EP3922758A1 - Procédé de fabrication électrochimique d'acides alcanicarboxyliques par oxydation avec ouverture de cycle au moyen d'une électrode en mousse ni(o)oh dopée - Google Patents

Procédé de fabrication électrochimique d'acides alcanicarboxyliques par oxydation avec ouverture de cycle au moyen d'une électrode en mousse ni(o)oh dopée Download PDF

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Publication number
EP3922758A1
EP3922758A1 EP20179245.4A EP20179245A EP3922758A1 EP 3922758 A1 EP3922758 A1 EP 3922758A1 EP 20179245 A EP20179245 A EP 20179245A EP 3922758 A1 EP3922758 A1 EP 3922758A1
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EP
European Patent Office
Prior art keywords
weight
mol
carbon atoms
foam electrode
carried out
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Withdrawn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
EP20179245.4A
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German (de)
English (en)
Inventor
Frank Weinelt
Franz-Erich Baumann
Siegfried R. Waldvogel
Anna-Lisa RAUEN
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.)
Evonik Operations GmbH
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Evonik Operations GmbH
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 Evonik Operations GmbH filed Critical Evonik Operations GmbH
Priority to EP20179245.4A priority Critical patent/EP3922758A1/fr
Priority to EP21727488.5A priority patent/EP4165236B1/fr
Priority to PCT/EP2021/064057 priority patent/WO2021249775A1/fr
Priority to JP2022574171A priority patent/JP2023529827A/ja
Priority to US18/001,079 priority patent/US11976373B2/en
Priority to CN202180041010.8A priority patent/CN115917047A/zh
Publication of EP3922758A1 publication Critical patent/EP3922758A1/fr
Withdrawn legal-status Critical Current

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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
    • C25B3/23—Oxidation
    • 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
    • C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
    • C25B11/02—Electrodes; Manufacture thereof not otherwise provided for characterised by shape or form
    • C25B11/03—Electrodes; Manufacture thereof not otherwise provided for characterised by shape or form perforated or foraminous
    • C25B11/031—Porous electrodes
    • 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
    • C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
    • C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
    • C25B11/042—Electrodes formed of a single material
    • C25B11/047—Ceramics
    • 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
    • C25B3/01—Products
    • C25B3/07—Oxygen containing compounds
    • 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
    • C25B9/13—Single electrolytic cells with circulation of an electrolyte
    • C25B9/15—Flow-through cells

Definitions

  • the invention relates to a process for the electrochemical production of alkylenedicarboxylic acids by ring-opening oxidation using a doped Ni (O) OH foam electrode in an aqueous alkaline solution.
  • BV Lyalin and VA Petrosyan disclose the production of unsubstituted adipic acid and the oxidation of carbohydrates.
  • EP 2907898 A1 ( US 2015/0225861 A1 ) discloses the use of nickel foam at reaction temperatures of 80 ° C. for the oxidative ring cleavage of 3,3,5-trimethylcyclohexanol in one variant. The reaction took place in very dilute solution with low yields.
  • Schmitt et al. (Beilstein J. Org. Chem., 2015, 11, 473-480 ) disclose the cleavage of lignin into various oxo-substituted aromatics using different electrodes. The oxidation to the corresponding acids did not succeed.
  • the present invention relates to a process for the electrochemical production of alkanedicarboxylic acids by ring-opening oxidation using a doped Ni (O) OH foam electrode in an aqueous alkaline solution.
  • Another advantage is the high yield of the process according to the invention.
  • the present invention thus opens up the possibility of developing a technically relevant continuous process for the production of alkanedicarboxylic acids without the use of aggressive chemicals and nevertheless in high yields.
  • R 1 , R 2 , R 3 can be identical or different, hydrogen or an alkyl radical with 1 to 8 carbon atoms, preferably 1 to 5 carbon atoms, linear or branched, where at least one of the radicals R 1 , R 2 , R 3 is an alkyl radical.
  • radicals R 1 , R 2 , R 3 are particularly preferably hydrogen and R 2 is an alkyl radical having 1 to 4 carbon atoms.
  • the process according to the invention is preferably carried out according to scheme (IV).
  • A is a hydrocarbon with 4 to 9 carbons, all ring carbons of A in the cyclic educt of scheme (IV) bearing at least one hydrogen substituent, preferably A has at least 2 ring carbon atoms, more preferably 3 to 9 ring carbon atoms.
  • Isomers are known to the person skilled in the art; reference is made in particular to the definitions of Prof. Kazmaier of the Saarland University, e.g. B. http://www.uni-saarland.de/fak8/kazmaier/PDF_files/vorlesungen/Stereochemie%20Strassb%20V orlage.pdf referenced.
  • the Ni (O) OH foam electrode preferably has a doping with non-metallic lower-valued main group elements, preferably with elements of the 5th and / or 6th main group, more preferably selected from phosphorus, arsenic, selenium and sulfur.
  • the stated content of the doping relates to the elemental state of the doping based on the mass of the metal of the electrode.
  • the Ni (O) OH foam electrode preferably has 2 to 10% by weight, preferably 3 to 9% by weight and more preferably 4 to 9% by weight doping.
  • the Ni (O) OH foam electrode preferably has 2 to 10% by weight of phosphorus, preferably 3 to 9% by weight and more preferably 4 to 9% by weight, in this case phosphorus is regarded as an element and on the metal mass of the electrode based.
  • the determination of the content of the phosphorus doping is preferably carried out in accordance with DIN EN ISO 5427, Appendix D.1.
  • the Ni (O) OH foam electrode preferably has a thickness of several millimeters, more preferably more than 3 mm, more preferably more than 5 mm and particularly preferably equal to or thicker than 6 mm.
  • the Ni (O) OH foam electrode preferably contains at least 90% by weight, more preferably at least 95, 98, 99% by weight, more preferably at least 99.9, particularly preferably at least 99.99% by weight, as metal Nickel, based on the total metal content.
  • Ni (O) OH foam electrode can contain other metals in addition to nickel.
  • Preferred further metals are Co, Fe and Cu.
  • the content of other metals in the Ni (O) OH foam electrode is preferably equal to or less than 10% by weight, more preferably 5% by weight, more preferably 2% by weight, particularly preferably less than or equal to 1% by weight based on the total metal content.
  • the Ni (O) OH foam electrode preferably contains a maximum of 5% by weight, preferably 2% by weight, more preferably 1% by weight and particularly preferably 0.5% by weight and particularly preferably at most 0.1% by weight % Iron or iron compounds, the content data being based on the element in relation to the total metal content.
  • the Ni (O) OH foam electrode preferably contains a maximum of 1% by weight each, preferably 0.1% by weight each and more preferably a maximum of 0.01% by weight each, of V, Wo and Mo; these metals are subject to corrosion in an alkaline aqueous medium, which can have an unfavorable effect on the process according to the invention.
  • any metal inert to the reaction medium can be used as the cathode material.
  • cosolvents can be alcohols or DMSO.
  • alkaline additives are suitable as alkaline additives.
  • alkali metal hydroxides such as LiOH, NaOH, KOH, and soluble alkaline earth metal hydroxides.
  • sodium hydroxide is particularly preferably used.
  • the concentration of the alkaline additive is preferably 0.5 to 2 mol / l based on the aqueous alkaline solution, more preferably 0.8 to 1.5 mol / l and particularly preferably 1 mol / l with a possible deviation of up to 10% , preferably a deviation of up to 5% of the molarity.
  • the concentration of the starting materials according to scheme (I) is preferably 0.06 to 0.5 mol / l, more preferably 0.08 to 0.3 and particularly preferably 0.09 to 0.11 mol / l.
  • the total current which leads to the reaction according to the invention according to schemes (II) and (III) is, according to theory, 8 F. Preference is given to using 8 to 10 F, more preferably 8.5 to 9 F.
  • 6 F are required for the implementation according to scheme (IV). It is preferred to use 6 to 8 F, more preferably 6.5 to 7 F.
  • the method according to the invention is preferably carried out with a current density of 2 to 10 mA / cm 2 , more preferably 2.5 to 7.5 mA / cm 2 and particularly preferably 3.3 to 6 mA / cm 2 .
  • the area specification refers to the geometric area without taking into account the inner surface of the foam. This information on the current density relates to the largest area on one of the sides and is therefore independent of the direction of flow in the case of the flow cell.
  • the process according to the invention can be carried out discontinuously, for example in a batch electrolysis cell, or continuously in an electrolysis cell through which a flow can flow, preferably in an electrolysis cell with a continuous flow.
  • the process according to the invention is preferably carried out at temperatures of 20-70.degree. C., preferably 30-60.degree. C., more preferably 35-50.degree.
  • the method according to the invention is more preferably carried out using a doped Ni (O) OH foam electrode, the doping being selected from phosphorus, arsenic, selenium and sulfur, the concentration of alkali being 0.8 to 1.5 mol / l and the concentration of starting material according to scheme (I) is 0.08 to 0.3 mol / l.
  • the method according to the invention is more preferably carried out using a phosphorus-doped Ni (O) OH foam electrode, the concentration of alkali being 0.8 to 1.5 mol / l and the current density being 2 to 10 mA / cm 2 .
  • the process according to the invention is more preferably carried out using a phosphorus-doped Ni (O) OH foam electrode according to scheme (IV) where A is a hydrocarbon with 4 to 9 carbons, all ring carbons of A in the cyclic educt of scheme (IV) bearing at least one hydrogen substituent, preferably A has at least 2 ring carbon atoms, more preferably 3 to 9 ring carbon atoms.
  • the process according to the invention is more preferably carried out using a phosphorus-doped Ni (O) OH foam electrode in a flow cell, the concentration of alkali being 0.8 to 1.5 mol / l and the concentration of starting material according to scheme (I) Is 0.08 to 0.3 mol / l.
  • All anodes used had the dimensions length 60 mm, width 20 and thickness 6 mm. In the batch process, however, only half of the surface (length 30 mm) was immersed in order to carry out the process according to the invention.
  • the cathodes have the same surface area as the anodes, but are made from sheet metal. The thickness does not play an essential role, in particular in the flow-through process, only one surface is exposed to the reaction medium.
  • the nickel foam electrodes had a density of 0.35 to 0.44 g / cm 3 . This corresponds to a porosity of 95 to 96%.
  • the phosphorus-doped electrodes were obtained from Aqua Titan, Dortmund.
  • Ni (O) OH layer of the anodes was carried out in 280 ml of a solution of 0.1 mol / l NiSO 4 ⁇ 6H 2 O, 0.1 mol / l NaOAc ⁇ 3H 2 O, 0.005 mol / l NaOH in performed with distilled water.
  • the electrodes were completely immersed and coated with polarity changes (10 s) at 150 coulombs and 10 mA / cm 2 at room temperature. After the reaction had ended, the electrodes were rinsed and then dried.
  • the reaction cell was filled (25 ml) with water and sodium hydroxide dissolved therein (1 mol / l) and the substance to be oxidized (starting material according to scheme (I)). The concentration of starting material was 0.1 mol / l. The stirred solution was then tempered. The electro-oxidation was carried out under galvanostatic conditions.
  • the doped Ni (O) OH foam electrode produced above was used as the anode; in the experiments not according to the invention, electrodes that were basically structurally identical and not doped with phosphorus were used and stainless steel sheet electrodes were used as cathodes.
  • the solution was discharged quantitatively (with rinsing with deionized water and dichloromethane (20 ml each)) and extracted with dichloromethane (volume ratio: water to organic solvent about 2: 1).
  • the remaining aqueous phase was adjusted to pH 1 with 50% strength sulfuric acid and extracted four times with diethyl ether (volume ratio: water to organic solvent about 2 to 1).
  • the two organic phases were dried separately from one another over sodium sulfate and the solvent was then removed on a rotary evaporator.
  • the doped Ni (O) OH foam electrode prepared above was installed such that it was fully flowed through, the entrance surface was 6 mm * 20 mm in size, the direction of flow that is, in the longitudinal axis of the electrode.
  • the cathode was attached at a distance of less than one millimeter, separated by a slotted plate.
  • the chamber was flowed through from the bottom upwards in an upright position.
  • a Ritmo® 05 from Fink Chem + Tec GmbH & Co. KG was used as the pump.
  • reaction solutions were as carried out in the batch process.
  • the work-up was carried out as in the batch process.
  • Cyclooctanol-acetic acid ester was converted into octanedioic acid (DC6) in a batch process on the doped anode at 20 ° C., 5 mA / cm 2 and 8 F in 30% yield.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Ceramic Engineering (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electrodes For Compound Or Non-Metal Manufacture (AREA)
EP20179245.4A 2020-06-10 2020-06-10 Procédé de fabrication électrochimique d'acides alcanicarboxyliques par oxydation avec ouverture de cycle au moyen d'une électrode en mousse ni(o)oh dopée Withdrawn EP3922758A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP20179245.4A EP3922758A1 (fr) 2020-06-10 2020-06-10 Procédé de fabrication électrochimique d'acides alcanicarboxyliques par oxydation avec ouverture de cycle au moyen d'une électrode en mousse ni(o)oh dopée
EP21727488.5A EP4165236B1 (fr) 2020-06-10 2021-05-26 Procédé de fabrication électrochimique d'acides alcanicarboxyliques par oxydation avec ouverture de cycle au moyen d'une électrode en mousse ni(o)oh dopée
PCT/EP2021/064057 WO2021249775A1 (fr) 2020-06-10 2021-05-26 Procédé de production électrochimique d'acides alcanedicarboxyliques au moyen d'une oxydation par ouverture de cycle au moyen d'une électrode en mousse de ni(o)oh dopé
JP2022574171A JP2023529827A (ja) 2020-06-10 2021-05-26 ドープされたＮｉ（Ｏ）ＯＨ発泡電極を用いた開環酸化によるアルカンジカルボン酸の電気化学的製造方法
US18/001,079 US11976373B2 (en) 2020-06-10 2021-05-26 Method for electrochemically producing alkane dicarboxylic acids by means of a ring-opening oxidation using a doped Ni(O)OH foam electrode
CN202180041010.8A CN115917047A (zh) 2020-06-10 2021-05-26 借助于使用掺杂的Ni(O)OH泡沫电极的开环氧化来电化学生产烷烃二羧酸的方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP20179245.4A EP3922758A1 (fr) 2020-06-10 2020-06-10 Procédé de fabrication électrochimique d'acides alcanicarboxyliques par oxydation avec ouverture de cycle au moyen d'une électrode en mousse ni(o)oh dopée

Publications (1)

Publication Number Publication Date
EP3922758A1 true EP3922758A1 (fr) 2021-12-15

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EP20179245.4A Withdrawn EP3922758A1 (fr) 2020-06-10 2020-06-10 Procédé de fabrication électrochimique d'acides alcanicarboxyliques par oxydation avec ouverture de cycle au moyen d'une électrode en mousse ni(o)oh dopée
EP21727488.5A Active EP4165236B1 (fr) 2020-06-10 2021-05-26 Procédé de fabrication électrochimique d'acides alcanicarboxyliques par oxydation avec ouverture de cycle au moyen d'une électrode en mousse ni(o)oh dopée

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EP21727488.5A Active EP4165236B1 (fr) 2020-06-10 2021-05-26 Procédé de fabrication électrochimique d'acides alcanicarboxyliques par oxydation avec ouverture de cycle au moyen d'une électrode en mousse ni(o)oh dopée

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US (1) US11976373B2 (fr)
EP (2) EP3922758A1 (fr)
JP (1) JP2023529827A (fr)
CN (1) CN115917047A (fr)
WO (1) WO2021249775A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150225861A1 (en) 2014-02-12 2015-08-13 Evonik Industries Ag Process for the electrochemical production of 2,2,4-trimethyladipic acid and 2,4,4-trimethyladipic acid
CN109837555A (zh) * 2019-04-11 2019-06-04 浙江工业大学 一种镍钒磷化物催化剂电催化氧化制取2,5-呋喃二甲酸的方法
CN111229267A (zh) * 2020-01-16 2020-06-05 湖南大学 负载型磷掺杂金属羟基氧化物纳米片材料及其制备方法和应用

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DE19536056A1 (de) 1995-09-28 1997-04-03 Huels Chemische Werke Ag Flüssige Lösungen von Dicarbonsäuren
DE10207924A1 (de) 2002-02-23 2003-09-04 Clariant Gmbh Hochkonzentrierte wässrige Lösungen von Betainen oder Aminoxiden
DE102010002809A1 (de) 2010-03-12 2011-11-17 Evonik Degussa Gmbh Verfahren zur Herstellung von linearen alpha,omega-Dicarbonsäurediestern
DE102013203865A1 (de) 2013-03-07 2014-09-11 Evonik Industries Ag Elektrochemische Kupplung zweier Phenole, welche sich in ihrem Oxidationspotential unterscheiden
DE102013203866A1 (de) 2013-03-07 2014-09-11 Evonik Industries Ag Elektrochemische Kupplung eines Phenols mit einem Naphthol
EP3498759A1 (fr) 2017-12-13 2019-06-19 Evonik Degussa GmbH Procédé de fabrication de polymères à base de monomères comportant du lauryllactame
EP3741790A1 (fr) 2019-05-20 2020-11-25 Evonik Operations GmbH Polyamide à sous-structures de terpénoïdes cycliques
US20220246252A1 (en) 2019-10-01 2022-08-04 Evonik Operations Gmbh Method for producing thermoplastic compositions for mechanically and/or thermally stressed components

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Publication number Priority date Publication date Assignee Title
US20150225861A1 (en) 2014-02-12 2015-08-13 Evonik Industries Ag Process for the electrochemical production of 2,2,4-trimethyladipic acid and 2,4,4-trimethyladipic acid
EP2907898A1 (fr) 2014-02-12 2015-08-19 Evonik Degussa GmbH Procédé de fabrication électrochimique de 2,2,4 triméthyl acide adipique et 2,4,4 triméthyl acide adipique
CN109837555A (zh) * 2019-04-11 2019-06-04 浙江工业大学 一种镍钒磷化物催化剂电催化氧化制取2,5-呋喃二甲酸的方法
CN111229267A (zh) * 2020-01-16 2020-06-05 湖南大学 负载型磷掺杂金属羟基氧化物纳米片材料及其制备方法和应用

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"Russian Chemical Bulletin", vol. 53, March 2004, article "Electrosynthesis of adipic acid by undivided cell electrolysis", pages: 688 - 692
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JOHANNES KAULEN: "Anwendung zur selektiven Oxidation von Hydroxysteroiden", 1981, DISSERTATION UNIVERSITÄT MÜNSTER, article "Oxidation von Diolen und sekundären Alkoholen an der Nickelhydroxid-Elektrode"
JOHANNES KAULENHANS-JÜRGEN SCHÄFER, TETRAHEDRON, vol. 38, no. 22, 1982, pages 3299 - 3308
SCHMITT ET AL., BEILSTEIN J. ORG. CHEM., vol. 11, 2015, pages 473 - 480
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Also Published As

Publication number Publication date
EP4165236A1 (fr) 2023-04-19
JP2023529827A (ja) 2023-07-12
WO2021249775A1 (fr) 2021-12-16
CN115917047A (zh) 2023-04-04
US20230212762A1 (en) 2023-07-06
EP4165236B1 (fr) 2023-12-27
US11976373B2 (en) 2024-05-07

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