GB1214060A - A method of oxidizing a secondary alkyl-substituted toluene - Google Patents
A method of oxidizing a secondary alkyl-substituted tolueneInfo
- Publication number
- GB1214060A GB1214060A GB47784/68A GB4778468A GB1214060A GB 1214060 A GB1214060 A GB 1214060A GB 47784/68 A GB47784/68 A GB 47784/68A GB 4778468 A GB4778468 A GB 4778468A GB 1214060 A GB1214060 A GB 1214060A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sodium
- secondary alkyl
- potassium
- alkyl
- formula
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
Abstract
1,214,060. Oxidation of secondary-alkyl toluenes. SUMITOMO CHEMICAL CO. Ltd. 9 Oct., 1968 [16 Oct., 1967; 19 July, 1968], No. 47784/68. Heading C2C. A method for producing cresols, benzene dicarboxylic acids, secondary alkyl benzoic acids and toluene tertiary hydroperoxides comprises reacting a secondary alkyl toluene of the formula wherein R is a methyl group and R<SP>1</SP> is a methyl or ethyl group, with oxygen or air at 50-150‹ C. in water and in the presence of sodium and/or potassium, the amount of sodium or potassium present being at least 0À12 atomic equivalent per mole of secondary alkyl toluene, or a mixture thereof, the sodium and/or potassium being provided by one or more sodium or potassium carbonates or bicarbonates or by a mixture of salts including at least 10% of the said carbonates or bicarbonates and up to 90% of a sodium or potassium salt of a benzene-carboxylic acid having the formula wherein R<SP>11</SP> is a hydrogen atom, a carboxyl or methyl group or a secondary alkyl group -CHRR<SP>1</SP> where R and R<SP>1</SP> are as defined above or an alkyl carbonyl, hydroxy alkyl or alkenyl group derived from the -CHRR<SP>1</SP> group, until the content of hydroperoxide in the oily layer formed has become 15-25% by weight, thereby obtaining a tertiary hydroperoxide of the Formula I in the oily layer and a sodium or potassium salt of a secondary alkyl benzoic acid of the Formula II in the aqueous layer; the oily layer and aqueous layers are separated and the hydroperoxide I is cleaned at 50-100‹ C. in the presence of an acidic catalyst to form the corresponding cresol, the secondary alkyl benzoic acid II may be oxidized either in the form of its sodium or potassium salt or after acidification to the free acid to obtain the corresponding benzene dicarboxylic acid. The oxidation of the secondary alkyl toluene may be carried out in the presence of an emulsifier, e.g. palmitic or stearic acid and catalysts such as cobalt-amine complex salts, phthalocyanine copper or molybdenum disulphide.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6667967 | 1967-10-16 | ||
| JP5131568 | 1968-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1214060A true GB1214060A (en) | 1970-12-02 |
Family
ID=26391850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47784/68A Expired GB1214060A (en) | 1967-10-16 | 1968-10-09 | A method of oxidizing a secondary alkyl-substituted toluene |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3647866A (en) |
| BE (1) | BE722344A (en) |
| CH (1) | CH509964A (en) |
| DE (1) | DE1803036A1 (en) |
| DK (1) | DK131463B (en) |
| FR (1) | FR1596609A (en) |
| GB (1) | GB1214060A (en) |
| NL (2) | NL6814710A (en) |
| YU (1) | YU34670B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1128549A (en) * | 1978-12-14 | 1982-07-27 | Lewis B. Young | Production of 3-methylphenol |
| US5600026A (en) * | 1992-05-27 | 1997-02-04 | Sumitomo Chemical Company, Limited | Process for production of cresols |
| DE69317401T2 (en) * | 1992-07-01 | 1998-07-16 | Sumitomo Chemical Co | METHOD FOR PRODUCING CRESOLS |
| PL181496B1 (en) * | 1996-03-20 | 2001-07-31 | Politechnika Slaska Im Wincent | Method of obtaining beta-naphtole |
-
0
- NL NL136650D patent/NL136650C/xx active
-
1968
- 1968-10-08 US US765969A patent/US3647866A/en not_active Expired - Lifetime
- 1968-10-09 GB GB47784/68A patent/GB1214060A/en not_active Expired
- 1968-10-14 DE DE19681803036 patent/DE1803036A1/en active Pending
- 1968-10-14 FR FR1596609D patent/FR1596609A/fr not_active Expired
- 1968-10-15 NL NL6814710A patent/NL6814710A/xx unknown
- 1968-10-15 DK DK495668AA patent/DK131463B/en not_active IP Right Cessation
- 1968-10-15 BE BE722344D patent/BE722344A/xx not_active IP Right Cessation
- 1968-10-15 YU YU2392/68A patent/YU34670B/en unknown
- 1968-10-16 CH CH1548468A patent/CH509964A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH509964A (en) | 1971-07-15 |
| BE722344A (en) | 1969-03-14 |
| DK131463B (en) | 1975-07-21 |
| FR1596609A (en) | 1970-06-22 |
| YU239268A (en) | 1979-07-10 |
| US3647866A (en) | 1972-03-07 |
| DK131463C (en) | 1975-12-08 |
| NL136650C (en) | |
| YU34670B (en) | 1979-12-31 |
| DE1803036A1 (en) | 1969-08-07 |
| NL6814710A (en) | 1969-04-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR830003396A (en) | Method for producing aromatic dicarboxylic acid | |
| GB1214060A (en) | A method of oxidizing a secondary alkyl-substituted toluene | |
| ES390527A2 (en) | Process for preparing glycol esters from olefinically unsaturated compounds | |
| IE42680L (en) | Process for the preparation of propylene oxide | |
| KR830007496A (en) | Process for preparing unsaturated acids and esters | |
| SE8005389L (en) | SET TO MAKE CARBOXYLIC ACIDS FROM ALDEHYDES | |
| US3068280A (en) | Process for production of aromatic carboxylic acids | |
| DE1262282B (en) | Process for the production of phenols by oxidizing aromatic hydrocarbons | |
| US2821551A (en) | Process for production of aromatic carboxylic acids | |
| KR880011066A (en) | (Phenylethenyl) phenylpropionic acid and esters thereof and (benzoylphenyl) propionic acid or a method for producing the ester | |
| Mosher et al. | The Oxidation of Isoborneol with Chromic Acid1 | |
| KR890008065A (en) | Method for preparing alpha-branched C_12-C_40 fatty acid | |
| JPS55153741A (en) | Improved preparation of carboxylic acid ester | |
| US2824130A (en) | Production of alpha hydroxyisobutyric acid | |
| US3557196A (en) | Process for preparing beta-keto-acids | |
| GB681990A (en) | Oxidation of aromatic hydrocarbons | |
| DE1960520A1 (en) | Phenols from alkyl benzenes | |
| JPS56152456A (en) | Preparation of hydroperoxide | |
| JPS55149247A (en) | Preparation of aromatic hydroperoxide | |
| DE870253C (en) | Process for the preparation of Oxyaetiocholenic acid | |
| GB738420A (en) | Treatment of alkyl ustilate esters | |
| GB942415A (en) | Preparation of adipic and alkyladipic acids | |
| JPS58162540A (en) | Production of alpha-aryl-tertiary-alcohol | |
| DE2844195A1 (en) | NEW CATALYST AND ITS USE FOR THE PRODUCTION OF PHENOLS | |
| GB837321A (en) | Improvements in and relating to an oxidation process for the production of aromatic carboxylic acids |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |