GB354798A - Improvements in and relating to oxidation of organic compounds - Google Patents

Improvements in and relating to oxidation of organic compounds

Info

Publication number
GB354798A
GB354798A GB516730A GB516730A GB354798A GB 354798 A GB354798 A GB 354798A GB 516730 A GB516730 A GB 516730A GB 516730 A GB516730 A GB 516730A GB 354798 A GB354798 A GB 354798A
Authority
GB
United Kingdom
Prior art keywords
selenium
oxidized
methylene
group
compound
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
GB516730A
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB516730A priority Critical patent/GB354798A/en
Publication of GB354798A publication Critical patent/GB354798A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/185—Saturated compounds containing keto groups bound to acyclic carbon atoms containing —CHO groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/12—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing more than one —CHO group
    • C07C47/127—Glyoxal
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/12—Ketones containing more than one keto group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/86—Ketones containing a keto group bound to a six-membered aromatic ring containing —CHO groups

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

Selenium dioxide, selenious acid or a selenite are used for oxidizing organic carbonyl compounds having directly attached to the carbonyl group at least one methylene (CH2) or methyl (CH3) group. The methylene or methyl group so attached is oxidized and the selenium compound reduced. According to one example, acetone is boiled under reflux with selenium dioxide until the latter is completely reduced, and the selenium is then separated from the liquid.ALSO:Oxygenated organic compounds are converted into more highly oxygenated organic compounds (other than carbon dioxide) by treating organic carbonyl compounds having directly attached to the carbonyl group at least one methylene (CH2) or methyl (CH3) group with selenium dioxide, selenious acid or a selenite. The organic carbonyl compound may be either an aliphatic or an alicyclic compound or an aromatic compound which contains no methylene or methyl groups directly linked to the aromatic nucleus. Reaction is preferably effected in presence of a diluent or of excess of the organic carbonyl compound itself, at temperatures of 50-150 DEG C. In examples, acetone is oxidized by selenium dioxide to pyruvic aldehyde-the oxide being thereby reduced to selenium itself, similarly methylethylketone is oxidized to a mixture of diacetyl and ethylglyoxal, diethylketone to b .g -diketo-n-pentane, acetophenone to phenylglyoxal, propiophenone to acetylbenzoyl, cyclohexanone to cyclohexa-1,2-dione (which may be purified by conversion to a semicarbazone), acetaldehyde (or paraldehyde) to glyoxal or its polymerides, propionaldehyde to methylglyoxal, butyraldehyde to ethylglyoxal, ethyl-malonate to ethyl-mesoxalate or its hydrate, and ethylacetoacetate to ethyl-a .b -diketobutyrate. Cyclopentanone and other cyclic ketones may be oxidized in a similar manner.
GB516730A 1930-02-15 1930-02-15 Improvements in and relating to oxidation of organic compounds Expired GB354798A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB516730A GB354798A (en) 1930-02-15 1930-02-15 Improvements in and relating to oxidation of organic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB516730A GB354798A (en) 1930-02-15 1930-02-15 Improvements in and relating to oxidation of organic compounds

Publications (1)

Publication Number Publication Date
GB354798A true GB354798A (en) 1931-08-17

Family

ID=9790936

Family Applications (1)

Application Number Title Priority Date Filing Date
GB516730A Expired GB354798A (en) 1930-02-15 1930-02-15 Improvements in and relating to oxidation of organic compounds

Country Status (1)

Country Link
GB (1) GB354798A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110818542A (en) * 2019-11-27 2020-02-21 怀化旺达生物科技有限公司 Purification method of 1, 2-cyclohexanedione

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110818542A (en) * 2019-11-27 2020-02-21 怀化旺达生物科技有限公司 Purification method of 1, 2-cyclohexanedione

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