EP3294452A1 - Procédé de pyrolyse pour fabriquer des particules présentant au moins une espèce métallique - Google Patents

Procédé de pyrolyse pour fabriquer des particules présentant au moins une espèce métallique

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Publication number
EP3294452A1
EP3294452A1 EP16726491.0A EP16726491A EP3294452A1 EP 3294452 A1 EP3294452 A1 EP 3294452A1 EP 16726491 A EP16726491 A EP 16726491A EP 3294452 A1 EP3294452 A1 EP 3294452A1
Authority
EP
European Patent Office
Prior art keywords
metal
particles
metal species
compound
carbon
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
EP16726491.0A
Other languages
German (de)
English (en)
Inventor
Tobias Gärtner
Manuela KAISER
Volker Sieber
Anika SÖLDNER
Burkhard König
Melanie IWANOW
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.)
Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
Original Assignee
Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
Universitaet Regensburg
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 Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV, Universitaet Regensburg filed Critical Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
Publication of EP3294452A1 publication Critical patent/EP3294452A1/fr
Pending legal-status Critical Current

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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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/002—Mixed oxides other than spinels, e.g. perovskite
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/005—Spinels
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/48—Silver or gold
    • B01J23/52—Gold
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/74—Iron group metals
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali- or alkaline earth metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J25/00—Catalysts of the Raney type
    • B01J25/02—Raney nickel
    • 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
    • B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
    • B01J37/0027—Powdering
    • B01J37/0045—Drying a slurry, e.g. spray drying
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/0081—Preparation by melting
    • 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
    • B01J37/082—Decomposition and pyrolysis
    • B01J37/084—Decomposition of carbon-containing compounds into carbon
    • 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
    • B01J37/082—Decomposition and pyrolysis
    • B01J37/086—Decomposition of an organometallic compound, a metal complex or a metal salt of a carboxylic acid
    • 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
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
    • 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
    • C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
    • C07C5/05—Partial hydrogenation
    • 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
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/18—Carbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/44—Palladium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/16—All rings being cycloaliphatic the ring system containing five carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Definitions

  • the present invention relates to a process for the preparation of at least one
  • Hydrogenation compound a process for cross-coupling between aryl or vinyl halides and terminal alkynes, and a process for producing metal particles,
  • Metal complex particles, metal oxide particles and / or mixed metal oxide particles have long been used as catalysts in the synthesis. These supported catalysts are used both on a laboratory scale and on an industrial scale for hydrogenations, oxidation, Heck reactions, deoxygenation, hydrogenolysis and
  • Carbon or activated carbon used as support material are relatively inexpensive, have a large internal surface area and behave chemically inert both in the acidic and in the basic medium.
  • the respective transition metal can be easily recovered by complete combustion of the carbon component.
  • a fine-pored adsorption material is prepared, and then the metal is applied by impregnation to its surface.
  • wet-chemical metallization a hydrochloric acid solution of a metal chloride, an aqueous solution of a tetramine complex or a metal acetate dissolved in acetone, benzene or toluene (Gurrath M., T. Kuretzky, H. P. Boehm, L. B. Okhlopkova, A. S. Lisitsyn, V. A.
  • Likholobov, Carbon 2000, 38, 1241-1255 Palladium catalysts on activated carbon Supports: Infiuence of reduction temperature, origin of the support and pretreatments of the carbon surface; ML Toebes, JA van Dillen, KP de Jong, J. Mol. Catal. A: Chem. 2001, 173, 75-98:
  • Metal acetates and tetramine complexes limited the spectrum of usable metals. Above all, catalysts whose activity is based on the interaction of several metals are difficult to access as coal-based catalysts. Activated carbon requires a time-consuming and complex pretreatment, depending on the nature of the starting material, before being considered as
  • Carrier material can be used. Impurities such as transition metal oxides must first be dissolved out of the material and surface complexes must be removed. This
  • Preparation conditions can significantly affect catalyst activity, selectivity, and catalyst life (P. Albers, R. Burmeister, K. Seibold, G. Prescher, SF Parker, DK Ross, J. Catal. 1999, 181, 145-154: Investigations LB Okhlopkova, AS Lisitsyn, VA Likholobov, M. Gurrath, HP Boehm, Appl. Catal, A 2000, 204, 229-240: Properties of pt / c and pd / c catalysts prepared by reduction with hydrogen of adsorbed metal chloride: Infiuence of pore structure of the Support).
  • the carrier material is generally prepared first and then the corresponding metal adsorptively or covalently attached to the
  • the present invention is based on the problem, in particular to overcome the disadvantages mentioned above, and in particular to provide a method with which in particular any simple and inexpensive catalyst precursors than
  • Starting materials can be used to cost-effectively and easily carbon-supported catalytically active metal species and / or metal particles,
  • metal complex particles metal oxide particles and / or mixed metal oxide particles.
  • carbon-supported metal particles are to be provided which have a comparatively high or higher catalytic activity, such as
  • the present invention relates to a process for the preparation of particles having at least one metal species, the process comprising the following steps: a) providing at least one metal compound and at least one eutectic
  • Solvent mixture wherein the at least one eutectic solvent mixture (x) at least one hydrogen bond donor and (y) at least one
  • step B) introducing the at least one metal compound provided in step a) into the at least one eutectic solvent mixture provided in step a) at a temperature of -50 ° C. to 150 ° C., so that the at least one metal compound and the pyrolysis mixture containing at least one eutectic solvent mixture is obtained, c) pyrolyzing the pyrolysis mixture prepared in step b) at a temperature of
  • the present invention preferably relates to a process wherein the pyrolyzing according to step c) takes place under an inert gas atmosphere, so that at least one metal species-containing carbon particles are obtained.
  • the present invention preferably relates to a process wherein the pyrolyzing according to step c) takes place under carbon-oxidizing conditions, so that metal particles,
  • Metal complex particles, metal oxide particles and / or mixed metal oxide particles are obtained.
  • shing is understood to mean pyrolysis under an inert gas atmosphere or under air supply.
  • charring / charring is understood to mean pyrolysis under an inert gas atmosphere, in particular in a stream of nitrogen or argon.
  • the present invention preferably relates to a process for the preparation of carbon particles having at least one metal species, the process comprising the following steps: a) providing at least one metal compound and at least one eutectic solvent mixture, wherein the at least one eutectic solvent mixture (x) at least one hydrogen bond donor and (y) at least one
  • Contains hydrogen bond acceptor b) introducing the at least one metal compound provided in step a) into the at least one eutectic solvent mixture provided in step a) at a temperature of -50 ° C. to 150 ° C., such that a pyrolysis mixture containing the at least one metal compound and the at least one eutectic solvent mixture c) pyrolyzing the pyrolysis mixture prepared in step b) under inert gas atmosphere at a temperature of 250 ° C to 1000 ° C, so that at least one metal species-containing carbon particles are obtained; and d) obtaining the at least one metal species prepared in step c) having
  • the inventively preferred process is a novel one-step process for the preparation of at least one catalytically active metal species having, preferably doped with at least one catalytically active metal species, carbon materials
  • the carbon support and the catalytically active metal species are formed in a single step.
  • metal compounds as starting materials for the later catalytically active species, which can not be used in known from the prior art methods, in particular a corresponding solubility of these metal compounds in the impregnation media used for application to the carbon particles not or is present only too small.
  • metal oxides as starting materials for the later catalytically active species.
  • the materials according to the invention can be used preferably either as a heterogeneous catalyst in chemical reactions or as a carrier material for the production of finely powdered pure metal particles or metal complexes, metal oxides, or
  • Mixed metal oxides can be used by complete oxidation of the carbon matrix.
  • the carbon particles produced according to the invention can be used as electrode material or when pressing to electrodes.
  • the present invention preferably relates to a process for the preparation of particles having at least one metal species, in particular carbon particles, which process is a process for the preparation of a catalyst for the catalysis of a reaction.
  • the process according to the invention for the preparation of particles having at least one metal species, in particular carbon particles is accordingly preferred
  • a process for the preparation of a catalyst comprising, in particular consisting of, the at least one metal species having particles, in particular carbon particles.
  • the present invention preferably relates to a process for preparing a catalyst for the catalysis of a reaction, the process comprising the following steps: a) providing at least one metal compound and at least one eutectic
  • Solvent mixture wherein the at least one eutectic solvent mixture (x) at least one hydrogen backbonding donor and (y) at least one
  • step B) introducing the at least one metal compound provided in step a) into the at least one eutectic solvent mixture provided in step a) at a temperature of -50 ° C. to 150 ° C., such that the at least one metal compound and the at least one eutectic compound Bl) selection of a pyrolysis temperature as a function of the type, specificity and / or conversion rate of the reaction to be catalyzed by the catalyst to be obtained, c) pyrolysis of the pyrolysis mixture prepared in step b) in step bl)
  • step c) obtaining the catalyst prepared in step c), namely the at least one
  • step c) takes place under an inert gas atmosphere.
  • the particles having at least one metal species obtained in step d) are preferably at least one metal species
  • the type, specificity and / or conversion rate of the reaction to be catalysed of the catalyst obtained by the process can be controlled.
  • a catalyst can be obtained which selectively catalyzes a cross-coupling reaction but advantageously does not result in hydrogenation of the double and / or triple bonds of the reaction products and products or vice versa.
  • the process step b1) can also take place before step b) and after step a), preferably step b1) takes place before step a).
  • step b1) takes place before step c).
  • step b1) takes place before at least one of the steps a), b) or c).
  • the at least one metal compound provided for preparing a catalyst for the catalysis of a hydrogenation reaction in step a) is a palladium compound.
  • a pyrolysis temperature of from 200.degree. C. to 300.degree. C., preferably from 200.degree. C. to 250.degree. C., particularly preferably 250.degree. C. is selected for the preparation of a catalyst for the catalysis of a cross-coupling reaction in step b1).
  • a pyrolysis temperature in step b1) from 200 ° C. to 300 ° C., preferably 200 ° C. to 250 ° C., particularly preferably 250 ° C., in a cross-coupling reaction carried out with the resulting catalyst does not occur for catalyzing a hydrogenation reaction.
  • the at least one metal compound provided for preparing a catalyst for catalysis of a cross-coupling reaction in step a) is a palladium compound.
  • the term "eutectic solvent mixture” is understood as meaning a mixture which is present in liquid or viscous form at a temperature, preferably at a temperature of from -100 to + 200 ° C., and a Melting point and / or a solidification point of -100 to +200 ° C, wherein the melting point and / or the solidification point of the at least one in the mixture
  • Freezing point of the eutectic mixture is.
  • the melting point of the mixture and / or solidification point of the respective melt is well below the melting point and / or solidification point of the at least one hydrogen bonding donor and / or the at least one hydrogen bonding acceptor, if any Pure substance present.
  • the eutectic mixtures according to the invention are characterized in particular by low flammability, low water content, low vapor pressure and high
  • the eutectic solvent mixtures used according to the invention are in liquid form under the invention or preferred according to the invention
  • Carbohydrate also encompasses derivatives, ie derivatives of a carbohydrate, which are formed from the carbohydrate in one or more reaction steps.
  • Carbohydrates are preferably understood as meaning polyhydroxyaldehydes and polyhydroxyketones and relatively high molecular weight compounds which can be converted into such compounds by hydrolysis.
  • oligosaccharides is understood to mean a carbohydrate which has 3 to 20, preferably 3 to 10, monosaccharide units, preferably consisting of one another, which are each linked to one another via a glycosidic compound
  • oligosaccharide is preferably understood to mean a carbohydrate which is 3 to 20, preferably 3 to 10,
  • Monosaccharide units preferably consists thereof.
  • polysaccharides is understood as meaning carbohydrates which have at least 1, preferably at least 21, monosaccharides, preferably consisting thereof, which are each bonded to one another via a glycosidic compound
  • Polysaccharides in the context of the present invention are also understood to mean derivatives, ie derivatives of a polysaccharide, which are formed from a polysaccharide in one or more reaction steps
  • Polysaccharides according to the invention understood as meaning carbohydrates which have at least 1, preferably at least 21, monosaccharides, preferably consisting thereof, which are each linked together via a glycosidic compound.
  • carbohydrate derivative is understood to mean a derivative of a carbohydrate which consists of a carbohydrate in one or more reaction steps can be formed.
  • a carbohydrate alone is oxidized and / or reduced to produce a carbohydrate derivative.
  • the carbohydrate derivative may be prepared from a carbohydrate by a fermentative and / or catalytic process.
  • the carbohydrate derivative has a hydroxyl or carboxyl group in place of the corresponding carbohydrate rather than the aldehyde group.
  • the carbohydrate derivative preferably has at least one position, preferably at exactly one position, in place of a hydroxyl group, a hydrogen atom or an NHRio group, wherein R 1 is hydrogen, alkyl, alkenyl or alkynyl, preferably H, C, compared to the corresponding carbohydrate 1 to C8 alkyl, C 1 to C 8 alkenyl or C 1 to C 8 alkynyl.
  • the carbohydrate derivative preferably has a carboxyl group in place of the corresponding CH 2 OH group as compared to the corresponding carbohydrate.
  • the carbohydrate derivative is preferred in comparison to corresponding carbohydrate one or more, preferably exactly one, hydroxyl group which is sulfonated, esterified or etherified.
  • metal species is understood according to the invention to mean any metal species which is preferred according to the invention or according to the invention.
  • Process conditions may arise from the starting materials used, in particular from the metal compounds used.
  • the metal species may be a metal
  • (Oxidation state 0), a metal ion, a metal complex, a metal oxide, mixed metal oxide or an organometallic compound.
  • the metal species is therefore preferably present in the form of a pure metal or in the form of a compound.
  • organometallic compound refers to compounds in which a metal, preferably a metal ion, is covalently bound to a carbon radical.
  • metal complex is understood to mean mononuclear, polynuclear or polynuclear complexes, where one, two or more Metal ions, preferably as the central atom, is / are coordinated by at least one, preferably one to eight, preferably exactly one, two, three, four, five, six, seven or eight complex ligands.
  • the complex ligands are preferably selected from the group of the following compounds:
  • the present invention thus preferably provides a process for the preparation of at least one metal species-containing carbon particles, preferably with at least one
  • Metal species doped carbon particles ready, wherein at a temperature of -50 ° C to +150 ° C, preferably -20 ° C to +120 ° C, preferably 0 ° C to +100 ° C introduced the at least one metal compound in the eutectic solvent mixture, in particular suspended or dissolved, preferably dissolved, is.
  • the eutectic solvent mixture is initially introduced into a container and then the at least one metal compound is subsequently added.
  • Vibration devices suspended in the eutectic solvent mixture and / or dissolved, preferably dissolved, is.
  • the eutectic solvent mixture has the at least one hydrogen bond donor and the at least one
  • Hydrogen bond acceptor in a proportion of at least 80 wt .-%, preferably at least 85 wt .-%, preferably at least 90 wt .-%, preferably at least 95 wt .-%, preferably at least 99 wt .-%, preferably 100 wt .-% (based on the total weight of all present in the eutectic solvent mixture substances , preferably based on the total dry weight of the eutectic solvent mixture).
  • step a) in step a) exactly one single eutectic solvent mixture is provided and in step b) in this
  • Solvent mixture at least one, preferably exactly one, introduced metal compound.
  • at least two, preferably identical or different, eutectic solvent mixtures are provided in step a), in which one eutectic solvent mixture contains at least one, preferably exactly one,
  • step b) Metal compound in step b) is introduced and in another eutectic
  • Solvent mixture at least one, preferably exactly one, preferably the same or another, metal compound in step b) is introduced. Then the so
  • the at least one metal compound and the at least one, preferably exactly one, eutectic solvent mixture are provided in step a) and in step b) alone the at least one, preferably exactly one, metal compound is introduced into the at least one Step a) provided eutectic solvent mixture introduced.
  • the introduction, preferably the suspending or dissolving, preferably the dissolving, of the at least one metal compound in step b) into the eutectic solvent mixture takes place until the at least one metal compound is homogeneously distributed in the eutectic solvent mixture, preferably via one Period from 30 minutes to 5 hours, preferably from 1 hour to 2 hours.
  • the pyrolysis mixture that is to say preferably a mixture of the at least one eutectic solvent mixture and the at least one metal compound, at a temperature of 250 ° C to 1000 ° C, preferably at a temperature of 250 ° C to 600 ° C, preferably at a temperature of 300 ° C to 600 ° C, preferably at a temperature of 400 ° C to 600 ° C, in particular a temperature of 450 ° C to 600 ° C pyrolyzed under inert gas atmosphere.
  • the inert gas atmosphere has in particular a gas composition, whereby the pyrolysis of the eutectic solvent mixture takes place essentially at the temperatures used, preferably only to carbon
  • Inertgasatmospreheat only a small proportion, that is a proportion of 10 vol .-% or less, preferably 8 vol .-% or less, Favor 5 vol .-% or less, preferably 1 VoL% or less, preferably no oxidizing compounds , preferably gases, preferably oxygen, on.
  • the inert gas atmosphere preferably has at least 90%, preferably at least 95%, preferably at least 99%, preferably 100%, fraction of inert gases, preferably of noble gases, preferably argon, and / or nitrogen.
  • step c Under the conditions present in step c), the pyrolysis of the at least one hydrogen bonding donor and the at least one takes place
  • Hydrogen bond acceptor preferably to carbon-rich compounds, in particular to carbon.
  • the proportion of carbon in the product produced according to step d) depends in particular on the temperature and duration of the pyrolysis and the other
  • the carbon particles having at least one metal species produced by the method according to the invention or according to the invention have a carbon content of at least 50% by weight, preferably 60% by weight, preferably at least 60% by weight, preferably at least 70% by weight, preferably at least 80 wt .-% (based on the total dry weight of at least one metal species having
  • the carbon particles having at least one metal species thus produced preferably have on average at least 50% by weight, preferably at least 70% by weight, preferably at least 80% by weight, preferably at least 90% by weight of carbon and not more than 50% by weight. preferably at least 40 wt .-%, preferably at least 30 wt .-%, preferably at least 20 wt .-%, .-%, preferably at most 40 wt .-%, preferably at most 30 wt .-%, preferably at most 20 wt.
  • % preferably at most 10 wt .-% of the at least one metal, metal ion and / or metal oxide and 0 to 10 wt .-%, preferably at most 5 wt .-%, preferably at most 3 wt .-%, preferably at most 1 wt. %, preferably at most 0.1 wt .-% of further compounds, preferably further elements, preferably selected from the group consisting of nitrogen, halogens, oxygen, sulfur and phosphorus, based on (in each case based on the total dry weight of at least one
  • Metal species-containing carbon particles By the method according to the invention, preference is given to obtaining carbon particles which on their surface have metal particles, metal ion-containing compounds and / or metal oxide particles which are preferably catalytically active.
  • the process for the preparation of at least one metal species having carbon particles from the process steps a) to d).
  • the at least one hydrogen bond donor and / or the at least one hydrogen bond acceptor and / or the at least one metal compound is halogen-free, preferably chloride-free.
  • the present invention preferably relates to a process, wherein the at least one
  • Hydrogen bond donor is selected from carbohydrates, carbohydrate derivatives, organic acids and mixtures thereof.
  • An advantage of using a carbohydrate, a carbohydrate derivative, an organic acid or mixtures thereof is that these classes of compounds are inexpensive and can be used in large quantities for industrial purposes. They are particularly advantageous from an ecological point of view.
  • the present invention preferably relates to a process wherein the carbohydrates are selected from monosaccharides, disaccharides, oligosaccharides, polysaccharides and mixtures thereof.
  • the monosaccharide is preferably present in D or L form, preferably in D form.
  • the monosaccharide is preferably selected from hexoses, pentoses, tetroses and trioses.
  • the hexose is preferably selected from allose, altrose, glucose, mannose, gulose, idose, galactose, talose, psicose, fructose, sorbose and tagatose.
  • the pentose is preferably selected from ribose, arabinose, xylose, ribulose, xylulose and lyxose.
  • the tetrose is preferably selected from erythrose, erythrulose and threose.
  • the triose is preferably glyceraldehyde.
  • the disaccharide is formed from two, preferably above, monosaccharides, wherein the monosaccharides are covalently linked together via a glycosidic compound.
  • the disaccharide is preferably selected from cellobiose (glucose- ⁇ - (1-> 4) -glucose),
  • Gentiobiose (glucose- ⁇ - (1-> 6) -glucose), isomaltose (glucose-a- (1-> 6) -glucose), isomaltulose (glucose-a- (1-> 6) -fructose), lactose ( Galactose- ⁇ - (1-> 4) -glucose), lactulose (galactose- ⁇ - (1-> 4) -fructose), laminarabiose (glucose- ⁇ - (1-> 3) -glucose), maltose (glucose- a- (1-> 4) -glucose), maltulose (glucose-a- (1-> 4) -fructose), melibiose (galactose-1-> 6) -glucose), neohesperidosis (rhamnose- (1-> 2 ) -Glucose), neotrehalose (
  • the oligosaccharide is preferably cellulose, maltodextrin or inulin.
  • the polysaccharide is preferably inulin, starch, a glucan, a galactan or cellulose.
  • the present invention preferably relates to a process wherein the carbohydrate derivatives are selected from the group consisting of sugar alcohols, sugar acids,
  • Hydroxydicarboxylic acids hydroxytricarboxylic acids, mono-, di-, tricarboxylic acids, preferably of the carbohydrates listed herein, and mixtures thereof.
  • the carbohydrate derivative is preferably selected from tartaric acid, citric acid, malic acid, maleic acid, malonic acid, oxalic acid, chitosan, glucuronic acid, galacturonic acid, N-acetylglucosamine, glucosamine, N-acyl-galactosamine, fucose, rhamnose and quinovose.
  • the polysaccharide derivative or oligosaccharide derivative is preferably chitin, starch, preferably ⁇ -amylose, glycogen, glycosaminoglycans, preferably chondroitin sulfate, dermatan sulfate, keratan sulfate, heparin and hyaluronic acid.
  • the organic acids are preferably selected from tartaric acid, citric acid, malic acid, maleic acid, malonic acid, oxalic acid, benzoic acid, sulfonic acids, sulfinic acids, phosphoric acids and boric acids.
  • the present invention preferably relates to a process wherein the organic acids are selected from sulfonic acids, sulfinic acids, phosphoric acids, phosphonic acids and
  • Haloalkyl haloalkenyl, haloalkynyl, heteroalkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl, arylalkenyl, cycloalkylheteroalkyl, heterocycloalkylheteroalkyl,
  • Phenoxy, benzyloxy, heteroaryloxy, alkoxycarbonyl, and acyl Phenoxy, benzyloxy, heteroaryloxy, alkoxycarbonyl, and acyl.
  • each R 20 is independently selected from C 1 to C 20 alkyl, C 2 to C 20 alkenyl, C 1 to C 20 alkynyl, C 1 to C 20 haloalkyl, C 2 to C 20 haloalkenyl, C 2 to C 20 haloalkynyl, C 1 to C 20 heteroalkyl, C 3 to C 20 cycloalkyl, C 3 to C20 cycloalkenyl, C2 to C20 heterocycloalkyl, C3 to C20 heterocycloalkenyl, C4 to C20 aryl, C3 to C20 heteroaryl, C3 to C20 cycloalkylalkyl, C3 to C20 heterocycloalkylalkyl, C5 to C20 arylalkyl, C5 to C20 heteroarylalkyl, C6 to C20 arylalkenyl, C4 to C20 cycloalkylheteroalkyl, C4 to C20 heterocycloalkylhe
  • Heterocycloalkyloxy C4 to C20 aryloxy, C5 to C20 arylalkyloxy, phenoxy, benzyloxy, C2 to C20 heteroaryloxy, C1 to C20 alkoxycarbonyl, and Cl to C20 acyl.
  • R 2 o is each independently selected from C 1 to C 10 alkyl, C 2 to C 10 alkenyl, C 1 to C 10 alkynyl, C 1 to C 10 haloalkyl, C 2 to C 10 haloalkenyl, C 2 to C 10 haloalkynyl, Cl to C 10 H alioalkyl, C 3 to C 10 cycloalkyl, C3 to C10 cycloalkenyl, C2 to C10 heterocycloalkyl, C3 to C10 heterocycloalkenyl, C4 to C10 aryl, C3 to C10 heteroaryl, C3 to C10 cycloalkylalkyl, C3 to C10 heterocycloalkylalkyl, C5 to C10 arylalkyl, C4 to C10 heteroarylalkyl, C6 to C10 CIO arylalkenyl, C4 to CIO cycloalkylheteroalkyl, C4 to CIO hetero
  • R 2 o is each independently selected from C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 1 to C 6 alkynyl, C 1 to C 6 haloalkyl, C 2 to C 6 haloalkenyl, C 2 to C 6
  • the organic acid has a different chemical structure than the carbohydrate derivative.
  • the present invention preferably relates to a process, wherein the at least one
  • Hydrogen bond acceptor is selected from urea components, quaternary ammonium compounds, quaternary phosphonium compounds and mixtures thereof.
  • the present invention preferably relates to a process wherein the urea components are selected from urea components having the structural formula I, wherein R 1 , R 2 , R 3 and R 4 are each independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, heteroalkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, aryl, heteroaryl,
  • R 1 , R 2 , R 3 and R 4 are each independently selected from H, Cl to C 20 alkyl, C 2 to C 20 alkenyl, C 1 to C 20 alkynyl, C 1 to C 20 haloalkyl, C 2 to C 20
  • Cycloalkylheteroalkyl C4 to C20 Heterocycloalkylheteroalkyl, C4 to C20
  • Heteroarylheteroalkyl C5 to C20 arylheteroalkyl, Cl to C20 alkoxy, C2 to C20
  • Alkoxyalkyl C5 to C20 alkoxyaryl, C4 to C20 alkoxyheteroaryl, C2 to C20 alkenyloxy, C2 to C20 alkynyloxy, C3 to C20 cycloalkyloxy, C3 to C20 heterocycloalkyloxy, C4 to C20 aryloxy, C5 to C20 arylalkyloxy, phenoxy, benzyloxy, C2 to C20 heteroaryloxy , Cl to C20 alkoxycarbonyl, and Cl to C20 acyl.
  • R 1 , R 2 , R 3 and R 4 are each independently selected from H, Cl to CIO alkyl, C 2 to C 10 alkenyl, C 1 to C 10 alkynyl, C 1 to C 10 haloalkyl, C 2 to C 10 haloalkenyl, C 2 to C 10 haloalkynyl, Cl to CIO heteroalkyl, C3 to CIO cycloalkyl, C3 to CIO
  • Heteroarylheteroalkyl C5 to C10 arylheteroalkyl, C1 to C10 alkoxy, C2 to CIO
  • Alkoxyalkyl C5 to C10 alkoxyaryl, C4 to C10 alkoxyheteroaryl, C2 to C10 alkenyloxy, C2 to C10 alkynyloxy, C3 to C10 cycloalkyloxy, C3 to C10 heterocycloalkyloxy, C4 to C10 aryloxy, C5 to C10 arylalkyloxy, phenoxy, benzyloxy, C2 to CIO heteroaryloxy, Cl to CIO alkoxycarbonyl, and Cl to CIO acyl.
  • R 1 , R 2 , R 3 and R 4 are each independently selected from H, Cl to C6 alkyl, C 2 to C 6 alkenyl, C 1 to C 6 alkynyl, C 1 to C 6 haloalkyl, C 2 to C 6 haloalkenyl, C 2 to C 6 haloalkynyl, Cl to C6 heteroalkyl, C3 to C6 cycloalkyl, C3 to C6 cycloalkenyl, C2 to C6 heterocycloalkyl, C3 to C6 heterocycloalkenyl, C4 to C6 aryl, C3 to C6 heteroaryl, C3 to C6 cycloalkylalkyl, C3 to C6 heterocycloalkylalkyl, C5 to C7 arylalkyl, C4 to C6 heteroarylalkyl, C6 to C8 arylalkenyl, C4 to C6 cycloalkylheteroalkyl, C
  • Heterocycloalkyloxy C4 to C6 aryloxy, C5 to C7 arylalkyloxy, phenoxy, benzyloxy, C2 to C6 heteroaryloxy, C1 to C6 alkoxycarbonyl, and Cl to C6 acyl.
  • the present invention preferably relates to a process wherein the quaternary
  • Ammonium compounds and the quaternary phosphonium compounds are selected from compounds having the structural formula II,
  • R 5 , R 5 and R 7 are each independently selected from the group consisting of H, halogen, -CN, -NO 2 , -CF 3 , -OCF 3 , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl,
  • Alkynyloxy, cycloalkyloxy, heterocycloalkyloxy, aryloxy, arylalkyloxy, phenoxy, benzyloxy heteroaryloxy, alkoxycarbonyl, -SR 9 , -OR 9 and acyl, L is selected from the group consisting of H, halogen, -CN, -NO 2 , -CF 3 , -OCF 3 , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, heteroalkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl, arylalkenyl, cycloalkylheteroalkyl, heterocycloalkylhe
  • Rs is selected from the group consisting of H, hydroxyl, sulfanyl and amino, or is absent when L is H, halo, -CN, -NO 2 , -CF 3 , -OCF 3 -SR 9 or -OR 9 .
  • X is selected from the group consisting of halides, preferably fluoride or chloride, hydroxide (OH), oxoanions (A x O y z ), and anions of an organic acid, in particular an organic acid described above and
  • R 9 is selected from H, alkyl, alkenyl, alkynyl, haloalkyl, heteroalkyl, cycloalkyl,
  • Heteroarylalkyl, and acyl, optionally substituted are optionally substituted.
  • R 5 , Re, R 7 and L are each independently selected from H, halo, -CN, -NO 2 , -CF 3 , -OCF 3 , Cl to C 20 alkyl, C 2 to C 20 alkenyl, Cl to C 20 alkynyl, Cl to C20 haloalkyl, C2 to C20 haloalkenyl, C2 to C20 haloalkynyl, Cl to C20 heteroalkyl, C3 to C20 cycloalkyl, C3 to C20 cycloalkenyl, C2 to C20 heterocycloalkyl, C3 to C20
  • Heterocycloalkenyl C4 to C20 aryl, C3 to C20 heteroaryl, C3 to C20 cycloalkylalkyl, C3 to C20 heterocycloalkylalkyl, C5 to C20 arylalkyl, C5 to C20 heteroarylalkyl, C6 to C20 arylalkenyl, C4 to C20 cycloalkylheteroalkyl, C4 to C20 heterocycloalkylheteroalkyl, C4 to C20 Heteroarylheteroalkyl, C5 to C20 arylheteroalkyl, Cl to C20 alkoxy, C2 to C20
  • Alkoxyalkyl C5 to C20 alkoxyaryl, C4 to C20 alkoxyheteroaryl, C2 to C20 alkenyloxy, C2 to C20 alkynyloxy, C3 to C20 cycloalkyloxy, C3 to C20 heterocycloalkyloxy, C4 to C20 Aryloxy, C5 to C20 arylalkyloxy, phenoxy, benzyloxy, C2 to C20 heteroaryloxy, Cl to C20 alkoxycarbonyl, -SR 9 , -OR 9 and Cl to C20 acyl.
  • R 5 , Re, R 7 and L are each independently selected from H, halo, -CN, -NO 2 , -CF 3 , -OCF 3 , Cl to CIO alkyl, C 2 to C 10 alkenyl, Cl to C 10 alkynyl, Cl to CIO haloalkyl, C 2 to C 10 haloalkenyl, C 2 to C 10 haloalkynyl, C 1 to C 10 heteroalkyl, C 3 to C 10 cycloalkyl, C 3 to C 10 cycloalkenyl, C 2 to C 10 heterocycloalkyl, C 3 to C 10
  • Heterocycloalkenyl C4 to C10 aryl, C3 to C10 heteroaryl, C3 to C10 cycloalkylalkyl, C3 to C10 heterocycloalkylalkyl, C5 to C10 arylalkyl, C4 to C10 heteroarylalkyl, C6 to C10 arylalkenyl, C4 to C10 cycloalkylheteroalkyl, C4 to C10 heterocycloalkylheteroalkyl, C4 to C10 Heteroarylheteroalkyl, C5 to C10 arylheteroalkyl, C 1 to C 10 alkoxy, C 2 to C 10
  • Alkoxyalkyl C5 to C10 alkoxyaryl, C4 to C10 alkoxyheteroaryl, C2 to C10 alkenyloxy, C2 to C10 alkynyloxy, C3 to C10 cycloalkyloxy, C3 to C10 heterocycloalkyloxy, C4 to C10 aryloxy, C5 to C10 arylalkyloxy, phenoxy, benzyloxy, C2 to C10 heteroaryloxy , Cl to C10 alkoxycarbonyl, -SR 9 , -OR 9 and Cl to C10 acyl.
  • R 5 , Re, R 7 and L are each independently selected from H, halo, -CN, -NO 2 , -CF 3 , -OCF 3 , Cl to C 6 alkyl, C 2 to C 6 alkenyl, Cl to C6 alkynyl, Cl to C6 haloalkyl, C2 to C6 haloalkenyl, C2 to C6 haloalkynyl, Cl to C6 heteroalkyl, C3 to C6 cycloalkyl, C3 to C6 cycloalkenyl, C2 to C6 heterocycloalkyl, C3 to C6 heterocycloalkenyl, C4 to C6 aryl, C3 to C6 heteroaryl, C3 to C6 cycloalkylalkyl, C3 to C6
  • Heterocycloalkylalkyl C5 to C7 arylalkyl, C4 to C6 heteroarylalkyl, C6 to C8 arylalkenyl, C4 to C6 cycloalkylheteroalkyl, C4 to C6 heterocycloalkylheteroalkyl, C4 to C6
  • R 9 in structure II when present, is selected from Cl to C20 alkyl, C2 to C20 alkenyl, Cl to C20 alkynyl, Cl to C20 haloalkyl, Cl to C20 heteroalkyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C4 to C20 aryl, C3 to C20 heteroaryl, C3 to C20 cycloalkylalkyl, C3 to C20 heterocycloalkylalkyl, C5 to C20 arylalkyl, C5 to C20
  • R 9 is selected from C 1 to C 10 alkyl, C 2 to C 10 alkenyl, C 1 to C 10 alkynyl, C 1 to C 10 haloalkyl, C 1 to C 10 heteroalkyl, C 3 to C10 cycloalkyl, C2 to C10 heterocycloalkyl, C4 to C10 aryl, C3 to C10 heteroaryl, C3 to C10 cycloalkylalkyl, C3 to C10 heterocycloalkylalkyl, C5 to C10 arylalkyl, C5 to C10 heteroarylalkyl, and Cl to C10 acyl.
  • R 9 is selected from C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 1 to C 6 alkynyl, C 1 to C 6 haloalkyl, C 1 to C 6 heteroalkyl, C 3 to C 6
  • Cycloalkyl C2 to C6 heterocycloalkyl, C4 to C6 aryl, C3 to C6 heteroaryl, C3 to C6 cycloalkylalkyl, C3 to C6 heterocycloalkylalkyl, C5 to C7 arylalkyl, C5 to C7
  • Heteroarylalkyl, and Cl to C6 acyl are independently selected from the group consisting of the group consisting of the following compounds:
  • A S, P, Mn, N or Cl.
  • R21 R22 and R23 are each independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, heteroalkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, aryl, heteroaryl,
  • R24 is H or OH, preferably OH, and
  • R25 is selected from H, CH 3, F, Cl, Br, I, a carbonyl group, and formula VI
  • R 26 VI wherein Z is selected from -CH 2 -, O and S and
  • R 26 is OH or alkyl groups of 1 to 3 carbon atoms, monochloroalkyl groups of 1 to 3 carbon atoms and mono-, di- or trifluoroalkyl groups of 1 to 3 carbon atoms.
  • R 2 i R 22 and R 23 are each independently selected from H, Cl to C20 alkyl, C 2 to C 20 alkenyl, C 1 to C 20 alkynyl, C 1 to C 20 haloalkyl, C 2 to C 20 haloalkenyl, C 2 to C 20 haloalkynyl, Cl to C 20 Heteroalkyl, C3 to C20 cycloalkyl, C3 to C20
  • Cycloalkylheteroalkyl C4 to C20 Heterocycloalkylheteroalkyl, C4 to C20
  • Heteroarylheteroalkyl C5 to C20 arylheteroalkyl, Cl to C20 alkoxy, C2 to C20
  • Alkoxyalkyl C5 to C20 alkoxyaryl, C4 to C20 alkoxyheteroaryl, C2 to C20 alkenyloxy, C2 to C20 alkynyloxy, C3 to C20 cycloalkyloxy, C3 to C20 heterocycloalkyloxy, C4 to C20 aryloxy, C5 to C20 arylalkyloxy, phenoxy, benzyloxy, C2 to C20 heteroaryloxy , Cl to C20 alkoxycarbonyl, and Cl to C20 acyl.
  • R 2 i R 22 and R 23 are each independently selected from H, Cl to C 10 alkyl, C 2 to C 10 alkenyl, C 1 to C 10 alkynyl, C 1 to C 10 haloalkyl, C 2 to C 10 haloalkenyl, C 2 to C C CIO haloalkynyl, Cl to CIO heteroalkyl, C3 to CIO cycloalkyl, C3 to CIO
  • Cycloalkylheteroalkyl C4 to C10 heterocycloalkylheteroalkyl, C4 to C10
  • Heteroarylheteroalkyl C5 to C10 arylheteroalkyl, C1 to C10 alkoxy, C2 to CIO
  • Alkoxyalkyl C5 to C10 alkoxyaryl, C4 to C10 alkoxyheteroaryl, C2 to C10 alkenyloxy, C2 to C10 alkynyloxy, C3 to C10 cycloalkyloxy, C3 to C10 heterocycloalkyloxy, C4 to C10 aryloxy, C5 to C10 arylalkyloxy, phenoxy, benzyloxy, C2 to C10 heteroaryloxy , C1 to C10 alkoxycarbonyl, and C1 to C10 acyl.
  • R 2 i R 22 and R 23 are each independently selected from H, Cl to C6 alkyl, C 2 to C 6 alkenyl, C 1 to C 6 alkynyl, C 1 to C 6 haloalkyl, C 2 to C 6 haloalkenyl, C 2 to C 6 haloalkynyl, Cl to C6 Heteroalkyl, C3 to C6 cycloalkyl, C3 to C6 cycloalkenyl, C2 to C6 heterocycloalkyl, C3 to C6 heterocycloalkenyl, C4 to C6 aryl, C3 to C6 heteroaryl, C3 to C6 cycloalkylalkyl, C3 to C6 heterocycloalkylalkyl, C5 to C7 arylalkyl, C4 to C6 heteroarylalkyl, C6 to C8 arylalkenyl, C4 to C6 cycloalkylheteroalkyl, C4 to
  • V wherein A is selected from O, S, and NH;
  • R31 and R32 are each independently selected from the group consisting of alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, heteroalkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl, arylalkenyl, cycloalkylheteroalkyl .
  • R31 and R32 are each independently selected from C1 to C20 alkyl, C2 to C20 alkenyl, C1 to C20 alkynyl, C1 to C20 haloalkyl, C2 to C20 haloalkenyl, C2 to C20 haloalkynyl, C1 to C20 heteroalkyl, C3 to C20 cycloalkyl, C3 to C20 cycloalkenyl, C2 to C20 heterocycloalkyl, C3 to C20 heterocycloalkenyl, C4 to C20 aryl, C3 to C20
  • Cycloalkylheteroalkyl C4 to C20 Heterocycloalkylheteroalkyl, C4 to C20
  • Heteroarylheteroalkyl C5 to C20 arylheteroalkyl, Cl to C20 alkoxy, C2 to C20
  • Alkoxyalkyl C5 to C20 alkoxyaryl, C4 to C20 alkoxyheteroaryl, C2 to C20 alkenyloxy, C2 to C20 alkynyloxy, C3 to C20 cycloalkyloxy, C3 to C20 heterocycloalkyloxy, C4 to C20 aryloxy, C5 to C20 arylalkyloxy, phenoxy, benzyloxy, C2 to C20 heteroaryloxy, Cl to C20 alkoxycarbonyl, and Cl to C20 acyl.
  • R31 and R32 are each independently selected from C1 to C10 alkyl, C2 to C10 alkenyl, C1 to C10 alkynyl, C1 to C10 haloalkyl, C2 to C10 haloalkenyl, C2 to C10 haloalkynyl, C1 to C10 heteroalkyl, C3 to C10 cycloalkyl, C3 to CIO cycloalkenyl, C2 to CIO heterocycloalkyl, C3 to CIO heterocycloalkenyl, C4 to CIO aryl, C3 to CIO
  • Cycloalkylheteroalkyl C4 to CIO Heterocycloalkylheteroalkyl, C4 to CIO
  • Heteroarylheteroalkyl C5 to C10 arylheteroalkyl, C1 to C10 alkoxy, C2 to CIO
  • Alkoxyalkyl C5 to C10 alkoxyaryl, C4 to C10 alkoxyheteroaryl, C2 to C10 alkenyloxy, C2 to C10 alkynyloxy, C3 to C10 cycloalkyloxy, C3 to C10 heterocycloalkyloxy, C4 to C10 aryloxy, C5 to C10 arylalkyloxy, phenoxy, benzyloxy, C2 to C10 heteroaryloxy , Cl to C10 alkoxycarbonyl, and Cl to C10 acyl.
  • R31 and R32 are each independently selected from C1 to C6 alkyl, C2 to C6 alkenyl, C1 to C6 alkynyl, C1 to C6 haloalkyl, C2 to C6 haloalkenyl, C2 to C6 haloalkynyl, C1 to C6 heteroalkyl, C3 to C6 cycloalkyl, C3 to C6 cycloalkenyl, C2 to C6 heterocycloalkyl, C3 to C6 heterocycloalkenyl, C4 to C6 aryl, C3 to C6 heteroaryl, C3 to C6 cycloalkylalkyl, C3 to C6 heterocycloalkylalkyl, C5 to C7 arylalkyl, C4 to C6
  • the at least one hydrogen bond acceptor is selected from the group consisting of choline nitrate, choline tetrafluoroborate, choline hydroxide, choline bitartrate, choline dihydrogen citrate, choline p-toluenesulfonate, choline bicarbonate, choline chloride,
  • Acetylthiochloroyl chloride L-carnitine, D-carnitine, betaine, sarcosine, trimethylamine-N-oxide, betaine-HCl, cetyl-betaine, cetyltrimethylammonium fluoride, cetyltrimethylammonium chloride, cetyltrimethylammonium bromide, laurylbetaine, ⁇ , ⁇ -dimethylenethanolammonium chloride, ⁇ , ⁇ -diethylethanolammonium chloride , Beta-methylchlorine chloride, Phosphochlorine chloride,
  • Chlorodifluoroacetamide chloroacetamide, dichloroacetamide, dichlorofluoroacetamide,
  • Triiodoacetamide 2-methyl-2,2-difluoroacetamide, 2-methyl-2-fluoroacetamide, 2,2-dimethyl-2-fluoroacetamide, 2-ethyl-2,2-difluoroacetamide, 2-ethyl-2-fluoroacetamide, 2, 2-diethyl-2-fluoroacetamide, 2-propyl-2,2-difluoroacetamide, 2-propyl-2-fluoroacetamide, 2,2-propyl-2-fluoroacetamide, 2-fluoropropionamide, 3-fluoropropionamide, 2,2-difluoropropionamide, 2,3-Difluoropropionamide, 3,3-difluoropropionamide, 3,3,3-trifluoropropionamide, 2-fluoro-3,3,3-trifluoropropionamide, 2-chloro-3,3,3-trifluoropropionamide, 2,2-chloro-3-propanol 3, 3, 3-trifluoropropionamide
  • Ammonium chloride ammonium dihydrogen citrate, diammonium monohydrogen citrate,
  • Ammonium monohydrogen tartrate ammonium isothiocyanate, ammonium benzoate,
  • the at least one hydrogen bond acceptor is selected from the group consisting of a choline salt and ⁇ , ⁇ '-dimethylurea, also referred to as 1,3-dimethylurea.
  • the at least one hydrogen bonding donor is selected from the group consisting of ethyl trifluoroacetate, dithiothreitol, dithioerythritol, beta-mercaptoethanol, penicillamine, acrylamide, methanol, ethanol, propanol, butanol, taurine, aconitic acid,
  • Adipic acid benzoic acid, citric acid, malonic acid, malic acid, oxalic acid, phenylacetic acid, Phenylpropionic acid, succinic acid, levulinic acid, tartaric acid, gallic acid,
  • p-toluene sulphonic acid glycine, alanine, valine, leucine, isoleucine, serine, threonine, tyrosine, cysteine, methionine, aspartic acid, asparagine, glutamic acid, glutamine, arginine, lysine, histidine, phenylalanine, tryptophan, proline, ethylene glycol, triethylene glycol, glycerol,
  • the at least one hydrogen bonding donor is selected from the group consisting of sorbitol, tartaric acid, citric acid, glucose, fructose and mannose.
  • the present invention preferably relates to a process, wherein the at least one
  • Metal compound is an organometallic compound, a metal complex, a metal salt or a metal oxide.
  • the metal salt is a metal chloride, a metal acetate, a metal carbonate or a metal hydroxide.
  • the present invention preferably relates to a process wherein the eutectic
  • Solvent mixture (x) containing the at least one hydrogen bond donor and (y) the at least one hydrogen bond acceptor in a mass ratio of 20:80 to 80:20 ((x) to (y)).
  • the eutectic solvent mixture (x) preferably contains the at least one hydrogen bond donor and (y) the at least one
  • Hydrogen bond acceptor in a mass ratio of 30:70 to 70:30, preferably 40:60 to 60:40, preferably 45:55 to 55:45 (each (x) to (y)).
  • the present invention preferably relates to a process wherein the eutectic
  • Solvent mixture (x) contains the at least one hydrogen bond donor and (y) the at least one hydrogen bond acceptor in a molar ratio of 1:10 to 10: 1 ((x) to (y)).
  • the eutectic solvent mixture (x) preferably contains the at least one hydrogen bond donor and (y) the at least one Hydrogen backbonding acceptor in a molar ratio of 1: 5 to 5: 1, preferably 1: 3 to 3: 1, preferably 1: 2 to 2: 1 (each (x) to (y)).
  • the present invention preferably relates to a process wherein the pyrolysis mixture is pyrolyzed for 1 to 24 hours.
  • the pyrolysis mixture is preferably pyrolyzed for 2 to 20 hours, preferably for 3 to 18 hours, preferably for 4 to 15 hours, preferably for 5 to 10 hours.
  • the pyrolysis is preferably carried out in step c) in an inert gas stream, preferably in a stream of nitrogen and / or argon.
  • the at least one metal of the metal species is a transition metal or
  • the at least one metal species is one
  • the at least one metal ion is a main group metal ion or a transition metal ion.
  • the at least one metal oxide is a transition metal oxide or a main group metal oxide.
  • the at least one organometallic compound is a
  • the at least one metal complex is a transition metal complex or a
  • the present invention also relates to at least one metal species-containing, preferably with at least one metal species-doped carbon particles produced by a
  • Inventive or preferred method according to the invention can preferably be used as catalyst, that is to say are preferably a catalyst.
  • the present invention preferably relates to at least one metal, metal ion and / or
  • the BET surface area is preferably determined gravimetrically, preferably in accordance with the DIN ISO 9277: 1995 standard.
  • the carbon particles preferably have an average BET surface area of from 300 to 1200 m 2 / g, preferably from 400 to 1100 m 2 / g, preferably from 400 to 1100 m 2 / g, preferably from 500 to 1000 m 2 / g, preferably from 600 to 900 m 2 / g, preferably from 700 to 800 m 2 / g.
  • the present invention preferably relates to at least one metal species-containing, preferably with at least one metal species-doped carbon particles according to the
  • the at least one metal species is homogeneous, i. evenly distributed in the carbon particles.
  • the present invention preferably relates to at least one metal species-containing, preferably with at least one metal species-doped carbon particles according to the
  • the at least one metal species in an amount of 0.1 to 35 wt% (based on the total dry weight of the carbon particles) is present.
  • the at least one metal species is in an amount of 0.1 to 30 wt%, preferably 0.5 to 25 wt%, preferably 1.0 to 20 wt%, preferably 5.0 to 15 wt%
  • the carbon particles doped with at least one metal species and having at least one metal species preferably have an average particle size of at least 10 nm, preferably at least 100 nm, preferably at least 1000 nm, preferably at most 100 ⁇ , preferably at most 10 ⁇ .
  • the metal of the metal species is selected from lithium, sodium, potassium, rubidium, cesium, francium, beryllium, magnesium, calcium, strontium, barium, radium, boron,
  • the metal of the metal species is selected from Pt, Au, Pd, Fe, Rh, Ru, Os and Ir.
  • the metal of the metal species is selected from Pt, Au, Pd, Rh, Ru, Os and Ir.
  • the metal of the metal species is Pd, Au and / or Ru.
  • the metal of the metal species is nickel.
  • the metal oxide is preferably selected from A1 2 0 3, CuO, Cr 2 0 3, ZnO, V 2 0 5, and metal oxides having a perovskite structure, preferably SrTi0. 3
  • the present invention also relates to a process for hydrogenating at least one hydrogenation compound, the process comprising the following steps: i) providing at least one hydrogenation compound and at least one metal species-containing carbon particles according to the present invention, ii) hydrogenating the at least one provided in step i) a hydrogenation compound using the at least one metal species provided in step i)
  • the activation of the at least one metal species is carried out by known from the prior art, the usual reaction conditions and lying in the expert knowledge approach.
  • the at least one hydrogenation compound preferably has at least one hydrogenatable compound
  • Quantity ratios of the at least one hydrogenation compound and at least one metal and / or metal ion-containing carbon particles used are compounds which are known to the person skilled in the art under ordinary conditions
  • containing carbon particles can be hydrogenated.
  • the present invention relates to a hydrogenation process according to the invention, wherein prior to step i) the process according to the invention or preferred according to the invention is carried out for the production of carbon particles having at least one metal species.
  • the at least one hydrogenatable double bond and / or triple bond of the at least one hydrogenation compound is hydrogenated, wherein functional groups in the at least a hydrogenation compound, in particular alcohol groups, carboxyl groups, carbonyl groups, especially under the selected reaction conditions, are not reduced.
  • the present invention also relates to a process for cross-coupling between aryl or vinyl halides and terminal alkynes, said process comprising the steps of: i) providing at least one aryl or vinyl halide, at least one
  • Carbon particles according to the present invention ii) cross-coupling between the at least one aryl or vinyl halide provided in step i) and the at least one terminal alkyne using the at least one metal species provided in step i)
  • Carbon particles preferably doped with at least one metal species
  • the present invention also relates to a process for the production of metal particles, metal complex particles, metal oxide particles and / or mixed metal oxide particles, the process comprising the following steps:
  • Carbon particles according to the present invention bb) oxidation of the carbon provided in step aa), at least one
  • Metal species-containing carbon particles so that metal particles, metal complex particles, metal oxide particles and / or mixed oxide particles are obtained, and cc) obtaining the metal particles, metal complex particles, produced in step bb),
  • Metal oxide particles and / or mixed oxide particles By the oxidation according to step bb) metal particles, metal complex particles,
  • Metal oxide particles and / or mixed metal oxide particles obtained which are characterized in particular by a very homogeneous size distribution.
  • the oxidation of the carbon preferably gives particles which are not only homogeneous
  • the oxidation of the carbon takes place at a temperature of 250 ° C to 1000 ° C, preferably at a temperature of 250 ° C to 600 ° C, preferably at a temperature of 300 ° C to 600 ° C, preferably at a temperature of 400 ° C to 600 ° C, in particular from 450 ° C to 600 ° C instead.
  • the oxidation of the carbon in step bb) preferably takes place in an atmosphere which is at least 15% by volume, preferably at least 20% by volume, preferably at least 30% by volume, preferably at least 40% by volume, preferably at most 50 Vol .-%, preferably at most 40 vol .-% oxygen.
  • the oxidation of the carbon takes place at a temperature of 250 ° C to 1000 ° C, preferably at a temperature of 250 ° C to 600 ° C, preferably at a temperature of 300 ° C to 600 ° C, preferably at a temperature of 400 ° C to 600 ° C, in particular from 450 ° C to 600
  • the present invention therefore also relates to metal particles prepared according to the invention, metal complex particles, metal oxide particles and / or mixed metal oxide particles.
  • the resulting metal particles, metal complex particles, metal oxide particles and / or metal mixed oxide particles are preferably used as catalysts, that is to say are preferably catalysts.
  • the resulting metal particles, metal complex particles, metal oxide particles and / or metal mixed oxide particles are preferably used as support material for catalysts, that is to say are preferably support material for catalysts.
  • the present invention relates to a method according to the invention for the production of metal particles, metal complex particles, metal oxide particles and / or
  • the present invention preferably also relates to a process for the preparation of
  • step bbb) introduction of the at least one metal compound provided in step aaa) into the at least one eutectic solvent mixture provided in step aaa) at a temperature of -50 ° C to 150 ° C C, so that a pyrolysis mixture containing the at least one metal compound and the at least one eutectic solvent mixture is obtained, ccc) pyrolysis of the pyrolysis mixture prepared in step bbb)
  • these particles can be prepared from a large number of different starting compounds.
  • the process according to the invention gives rise in particular
  • the present process is preferably a process for producing mixed metal oxides.
  • Metal mixed oxides prepared according to the invention can be, for example, magnesium nitride,
  • Nickel ferrite, cobalt ferrite or zinc ferrite is preferably one Process for the preparation of mixed metal oxides of two, three or more metals selected from copper, cobalt, zinc, nickel, aluminum, magnesium and iron, in particular magnesium nitride, nickel ferrite, cobalt ferrite or zinc ferrite.
  • step aaa exactly one single eutectic solvent mixture is provided and in step bbb) at least one, preferably exactly one, metal compound is introduced into this solvent mixture.
  • at least two, preferably identical or different, eutectic solvent mixtures are provided in step aaa), in which one eutectic solvent mixture at least one, preferably exactly one,
  • step bbb) Metal compound in step bbb) is introduced and in another eutectic
  • Solvent mixture at least one, preferably exactly one, preferably the same or another, metal compound in step bbb) is introduced. Subsequently, the at least one, preferably exactly one, metal compound-containing, at least two eutectic solvent mixtures prepared in this way are mixed together and thus the pyrolysis mixture to be pyrolyzed in step ccc) is obtained.
  • carbon oxidizing conditions it is meant that under these conditions the carbon is oxidised to, preferably oxygen-containing, compounds, in particular oxidized to carbon monoxide and carbon dioxide .
  • the carbon is oxidized in step ccc) in an atmosphere which at least 15% by volume, preferably at least 20% by volume, preferably at least 30% by volume, preferably at least 40% by volume, preferably at most 50% by volume, preferably at most 40% by volume of oxygen
  • the metal mixed oxide particles produced in particular magnesium nitrite MgFe 2 0 4 , cobalt ferrite CoFe 2 0 4 , nickel ferrite NiFe 2 0 4 or
  • Zinc ferrite ZnFe 2 0 4 Zinc ferrite ZnFe 2 0 4 .
  • Figure 1 shows an activity comparison of produced at different temperatures
  • Pd / CNO catalysts An activity comparison of Pd / CNO catalysts prepared in a muffle furnace at a temperature of 440 ° C using different pyrolysis times.
  • FIG. 3 shows an activity comparison of different palladium compounds
  • WD hydrogen bond donor
  • WA hydrogen bond acceptor
  • T m melting point
  • T f freezing point
  • RT room temperature
  • Citric acid and choline used to dissolve palladium (II) chloride.
  • the charring conditions also referred to as the pyrolysis condition, were measured in terms of temperature (250-600 ° C.), heating time (1-24 h) and mass fraction of PdCl 2 in the solution (2.0-7.5% by weight). varied.
  • the analysis of the resulting fine powdery black solid was carried out by means of powder diffraction and inductively coupled plasma optical emission spectrometry (ICP-OES). Thus, the modification of palladium and the palladium content after ashing could be determined.
  • a low-melting mixture of D-glucose and choline chloride (molar ratio 2: 1) was used to dissolve palladium (II) acetate.
  • the charring conditions were 450 ° C over 3-4 h in nitrogen flow.
  • the resulting fine powdery, black solid has a content of about 23 wt .-% palladium.
  • the catalytic activity was tested in the hydrogenation of 1-dodecene.
  • the palladium catalyst produced was finely mortared and hydrogenated for activation in an autoclave or activated in situ in the hydrogenation reaction. Comparative experiments were carried out with a commercially available Pd / C (10%, Sigma Aldrich).
  • the resulting carrier material consisting of carbon, nitrogen and oxygen, differs significantly from the commercial activated carbon, which consists mainly of carbon.
  • a commercial activated carbon which consists mainly of carbon.
  • Sputtering apparatus constructed.
  • a hot gas in particular nitrogen
  • a crystallizing pyrolysis starts already in the sputtering process and thereby smaller particles are obtained compared to the preparation in the round bottomed flask.
  • porous, dark brown, small particles are scraped off the surface, transferred to a crucible, finely ground and in a muffle furnace depending on the application of the hot gas
  • nickel (II) carbonate was dissolved in a melt of D-glucose and urea (mass ratio 40:60) and then in the flask and later in the muffle furnace (at up to 450 ° C ) under
  • the nickel powder (20 mg) in methanol (5 ml) was activated in a first step in an autoclave at a temperature of 80 ° C and a hydrogen pressure of 55 bar.
  • 1-dodecene (336 mg, 2 mmol) in methanol (10 ml) was hydrogenated in an autoclave at 50 ° C and 43 bar hydrogen. After 3 h, a turnover of 94% was achieved.
  • the method described can also be used for the production of gold nanoparticles.
  • gold (III) chloride is dissolved in citric acid and then added a melt of D-glucose and urea (mass ratio 40/60).
  • the resulting mixture is first ashed in the flask and later in the muffle furnace (up to 450 ° C) in a stream of nitrogen. The particles were examined by SEM.
  • Solvent mixtures namely (i) malic acid and choline chloride, (ii) maleic acid and choline chloride, and (iii) vanillin and choline chloride, each in the molar ratio of 1: 1, dissolved and then pyrolyzed in a muffle furnace at 400, 500 or 600 ° C with air.
  • the resulting mixed oxide was present as a voluminous foam after pyrolysis.
  • the pure mixed oxide cobalt ferrite CoFe 2 0 4 was prepared by the process according to the invention.
  • hematite Fe 2 O 3 and cobalt (II) oxide CoO were dissolved in eutectic solvent mixtures, namely (i) malic acid and choline chloride, (ii) maleic acid and choline chloride, and (iii) vanillin and choline chloride, each in a molar ratio of 1: 1 and then pyrolyzed in a muffle furnace at 400, 500 or 600 ° C under air supply.
  • the resulting mixed oxide cobalt ferrite CoFe 2 0 4 was present as a voluminous foam after pyrolysis.
  • the pure mixed oxide nickel ferrite NiFe 2 0 4 was prepared by the process according to the invention.
  • hematite Fe 2 O 3 and nickel (II) oxide NiO were dissolved in eutectic solvent mixtures, namely (i) malic acid and choline chloride, (ii) maleic acid and choline chloride, and (iii) vanillin and choline chloride, each in molar ratio 1: 1 and then pyrolyzed in a muffle furnace at 400, 500 or 600 ° C under air supply.
  • the resulting mixed oxide nickel ferrite NiFe 2 0 4 was present as a voluminous foam after pyrolysis.
  • the pure mixed oxide zinc ferrite ZnFe 2 0 4 was prepared by the process according to the invention. These were hematite Fe 2 0 3 and zinc oxide ZnO in eutectic
  • Solvent mixtures namely (i) malic acid and choline chloride, (ii) maleic acid and choline chloride, and (iii) vanillin and choline chloride, each in the molar ratio of 1: 1, dissolved and then pyrolyzed in a muffle furnace at 400, 500 or 600 ° C with air.
  • the resulting mixed oxide zinc ferrite ZnFe 2 0 4 was present as a voluminous foam after pyrolysis. Without prior dissolution in eutectic solvent, the solid phase reaction of hematite Fe 2 0 3 and zinc oxide ZnO takes place only at temperatures above 900 ° C. 8. Influence of temperature and duration of the pyrolysis on the activity spectrum of the catalysts according to the invention
  • the catalyst prepared at 440 ° C has the highest activity.
  • a lower or higher production temperature leads to an activity reduction.
  • lower temperatures for preparing these catalysts are not preferred if the reaction to be catalysed is the hydrogenation mentioned above. More specifically, the catalysts prepared at a temperature of 250 ° C show only 5% conversion after 60 minutes.
  • using the catalysts prepared at 380 ° C requires a much longer reaction time to achieve complete conversion.
  • the substrate turnover stagnates at 60%.
  • the two catalysts which were prepared at higher temperatures, show only slightly reduced activity compared to the catalysts prepared at 440 ° C and differ only with each other at the beginning of the hydrogenation, whereas the catalysts, which are at a temperature of 500 ° C were prepared in the starting period up to 15% higher substrate conversion.
  • the duration of the pyrolysis could be significant and was therefore investigated.
  • three different pyrolysis times (5, 15 and 60 minutes) were used. As can be seen from FIG. 2, the catalysts produced after atomization in a muffle furnace at 440 ° C. and a duration of 15 minutes show the highest activity with complete conversion of 1-dodecene after 70 minutes. A longer pyrolysis time of 60 minutes does not improve the activity of the catalyst.
  • the Pd / CNO catalyst which was prepared at 440 ° C, has the oxidation state 0 of
  • Diffraction program measurements illuminate the teachings of the present invention that the activity of the catalyst prepared at 380 ° C is significantly less than that of the catalyst made at 440 ° C.
  • the oxidation state of the Pd / CNO catalyst prepared at 380 ° C, and partly also of the catalyst prepared at 420 ° C, is +1 (Table 3).
  • the active form of the palladium (Pd °) in these cases is not formed during the pyrolysis, whereby a slower conversion of the hydrogenation reaction to This is due to the fact that in these cases the formation of Pd ° in situ must first be effected by hydrogen.
  • the increase in the activity of the Pd / CNO catalysts according to the invention by the preparation at temperatures up to 440 ° C can also be demonstrated by BET analysis.
  • the catalyst prepared at 250 ° C shows only a surface area of 6.58 ⁇ 0.65 m 2 / g, whereas the Pd / CNO catalyst prepared at 250 ° C has almost six times the surface area of 38.89 ⁇ 1.18 m 2 / g (Table 3).
  • Table 4 shows a comparison of the hydrogenation reactions of verbenone 5f, (S) -czs-verbenol 5g, (1S) - (-) - a-pinene 5h and trans-stilbene 5n with the two different catalysts. All substrates show a significant increase in sales. The cyclic compounds with two double bonds also show a significant increase in conversion when using the Pd / CNO catalyst, which was prepared at 470 ° C. In the case of a-phellandrene 5k, ⁇ -terpinene 51 and limonene 5m (Table 5, entries 1 1, 12 and 13) remain only negligible amounts of starting material are left over, and the fully hydrogenated products and the intermediates are hydrogenated with only one double bond.
  • Pd / CNO catalyst according to the invention used under the same reaction conditions. Only a yield of product 9 of 1% could be achieved (Table 7, entry 5). Subsequently, Pd / CNO catalysts according to the present invention prepared at 200 ° C, 250 ° C and 300 ° C were examined. For the catalyst of this invention prepared at a temperature of 250 ° C, a significant increase to 82% product yield was achieved (Table 7, entries 2, 3 and 4). The result emphasizes that the production temperature of the catalysts and the resulting support material have a great influence on whether or not a particular type of reaction can be catalyzed.

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Abstract

La présente invention concerne un procédé pour fabriquer des particules présentant au moins une espèce métallique au moyen d'un mélange eutectique de solvants, des particules de carbone présentant au moins une espèce métallique fabriquées par ce procédé, un procédé pour hydrogéner au moins un composé d'hydrogénation, un procédé de couplage croisé entre des halogénures d'aryle ou des halogénures de vinyle et des alcynes terminaux et un procédé pour fabriquer des particules métalliques, des particules de complexes métalliques, des particules d'oxydes métalliques et/ou des particules d'oxydes métalliques mixtes.
EP16726491.0A 2015-05-13 2016-05-13 Procédé de pyrolyse pour fabriquer des particules présentant au moins une espèce métallique Pending EP3294452A1 (fr)

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DE102015208883.9A DE102015208883A1 (de) 2015-05-13 2015-05-13 Neuartiges Verfahren zur Herstellung von mindestens eine Metallspezies aufweisenden Partikeln
PCT/EP2016/060874 WO2016180973A1 (fr) 2015-05-13 2016-05-13 Procédé de pyrolyse pour fabriquer des particules présentant au moins une espèce métallique

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