US4760185A
Expired / Lapsed
US
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Process for the ortho-alkylation of optionally alkyl-substituted m-phenylenediamines
Assignee: Bayer AG
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Filing: 1986-05-06
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Granted: 1988-07-26
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Expires: 2006-05-06
Abstract
Abstract m-Phenylenediamines are alkylated in the orthoposition by heating them with an Al/Zn alloy and aluminium chloride, and reacting them with lower alkenes at elevated pressures and temperatures when the evolution of hydrogen is complete.
Inventors
- 👤 Hans-Joachim Becker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 18:33
CPC Classifications
C; C07; C07C; C07C209/00; C07C209/68
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
143 words
A process for the ortho-alkylation of m-phenylenediamine or a m-phenylenediamine which contains one or more alkyl, cycloalkyl or aralkyl groups having 1 to 8 carbon atoms which comprises heating said m-phenylenediamine in the presence of an aluminum/zinc alloy, said aluminum/zinc alloy having a zinc content of 2 to 30% by weight and an aluminum content of 70 to 98% by weight, said aluminum/zinc alloy being employed in an amount of 0.5 to 4.0% by weight, based upon the weight of the m-phenylenediamine, and aluminum chloride, said aluminum chloride being employed in an amount of 1.0 to 7.0% by weight, based on the weight of the m-phenylenediamine, and contacting the so heated m-phenylenediamine with a lower alkene at a pressure of 50 to 250 bar and at a temperature of 250° to 330° C. when evolution of hydrogen from the heated m-phenylenediamine is complete.
Claim 2
Dependent Claim
143 words
A process for the ortho-alkylation of m-phenylenediamine or a m-phenylenediamine which contains one or more alkyl, cycloalkyl or aralkyl groups having 1 to 8 carbon atoms which comprises heating said m-phenylenediamine in the presence of an aluminum/zinc alloy, said aluminum/zinc alloy having a zinc content of 2 to 30% by weight and an aluminum content of 70 to 98% by weight, said aluminum/zinc alloy being employed in an amount of 0.5 to 4.0% by weight, based upon the weight of the m-phenylenediamine, and aluminum chloride, said aluminum chloride being employed in an amount of 1.0 to 7.0% by weight, based on the weight of the m-phenylenediamine, and contacting the so heated m-phenylenediamine with a lower alkene at a pressure of 50 to 250 bar and at a temperature of 250° to 330° C. when evolution of hydrogen from the heated m-phenylenediamine is complete.
Claim 3
Dependent Claim
30 words
A process according to claim 1 wherein the aluminum/zinc alloy has a zinc content of 5 to 20% by weight and an aluminum content of 80 to 95% by weight.
Claim 4
Dependent Claim
25 words
A process according to claim 1 wherein said m-phenylenediamine is selected from the group consisting of m-phenylenediamine, 2,4-toluylenediamine, 2,6-toluylenediamine, 1-ethyl-2,4-phenylenediamine, 1-ethyl-2,6-phenylenediamine, 1-propyl-2,4-phenylenediamine, 1,3-dimethyl-4,6-phenylenediamine and 1-benzyl-2,4-phenylenediamine.
Claim 5
Dependent Claim
71 words
A process according to claim 3 wherein the aluminum/zinc alloy has a zinc content of 2 to 30% and an aluminum content of 70 to 98% by weight, the aluminum/zinc alloy is employed in an amount of 0.5 to 4.0% by weight, based upon the weight of the m-phenylenediamine and the aluminum chloride is employed in an amount of 1.0 to 7.0% by weight, based upon the weight of the m-phenylenediamine.
Claim 6
Dependent Claim
31 words
A process according to claim 4 wherein the reaction with the alkene is carried out under a pressure of 50 to 250 bar at a temperature of 250° to 330° C.
Claim 7
Dependent Claim
13 words
A process according to claim 5 wherein the alkene is ethylene or propylene.
Claim 8
Dependent Claim
24 words
A process according to claim 1, wherein said m-phenylenediamine contains one or more alkyl, cycloalkyl or aralkyl groups having 1 to 3 carbon atoms.
Claim 9
Dependent Claim
28 words
A process according to claim 1, wherein said aluminum/zinc alloy is employed in an amount of 1 to 2% by weight, based upon the weight of the m-phenylenediamine.
Claim 10
Dependent Claim
28 words
A process according to claim 1, wherein the aluminum chloride is present in an amount of 2.5 to 4% by weight, based on the weight of the m-phenylenediamine.
Claim 11
Dependent Claim
32 words
A process according to claim 1, wherein the temperature of the heating of the m-phenylenediamine in the presence of the aluminum/zinc alloy and the aluminum chloride is 150° C. to 250° C.
Claim 12
Dependent Claim
32 words
A process according to claim 1, wherein the temperature of the heating of the m-phenylenediamine in the presence of the aluminum/zinc alloy and the aluminum chloride is 170° C. to 220° C.
Claim 13
Dependent Claim
24 words
A process according to claim 1, wherein the reaction of the alkene is carried out at a temperature of 280° C. to 310° C.
Claim 14
Dependent Claim
23 words
A process according to claim 1, wherein the reaction of the alkene is carried our under a pressure of 80 to 120 bar.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-07-26 | 1992-01-25 | 1992-07-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-07-26 | 1996-01-25 | 1996-07-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-07-26 | 2000-01-25 | 2000-07-26 | $7700.00 | Window Closed / Lapsed |