EP0012215B1 - Sel de choline et d'acide hydroxy-2-butane sulfonique et son utilisation comme sel conducteur - Google Patents

Sel de choline et d'acide hydroxy-2-butane sulfonique et son utilisation comme sel conducteur Download PDF

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Publication number
EP0012215B1
EP0012215B1 EP79104324A EP79104324A EP0012215B1 EP 0012215 B1 EP0012215 B1 EP 0012215B1 EP 79104324 A EP79104324 A EP 79104324A EP 79104324 A EP79104324 A EP 79104324A EP 0012215 B1 EP0012215 B1 EP 0012215B1
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EP
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Prior art keywords
salt
electrolysis
conducting salt
salts
acid choline
Prior art date
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Expired
Application number
EP79104324A
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German (de)
English (en)
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EP0012215A1 (fr
Inventor
Harry Dr. Dipl.-Chem. Distler
Wolfgang Habermann
Joachim Dr. Dipl.-Chem. Kranz
Rudi Dr. Dipl.-Chem. Widder
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BASF SE
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BASF SE
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Classifications

    • 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

Definitions

  • the invention relates to 2-hydroxybutanesulfonic acid choline and its use as a conductive salt in organic liquids.
  • organic liquids are used as solvents for the starting products or for the process product. especially alcohols needed.
  • compounds In order to achieve the conductivity required for electrolysis, compounds must be added to the liquids which give the liquid the required conductivity.
  • the compounds used for this purpose which are usually salts. must also be stable under the reaction conditions.
  • Quaternary aryl-alkylammonium salts, quaternary tetraalkylammonium salts and ammonium salts of primary, secondary or tertiary amines are converted in the presence of alkaline compounds to ammonium bases or to the free amines and alkali metal salts, which can interfere with the electrochemical process, e.g. by side reactions of the free amines.
  • Alkali metal or alkaline earth metal salts of arylsulfonic, aryicarboxylic acids, alkylsulfonic acids and alkylcarboxylic acids are often poorly soluble in the organic liquids used, so that adequate conductivity is not achieved.
  • Alkali and alkaline earth metal salts of carboxylic acids can also be partially broken down by decarboxylation.
  • Soluble sulfides, cyanides and rhodanides are not sufficiently stable during electrolysis because they are anodically oxidized (decomposition). Soluble chlorides such as lithium chloride etc. Corrosion problems occur and chlorination can occur at the anode in undivided cells. The chlorates and perchlorates, which are stable under the electrolysis conditions, represent a safety risk in organic media.
  • the quaternary ammonium salt of formula is ideally suited as a conductive salt for electrolysis in organic liquids.
  • the conductive salt to be used according to the invention is readily soluble in many solvents, in particular in C 1 -C 12 -alkanols, so that the solutions have high conductivity.
  • the compound (I) is also stable under the electrolysis conditions and not hygroscopic, so that even those processes can be carried out without great effort, which would interfere with water.
  • the quaternary ammonium salt of formula 1 according to the invention is excellent, for example, as the conducting salt in the process described in DE-A-2711005 for the production of metal-free phthalocyanine by electrolysis of o-phthalonitrile and in other electrochemical processes, for example in the synthesis of adiponitrile, in which Deposition of metals from organic electrolytes and the electrochemical reduction of C0 2 to oxalic acid.
  • the quaternary ammonium salt according to the invention higher current yields with simultaneously low cell voltages are obtained than with conductive salts of the prior art.
  • the compound I to be used as the conductive salt can be prepared by processes known per se. One way of producing it is to convert the carbonates of the compound with the stoichiometrically required amount of the corresponding acid.
  • the salt of formula I is isolated by concentrating the solution obtained.
  • Another way is e.g. in the reaction of the chloride or sulfate of the compound (II) with the alkali metal salts of the corresponding acid.
  • the resulting alkali metal chloride is advantageously removed.
  • the salt of the formula is obtained by concentration, crystallization and filtration or by extraction of the dry residues obtained by evaporation of the solutions with polar liquids, e.g. lower alkanols.
  • the salt is generally obtained in a very pure form and can generally be used as the conducting salt without further purification.
  • the mixture is stirred until a clear, colorless solution is obtained and the water is removed in a rotary evaporator at 80 to 100 ° C. in a water jet vacuum.
  • reaction residue is extracted three times with 100 parts of ethanol each.
  • the combined alcohol extracts are freed from the solvent in vacuo.
  • the mixture is stirred at 90 to 100 ° C for 5 hours, the pH increasing to about 9. It is cooled to 15 to 20 ° C.
  • the crystal slurry obtained is suction filtered and dried.
  • the mass yield of phthalocyanine - based on the theoretically possible yield calculated from the current throughput - is 98.7% with a content of 99.8% of phthalocyanine.
  • choline salt of p-toluenesulfonic acid is used instead of the above-mentioned conductive salt, phthalocyanine is obtained in a yield of 91% and a purity of 98.1%.
  • 2.5% phosphoric acid is poured into the graphite tube (anolyte compartment) and a mixture of 40% by weight acrylonitrile as the catholyte on the side of the silver amalgam cathode. 34% by weight of water and 26% by weight of conductive salt of the formula

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Water Treatment By Electricity Or Magnetism (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)

Claims (3)

1. Sel d'ammonium quaternaire de la formule
Figure imgb0008
2. Utilisation du sel d'ammonium quaternaire suivant la revendication 1 comme sel conducteur pour l'électrolyse dans des liquides organiques.
3. Utilisation du sel d'ammonium quaternaire suivant la revendication 1 comme sel conducteur pour l'électrolyse de l'ortho-phtalo-dinitrile dans des liquides organiques.
EP79104324A 1978-11-11 1979-11-06 Sel de choline et d'acide hydroxy-2-butane sulfonique et son utilisation comme sel conducteur Expired EP0012215B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2849065 1978-11-11
DE19782849065 DE2849065A1 (de) 1978-11-11 1978-11-11 Verwendung von quartaeren ammoniumsalzen als leitsalze

Publications (2)

Publication Number Publication Date
EP0012215A1 EP0012215A1 (fr) 1980-06-25
EP0012215B1 true EP0012215B1 (fr) 1982-06-30

Family

ID=6054472

Family Applications (1)

Application Number Title Priority Date Filing Date
EP79104324A Expired EP0012215B1 (fr) 1978-11-11 1979-11-06 Sel de choline et d'acide hydroxy-2-butane sulfonique et son utilisation comme sel conducteur

Country Status (3)

Country Link
EP (1) EP0012215B1 (fr)
JP (1) JPS5572147A (fr)
DE (2) DE2849065A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9790161B2 (en) 2010-03-26 2017-10-17 Dioxide Materials, Inc Process for the sustainable production of acrylic acid
US9957624B2 (en) 2010-03-26 2018-05-01 Dioxide Materials, Inc. Electrochemical devices comprising novel catalyst mixtures
US10173169B2 (en) 2010-03-26 2019-01-08 Dioxide Materials, Inc Devices for electrocatalytic conversion of carbon dioxide
US10774431B2 (en) 2014-10-21 2020-09-15 Dioxide Materials, Inc. Ion-conducting membranes
US10975480B2 (en) 2015-02-03 2021-04-13 Dioxide Materials, Inc. Electrocatalytic process for carbon dioxide conversion

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58180463A (ja) * 1982-04-19 1983-10-21 Toyama Chem Co Ltd ビスコリンジスルホナ−ト類の製造法
DE3501775A1 (de) * 1985-01-21 1986-07-24 Henkel KGaA, 4000 Düsseldorf Neue kationtenside auf der basis von quartaeren ammoniumverbindungen und ihre verwendung in reinigungsmitteln
DE3620011A1 (de) * 1986-06-13 1987-12-17 Henkel Kgaa Neue kationtenside auf der basis von quartaeren ammoniumverbindungen und ihre verwendung in reinigungsmitteln
DE3811247A1 (de) * 1988-04-02 1989-10-12 Henkel Kgaa Quartaere ammoniumverbindungen
US5053531A (en) * 1988-11-08 1991-10-01 Ppg Industries, Inc. Quaternary ammonium antistatic compounds
US4904825A (en) * 1988-11-08 1990-02-27 Ppg Industries, Inc. Quaternary ammonium antistatic compounds
US5187214A (en) * 1988-11-08 1993-02-16 Ppg Industries, Inc. Quaternary ammonium antistatic polymer compositions
ES2153622T3 (es) * 1996-06-12 2001-03-01 Akzo Nobel Nv Ester carbonico de betaina, su preparacion y utilizacion.
US9012345B2 (en) 2010-03-26 2015-04-21 Dioxide Materials, Inc. Electrocatalysts for carbon dioxide conversion
US20110237830A1 (en) 2010-03-26 2011-09-29 Dioxide Materials Inc Novel catalyst mixtures
US9815021B2 (en) 2010-03-26 2017-11-14 Dioxide Materials, Inc. Electrocatalytic process for carbon dioxide conversion
US9566574B2 (en) 2010-07-04 2017-02-14 Dioxide Materials, Inc. Catalyst mixtures
US8956990B2 (en) 2010-03-26 2015-02-17 Dioxide Materials, Inc. Catalyst mixtures
US9193593B2 (en) 2010-03-26 2015-11-24 Dioxide Materials, Inc. Hydrogenation of formic acid to formaldehyde
EP2588647A1 (fr) * 2010-07-04 2013-05-08 Dioxide Materials Inc. Nouveaux mélanges de catalyseurs
CN104822861B (zh) 2012-09-24 2017-03-08 二氧化碳材料公司 用于将二氧化碳转化为有用燃料和化学品的装置和方法
US10647652B2 (en) 2013-02-24 2020-05-12 Dioxide Materials, Inc. Process for the sustainable production of acrylic acid
DE102016217730A1 (de) * 2016-09-16 2018-03-22 Siemens Aktiengesellschaft CO2-Elektrolyseverfahren
JP6761386B2 (ja) * 2016-09-29 2020-09-23 信越化学工業株式会社 粘着剤組成物、生体電極、生体電極の製造方法、及び塩

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB967956A (en) * 1960-12-12 1964-08-26 Monsanto Co Manufacture of dimers

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3440154A (en) * 1966-05-02 1969-04-22 Monsanto Co Electrolytic reductive coupling of olefinic compounds

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB967956A (en) * 1960-12-12 1964-08-26 Monsanto Co Manufacture of dimers

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9790161B2 (en) 2010-03-26 2017-10-17 Dioxide Materials, Inc Process for the sustainable production of acrylic acid
US9957624B2 (en) 2010-03-26 2018-05-01 Dioxide Materials, Inc. Electrochemical devices comprising novel catalyst mixtures
US10173169B2 (en) 2010-03-26 2019-01-08 Dioxide Materials, Inc Devices for electrocatalytic conversion of carbon dioxide
US10774431B2 (en) 2014-10-21 2020-09-15 Dioxide Materials, Inc. Ion-conducting membranes
US10975480B2 (en) 2015-02-03 2021-04-13 Dioxide Materials, Inc. Electrocatalytic process for carbon dioxide conversion

Also Published As

Publication number Publication date
DE2849065A1 (de) 1980-05-22
DE2963267D1 (en) 1982-08-19
JPS5572147A (en) 1980-05-30
EP0012215A1 (fr) 1980-06-25

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