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  • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
  • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
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  • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
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  • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
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  • B01J35/393—Metal or metal oxide crystallite size
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  • B01J35/396—Distribution of the active metal ingredient
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  • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
  • B01J37/02—Impregnation, coating or precipitation
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  • B01J37/0217—Pretreatment of the substrate before coating
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  • B01J37/0225—Coating of metal substrates
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  • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
  • B01J37/02—Impregnation, coating or precipitation
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  • B01J37/0242—Coating followed by impregnation
• • B—PERFORMING OPERATIONS; TRANSPORTING
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  • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
  • B01J37/02—Impregnation, coating or precipitation
  • B01J37/024—Multiple impregnation or coating
  • B01J37/0244—Coatings comprising several layers
• • 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
  • B01J37/16—Reducing
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  • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
  • B01J37/16—Reducing
  • B01J37/18—Reducing with gases containing free hydrogen
• • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C67/00—Preparation of carboxylic acid esters
  • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
  • C07C67/283—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
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  • B01J2235/00—Indexing scheme associated with group B01J35/00, related to the analysis techniques used to determine the catalysts form or properties
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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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
  • B01J23/84—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 arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
  • B01J23/85—Chromium, molybdenum or tungsten
  • B01J23/88—Molybdenum
  • B01J23/887—Molybdenum containing in addition other metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
  • B01J23/8878—Chromium
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  • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
  • B01J37/02—Impregnation, coating or precipitation
  • B01J37/0215—Coating
  • B01J37/0219—Coating the coating containing organic compounds
• • 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
  • B01J37/34—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation
  • B01J37/341—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation making use of electric or magnetic fields, wave energy or particle radiation
  • B01J37/343—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation making use of electric or magnetic fields, wave energy or particle radiation of ultrasonic wave energy

Definitions

• the present invention is related to a new metal powder catalytic system (catalyst), its production and its use in hydrogenation processes.
• Powderous catalysts are well known and used in chemical reactions. Important types of such catalysts are i.e. the Lindlar catalysts.
• the Lindlar catalyst is a heterogeneous catalyst which consists of palladium deposited on a calcium carbonate carrier which is also treated with various forms of lead.
• the goal of the present invention was to find a powderous catalyst with improved properties.
• the powderous catalysts according to the present invention have a metal (or metal alloy) as carrier material, instead of a calcium carbonate carrier.
• This metal alloy is coated by a metal oxide layer on which palladium (Pd) is deposited.
• new catalyst according to the present invention is free from lead (Pb). This applies to all powderous catalytic systems, which are part of this patent application.
• the present invention relates to a powderous catalytic system (I) comprising
• a metal alloy carrier comprising
• the metal oxide layer comprises CeO2. It is obvious that all percentages always add up to 100.
• the present invention relates to a powderous catalytic system ( ⁇ ) consisting of
• the metal oxide layer comprises CeO2.
• the catalytic system is in the form of a powder.
• the catalyst is easy to recycle (and to remove) after the reaction. This can be done i.e. by filtration,
• the catalyst can be used more than once (re-usable),
• the catalyst is easy to handle.
• the catalyst is free from lead.
• the catalyst shows high selectivity and activity in hydrogenation reactions.
• the metal alloys used as a carrier are known as cobalt/chromium/molybdenum alloy. Such alloys are available commercially, i.e. from EOS GmbH Germany (EOS CobaltChrome MP1 ®), from Attenborough Dental UK (Megallium ®) and from International Nickel.
• Such alloys are usually used in the field of dentistry. Especially, they are used in the production of dental prostheses.
• the catalytic system is in the form of a powder.
• Suitable metal alloys used in the present invention are cobalt/chromium/molybdenum alloy. Such alloys are available commercially, i.e. from EOS GmbH Germany (EOS CobaltChrome MP1 ®), from Attenborough Dental UK (Megallium ®) and from International Nickel.
• Preferred metal alloys comprise
• the present invention relates to a powderous catalytic system (II) which is the powderous catalytic system (I), wherein the metal alloy carrier comprises
• the metal alloy can comprise further metals, such as i.e. Cu, Fe, Ni, Mn, Si, Ti, Al and/or Nb.
• the present invention relates to a powderous catalytic system ( ⁇ ) which is the powderous catalytic system (I), wherein the metal alloy carrier consists of
• the present invention also relates to a powderous catalytic system (III), which is a powderous catalytic system (I) or (II), wherein the alloy comprises further metals, such as i.e. Cu, Fe, Ni, Mn, Si, Ti, Al and/or Nb.
• metal alloy can comprise carbon as well.
• the present invention also relates to a powderous catalytic system (IV), which is the catalytic system (I), (II) or (III), (wherein the metal alloy comprises at least one further metal chosen from the group consisting of Cu, Fe, Ni, Mn, Si, Ti, Al and Nb.
• the present invention also relates to a powderous catalytic system (V), which is the catalytic system (I), (II), (III) or (IV) wherein the metal alloy comprises carbon.
• the metal oxide layer of the embodiment of the present invention (which comprises CeO2), which coats the metal alloy, is non-acidic (preferably basic or amphoteric). Suitable non-acidic metal oxide layers can also comprise at least one further metal oxide wherein the metal is chosen from the group consisting of Zn, Cr, Mn, Mg, Cu and Al.
• the metal alloy is preferably coated with a thin layer of metal oxide layer CeO2 (0.5 - 3.5 ⁇ thickness) and optionally at least one further metal oxide wherein the metal is chosen from the group consisting of Zn, Cr, Mn, Mg, Cu and Al.
• the present invention also relates to a powderous catalytic system (VI), which is powderous catalytic system (I), ( ), (II), ( ⁇ ), (III), (IV) or (V), wherein the metal alloy is coated with a thin layer of CeO2 and optionally at least one further metal (Cr, Mn, Mg, Cu and/or Al) oxide.
• the present invention also relates to a powderous catalytic system (VI'), which is powderous catalytic system (VI), wherein the layer of metal oxide has a thickness of 0.5 - 3.5 ⁇ .
• the coating of the metal alloy is done by commonly known processes, such as i.e. dip-coating.
• the catalytic system (catalyst) of the present invention comprises between 0.1 wt-% and 50 wt-%, based on the total weight of the catalyst, of CeO2, preferably between 0.1 wt-% and 30 wt-%, more preferably between 0.5 wt-% and 5 wt-% and most preferably between 0.5 wt-% and 2 wt-%.
• the present invention also relates to a powderous catalytic system (VII), which is powderous catalytic system (I), ( ⁇ ) (II), (II'), (III), (IV), (V), (VI) or (VI'), wherein the catalyst comprises between 0.1 wt-% and 50 wt-%, based on the total weight of the catalytic system, of CeO2 (preferably between 0.1 wt-% and 30 wt-%, more preferably between 0.5 wt-% and 10 wt-% and most preferably between 0.5 wt-% and 2 wt-%).
• CeO2 preferably between 0.1 wt-% and 30 wt-%, more preferably between 0.5 wt-% and 10 wt-% and most preferably between 0.5 wt-% and 2 wt-%.
• the non-acidic metal oxide layers comprises CeO2 and at least one further metal oxide wherein the metal is chosen from the group consisting of Zn, Cr, Mn, Mg, Cu and Al. ln a more preferred embodiment of the present the non-acidic metal oxide layer comprises CeO2 and AI2O3.
• non-acidic metal oxide layer comprises CeO2 and ZnO.
• the present invention also relates to a powderous catalytic system (VIII), which is powderous catalytic system (I), ( ⁇ ) (II), (II'), (III), (IV), (V), (VI), (VI') or (VII), wherein the non-acidic metal oxide layer comprises CeO2 and AI2O3. Therefore the present invention also relates to a powderous catalytic system (IX), which is powderous catalytic system I), ( ⁇ ) (II), (II'), (III), (IV), (V), (VI), (VI') or (VII), wherein the non-acidic metal oxide layer comprises CeO2 and ZnO.
• the ratio of CeO2 : AI2O3 is from 2:1 to 1 :2 (preferably 1 :1 ).
• the ratio of CeO2 : ZnO is from 2:1 to 1 :2 (preferably 1 :1 ).
• the total content of the metal oxide will not exceed 50 wt-%, based on the total weight of the catalytic system.
• the present invention also relates to a powderous catalytic system (VIM'), which is the powderous catalytic system (VIII), wherein the ratio of CeO2 : AI2O3 is from 2:1 to 1 :2 (preferably 1 :1 ).
• the present invention also relates to a powderous catalytic system (VIII"), which is the powderous catalytic system (VIII) or (VIM'), wherein the catalyst comprises between 0.1 wt-% and 50 wt-%, based on the total weight of the catalytic system, of metal oxides (preferably between 0.1 wt-% and 30 wt-%, more preferably between 0.5 wt-% and 10 wt-% and most preferably between 0.5 wt-% and 2 wt-
• the present invention also relates to a powderous catalytic system (IX'), which is the powderous catalytic system (IX), wherein the ratio of CeO2 : ZnO is from 2:1 to 1 :2 (preferably 1 :1 ).
• the present invention also relates to a powderous catalytic system (IX"), which is the powderous catalytic system (IX) or (IX'), wherein the catalyst comprises between 0.1 wt-% and 50 wt-%, based on the total weight of the catalytic system, of metal oxides (preferably between 0.1 wt-% and 30 wt-%, more preferably between 0.5 wt-% and 10 wt-% and most preferably between 0.5 wt-% and 2 wt- %).
• metal oxides preferably between 0.1 wt-% and 30 wt-%, more preferably between 0.5 wt-% and 10 wt-% and most preferably between 0.5 wt-% and 2 wt- %.
• the coated metal alloys are then impregnated by Pd-nanoparticles.
• the nanoparticles are synthesized by commonly known methods, i.e. by using PdC as a precursor, which is then reduced by hydrogen.
• a process wherein metal alloys are impregnated by the Pd-nanoparticles by a process, which comprises a sonication step.
• the sonication is the act of applying sound energy to agitate particles in a sample.
• Ultrasonic frequencies >20 kHz are usually used, leading to the process also being known as ultrasonication or ultra-sonication.
• Such a process comprises usually (and preferably) the following steps:
• step (b) heating the solution of step (a) and subjecting the solution to sonication
• step (c) adding a reducing agent, preferably a solution of formate, to the Pd solution
• step (e) the suspension which is obtained in step (d) is filtrated and dried
• the Pd salt is dissolved in water (or aqueous solvent, which means that water is mixed at least one other solvent). Any commonly known and used Pd-salt can be used. Suitable salts are PdCI2 or Na2PdCI4. It can be one Pd-salt as well as a mixture of two or more Pd-salts. Furthermore, it is of an advantage to add at least one surfactant to the solution. Suitable are i.e. polyethylene glycol (PEG), polyvinylpyrrolidones (PVP) or glucosamides.
• PEG polyethylene glycol
• PVP polyvinylpyrrolidones
• glucosamides glucosamides.
• the solution of step is usually heated up to elevated temperature. Usually not to a higher temperature as the boiling point of the solvent (or solvent mixture used), Usually it is heated up to a temperature of between 30 - 80°C.
• the sonication is usually carried out at a frequency of 30 - 50 kHz.
• the duration of the sonication step is usually at least 10 minutes, preferred more than 20 (suitable and preferred range is 30 - 120 minutes).
• the maximal length of the duration of the sonication step is not critical.
• the sonication step can be carried out by using an ultrasonic bath or an immersion probe. Or even a combination of both methods is possible.
• step (b) To the solution of step (b) a reducing agent is added. Usually it is a sodium formate solution. But also, other formate salts (or mixtures of formate salts) could be used. Optionally (instead of or additionally), it is also possible to add H2-gas, L-ascorbic acid, and/or formic acid.
• step (c) To the solution of step (c) the metal oxide powder (or a mixture of metal oxide powders) are added. Usually the reaction mixture is stirred.
• step (d) is filtered and the obtained doped metal oxide powder is usually washed and dried.
• the Pd-nanoparticles which are on the non-acidic metal oxide layer, have an average particle size of between 0.5 and 20 nm, preferably of between 2 and 15 nm, more preferably of between 5 and 12 nm. (The average particle size can be measured by electron microscopy methods).
• the present invention also relates to a powderous catalytic system (X), which is powderous catalytic system (I), ( ⁇ ) (II), (II'), (III), (IV), (V), (VI), (VI'), (VII), (VIII), (IX), (X), (XI), (XI'), (XI"), (XII), ( ⁇ ') or (XII”), wherein the Pd-nanoparticles have an average particle size of between 0.5 and 20 nm (preferably of between 2 and 15 nm, more preferably of between 5 and 12 nm).
• the catalyst according to present invention comprises between 0.001 wt-% and 5 wt-%, based on the total weight of the catalyst, of the Pd- nanoparticles, preferably between 0.01 wt-% and 2 wt-% more preferably between 0.05 wt-% and 1 wt-%.
• the present invention also relates to a powderous catalytic system (XIV), which is the powderous catalytic system (I), ( ⁇ ) (II), (II'), (III), (IV), (V), (VI), (VI'), (VII), (VIII), (IX), (X), (XI), (XI'), (XII), (XII ) or (XIII), wherein the catalyst comprises between 0.001 wt-% and 5 wt-%, based on the total weight of the catalyst, of the Pd- nanoparticles (preferably between 0.01 wt-% and 2 wt-% more preferably between 0.05 wt-% and 1 wt-%).
• the catalyst comprises between 0.001 wt-% and 5 wt-%, based on the total weight of the catalyst, of the Pd- nanoparticles (preferably between 0.01 wt-% and 2 wt-% more preferably between 0.05 wt-% and 1 wt-%).
• the catalyst is usually activated before the use.
• the activation is done by using well known processes, such thermal activation under h .
• the catalyst of the present invention is used in selective catalytic hydrogenation of organic starting material, especially of organic starting material comprising a carbon-carbon triple bond, more especially of alkynol compounds.
• the present invention also relates to the use of a powderous catalytic system (catalyst) (I), ( ⁇ ') (II), ( ⁇ '), (III), (IV), (V), (VI), (VI'), (VII), (VIII), (VIII'), (VIII"), (IX), ( ⁇ ') or (IX") in selective catalytic hydrogenation of organic starting material, especially of organic starting material comprising a carbon-carbon triple bond, more especially of alkynol compounds.
• a powderous catalytic system catalyst
• III powderous catalytic system
• Ri is linear or branched C1-C35 alkyl or linear or branched C5-C35 alkenyl moiety, wherein the C chain can be substituted, and
• R2 is linear or branched Ci-C 4 alkyl, wherein the C chain can be substituted, R 3 is H or -C(CO)Ci-C alkyl,
• the present invention relates to a process (P) of reacting a compound of formula (I)
• Ri is linear or branched C1-C35 alkyl or linear or branched C5-C35 alkenyl moiety, wherein the C chain can be substituted, and
• R2 is linear or branched Ci-C 4 alkyl, wherein the C chain can be substituted, R 3 is H or -C(CO)Ci-C alkyl,
• Hydrogen is usually used in the form of H2 gas. Therefore the present invention relates to a process (P1 ), which process (P), wherein hydrogen is usually used in the form of H2 gas.
• the present invention relates to a process (P2), which process (P) or (P1 ), wherein, the following compounds
• the EOS CobaltChrome MP1 was heated at 450 °C for 3 h in air.
• Ce(NO3)3 ⁇ 6H2O (508 mmol) and 700 mL water were added to a beaker. The mixture was stirred until the salt was completely dissolved.
• the deposition of ZnO/CeO2 was performed by adding thermally treated MP1 powder (10.0 g) to 25 mL of the precursor solution. This mixture was stirred at room temperature for 15 min. Afterwards the suspension was filtered via a 0.45 m membrane filter and dried under vacuum at 40 °C for 2h followed by calcination at 450 °C for 1 h. This process was repeated until the desired number of primer layers had been deposited.
• Liquid samples (200 ⁇ _) were periodically withdrawn 5 from the reactor starting at a minimum conversion of 95% of MBY and analysed by gas-chromatography (HP 6890 series, GC-system). Selectivity is reported as amount of the desired semi-hydrogenation product (2-methyl-3-butene-2-ol (MBE)) compared to all reaction products.
• MBE 2-methyl-3-butene-2-ol
• Exp. 1 is a comparison example using an oxide layer known from the prior art.
• the new metal oxide powders show an improved activity as well as an improved selectivity.
• the catalyst according to the present invention show improved properties when used in selective hydrogenation processes.

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• 2018
  • 2018-05-01 EP EP18725411.5A patent/EP3618957B1/en active Active
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