US4514577A
Expired / Lapsed
US
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Chemical process for preparing di-ortho benzyl phenols
Assignee: Albemarle Corp
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Filing: 1982-10-15
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Granted: 1985-04-30
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Expires: 2002-10-15
Abstract
Abstract Phenols having an unsubstituted ortho-position are benzylated by reaction with a benzyl alcohol in contact with an activated alumina catalyst especially gamma alumina at a temperature sufficient to maintain the reactants in the vapor phase.
Inventors
- 👤 Allen H. Filbey
- 👤 Henry G. Braxton, Jr.
- 👤 Bernard R. Meltsner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 09:53
CPC Classifications
C; C11; C11B; C11B5/00; C11B5/0021; C11B5/0035; C07; C07C; C07C37/00; C07C37/11; C07C37/16; C07C41/00; C07C41/01; C07C41/09; C07C45/00; C07C45/002; C08; C08K; C08K5/00; C08K5/04; C08K5/13; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/18; C10L1/182; C10L1/1822; C10L1/1826; C10M; C10M129/00; C10M129/02; C10M129/04; C10M129/10; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/28; C10M2207/281; C10M2207/282; C10M2207/283; C10M2207/286; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/084; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/06; C10M2215/064; C10M2215/065; C10M2215/24; C10M2215/26; C10M2217/00; C10M2217/04; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/04; C10M2219/046; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/041; C10M2229/00; C10M2229/04; C10M2229/041; C10N; C10N2040/00; C10N2040/25; C10N2040/251; C10N2040/255; C10N2040/28
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
77 words
A process for making benzyl substituted phenols, said process comprising contacting a mixture of a phenol and a benzyl alcohol in the vapor phase with an activated gamma alumina catalyst at a temperature in the range of 225°-450° C., said temperature being high enough to maintain said phenol and benzyl alcohol in the vapor phase at reaction conditions, said phenol having at least one position ortho or para to its phenolic hydroxyl group unsubstituted except for hydrogen.
Claim 2
Dependent Claim
77 words
A process for making benzyl substituted phenols, said process comprising contacting a mixture of a phenol and a benzyl alcohol in the vapor phase with an activated gamma alumina catalyst at a temperature in the range of 225°-450° C., said temperature being high enough to maintain said phenol and benzyl alcohol in the vapor phase at reaction conditions, said phenol having at least one position ortho or para to its phenolic hydroxyl group unsubstituted except for hydrogen.
Claim 3
Dependent Claim
19 words
A process of claim 1 wherein the mole ratio of said benzyl alcohol to said phenol is about 1-3:1.
Claim 4
Dependent Claim
12 words
A process of claim 2 wherein said temperature is about 250°-350° C.
Claim 5
Dependent Claim
52 words
A process of claim 1 wherein said phenol has the structure ##STR2## wherein R 1 and R 2 are selected from the group consisting of hydrogen, alkyl containing 1-20 carbon atoms, alkenyl containing 2-20 carbon atoms, cycloalkyl containing 5-8 carbon atoms, aryl containing 6-12 carbon atoms, halogen, hydroxy and C 1-4 alkoxy.
Claim 6
Dependent Claim
79 words
A process for selectively di-orthobenzylating a phenol which is unsubstituted except for hydrogen in both positions ortho to its phenolic hydroxyl group, said process comprising contacting a mixture of said phenol and said benzyl alcohol in the mole ratio of about 1:1-3 in the vapor phase with a gamma-alumina catalyst at a temperature in the range of about 225°-450° C., said temperature being high enough to maintain said phenol and benzyl alcohol in the vapor phase under reaction conditions.
Claim 7
Dependent Claim
79 words
A process for selectively di-orthobenzylating a phenol which is unsubstituted except for hydrogen in both positions ortho to its phenolic hydroxyl group, said process comprising contacting a mixture of said phenol and said benzyl alcohol in the mole ratio of about 1:1-3 in the vapor phase with a gamma-alumina catalyst at a temperature in the range of about 225°-450° C., said temperature being high enough to maintain said phenol and benzyl alcohol in the vapor phase under reaction conditions.
Claim 8
Dependent Claim
25 words
A process of claim 5 wherein said phenol is the compound phenol and further comprising the step of recovering therefrom as the major product 2,6-dibenzylphenol.
Claim 9
Dependent Claim
27 words
A process of claim 6 wherein the mole ratio of said benzyl alcohol to said phenol is about 1-3:1 and said temperature range is about 250°-350° C.
Claim 10
Dependent Claim
12 words
A process of claim 7 wherein said mole ratio is about 1.5-2.5:1.
Claim 11
Dependent Claim
39 words
Organic material normally susceptible to gradual degradation due to the effects of oxygen containing an antioxidant amount of a compound selected from the group consisting of 2,6-dibenzyl phenol and 2,6-dibenzyl-4-alkyl phenol wherein said alkyl contains about 1-12 carbon atoms.
Claim 12
Dependent Claim
39 words
Organic material normally susceptible to gradual degradation due to the effects of oxygen containing an antioxidant amount of a compound selected from the group consisting of 2,6-dibenzyl phenol and 2,6-dibenzyl-4-alkyl phenol wherein said alkyl contains about 1-12 carbon atoms.
Claim 13
Dependent Claim
12 words
An organic composition of claim 9 wherein said compound is a 2,6-dibenzyl-4-alkylphenol.
Claim 14
Dependent Claim
11 words
An organic composition of claim 10 wherein said compound is 2,6-dibenzyl-4-methylphenol.
References Cited (Backward Citations)
US4105698A
Cited
US4105699A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1988-04-29 | 1988-10-29 | 1989-04-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-04-29 | 1992-10-29 | 1993-04-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-04-29 | 1996-10-29 | 1997-04-30 | $7700.00 | Window Closed / Lapsed |