GB871830A - Method for the simultaneous production of hydrogen peroxide and carbonyl compounds - Google Patents

Method for the simultaneous production of hydrogen peroxide and carbonyl compounds

Info

Publication number
GB871830A
GB871830A GB106358A GB106358A GB871830A GB 871830 A GB871830 A GB 871830A GB 106358 A GB106358 A GB 106358A GB 106358 A GB106358 A GB 106358A GB 871830 A GB871830 A GB 871830A
Authority
GB
United Kingdom
Prior art keywords
hydrogen peroxide
titanium dioxide
carbonyl compound
reaction
alcohol
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
GB106358A
Inventor
Fujio Mashio
Shinichi Kato
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.)
Fine Organics Inc
Original Assignee
Fine Organics Inc
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 Fine Organics Inc filed Critical Fine Organics Inc
Priority to GB106358A priority Critical patent/GB871830A/en
Publication of GB871830A publication Critical patent/GB871830A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/37Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
    • C07C45/39Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a secondary hydroxyl group
    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01BNON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B15/00Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
    • C01B15/01Hydrogen peroxide
    • C01B15/022Preparation from organic compounds
    • C01B15/026Preparation from organic compounds from alcohols
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/37Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
    • C07C45/38Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group

Landscapes

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

Abstract

Hydrogen peroxide is produced together with a carbonyl compound by the oxidation of a primary or secondary alcohol in the liquid phase with an oxygen-containing gas in the presence of titanium dioxide and ultraviolet light having a wave lenght of 3000-4000 A, e.g. as produced by a mercury lamp. The alcohol may be an aliphatic, aromatic, or hydroaromatic alcohol, e.g. ethanol, isopropanol, benzyl alcohol, or cyclohexanol. Less than 10%, e.g. 1%, of titanium dioxide may be employed. The temperature of reaction may be 50-150 DEG C. The oxygen partial pressure is preferably above 100 mm. of Hg., and may for example be 2 atmos. The reaction vessel may be of glass, aluminium, an alloy of aluminium, tin, porcelain, or another material coated with one of said materials or enamel or a resin. The process may be carried out continuously or intermittently in a reaction vessel provided with reflux condenser and stirrer. Alternatively the reactants and titanium dioxide may be passed continuously through a quartz tube irradiated with ultra-violet light. The concentration of the hydrogen peroxide produced is preferably below 25%. The titanium dioxide may be removed from the reaction products by centrifuging, filtering, or settling. The hydrogen peroxide and carbonyl compound may be separated by fractional distillation, precipitation of the hydrogen peroxide as a metal peroxide, solvent extraction of the carbonyl compound, or by forming an addition compound of the carbonyl compound. In the examples (a) isopropanol and (b) cyclohexanol are treated according to the process claimed to give hydrogen peroxide and (a) acetone and (b) cyclohexanone respectively. In Example 2 a method of separating the acetone from the reaction product is given in which the product is diluted with water containing sodium pyrophosphate and 8-oxyquinoline and the acetone is separated from the resulting mixture by vacuum distillation.ALSO:Hydrogen peroxide is produced together with a carbonyl compound by the oxidation of a primary or secondary alcohol in the liquid phase with an oxygen-containing gas in the presence of titanium dioxide and ultraviolet light having a wavelength of 3000-4000 A, e.g. as produced by a mercury lamp. The alcohol may be an aliphatic, aromatic, or hydroaromatic alcohol, e.g. ethanol, isopropanol, benzyl alcohol, cyclohexanol, benzhydrol, or a -1,2,3,4-tetrahydronaphthol. Less than 10%, e.g. 1%, of titanium dioxide may be employed. The temperature of reaction may be 50-150 DEG C. The oxygen partial pressure is preferably above 100 mm. Hg., and may for example be 2 atmos. The reaction vessel may be of glass, aluminium, an alloy of aluminium, tin, porcelain, or another material coated with one of said materials or enamel or a resin. The process may be carried out continuously or intermittently in a reaction vessel provided with reflux condenser and stirrer. Alternatively the reactants and titanium dioxide may be passed continuously through a quartz tube irradiated with ultraviolet light. The concentration of the hydrogen peroxide produced is preferably below 25%. The titanium dioxide may be removed from the reaction products by centrifuging, filtering, or settling. The hydrogen peroxide and carbonyl compound may be separated by fractional distillation, precipitation of the hydrogen peroxide as a metal peroxide, solvent extraction of the carbonyl compound, or by forming an addition compound of the carbonyl compound. Three examples specifying conditions of reaction are given. According to Example 2, the liquid reaction product is diluted with half its volume of an aqueous solution of sodium pyrophosphate and 8-oxyquinoline, and acetone and isopropanol removed by vacuum distillation leaving a 25% solution of hydrogen peroxide. According to Example 3, the liquid reaction product is diluted with an equal volume of benzene, the hydrogen peroxide is extracted with 0.2 vols. of water giving an 8.5% aqueous solution, and the cyclohexanone also produced is extracted with a 5% aqueous solution of sodium bisulphite and recovered by the addition of potassium carbonate. The unreacted cyclohexanol is recovered from the benzene by distillation.
GB106358A 1958-01-10 1958-01-10 Method for the simultaneous production of hydrogen peroxide and carbonyl compounds Expired GB871830A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB106358A GB871830A (en) 1958-01-10 1958-01-10 Method for the simultaneous production of hydrogen peroxide and carbonyl compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB106358A GB871830A (en) 1958-01-10 1958-01-10 Method for the simultaneous production of hydrogen peroxide and carbonyl compounds

Publications (1)

Publication Number Publication Date
GB871830A true GB871830A (en) 1961-07-05

Family

ID=9715531

Family Applications (1)

Application Number Title Priority Date Filing Date
GB106358A Expired GB871830A (en) 1958-01-10 1958-01-10 Method for the simultaneous production of hydrogen peroxide and carbonyl compounds

Country Status (1)

Country Link
GB (1) GB871830A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4302435A (en) * 1980-09-22 1981-11-24 E. I. Du Pont De Nemours And Company Hydrogenation of a diarylketone to a diarylmethanol
US4897085A (en) * 1989-01-10 1990-01-30 Arco Chemical Technology, Inc. Recovery of hydrogen peroxide
US4897252A (en) * 1989-01-10 1990-01-30 Arco Chemical Technology, Inc. Production of hydrogen peroxide
CN115259099A (en) * 2022-06-13 2022-11-01 四川大学 Preparation of H2O2Photochemical synthesis method of

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4302435A (en) * 1980-09-22 1981-11-24 E. I. Du Pont De Nemours And Company Hydrogenation of a diarylketone to a diarylmethanol
US4897085A (en) * 1989-01-10 1990-01-30 Arco Chemical Technology, Inc. Recovery of hydrogen peroxide
US4897252A (en) * 1989-01-10 1990-01-30 Arco Chemical Technology, Inc. Production of hydrogen peroxide
CN115259099A (en) * 2022-06-13 2022-11-01 四川大学 Preparation of H2O2Photochemical synthesis method of

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