Patent US4034023A successfully refreshed from Google Patents.
US4034023A
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Process for preparing mixed phosphate ester compositions
Assignee: FMC Corp
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Filing: 1975-05-05
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Granted: 1977-07-05
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Expires: 1995-05-05
Abstract
Abstract Preparing mixed phosphate ester compositions consisting essentially of 10% to 19% tributyl phosphate, 62% to 80% dibutyl phenyl phosphate, and 10% to 19% butyl diphenyl phosphate which comprises forming a first reaction product by reacting phosphorus oxychloride with phenol in a molar ratio of 1:0.8 to 1.0 until less than 1% unreacted phenol is present in the reaction mixture, reacting the first reaction product with excess n-butanol at a temperature below 35° C to prepare a crude mixed phosphate ester composition comprising tributyl phosphate, dibutyl phenyl phosphate and butyl diphenyl phosphate, and purifying the crude composition leaving a substantially pure mixed phosphate ester composition.
Inventors
- 👤 Donald Hardy, Sr.
- 👤 Edward Francis Orwoll
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 17:29
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/12; C10; C10M; C10M3/00; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/042; C10N; C10N2040/00; C10N2040/08
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
189 words
A process for preparing a mixed phosphate ester composition consisting essentially of 10% to 19% tributyl phosphate, 62% to 80% dibutyl phenyl phosphate, and 10% to 19% butyl diphenyl phosphate, which comprises: (a) reacting phosphorus oxychloride with phenol in a molar ratio 1:0.8 to 1.0 at a temperature of about 40° to about 100° C. until less than 1% unreacted phenol is present in the reaction mixture while moving liberated hydrogen chloride from the reaction mixture to prepare a first reaction product comprising crude phenyl phosphorodichloridate, diphenyl phosphorochloridate and unreacted phosphorus oxychloride; (b) reacting the first reaction product with at least two moles of n-butanol per replaceable chloride under agitation at a temperature below 35° C. for a sufficient time to prepare a second reaction product comprising crude tributyl phosphate, dibutyl phenyl phosphate, and butyl diphenyl phosphate; and (c) purifying the second reaction product by removing acid esters, acidic impurities, salts and unreacted n-butanol from the second reaction product thereby leaving a substantially pure mixed phosphate ester composition consisting essentially of 10% to 19% tributyl phosphate, 62% to 80% dibutyl phenyl phosphate, and 10% to 19% butyl diphenyl phosphate.
Claim 2
Dependent Claim
189 words
A process for preparing a mixed phosphate ester composition consisting essentially of 10% to 19% tributyl phosphate, 62% to 80% dibutyl phenyl phosphate, and 10% to 19% butyl diphenyl phosphate, which comprises: (a) reacting phosphorus oxychloride with phenol in a molar ratio 1:0.8 to 1.0 at a temperature of about 40° to about 100° C. until less than 1% unreacted phenol is present in the reaction mixture while moving liberated hydrogen chloride from the reaction mixture to prepare a first reaction product comprising crude phenyl phosphorodichloridate, diphenyl phosphorochloridate and unreacted phosphorus oxychloride; (b) reacting the first reaction product with at least two moles of n-butanol per replaceable chloride under agitation at a temperature below 35° C. for a sufficient time to prepare a second reaction product comprising crude tributyl phosphate, dibutyl phenyl phosphate, and butyl diphenyl phosphate; and (c) purifying the second reaction product by removing acid esters, acidic impurities, salts and unreacted n-butanol from the second reaction product thereby leaving a substantially pure mixed phosphate ester composition consisting essentially of 10% to 19% tributyl phosphate, 62% to 80% dibutyl phenyl phosphate, and 10% to 19% butyl diphenyl phosphate.
Claim 3
Dependent Claim
50 words
The process of claim 1 wherein the first reaction product is slowly added to the excess n-butanol under agitation at a temperature of about 15° to 20° C. until the addition is complete whereupon the reaction temperature is maintained at about 20° to 30° C. until the reaction is completed.
Claim 4
Dependent Claim
82 words
The process of claim 1 wherein the second reaction product is purified by contacting the second reaction product with a strong caustic solution to provide an excess of caustic at a temperature below 35° C. so that the resulting aqueous phase has a pH value higher than 10.5, separating the resulting organic phase from the aqueous phase, removing by distillation unreacted n-butanol from the organic phase and washing the residual phosphate ester product with a dilute caustic solution to remove remaining impurities.
Claim 5
Dependent Claim
41 words
The process of claim 3 wherein the second reaction product is contacted with a 15 to 25 weight % caustic solution at a temperature between 0° and 30° C. so that the resulting aqueous phase has a pH value above 11.0.
Claim 6
Dependent Claim
29 words
The process of claim 1 wherein the purified mixed phosphate ester composition is vacuum dried at a temperature between 50° and 150° C. at 5 to 100 mm Hg.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-04 | 1981-01-03 | 1981-07-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-04 | 1985-01-03 | 1985-07-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-04 | 1989-01-03 | 1989-07-05 | $7700.00 | Window Closed / Lapsed |