Patent FR831626A successfully refreshed from Google Patents.
US4017429A
Expired / Lapsed
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Preparation of 2-hydroxyalkyl esters
Assignee: Aerojet Rocketdyne Inc
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Filing: 1975-01-14
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Granted: 1977-04-12
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Expires: 1995-01-14
Abstract
Abstract This patent describes the catalytic promotion of the reaction of oxirane-containing compounds with carboxylic acid compounds at high, ambient, and low temperature. Specifically, this patent describes the method of reacting oxirane-containing compounds with carboxyl-containing compounds, preferably at temperatures at or around ambient, in the presence of active chromium III tricarboxylate salts which have unoccupied coordination sites. More specifically this patent describes the preparation of catalytically active chromium III-tricarboxylates from normally catalytically inactive chromium III tri-carboxylate hydrates. These compounds are powerful catalysts for the reactions of oxirane compounds with both organic carboxylic acids and cyclic primary imides.
Inventors
- 👤 Roger B. Steele
- 👤 Arthur Katzakian, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 22:32
CPC Classifications
C; C07; C07C; C07C67/00; C07C67/24; C07C67/26; B; B01; B01J; B01J31/00; B01J31/02; B01J31/04; B01J2231/00; B01J2231/40; B01J2231/48
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
103 words
A method of forming as ester linkage which comprises reacting an organic carboxylic acid with an organic oxirane compound in the presence of an effective catalytic amount of soluble chromium III carboxylate of the formula: Cr(OOCR.sup.a).sub.3 where OOCR a is a carboxylate group containing at least 4 carbon atoms, said catalyst being the reaction product of a hydrated Cr III tricarboxylate heated in an excess of organic acid to a temperature above 140° C and said reaction product having the following characteristics: 1. emerald green in color; 2. slightly soluble in hexane but fully soluble in acetone; 3. melts slightly above room temperature;
Claim 2
Independent Claim
103 words
A method of forming as ester linkage which comprises reacting an organic carboxylic acid with an organic oxirane compound in the presence of an effective catalytic amount of soluble chromium III carboxylate of the formula: Cr(OOCR.sup.a).sub.3 where OOCR a is a carboxylate group containing at least 4 carbon atoms, said catalyst being the reaction product of a hydrated Cr III tricarboxylate heated in an excess of organic acid to a temperature above 140° C and said reaction product having the following characteristics: 1. emerald green in color; 2. slightly soluble in hexane but fully soluble in acetone; 3. melts slightly above room temperature;
Claim 3
Dependent Claim
37 words
does not exhibit a water absorption peak at 2750 mμ in the near infrared 5. at least 90% of the carboxylate carbonyl absorption is at 1615 cm - 1 and not at 1540 cm - 1 .
Claim 4
Dependent Claim
37 words
does not exhibit a water absorption peak at 2750 mμ in the near infrared 5. at least 90% of the carboxylate carbonyl absorption is at 1615 cm - 1 and not at 1540 cm - 1 .
Claim 5
Dependent Claim
29 words
A method according to claim 1 in which OOCR a is selected from butyrate, pentanoate, hexanoate, 2-ethyl, hexanoate, decanoate, oleate, stearate, toluate, cresylate, benzoate, alkyl benzoate, alkoxybenzoate, and napthenate.
Claim 6
Dependent Claim
13 words
A method according to claim 2 in which OOCR a is 2-ethyl hexanoate.
Claim 7
Dependent Claim
37 words
A method according to claim 1 in which the organic oxirane compound is of the formula: ##STR14##where R' and R" are individually selected from the group consisting of hydrogen and alkyl of 1 to 20 carbon atoms.
Claim 8
Dependent Claim
16 words
The method of claim 1 wherein the esterification reaction is carried out at about ambient temperature.
Claim 9
Dependent Claim
25 words
The method of claim 1 wherein the chromium III carboxylate is present in an amount of from 0.1% to about 10% by weight of reactants.
Claim 10
Dependent Claim
25 words
The method of claim 4 wherein the oxirane compound is selected from the group consisting of ethylene oxide, propylene oxide, 1,2-butylene oxide and 2,3-butylene oxide.
Claim 11
Dependent Claim
20 words
The method of claim 1 wherein the organic carboxylic acid contains one (--COOH) group and the oxirane is mono functional.
Claim 12
Dependent Claim
31 words
The method of claim 8 wherein the organic carboxylic acid is selected from the group consisting of 2-ethylhexanoic, adipic, acrylic, acetic, azelaic, oxalic, cyclohexanetricarboxylic, trimesic, sebacic, terephthalic acids and polyacrylic acids.
Claim 13
Dependent Claim
19 words
The method of claim 1 wherein a stoichiometric amount of acid is reacted with a stoichiometric amount of oxirane.
Claim 14
Dependent Claim
39 words
The method of claim 1 wherein the oxirane compound is selected from the group consisting of a glycidyl ether of a mono-functional alcohol, a glycidyl ether of a monofunctional phenol, and a glycidyl ether of a monofunctional organic acid.
Claim 15
Dependent Claim
15 words
The method of claim 1 wherein the oxirane compound contains at least two oxirane groups.
Claim 16
Dependent Claim
13 words
The method of claim 1 wherein the oxirane compound is a polyepoxide resin.
Claim 17
Dependent Claim
15 words
The method of claim 1 wherein the organic carboxylic acid is a difunctional or polyfunctional.
Claim 18
Dependent Claim
16 words
The method of claim 1 wherein the organic carboxylic acid contains at least two carboxyl groups.
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) | 1980-04-11 | 1980-10-11 | 1981-04-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-04-11 | 1984-10-11 | 1985-04-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-04-11 | 1988-10-11 | 1989-04-12 | $7700.00 | Window Closed / Lapsed |