CN111068786A - Alkaline functionalized F-Mn-MOF-74 nano catalytic material for efficiently catalyzing carbon dioxide cycloaddition reaction - Google Patents

Alkaline functionalized F-Mn-MOF-74 nano catalytic material for efficiently catalyzing carbon dioxide cycloaddition reaction Download PDF

Info

Publication number
CN111068786A
CN111068786A CN201911348418.0A CN201911348418A CN111068786A CN 111068786 A CN111068786 A CN 111068786A CN 201911348418 A CN201911348418 A CN 201911348418A CN 111068786 A CN111068786 A CN 111068786A
Authority
CN
China
Prior art keywords
mof
reaction
functionalized
carbon dioxide
catalytic material
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201911348418.0A
Other languages
Chinese (zh)
Inventor
王吉德
冯超
郭媛
谢月洪
曹向磊
张莉
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Xinjiang University
Original Assignee
Xinjiang University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Xinjiang University filed Critical Xinjiang University
Priority to CN201911348418.0A priority Critical patent/CN111068786A/en
Publication of CN111068786A publication Critical patent/CN111068786A/en
Pending legal-status Critical Current

Links

Images

Classifications

    • 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
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/008—Supramolecular polymers
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0213—Complexes 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
    • B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
    • B01J2531/72—Manganese

Landscapes

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

Abstract

The invention discloses a preparation method of a nano-scale alkaline functionalized F-Mn-MOF-74 catalytic material and a cycloaddition reaction for efficiently catalyzing carbon dioxide and epoxide. Adenine or dimethyl imidazole is used as an alkali source and a competitive ligand to be introduced into the synthesis of Mn-MOF-74, lone pair electrons on a nitrogen atom in adenine or dimethyl imidazole can have a competitive coordination effect with 2,5 dihydroxy terephthalic acid, and the F-Mn-MOF-74 crystal with nanoscale functionalization is prepared by adopting a solvothermal method. Adenine or dimethyl imidazole not only serves as a competitive ligand to change the crystal form of Mn-MOF-74, but also serves as a source of Lewis basic sites to improve the catalytic activity of the nanoscale basic functionalized F-Mn-MOF-74 catalytic material in the cycloaddition reaction of carbon dioxide and epoxide. The nano-scale alkaline functionalized F-Mn-MOF-74 catalytic material synthesized by a solvothermal method catalyzes a cycloaddition reaction under the reaction conditions that the reaction temperature is 70-130 ℃, the reaction pressure is 3-19 bar, the reaction time is 2-14h, and the addition amount of a catalyst is 1-30mg, and has excellent catalytic performance.

Description

Alkaline functionalized F-Mn-MOF-74 nano catalytic material for efficiently catalyzing carbon dioxide cycloaddition reaction
Technical Field
The invention relates to preparation of a nanoscale alkaline functionalized F-Mn-MOF-74 catalytic material and a cycloaddition reaction of efficiently catalyzing carbon dioxide and epoxide, wherein adenine or 2-methylimidazole is taken as an alkali source and a competitive ligand and is introduced into the synthesis of Mn-MOF-74, adenine or 2-methylimidazole is taken as an effective functional regulator, the nanoscale alkaline functionalized F-Mn-MOF-74 catalytic material is synthesized by a solvothermal method under a competitive coordination strategy, and the efficient catalytic action is realized on the cycloaddition reaction of carbon dioxide and epoxide.
Background
Carbon dioxide, as a gas which can cause greenhouse effect, causes great harm to the natural environment, but is a precious C1 resource and has the characteristics of rich yield, no toxicity, low price, nonflammability and the like. In recent years, CO has been chemically fixed2Is attracting more and more attention, and can utilize CO2The nontoxic and nonflammable raw material can be used for preparing a product with high added value, meets the requirement of green chemistry, has larger environmental effect and economic effect, and utilizes CO2The reaction with epoxide to form cyclic carbonate is successful in utilizing CO2As one of successful examples, cyclic carbonates are widely used in the production of carbonate polymers, aprotic polar solvents, intermediates for pharmaceuticals and fine chemicals, and petroleum additives, etc., for catalyzing CO2A wide variety of catalysts for the reaction with epoxides are known, such as transition metal complexes, ionic liquid catalysts, quaternary ammonium salts, metal halides, metal oxides, and the like. However, the catalyst used at present still has the problems of low catalytic activity, sensitivity to air/moisture, difficult synthesis, addition of toxic organic solvent for reaction and the like. Therefore, the development of efficient, easily available, stable, mild-condition and environmentally friendly catalysts is the core of this research.
The MOFs have significant advantages in this respect, having highly desirable properties such as high specific surface area, well-ordered porous structure and diversified means for functionalization. MOFs materials with sufficient strength and widely distributed lewis acidic and basic sites exhibit excellent catalytic activity in the cycloaddition reaction of carbon dioxide and an epoxide. And part of MOFs materials only contain single Lewis acidic or basic sites and cannot meet the requirement of efficient carbon dioxide cycloaddition catalysis, so that the research of the MOFs catalytic materials with the Lewis acidic and basic sites is very important for synthesizing cyclic carbonate by efficiently and chemically fixing carbon dioxide.
Adenine or 2-methylimidazole is introduced into the synthesis of Mn-MOF-74 as an alkali source and a competitive ligand, lone pair electrons on a nitrogen atom in adenine or 2-methylimidazole can compete with 2, 5-dihydroxyterephthalic acid for coordination, and the functionalized F-Mn-MOF-74 crystal with a nano-scale spherical structure is prepared by a solvothermal method. Adenine or 2-methylimidazole not only serves as a competitive ligand to change the crystal form of the micron-sized Mn-MOF-74, but also serves as a source of Lewis basic sites to improve the catalytic activity of the nanoscale basic functionalized F-Mn-MOF-74 catalytic material in the cycloaddition reaction of carbon dioxide and epoxide.
Disclosure of Invention
In the experiment, adenine or 2-methylimidazole is used as an alkali source and a competitive ligand and is introduced into the synthesis of Mn-MOF-74, adenine or 2-methylimidazole is used as an effective functional regulator, and the nanoscale alkaline functionalized F-Mn-MOF-74 catalytic material is synthesized by a solvothermal method under a competitive coordination strategy, so that the catalytic material has a high-efficiency catalytic effect on the cycloaddition reaction of carbon dioxide and an epoxide.
The operation steps are as follows: (1) n, N-dimethylformamide, ethanol and water are taken as solvents, a certain amount of Mn metal chloride, a certain amount of 2, 5-dihydroxyterephthalic acid and adenine or 2-methylimidazole with different molar ratios are added, and a solvent thermal synthesis method is adopted in a high-pressure reaction kettle to synthesize the alkaline functionalized F-Mn-MOF-74 catalytic material with a nano-scale spherical morphology. The nanoscale basic functionalized F-Mn-MOF-74 catalytic material has a high-efficiency catalytic effect on the cycloaddition reaction of carbon dioxide and various epoxides. (2) The method takes the nano-scale alkaline functionalized F-Mn-MOF-74 catalytic material as a catalyst for cycloaddition reaction of carbon dioxide and various epoxides, prepares various cyclic carbonates under the conditions that the temperature is 70-130 ℃, the pressure is 3-19 bar, the time is 2-14h, and the amount of the catalyst is 1-30mg, shows excellent catalytic performance, has higher selectivity and conversion rate, and can be recycled for multiple times.
Drawings
FIG. 1 is a scanning electron microscope image of micron-sized Mn-MOF-74 prepared by an embodiment of the invention.
FIG. 2 is a scanning electron microscope image of nanoscale alkaline functionalized F-Mn-MOF-74 prepared by the embodiment of the invention.
FIG. 3 is a scanning electron micrograph of nanoscale alkaline functionalized F-Mn-MOF-74 prepared by an example of the present invention after 7 times of reuse.
FIG. 4 is a comparative XRD plot of microscale Mn-MOF-74, nanoscale basic-functionalized F-Mn-MOF-74, and nanoscale basic-functionalized F-Mn-MOF-74 after 7 reuses prepared in accordance with the examples of the present invention.
FIG. 5 shows the effect of temperature of the nano-sized basic functionalized F-Mn-MOF-74 on the performance of the epoxide cycloaddition reaction catalyzed by carbon dioxide prepared by the embodiment of the invention.
FIG. 6 shows the effect of pressure on the performance of nano-sized basic functionalized F-Mn-MOF-74 catalyzed addition reaction of carbon dioxide and epoxide rings prepared by the example of the present invention.
FIG. 7 is a graph showing the effect of the reaction time of the nano-scale alkaline functionalized F-Mn-MOF-74 catalyzed addition reaction of carbon dioxide and epoxide on the performance of the F-Mn-MOF-74 prepared by the example of the present invention.
FIG. 8 is a graph showing the effect of the amount of the nano-sized basic functionalized F-Mn-MOF-74 catalytic material for catalyzing the cycloaddition of carbon dioxide and epoxide on the performance of the catalyst material prepared in the example.
FIG. 9 is a graph of the cycling performance of the nano-sized basic functionalized F-Mn-MOF-74 catalyzed addition reaction of carbon dioxide and epoxide rings prepared in the example of the present invention.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
The invention is described in further detail by means of specific examples:
example 1: reacting 2, 5-dihydroxyterephthalic acid (H)4DHBDC) (0.225 g, 1.242 mmol) and MnCl2(0.649 g, 2.497 mmol) was dissolved in 40 mL of N, N Dimethylformamide (DMF) at room temperature. The mixture solution was then transferred to a 100 mL autoclave and placed in an oven at 110 ℃ for 24 hours. After cooling to room temperature, the solid was separated by centrifugation, washed twice with DMF and methanol respectively, and finally the methanol was removed under high vacuum at 60 ℃ to give micron-sized petal-shaped Mn-MOF-74.
Example 2: adenine (8 mM) was dissolved in 30mL of N, N Dimethylformamide (DMF), and added to 40 mL of solution of 2, 5-dihydroxyterephthalic acid (H) at room temperature4DHBDC) (0.225 g, 1.242 mmol) and MnCl2(0.649 g, 2.497 mmol) in N, N Dimethylformamide (DMF). The mixture solution was then transferred to a 100 mL autoclave and placed in an oven at 110 ℃ for 24 hours. After cooling to room temperature, the solid was separated by centrifugation, washed twice with DMF and methanol respectively, and finally the methanol was removed under high vacuum at 60 ℃ to give nanoscale spherical alkaline functionalized F-Mn-MOF-74.
Example 3: 8mM of 2-methylimidazole was dissolved in 30mL of N, N Dimethylformamide (DMF), and this was added to 40 mL of solution of 2, 5-dihydroxyterephthalic acid (H) at room temperature4DHBDC) (0.225 g, 1.242 mmol) and MnCl2(0.649 g, 2.497 mmol) in N, N Dimethylformamide (DMF). The mixture solution was then transferred to a 100 mL autoclave and placed in an oven at 110 ℃ for 24 hours. After cooling to room temperature, the solid was separated by centrifugation, washed twice with DMF and methanol respectively, and finally the methanol was removed under high vacuum at 60 ℃ to give nanoscale spherical alkaline functionalized F-Mn-MOF-74.
Example 4: the cycloaddition reaction of carbon dioxide and epoxide was carried out in a 25mL stainless steel autoclave equipped with a magnetic stirrer. Firstly, putting 10mg of adenine functionalized F-Mn-MOF-74 catalyst and 20mmol of epoxide in a high-pressure reaction kettle, adding 20mg of cocatalyst (tetrabutylammonium bromide), introducing a certain amount of carbon dioxide, and reacting for 6 hours at 100 ℃ and 10 bar.
Example 5: the cycloaddition reaction of carbon dioxide and epoxide was carried out in a 25mL stainless steel autoclave equipped with a magnetic stirrer. Firstly, 10mg of 2-methylimidazole functionalized F-Mn-MOF-74 catalyst and 20mmol of epoxide are placed in a high-pressure reaction kettle, 20mg of cocatalyst (tetrabutylammonium bromide) is added, a certain amount of carbon dioxide is introduced, and the reaction is carried out for 6 hours at the temperature of 100 ℃ and the pressure of 10 bar.

Claims (4)

1. A preparation method of nanoscale alkaline functionalized F-Mn-MOF-74 is characterized by comprising the following steps: different alkali sources and competitive ligands are introduced into the synthesis of Mn-MOF-74, the alkali sources and the competitive ligands are used as effective function regulators, and a nanoscale alkaline functionalized F-Mn-MOF-74 catalytic material is synthesized by a solvothermal method under a competitive coordination strategy, and has a high-efficiency catalytic effect on the cycloaddition reaction of carbon dioxide and an epoxide.
2. The method of claim 1, wherein: adenine or dimethyl imidazole is used as an alkali source and a competitive ligand to be introduced into the synthesis of Mn-MOF-74, lone pair electrons on a nitrogen atom in adenine or dimethyl imidazole can have competitive coordination with 2,5 dihydroxy terephthalic acid, and the functionalized F-Mn-MOF-74 crystal with a nano-scale spherical structure is prepared.
3. The method of claim 1, wherein: adenine or dimethyl imidazole not only serves as a competitive ligand to change the crystal form of Mn-MOF-74, but also serves as a source of Lewis basic sites to improve the catalytic activity of the nanoscale basic functionalized F-Mn-MOF-74 catalytic material in the cycloaddition reaction of carbon dioxide and epoxide.
4. The method of claim 1, further comprising: the nanoscale alkaline functionalized F-Mn-MOF-74 catalytic material catalyzes the cycloaddition reaction of carbon dioxide and epoxide under the reaction conditions that the reaction temperature is 70-130 ℃, the reaction pressure is 3-19 bar, the reaction time is 2-14h, and the addition of the catalyst is 1-30mg, has excellent catalytic performance, and has the following optimal reaction conditions: the reaction temperature is 100 ℃, the reaction pressure is 10bar, the reaction time is 6h, and the adding amount of the catalyst is 10 mg.
CN201911348418.0A 2019-12-24 2019-12-24 Alkaline functionalized F-Mn-MOF-74 nano catalytic material for efficiently catalyzing carbon dioxide cycloaddition reaction Pending CN111068786A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201911348418.0A CN111068786A (en) 2019-12-24 2019-12-24 Alkaline functionalized F-Mn-MOF-74 nano catalytic material for efficiently catalyzing carbon dioxide cycloaddition reaction

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201911348418.0A CN111068786A (en) 2019-12-24 2019-12-24 Alkaline functionalized F-Mn-MOF-74 nano catalytic material for efficiently catalyzing carbon dioxide cycloaddition reaction

Publications (1)

Publication Number Publication Date
CN111068786A true CN111068786A (en) 2020-04-28

Family

ID=70317279

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201911348418.0A Pending CN111068786A (en) 2019-12-24 2019-12-24 Alkaline functionalized F-Mn-MOF-74 nano catalytic material for efficiently catalyzing carbon dioxide cycloaddition reaction

Country Status (1)

Country Link
CN (1) CN111068786A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115785460A (en) * 2022-09-30 2023-03-14 西安石油大学 Manganese metal organic framework material and preparation method and application thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1708534A (en) * 2002-10-25 2005-12-14 巴斯福股份公司 Process for producing polyalkylene carbonates
US20140163111A1 (en) * 2009-10-30 2014-06-12 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Porous biomolecule-containing metal-organic frameworks
CN104785209A (en) * 2015-04-09 2015-07-22 厦门大学 Metal organic framework material as well as preparation method and application thereof
CN106492754A (en) * 2016-09-30 2017-03-15 昆明理工大学 A kind of preparation method of adsorbent, method of modifying and application
JP2017160132A (en) * 2016-03-07 2017-09-14 富士フイルム株式会社 Method for producing carbonic acid ester
CN108047457A (en) * 2017-12-29 2018-05-18 南开大学 It is a kind of to be catalyzed preparation method and applications of the carbon dioxide for the metal organic frame of epoxy carbonate

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1708534A (en) * 2002-10-25 2005-12-14 巴斯福股份公司 Process for producing polyalkylene carbonates
US20140163111A1 (en) * 2009-10-30 2014-06-12 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Porous biomolecule-containing metal-organic frameworks
CN104785209A (en) * 2015-04-09 2015-07-22 厦门大学 Metal organic framework material as well as preparation method and application thereof
JP2017160132A (en) * 2016-03-07 2017-09-14 富士フイルム株式会社 Method for producing carbonic acid ester
CN106492754A (en) * 2016-09-30 2017-03-15 昆明理工大学 A kind of preparation method of adsorbent, method of modifying and application
CN108047457A (en) * 2017-12-29 2018-05-18 南开大学 It is a kind of to be catalyzed preparation method and applications of the carbon dioxide for the metal organic frame of epoxy carbonate

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
YADAGIRI RACHURI ET AL.: "Adenine-Based Zn(II)/Cd(II) Metal−Organic Frameworks as Efficient Heterogeneous Catalysts for Facile CO2 Fixation into Cyclic Carbonates: A DFT-Supported Study of the Reaction Mechanism", 《INORGANIC CHEMISTRY》 *
YUANFENG WU ET AL.: "3D-monoclinic M–BTC MOF (M=Mn, Co, Ni) as highly efficient catalysts for chemical fixation of CO2 into cyclic carbonates", 《JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115785460A (en) * 2022-09-30 2023-03-14 西安石油大学 Manganese metal organic framework material and preparation method and application thereof
CN115785460B (en) * 2022-09-30 2023-08-11 西安石油大学 Manganese metal organic frame material and preparation method and application thereof

Similar Documents

Publication Publication Date Title
Marciniak et al. Heterogeneous catalysts for cyclic carbonate synthesis from carbon dioxide and epoxides
Zanon et al. 1 Zn-doped ZIF-67 as catalyst for the CO2 fixation into cyclic carbonates
CN109776480B (en) Catalyst for synthesizing cyclic carbonate, preparation method of catalyst and preparation method of cyclic carbonate
CN110105321B (en) Method for synthesizing cyclic carbonate by catalyzing carbon dioxide through eutectic ionic liquid
CN101492528B (en) Method for synthesis of alicyclic epoxy resin with catalysis of solid supported heteropoly acid catalyst
CN111423326A (en) Method for preparing dimethyl carbonate by alkaline ionic liquid catalysis one-step method
CN111662422B (en) Metal complex covalent organic framework material and preparation method and application thereof
CN106279094B (en) A kind of method of Thiourea preparing cyclic carbonate by catalyzing with ionic liquid
Hu et al. Co (III)-Salen immobilized cellulose nanocrystals for efficient catalytic CO2 fixation into cyclic carbonates under mild conditions
CN111889141A (en) Ionic liquid functionalized bipyridine porous polymer catalyst for catalyzing cycloaddition reaction of carbon dioxide and epoxide
US5610202A (en) Catalyst system and process for the liquid-phase production of methanol from synthesis gas
CN111068786A (en) Alkaline functionalized F-Mn-MOF-74 nano catalytic material for efficiently catalyzing carbon dioxide cycloaddition reaction
Shen et al. Efficient oxidation of cumene to cumene hydroperoxide with ambient O2 catalyzed by metalloporphyrins
KR101368349B1 (en) Method of preparation of glycerol carbonate by using the metal organic frameworks as catalysts
Gao et al. Bimetallic MnZn-MOF-74 with enhanced percentage of MnIII: Efficiently catalytic activity for direct oxidative carboxylation of olefins to cyclic carbonates under mild and solvent-free condition
CN114315915B (en) Binuclear Schiff base cobalt complex and preparation method and application thereof
US9518035B2 (en) Method for preparing glycidol using glycerol and glycidol obtained thereby
CN115138386A (en) Two-dimensional hexagonal boron nitride in CO catalysis 2 Application in cycloaddition reaction with epoxide
CN101210007B (en) Method for preparing ethylene sulfite
CN114904531A (en) Supported non-noble metal monoatomic catalyst for oxidative dehydrogenation coupling reaction and preparation method and application thereof
BingLiu et al. Novel and highly efficient conversion of carbon dioxide to cyclic carbonates using benzotriazolium ionic liquid-modified periodic mesoporous organosilica as a heterogeneous and recyclable nanocatalyst
CN101210008A (en) Method for preparing ethylene sulfite
CN113563189A (en) One-step method for efficiently catalyzing CO2Method for converting dimethyl carbonate catalyst
JP2022552789A (en) Catalyst composition for the production of cyclic carbonates from CO2 and epoxides
CN107827913B (en) 1, 10-phenanthroline-containing N-heterocyclic carbene copper (I) complex and application thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20200428

WD01 Invention patent application deemed withdrawn after publication