GB681990A - Oxidation of aromatic hydrocarbons - Google Patents
Oxidation of aromatic hydrocarbonsInfo
- Publication number
- GB681990A GB681990A GB203149A GB203149A GB681990A GB 681990 A GB681990 A GB 681990A GB 203149 A GB203149 A GB 203149A GB 203149 A GB203149 A GB 203149A GB 681990 A GB681990 A GB 681990A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkali
- dimethylcarbinol
- alkyl
- aryl
- alcohols
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
- C07C409/10—Cumene hydroperoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
- C07C409/12—Compounds containing six-membered aromatic rings with two alpha,alpha-dialkylmethyl hydroperoxy groups bound to carbon atoms of the same six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Compounds of the formula Ar-CHR1R2 (R1 and R2 are alkyl and Ar is aryl or alkaryl) are oxidized by passing in an oxygen-containing gas in the liquid phase at 20-95 DEG C. at atmospheric pressure or above 95 DEG C. at superatmospheric pressure in the presence of water or aqueous alkali, the ratio of aqueous medium to oxidant being less than 1 : 1 by weight, e.g. 1 : 10-1 : 3. The alkali may be a metal hydroxide (e.g. sodium, potassium, lithium, calcium or barium), an organic base (e.g. a tetraalkylammonium or trimethylbenzylammonium hydroxide), a metal carbonate or bicarbonate (e.g. sodium) or an alkali metal salt of a weak organic acid. There may be used as catalyst activated carbon or a metal salt, which may be water-soluble such as potassium permanganate potassium stearate, manganese acetate, ferrous sulphate, cobalt nitrate or cobalt acetate, or oil-soluble such as manganese linoleate or manganese butyl phthalate. The products are mainly alcohols Ar-CR1R2OH or peroxides Ar-CR1R2OOH, depending on the reaction conditions, but dihydric alcohols, acids and ketones may also be obtained. Low temperatures, absence of alkali, and high catalyst concentration favour the production of alcohols whereas high temperatures with alkali and little or no catalyst give high yields of peroxides. The reaction is facilitated by the addition of an organic peroxide as initiator, e.g. one of the oxidation products dissolved in unchanged starting material. The reaction mixture is separated into the aqueous and oily layers, the former being acidified to precipitate organic acids. The oily layer is alkali-extracted to remove acids and, if desired, fractionally distilled under reduced pressure. If peroxides are not required, they may be decomposed by heat before the mixture is distilled. In the examples: p-cymene is oxidized to p-methylacetophenone, p-tolyl-dimethylcarbinol and the corresponding hydroperoxide and cumic and other acids, e.g. p-toluic and terephthalic; cumene is oxidized to phenyl-dimethylcarbinol and the hydroperoxide, acetophenone and other unspecified products; di-isopropylbenzene yields p-isopropylphenyl-dimethylcarbinol and the hydroperoxide, p-isopropylacetophenone, p-acetylphenyl-dimethylcarbinol, p-phenylene-bis-dimethylcarbinol and the corresponding bishydroperoxide; sec.-butylbenzene gives acetophenone and phenylmethylethylcarbinol. Other specified starting materials are those in which the aryl nucleus is naphthalene, anthracene or phenanthrene and/or is substituted by methyl, ethyl, propyl, isopropyl or any of the butyl groups. Similarly R1 and R2 may be any of these alkyl groups and may be the same or different. If the starting material is a solid it is dissolved in a solvent such as benzene. Specifications 610,293, 616,330, 630,286, 641,250 and 654,035 are referred to.ALSO:Hydroperoxides obtained by oxidizing compounds of the type Aryl-CH (alkyl)2 (see Group IV (b)) are useful in kier boiling, bleaching and other textile operations. a a -Dimethylbenzylhydroperoxide is specified. The corresponding alcohols are good wetting-out agents.ALSO:Products obtained by oxidizing compounds of the type Aryl-CH(alkyl)2 (see Group IV(b)) are used as perfume bases for soaps. Phenyldimethylcarbinol p-tolyldimethylcarbinol and the ketones produced in the oxidation are especially suitable.ALSO:Products obtained by oxidizing compounds of the type Aryl-CH(alkyl)2 (see Group IV(b)) are used for separating materials by flotation. Thus p-tolyl-dimethylcarbinol is a frothing agent for copper, zinc and lead sulphide ores; phenyldimethylcarbinol and the dihydric alcohols such as those derived from di-isopropylbenzenes have similar applications, as well as the corresponding hydroperoxides. Alkali salts of cumic acid may be used in the separation of potassium and sodium salts by flotation.ALSO:Hydroperoxides obtained by oxidising alkyl substituted aromatic compounds of the formula <FORM:0681990/V/1> in which R1 and R2 represent alkyl groups, and Ar an aryl or alkaryl group (see Group IV (b)), are useful in rubber reclaiming; a a -dimethylbenzyl hydroperoxide is specified.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB203149A GB681990A (en) | 1949-01-25 | 1949-01-25 | Oxidation of aromatic hydrocarbons |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB203149A GB681990A (en) | 1949-01-25 | 1949-01-25 | Oxidation of aromatic hydrocarbons |
Publications (1)
Publication Number | Publication Date |
---|---|
GB681990A true GB681990A (en) | 1952-11-05 |
Family
ID=9732395
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB203149A Expired GB681990A (en) | 1949-01-25 | 1949-01-25 | Oxidation of aromatic hydrocarbons |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB681990A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE969266C (en) * | 1951-04-28 | 1958-05-14 | Rhone Poulenc Sa | Process for the production of cumene hydroperoxide by the catalytic oxidation of cumene |
DE1253692B (en) * | 1962-01-12 | 1967-11-09 | Allied Chem | Process for the production of aromatically substituted carbinols |
CN102199114A (en) * | 2011-03-11 | 2011-09-28 | 北京化工大学 | Method for preparing raw material for producing dicumyl peroxide |
CN102911096A (en) * | 2012-10-31 | 2013-02-06 | 华南理工大学 | Method for synthetizing cumene hydroperoxide by catalytic oxidation of cumene |
WO2019119489A1 (en) * | 2017-12-21 | 2019-06-27 | 万华化学集团股份有限公司 | Method of preparing ethylbenzene hydroperoxide by liquid-phase peroxidation of ethylbenzene and preparation method of propylene oxide |
-
1949
- 1949-01-25 GB GB203149A patent/GB681990A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE969266C (en) * | 1951-04-28 | 1958-05-14 | Rhone Poulenc Sa | Process for the production of cumene hydroperoxide by the catalytic oxidation of cumene |
DE1253692B (en) * | 1962-01-12 | 1967-11-09 | Allied Chem | Process for the production of aromatically substituted carbinols |
CN102199114A (en) * | 2011-03-11 | 2011-09-28 | 北京化工大学 | Method for preparing raw material for producing dicumyl peroxide |
CN102199114B (en) * | 2011-03-11 | 2013-12-04 | 北京化工大学 | Method for preparing raw material for producing dicumyl peroxide |
CN102911096A (en) * | 2012-10-31 | 2013-02-06 | 华南理工大学 | Method for synthetizing cumene hydroperoxide by catalytic oxidation of cumene |
WO2019119489A1 (en) * | 2017-12-21 | 2019-06-27 | 万华化学集团股份有限公司 | Method of preparing ethylbenzene hydroperoxide by liquid-phase peroxidation of ethylbenzene and preparation method of propylene oxide |
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