EP4632111A3 - Process for the preparation of acetals of alpha-chloro- or alpha-bromo-aldehydes - Google Patents

Process for the preparation of acetals of alpha-chloro- or alpha-bromo-aldehydes

Info

Publication number
EP4632111A3
EP4632111A3 EP25169473.3A EP25169473A EP4632111A3 EP 4632111 A3 EP4632111 A3 EP 4632111A3 EP 25169473 A EP25169473 A EP 25169473A EP 4632111 A3 EP4632111 A3 EP 4632111A3
Authority
EP
European Patent Office
Prior art keywords
aliphatic
alpha
cycloaliphatic
acetals
aldehydes
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.)
Pending
Application number
EP25169473.3A
Other languages
German (de)
French (fr)
Other versions
EP4632111A2 (en
Inventor
Simon HORSINKA
Dominik Weis
Siegfried Reinhart WALDVOGEL
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.)
Merck Patent GmbH
Original Assignee
Esy Labs 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 Esy Labs GmbH filed Critical Esy Labs GmbH
Publication of EP4632111A2 publication Critical patent/EP4632111A2/en
Publication of EP4632111A3 publication Critical patent/EP4632111A3/en
Pending legal-status Critical Current

Links

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
    • 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
    • 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
    • C25B11/043—Carbon, e.g. diamond or graphene
    • 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
    • C25B3/11—Halogen 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
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/20—Processes
    • C25B3/27—Halogenation
    • 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

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)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)

Abstract

Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Acetalen aliphatischer oder cycloaliphatischer α-Chlor- oder α-Bromaldehyde, umfassend die Elektrolyse eines flüssigen Reaktionsgemischs, enthaltend
i) einen Halogenakzeptor, der ausgewählt ist unter
- primären aliphatischen oder cycloaliphatischen Alkoholen,
- Mono-1-alkyenylethern aliphatischer Diole und
- Gemischen, die einen Mono-1-alkyenylether eines aliphatischen, cycloaliphatischen oder aromatischen Alkohols und wenigstens einen aliphatischen oder cycloaliphatischen Alkohol umfassen,

ii) wenigstens eine Halogenquelle, die Chlor oder Brom enthält,
iii) wenigstens ein Lösungsmittel und
iv) wenigstens ein Leitsalz
in einer ungeteilten Elektrolysezelle.The present invention relates to a process for the production of acetals of aliphatic or cycloaliphatic α-chloroaldehyde or α-bromoaldehyde, comprising the electrolysis of a liquid reaction mixture containing
i) a halogen acceptor selected from
- primary aliphatic or cycloaliphatic alcohols,
- Mono-1-alkyenyl ethers of aliphatic diols and
- Mixtures comprising a mono-1-alkyenyl ether of an aliphatic, cycloaliphatic or aromatic alcohol and at least one aliphatic or cycloaliphatic alcohol,

ii) at least one halogen source containing chlorine or bromine,
iii) at least one solvent and
iv) at least one conducting salt
in an undivided electrolysis cell.

EP25169473.3A 2024-04-10 2025-04-09 Process for the preparation of acetals of alpha-chloro- or alpha-bromo-aldehydes Pending EP4632111A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP24169503 2024-04-10

Publications (2)

Publication Number Publication Date
EP4632111A2 EP4632111A2 (en) 2025-10-15
EP4632111A3 true EP4632111A3 (en) 2026-02-11

Family

ID=90720472

Family Applications (1)

Application Number Title Priority Date Filing Date
EP25169473.3A Pending EP4632111A3 (en) 2024-04-10 2025-04-09 Process for the preparation of acetals of alpha-chloro- or alpha-bromo-aldehydes

Country Status (1)

Country Link
EP (1) EP4632111A3 (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090107849A1 (en) * 2006-05-15 2009-04-30 Hans Lammers Electrochemical process to prepare a halogenated carbonyl group-containing compound
CN115852397A (en) * 2022-10-19 2023-03-28 西南林业大学 Preparation method of halogenated indole compound
EP4253603A1 (en) * 2022-03-28 2023-10-04 Evonik Operations GmbH Electrochemical oxidation of cycloalkanes to cycloalkanone compounds

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2411826A (en) 1946-11-26 Haloacetals
US2330570A (en) 1943-09-28 Halo acetal
US2803668A (en) 1957-08-20 Process for making chloroacetal
US3940259A (en) 1973-05-07 1976-02-24 Velsicol Chemical Corporation Dioxane substituted-α-haloanilides as herbicides
US4532338A (en) 1983-07-13 1985-07-30 Ppg Industries, Inc. Process for producing 2-halomethyl-1,3-cyclic acetal
DE102015204901A1 (en) 2015-03-18 2016-09-22 Wacker Chemie Ag Process for the preparation of chloroacetaldehyde acetals

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090107849A1 (en) * 2006-05-15 2009-04-30 Hans Lammers Electrochemical process to prepare a halogenated carbonyl group-containing compound
EP4253603A1 (en) * 2022-03-28 2023-10-04 Evonik Operations GmbH Electrochemical oxidation of cycloalkanes to cycloalkanone compounds
CN115852397A (en) * 2022-10-19 2023-03-28 西南林业大学 Preparation method of halogenated indole compound

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DONALD A WHITE ET AL: "Syntheses with Electrogenerated Halogens Part III. Oxidation of Primary Alcohols to Acetals of 2-Haloaldehydes", J OF THE ELECTROCHEMICAL SOCIETY,, vol. 125, no. 9, 1 September 1978 (1978-09-01), pages 1401 - 1404, XP001284127 *
DONG XICHANG ET AL: "Merging shuttle reactions and paired electrolysis for reversible vicinal dihalogenations", SCIENCE - AUTHOR MANUSCRIPT, vol. 371, no. 6528, 29 January 2021 (2021-01-29), US, pages 507 - 514, XP093204995, ISSN: 0036-8075, DOI: 10.1126/science.abf2974 *
KAPUSTINA N I ET AL: "OXIDATION OF ALIPHATIC ALCOHOLS BY A SYSTEM CONTAINING Na2S2O8 AND A METAL CHLORIDE", RUSS CHEM BULL, vol. 37, 1 August 1988 (1988-08-01), pages 1730 - 1732, XP093304655, DOI: 10.1007/BF00961139 *
TORII S ET AL: "HIGHLY CONVENIENT ELECTROLYSIS PROCEDURE FOR THE PREPARATION OF ALPHA-HALOGENATED KETONES AND ACETALS FROM ENOL ACETATES, ENOL ETHERS, AND SILYL ENOL ETHERS", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, UNITED STATES, vol. 45, 1 January 1980 (1980-01-01), pages 2731 - 2735, XP000775554, ISSN: 0022-3263, DOI: 10.1021/JO01301A044 *

Also Published As

Publication number Publication date
EP4632111A2 (en) 2025-10-15

Similar Documents

Publication Publication Date Title
EP0260587B1 (en) Solutions of fluoropolymers and their use
JPS61170588A (en) Production of quaternary ammonium hydroxide
EP4632111A3 (en) Process for the preparation of acetals of alpha-chloro- or alpha-bromo-aldehydes
EP0000493B1 (en) Process for the preparation of 1-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (h acid).
AU623865B2 (en) Process for the preparation of fluorinated acrylic acids and derivatives thereof
US1422869A (en) Esters of dioxydiethylsulphide and process of making same
EP0088285B1 (en) Process for producing fluorocarbon polymers that contain carboxyl groups, some starting materials therefor and the fluorosulphate compounds occurring as intermediates in the process
EP0087737A1 (en) Perfluorinated vinyl ethers with a secondary hydrogen atom, their polymers and process for preparing the monomers
DE2362648A1 (en) METHOD FOR PRODUCING HALOGENOPENOLS
EP1375490A1 (en) Process for the production of 2-acetyl-2-chloro-gamma-butyrolactone
DE2534558A1 (en) Hydroxy-phenyl-isopropylbenzene prepn. - from substd. isopropylbenzens and phenols catalysed by sulphonated polystyrene crosslinked by divinylbenzene
EP0285972A2 (en) Process for the preparation of 2,4-diaminobenzenesulfonic acid
DE753345C (en) Process for the production of amide-like condensation products
DE845341C (en) Process for the production of low-caustic alkali alcoholates
DE847442C (en) Process for the production of fluorine-containing olefins
DE69720432T2 (en) METHOD FOR PRODUCING 2-HYDROXYNAPHTALIN-3,6-DICARBON ACID
IT1047770B (en) PERFECTION IN PERMEABLE MEMBRANE ELECTROLYTIC CELLS IN PARTICULAR FOR THE USE IN THE PRODUCTION OF CHLORINE AND HYDROXIDE OF AN ALKALINE METAL
DE102018215611B4 (en) Electrochemical synthesis of S-arylthiocarbamates
SU577255A1 (en) Method of preparing mixture of aliphatic dicarboxylic acid diesters
DE2242513A1 (en) PROCESS FOR THE PRODUCTION OF 4-CHLORNAPHTHALIC ANHYDRIDE
DE2262851C3 (en) Process for the preparation of phenylhydroxylamines
EP0866064A1 (en) Improved process for the preparation of trifluoromethyloxirane
AT226664B (en) Process for the preparation of 2,3-dichloropropene (1) and propargyl chloride
DE903814C (en) Process for the manufacture of sulphonation products
DE2657234B2 (en) Process for the production of halonitrobenzenes

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN PUBLISHED

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC ME MK MT NL NO PL PT RO RS SE SI SK SM TR

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC ME MK MT NL NO PL PT RO RS SE SI SK SM TR

RIC1 Information provided on ipc code assigned before grant

Ipc: C25B 3/07 20210101AFI20260105BHEP

Ipc: C25B 3/11 20210101ALI20260105BHEP

Ipc: C25B 3/27 20210101ALI20260105BHEP

Ipc: C25B 3/29 20210101ALI20260105BHEP

Ipc: C25B 11/043 20210101ALI20260105BHEP

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: MERCK KGAA

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: MERCK PATENT GMBH