WO2023015709A1 - Points quantiques fonctionnels exempts de métal à base de carbone, leur préparation et leur application - Google Patents

Points quantiques fonctionnels exempts de métal à base de carbone, leur préparation et leur application Download PDF

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WO2023015709A1
WO2023015709A1 PCT/CN2021/122957 CN2021122957W WO2023015709A1 WO 2023015709 A1 WO2023015709 A1 WO 2023015709A1 CN 2021122957 W CN2021122957 W CN 2021122957W WO 2023015709 A1 WO2023015709 A1 WO 2023015709A1
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carbon
based metal
free functional
functional quantum
quantum dots
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PCT/CN2021/122957
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English (en)
Chinese (zh)
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贺提为
王肖
康振辉
陈少昂
唐康健
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苏州大学
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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B32/00—Carbon; Compounds thereof
    • C01B32/15—Nano-sized carbon materials
    • 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
    • B01J21/18—Carbon
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
    • C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
    • C07C51/313—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with molecular oxygen
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/01—Crystal-structural characteristics depicted by a TEM-image
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/70—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data
    • C01P2002/72—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data by d-values or two theta-values, e.g. as X-ray diagram
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/01—Particle morphology depicted by an image
    • C01P2004/04—Particle morphology depicted by an image obtained by TEM, STEM, STM or AFM
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

Definitions

  • the invention relates to a catalyst, in particular to a carbon-based metal-free functional quantum dot and its preparation and application.
  • Carbon quantum dots are zero-dimensional carbon-based nanomaterials. Due to their unique physicochemical properties, carbon quantum dots are considered to be a promising metal-free functional material for biological, catalytic, and optoelectronic devices.
  • CN112742366A reported carbon quantum dots doped with metal ions and its preparation method and catalytic oxidation method of cycloalkane.
  • the metal-doped carbon-based material has excellent catalytic performance for catalytic oxidation of cycloalkane.
  • a series of environmental problems such as environmental pollution, cost increase, and complex synthesis methods will inevitably occur when metal doping is involved. Therefore, a non-metal-doped carbon-based nanomaterial is urgently needed to solve this problem.
  • the present invention aims to solve the above problems, and provides a carbon-based metal-free functional quantum dot and its preparation and application.
  • the novel carbon-based metal-free functional quantum dot is used as a catalyst for preparing highly selective target products from alkanes such as cyclohexane, reducing
  • the whole catalytic process has low cost, high conversion rate selectivity, no harmful substances to human body, and no environmental pollutants.
  • the preparation method of the carbon-based metal-free functional quantum dots comprises the following steps,
  • step S1 of the present invention by preparing powdered graphite, the ultraviolet light can be fully absorbed in the later stage, and the specific surface area of the graphite can be increased as much as possible to maximize the reaction.
  • step S2 the sample placed under the irradiation of the ultraviolet irradiation device is oxidized by short-wavelength ultraviolet light, and the first 15 minutes is mainly used to clean the organic matter on the surface of the powdered graphite to modify its surface and make it hydrophilic or lipophilic
  • ultraviolet radiation is mainly used for cutting and oxidizing graphite powder to form 2-5nm carbon-based metal-free functional quantum dot particles and surface oxidation to produce oxidized functional groups such as hydroxycarboxycarbonyl and the like.
  • the carbon-based metal-free functional quantum dots are completely generated by grinding and irradiating for many times.
  • the powdered graphite is obtained by grinding graphite rods, wherein physical grinding can be used for grinding.
  • the time for the first irradiation is 1-24h, preferably 12-20h; the time for each subsequent irradiation is reduced by 0.1-6h.
  • the standing time is 0.4-0.6h. Stand still in a fume hood so that the ozone generated by the irradiation cannot remain in the carbon-based metal-free functional quantum dot sample.
  • step S3 is 2-5 times.
  • the second aspect of the present invention provides the carbon-based metal-free functional quantum dots prepared by the above preparation method.
  • the carbon-based metal-free functional quantum dots only contain two elements, C and O, and do not contain any metal elements and other heteroatoms.
  • the third aspect of the present invention provides the application of the above-mentioned carbon-based metal-free functional quantum dots as catalysts in the preparation of oxidation products from C4-C10 alkanes.
  • C4-C10 alkanes include C4-C10 alkanes and C4-C10 naphthenes.
  • SS1 dissolving the carbon-based metal-free functional quantum dots in a solvent to obtain a carbon-based metal-free functional quantum dot dispersion
  • the above application includes the following steps:
  • SS2 Reacting cyclohexane, oxygen-containing gas and the carbon-based metal-free functional quantum dot dispersion liquid at 100-160° C. to prepare adipic acid.
  • the internal pressure of the reaction system of C4-C10 alkanes, oxygen-containing gas and carbon-based metal-free functional quantum dot dispersion liquid is 1-5 MPa.
  • the solvent is one or more of methanol, ethanol, propanol, butanol, acetone and butanone.
  • step SS1 the mass volume ratio of the carbon-based metal-free functional quantum dots to the solvent is 1 g/L.
  • step SS2 the volume ratio of the C4-C10 alkane to the carbon-based metal-free functional quantum dot dispersion is 1:2-5.
  • the oxygen content in the oxygen-containing gas is 0.1%-100%, preferably air (21% oxygen content).
  • the reaction time is 10-60min.
  • step SS2 after the reaction is completed, the oxidation product is obtained through recrystallization.
  • a carbon-based metal-free functional quantum dot is prepared, which has very ideal catalytic oxidation characteristics of hydrocarbons, and can be used as a catalyst for efficient oxidation of hydrocarbons.
  • the catalytic oxidation process of the material does not require other auxiliary strong acids, high-valent oxides, etc. as oxidants, and there is no equipment corrosion in the process, and no toxic and harmful gas emissions such as NOx, SOx; no metal function, less by-products; both greatly reduce production costs, It also effectively avoids the environmental pollution problems in the material production process and the catalytic process; and greatly improves the selectivity of the target product and avoids the generation of low-value by-products.
  • Figure 1 is a transmission electron microscope image of KW-1, and the inset is the corresponding high-resolution transmission electron microscope image.
  • Figure 2 is a full spectrum diagram of the X-ray photoelectron spectrum of KW-1.
  • the graphite rod is made into black powder (fine and uniform powder particles) by physical grinding and other methods and placed in a transparent quartz cuvette, so that the surface area of the stone grinding rod powder is as large as possible and the thickness is as thin as possible;
  • KW-1 only contains two non-metallic elements, carbon and oxygen, which is an innovative discovery compared to other catalysts that produce high conversion and high selectivity. And from Figure 2, it can be found that the oxygen content is 45.8%, and the oxygen content is extremely high, showing extraordinary non-toxicity and environmental harmlessness.
  • Example 1 On the basis of Example 1, the carbon-based metal-free functional quantum dots obtained in Example 1 were replaced with carbon quantum dots (prepared by electrochemical corrosion method), and the selectivity of adipic acid was 16.8% through liquid chromatography analysis, cyclohexane The conversion per pass was 0.96%.
  • Example 2 On the basis of Example 2, the carbon-based metal-free functional quantum dots obtained in Example 1 were replaced with carbon quantum dots (prepared by electrochemical corrosion method), and the selectivity of adipic acid was 12.6% through liquid chromatography analysis, cyclohexane The conversion per pass was 13.6%.
  • Example 3 On the basis of Example 3, the carbon-based metal-free functional quantum dots obtained in Example 1 were replaced with carbon quantum dots (prepared by electrochemical corrosion method), and the selectivity of adipic acid was 14.45% through liquid chromatography analysis, cyclohexane The conversion per pass was 1.25%.
  • Example 4 On the basis of Example 4, the carbon-based metal-free functional quantum dots obtained in Example 1 were replaced with carbon quantum dots (prepared by electrochemical corrosion method), and the selectivity of adipic acid was 13.69% through liquid chromatography analysis, cyclohexane The conversion per pass was 1.34%.
  • Example 5 On the basis of Example 5, the carbon-based metal-free functional quantum dots obtained in Example 1 were replaced with carbon quantum dots (prepared by electrochemical corrosion method), and the selectivity of adipic acid was 17.23% through liquid chromatography analysis, cyclohexane The conversion per pass was 2.96%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Nanotechnology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Manufacturing & Machinery (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un catalyseur. Plus précisément, la présente invention concerne un point quantique fonctionnel exempt de métal à base de carbone, son procédé de préparation et son application. La méthode de préparation comprend les étapes suivantes : S1, la préparation de graphite en poudre ; S2, l'irradiation du graphite en poudre dans des conditions UV et sa mise au repos ; S3, le broyage de la poudre obtenue en S2 ; et S4, la répétition des étapes S2 et S3 plusieurs fois pour obtenir des points quantiques fonctionnels exempts de métal à base de carbone. Les points quantiques fonctionnels exempts de métal à base de carbone préparés présentent des propriétés idéales d'oxydation catalytique d'hydrocarbures, et peuvent être utilisés comme catalyseurs pour l'oxydation efficace des hydrocarbures. Dans l'application, le processus d'oxydation catalytique ne nécessite aucun autre acide fort auxiliaire, oxyde de valence élevée, etc. comme oxydant. Aucune corrosion du dispositif n'intervient dans le processus, les émissions de NOx, SOx et autres gaz toxiques et nocifs sont inexistantes, la fonction métallique est absente et les sous-produits sont moindres. Non seulement les coûts de production sont considérablement réduits, mais les problèmes de pollution de l'environnement pendant le processus de production des matériaux et le processus catalytique sont également évités de manière efficace. De plus, la sélectivité du produit cible est grandement améliorée, et la production de sous-produits de faible valeur est évitée.
PCT/CN2021/122957 2021-08-13 2021-10-11 Points quantiques fonctionnels exempts de métal à base de carbone, leur préparation et leur application WO2023015709A1 (fr)

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CN116285974A (zh) * 2023-03-17 2023-06-23 中国科学院上海微系统与信息技术研究所 一种高量子产率和光稳定性的碳基量子点的制备方法

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