US4190601A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Production of tertiary amines by reductive alkylation
Assignee: Union Carbide Corp
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Filing: 1978-05-31
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Granted: 1980-02-26
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Expires: 1998-05-31
Abstract
Abstract A process for the reductive alkylation of secondary amines with either aliphatic aldehydes or aliphatic ketones in contact with hydrogen, a water-segregating agent and a hydrogenation catalyst to form tertiary amines.
Inventors
- 👤 Quintin W. Decker
- 👤 Erich Marcus
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 14:25
CPC Classifications
C; C07; C07C; C07C213/00; C07C213/06; C07C209/00; C07C209/24; C07C209/26; C07C213/08
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
194 words
A process for the production of tertiary amines of the formula ##STR2## which comprises the reductive alkylation at from 20° C. to 200° C. of (I) a secondary amine of the formula ##STR3## with (II) a member from the group of the aliphatic aldehydes and the aliphatic ketones of the formula ##STR4## where R and R' can be: (a) alkyl, substituted or unsubstituted, linear or branched, having from one to twenty carbon atoms; or (b) a substituted or unsubstituted cycloalkyl having from four to eight ring carbon atoms; or (c) a substituted or unsubstituted hydroxyalkyl, linear or branched, having from one to twenty carbon atoms; or (d) a substituted or unsubstituted aralkyl having from seven to twenty carbon atoms; or (e) hydrogen; and R" and R'" singly can be: (a) alkyl, substituted or unsubstituted, linear or branched, having from one to twenty carbon atoms; or (b) hydrogen; or (c) when taken together they can be alkylene having from three to six carbon atoms forming a cyclic ketone, in contact with hydrogen at a superatmospheric pressure, a water-segregating agent and a catalytically effective amount, sufficient to carry out the reductive alkylation, of a hydrogenation catalyst.
Claim 2
Dependent Claim
194 words
A process for the production of tertiary amines of the formula ##STR2## which comprises the reductive alkylation at from 20° C. to 200° C. of (I) a secondary amine of the formula ##STR3## with (II) a member from the group of the aliphatic aldehydes and the aliphatic ketones of the formula ##STR4## where R and R' can be: (a) alkyl, substituted or unsubstituted, linear or branched, having from one to twenty carbon atoms; or (b) a substituted or unsubstituted cycloalkyl having from four to eight ring carbon atoms; or (c) a substituted or unsubstituted hydroxyalkyl, linear or branched, having from one to twenty carbon atoms; or (d) a substituted or unsubstituted aralkyl having from seven to twenty carbon atoms; or (e) hydrogen; and R" and R'" singly can be: (a) alkyl, substituted or unsubstituted, linear or branched, having from one to twenty carbon atoms; or (b) hydrogen; or (c) when taken together they can be alkylene having from three to six carbon atoms forming a cyclic ketone, in contact with hydrogen at a superatmospheric pressure, a water-segregating agent and a catalytically effective amount, sufficient to carry out the reductive alkylation, of a hydrogenation catalyst.
Claim 3
Dependent Claim
27 words
A process as claimed in claim 1 wherein said water-segregating agent is a zeolitic molecular sieve having a pore diameter of from 2.5 to 5 Angstrom units.
Claim 4
Dependent Claim
17 words
A process as claimed in claim 2 wherein said molecular sieve is a Type A molecular sieve.
Claim 5
Dependent Claim
14 words
A process as claimed in claim 1 wherein said water-segregating agent is calcium chloride.
Claim 6
Dependent Claim
14 words
A process as claimed in claim 1 wherein said water-segregating agent is magnesium sulfate.
Claim 7
Dependent Claim
14 words
A process as claimed in claim 1 wherein said water-segregating agent is calcium sulfate.
Claim 8
Dependent Claim
14 words
A process as claimed in claim 1 wherein said water-segregating agent is sodium sulfate.
Claim 9
Dependent Claim
14 words
A process as claimed in claim 1 wherein said hydrogenation catalyst is Raney nickel.
Claim 10
Dependent Claim
23 words
A process as claimed in claim 1 wherein the reaction is carried out at a temperature of from 70° C. to 120° C.
Claim 11
Dependent Claim
23 words
A process as claimed in claim 1 wherein the reaction is carried out at a pressure of from 50 psig to 3000 psig.
Claim 12
Dependent Claim
40 words
A process as claimed in claim 1 wherein said catalyst is present at a concentration of from 0.5 weight percent to 10 weight percent based on the total weight of the aldehyde or ketone, secondary amine, and water-segregating agent charged.
Claim 13
Dependent Claim
22 words
A process as claimed in claim 1 wherein the mole ratio of component (II) to component (I) is from 2 to 10:1.
Claim 14
Dependent Claim
22 words
A process as claimed in claim 1 wherein the mole ratio of component (II) to component (I) is from 5 to 10:1.
Claim 15
Dependent Claim
22 words
A process as claimed in claim 1 wherein the mole ratio of component (II) to component (I) is from 6 to 8:1.
Claim 16
Dependent Claim
37 words
A process as claimed in claim 1 wherein the concentration of said water-segregating agent ranges from 0.1 weight percent to 20 weight percent based on the total weight of aldehyde or ketone, secondary amine, and catalyst charged.
References Cited (Backward Citations)
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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) | 1983-02-25 | 1983-08-27 | 1984-02-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-02-25 | 1987-08-27 | 1988-02-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-02-25 | 1991-08-27 | 1992-02-26 | $7700.00 | Window Closed / Lapsed |