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US4101392A
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Process for electrolytic oxidative methyl-methyl coupling of cresol salts
Assignee: Monsanto Co
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Filing: 1976-12-22
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Granted: 1978-07-18
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Expires: 1996-12-22
Abstract
Abstract Cresol salts substituted with non-interfering, blocking substituents at least at the 2,4,6-positions relative to the phenolic oxyanion where at least one of the substituents is the cresolic methyl are electrolytically oxidized to yield methyl-methyl coupled dehydrodimeric cresols.
Inventors
- 👤 Richard C. Hallcher
- 👤 Manuel M. Baizer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 13:59
CPC Classifications
C; C25; C25B; C25B3/00; C25B3/20; C25B3/29; C25B3/01; C25B3/07
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
117 words
An improved process for electrolytic oxidative methyl-methyl coupling of cresol salts substituted with non-interfering, blocking substituents at least at the 2, 4, 6-positions relative to the phenolic oxyanion where at least one of the substituents is the cresolic methyl, which process comprises electrolytic oxidation at the anode by electrolysis at no more than about 0.5 volts (versus the saturated calomel electrode) in a liquid electrolysis medium comprising the cresol salt, the corresponding free cresol, and a substantially non-nucleophilic solvent, wherein the molar equivalent ratio of cresol salt to free cresol is no more than about 1.0 molar equivalent of cresol salt to about 5.0 molar equivalents of free cresol, and thereafter recovering a methyl-methyl coupled dehydrodimeric cresol.
Claim 2
Dependent Claim
117 words
An improved process for electrolytic oxidative methyl-methyl coupling of cresol salts substituted with non-interfering, blocking substituents at least at the 2, 4, 6-positions relative to the phenolic oxyanion where at least one of the substituents is the cresolic methyl, which process comprises electrolytic oxidation at the anode by electrolysis at no more than about 0.5 volts (versus the saturated calomel electrode) in a liquid electrolysis medium comprising the cresol salt, the corresponding free cresol, and a substantially non-nucleophilic solvent, wherein the molar equivalent ratio of cresol salt to free cresol is no more than about 1.0 molar equivalent of cresol salt to about 5.0 molar equivalents of free cresol, and thereafter recovering a methyl-methyl coupled dehydrodimeric cresol.
Claim 3
Dependent Claim
13 words
The process of claim 1 wherein the cresol salt is a 2,4,6-trialkylphenol salt.
Claim 4
Dependent Claim
13 words
The process of claim 2 wherein the 2,4,6-trialkylphenol salt is a 2,6-di-t-butyl-4-methylphenol salt.
Claim 5
Dependent Claim
13 words
The process of claim 2 wherein the 2,4,6-trialkylphenol salt is a 2,4,6-trimethylphenol salt.
Claim 6
Dependent Claim
25 words
The process of claim 1 wherein the cresol salt is a Group 1a metal or tetraalkylphenoxide and the methyl-methyl coupled dehydrodimeric cresol is a 1,2-bis(3,5-dialkyl-hydroxyphenyl)ethane.
Claim 7
Dependent Claim
20 words
The process of claim 5 wherein the Group 1a or tetraalkylammonium 2,4,6-trialkylphenoxide is sodium 2,6-di-t-butyl-4-methylphenoxide and the 1,2-bis(3,5-dialkyl-hydroxyphenyl)ethane is 1,2-bis(3,5-di-t-butyl-4-hydroxyphenyl)ethane.
Claim 8
Dependent Claim
20 words
The process of claim 5 wherein the Group 1a or tetraalkylammonium 2,4,6-trialkylphenoxide is sodium 2,4,6-trimethylphenoxide and the 1,2-bis(3,5-dialkyl-hydroxyphenyl)ethane is 1,2-bis(2-hydroxy-3,5-dimethylphenyl)ethane.
Claim 9
Dependent Claim
20 words
The process of claim 5 wherein the Group 1a or tetralkylammonium 2,4,6-trialkylphenoxide is tetra-n-butylammonium 2,4,6-trimethylphenoxide and the 1,2-bis(3,5-dialkyl-hydroxyphenyl)ethane is 1,2-bis(2-hydroxy-3,5-dimethylphenyl)ethane.
Claim 10
Dependent Claim
11 words
The process of claim 1 wherein the electrolysis medium is basic.
Claim 11
Dependent Claim
11 words
The process of claim 1 wherein the solvent is substantially anhydrous.
Claim 12
Dependent Claim
12 words
The process of claim 10 wherein the substantially anhydrous solvent is acetonitrile.
Claim 13
Dependent Claim
14 words
The process of claim 1 wherein the solvent contains small amounts of added water.
Claim 14
Dependent Claim
16 words
The process of claim 12 wherein the solvent containing small amounts of added water is acetonitrile.
Claim 15
Dependent Claim
21 words
The process of claim 12 wherein the concentration of the small amounts of added water is about 10 percent by volume.
Claim 16
Dependent Claim
11 words
The process of claim 1 wherein a supporting electrolyte is used.
Claim 17
Dependent Claim
23 words
The process of claim 15 wherein the concentration of the supporting electrolyte is between about 1.0 percent and about 15 percent by weight.
Claim 18
Dependent Claim
14 words
The process of claim 15 wherein the supporting electrolyte is a quaternary ammonium salt.
Claim 19
Dependent Claim
13 words
The process of claim 17 wherein the quaternary ammonium salt is tetraethylammonium perchlorate.
Claim 20
Dependent Claim
17 words
The process of claim 1 wherein a graphite felt anode and a platinum screen cathode are used.
Claim 21
Dependent Claim
38 words
The process of claim 1 wherein the molar equivalent ratio of cresol salt to the corresponding free cresol is between about 1.0 molar equivalent of cresol salt to between about 10 and 25 molar equivalents of free cresol.
Claim 22
Dependent Claim
48 words
The process of claim 1 wherein the concentration of cresol salt in the electrolysis medium is between about 1.0 percent and about 15 percent by weight; the anode potential is sufficient to effect oxidative methyl-methyl coupling of the cresol salt; and the electrolysis is conducted at ambient temperatures.
References Cited (Backward Citations)
US3756928A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-07-17 | 1982-01-16 | 1982-07-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-07-17 | 1986-01-16 | 1986-07-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-07-17 | 1990-01-16 | 1990-07-18 | $7700.00 | Window Closed / Lapsed |