Patent US4922024A successfully refreshed from Google Patents.
US4922024A
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Amination process employing group vib metal catalysts
Assignee: Dow Chemical Co
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Filing: 1988-04-14
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Granted: 1990-05-01
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Expires: 2008-04-14
Abstract
Abstract A process for preparing amines comprising contacting an alcohol with a reactant amine in the presence of hydrogen and a catalyst comprising at least one compound containing an element of Group VIB and at least one non-metallic element of Groups IIIA, IVA, and VA of the Periodic Table, the contacting occurring under conditions such that the hydroxyl moiety of the alcohol is replaced by the reactant amine to form an amine product.
Inventors
- 👤 Robert G. Bowman
- 👤 Marvin H. Tegen
- 👤 George E. Hartwell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 18:02
CPC Classifications
C; C07; C07C; C07C209/00; C07C209/04; C07C209/14; C07C209/16
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
141 words
A process for preparing an amine comprising contacting an alcohol with a reactant amine in the presence of hydrogen and a catalyst selected from the group consisting of: (1) Binary compounds consisting essentially of an element of Group VIB and a non-metallic element selected form Groups IIIA, IVA, or VA; (2) Ternary compounds consisting essentially of an element of Group VIB and two non-metallic elements selected from Groups IIIA, IVA, and VA; and (3) Ternary compounds consisting essentially of an element of Group VIB, oxygen, and one non-metallic element selected from Groups IIIA, IVA, or VA, such that the oxygen content of the compound is less than about 10 mole percent of the total moles of non-metals, the contacting occurring under conditions such that a hydroxyl moiety of the alcohol is replaced by the reactant amine to form an amine product.
Claim 2
Dependent Claim
141 words
A process for preparing an amine comprising contacting an alcohol with a reactant amine in the presence of hydrogen and a catalyst selected from the group consisting of: (1) Binary compounds consisting essentially of an element of Group VIB and a non-metallic element selected form Groups IIIA, IVA, or VA; (2) Ternary compounds consisting essentially of an element of Group VIB and two non-metallic elements selected from Groups IIIA, IVA, and VA; and (3) Ternary compounds consisting essentially of an element of Group VIB, oxygen, and one non-metallic element selected from Groups IIIA, IVA, or VA, such that the oxygen content of the compound is less than about 10 mole percent of the total moles of non-metals, the contacting occurring under conditions such that a hydroxyl moiety of the alcohol is replaced by the reactant amine to form an amine product.
Claim 3
Dependent Claim
10 words
The process of claim 1 wherein the alcohol is aliphatic.
Claim 4
Dependent Claim
73 words
The process of claim 2 wherein the alcohol is represented by the formula: ##STR5## wherein A is OH or NHR: B is NR or 0: each R is independently hydrogen, a lower alkyl moiety of C 1 -C 12 carbon atoms, or a monocyclic aryl moiety: x is an integer from 2 to about 12: k is an integer from 0 to about and z is an integer from 1 to about 12.
Claim 5
Dependent Claim
10 words
The process of claim 3 wherein the alcohol is monoethanolamine.
Claim 6
Dependent Claim
13 words
The process of claim 1 wherein the reactant amine is an aliphatic amine.
Claim 7
Dependent Claim
71 words
The process of claim 5 wherein the reactant amine is represented by the formula: ##STR6## wherein B 1 is O or NR 2 ; each R 2 is independently a hydrogen or a lower alkyl moiety of C 1 -C 12 carbon atoms, or a monocyclic aryl moiety; each y is independently a positive integer from 1 to about 12, and n is a positive integer from 0 to about 150.
Claim 8
Dependent Claim
11 words
The process of claim 6 wherein the reactant amine is ethylenediamine.
Claim 9
Dependent Claim
11 words
The process of claim 6 wherein the reactant amine is diethylenetriamine.
Claim 10
Dependent Claim
12 words
The process of claim 1 wherein the Group VIB element is tungsten.
Claim 11
Dependent Claim
24 words
The process of claim 1 wherein the non-metallic element is selected from the group consisting of boron, carbon, nitrogen, silicon, phosphorus, and mixtures thereof.
Claim 12
Dependent Claim
20 words
The process of claim 10 wherein the non-metallic element is selected from the group consisting of boron, carbon, and nitrogen.
Claim 13
Dependent Claim
11 words
The process of claim 1 wherein the catalyst is tungsten boride.
Claim 14
Dependent Claim
11 words
The process of claim 1 wherein the catalyst is tungsten carbide.
Claim 15
Dependent Claim
11 words
The process of claim 1 wherein the catalyst is tungsten nitride.
Claim 16
Dependent Claim
14 words
The process of claim 1 wherein the catalyst is supported on a refractory oxide.
Claim 17
Dependent Claim
20 words
The process of claim 1 wherein the temperature is in the range from about 200° C. to about 400° C.
Claim 18
Dependent Claim
21 words
The process of claim 1 wherein the hydrogen partial pressure is in the range from about atmospheric to about 4000 psig.
Claim 19
Dependent Claim
95 words
The process of claim 1 wherein the amine product is represented by the general formula: ##STR7## wherein B and B 1 are each independently NR or O; each R and R 2 is independently hydrogen, a lower alkyl moiety of C 1 -C 12 carbon atoms, or a monocyclic aryl moiety; x is an integer from 2 to about 12; each y and z are independently a positive integer from 2 to about 12; k and n are each independently positive integers from 0 to about 150; and wherein Al is OH, NR or: ##STR8##
Claim 20
Dependent Claim
18 words
The process of claim 18 wherein the selectivity for non-cyclic polyalkylenepolyamines is at least about 30 weight percent.
Claim 21
Dependent Claim
66 words
A process for preparing predominately non-cyclic polyethylenepolyamines comprising contacting monoethanolamine with an ethylenediamine in the presence of hydrogen and a catalyst consisting essentially of tungsten boride or tungsten nitride, the contacting occurring under reaction conditions such that a mixture of polyethylenepolyamines is formed, wherein the diethylenetriamine/piperazine weight ratio is at least about 2, and the percentage of non-cyclic triethylenetetramines is at least about 45 weight percent.
Claim 22
Dependent Claim
66 words
A process for preparing predominately non-cyclic polyethylenepolyamines comprising contacting monoethanolamine with an ethylenediamine in the presence of hydrogen and a catalyst consisting essentially of tungsten boride or tungsten nitride, the contacting occurring under reaction conditions such that a mixture of polyethylenepolyamines is formed, wherein the diethylenetriamine/piperazine weight ratio is at least about 2, and the percentage of non-cyclic triethylenetetramines is at least about 45 weight percent.
Claim 23
Dependent Claim
18 words
The process of claim 18 wherein the selectivity for non-cyclic polyalkylenepolyamines is at least about 60 weight percent.
References Cited (Backward Citations)
US1875746A
Cited
US2033866A
Cited
US2082105A
Cited
US2285419A
Cited
US2394516A
Cited
US2591493A
Cited
US3037023A
Cited
US3272865A
Cited
US3231616A
Cited
US3285920A
Cited
US3383417A
Cited
US3475344A
Cited
US3491148A
Cited
US3510518A
Cited
US3714259A
Cited
JPS4896475A
Cited
US3875235A
Cited
US4217240A
Cited
US4206150A
Cited
US4495369A
Cited
US4314083A
Cited
US4325843A
Cited
US4404399A
Cited
US4647701A
Cited
US4740490A
Cited
US4683335A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-04-30 | 1993-10-30 | 1994-05-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-04-30 | 1997-10-30 | 1998-05-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-04-30 | 2001-10-30 | 2002-05-01 | $7700.00 | Window Closed / Lapsed |