Patent US4026935A successfully refreshed from Google Patents.
US4026935A
Expired / Lapsed
US
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Production of bis-(morpholino-N-alkyl) ethers
Assignee: Texaco Development Corp
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Filing: 1975-06-02
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Granted: 1977-05-31
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Expires: 1995-06-02
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 280° 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
2026-11-02 07:44
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: 16
Claim 1
Independent Claim
117 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 claim or a branched chain alkyl radical of from 2 to about 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 silica-alumina having an alumina content of from about 5 to about 50 wt. % 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
26 words
The process according to claim 1 wherein said silica-alumina has a surface area of from about 50 m 2 /g to about 700 m 2 /g.
Claim 3
Dependent Claim
24 words
The process according to claim 2 wherein said contacting is carried out at a temperature of from about 240° C. to about 280° C.
Claim 4
Dependent Claim
22 words
The process according to claim 3 wherein R and R' are, independently, alkyl radicals having from 2 to about 4 carbon atoms.
Claim 5
Dependent Claim
23 words
The process according to claim 4 wherein the silica-alumina catalyst has an alumina content of from about 10 to about 40 wt. %.
Claim 6
Dependent Claim
43 words
The process according to claim 5 wherein said contacting is effected at a pressure of from about 10 to about 100 psig and wherein water is continuously removed from the reaction zone as a vapor as it is formed in the condensation reaction.
Claim 7
Dependent Claim
24 words
The process according to claim 6 wherein said contacting is carried out at a temperature of from about 255° C. to about 265° C.
Claim 8
Dependent Claim
22 words
The process according to claim 7 wherein said N-(hydroxyalkyl)morpholine is selected from the group consisting of N-(2-hydroxyethyl)-2,6-dimethylmorpholine, N-(2-hydroxyethyl)morpholine, N-(2-hydroxypropyl)morpholine, N-(3-hydroxypropyl)morpholine, N-(2-hydroxyethyl)-2-methyl morpholine.
Claim 9
Dependent Claim
150 words
A continuous process for preparing a bis-(morpholino-N-alkyl) ether compound from the corresponding N-(hydroxyalkyl) morpholine compound, said N-(hydroxyalkyl)morpholine compound having the formula: ##STR3## wherein R is a straight chain or a branched chain alkyl radical of from 2 to about 10 carbon atoms, R' is a lower alkyl radical, and n is an integer from 0 to 4, said continuous process comprising: feeding said N-(hydroxyalkyl)morpholine compound to a fixed bed reactor at weight hourly space velocity of from about 0.1 to about 5.0 g/ml catalyst/hr at temperatures of from about 240° C. to 280° C. at a reactor pressure of about 50 psig wherein said fixed bed is of silica-alumina containing from about 5 to about 50 wt. % alumina and having a surface area of from about 50 m 2 /g to about 700 m 2 /g; and, recovering the bis-(morpholino-N-alkyl) ether compound from the effluent issuing from said reactor.
Claim 10
Dependent Claim
150 words
A continuous process for preparing a bis-(morpholino-N-alkyl) ether compound from the corresponding N-(hydroxyalkyl) morpholine compound, said N-(hydroxyalkyl)morpholine compound having the formula: ##STR3## wherein R is a straight chain or a branched chain alkyl radical of from 2 to about 10 carbon atoms, R' is a lower alkyl radical, and n is an integer from 0 to 4, said continuous process comprising: feeding said N-(hydroxyalkyl)morpholine compound to a fixed bed reactor at weight hourly space velocity of from about 0.1 to about 5.0 g/ml catalyst/hr at temperatures of from about 240° C. to 280° C. at a reactor pressure of about 50 psig wherein said fixed bed is of silica-alumina containing from about 5 to about 50 wt. % alumina and having a surface area of from about 50 m 2 /g to about 700 m 2 /g; and, recovering the bis-(morpholino-N-alkyl) ether compound from the effluent issuing from said reactor.
Claim 11
Dependent Claim
32 words
The pressure of claim 9 wherein said weight hourly space velocity is about 0.2 to about 2.0 g/ml catalyst/hr and said alumina content is from about 10 to about 40 wt. %.
Claim 12
Dependent Claim
41 words
The process of claim 10 comprising the further step of vacuum stripping the crude reaction product under conditions of from about 760 mm Hg/225° C. to 1.0 mm Hg/60° C. to effect removal of unreacted reagent and residual water of reaction.
Claim 13
Dependent Claim
19 words
The process of claim 9 wherein R contains from 2 to about 4 carbon atoms and n is 0.
Claim 14
Dependent Claim
19 words
The process of claim 9 wherein said N-(hydroxyalkyl)morpholine compound is selected from N-(2-hydroxyethyl)morpholine, N-(3-hydroxypropyl)morpholine, N-(2-hydroxypropyl)morpholine, N-(2-hydroxyethyl)-2-ethyl morpholine, and N-(2-hydroxyethyl)-2,6-dimethylmorpholine.
Claim 15
Dependent Claim
103 words
A process for producing a bis-(morpholino-alkyl) ether compound from the corresponding N-(hydroxyalkyl)-morpholine compound wherein said N-(hydroxyalkyl) morpholine compound is selected from the group consisting of N-(2-hydroxy-ethyl)-2,6-dimethyl morpholine, N-(2-hydroxyethyl) morpholine and N-(2-hydroxypropyl) morpholine comprising the steps of: contacting said N-(hydroxyalkyl)morpholine compound with a catalytically effective amount of silica alumina at a temperature of from about 255° C. to about 265° C at a pressure from about 10 to about 100 psig, wherein said silica alumina has an alumina content of from about 5 to about 50 wt. %; a surface area of from about 50 m 2 /g to about 700 m 2 g.
Claim 16
Dependent Claim
103 words
A process for producing a bis-(morpholino-alkyl) ether compound from the corresponding N-(hydroxyalkyl)-morpholine compound wherein said N-(hydroxyalkyl) morpholine compound is selected from the group consisting of N-(2-hydroxy-ethyl)-2,6-dimethyl morpholine, N-(2-hydroxyethyl) morpholine and N-(2-hydroxypropyl) morpholine comprising the steps of: contacting said N-(hydroxyalkyl)morpholine compound with a catalytically effective amount of silica alumina at a temperature of from about 255° C. to about 265° C at a pressure from about 10 to about 100 psig, wherein said silica alumina has an alumina content of from about 5 to about 50 wt. %; a surface area of from about 50 m 2 /g to about 700 m 2 g.
References Cited (Backward Citations)
US3645925A
Cited
US3817997A
Cited
USPTO Annuity & Maintenance Windows
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| 3.5 Years (Year 4) | 1980-05-30 | 1980-11-29 | 1981-05-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-30 | 1984-11-29 | 1985-05-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-30 | 1988-11-29 | 1989-05-31 | $7700.00 | Window Closed / Lapsed |