US4582904A
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US
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Amine production via condensation reactions using rare earth metal hydrogen phosphates as catalysts
Assignee: Air Products and Chemicals Inc
•
Filing: 1984-01-06
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Granted: 1986-04-15
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Expires: 2004-01-06
Abstract
Abstract Synthesis of organic amines by condensation of organic hydroxy compound with ammonia or a primary or secondary amine in the presence of a rare earth metal hydrogen phosphate catalyst.
Inventors
- 👤 James E. Wells
- 👤 Victoria Eskinazi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 17:58
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/02; C07D295/023; B; B01; B01J; B01J27/00; B01J27/14; B01J27/16; B01J27/18; B01J27/1802; C07D295/04; C07D295/12; C07D295/125; C07D295/13; C07D487/00; C07D487/02; C07D487/08
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
229 words
In a process for the synthesis of an organic amine by the condensation of a hydroxy composition with ammonia or a primary or secondary amine said condensation being effected in the presence of a phosphorus-containing compound as a catalyst, the improvement which comprises: effecting condensation between (a) an organic hydroxy composition represented by the formula: R(OH) x where R is a saturated aliphatic radical having from 1 to 6 carbon atoms, an olefinic radical having from 3 to 6 carbon atoms, aliphatic ether having from 4 to 8 carbon atoms or aminoaliphatic where the aliphatic portion has from 2-6 carbon atoms: and x is 1 when R is methyl and 1 or 2 when R, has 2 or more carbon atoms and (b) an amino composition represented by the formula: R 1 R 2 NH where R 1 and R 2 are each selected from hydrogen, a saturated aliphatic radical having from 1 to 4 carbon atoms, an olefinic radical having 3-6 carbon atoms, hydroxyalkyl where the alkyl portion has from 2 to 6 carbon atoms, and aliphatic ether having from 4-8 carbon atoms or R 1 and R 2 are are combined with the nitrogen to form a heterocyclic group having 4 to 10 carbon atoms; except where compositions (a) and (b) are defined by the same formula and then only one of said compositions is required; and
Claim 2
Dependent Claim
229 words
In a process for the synthesis of an organic amine by the condensation of a hydroxy composition with ammonia or a primary or secondary amine said condensation being effected in the presence of a phosphorus-containing compound as a catalyst, the improvement which comprises: effecting condensation between (a) an organic hydroxy composition represented by the formula: R(OH) x where R is a saturated aliphatic radical having from 1 to 6 carbon atoms, an olefinic radical having from 3 to 6 carbon atoms, aliphatic ether having from 4 to 8 carbon atoms or aminoaliphatic where the aliphatic portion has from 2-6 carbon atoms: and x is 1 when R is methyl and 1 or 2 when R, has 2 or more carbon atoms and (b) an amino composition represented by the formula: R 1 R 2 NH where R 1 and R 2 are each selected from hydrogen, a saturated aliphatic radical having from 1 to 4 carbon atoms, an olefinic radical having 3-6 carbon atoms, hydroxyalkyl where the alkyl portion has from 2 to 6 carbon atoms, and aliphatic ether having from 4-8 carbon atoms or R 1 and R 2 are are combined with the nitrogen to form a heterocyclic group having 4 to 10 carbon atoms; except where compositions (a) and (b) are defined by the same formula and then only one of said compositions is required; and
Claim 3
Dependent Claim
14 words
Employing as said phosphorus-containing compound a catalyst comprising a rare earth metal hydrogen phosphate.
Claim 4
Dependent Claim
14 words
Employing as said phosphorus-containing compound a catalyst comprising a rare earth metal hydrogen phosphate.
Claim 5
Dependent Claim
17 words
The process of claim 1 wherein said rare earth metal hydrogen phosphate comprises a lanthanum hydrogen phosphate.
Claim 6
Dependent Claim
14 words
The process of claim 2 wherein x in said organic hydroxy composition is 1.
Claim 7
Dependent Claim
22 words
The process of claim 3 wherein R in said organic hydroxy composition is a saturated aliphatic radical having from 1-6 carbon atoms.
Claim 8
Dependent Claim
71 words
The process of claim 3 wherein said organic hydroxy compound is an alkanol having from 1 to 4 carbon atoms or an alkanolamine having from 1 to 4 carbon atoms and said amino compound is a primary or secondary amine and R 1 and R 2 are each selected from hydrogen or saturated aliphatic radical having from 1 to 4 carbon atoms and the product is a symmetrical or unsymmetrical amine.
Claim 9
Dependent Claim
17 words
The process of claim 3 wherein R 1 and R 2 in said amino compound are hydrogen.
Claim 10
Dependent Claim
19 words
The process of claim 3 wherein R 1 is hydrogen or and R 2 is a saturated aliphatic radical.
Claim 11
Dependent Claim
20 words
The process of claim 5 wherein said organic hydroxy composition is methanol and said amino compound is methylamine or ethylamine.
Claim 12
Dependent Claim
27 words
The process of claim 3 wherein said amino composition R 1 and R 2 are joined to form a heterocyclic group having 4 to 10 carbon atoms.
Claim 13
Dependent Claim
11 words
The process of claim 9 wherein said amino compound is piperazine.
Claim 14
Dependent Claim
11 words
The process of claim 9 wherein said amino compound is morpholine.
Claim 15
Dependent Claim
21 words
The process of claim 2 wherein R is C 2 or greater in said organic hydroxy compound and x is 2.
Claim 16
Dependent Claim
13 words
The process of claim 12 wherein said organic hydroxy compound is diethylene glycol.
Claim 17
Dependent Claim
21 words
The process of claim 13 wherein said amino compound is ammonia or an alkylamine having from 2 to 3 carbon atoms.
Claim 18
Dependent Claim
13 words
The process of claim 12 wherein said organic hydroxy composition is ethylene glycol.
Claim 19
Dependent Claim
19 words
The process of claim 2 wherein said organic hydroxy compound is an alkanolamine and said amino compound is morpholine.
Claim 20
Dependent Claim
12 words
The process of claim 16 wherein said organic hydroxy compound is dimethylethanolamine.
Claim 21
Dependent Claim
21 words
The process of claim 2 wherein said organic hydroxy compound is an alkoxy alkanol having from 4 to 8 carbon atoms.
Claim 22
Dependent Claim
22 words
The process of claim 18 wherein R 1 and R 2 of said amino composition are combined to form a heterocyclic group.
Claim 23
Dependent Claim
14 words
The process of claim 19 wherein said amino compound is piperidine, piperazine or morpholine.
Claim 24
Dependent Claim
16 words
The process of claim 20 wherein said rare earth hydrogen phosphate comprises a lanthanum hydrogen phosphate.
Claim 25
Dependent Claim
25 words
The process of claim 1 wherein in said amino composition R 1 and R 2 are combined with the nitrogen to form a heterocyclic group.
Claim 26
Dependent Claim
13 words
The process of claim 2 wherein (a) and (b) are hydroxy ethyl piperazine.
Claim 27
Dependent Claim
11 words
The process of claim 2 wherein (a) and (b) are 2-aminoethoxyethanol.
Claim 28
Dependent Claim
28 words
The process of claim 2 wherein said hydroxy compound is allyl alcohol and said amine compound is ammonia or an alkylamine having from 1 to 4 carbon atoms.
Claim 29
Dependent Claim
21 words
The process of claim 2 wherein said organic hydroxy and amino compound is an alkanol amine having from 2-4 carbon atoms.
Claim 30
Dependent Claim
10 words
The process of claim 26 wherein said alkanolamine is monoethanolamine.
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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) | 1989-04-14 | 1989-10-14 | 1990-04-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-04-14 | 1993-10-14 | 1994-04-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-04-14 | 1997-10-14 | 1998-04-15 | $7700.00 | Window Closed / Lapsed |