system in the kettle within the range of 1-5 MPa to obtain the cyclic carbonate.
The numerical ranges recited herein include not only the above-listed point values, but also any point values between the above-listed numerical ranges that are not listed, and are limited in space and for the sake of brevity, the present invention is not intended to be exhaustive of the specific point values that the stated ranges include.
Compared with the prior art, the invention has the beneficial effects that:
(1) The invention provides a multi-stage structure polyionic liquid catalyst which is used for catalyzing CO 2 The cyclic carbonate synthesized by cycloaddition with the epoxy compound has higher selectivity and conversion rate, and the yield of the obtained cyclic carbonate can reach 99m percent.
(2) Compared with the traditional method for synthesizing the cyclic carbonate, the polyion liquid catalyst used in the invention has the advantages of high active site utilization rate, less consumption, high catalytic efficiency, stability, difficult decomposition, simple preparation process, easy product separation and the like, and has higher industrialized application value.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments.
The polyionic liquids used in the following examples and comparative examples can be obtained by self-synthesis.
Illustratively, the polyionic liquid may be synthesized by the steps of:
and (1) adding a certain amount of vinyl imidazole monomer and bromoethane into a 250mL flask, condensing and refluxing for 24 hours at 70 ℃, pouring out unreacted liquid at the upper layer after the reaction is finished, adding acetonitrile, condensing and refluxing for 4 hours at 80 ℃, and freezing the reaction liquid for 24 hours. The crude product is obtained by reduced pressure distillation, washed three times with ethyl acetate and finally dried in a vacuum drying oven at 50 ℃ for 48 hours to obtain the ionic liquid monomer.
And (2) adding a certain amount of the ionic liquid monomer synthesized in the step (1) and a certain proportion of Divinylbenzene (DVB), 50mL of acetonitrile into a 100mL three-neck flask, stirring for 1h, and then adding a certain proportion of azo-diisobutylnitrile (AIBN). By Schlenk technique with N 2 Air is replaced, and then the temperature is raised to the specified temperature for reaction for 24 hours, so as to obtain a crude product. Repeatedly washing with water and ethanol for 3 times, and vacuum drying at 50deg.C for 24 hr to obtain white powder polyion liquid.
By changing the ratio of the ionic liquid monomer to the DVB cross-linking agent, the chain length and substituent groups of the ionic liquid monomer, replacing bromoethanol with other types of compounds or changing the addition amount of an initiator, a series of polyionic liquids with different multi-stage structures can be obtained by a person skilled in the art. The polyion liquid catalyst with multilevel pore channels, which has higher micropore proportion and smaller particle size, can be obtained by regulating the proportion of the ionic liquid monomer and the DVB cross-linking agent, so that the catalytic activity is improved by using the dispersion of active sites; the polyion liquid catalyst with smaller particle size and easy swelling can be obtained through chain length regulation of the ionic liquid monomer, so that the catalytic activity is improved by using the exposure of active sites; the introduction of the hydrogen-supplying group of the ionic liquid monomer is beneficial to enhancing the intrinsic activity of the unit structure of the polyionic liquid, thereby improving the catalytic performance.
In the examples of the present invention, the yield of the product was quantitatively determined by an Agilent model 7890B gas chromatograph manufactured by Agilent corporation.
Example 1
And (2) placing polyion liquid 1 powder (prepared by ethyl vinyl imidazole ionic liquid and DVB with the proportion (n: m) =0.4) of 0.034mol of propylene oxide and 2mol% of propylene oxide content into a 250mL sealed reaction kettle, uniformly mixing, maintaining the temperature of the reaction kettle at 120 ℃, continuously introducing carbon dioxide gas into the reaction kettle, maintaining the pressure of a reaction system in the kettle at 2.5MPa, and carrying out addition reaction for 2h to obtain the propylene carbonate product, wherein the yield of the propylene carbonate is 95mol%.
The polyionic liquid 1 has a structure as shown in a compound 1: specific surface area 157.8m 2 Per gram, micropore area 49.8m 2 And/g, particle size 15nm.
Example 2
The only difference from example 1 is that the n: m is replaced by 0.5, resulting in polyionic liquid 2. 130.1m 2 /g，30.9m 2 And/g, particle size of 50-270 nm. Example 2 gives the product propylene carbonate with a yield of 86mol%.
Example 3
The only difference from example 1 is that the propylene oxide is replaced by ethylene oxide and example 3 gives the product ethylene carbonate with a yield of 94mol%.
Example 4
The only difference from example 1 is that polyionic liquid 1 is replaced by polyionic liquid 3 (ethyl vinyl imidazole ionic liquid is replaced by butyl vinyl imidazole ionic liquid, i.e. j=3), and the ionic liquid content in the polyionic liquid is 1mol% propylene oxide.
Example 4 gives the product propylene carbonate with a yield of 96mol%.
The ionic liquid polymer 3 has a structure as shown in compound 3: particle size 50nm and swelling degree 4.1.
Example 5
The only difference from example 4 is that j is replaced by 7, the resulting polyionic liquid 4. Particle size 50nm and swelling degree 2.7. Example 5 gives the product propylene carbonate with a yield of 95mol%.
Example 6
The only difference from example 4 is that the propylene oxide is replaced by ethylene oxide and example 6 gives the product ethylene carbonate with a yield of 93mol%.
Example 7
The only difference from example 1 is that the polyionic liquid 1 is replaced by polyionic liquid 5 (j=11 and hydroxyethyl imidazole ionic liquid monomer is introduced, i.e. R 2 -OH), the reaction time 2h was replaced by 1h.
Example 7 gives the product propylene carbonate with a yield of 96mol%.
The polyionic liquid 5 has a structure as shown in the compound 5: the grain diameter is 200-400 nm.
Example 8
The only difference from example 7 is that the polyionic liquid 5 is replaced with polyionic liquid 6 (R 2 -COOH), and the grain diameter is 200-400 nm. Example 8 gives the product propylene carbonate with a yield of 96mol%.
Example 9
The only difference from example 7 is that the polyionic liquid 6 is replaced by a polyionIonic liquid 7 (R) 2 is-NH 2 ) Particle size is 200-400 nm. Example 9 gives the product propylene carbonate with a yield of 95mol%.
Example 10
The only difference from example 9 is that the propylene oxide is replaced by ethylene oxide and example 10 gives the product ethylene carbonate with a yield of 99mol%.
In summary, the invention provides a method for synthesizing cyclic carbonate by multi-stage structure polyion liquid catalysis. The prepared multi-stage structure polyionic liquid catalyst is used for catalyzing CO 2 The cyclic carbonate synthesized by cycloaddition with the epoxy compound has higher selectivity and conversion rate, and the yield of the obtained cyclic carbonate can reach 99m percent. Compared with the traditional method for synthesizing the cyclic carbonate, the polyion liquid catalyst used in the invention has the advantages of high active site utilization rate, less consumption, high catalytic efficiency, stability, difficult decomposition, simple preparation process, easy product separation and the like, and has higher industrialized application value.
While the foregoing is directed to embodiments of the present invention, other and further details of the invention may be had by the present invention, it should be understood that the foregoing description is merely illustrative of the present invention and that no limitations are intended to the scope of the invention, except insofar as modifications, equivalents, improvements or modifications are within the spirit and principles of the invention.

Claims (11)

1. The method for synthesizing the cyclic carbonate by using the polyion liquid is characterized by comprising the following steps of: CO 2 Carrying out cycloaddition reaction with epoxy compound under the catalysis of catalyst to obtain cyclic carbonate; the catalyst is polyion liquid; the polyionic liquid has a structure shown in a formula I:
wherein m, n and l respectively represent the number of different monomers in the unit structure and are each independently selected from any natural number;
R 1 selected from a hydrogen atom or any one of the alkyl groups, such as methyl;
R 2 selected from any hydrogen donating group such as hydroxy;
wherein j and k represent the number of carbon atoms of the alkyl chain, and each of them independently selects an arbitrary natural number.
2. The method of claim 1, wherein the cycloaddition reaction temperature is 80-150 ℃; the reaction pressure is 1-5 MPa; the reaction time is 1-8 h; the mass fraction of the catalyst is 0.1-10%.
3. The method according to claim 1, wherein the catalyst has a particle size of 10 to 500nm.
4. The method according to claim 1, wherein the epoxy compound is any one or a mixture of at least two of ethylene oxide, propylene oxide, butylene oxide, epichlorohydrin, styrene oxide, cyclohexane oxide, and cyclopentane oxide.
5. The method according to claim 1, wherein m+n.ltoreq.136 in the structure represented by formula one.
6. The process of claim 1, wherein R is in the structure of formula I 1 Independently selected from a hydrogen atom or any one of the alkyl groups, such as methyl;
preferably, R 1 Independently selected from hydrogen atom or any one of alkyl groups with the carbon number less than or equal to 16, such as methyl, ethyl, propyl, butyl and the like.
7. The process of claim 1, wherein R is in the structure of formula I 2 Independently selected from any one ofHydrogen-donating groups such as hydroxy;
preferably, R 2 Independently selected from any one of hydroxyl, amino, carboxyl and thiol groups.
8. The process according to claim 7, wherein X is represented by formula I 1 And X 2 Each independently selected from any one of fluoride ion, chloride ion, bromide ion and iodide ion.
9. The method according to claim 8, wherein in the structure represented by formula one, the number of carbon atoms in m, n, and l is any natural number;
preferably, the number ratio of carbon atoms in m, n, l is 2:3:0, 1:1:0, 0:3:2, 0:1:1, 1:3:1, 1:3:2, 2:3:1.
10. The method according to claim 9, wherein in the structure represented by formula one, the number of carbon atoms in j and k is any natural number;
preferably, the number of carbon atoms in j, k are each independently selected from: 2 to 12.
11. The preparation method according to one of the claims 9, characterized in that the preparation method comprises the steps of:
placing the catalyst powder containing epoxy compound and having the particle size of 10-500 nm into a closed reaction kettle, uniformly mixing, maintaining the temperature of the reaction kettle within the range of 80-150 ℃, and continuously introducing CO into the reaction kettle 2 And (3) carrying out addition reaction for 1-8 h by maintaining the pressure of a reaction system in the kettle within the range of 1-5 MPa to obtain the cyclic carbonate.
CN202311399318.7A 2023-10-26 2023-10-26 Method for synthesizing cyclic carbonate by catalyzing multi-stage structure polyion liquid Pending CN117447439A (en)

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