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US4443384A
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Process for the manufacture of mixed phosphoric acid ester compositions
Assignee: FMC Corp
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Filing: 1982-10-04
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Granted: 1984-04-17
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Expires: 2002-10-04
Abstract
Abstract Mixed phosphoric acid ester compositions containing less than 4 weight percent of a triaryl phosphate, from about 10 to about 20 weight percent of an aryl dialkyl phosphate and from about 65 to about 80 weight percent of an alkyl diaryl phosphate are prepared by heating a monohydric alcohol with aqueous sodium hydroxide to form the sodium alkoxide, distilling off the water as an alcohol azeotrope and reacting the alcohol sodium alkoxide with a triphenyl phenol. The mixed phosphoric acid ester composition may be separated from by-products of the reaction by distillation.
Inventors
- 👤 Joseph H. Finley
- 👤 Hsiang P. Liao
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 02:09
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/12
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
237 words
A process for the manufacture of a mixed phosphoric acid ester composition comprising less than about 4 weight percent of triphenyl phosphate having the formula: (R.sub.1 O).sub.3 P═O from about 10 to about 20 weight percent of a phenyl dialkyl phosphate having the formula: ##STR8## and from about 65 to 80 weight percent of an alkyl diphenyl phosphate having the formula: ##STR9## wherein R 1 is a phenyl radical and R 2 is an alkyl radical, which comprises: (a) heating about 2 moles of an alcohol characterized by a boiling point above about 170° C. and having the formula: R.sub.2 CH.sub.2 CH.sub.2 OH with a catalytic amount of from greater than about 1.5 mole percent to about 2.0 mole percent based on the alcohol of an aqueous sodium hydroxide solution under vacuum to distill off the water present in the mixture and form a sodium alkoxide; (b) adding about 1.0 mole of triphenyl phosphate of the formula: (R.sub.1 O).sub.3 P═O to the reaction mixture under a nitrogen atmosphere and maintaining the temperature at about 100° C. with agitation for about an hour; (c) heating the reaction mixture at 100° C. to 140° C. under vacuum to remove aromatic and aliphatic alcohols from the reaction mixture; and (d) distilling the filtrate in a wiped film still under vacuum and at a temperature below the decomposition temperature of said mixed phosphoric acid ester composition to obtain the desired product.
Claim 2
Dependent Claim
237 words
A process for the manufacture of a mixed phosphoric acid ester composition comprising less than about 4 weight percent of triphenyl phosphate having the formula: (R.sub.1 O).sub.3 P═O from about 10 to about 20 weight percent of a phenyl dialkyl phosphate having the formula: ##STR8## and from about 65 to 80 weight percent of an alkyl diphenyl phosphate having the formula: ##STR9## wherein R 1 is a phenyl radical and R 2 is an alkyl radical, which comprises: (a) heating about 2 moles of an alcohol characterized by a boiling point above about 170° C. and having the formula: R.sub.2 CH.sub.2 CH.sub.2 OH with a catalytic amount of from greater than about 1.5 mole percent to about 2.0 mole percent based on the alcohol of an aqueous sodium hydroxide solution under vacuum to distill off the water present in the mixture and form a sodium alkoxide; (b) adding about 1.0 mole of triphenyl phosphate of the formula: (R.sub.1 O).sub.3 P═O to the reaction mixture under a nitrogen atmosphere and maintaining the temperature at about 100° C. with agitation for about an hour; (c) heating the reaction mixture at 100° C. to 140° C. under vacuum to remove aromatic and aliphatic alcohols from the reaction mixture; and (d) distilling the filtrate in a wiped film still under vacuum and at a temperature below the decomposition temperature of said mixed phosphoric acid ester composition to obtain the desired product.
Claim 3
Dependent Claim
10 words
The process of claim 1 wherein the alcohol is n-decanol.
Claim 4
Dependent Claim
10 words
The process of claim 1 wherein the alcohol is isodecanol.
Claim 5
Dependent Claim
33 words
The process of claim 1 wherein the reaction mixture is filtered after removal of the aromatic and aliphatic alcohols and prior to distillation to remove any insoluble salts that may be present therein.
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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) | 1987-04-17 | 1987-10-17 | 1988-04-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-04-17 | 1991-10-17 | 1992-04-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-04-17 | 1995-10-17 | 1996-04-17 | $7700.00 | Window Closed / Lapsed |