GB940378A - Dealkylation of branched-chain ªÐ-alkylated phenols - Google Patents
Dealkylation of branched-chain ªÐ-alkylated phenolsInfo
- Publication number
- GB940378A GB940378A GB1044660A GB1044660A GB940378A GB 940378 A GB940378 A GB 940378A GB 1044660 A GB1044660 A GB 1044660A GB 1044660 A GB1044660 A GB 1044660A GB 940378 A GB940378 A GB 940378A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cresol
- butylphenol
- butyl
- phenol
- isobutylene
- 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
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Phenols containing a secondary or tertiary alkyl group in the p-position are dealkylated by heating them with an aluminium phenoxide in a proportion of 0.1-10% by weight (based on aluminium content) at 150-400 DEG C. at a pressure up to about 10 atm. for a period of at least 1 hour. The process may be applied to mono- or polycyclic mono- or polyhydroxy phenols which may be further alkylated, reference being made to the treatment of o- and m-cresols, xylenols, ethylphenols, cyclohexylphenols, benzylphenols, phenylphenols, naphthols, hydroxyanthracenes and hydroxyphenanthrenes, all containing a branched-chain alkyl group in a p-position. Specified compounds which may be treated are 4-isopropylphenol, 4-sec.- and 4-t butylphenol, 4-t.-butyl-o-cresol, 4-(1,1-dimethylbutyl)-o-cresol, 2,6-dimethyl-4-t.-butylphenol, 2,5-dimethyl-4-t.-butylphenol, 2-ethyl-4-t.-butylphenol, 2-methyl-6-ethyl-4-t.-butylphenol, 2,6-dimethyl-4-(1,1,3,3-tetramethylbutyl) phenol, 4-sec.-nonylphenol, 2,4-di-t.-butylphenol, 4,6-di-t.-butyl-o-cresol, 2-ethyl-4, 6-di-t.-butylphenol, 2, 4, 6-tri-t-butylphenol, 4, 6-di-t.-butyl-m-cresol, 2, 4-dinonyl-phenol, 4,6-dinonyl-o-cresol and 2, 4-di-(1,1,3,3-tetramethylbutyl) phenol. The process is particularly applicable to the treatment of the butylation products of o-cresol from which 6-t.-butyl-o-cresol is to be recovered as the primary product and in this case, after separating the primary product by distillation, the residue containing 4-t.- and 4,6-di-t.-butyl-o-cresol is dealkylated as described above to yield o-cresol and isobutylene for re-use. The aluminium phenoxide may be pre-formed or produced in situ from metallic aluminium and a phenol, preferably the phenol to be dealkylated or the expected dealkylation product. Examples are given in which (1) p-t.-butylphenol yields phenol and isobutylene, (2) 4-t.-butyl-o-cresol or a mixture of 4-t.-and 4,6-di-t.-butyl-o-cresol yield o-cresol and isobutylene, (3) 4,6-di-t.-butyl-m-cresol yield m-cresol and isobutylene and (4) 4,6-dinonyl-o-cresol yield o-cresol and nonenes.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80165059A | 1959-03-24 | 1959-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB940378A true GB940378A (en) | 1963-10-30 |
Family
ID=25181689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1044660A Expired GB940378A (en) | 1959-03-24 | 1960-03-24 | Dealkylation of branched-chain ªÐ-alkylated phenols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB940378A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0286408A1 (en) * | 1987-04-09 | 1988-10-12 | Mitsui Petrochemical Industries, Ltd. | Catalysts for catalytic pyrolysis of phenol distillation residue and process for recovering useful substances by pyrolysis the same |
| CN115745749A (en) * | 2022-11-23 | 2023-03-07 | 江苏迈达新材料股份有限公司 | Method for recycling heavy alkylphenol |
-
1960
- 1960-03-24 GB GB1044660A patent/GB940378A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0286408A1 (en) * | 1987-04-09 | 1988-10-12 | Mitsui Petrochemical Industries, Ltd. | Catalysts for catalytic pyrolysis of phenol distillation residue and process for recovering useful substances by pyrolysis the same |
| CN115745749A (en) * | 2022-11-23 | 2023-03-07 | 江苏迈达新材料股份有限公司 | Method for recycling heavy alkylphenol |
| WO2024108895A1 (en) * | 2022-11-23 | 2024-05-30 | 江苏迈达新材料股份有限公司 | Recycling and reusing method for heavy alkylphenol |
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