Patent US6374308B1 successfully refreshed from Google Patents.
US3876709A
Expired / Lapsed
US
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Nuclear oxidative of alkyl-substituted phenols in presence of lower alkenoic acid solution of potassium dichromate and manganese acetate
Assignee: BP Corp North America Inc
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Filing: 1972-10-26
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Granted: 1975-04-08
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Expires: 1992-10-26
Abstract
Abstract Derivatives of nuclear coupled alkylphenols, that is nuclear carbon-to-carbon coupling, have higher activity as lubricating oil addition agents than the same derivatives of the parent alkylphenols. For example, sulfonamides or products of the Mannich Reaction derived from coupled p-alkylphenolsulfonyl chloride and an amine or coupled alkylphenol, amine and formaldehyde have higher activity than the same derivatives from the parent p-alkylphenol. Two, three, four, five, six and up to seven molecules of alkylphenol can be coupled through nuclear carbon-to-carbon coupling in the presence of a lower alkanoic acid (e.g., acetic acid) solution of potassium dichromate and manganese acetate.
Inventors
- 👤 Richard J Lee
- 👤 Robert E Karll
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 19:26
CPC Classifications
C; C08; C08G; C08G81/00; C08G81/02; C08G81/021; C07; C07C; C07C37/00; C07C37/11
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
149 words
A METHOD OF NUCLEARLY CARBON-TO-CARBON COUPLING TWO TO SEVEN MOLECULES OF A P-ALKYL-SUBSTITUTED PHENOL, WHEREIN THE ALKYL-SUBSTITUENT HAS A MOLECULAR WEIGHT IN THE RANGE OF 85 TO 3,000, WHICH METHOD COMPRISES SLOWLY ADDING SAID ALKYLPHENOL TO A MIXTURE AT AMBIENT TEMPERATURE WHICH MIXTURE COMPRISES BENZENE AND A GLACIAL ACETIC ACID SOLUTION OF (A) MANGANESE ACETATE IN AN AMOUNT TO PROVIDE 0.3 TO 0.6 GRAM ATOM MANGANESE AND (B) CHROMIC ACID IN AN AMOUNT TO PROVIDE 1 TO 3.5 MOLES BOTH PER MOLE OF SAID ALKYLPHENOL AT A RATE OF ALKYLPHENOL ADDITION TO PROVIDE A TEMPERATURE INCREASE OF 5* TO 30*F, AFTER ADDITION OF SAID ALKYLPHENOL HEATING THE RESULTING MIXTURE TO A TEMPERATURE OF AT LEAST 110*F BUT NOT EXCEEDING 200*F, DISTILLING BENZENE AND WATER CONTAINING 1 TO 3% ACETIC ACID FROM THE REACTION MIXTURE, AND SEPARATING THE COUPLED ALKYLPHENOL PRODUCT FROM CHROMIC ACID, INSOLUBLE METAL SALTS AND ACETIC ACID.
Claim 2
Independent Claim
149 words
A METHOD OF NUCLEARLY CARBON-TO-CARBON COUPLING TWO TO SEVEN MOLECULES OF A P-ALKYL-SUBSTITUTED PHENOL, WHEREIN THE ALKYL-SUBSTITUENT HAS A MOLECULAR WEIGHT IN THE RANGE OF 85 TO 3,000, WHICH METHOD COMPRISES SLOWLY ADDING SAID ALKYLPHENOL TO A MIXTURE AT AMBIENT TEMPERATURE WHICH MIXTURE COMPRISES BENZENE AND A GLACIAL ACETIC ACID SOLUTION OF (A) MANGANESE ACETATE IN AN AMOUNT TO PROVIDE 0.3 TO 0.6 GRAM ATOM MANGANESE AND (B) CHROMIC ACID IN AN AMOUNT TO PROVIDE 1 TO 3.5 MOLES BOTH PER MOLE OF SAID ALKYLPHENOL AT A RATE OF ALKYLPHENOL ADDITION TO PROVIDE A TEMPERATURE INCREASE OF 5* TO 30*F, AFTER ADDITION OF SAID ALKYLPHENOL HEATING THE RESULTING MIXTURE TO A TEMPERATURE OF AT LEAST 110*F BUT NOT EXCEEDING 200*F, DISTILLING BENZENE AND WATER CONTAINING 1 TO 3% ACETIC ACID FROM THE REACTION MIXTURE, AND SEPARATING THE COUPLED ALKYLPHENOL PRODUCT FROM CHROMIC ACID, INSOLUBLE METAL SALTS AND ACETIC ACID.
Claim 3
Dependent Claim
52 words
The method of claim 1 wherein the insoluble metal salts are removed by filtration, chromic acid is removed by phase separation assisted by the addition of C.sub.5 to C.sub.10 alkane hydrocarbon to the mixture of coupled alkylphenol and acetic acid, washing said alkane hydrocarboncontaining phase with water, and distilling acetic acid and
Claim 4
Dependent Claim
75 words
The method of claim 2 wherein said reaction is conducted by adding a benzene diluted aliphatic hydrocarbon solution of the alkyl-substituted phenol to an ambient temperature acetic acid solution of chromic acid and manganese without removing heat of reaction and continuing contact between said alkylphenol and acetic acid solution for 20 hours without addition of heat thereto wherein the aliphatic hydrocarbon solvent is a light grade lubricating oil, hydrocarbon of molecular weight corresponding to said
Claim 5
Dependent Claim
33 words
The method of claim 2 wherein said acetic acid solution is obtained by dissolving potassium dichromate and manganese acetate tetrahydrate in glacial acetic acid with an amount of water to complete dissolution of
Claim 6
Dependent Claim
7 words
A COUPLED ALKYL-SUBSTITUTED PHENOL HAVING THE FORMULA:
Claim 7
Dependent Claim
7 words
A COUPLED ALKYL-SUBSTITUTED PHENOL HAVING THE FORMULA:
Claim 8
Dependent Claim
13 words
The mixture of equal amounts of coupled alkylphenol of claim 5 wherein R
Claim 9
Dependent Claim
12 words
The coupled alkylphenol of claim 5 wherein R is polybutyl radical of
Claim 10
Dependent Claim
13 words
The mixture of equal amounts of coupled alkylphenol of claim 5 wherein R
Claim 11
Dependent Claim
18 words
The coupled alkylphenol of claim 5 wherein R is polypropyl radical of 753 M.sub.n and x is 2.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-04-07 | 1978-10-07 | 1979-04-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-04-07 | 1982-10-07 | 1983-04-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-04-07 | 1986-10-07 | 1987-04-08 | $7700.00 | Window Closed / Lapsed |