US4595773A
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US
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Method for preparing copper-diamine complexes and diamines
Assignee: General Electric Co
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Filing: 1985-01-24
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Granted: 1986-06-17
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Expires: 2005-01-24
Abstract
Abstract Copper-diamine complexes such as copper(II)-di-t-butylethylenediamine dibromide are prepared by the reaction of a dihalide such as 1,2-dibromoethane with an amine such as t-butylamine and a basic copper(II) compound such as cupric oxide in a nitrile solvent. The diamine can be liberated from the complex by reacting it with a complexing agent such as an ethylenediaminetetraacetic acid salt.
Inventors
- 👤 Dwain M. White
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 23:37
CPC Classifications
C; C07; C07F; C07F1/00; C07F1/005; C07C; C07C209/00; C07C209/04; C07C209/06; C07C209/08
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
156 words
A method for preparing a copper-diamine complex having the formula ##STR3## wherein: R 1 is an ethylene, trimethylene or C 5-6 1,2- or 1,3-cycloalkylene radical which, if substituted, contains only phenyl substituents or tertiary alkyl substituents containing about 4-8 carbon atoms; R 2 is an alkyl radical containing up to about 8 carbon atoms or a phenyl radical; R 3 is hydrogen, an alkyl radical containing up to about 8 carbon atoms or a phenyl radical; and X is chlorine, bromine or iodine; said method comprising reacting, at a temperature in the range of about 50°-120° C., a dihalide of the formula R 1 X 2 with an amine of the formula R 2 NHR 3 and at least one basic copper(II) compound in at least one aliphatic or aromatic nitrile as diluent; about 2.1-2.5 moles of amine and an amount of basic copper compound containing 1 gram-atom of copper being used per mole of dihalide.
Claim 2
Independent Claim
156 words
A method for preparing a copper-diamine complex having the formula ##STR3## wherein: R 1 is an ethylene, trimethylene or C 5-6 1,2- or 1,3-cycloalkylene radical which, if substituted, contains only phenyl substituents or tertiary alkyl substituents containing about 4-8 carbon atoms; R 2 is an alkyl radical containing up to about 8 carbon atoms or a phenyl radical; R 3 is hydrogen, an alkyl radical containing up to about 8 carbon atoms or a phenyl radical; and X is chlorine, bromine or iodine; said method comprising reacting, at a temperature in the range of about 50°-120° C., a dihalide of the formula R 1 X 2 with an amine of the formula R 2 NHR 3 and at least one basic copper(II) compound in at least one aliphatic or aromatic nitrile as diluent; about 2.1-2.5 moles of amine and an amount of basic copper compound containing 1 gram-atom of copper being used per mole of dihalide.
Claim 3
Dependent Claim
11 words
A method according to claim 1 wherein the nitrile is acetonitrile.
Claim 4
Dependent Claim
14 words
A method according to claim 2 wherein the basic copper(II) compound is cupric oxide.
Claim 5
Dependent Claim
10 words
A method according to claim 3 wherein X is bromine.
Claim 6
Dependent Claim
13 words
A method according to claim 4 wherein R 1 is the ethylene radical.
Claim 7
Dependent Claim
18 words
A method according to claim 5 wherein R 2 is t-butyl or phenyl and R 3 is hydrogen.
Claim 8
Dependent Claim
11 words
A method according to claim 6 wherein R 2 is t-butyl.
Claim 9
Dependent Claim
21 words
A method according to claim 6 wherein the reaction is conducted at a temperature within the range of about 50°-120° C.
Claim 10
Dependent Claim
11 words
A method according to claim 8 wherein R 2 is t-butyl.
Claim 11
Dependent Claim
109 words
A mixture comprising a dihalide of the formula R 1 X 2 , an amine of the formula R 2 NHR 3 , at least one basic copper(II) compound and at least one aliphatic or aromatic nitrile; wherein: R 1 is an ethylene, trimethylene or C 5-6 1,2- or 1,3-cycloalkylene radical which, if substituted, contains only phenyl substituents or tertiary alkyl substituents containing about 4-8 carbon atoms; R 2 is an alkyl radical containing up to about 8 carbon atoms or a phenyl radical; R 3 is hydrogen, an alkyl radical containing up to about 8 carbon atoms or a phenyl radical; and X is chlorine, bromine or iodine.
Claim 12
Dependent Claim
109 words
A mixture comprising a dihalide of the formula R 1 X 2 , an amine of the formula R 2 NHR 3 , at least one basic copper(II) compound and at least one aliphatic or aromatic nitrile; wherein: R 1 is an ethylene, trimethylene or C 5-6 1,2- or 1,3-cycloalkylene radical which, if substituted, contains only phenyl substituents or tertiary alkyl substituents containing about 4-8 carbon atoms; R 2 is an alkyl radical containing up to about 8 carbon atoms or a phenyl radical; R 3 is hydrogen, an alkyl radical containing up to about 8 carbon atoms or a phenyl radical; and X is chlorine, bromine or iodine.
Claim 13
Dependent Claim
19 words
A composition according to claim 10 wherein the basic copper(II) compound is cupric oxide and the nitrile is acetonitrile.
Claim 14
Dependent Claim
10 words
A composition according to claim 11 wherein X is bromine.
Claim 15
Dependent Claim
13 words
A composition according to claim 12 wherein R 1 is the ethylene radical.
Claim 16
Dependent Claim
16 words
A composition according to claim 13 wherein R 2 is t-butyl and R 3 is hydrogen.
Claim 17
Independent Claim
118 words
A method for preparing a diamine of the formula ##STR4## wherein: R 1 is an ethylene, trimethylene or C 5-6 1,2- or 1,3-cycloalkylene radical which, if substituted, contains only phenyl substituents or tertiary alkyl substituents containing about 4-8 carbon atoms; R 2 is an alkyl radical containing up to about 8 carbon atoms or a phenyl radical; and R 3 is hydrogen, an alkyl radical containing up to about 8 carbon atoms or a phenyl radical; which comprises reacting a copper-diamine complex of the formula ##STR5## wherein X is chlorine, bromine, or iodine, with a complexing agent selected from the group consisting of ammonium ion, cyanide ion, ethylenediaminetetraacetic acid and its salts and nitrilotriacetic acid and its salts.
Claim 18
Independent Claim
118 words
A method for preparing a diamine of the formula ##STR4## wherein: R 1 is an ethylene, trimethylene or C 5-6 1,2- or 1,3-cycloalkylene radical which, if substituted, contains only phenyl substituents or tertiary alkyl substituents containing about 4-8 carbon atoms; R 2 is an alkyl radical containing up to about 8 carbon atoms or a phenyl radical; and R 3 is hydrogen, an alkyl radical containing up to about 8 carbon atoms or a phenyl radical; which comprises reacting a copper-diamine complex of the formula ##STR5## wherein X is chlorine, bromine, or iodine, with a complexing agent selected from the group consisting of ammonium ion, cyanide ion, ethylenediaminetetraacetic acid and its salts and nitrilotriacetic acid and its salts.
Claim 19
Dependent Claim
17 words
A method according to claim 15 wherein X is bromine and R 1 is the ethylene radical.
Claim 20
Dependent Claim
16 words
A method according to claim 16 wherein the complexing agent is a salt of ethylenediaminetetraacetic acid.
Claim 21
Dependent Claim
16 words
A method according to claim 17 wherein R 2 is t-butyl and R 3 is hydrogen.
Claim 22
Dependent Claim
13 words
A method according to claim 18 wherein the complexing agent is trisodium ethylenediaminetetraacetate.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-06-16 | 1989-12-16 | 1990-06-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-06-16 | 1993-12-16 | 1994-06-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-06-16 | 1997-12-16 | 1998-06-17 | $7700.00 | Window Closed / Lapsed |