CN118165014A - Preparation method and application of ionic zinc catalyst - Google Patents

Preparation method and application of ionic zinc catalyst Download PDF

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CN118165014A
CN118165014A CN202410233767.2A CN202410233767A CN118165014A CN 118165014 A CN118165014 A CN 118165014A CN 202410233767 A CN202410233767 A CN 202410233767A CN 118165014 A CN118165014 A CN 118165014A
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znbr
mmol
zinc catalyst
preparation
carbon dioxide
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CN118165014B (en
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蒋秀燕
王丛丛
张海珍
黄现强
周迎梅
柏静
宗丽娜
孔凡厚
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Shandong Institute Of Petroleum And Chemical Engineering
Liaocheng University
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Liaocheng University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/06—Zinc compounds
    • 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
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2217—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
    • B01J2531/26—Zinc
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

The invention discloses a preparation method of an ionic zinc catalyst, which comprises the steps of placing salicylaldehyde, tetraethylenepentamine, zinc bromide and methanol into a round-bottom flask for reaction, filtering after the reaction is finished, and slowly volatilizing filtrate to obtain crystals of the ionic zinc catalyst. The method has the advantages of high reaction speed, simple reaction process, high purity of the obtained product and simple post-treatment. In the carbon dioxide cycloaddition reaction, the conversion rate is up to 99% and the selectivity is up to 99%.

Description

Preparation method and application of ionic zinc catalyst
Technical Field
The invention belongs to the technical field of catalyst material preparation, and relates to a preparation technology of an ionic zinc catalyst.
Technical Field
Carbon dioxide is a typical greenhouse gas. In recent years, excessive emission of carbon dioxide is a major cause of global warming. The capture and storage of carbon dioxide is therefore a focused area of attention by chemists. But its capture and storage in subterranean formations may lead to further geological and environmental degradation. Thus, one viable solution is to convert carbon dioxide into high value-added organic compounds. Among the numerous examples of catalytic carbon dioxide conversions, cycloaddition of carbon dioxide to cyclic carbonates is one of the most successful routes, and due to its wide application, cyclic carbonates can be used as electrolyte solvents for lithium ion batteries, excellent organic solvents and dye additives, and can replace many other toxic chemical agents. A variety of catalytic systems have been reported, such as alkali metal salts, onium salts, metal complexes, ionic liquids, metal oxides, and some supported catalysts, among others. However, most of the catalytic systems have the disadvantages of using halogen-containing catalysts, requiring co-catalysts or solvents, and the like, and further cause environmental pollution problem (Jianwen Li,et al,J.CO2 Util.69(2023)102384.Dr.Kazuto Takaishi,et al,Angew.Chem.Int.Ed.58(2019)9984-9988.),, so that the development of more green catalysts is of great significance from the environmental and economic viewpoints. Over the past several decades, advances have been made in the design and evaluation of both homogeneous and heterogeneous catalysts. Heterogeneous catalysts that are easily recovered and reused are favored in view of practical applications. The metal complex has attracted a great deal of attention as a catalyst for the cycloaddition reaction of CO 2 because of its special advantages of low cost, low toxicity, and capability of adjusting the structure according to specific requirements.
Based on the above documents, according to the development concept of green chemistry, it is necessary to design an environment-friendly ionic zinc high-efficiency catalytic system for generating cyclic carbonate by cycloaddition of carbon dioxide.
By searching, no published patent documents related to the present application have been found.
Disclosure of Invention
The invention aims at solving the problems of halogen, large catalyst dosage and the like in a catalyst in a catalytic conversion carbon dioxide cycloaddition reaction. The preparation method of the ionic zinc catalyst single-component catalyst is synthesized by a one-pot method, so that the synergistic catalysis effect is expected to be achieved in the carbon dioxide cycloaddition reaction, and the aim of realizing the carbon dioxide cycloaddition under the action of a low-quantity single-component catalyst is fulfilled.
The design idea of the invention is as follows:
1. In-situ synthesizing zinc halide and organic ligand by a one-pot method to construct zinc complex, and synergistically catalyzing carbon dioxide cycloaddition at multiple active sites in the reaction process;
2. The zinc halide, salicylaldehyde and tetraethylenepentamine are reacted under the action of methanol to synthesize an ionic multi-site catalyst, wherein [ ZnBr 4]2- active site in the catalyst plays a role in ring opening of epoxy compound in the catalytic process, and N active site in the ligand is used for absorbing carbon dioxide;
3. The ionic multi-site single-component catalyst with a definite structure is applied to the cycloaddition reaction of carbon dioxide, so that the aim of obtaining the cyclic carbonate with high conversion rate and high selectivity of carbon dioxide is fulfilled.
The crystal structure information of such catalysts is obtained by the following method:
the crystal of the ionic multi-site single-component catalyst is synthesized by a conventional solvothermal method, and the specific description experiment method is as follows:
Sequentially adding salicylaldehyde and tetraethylenepentamine into a clean round-bottom flask, mixing with a solvent, refluxing and stirring at 60-100 ℃ for 2-6h, then adding zinc halide, stirring for 2h, filtering while the mixture is hot, and standing the filtrate at room temperature for 2-4 weeks to slowly volatilize. The [ Zn 2(L)]2[ZnBr4]·4CH3 OH ] was obtained in about 30-50% yield.
The preferred scheme is that salicylaldehyde: tetraethylenepentamine: the ratio of Zn (OAc) 2 mass is 0.5-2.5:0.17-0.85:0.33-1.65, and the solvent is methanol.
The product is characterized by single crystal X-ray diffraction and powder X-ray diffraction, and accurate information about a crystal structure is obtained. The specific results are as follows:
The molecular formula of the crystal is [ Zn 2(L)]2[ZnBr4]·4CH3 OH, wherein the cationic part is binuclear Zn2 unit located at the center of the positive ion structure frame, and two different coordination modes are observed by Zn atoms due to the flexibility of N5O3 ligand and the existence of a plurality of coordination sites. The anions are [ ZnBr 4]2- units, and the two are combined together through electrostatic attraction interaction of anions and cations. Structural analysis shows that the catalyst contains two active centers, one is [ ZnBr 4]2- active site and one is binuclear Zn2 unit active site, both of which contribute to the carbon dioxide cycloaddition reaction, [ ZnBr 4]2- can provide an environment for ring opening of epoxy compounds, and the binuclear Zn2 unit provides a catalytic center for the carbon dioxide cycloaddition reaction and is expected to play a role in synergistic catalysis.
The invention mainly synthesizes a carbon dioxide cycloaddition ionic zinc single-component catalyst, which is applied to a carbon dioxide cycloaddition reaction. The catalyst can realize carbon dioxide cycloaddition reaction under the condition of no solvent and no catalyst promoter, the conversion rate is up to 99%, and the selectivity is up to 100%. The preparation method of the catalyst has simple reaction process.
The cyclic compound is epichlorohydrin, epibromohydrin, epoxystyrene, etc., and the conversion rate and selectivity are detected by gas chromatography.
The invention aims at realizing the following technical scheme:
The molecular structure is as follows:
The molecular formula is: [ Zn 2(L)]2[ZnBr4]·4CH3 OH
The invention provides a single-component double-active-center catalyst which has the following characteristics:
1. The preparation method is simple, and the catalyst has a definite molecular structure, thereby being beneficial to researching the catalytic reaction mechanism.
2. The catalyst has [ ZnBr4] 2- and binuclear Zn2 unit active sites, and can play a role in synergistic catalysis on cycloaddition of carbon dioxide.
Drawings
FIG. 1. Schematic crystal structure of compound [ Zn 2(L)]2[ZnBr4]·4CH3 OH (hydrogen atoms and water solvent molecules removed for structural clarity);
FIG. 2-RXRD characterization of the compound [ Zn 2(L)]2[ZnBr4]·4CH3 OH, upper panel, synthetic sample, lower panel, simulated sample.
Table 2. Results of cycloaddition of the compound [ Zn 2(L)]2[ZnBr4]·4CH3 OH to carbon dioxide.
Detailed Description
Specific example 1: preparation of Compound [ Zn 2(L)]2[ZnBr4]·4CH3 OH ]
To a clean round bottom flask was added salicylaldehyde (2.5 mmol) and tetraethylenepentamine (0.85 mmol) in sequence, mixed with MeOH (10 mL), stirred at 80℃under reflux for 4h, then zinc bromide (1.65 mmol) was added, stirred for 2h again, filtered while hot and the resulting solution was allowed to stand at room temperature for 2 weeks to give [ Zn 2(L)]2[ZnBr4]·4CH3 OH. The yield was 50%.
Specific example 2: preparation of Compound [ Zn 2(L)]2[ZnBr4]·4CH3 OH ]
To a clean round bottom flask was added salicylaldehyde (2.5 mmol) and tetraethylenepentamine (0.68 mmol) in sequence, mixed with MeOH (10 mL), stirred at 80℃under reflux for 4h, then zinc bromide (1.65 mmol) was added, stirred for 2h again, filtered while hot and the resulting solution was allowed to stand at room temperature for 3 weeks to give [ Zn 2(L)]2[ZnBr4]·4CH3 OH. The yield thereof was found to be 37%.
Specific example 3: preparation of Compound [ Zn 2(L)]2[ZnBr4]·4CH3 OH ]
To a clean round bottom flask was added salicylaldehyde (2 mmol) and tetraethylenepentamine (0.68 mmol) in sequence, mixed with MeOH (10 mL), stirred at 80℃under reflux for 4h, then zinc bromide (1.65 mmol) was added, stirred for 2h again, filtered while hot and the resulting solution was allowed to stand at room temperature for 4 weeks to give [ Zn 2(L)]2[ZnBr4]·4CH3 OH. The yield was 30%.
Specific example 4: preparation of Compound [ Zn 2(L)]2[ZnBr4]·4CH3 OH ]
To a clean round bottom flask was added salicylaldehyde (0.50 mmol) and tetraethylenepentamine (0.17 mmol) in sequence, mixed with MeOH (10 mL), stirred at 80℃under reflux for 4h, then zinc bromide (0.11 mmol) was added, stirred for 2h, filtered while hot and the resulting solution was allowed to stand at room temperature for 4 weeks to give [ Zn 2(L)]2[ZnBr4]·4CH3 OH. The yield was 32%.
Specific example 5: preparation of Compound [ Zn 2(L)]2[ZnBr4]·4CH3 OH ]
To a clean round bottom flask was added salicylaldehyde (2.5 mmol) and tetraethylenepentamine (0.68 mmol) in sequence, mixed with MeOH (10 mL), stirred at 80℃under reflux for 4h, then zinc bromide (0.55 mmol) was added, stirred for 2h again, filtered while hot and the resulting solution was allowed to stand at room temperature for 4 weeks to give [ Zn 2(L)]2[ZnBr4]·4CH3 OH. The yield was 38%.
Specific example 6: preparation of Compound [ Zn 2(L)]2[ZnBr4]·4CH3 OH ]
To a clean round bottom flask was added sequentially salicylaldehyde (2 mmol) and tetraethylenepentamine (0.68 mmol) and MeOH (10 mL), mixed at 80℃under reflux for 4h, then zinc bromide (1.65 mmol) was added, stirred for 2h, filtered while hot and the resulting solution was allowed to stand at room temperature for 2 weeks to give [ Zn 2(L)]2[ZnBr4]·4CH3 OH. The yield was 43%.
Specific example 7: preparation of Compound [ Zn 2(L)]2[ZnBr4]·4CH3 OH ]
To a clean round bottom flask was added salicylaldehyde (2.5 mmol) and tetraethylenepentamine (0.85 mmol) in sequence, mixed with MeOH (10 mL), stirred at 100deg.C under reflux for 4h, then zinc bromide (1.65 mmol) was added, stirred for 2h, filtered while hot and the resulting solution was allowed to stand at room temperature for 2 weeks to give [ Zn 2(L)]2[ZnBr4]·4CH3 OH. The yield thereof was found to be 39%.
Specific example 8: preparation of Compound [ Zn 2(L)]2[ZnBr4]·4CH3 OH ]
To a clean round bottom flask was added salicylaldehyde (2.5 mmol) and tetraethylenepentamine (0.85 mmol) in sequence, mixed with MeOH (10 mL), stirred at 60℃under reflux for 4h, then zinc bromide (1.65 mmol) was added, stirred for 2h again, filtered while hot and the resulting solution was allowed to stand at room temperature for 3 weeks to give [ Zn 2(L)]2[ZnBr4]·4CH3 OH. The yield was 42%.
Specific example 9: preparation of Compound [ Zn 2(L)]2[ZnBr4]·4CH3 OH ]
To a clean round bottom flask was added salicylaldehyde (2.5 mmol) and tetraethylenepentamine (0.85 mmol) in sequence, mixed with MeOH (10 mL), stirred at 80℃under reflux for 2h, then zinc bromide (1.65 mmol) was added, stirred for 2h again, filtered while hot and the resulting solution was allowed to stand at room temperature for 2 weeks to give [ Zn 2(L)]2[ZnBr4]·4CH3 OH. The yield was 45%.
Specific example 10: preparation of Compound [ Zn 2(L)]2[ZnBr4]·4CH3 OH ]
To a clean round bottom flask was added salicylaldehyde (2.5 mmol) and tetraethylenepentamine (0.85 mmol) in sequence, mixed with MeOH (10 mL), stirred at 80℃under reflux for 6h, then zinc bromide (1.65 mmol) was added, stirred for 2h again, filtered while hot and the resulting solution was allowed to stand at room temperature for 2 weeks to give [ Zn 2(L)]2[ZnBr4]·4CH3 OH. The yield was 50%.
As shown in Table 1, the crystallographic data of the compound [ [ Zn 2(L)]2[ZnBr4]·4CH3 OH ]
Specific example 11: application of ionic zinc catalyst single-component catalyst to carbon dioxide cycloaddition reaction
Examples:
Placing 5mmol of epoxy compound in a20 mL reaction kettle, adding 0.05mmol of catalyst, introducing 2MPa of carbon dioxide, heating and stirring at 100 ℃, reacting for 4 hours, detecting by gas chromatography, wherein almost all epoxy compound in the reaction liquid is converted into cyclic carbonate, and the specific data are shown in Table 2. The cycloaddition reaction result of the compound [ Zn2 (L) ]2[ ZnBr4 ]. 4CH3OH to the epoxy compound is shown as follows:

Claims (4)

1. A preparation method of an ionic zinc catalyst is characterized in that: the method comprises the following steps: sequentially adding salicylaldehyde and tetraethylenepentamine into a clean round-bottom flask, mixing with a solvent, refluxing and stirring at a certain temperature, then adding zinc halide, stirring for 2 hours, filtering while the mixture is hot, and standing the filtrate at room temperature for 2-4 weeks to slowly volatilize to obtain [ Zn 2(L)]2[ZnBr4]·4CH3 OH ].
2. The method for preparing the ionic zinc catalyst according to claim 1, wherein the method comprises the following steps: salicylaldehyde: tetraethylenepentamine: the ratio of Zn (OAc) 2 mass is 0.5-2.5:0.17-0.85:0.33-1.65, the solvent is methanol, the reaction temperature is 60-100 ℃, and the reflux stirring time is 2-6 h.
3. The method for preparing the ionic zinc catalyst according to claim 1, wherein the method comprises the following steps: molecular structure of the ionic zinc catalyst:
4. Use of an ionic zinc catalyst obtained by the process of any one of claims 1 to 3 for catalyzing a carbon dioxide cycloaddition reaction.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN118619977A (en) * 2024-08-09 2024-09-10 山东石油化工学院 Preparation method and application of ionic copper/zinc catalyst

Citations (3)

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CN104496959A (en) * 2015-01-09 2015-04-08 南开大学 Method for preparing cyclic carbonate by reacting normal pressure carbon dioxide with epoxide
CN109824705A (en) * 2019-02-28 2019-05-31 滨州学院 A kind of preparation method and its usage of bis- (N- (4- carboxyl) phenyl) acid imide Zn complex catalyst

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
US6870004B1 (en) * 2001-08-24 2005-03-22 Northwestern University Metal-ligand complexes and related methods of chemical CO2 fixation
CN104496959A (en) * 2015-01-09 2015-04-08 南开大学 Method for preparing cyclic carbonate by reacting normal pressure carbon dioxide with epoxide
CN109824705A (en) * 2019-02-28 2019-05-31 滨州学院 A kind of preparation method and its usage of bis- (N- (4- carboxyl) phenyl) acid imide Zn complex catalyst

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN118619977A (en) * 2024-08-09 2024-09-10 山东石油化工学院 Preparation method and application of ionic copper/zinc catalyst
CN118619977B (en) * 2024-08-09 2024-10-18 山东石油化工学院 Preparation method and application of ionic copper/zinc catalyst

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