US4095022A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Production of bis-(morpholino-n-alkyl) ethers
Assignee: Texaco Development Corp
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Filing: 1976-04-23
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Granted: 1978-06-13
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Expires: 1996-04-23
Abstract
Abstract An improved process is disclosed for selectively producing a bis-(morpholino-N-alkyl) ether directly from the corresponding N-(hydroxyalkyl)morpholine compound. The improved process includes contacting the N-(hydroxyalkyl)morpholine compound with a catalytically effective amount of a silica-alumina or certain phosphorus containing substances at a temperature of about 200° C to 300° C under a pressure sufficient to maintain the mixture substantially in liquid phase and recovering from the resultant reaction mixture the bis-(morpholino-N-alkyl) ether. According to the preferred embodiment, N-(2-hydroxyethyl)morpholine is heated in the presence of a catalytic amount of a silica-alumina catalyst having an alumina content of from about 5 to about 50 wt. % at temperatures of from about 240° C to about 290° C in liquid phase to selectively produce the corresponding N,N',2,2'-dimorpholinodiethyl ether (DMDEE).
Inventors
- 👤 Michael E. Brennan
- 👤 Philip H. Moss
- 👤 Ernest L. Yeakey
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 22:19
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/02; C07D295/023; C07D295/04; C07D295/08; C07D295/084; C07D295/088; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/16; C08G18/18; C08G18/20; C08G18/2009; C08G18/2018; C08G18/2081
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
171 words
A process for producing a bis-(morpholino-N-alkyl) ether compound from the corresponding N-(hydroxyalkyl)morpholine compound, said N-(hydroxyalkyl)morpholine compound having the formula: ##STR2## wherein R is a straight chain or a branched chain alkyl radical of from 2 to 10 carbon atoms, R' is a lower alkyl radical, and n is an integer from 0 to 4 comprising the steps of: contacting said N-(hydroxyalkyl)morpholine compound with a catalytically effective amount of a phosphorus-containing substance selected from the group consisting of acidic metal phosphates, phosphoric acids and their anhydrides, or phosphorous acids and their anhydrides, alkyl or aryl phosphate esters, alkyl or aryl phosphite esters, alkyl or aryl substituted phosphorous and phosphoric acids, alkali metal monosalts of phosphoric acid, the thioanalogs of the foregoing, phosphoric acid-impregnated silicas having from about 10 to about 30 wt. % phosphoric acid and mixtures thereof, at a temperature of from about 200° C to about 300° C under a pressure sufficient to maintain the mixture substantially in liquid phase; and recovering said bis-(morpholino-N-alkyl) ether compound from the reaction mixture.
Claim 2
Dependent Claim
171 words
A process for producing a bis-(morpholino-N-alkyl) ether compound from the corresponding N-(hydroxyalkyl)morpholine compound, said N-(hydroxyalkyl)morpholine compound having the formula: ##STR2## wherein R is a straight chain or a branched chain alkyl radical of from 2 to 10 carbon atoms, R' is a lower alkyl radical, and n is an integer from 0 to 4 comprising the steps of: contacting said N-(hydroxyalkyl)morpholine compound with a catalytically effective amount of a phosphorus-containing substance selected from the group consisting of acidic metal phosphates, phosphoric acids and their anhydrides, or phosphorous acids and their anhydrides, alkyl or aryl phosphate esters, alkyl or aryl phosphite esters, alkyl or aryl substituted phosphorous and phosphoric acids, alkali metal monosalts of phosphoric acid, the thioanalogs of the foregoing, phosphoric acid-impregnated silicas having from about 10 to about 30 wt. % phosphoric acid and mixtures thereof, at a temperature of from about 200° C to about 300° C under a pressure sufficient to maintain the mixture substantially in liquid phase; and recovering said bis-(morpholino-N-alkyl) ether compound from the reaction mixture.
Claim 3
Dependent Claim
25 words
The process according to claim 1 wherein said catalyst is a phosphoric acid-impregnated silica having from about 5 to about 30 wt. % phosphoric acid.
Claim 4
Dependent Claim
29 words
The process according to claim 1 wherein said phosphorus-containing substance is phosphorous acid in an aqueous solution in an amount of from about 5 to about 70 wt. %.
Claim 5
Dependent Claim
13 words
The process according to claim 1 wherein said phosphorus-containing substance is ferric phosphate.
Claim 6
Dependent Claim
13 words
The process according to claim 1 wherein said phosphorus-containing substance is boron phosphate.
Claim 7
Dependent Claim
13 words
The process according to claim 1 wherein said phosphorus-containing substance is aluminum phosphate.
Claim 8
Dependent Claim
24 words
The process according to claim 1 wherein said contacting is carried out at a temperature of from about 240° C to about 280° C.
Claim 9
Dependent Claim
21 words
The process according to claim 1 wherein R and R', are independently, alkyl radicals having from 2 to 3 carbon atoms.
Claim 10
Dependent Claim
43 words
The process according to claim 1 wherein said contacting is effected at a pressure of from about 10 to about 1000 psig and wherein water is continuously removed from the reaction zone as a vapor as it is formed in the condensation reaction.
Claim 11
Dependent Claim
24 words
The process according to claim 1 wherein said contacting is carried out at a temperature of from about 255° C to about 265° C.
Claim 12
Dependent Claim
19 words
The process according to claim 1 wherein said N-(hydroxyalkyl)morpholine is N-(2-hydroxyethyl)-2,6-dimethylmorpholine and N,N'-bis(2,6-dimethylmorpholinoethyl)ether is recovered from the reaction mixture.
Claim 13
Dependent Claim
19 words
The process according to claim 1 wherein said N-(hydroxyalkyl)morpholine is N-(2-hydroxyethyl)morpholine, and N,N'-(dimorpholinodiethyl)ether is recovered from the reaction mixture.
Claim 14
Dependent Claim
19 words
The process according to claim 1 wherein said N-(hydroxyalkyl)morpholine is N-(2-hydroxypropyl)morpholine and N,N'-(dimorpholinodiisopropyl)ether is recovered from the reaction mixture.
References Cited (Backward Citations)
US3112317A
Cited
US4026935A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-12 | 1981-12-12 | 1982-06-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-12 | 1985-12-12 | 1986-06-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-12 | 1989-12-12 | 1990-06-13 | $7700.00 | Window Closed / Lapsed |