US4323714A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Alkylation of hydroxy-substituted aromatic compounds
Assignee: Honeywell UOP LLC
•
Filing: 1980-11-20
•
Granted: 1982-04-06
•
Expires: 2000-11-20
Abstract
Abstract Hydroxy-substituted aromatic compounds may be alkylated by treatment with an alkylating agent such as an olefin or an alcohol at a temperature in the range of from about 50° to about 200° C. and a pressure in the range of from about atmospheric to about 100 atmospheres in the presence of a fluoro-substituted resin. The resulting product will comprise both mono- and di-alkylated hydroxy-substituted aromatic compounds.
Inventors
- 👤 Thomas P. Malloy
- 👤 Dusan J. Engel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 15:21
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/11; C07C37/16; C07C37/14; C07C2603/00; C07C2603/02; C07C2603/04; C07C2603/22; C07C2603/26
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
130 words
A process for the alkylation of a mono- or di-hydroxy-substituted aromatic compound selected from the group consisting of phenol, 1-hydroxynaphthalene, 2-hydroxynaphthalene, anthracene, 2-hydroxyanthracene, 1-hydroxyphenanthrene, 2-hydroxyphenanthrene, 3-hydroxyphenanthrene, 1,2-dihydroxybenzene (catechol), 1,4-dihydroxybenzene (hydroquinone), 1,2-dihydroxynaphthalene, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 1,2-dihydroxyanthracene, and 1,4-dihydroxyanthracene, which comprises treating said mono- or di-hydroxy-substituted aromatic compound with an alkylation agent selected from the group consisting essentially of aliphatic olefins containing from 2 carbon atoms to about 10 carbon atoms in length and alcohols containing from 1 to about 10 carbon atoms in length at a temperature of from about 50° to about 200° C. and a pressure in the range of from about atmospheric pressure to about 100 atmosphere in the presence of a catalyst consisting essentially of a solid perfluorosulfonic acid resin, and recovering the resultant alkylated hydroxy-substituted aromatic compounds.
Claim 2
Dependent Claim
130 words
A process for the alkylation of a mono- or di-hydroxy-substituted aromatic compound selected from the group consisting of phenol, 1-hydroxynaphthalene, 2-hydroxynaphthalene, anthracene, 2-hydroxyanthracene, 1-hydroxyphenanthrene, 2-hydroxyphenanthrene, 3-hydroxyphenanthrene, 1,2-dihydroxybenzene (catechol), 1,4-dihydroxybenzene (hydroquinone), 1,2-dihydroxynaphthalene, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 1,2-dihydroxyanthracene, and 1,4-dihydroxyanthracene, which comprises treating said mono- or di-hydroxy-substituted aromatic compound with an alkylation agent selected from the group consisting essentially of aliphatic olefins containing from 2 carbon atoms to about 10 carbon atoms in length and alcohols containing from 1 to about 10 carbon atoms in length at a temperature of from about 50° to about 200° C. and a pressure in the range of from about atmospheric pressure to about 100 atmosphere in the presence of a catalyst consisting essentially of a solid perfluorosulfonic acid resin, and recovering the resultant alkylated hydroxy-substituted aromatic compounds.
Claim 3
Dependent Claim
16 words
The process as set forth in claim 1 in which said di-hydroxy-substituted aromatic compound is hydroquinone.
Claim 4
Dependent Claim
15 words
The process as set forth in claim 1 in which said di-hydroxy-substituted compound is catechol.
Claim 5
Dependent Claim
15 words
The process as set forth in claim 1 in which said mono-hydroxy-substituted compound is phenol.
Claim 6
Dependent Claim
25 words
The process as set forth in claim 2 in which said alkylating agent is isobutylene and said alkylated hydroxy-substituted aromatic compounds comprise di-t-butylhydroquinone and mono-t-butylhydroquinone.
Claim 7
Dependent Claim
27 words
The process as set forth in claim 3 in which said alcohol alkylating agent is t-butyl alcohol and said alkylated hydroxy-substituted aromatic compounds comprise di-t-butylcatechol and mono-t-butylcatechol.
Claim 8
Dependent Claim
26 words
The process as set forth in claim 4 in which said olefinic alkylating agent is propylene and said alkylated hydroxy-substituted aromatic compounds are diisopropylphenol and monoisopropylphenol.
Claim 9
Dependent Claim
27 words
The process as set forth in claim 2 in which said alcohol alkylating agent is isopropyl alcohol and said alkylated hydroxy-substituted aromatic compounds comprise diisopropylhydroquinone and monoisopropylhydroquinone.
References Cited (Backward Citations)
US3422157A
Cited
US3932537A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-04-05 | 1985-10-05 | 1986-04-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-04-05 | 1989-10-05 | 1990-04-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-04-05 | 1993-10-05 | 1994-04-06 | $7700.00 | Window Closed / Lapsed |