US5298618A
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Macrocyclic oxamides
Assignee: Huntsman Corp
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Filing: 1992-11-23
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Granted: 1994-03-29
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Expires: 2012-11-23
Abstract
Abstract Macrocyclic oxamides may be made easily, in good yield and in one step by reacting an oxalic compound, such as oxalic acid or oxalic esters, with a diamine, where the amine groups are separated by at least five atoms. The oxalic compounds may include, but are not limited to such materials as dimethyl oxalate and diethyl oxalate. The diamines may include, but are not limited to such materials as alkylenediamines; polyalkylene glycol diamines; alkyl-bis-(aminoalkyl)amines; imino bis-(alkyl)amines; and N,N' bis-(aminoalkyl)-N,N'-dialkylalkylenediamines and bis-(aminoalkyl)piperazines; and mixtures thereof. The macrocyclic oxamides made by this process may be used to selectively separate metal ions from solution, or complexed together with a metal ion act as a catalyst.
Inventors
- 👤 George P. Speranza
- 👤 Donald H. Champion
- 👤 Martin J. Plishka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 12:58
CPC Classifications
C; C07; C07D; C07D245/00; C07D245/02; C22; C22B; C22B3/00; C22B3/20; C22B3/26; C22B3/36; C22B3/362; C07D255/00; C07D255/02; C07D257/00; C07D257/02; C07D259/00; C07D273/00; Y; Y02; Y02P; Y02P10/00; Y02P10/20
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
83 words
Macrocyclic oxamides made by the reaction of an oxalic compound selected from the group consisting of oxalic acid and oxalic esters, with a diamine of the formula: H.sub.2 N--R--NH.sub.2 where R is selected from the group consisting of: ##STR8## where R 1 is independently C 2 -C 4 straight or branched alkylene; R 2 is independently H and C 1 -C 4 straight or branched alkyl; R 3 is independently C 2 -C 4 straight or branched alkylene; and z averages about 1-5.
Claim 2
Dependent Claim
83 words
Macrocyclic oxamides made by the reaction of an oxalic compound selected from the group consisting of oxalic acid and oxalic esters, with a diamine of the formula: H.sub.2 N--R--NH.sub.2 where R is selected from the group consisting of: ##STR8## where R 1 is independently C 2 -C 4 straight or branched alkylene; R 2 is independently H and C 1 -C 4 straight or branched alkyl; R 3 is independently C 2 -C 4 straight or branched alkylene; and z averages about 1-5.
Claim 3
Dependent Claim
35 words
The macrocyclic oxamides of claim 1 where the oxalic compound has the formula: ##STR9## where R 4 is selected from the group consisting of hydrogen and C 1 -C 12 straight or branched alkyl groups.
Claim 4
Dependent Claim
28 words
The macrocyclic oxamides of claim 1 where the oxalic compound is selected from the group consisting of dimethyl oxalate, diethyl oxalate, dipropyl oxalate, dibutyl oxalate and mixtures thereof.
Claim 5
Dependent Claim
40 words
Macrocyclic oxamides made by the reaction of an oxalic compound selected from the group consisting of oxalic acid and oxalic esters, with a diamine where the diamine is selected from the group consisting of alkyl-bis-(aminoalkyl)amines; imino-bis-alkylamines; and N,N'-bis-(aminoalkyl)-N,N'-dialkylalkylenediamines and bis-(aminoalkyl)piperazines.
Claim 6
Dependent Claim
40 words
Macrocyclic oxamides made by the reaction of an oxalic compound selected from the group consisting of oxalic acid and oxalic esters, with a diamine where the diamine is selected from the group consisting of alkyl-bis-(aminoalkyl)amines; imino-bis-alkylamines; and N,N'-bis-(aminoalkyl)-N,N'-dialkylalkylenediamines and bis-(aminoalkyl)piperazines.
Claim 7
Dependent Claim
50 words
The macrocyclic oxamides of claim 1 where the reaction is carried out at a temperature between about 20° and 200° C., at a pressure between subatmospheric and about 10 atm, and in a solvent selected from the group consisting of isopropanol, methanol, ethanol, 2-ethylhexanol, butanol, glycol ethers, diglyme and triglyme.
Claim 8
Dependent Claim
66 words
Macrocyclic oxamides having the formula: ##STR10## where x is 1 or 2; R is independently selected from the group consisting of: ##STR11## where R 1 is independently C 2 -C 4 straight or branched alkylene; R 2 is independently H and C 1 -C 4 straight or branched alkyl; R 3 is independently C 2 -C 4 straight or branched alkylene; and z averages about 1-5.
Claim 9
Dependent Claim
66 words
Macrocyclic oxamides having the formula: ##STR10## where x is 1 or 2; R is independently selected from the group consisting of: ##STR11## where R 1 is independently C 2 -C 4 straight or branched alkylene; R 2 is independently H and C 1 -C 4 straight or branched alkyl; R 3 is independently C 2 -C 4 straight or branched alkylene; and z averages about 1-5.
Claim 10
Dependent Claim
61 words
Macrocyclic oxamides having the formula: ##STR12## where R is independently selected from the group consisting of: ##STR13## where R 1 is independently C 2 -C 4 straight or branched alkylene; R 2 is independently H and C 1 -C 4 straight or branched alkyl; R 3 is independently C 2 -C 4 straight or branched alkylene; and z averages about 1-5.
Claim 11
Dependent Claim
61 words
Macrocyclic oxamides having the formula: ##STR12## where R is independently selected from the group consisting of: ##STR13## where R 1 is independently C 2 -C 4 straight or branched alkylene; R 2 is independently H and C 1 -C 4 straight or branched alkyl; R 3 is independently C 2 -C 4 straight or branched alkylene; and z averages about 1-5.
References Cited (Backward Citations)
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| 3.5 Years (Year 4) | 1997-03-28 | 1997-09-27 | 1998-03-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-03-28 | 2001-09-27 | 2002-03-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-03-28 | 2005-09-27 | 2006-03-29 | $7700.00 | Window Closed / Lapsed |