US4474990A
Expired / Lapsed
US
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Preparing p-phenoxy benzoyl compounds
Assignee: Raychem Corp
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Filing: 1982-11-24
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Granted: 1984-10-02
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Expires: 2002-11-24
Abstract
Abstract Substantially pure p-phenoxybenzoyl compounds are prepared by reacting diphenyl ether and an appropriate acyl compound in the presence of hydrogen fluoride. The resulting p-phenoxyaryl alkyl ketone can be converted into p-phenoxybenzoic acid or salts thereof, p-phenoxybenzoyl halide or lower alkyl p-phenoxybenzoate for use preparing homo- and copolymers containing a p-phenoxybenzoyl repeating unit.
Inventors
- 👤 Viktors Jansons
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 10:36
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/45; C07C45/46; C07C49/00; C07C49/76; C07C49/84; C07C51/00; C07C51/16; C07C51/29
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
86 words
A methed for the preparation of p-phenoxybenzoyl compounds of the formula ##STR10## wherein R is lower alkyl, which comprises the mono-acylation of diphenyl ether by reacting diphenyl ether with an acyl compound of the formula ##STR11## wherein R is lower alkyl and R 1 is selected from the group consisting of halogen, hydroxyl, --OR 2 and ##STR12## where R 2 and R 3 are each lower alkyl, in the presence of hydrogen fluoride as the sole catalyst for the reaction, to obtain the mono-acylated, para isomer.
Claim 2
Dependent Claim
86 words
A methed for the preparation of p-phenoxybenzoyl compounds of the formula ##STR10## wherein R is lower alkyl, which comprises the mono-acylation of diphenyl ether by reacting diphenyl ether with an acyl compound of the formula ##STR11## wherein R is lower alkyl and R 1 is selected from the group consisting of halogen, hydroxyl, --OR 2 and ##STR12## where R 2 and R 3 are each lower alkyl, in the presence of hydrogen fluoride as the sole catalyst for the reaction, to obtain the mono-acylated, para isomer.
Claim 3
Dependent Claim
32 words
A method in accordance with claim 1, wherein hydrogen fluoride is present in an amount of at least 30 percent by weight based on the weight of diphenyl ether and acyl compound.
Claim 4
Dependent Claim
34 words
A method in accordance with claim 2, wherein said hydrogen fluoride is present in an amount of at least 50% by weight based on the total weight of the diphenyl ether and acyl compound.
Claim 5
Dependent Claim
26 words
A method in accordance with claim 1, wherein said reaction is conducted at a temperature in the range of from about -20° to about +70° C.
Claim 6
Dependent Claim
26 words
A method in accordance with claim 1, wherein said reaction is conducted at a temperature in the range of from about -10° to about -30° C.
Claim 7
Independent Claim
37 words
A method for the preparation of substantially pure p-phenoxyacetophenone which comprises reacting diphenyl ether with an acyl compound selected from the group consisting of acetyl chloride, acetic acid and acetic anhydride in the presence of hydrogen fluoride.
Claim 8
Independent Claim
37 words
A method for the preparation of substantially pure p-phenoxyacetophenone which comprises reacting diphenyl ether with an acyl compound selected from the group consisting of acetyl chloride, acetic acid and acetic anhydride in the presence of hydrogen fluoride.
Claim 9
Dependent Claim
14 words
A method in accordance with claim 6, wherein said acyl compound is acetyl chloride.
Claim 10
Dependent Claim
14 words
A method in accordance with claim 6, wherein said acyl compound is acetic acid.
Claim 11
Dependent Claim
14 words
A method in accordance with claim 6, wherein said acyl compound is acetic anhydride.
Claim 12
Dependent Claim
32 words
A method in accordance with claim 6, wherein hydrogen fluoride is present in an amount of at least 30 percent by weight based on the weight of diphenyl ether and acyl compound.
Claim 13
Dependent Claim
34 words
A method in accordance with claim 10, wherein said hydrogen fluoride is present in an amount of at least 50% by weight based on the total weight of the diphenyl ether and acyl compound.
Claim 14
Dependent Claim
26 words
A method in accordance with claim 6, wherein said reaction is conducted at a temperature in the range of from about -20° to about +70° C.
Claim 15
Dependent Claim
26 words
A method in accordance with claim 12, wherein said reaction is conducted at a temperature in the range of from about -10° to about +30° C.
Claim 16
Independent Claim
90 words
A method of preparing substantially pure p-phenoxybenzoic acid which comprises reacting diphenyl ether with an acyl compound of the formula ##STR13## wherein R is lower alkyl and R 1 is selected from the group consisting of halogen, hydroxyl, --OR 2 and ##STR14## where R 2 and R 3 are each lower alkyl, in the presence of hydrogen fluoride as the sole catalyst for the reaction, to produce a compound of the formula ##STR15## wherein R is lower alkyl, and then oxidizing the compound produced to yield substantially pure p-phenoxybenzoic acid.
Claim 17
Independent Claim
90 words
A method of preparing substantially pure p-phenoxybenzoic acid which comprises reacting diphenyl ether with an acyl compound of the formula ##STR13## wherein R is lower alkyl and R 1 is selected from the group consisting of halogen, hydroxyl, --OR 2 and ##STR14## where R 2 and R 3 are each lower alkyl, in the presence of hydrogen fluoride as the sole catalyst for the reaction, to produce a compound of the formula ##STR15## wherein R is lower alkyl, and then oxidizing the compound produced to yield substantially pure p-phenoxybenzoic acid.
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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) | 1987-10-02 | 1988-04-02 | 1988-10-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-10-02 | 1992-04-02 | 1992-10-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-10-02 | 1996-04-02 | 1996-10-02 | $7700.00 | Window Closed / Lapsed |