EP1708986A1 - Procede pour la reduction catalytique d'amides - Google Patents

Procede pour la reduction catalytique d'amides

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Publication number
EP1708986A1
EP1708986A1 EP04701131A EP04701131A EP1708986A1 EP 1708986 A1 EP1708986 A1 EP 1708986A1 EP 04701131 A EP04701131 A EP 04701131A EP 04701131 A EP04701131 A EP 04701131A EP 1708986 A1 EP1708986 A1 EP 1708986A1
Authority
EP
European Patent Office
Prior art keywords
catalyst
chosen
group
catalysts
ptre
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.)
Withdrawn
Application number
EP04701131A
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German (de)
English (en)
Inventor
Alan Arthur Smith
Paulo Dani
Paul David Higginson
Alan John Pettman
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.)
Avantium International BV
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Avantium International BV
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Publication of EP1708986A1 publication Critical patent/EP1708986A1/fr
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/023—Preparation; Separation; Stabilisation; Use of additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/24—Chromium, molybdenum or tungsten
    • B01J23/28—Molybdenum
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    • B01J23/32—Manganese, technetium or rhenium
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    • B01J23/56—Platinum group metals
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    • 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
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    • B01J23/8986—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 also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with manganese, technetium or rhenium
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    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
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Definitions

  • the catalytic reduction can even be performed at pressures of 30 bar or less, even at 15 bar or less.
  • the method according to the invention can also successfully be performed at a pressure of 10 bar, preferably between 5-10 bar, more preferably between 6-10 bar.
  • the reduction is performed in a continuous flow mode.
  • such a continuous flow mode can be performed in a liquid phase, it is preferably performed in gaseous phase, i.e. wherein one or more, preferably all of the reactants are passed in gaseous phase over the catalyst at the above-mentioned reaction conditions .
  • the additive preferably comprises an acid, more preferably a Lewis acid, most preferably a boron-containing compound.
  • the term "Lewis acid” is well known in the art.
  • the substrate: additive ratio in the reaction mixture is preferably 4 or less, more preferably 2 or less, and most preferably between 0.9-1.1.
  • the reaction mixture is preferably subjected to hydrogen pressures between 1 and 17 bar, more preferably between 5 and 10 bar.
  • the reaction temperature is preferably between 90 and 140 °C, more preferably between 100 and 130°C.
  • the catalyst is chosen from the group, consisting of:
  • the catalyst is preferably supported on a carrier, as outlined above .
  • the invention relates to a method for the selection of at least one bi- or trimetallic catalyst, active in the reduction of amides into amines from a collection of bi- and/or trimetallic catalysts, comprising the steps of A) preparing the catalysts on separate carriers, B) loading the catalysts prepared in step A) in separate reactor vessels, the vessels having a parallel arrangement, C) feeding and incubating the reactor vessels with an amide and hydrogen at identical conditions regarding at least one of the quantities, chosen from reaction time, temperature and pressure, D) measuring the conversion of amides into amines in each reactor vessel, E) selecting one or more of the catalysts, based on the measured conversion in step D) .
  • the reaction conditions such as reaction time, temperature and pressure are identical for the catalysts to be tested.
  • the reactions are performed at identical conditions, so that relevant selections of active catalysts can be made.
  • the said catalyst can be further tested at reaction conditions that differ from the first selection process to identify one or more catalysts that are optimally suitable for the envisaged reaction conditions.
  • the selection method that is preferably performed in a gaseous phase in flow mode, can be extrapolated to batch mode reaction for industrial processes for the preparation of amines at suitably mild reaction conditions.
  • Figures 1 to 5 refer to the results of amide reduction in flow mode.
  • Figure 1 shows a gas chromatogram of a reduction reaction of 1-acetylpyrrolidine with the catalyst RhReCu on a carbon carrier at a temperature of 160°C and a pressure of 10 bar.
  • the metal molar ratio of the catalyst was 1:1:1.
  • Figure 2 and Figure 3 show the performance of silica and carbon supported catalysts, respectively, in the reduction of 1-acetylpyrrolidine at several different temperatures. In these examples, the metal molar ratio of the catalysts is 1:1 or 1:1:1 for bimetallic or trimetallic catalysts, respectively.
  • Figure 4 shows the amine (in this case, 1-ethylpyrrolidine) formation profile at 100°C and 130°C as a function of the catalyst composition (bi- and trimetallic catalysts from groups A and B-C) .
  • the Nanoflow Equipment The catalyst screening in flow mode was carried out in reactors, arranged in parallel, the Avantium' s Nanoflow 2b (Avantium Technologies B.V., Netherlands), designed to allow gas and liquid feeds in trickle flow mode performed for this application.
  • the equipment consists of 64 parallel reactors divided into four blocks of 16 reactors. Each reactor can be loaded with up to 200 mg of catalyst. Temperature can be varied independently on each block. The maximum temperature of the unit is 450-500°C, and the maximum pressure is 40 bar. An evaporator is placed up-stream of each reactor, so that controlled evaporation of liquid can take place.
  • FeN03 Fe (N0 3 ) 3 .9H 2 0
  • PtN03 Pt (N0 3 ) 2 (H 2 0) 2
  • RuNO Ru(NO) (N0 3 ) x . (H 2 0) y

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

Abstract

La présente invention a trait à un procédé pour la réduction catalytique d'un amide pour la préparation d'une amine à une température inférieure à 200 °C et une pression inférieure à 50 bar, le catalyseur étant choisi parmi les catalyseurs bimétalliques et trimétalliques du groupe constitué de ABC, AB, AC et BC dans lequel : A est un métal choisi parmi le groupe constitué de Co, Fe, Ir, Pt, Rh et Ru ; B est un métal choisi parmi le groupe constitué de Cr, Mo, Re et V ; C est un métal choisi parmi le groupe constitué de Cu, In et Zn. L'invention a également trait à de nouveaux catalyseurs et un procédé de sélection pour de tels catalyseurs.
EP04701131A 2004-01-09 2004-01-09 Procede pour la reduction catalytique d'amides Withdrawn EP1708986A1 (fr)

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WO2013030316A2 (fr) 2011-09-01 2013-03-07 Johannes Gutenberg-Universität Mainz Procédé de désoxygénation cathodique d'amides et d'esters
WO2015124595A1 (fr) * 2014-02-18 2015-08-27 Qid S.R.L. Procédé de réduction catalysée d'oxyanions d'halogène dans des solutions aqueuses
DE102015201496A1 (de) 2015-01-29 2016-08-04 Thyssenkrupp Ag Verwendung von bimetallischen Katalysatoren in einem Verfahren zur Hydrierung von Amiden von Carbonsäuren aus nachwachsenden Rohstoffen
JP7185214B2 (ja) * 2017-03-31 2022-12-07 国立大学法人大阪大学 アミド化合物の水素化に用いる水素添加反応用触媒およびこれを用いたアミン化合物の製造方法
US12239961B2 (en) * 2017-03-31 2025-03-04 Osaka University Hydrogenation reaction catalyst used to hydrogenate amide compound and method for producing amine compound using same
WO2020050160A1 (fr) * 2018-09-05 2020-03-12 国立大学法人大阪大学 Catalyseur d'hydrogénation utilisé pour hydrogéner un composé amide et procédé pour produire un composé aminé l'utilisant
WO2020080165A1 (fr) * 2018-10-17 2020-04-23 国立大学法人大阪大学 Composé et son procédé de production
US12187691B2 (en) 2019-02-26 2025-01-07 Osaka University Hydrogenation catalyst used in amide compound hydrogenation and method for producing amine compound using same
WO2021109114A1 (fr) * 2019-12-06 2021-06-10 Rhodia Operations Catalyseur hétérogène supporté, sa préparation et son utilisation
EP4069670A4 (fr) * 2019-12-06 2023-08-30 Rhodia Operations Procédé de conversion d'amide en amine
CN117884138A (zh) * 2022-10-08 2024-04-16 中国科学院大连化学物理研究所 一种非贵金属催化剂在酰胺加氢脱氧中的应用

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IT1024470B (it) * 1973-12-18 1978-06-20 Mitsubishi Petrochemical Co Procedimento per produrre esametilen immina
US4772750A (en) * 1985-06-14 1988-09-20 The Dow Chemical Company Method of producing amines
GB8707305D0 (en) * 1987-03-26 1987-04-29 Bp Chem Int Ltd Chemical process

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See references of WO2005066112A1 *

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