US5288922A
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US
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Process of preparing diaryl ethers over a dealuminated zeolite catalyst
Assignee: Dow Chemical Co
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Filing: 1992-07-16
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Granted: 1994-02-22
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Expires: 2012-07-16
Abstract
Abstract A process of preparing diaryl ethers, such as diphenyl oxide, involving dehydrating a hydroxy-substituted aromatic compound, such as phenol, over a zeolite catalyst. The preferred zeolites are dealuminated acid mordenite and dealuminated zeolite Y.
Inventors
- 👤 Gary R. Buske
- 👤 Juan M. Garces
- 👤 William P. Dianis
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 04:11
CPC Classifications
C; C07; C07C; C07C41/00; C07C41/01; C07C41/09
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
87 words
A process of preparing a diaryl ether comprising contacting a hydroxy-substituted aromatic compound with a catalytic amount of a zeolite selected from the group consisting of dealuminated acidic mordenite, zeolite β and dealuminated zeolite L, the mordenite zeolite being characterized as having a silica to alumina molar ratio of at least about 40 and the β and L zeolites being characterized as having a silica to alumina molar ratio of at least about 20, the contacting occurring under reaction conditions such that a diaryl ether is formed.
Claim 2
Dependent Claim
87 words
A process of preparing a diaryl ether comprising contacting a hydroxy-substituted aromatic compound with a catalytic amount of a zeolite selected from the group consisting of dealuminated acidic mordenite, zeolite β and dealuminated zeolite L, the mordenite zeolite being characterized as having a silica to alumina molar ratio of at least about 40 and the β and L zeolites being characterized as having a silica to alumina molar ratio of at least about 20, the contacting occurring under reaction conditions such that a diaryl ether is formed.
Claim 3
Dependent Claim
25 words
The process of claim 1 wherein the hydroxy-substituted aromatic compound is phenol or an α- or β-hydroxy-substituted fused aromatic ring system, or substituted derivatives thereof.
Claim 4
Dependent Claim
12 words
The process of claim 2 wherein the hydroxy-substituted aromatic compound is phenol.
Claim 5
Dependent Claim
18 words
The process of claim 1 wherein a gaseous or liquid diluent is employed with the hydroxy-substituted aromatic compound.
Claim 6
Dependent Claim
11 words
The process of claim 1 wherein the zeolite is acidic mordenite.
Claim 7
Dependent Claim
25 words
The process of claim 5 wherein the mordenite zeolite has a silica to alumina molar ratio in the range from about 50 to about 500.
Claim 8
Dependent Claim
27 words
The process of claim 5 wherein the mordenite is prepared from a starting mordenite having a Symmetry Index in the range from about 0.5 to about 1.3.
Claim 9
Dependent Claim
23 words
The process of claim 1 wherein the reaction conditions comprise a temperature in the range from about 200° C. to about 550° C.
Claim 10
Dependent Claim
29 words
The process of claim 1 wherein the hydroxy-substituted aromatic compound is in a liquid phase and the reaction conditions comprise a pressure ranging from sub-atmospheric to about 1500 psig.
Claim 11
Dependent Claim
29 words
The process of claim 1 wherein the hydroxy-substituted aromatic compound is in a vapor phase and the reaction conditions comprise a pressure ranging from sub-atmospheric to about 200 psig.
Claim 12
Dependent Claim
27 words
The process of claim 1 wherein the reaction conditions comprise a weight hourly space velocity ranging from about 0.01 hr -1 to about 10 hr -1 .
Claim 13
Dependent Claim
12 words
The process of claim 1 wherein the diaryl ether is diphenyl ether.
Claim 14
Dependent Claim
36 words
The process of claim 1 wherein the hydroxy-substituted aromatic compound is reacted in a conversion of at least about 10 weight percent and with a selectivity to diaryl ether of at least about 40 mole percent.
Claim 15
Dependent Claim
36 words
The process of claim 1 wherein the hydroxy-substituted aromatic compound is reacted in a conversion of at least about 20 weight percent and with a selectivity to diaryl ether of at least about 60 mole percent.
Claim 16
Dependent Claim
40 words
The process of claim 1 wherein the catalyst is regenerated by burn-off in air or oxygen, and optionally in the presence of an inert gaseous diluent, at a temperature in the range from about 300° C. to about 700° C.
Claim 17
Dependent Claim
29 words
The process of claim 1 wherein the weight percentage of diaryl ether in the observed products, excluding hydroxy-substituted aromatic compound and solvent, is at least about 70 weight percent.
Claim 18
Dependent Claim
82 words
A process of preparing diphenyl oxide comprising contacting liquid phenol with a dealuminated acidic mordenite zeolite having a silica to alumina molar ratio of at least about 40 at a temperature in the range from about 200° C. to about 450° C. and at a pressure in the range from sub-atmospheric to about 1500 psig such that the phenol conversion is at least about 20 weight percent and diphenyl oxide is formed in a selectivity of at least about 80 mole percent.
Claim 19
Dependent Claim
82 words
A process of preparing diphenyl oxide comprising contacting liquid phenol with a dealuminated acidic mordenite zeolite having a silica to alumina molar ratio of at least about 40 at a temperature in the range from about 200° C. to about 450° C. and at a pressure in the range from sub-atmospheric to about 1500 psig such that the phenol conversion is at least about 20 weight percent and diphenyl oxide is formed in a selectivity of at least about 80 mole percent.
Claim 20
Dependent Claim
90 words
A process of preparing a diaryl ether comprising contacting a hydroxy-substituted aromatic compound with a catalytic amount of a dealuminated zeolite Y having a silica to alumina molar ratio greater than 20, the contacting occurring at a temperature in the range from about 200° C. to about 300° C. and under reaction conditions such that diaryl ether is formed in a selectivity of greater than about 70 weight percent, measured as the weight percentage of diaryl ether found in the observed products excluding hydroxy-substituted aromatic compound and any optional solvent.
Claim 21
Dependent Claim
90 words
A process of preparing a diaryl ether comprising contacting a hydroxy-substituted aromatic compound with a catalytic amount of a dealuminated zeolite Y having a silica to alumina molar ratio greater than 20, the contacting occurring at a temperature in the range from about 200° C. to about 300° C. and under reaction conditions such that diaryl ether is formed in a selectivity of greater than about 70 weight percent, measured as the weight percentage of diaryl ether found in the observed products excluding hydroxy-substituted aromatic compound and any optional solvent.
Claim 22
Dependent Claim
29 words
The process of claim 18 wherein the hydroxy-substituted aromatic compound is selected from the group consisting of phenol, α- and β-hydroxy-substituted fused aromatic ring compounds, and substituted derivatives thereof.
Claim 23
Dependent Claim
12 words
The process of claim 18 wherein the hydroxy-substituted aromatic compound is phenol.
Claim 24
Dependent Claim
17 words
The process of claim 18 wherein a diluent or solvent is employed with the hydroxy-substituted aromatic compound.
Claim 25
Dependent Claim
23 words
The process of claim 18 wherein the reaction conditions comprise a temperature in the range from about 225° C. to about 275° C.
Claim 26
Dependent Claim
29 words
The process of claim 18 wherein the hydroxy-substituted aromatic compound is in a liquid phase and the reaction conditions comprise a pressure ranging from sub-atmospheric to about 1500 psig.
Claim 27
Dependent Claim
29 words
The process of claim 18 wherein the hydroxy-substituted aromatic compound is in a gaseous phase and the reaction conditions comprise a pressure ranging from sub-atmospheric to about 200 psig.
Claim 28
Dependent Claim
26 words
The process of claim 18 wherein the reaction conditions comprise a weight hourly space velocity ranging from 0.01 hr -1 to about 10 hr -1 .
Claim 29
Dependent Claim
12 words
The process of claim 18 wherein the diaryl ether is diphenyl ether.
Claim 30
Dependent Claim
23 words
The process of claim 18 wherein the weight percentage of diaryl ether in the observed products is at least about 80 weight percent.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-02-21 | 1997-08-23 | 1998-02-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-02-21 | 2001-08-23 | 2002-02-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-02-21 | 2005-08-23 | 2006-02-22 | $7700.00 | Window Closed / Lapsed |