GB870787A - Improvements in or relating to the preparation of oximes - Google Patents

Improvements in or relating to the preparation of oximes

Info

Publication number
GB870787A
GB870787A GB43401/59A GB4340159A GB870787A GB 870787 A GB870787 A GB 870787A GB 43401/59 A GB43401/59 A GB 43401/59A GB 4340159 A GB4340159 A GB 4340159A GB 870787 A GB870787 A GB 870787A
Authority
GB
United Kingdom
Prior art keywords
ketone
oxime
ketoxime
methyl
para
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
GB43401/59A
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.)
Commercial Solvents Corp
Original Assignee
Commercial Solvents Corp
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 Commercial Solvents Corp filed Critical Commercial Solvents Corp
Publication of GB870787A publication Critical patent/GB870787A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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

Landscapes

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

Abstract

Aldoximes or ketoximes derived from a ketone in which at least one of the carbon atoms alpha to the carbonyl group is unsubstituted are prepared by heating the parent aldehyde or ketone with an oxime of lower molecular weight than the said aldoxime or ketoxime in the presence of an acidic catalyst, the carbonyl compound from which the lower molecular weight oxime is derived having a lower boiling point than the said aldehyde or ketone reactant and preferably being distilled off. Oximes such as acetoxime, methyl ethyl ketoxime, methyl propyl ketoxime, methyl butyl ketoxime, ethyl butyl ketoxime, methyl aryl ketoximes, formaldoxime, acetaldoxime, butyraldoxime and hexanaldoxime are heated with carbonyl compounds such as acetone, diethyl ketone, dipropyl ketone, methyl ethyl ketone, methyl propyl ketone, methyl aryl ketones, ethyl butyl ketone, cyclopropanone, cyclohexanone, acetophenone, butyraldehyde and hexanol in the presence of acidic catalysts such as sulphuric, hydrochloric, phosphoric, formic, benzenesulphonic, toluenesulphonic and naphthalenesulphonic acids; sodium bisulphate, primary ammonium phosphate, calcium chloride, zinc chloride, aluminium chloride, ammonium chloride or bromide, hydroxylammonium chloride and borontrifluoride-ether complex to give products such as methyl ethyl ketoxime, dipropyl ketoxime, cyclohexanone oxime, acetoneveratrone oxime, hexanaldoxime, butyraldoxime, acetophenone oxime, 2-aceto-para-cymeneoxime, para-chloroacetophenone oxime, 3-menthoneoxime, pinacoloneoxime, 2, 4-pentanediketoxime, 2,5-hexane diketoxime, meta-nitroacetophenoneoxime, ortho: para-dimethylacetophenoneoxime, 1,4-cyclohexane diketoxime, cyclopentanone oxime, anisaldoxime, 4-acetoxy-3-methoxy-benzaldoxime, 2,4-dihydroxybenzaldoxime, para-dimethyl-amino-benzaldoxime, para-nitrobenzaldoxime, cumaldoxime and hexadecaldoxime.
GB43401/59A 1959-01-16 1959-12-21 Improvements in or relating to the preparation of oximes Expired GB870787A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US870787XA 1959-01-16 1959-01-16

Publications (1)

Publication Number Publication Date
GB870787A true GB870787A (en) 1961-06-21

Family

ID=22202991

Family Applications (1)

Application Number Title Priority Date Filing Date
GB43401/59A Expired GB870787A (en) 1959-01-16 1959-12-21 Improvements in or relating to the preparation of oximes

Country Status (1)

Country Link
GB (1) GB870787A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0218123A1 (en) * 1985-09-28 1987-04-15 Bayer Ag Process for the preparation of hydroxy-benzaldoxime-O-ethers
US12031060B1 (en) * 2022-12-19 2024-07-09 Patcham Usa Llc Efficient MEKO-free anti-skinning agent

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0218123A1 (en) * 1985-09-28 1987-04-15 Bayer Ag Process for the preparation of hydroxy-benzaldoxime-O-ethers
US4739118A (en) * 1985-09-28 1988-04-19 Bayer Aktiengesellschaft Process for the preparation of hydroxybenzaldoxime O-ethers
US12031060B1 (en) * 2022-12-19 2024-07-09 Patcham Usa Llc Efficient MEKO-free anti-skinning agent

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