Claims
- 1. 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.degree. C to about 300.degree. 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.
- 2. 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.
- 3. 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. %.
- 4. The process according to claim 1 wherein said phosphorus-containing substance is ferric phosphate.
- 5. The process according to claim 1 wherein said phosphorus-containing substance is boron phosphate.
- 6. The process according to claim 1 wherein said phosphorus-containing substance is aluminum phosphate.
- 7. The process according to claim 1 wherein said contacting is carried out at a temperature of from about 240.degree. C to about 280.degree. C.
- 8. The process according to claim 1 wherein R and R', are independently, alkyl radicals having from 2 to 3 carbon atoms.
- 9. 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.
- 10. The process according to claim 1 wherein said contacting is carried out at a temperature of from about 255.degree. C to about 265.degree. C.
- 11. 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.
- 12. 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.
- 13. 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.
Parent Case Info
This is a division of application Ser. No. 583,014, filed June 2, 1975, now U.S. Pat. No. 4,026,935, granted May 31, 1977.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
3112317 |
Marschall et al. |
Nov 1963 |
|
4026935 |
Brennan et al. |
May 1977 |
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Divisions (1)
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Number |
Date |
Country |
Parent |
583014 |
Jun 1975 |
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