EP2964811B1 - Couplage électrochimique d'anilines - Google Patents

Couplage électrochimique d'anilines Download PDF

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Publication number
EP2964811B1
EP2964811B1 EP14706609.6A EP14706609A EP2964811B1 EP 2964811 B1 EP2964811 B1 EP 2964811B1 EP 14706609 A EP14706609 A EP 14706609A EP 2964811 B1 EP2964811 B1 EP 2964811B1
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Prior art keywords
alkyl
aryl
aniline
heteroaryl
cycloalkyl
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German (de)
English (en)
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EP2964811A1 (fr
Inventor
Katrin Marie DYBALLA
Robert Franke
Dirk Fridag
Siegfried R. Waldvogel
Bernd Elsler
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Evonik Operations GmbH
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Evonik Degussa GmbH
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    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/20—Processes
    • C25B3/29—Coupling reactions
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B15/00—Operating or servicing cells
    • C25B15/02—Process control or regulation
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B9/00—Cells or assemblies of cells; Constructional parts of cells; Assemblies of constructional parts, e.g. electrode-diaphragm assemblies; Process-related cell features
    • C25B9/17—Cells comprising dimensionally-stable non-movable electrodes; Assemblies of constructional parts thereof
    • C25B9/19—Cells comprising dimensionally-stable non-movable electrodes; Assemblies of constructional parts thereof with diaphragms

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Automation & Control Theory (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
  • Electrodes For Compound Or Non-Metal Manufacture (AREA)

Claims (6)

  1. Procédé électrochimique pour la préparation de diaryldiamines, comprenant les étapes de procédé :
    a') introduction d'un solvant ou d'un mélange de solvants ainsi que d'un sel conducteur dans un récipient de réaction,
    b') addition d'une première aniline présentant un potentiel d'oxydation |EOx1| dans le récipient de réaction,
    c') addition d'une deuxième aniline présentant un potentiel d'oxydation |EOx2| dans le récipient de réaction,
    avec la condition : E Ox 2 > E Ox 1 et E Ox 2 − E Ox 1 = ΔE ,
    Figure imgb0019
     la deuxième aniline étant ajoutée en excès par rapport à la première aniline et le solvant ou le mélange de solvants étant choisi de manière telle que |ΔE| se situe dans la plage de 10 mV à 450 mV,
    d') introduction de deux électrodes dans la solution de réaction,
    e') application d'une tension aux électrodes,
    f') couplage de la première aniline avec la deuxième aniline en une diaryldiamine.
  2. Procédé selon la revendication 1, la deuxième aniline étant utilisée au moins en une quantité double par rapport à la première aniline.
  3. Procédé selon l'une quelconque des revendications 1 ou 2, le rapport de la première aniline à la deuxième aniline étant situé dans la plage de 1:2 à 1:4.
  4. Procédé selon l'une quelconque des revendications 1 à 3, le solvant ou le mélange de solvants étant choisi de manière telle que |ΔE| se situe dans la plage de 20 mV à 400 mV.
  5. Procédé selon l'une quelconque des revendications 1 à 4, la solution réactionnelle étant exempte d'oxydants organiques.
  6. Procédé selon l'une quelconque des revendications 1 à 5, la première aniline et la deuxième aniline étant choisies parmi : Ia, Ib, IIa, IIb, IIIa, IIIb, IVa, IVb :
    Figure imgb0020
    Figure imgb0021
    Figure imgb0022
    Figure imgb0023
     les substituants R1 à R48 étant choisis, indépendamment, dans le groupe formé par hydrogène, hydroxyle, (C1-C12)-alkyle, (C1-C12) -hétéroalkyle, (C4-C14) -aryle, (C4-C14)-aryl- (C1-C12)-alkyle, (C4-C14) -aryl-O- (C1-C12) -alkyle, (C3-C14) -hétéroaryle, (C3-C14) -hétéroaryl- (C1-C12) -alkyle, (C3-C12) -cycloalkyle, (C3-C12) -cycloalkyl- (C1-C12) -alkyle, (C3-C12)-hétérocycloalkyle, (C3-C12)-hétérocycloalkyl- (C1-C12) -alkyle, 0- (C1-C12) -alkyle, 0- (C1-C12) -hétéroalkyle, O-(C4-C14) -aryle, 0- (C4-C14) -aryl- (C1-C14) -alkyle, 0- (C3-C14)-hétéroaryle, 0- (C3-C14) -hétéroaryl- (C1-C14) -alkyle, 0- (C3-C12) -cycloalkyle, 0- (C3-C12) -cycloalkyl- (C1-C12) -alkyle, 0- (C3-C12) -hétérocycloalkyle, 0- (C3-C12)-hétérocycloalkyl- (C1-C12) -alkyle, halogène, S- (C1-C12)-alkyle, S- (C1-C12) -hétéroalkyle, S- (C4-C14) -aryle, S- (C4-C14) -aryl- (C1-C14) -alkyle, S- (C3-C14) -hétéroaryle, S- (C3-C14) -hétéroaryl- (C1-C14) -alkyle, S- (C3-C12) -cycloalkyle, S- (C3-C12) -cycloalkyl- (C1-C12) -alkyle, S- (C3-C12)-hétérocycloalkyle, (C1-C12) -acyle, (C4-C14) -aroyle, (C4-C14) -aroyl- (C1-C14) -alkyle, (C3-C14) -hétéroaroyle, (C1-C14) -dialkylphosphoryle, (C4-C14) -diarylphosphoryle, (C3-C12) -alkylsulfonyle, (C3-C12) -cycloalkylsulfonyle, (C4-C12)-arylsulfonyle, (C1-C12) -alkyl- (C4-C12) -arylsulfonyle, (C3-C12) -hétéroarylsulfonyle, (C=O)O-(C1-C12) -alkyle, (C=O)O-(C1-C12) -hétéroalkyle, (C=O)O- (C4-C14) -aryle, hétéroalkyle représentant un radical aliphatique non ramifié ou ramifié, qui contient un à quatre hétéroatomes, choisis dans le groupe constitué par N, 0, S et N substitué ;
    hétéroaryle représentant un radical aryle, dans lequel un à quatre atomes de carbone sont remplacés par des hétéroatomes choisis dans le groupe constitué par N, 0, S et N substitué ;
    le radical hétéroaryle pouvant également faire partie d'une structure cyclique condensée plus grande ; hétérocycloalkyle représentant des hydrocarbures cycliques saturés, qui contiennent un à quatre hétéroatomes choisis dans le groupe constitué par N, 0, S et N substitué ;
    les N substitués mentionnés pouvant être monosubstitués, les groupes alkyle, hétéroalkyle, cycloalkyle, hétérocycloalkyle, aryle et hétéroaryle pouvant être monosubstitués ou polysubstitués par des radicaux choisis dans le groupe formé par hydrogène, (C1-C14)-alkyle, (C1-C14) -hétéroalkyle, (C4-C14) -aryle, (C4-C14) -aryl- (C1-C14)-alkyle, (C3-C14) -hétéroaryle, (C3-C14) -hétéroaryl- (C1-C14)-alkyle, (C3-C12) -cycloalkyle, (C3-C12) -cycloalkyl- (C1-C14)-alkyle, (C3-C12) -hétérocycloalkyle, (C3-C12)-hétérocycloalkyl- (C1-C14) -alkyle, CF3, halogène, (C1-C10)-halogénoalkyle, hydroxy, (C1-C14) -alcoxy, (C4-C14)-aryloxy, 0- (C1-C14) -alkyl- (C4-C14) -aryle, (C3-C14)-hétéroaryloxy, N ((C1-C14) -alkyle) 2, N ((C4-C14) -aryle) 2, N ((C1-C14) -alkyl) ((C4-C14) -aryle),
    les combinaisons suivantes étant possibles : première aniline Ia Ib IIa IIb IIIa IIIb IVa IVb deuxième aniline Ib Ia IIb IIa IIIb IIIa IVb IVa
EP14706609.6A 2013-03-07 2014-02-26 Couplage électrochimique d'anilines Not-in-force EP2964811B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102013203867.4A DE102013203867A1 (de) 2013-03-07 2013-03-07 Elektrochemische Kupplung von Anilinen
PCT/EP2014/053676 WO2014135405A1 (fr) 2013-03-07 2014-02-26 Couplage électrochimique d'anilines

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EP2964811A1 EP2964811A1 (fr) 2016-01-13
EP2964811B1 true EP2964811B1 (fr) 2017-05-10

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US (1) US10266955B2 (fr)
EP (1) EP2964811B1 (fr)
JP (1) JP6157650B2 (fr)
KR (1) KR101740846B1 (fr)
CN (1) CN105102682B (fr)
AR (1) AR095075A1 (fr)
DE (1) DE102013203867A1 (fr)
ES (1) ES2629278T3 (fr)
SG (1) SG11201507156UA (fr)
TW (1) TWI588298B (fr)
WO (1) WO2014135405A1 (fr)

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DE102013203866A1 (de) 2013-03-07 2014-09-11 Evonik Industries Ag Elektrochemische Kupplung eines Phenols mit einem Naphthol
DE102013203865A1 (de) 2013-03-07 2014-09-11 Evonik Industries Ag Elektrochemische Kupplung zweier Phenole, welche sich in ihrem Oxidationspotential unterscheiden
DE102014201756A1 (de) 2014-01-31 2015-08-06 Evonik Degussa Gmbh Reinigung chlorverschmutzter Organophosphorverbindungen
EP3029013B1 (fr) 2014-12-04 2018-06-13 Evonik Degussa GmbH Monophosphites à unités de structure 4,4,5,5-Tétraphényl-1,3,2-dioxaphospholane en tant que ligands de catalyseurs d'hydroformylation
EP3037427B1 (fr) 2014-12-04 2016-11-23 Evonik Degussa GmbH Monophosphites présentant du naphtol
EP3031817B1 (fr) 2014-12-04 2019-05-01 Evonik Degussa GmbH Terphenyl-2-oxy-phosphites en tant que ligand dans catalysateurs de la hydroformylation
EP3031814B1 (fr) 2014-12-04 2016-11-23 Evonik Degussa GmbH Monophosphites presentant du menthol
EP3029054B1 (fr) 2014-12-04 2016-11-23 Evonik Degussa GmbH Phosphoramidite présentant une unité de phényle-phényle ou une unité de phényle-naphtyle
EP3029052B1 (fr) 2014-12-04 2018-02-28 Evonik Degussa GmbH Esters monophosphites de 9-Anthrol comme ligands de catalysateurs d'hydroformylation
DE102015215995A1 (de) * 2015-08-21 2017-02-23 Evonik Degussa Gmbh Verfahren zur Herstellung von unsymmetrischen NCN-Pincerliganden aus der Gruppe der m-Terphenylverbindungen
DE102015215998A1 (de) * 2015-08-21 2017-02-23 Evonik Degussa Gmbh Verfahren zur Herstellung von OCN-Pincerliganden aus der Gruppe der m-Terphenylverbindungen
DE102015216001A1 (de) * 2015-08-21 2017-02-23 Evonik Degussa Gmbh Verfahren zur Herstellung von unsymmetrischen OCO-Pincerliganden aus der Gruppe der m-Terphenylverbindungen
EP3178828A1 (fr) 2015-12-07 2017-06-14 Evonik Degussa GmbH Heterocycliques de phosphite de seleniat et leur procedes de fabrication
EP3178827A1 (fr) 2015-12-07 2017-06-14 Evonik Degussa GmbH Heterocycliques de biphosphite et de selenium et leur procede de fabrication
WO2018031889A1 (fr) * 2016-08-12 2018-02-15 California Institute Of Technology Oxydation d'hydrocarbures par électrocatalyseurs d'oxydation d'eau dans des solvants non aqueux
US10840504B2 (en) 2017-02-23 2020-11-17 California Institute Of Technology High performance inorganic complexes for next-generation redox flow batteries
WO2020104956A1 (fr) * 2018-11-21 2020-05-28 Piramal Enterprises Limited Installation et procédés de réaction organique électrochimique
CN110760877B (zh) * 2019-11-07 2021-01-29 南京工业大学 一种利用电化学微通道反应装置连续制备2-芳基-3-卤代-苯并呋喃类化合物的方法

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CN105102682B (zh) 2017-07-04
US10266955B2 (en) 2019-04-23
CN105102682A (zh) 2015-11-25
TW201447046A (zh) 2014-12-16
JP6157650B2 (ja) 2017-07-05
AR095075A1 (es) 2015-09-16
KR101740846B1 (ko) 2017-05-26
DE102013203867A1 (de) 2014-09-11
ES2629278T3 (es) 2017-08-08
US20160010226A1 (en) 2016-01-14
TWI588298B (zh) 2017-06-21
KR20150126650A (ko) 2015-11-12
JP2016517468A (ja) 2016-06-16
SG11201507156UA (en) 2015-10-29
EP2964811A1 (fr) 2016-01-13
WO2014135405A1 (fr) 2014-09-12

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