US4093650A
Expired / Lapsed
US
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Process for preparing trihydrocarbyl (2,5-dihydroxyphenyl) phosphonium salts
Assignee: Dow Chemical Co
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Filing: 1976-04-23
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Granted: 1978-06-06
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Expires: 1996-04-23
Abstract
Abstract The title compounds are prepared by reacting (a) a trihydrocarbylphosphine, (b) p-benzoquinone, and (c) a protic acid in a liquid reaction medium comprising a lower alkanol of from 1 to 4 carbon atoms, a 1,2-alkylene glycol, dialkylene glycol or trialkylene glycol or a lower alkyl mono-ether of said glycols. The glycols are either ethylene glycol, propylene glycol, or the indicated oligomers thereof. Methanol is the solvent of choice. As an example, tri-n-butyl (2,5-dihydroxyphenyl)phosphonium chloroacetate was prepared in excellent yields by slowly adding tri-n-butylphosphine, precooled to about 0° C, to a vigorously stirred suspension of p-benzoquinone in a methanol solution of chloroacetic acid at a temperature of approximately -10° C. A precatalyzed epoxy resin was obtained by merely adding the methanol solution of the phosphonium chloroacetate to a liquid epoxy resin (e.g., the diglycidyl ether of bisphenol-A).
Inventors
- 👤 George A. Doorakian
- 👤 Lawrence G. Duquette
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 08:46
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/54; C07F9/5442
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
139 words
A process for preparing a compound of the formula ##STR2## wherein: R 1 , R 2 and R 3 are each independently hydrocarbyl or inertly-substituted hydrocarbyl groups of from 1 to about 20 carbon atoms, and A.sup.⊖ is an inert neutralizing anion; said process comprising reacting by contacting in essentially stoichiometric amounts (a) a phosphine of the formula R 1 R 2 R 3 P, wherein R 1 -R 3 have the aforesaid meanings, (b) p-benzoquinone, and (c) a protic acid of the formula H.sup.⊕ A.sup.⊖, wherein A.sup.⊖ has the aforesaid meaning in a liquid reaction medium consisting essentially of a lower alkanol of from 1 to 4 carbon atoms, 1,2-ethylene glycol, 1,2-propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, or a lower alkyl (C 1 -C 4 ) ether of said glycols, or a mixture thereof.
Claim 2
Dependent Claim
139 words
A process for preparing a compound of the formula ##STR2## wherein: R 1 , R 2 and R 3 are each independently hydrocarbyl or inertly-substituted hydrocarbyl groups of from 1 to about 20 carbon atoms, and A.sup.⊖ is an inert neutralizing anion; said process comprising reacting by contacting in essentially stoichiometric amounts (a) a phosphine of the formula R 1 R 2 R 3 P, wherein R 1 -R 3 have the aforesaid meanings, (b) p-benzoquinone, and (c) a protic acid of the formula H.sup.⊕ A.sup.⊖, wherein A.sup.⊖ has the aforesaid meaning in a liquid reaction medium consisting essentially of a lower alkanol of from 1 to 4 carbon atoms, 1,2-ethylene glycol, 1,2-propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, or a lower alkyl (C 1 -C 4 ) ether of said glycols, or a mixture thereof.
Claim 3
Dependent Claim
16 words
The process defined by claim 1 wherein R 1 -R 3 are each phenyl or n-butyl.
Claim 4
Dependent Claim
14 words
The process defined by claim 2 wherein R 1 -R 3 are each n-butyl.
Claim 5
Dependent Claim
29 words
The process defined by claim 1 wherein said process is conducted at a reaction temperature of from the freezing point of the reaction mixture up to about 60° C.
Claim 6
Dependent Claim
24 words
The process defined by claim 4 wherein the reaction temperature is from the freezing point of the reaction mixture up to about 0° C.
Claim 7
Dependent Claim
19 words
The process defined by claim 5 wherein the reaction temperature is from about -40° C to about 0° C.
Claim 8
Dependent Claim
26 words
The process defined by claim 1 wherein (a) is added incrementally to an efficiently blended reaction mixture of (b) and (c) in said liquid reaction medium.
Claim 9
Dependent Claim
35 words
The process defined by claim 7 wherein R 1 -R 3 are each n-butyl or phenyl; the reaction temperature is from about -40° C to about 0° C; and said liquid reaction medium is methanol.
Claim 10
Dependent Claim
33 words
The process defined by claim 8 wherein R 1 -R 3 are each n-butyl and (c) is HBF 4 , H 3 PO 4 , HC1, acrylic acid, chloroacetic acid or acetic acid.
Claim 11
Dependent Claim
11 words
The process defined by claim 9 wherein (c) is chloroacetic acid.
Claim 12
Dependent Claim
15 words
The process defined in claim 1 wherein A.sup.⊖ is bromide, iodide or a non-nucleophilic anion.
Claim 13
Dependent Claim
19 words
The process defined by claim 11 wherein said non-nucleophilic anion is bisulfate, acetate, diacetate, chloroacetate, trifluoroacetate, acrylate, or adipate.
References Cited (Backward Citations)
US2862970A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-05 | 1981-12-05 | 1982-06-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-05 | 1985-12-05 | 1986-06-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-05 | 1989-12-05 | 1990-06-06 | $7700.00 | Window Closed / Lapsed |