US3946086A
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Method of producing 2,6-dialkyl- and 2,6-diaralkyl-substituted derivatives of p-cresol
Assignee: Individual
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Filing: 1970-10-28
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Granted: 1976-03-23
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Expires: 1990-10-28
Abstract
Abstract A method of producing 2,6-dialkyl- and 2,6-diaralkyl-substituted derivatives of p-cresol of the general formula ##SPC1## Wherein R signifies an alkyl group having from 4 to 12 carbon atoms or ##SPC2## Comprising subjecting phenol to alkylation with olefines having from 4 to 12 carbon atoms or with styrene at a temperature of 50°-150°C in the presence of a catalyst, namely, aluminum, taken in an amount of 0.1-5 wt.% of phenol. 2,6-Dialkyl phenol or 2,6-diaralkyl phenol resulting after from the alkylation is treated with a mixture of formaldehyde and dimethylamine or with a product of their interaction having the formula ##EQU1## at a temperature of 20°-100°C with subsequent catalytic hydrogenolysis of N,N-dimethyl(3,5-dialkyl-4-hydroxybenzyl)/amine or N,N-dimethyl(3,5-diaralkyl-4-hydroxybenzyl/amine at a temperature of 80°-200°C., molar ratio of hydrogen to the product being treated of 1-5:1 and space velocity of 0.1-2 hour.sup. -1 . The products produced by said method feature a high degree of purity, and they can be employed as effective inhibitors of thermooxidation degradation of polymers and hydrocarbon fuels, and also as intermediates for producing p-cresol, and 2-alkyl- and 2-aralkyl-substituted derivatives of p-cresol.
Inventors
- 👤 Felix Borisovich Gershanov
- 👤 Alexandr Grigorievich Liakumovich
- 👤 Jury Ivanovich Michurov
- 👤 Boris Izrailevich Pantukh
- 👤 Grigory Iosifovich Rutman
- 👤 Valerian Mikhailovich Sobolev
- 👤 Alexandr Afroimovich Grinberg
- 👤 Yakov Abramovich Gurvich
- 👤 Nina Vasilievna Zakharova
- 👤 Almira Mudarisovna Nafikova
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 05:00
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/50; C07C37/11; C07C37/14; C08; C08K; C08K5/00; C08K5/04; C08K5/13; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/221
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
139 words
A method of producing a 2,6-dialkyl-p-cresol of the formula ##SPC5## wherein R signifies an alkyl radical having from 4 to 12 carbon atoms comprising alkylating phenol with an olefin having from 4 to 12 carbon atoms at a temperature of 50°-150°C. in the presence of aluminum as a catalyst in an amount of 0.1-5% by weight of the phenol to form an alkylated phenol, treating said alkylated phenol with a reactant selected from the group consisting of (a) a mixture of formaldehyde and dimethylamine and (b) their interaction product having the formula ##EQU3## at a temperature of 20°-100°C. to form an intermediate product, N,N-dimethyl-3,5-dialkyl-4-hydroxy benzylamine, and subjecting said intermediate product to catalytic hydrogenolysis at 80°-200°C. using a molar ratio of hydrogen to said intermediate product of 1-5:1 and a space velocity of 0.1-2 hour.sup. -1 to form the 2,6-dialkyl-p-cresol.
Claim 2
Independent Claim
139 words
A method of producing a 2,6-dialkyl-p-cresol of the formula ##SPC5## wherein R signifies an alkyl radical having from 4 to 12 carbon atoms comprising alkylating phenol with an olefin having from 4 to 12 carbon atoms at a temperature of 50°-150°C. in the presence of aluminum as a catalyst in an amount of 0.1-5% by weight of the phenol to form an alkylated phenol, treating said alkylated phenol with a reactant selected from the group consisting of (a) a mixture of formaldehyde and dimethylamine and (b) their interaction product having the formula ##EQU3## at a temperature of 20°-100°C. to form an intermediate product, N,N-dimethyl-3,5-dialkyl-4-hydroxy benzylamine, and subjecting said intermediate product to catalytic hydrogenolysis at 80°-200°C. using a molar ratio of hydrogen to said intermediate product of 1-5:1 and a space velocity of 0.1-2 hour.sup. -1 to form the 2,6-dialkyl-p-cresol.
Claim 3
Dependent Claim
19 words
A method as claimed in claim 1, wherein alkylation is carried out at a pressure of 2-50 abs. atm.
Claim 4
Dependent Claim
19 words
A method as claimed in claim 2, wherein alkylation is carried out at a pressure of 3-15 abs. atm.
Claim 5
Independent Claim
101 words
A method of producing a 2,6-dialkyl-p-cresol of the formula ##SPC6## wherein R signifies an alkyl radical having from 4 to 12 carbon atoms comprising (1) reacting the corresponding 2,6-dialkyl phenol with a reagent selected from the group consisting of (a) a mixture of formaldehyde and dimethyl-amine and (b) their interaction product having the formula ##EQU4## at a temperature of 20°-100°C. to form an intermediate product N,N-dimethyl-3,5-dialkyl-4-hydroxybenzylamine and (2) subjecting said intermediate product to catalytic hydrogenolysis at 80°-200°C. using a molar ratio of hydrogen to said intermediate product of 1-5:1 and a space velocity of 0.1-2 hour.sup. -1 to form the 2,6-dialkyl-p-cresol.
Claim 6
Independent Claim
101 words
A method of producing a 2,6-dialkyl-p-cresol of the formula ##SPC6## wherein R signifies an alkyl radical having from 4 to 12 carbon atoms comprising (1) reacting the corresponding 2,6-dialkyl phenol with a reagent selected from the group consisting of (a) a mixture of formaldehyde and dimethyl-amine and (b) their interaction product having the formula ##EQU4## at a temperature of 20°-100°C. to form an intermediate product N,N-dimethyl-3,5-dialkyl-4-hydroxybenzylamine and (2) subjecting said intermediate product to catalytic hydrogenolysis at 80°-200°C. using a molar ratio of hydrogen to said intermediate product of 1-5:1 and a space velocity of 0.1-2 hour.sup. -1 to form the 2,6-dialkyl-p-cresol.
Claim 7
Dependent Claim
28 words
A method as claimed in claim 4, wherein the treatment of 2,6-dialkyl phenol with the mixture of formaldehyde and dimethyl-amine is carried out at a temperature of 50°-80°C.
Claim 8
Dependent Claim
30 words
A method as claimed in claim 4, wherein the treatment of 2,6-dialkyl phenol with the product of interaction of formaldehyde with dimethylamine is carried out at a temperature of 50°-80°C.
Claim 9
Dependent Claim
30 words
A method as claimed in claim 4, wherein the treatment of 2,6-dialkyl phenol with the mixture of formaldehyde and dimethylamine is carried out in the medium of saturated aliphatic alcohol.
Claim 10
Dependent Claim
18 words
A method as claimed in claim 7, wherein the monobasic aliphatic alcohol has 1 to 4 carbon atoms.
Claim 11
Dependent Claim
33 words
A method as claimed in claim 4, wherein the treatment of 2,6-dialkyl phenol with the product of interaction of formaldehyde with dimethylamine is carried out in the medium of a saturated aliphatic alcohol.
Claim 12
Dependent Claim
18 words
A method as claimed in claim 9, wherein the monobasic aliphatic alcohol has 1 to 4 carbon atoms.
Claim 13
Independent Claim
55 words
A method of producing a 2,6-dialkyl-p-cresol which comprises subjecting a N,N-dimethyl-3,5-dialkyl-4-hydroxybenzylamine of the formula ##SPC7## wherein R signifies an alkyl radical having 4 to 12 carbon atoms to catalytic hydrogenolysis at 80°-200°C. using a molar ratio of hydrogen to said N,N-dimethyl-3,5-dialkyl-4-hydroxybenzylamine of 1-5:1 and a space velocity of 0.1-2 hour.sup. -1 to form the 2,6-dialkyl-p-cresol.
Claim 14
Independent Claim
55 words
A method of producing a 2,6-dialkyl-p-cresol which comprises subjecting a N,N-dimethyl-3,5-dialkyl-4-hydroxybenzylamine of the formula ##SPC7## wherein R signifies an alkyl radical having 4 to 12 carbon atoms to catalytic hydrogenolysis at 80°-200°C. using a molar ratio of hydrogen to said N,N-dimethyl-3,5-dialkyl-4-hydroxybenzylamine of 1-5:1 and a space velocity of 0.1-2 hour.sup. -1 to form the 2,6-dialkyl-p-cresol.
Claim 15
Dependent Claim
16 words
A method as claimed in claim 11, wherein hydrogenolysis is effected at a temperature of 120°-140°C.
Claim 16
Dependent Claim
16 words
A method as claimed in claim 11, wherein nickel-chromium catalyst is used as a hydrogenolysis catalyst.
Claim 17
Dependent Claim
16 words
A method as claimed in claim 11, wherein nickel-copper catalyst is used as a hydrogenolysis catalyst.
Claim 18
Dependent Claim
31 words
A method as claimed in claim 11, wherein alloyed nickel-aluminum-titanium catalyst comprising 20-60 wt.% of nickel, 20-40 wt.% of aluminum and 1-10 wt.% of titanium is used as a hydrogenolysis catalyst.
Claim 19
Dependent Claim
20 words
A method as claimed in claim 11, wherein hydrogenolysis is carried out in the medium of a non-polar organic solvent.
Claim 20
Dependent Claim
21 words
A method as claimed in claim 16, wherein the non-polar solvent is a hydrocarbon having from 5 to 20 carbon atoms.
Claim 21
Dependent Claim
21 words
A method as claimed in claim 16, wherein the non-polar solvent is a cycloparaffin hydrocarbon having 5 to 20 carbon atoms.
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) | 1979-03-23 | 1979-09-22 | 1980-03-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-23 | 1983-09-22 | 1984-03-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-23 | 1987-09-22 | 1988-03-23 | $7700.00 | Window Closed / Lapsed |