GB797217A - Process for the production of cyclohexanone oxime and o-alkyl ethers thereof - Google Patents

Process for the production of cyclohexanone oxime and o-alkyl ethers thereof

Info

Publication number
GB797217A
GB797217A GB20495/55A GB2049555A GB797217A GB 797217 A GB797217 A GB 797217A GB 20495/55 A GB20495/55 A GB 20495/55A GB 2049555 A GB2049555 A GB 2049555A GB 797217 A GB797217 A GB 797217A
Authority
GB
United Kingdom
Prior art keywords
sulphate
nitrocyclohexane
dialkyl
cyclohexanone oxime
added
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
GB20495/55A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB797217A publication Critical patent/GB797217A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/44—Oximes 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

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

Abstract

Cyclohexanone oxime and o-alkyl ethers thereof are prepared by reacting a dialkyl sulphate with at least one salt of nitrocyclohexane in the presence of a solution of alkali metal hydroxide. Preferably, the dialkyl sulphate is added to the nitrocyclohexane salt and the alkali metal hydroxide solution, the temperature during the addition being maintained above 15 DEG C. After the addition of the dialkyl sulphate, the products may be obtained from the reaction mixture by bringing it to a pH below 7 and recovering the cyclohexanone oxime and o-alkyl ether thereof, by extraction. The cyclohexanone oxime and o-alkyl ether thereof can be separated by vacuum distillation. A salt of hydroxylamine can be added to the reaction mixture following the dialkyl sulphate so as to enhance the yield. The process may be carried out batchwise or continuously. Specified salts of nitrocyclohexane are the sodium, potassium and ammonium salts. Specified dialkyl sulphates are the dimethyl, diethyl, di-n-propyl and diisobutyl sulphates. Specified solvents for the alkali metal hydroxide are water, methanol, ethanol and isopropanol. In examples: (1) dimethyl sulphate is added to a solution of nitrocyclohexane in aqueous sodium hydroxide; (2) as in (1) but using diethyl sulphate and aqueous potassium hydroxide; (3) as in (1) but using an ethanol solution of a mixture of sodium and potassium hydroxides; (4) as in (1) but hydroxylamine hydrochloride added after the dimethyl sulphate.
GB20495/55A 1954-10-25 1955-07-15 Process for the production of cyclohexanone oxime and o-alkyl ethers thereof Expired GB797217A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US797217XA 1954-10-25 1954-10-25

Publications (1)

Publication Number Publication Date
GB797217A true GB797217A (en) 1958-06-25

Family

ID=22152371

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20495/55A Expired GB797217A (en) 1954-10-25 1955-07-15 Process for the production of cyclohexanone oxime and o-alkyl ethers thereof

Country Status (1)

Country Link
GB (1) GB797217A (en)

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