US4108908A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of thio-acid compounds
Assignee: Zeneca Inc
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Filing: 1977-02-18
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Granted: 1978-08-22
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Expires: 1997-02-18
Abstract
Abstract Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.0-9.0 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous, manganous or chromic chelate of a thio-acid compound. The mixture may optionally contain a surfactant.
Inventors
- 👤 Thomas F. Rutledge
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 22:59
CPC Classifications
C; C07; C07C; C07C46/00; C07C46/02; C07C46/06; C07C46/08; C07C37/00; C07C37/11
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
78 words
A method of preparing a condensation product of an "alkylphenol", an "alkoxyphenol" or a "1-naphthol", by an oxidative coupling reaction said method comprising contacting an aqueous mixture of the phenol or naphthol with oxygen or oxygen containing gas in the presence of sufficient amount of alkaline material to sustain pH in the range of about 7.0-9.0 during the oxidative coupling reaction and a catalyst system comprising a cupric, manganous, cobaltous, or chromic metal complex of a thio acid.
Claim 2
Independent Claim
78 words
A method of preparing a condensation product of an "alkylphenol", an "alkoxyphenol" or a "1-naphthol", by an oxidative coupling reaction said method comprising contacting an aqueous mixture of the phenol or naphthol with oxygen or oxygen containing gas in the presence of sufficient amount of alkaline material to sustain pH in the range of about 7.0-9.0 during the oxidative coupling reaction and a catalyst system comprising a cupric, manganous, cobaltous, or chromic metal complex of a thio acid.
Claim 3
Dependent Claim
16 words
A method, as claimed in claim 1, wherein the aqueous phenol mixture additionally comprises a surfactant.
Claim 4
Dependent Claim
32 words
A method, as claimed in claim 2, wherein the surfactant is sodium lauryl sulfate and is present in an amount equal to at least 0.005 mols per mol of phenol or naphthol.
Claim 5
Dependent Claim
13 words
A method, as claimed in claim 1, wherein the phenol is an alkylphenol.
Claim 6
Dependent Claim
13 words
A method, as claimed in claim 4, wherein the alkylphenol is a 2,6-dialkylphenol.
Claim 7
Dependent Claim
22 words
A method, as claimed in claim 4, wherein the alkyl groups of said alkylphenol contain from 1 to about 12 carbon atoms.
Claim 8
Dependent Claim
12 words
A method, as claimed in claim 5, wherein the alkylphenol is 2,6-xylenol.
Claim 9
Dependent Claim
22 words
A method, as claimed in claim 4, wherein the alkyl groups of said alkylphenol contain from 1 to about 5 carbon atoms.
Claim 10
Dependent Claim
17 words
A method, as claimed in claim 1, wherein the catalyst system comprises a cupric thio acid complex.
Claim 11
Dependent Claim
12 words
A method, as claimed in claim 9 wherein the alkylphenol is 2,6-xylenol.
Claim 12
Dependent Claim
19 words
A method, as claimed in claim 9, wherein the cupric thio acid complex is cupric complex of mercaptoacetic acid.
Claim 13
Dependent Claim
27 words
A method, as claimed in claim 1, wherein the amount of metal complex is equal to at least about 0.2 mmols per mol of phenol or naphthol.
Claim 14
Dependent Claim
16 words
A method, as claimed in claim 1, wherein the alkaline material is an alkali metal hydroxide.
Claim 15
Dependent Claim
15 words
A method, as claimed in claim 13, wherein the alkali metal hydroxide is sodium hydroxide.
Claim 16
Dependent Claim
27 words
A method, as claimed in claim 1, wherein the amount of alkaline material is equal to at least about 3 mmols per mol of phenol or napthol.
Claim 17
Dependent Claim
17 words
A method, as claimed in claim 1, wherein the metal complex and surfactant are a single compound.
Claim 18
Dependent Claim
55 words
A method, as claimed in claim 1, wherein the phenol is an alkylphenol having the following formula: ##STR23## wherein R 2 and R 6 are alkyl and R 3 and R 5 are hydrogen or alkyl and R 4 is hydrogen or methyl provided that R 3 and R 5 cannot be both tertiary alkyl.
Claim 19
Dependent Claim
13 words
A method, as claimed in claim 17, wherein the alkyl phenol is 2,4,6-trimethylphenol.
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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) | 1981-08-21 | 1982-02-20 | 1982-08-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-08-21 | 1986-02-20 | 1986-08-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-08-21 | 1990-02-20 | 1990-08-22 | $7700.00 | Window Closed / Lapsed |