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US4418224A
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Preparation of ortho-alkylated phenols using magnesium compound catalysts
Assignee: General Electric Co
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Filing: 1981-09-18
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Granted: 1983-11-29
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Expires: 2001-09-18
Abstract
Abstract Ortho-alkylated phenols are prepared by reacting phenol unsubstituted in at least one ortho position with an alcohol in the presence of an ortho-alkylation catalyst consisting of magnesium carbonate, magnesium hydroxide or a mixture of both. The catalyst is used in the absence of a promoter compound and with or without polymeric binder.
Inventors
- 👤 James G. Bennett
- 👤 Freddie L. Tungate
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 11:42
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/11; C07C37/16
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
124 words
In a process for alkylating a phenolic compound in the ortho position which comprises the vapor phase reaction in the presence of an alkylation catalyst of an alkylation feed mixture comprising an alkyl alcohol having up to about 16 carbon atoms and a phenolic compound having at least one ortho hydrogen, the phenolic compound represented by the formula ##STR2## wherein R is a monovalent substituent selected from the group consisting of hydrogen, alkyl, phenyl and alkyl substituted phenyl, the improvement comprising conducting the reaction in the presence of a catalyst consisting of a calcination residue derived from heating a magnesium-containing compound wherein said heating which provides a calcination residue takes place in the presence of said alkylation feed mixture in situ in a reactor.
Claim 2
Dependent Claim
124 words
In a process for alkylating a phenolic compound in the ortho position which comprises the vapor phase reaction in the presence of an alkylation catalyst of an alkylation feed mixture comprising an alkyl alcohol having up to about 16 carbon atoms and a phenolic compound having at least one ortho hydrogen, the phenolic compound represented by the formula ##STR2## wherein R is a monovalent substituent selected from the group consisting of hydrogen, alkyl, phenyl and alkyl substituted phenyl, the improvement comprising conducting the reaction in the presence of a catalyst consisting of a calcination residue derived from heating a magnesium-containing compound wherein said heating which provides a calcination residue takes place in the presence of said alkylation feed mixture in situ in a reactor.
Claim 3
Dependent Claim
21 words
A process according to claim 1, in which the reaction is conducted at a temperature in the range of 400°-460° C.
Claim 4
Dependent Claim
13 words
A process according to claim 1, in which the catalyst is magnesium carbonate.
Claim 5
Dependent Claim
19 words
A process according to claim 1, in which the magnesium carbonate is in the form of "basic" magnesium carbonate.
Claim 6
Dependent Claim
15 words
A process according to claim 1, in which the reaction is run above atmospheric pressure.
Claim 7
Dependent Claim
13 words
A process according to claim 1, in which the catalyst is magnesium hydroxide.
Claim 8
Dependent Claim
19 words
A process according to claim 1, in which the catalyst is a mixture of magnesium carbonate and magnesium hydroxide.
Claim 9
Dependent Claim
19 words
A process according to claim 7, in which the magnesium carbonate is in the form of "basic" magnesium carbonate.
Claim 10
Dependent Claim
17 words
A process according to claim 1, where the process is carried out in the presence of water.
Claim 11
Dependent Claim
13 words
A process according to claim 1, in which the alcohol is methyl alcohol.
Claim 12
Dependent Claim
13 words
A process according to claim 1, in which the phenolic compound is phenol.
Claim 13
Dependent Claim
13 words
A process according to claim 1, in which the phenolic compound is o-cresol.
Claim 14
Dependent Claim
18 words
A process according to claim 1, in which the phenolic compound is a mixture of phenol and o-cresol.
Claim 15
Dependent Claim
24 words
The process of claim 1 wherein said magnesium-containing compound is magnesium carbonate, or magnesium hydroxide, or a mixture of magnesium carbonate and magnesium hydroxide.
Claim 16
Dependent Claim
28 words
The process of claim 1 wherein said feed mixture contains at least one mole of alkyl alcohol for each ortho position on the phenolic compound to be alkylated.
Claim 17
Dependent Claim
54 words
The process of claim 1 wherein said feed mixture comprises methanol and phenolic compounds provided by a mixture of phenol and o-cresol, said feed mixture having from about two to about six moles of methanol for each mole of phenolic compound, with phenol constituting at least about 50 mole percent of the phenolic compounds.
Claim 18
Dependent Claim
29 words
The process of claim 1 wherein said feed mixture comprises methanol and phenol, said feed mixture having about two to about six moles of methanol per mole of phenol.
Claim 19
Dependent Claim
13 words
The process of claim 16 or wherein said feed mixture further comprises water.
Claim 20
Dependent Claim
34 words
The process of claim 1 wherein said heating of magnesium carbonate, magnesium hydroxide, or a mixture of the two, takes place at a temperature in a range from about 400° to about 460° C.
Claim 21
Dependent Claim
76 words
In a process for preparing 2,6-xylenol by reacting in the vapor phase, in the presence of an alkylation catalyst, methanol and a mixture of phenol and o-cresol, the improvement comprising conducting the reaction in the presence of a calcination residue derived by heating magnesium carbonate at a temperature in the range 400°-460° C. in the presence of an alkylation feed mixture comprising methanol and a mixture of phenol and o-cresol and in situ in a reactor.
Claim 22
Dependent Claim
76 words
In a process for preparing 2,6-xylenol by reacting in the vapor phase, in the presence of an alkylation catalyst, methanol and a mixture of phenol and o-cresol, the improvement comprising conducting the reaction in the presence of a calcination residue derived by heating magnesium carbonate at a temperature in the range 400°-460° C. in the presence of an alkylation feed mixture comprising methanol and a mixture of phenol and o-cresol and in situ in a reactor.
Claim 23
Dependent Claim
17 words
A process according to claim 20, where the process is carried out in the presence of water.
Claim 24
Dependent Claim
38 words
The process of claim 20 wherein said feed mixture comprises from about 60 to about 90 mole percent methanol, from about 8 to about 20 mole percent phenol, and from about 5 to about 15 mole percent o-cresol.
Claim 25
Dependent Claim
24 words
The process of claim 20 wherein said feed mixture comprises about 4 moles of methanol, about 0.6 mole phenol and about 0.4 mole o-cresol.
Claim 26
Dependent Claim
26 words
The process of claim 20 wherein the liquid hourly space velocity is in a range from about 0.5 hr -1 to about 4.0 hr -1 .
References Cited (Backward Citations)
CA907065A
Cited
US3446856A
Cited
US3873628A
Cited
US3843606A
Cited
US3974229A
Cited
US4041085A
Cited
US3971832A
Cited
US3972836A
Cited
US3968172A
Cited
US4201880A
Cited
US4100207A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-11-28 | 1987-05-30 | 1987-11-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-11-28 | 1991-05-30 | 1991-11-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-11-28 | 1995-05-30 | 1995-11-29 | $7700.00 | Window Closed / Lapsed |