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GB894135A - The production of cyclohexanone oxime - Google Patents

The production of cyclohexanone oxime

Info

Publication number
GB894135A
GB894135A GB13418/59A GB1341859A GB894135A GB 894135 A GB894135 A GB 894135A GB 13418/59 A GB13418/59 A GB 13418/59A GB 1341859 A GB1341859 A GB 1341859A GB 894135 A GB894135 A GB 894135A
Authority
GB
United Kingdom
Prior art keywords
stage
excess
cyclohexanone
hydroxylamine
hydroxylamine sulphate
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.)
Expired
Application number
GB13418/59A
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.)
Inventa AG fuer Forschung und Patentverwertung
Original Assignee
Inventa AG fuer Forschung und Patentverwertung
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 Inventa AG fuer Forschung und Patentverwertung filed Critical Inventa AG fuer Forschung und Patentverwertung
Publication of GB894135A publication Critical patent/GB894135A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32Oximes
    • C07C251/34Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/44Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01BNON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B21/00Nitrogen; Compounds thereof
    • C01B21/082Compounds containing nitrogen and non-metals and optionally metals
    • C01B21/14Hydroxylamine; Salts thereof
    • C01B21/1409Preparation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/04Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/04Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
    • C07C249/08Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A process for the continuous production of cyclohexanone oxime comprises forming a hydroxylamine sulphate solution by bringing an ammonium nitrite solution containing ammonium carbonate and/or ammonium bicarbonate into contact with excess sulphur dioxide in a cooled vessel in a circulating system, the hydroxylamine disulphonate formed being maintained in excess relative to the reactants entering the vessel, and from which the disulphonate solution containing at the most 6 gm. per litre of free sulphur dioxide and having a pH of 1.5-2.5 is removed, hydrolysing the disulphonate at elevated temperature to form hydroxylamine sulphate, reacting the hydroxylamine sulphate with cyclohexanone in two stages at a temperature sufficient to maintain the oxine formed in the molten state, the cyclohexanone being present in excess in the first stage which is effected using partly exhausted hydroxylamine sulphate solution from the second stage, and hydroxylamine sulphate being present in excess in the second stage, separating the molten oxime from the effluent from the second stage and recycling the residue, the acid present being neutralised. An example is furnished. The conversion of cyclohexanone oxime to caprolactam by Beckmann transformation is mentioned. Specification 677,386 is referred to.
GB13418/59A 1958-04-23 1959-04-20 The production of cyclohexanone oxime Expired GB894135A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH894135X 1958-04-23

Publications (1)

Publication Number Publication Date
GB894135A true GB894135A (en) 1962-04-18

Family

ID=4546047

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13418/59A Expired GB894135A (en) 1958-04-23 1959-04-20 The production of cyclohexanone oxime

Country Status (1)

Country Link
GB (1) GB894135A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1271711B (en) * 1963-11-30 1968-07-04 Stamicarbon Process for the preparation of cyclohexanone oxime

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1271711B (en) * 1963-11-30 1968-07-04 Stamicarbon Process for the preparation of cyclohexanone oxime

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