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US3974229A
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Preparation of ortho-alkylated phenols
Assignee: General Electric Co
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Filing: 1971-02-11
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Granted: 1976-08-10
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Expires: 1991-02-11
Abstract
Abstract There are provided alkylation catalysts comprising magnesium oxide mixed with and bonded by manganese oxides. These are used in processes for the vapor phase ortho-alkylation of phenols with an alcohol. The present catalysts are advantageous in that they provide a substantially increased total useful life, a reduced induction period for maximum reaction selectivity, elimination of catalyst losses in comparison with the powders or weakly sintered composites of the prior art and increased selectivity for ortho-substitution. Treatment of the new catalysts with methanol vapor before use enhances their activity in converting phenols to 2,6-xylenol and results in a significant increase in production rate.
Inventors
- 👤 Bernardus J. Van Sorge
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 04:52
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/11; C07C37/16; B; B01; B01J; B01J23/00; B01J23/16; B01J23/32; B01J23/34; B01J37/00
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
79 words
In a process for alkylating a phenol in the ortho position which comprises the vapor phase reaction in the presence of an alkylation catalyst of an alkyl alcohol and a phenol compound having the general formula: ##SPC2## where R is a monovalent substituent from the group consisting of hydrogen, alkyl, phenyl and alkyl substituted phenyl; the improvement comprising conducting the reaction in the presence of a catalyst comprising magnesium oxide bonded with from 1-15% by weight of manganese oxides.
Claim 2
Dependent Claim
79 words
In a process for alkylating a phenol in the ortho position which comprises the vapor phase reaction in the presence of an alkylation catalyst of an alkyl alcohol and a phenol compound having the general formula: ##SPC2## where R is a monovalent substituent from the group consisting of hydrogen, alkyl, phenyl and alkyl substituted phenyl; the improvement comprising conducting the reaction in the presence of a catalyst comprising magnesium oxide bonded with from 1-15% by weight of manganese oxides.
Claim 3
Dependent Claim
11 words
The process of claim 1 wherein said alcohol is methyl alcohol.
Claim 4
Dependent Claim
17 words
The process of claim 2 wherein the catalyst is maintained at a temperature of at least 420°C.
Claim 5
Dependent Claim
14 words
The process of claim 2 wherein each R in said phenol compound is hydrogen.
Claim 6
Dependent Claim
11 words
The process of claim 2 wherein said phenol compound is ortho-cresol.
Claim 7
Dependent Claim
16 words
The process of claim 2 wherein said phenol compound is a mixture of phenol and ortho-cresol.
Claim 8
Dependent Claim
27 words
The process of claim 1 wherein said manganese oxides are selected from the group consisting of manganese oxide, dimanganese trioxide, trimanganese tetroxide, manganese heptoxide and mixtures thereof.
Claim 9
Dependent Claim
33 words
The process of claim 1 wherein the manganese oxide binder is substantially free of sulfate ions and is formed by precipitation from an aqueous solution of manganese sulfate by contact with an alkali.
Claim 10
Dependent Claim
20 words
The process of claim 1 wherein the manganese oxides comprise from 1 to 15% by weight of the total catalyst.
Claim 11
Dependent Claim
20 words
The process of claim 1 wherein the manganese oxides comprise from 2 to 10% by weight of the total catalyst.
Claim 12
Dependent Claim
26 words
The process of claim 1 including the step of enhancing the activity of the catalyst by exposing it to methanol vapor before conducting the alkylation reaction.
Claim 13
Dependent Claim
29 words
The process of claim 11 wherein the catalyst is exposed to methanol vapor at a temperature of at least about 250°C. until activation of the catalyst is substantially complete.
Claim 14
Dependent Claim
56 words
In a process for alkylating phenol in the ortho position to form 2,6-xylenol which comprises the vapor phase reaction in the presence of an alkylation catalyst of an alkyl alcohol and phenol; the improvement comprising conducting the reaction in the presence of a catalyst comprising magnesium oxide bonded with from 1-15% by weight of manganese oxides.
Claim 15
Dependent Claim
56 words
In a process for alkylating phenol in the ortho position to form 2,6-xylenol which comprises the vapor phase reaction in the presence of an alkylation catalyst of an alkyl alcohol and phenol; the improvement comprising conducting the reaction in the presence of a catalyst comprising magnesium oxide bonded with from 1-15% by weight of manganese oxides.
Claim 16
Dependent Claim
83 words
In a process for alkylating a phenol in the ortho position which comprises the vapor phase reaction in the presence of an alkylation catalyst of an alkyl alcohol and a phenol compound having the general formula: ##SPC3## where R is a monovalent substituent from the group consisting of hydrogen, alkyl, phenyl and alkyl substituted phenyl; the improvement comprising conducting the reaction in the presence of a methanol vapor activated catalyst which comprises magnesium oxide bonded with from 1-15% by weight of manganese oxides.
Claim 17
Dependent Claim
83 words
In a process for alkylating a phenol in the ortho position which comprises the vapor phase reaction in the presence of an alkylation catalyst of an alkyl alcohol and a phenol compound having the general formula: ##SPC3## where R is a monovalent substituent from the group consisting of hydrogen, alkyl, phenyl and alkyl substituted phenyl; the improvement comprising conducting the reaction in the presence of a methanol vapor activated catalyst which comprises magnesium oxide bonded with from 1-15% by weight of manganese oxides.
Claim 18
Dependent Claim
105 words
In a process for alkylating a phenol in the ortho position which comprises the vapor phase reaction in the presence of an alkylation catalyst of an alkyl alcohol and a phenol compound having the general formula: ##SPC4## wherein R is a monovalent substituent from the group consisting of hydrogen, alkyl, phenyl and alkyl substituted phenyl; the improvement which comprises conducting the reaction in the presence of a catalyst prepared by blending a mixture of magnesium oxide with from 1-15% by weight of manganese oxide with about an equal amount of water, molding the blend to shape, and heating at a calcination temperature of from 300-850°.
Claim 19
Dependent Claim
105 words
In a process for alkylating a phenol in the ortho position which comprises the vapor phase reaction in the presence of an alkylation catalyst of an alkyl alcohol and a phenol compound having the general formula: ##SPC4## wherein R is a monovalent substituent from the group consisting of hydrogen, alkyl, phenyl and alkyl substituted phenyl; the improvement which comprises conducting the reaction in the presence of a catalyst prepared by blending a mixture of magnesium oxide with from 1-15% by weight of manganese oxide with about an equal amount of water, molding the blend to shape, and heating at a calcination temperature of from 300-850°.
References Cited (Backward Citations)
GB717588A
Cited
US3446856A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-08-10 | 1980-02-09 | 1980-08-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-10 | 1984-02-09 | 1984-08-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-10 | 1988-02-09 | 1988-08-10 | $7700.00 | Window Closed / Lapsed |