Patent US2331840A successfully refreshed from Google Patents.
Patent US5124475A successfully refreshed from Google Patents.
US5124475A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of p-phenyl sulfonate esters of acyl glycolic acids
Assignee: Stepan Co
•
Filing: 1991-03-01
•
Granted: 1992-06-23
•
Expires: 2011-03-01
Abstract
Abstract The invention encompasses methods for preparing in high purity and in high yield p-phenyl sulfonic acid acyl glycolates of the formula ##STR1## where R represents branched or straight chain alkyl having 6-12 carbon atoms by treating a phenyl ester or phenyl acyl glycolate of the formula ##STR2## where R represents branched or straight chain alkyl having 6-12 carbon atoms with a sulfonating agent to form intermediate sulfonation; transmuting the intermediate sulfonation products; and quenching the transmuted intermediate sulfonation products with a quenching reagent reactive with sulfur trioxide.
Inventors
- 👤 Marshall J. Nepras
- 👤 Peter F. Heid
- 👤 Matthew I. Levinson
- 👤 Randal J. Bernhardt
- 👤 James A. Hartlage
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 19:03
CPC Classifications
C; C07; C07C; C07C309/00; C07C309/01; C07C309/28; C07C309/41; C07C309/42
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
139 words
A method for preparing a p-phenyl sulfonic acid acyl glycolate of the formula ##STR13## where R represents branched or straight chain alkyl having 6-12 carbon atoms comprising the steps of: (a) treating a phenyl ester of the formula ##STR14## where R represents branched or straight chain alkyl having 6-12 carbon atoms with a sulfonating agent at a temperature of about -50° C. to about 50° C. to form intermediate sufonation products, where the ratio of sulfonating agent to phenyl ester is from about 1.1:1 to about 3:1. (b) transmuting the intermediate sulfonation products over a period of about 5 minutes to about 50 hours at a temperature of from about 0° C. to about 90° C. to produce transmuted intermediate sulfonation products; and (c) quenching the transmuted intermediate sulfonation products with a quench reagent reactive with the sulfonating agent.
Claim 2
Independent Claim
139 words
A method for preparing a p-phenyl sulfonic acid acyl glycolate of the formula ##STR13## where R represents branched or straight chain alkyl having 6-12 carbon atoms comprising the steps of: (a) treating a phenyl ester of the formula ##STR14## where R represents branched or straight chain alkyl having 6-12 carbon atoms with a sulfonating agent at a temperature of about -50° C. to about 50° C. to form intermediate sufonation products, where the ratio of sulfonating agent to phenyl ester is from about 1.1:1 to about 3:1. (b) transmuting the intermediate sulfonation products over a period of about 5 minutes to about 50 hours at a temperature of from about 0° C. to about 90° C. to produce transmuted intermediate sulfonation products; and (c) quenching the transmuted intermediate sulfonation products with a quench reagent reactive with the sulfonating agent.
Claim 3
Dependent Claim
39 words
A method according to claim 1, wherein the quenching of the transmuted intermediate products is over a period of from about 5 minutes to about 24 hours at a temperature of from about 0° C. to about 90° C.
Claim 4
Dependent Claim
12 words
A method according to claim 2, wherein the phenyl ester is ##STR15##
Claim 5
Dependent Claim
13 words
A method according to claim 3, wherein the sulfonating reagent is sulfur trioxide.
Claim 6
Dependent Claim
73 words
A method according to claim 4, wherein the phenyl ester is treated with sulfur trioxide in a solvent selected from the group consisting of sulfur dioxide, dioxane, dimethyl formamide, straight or branched chain hydrocarbons having 4-20 carbons, nitroparaffins, acetonitrile, chloroalkyls, carboxylic acids, straight or branched chain alkaryl sulfonate compounds having 1 to 18 alkyl carbon atoms, straight or branched chain alkaryl compounds having 1-18 alkyl carbon atoms, cumene, xylene, olefins and mixtures thereof.
Claim 7
Dependent Claim
30 words
A method according to claim 5, wherein the phenyl ester and solvent are present in a weight ratio of phenyl ester to solvent of from about 10:1 to about 1:10.
Claim 8
Dependent Claim
40 words
A method according to claim 6 ,wherein the quench reagent is selected from the group consisting of straight or branched chain alkaryl compounds having 1 to 18 alkyl carbon atoms, cumene, xylene, olefins, unsaturated esters, ammonia, amines and mixtures thereof.
Claim 9
Dependent Claim
26 words
A method according to claim 7, wherein the amount of quench reagent is from about 10% to about 1000% of the amount of sulfur trioxide utilized.
Claim 10
Dependent Claim
26 words
A method according to claim 8, wherein the phenyl ester is treated with sulfur trioxide at a temperature of from about -20° to about 5° C.
Claim 11
Dependent Claim
22 words
A method according to claim 9, wherein the transmuting step is over a period of about 20 minutes to about 4 hours.
Claim 12
Dependent Claim
22 words
A method according to claim 10, wherein the transmuting step is at a temperature of about 20° C. to about 40° C.
Claim 13
Dependent Claim
22 words
A method according to claim 11, wherein the quenching step is over a period of about 5 minutes to about 4 hours.
Claim 14
Dependent Claim
22 words
A method according to claim 12, wherein the quenching step is at a temperature of about 20° C. to about 40° C.
Claim 15
Dependent Claim
23 words
A method according to claim 13, wherein the molar ratio of sulfur trioxide to phenyl ester is from about 1.35:1 to about 1.75:1.
Claim 16
Dependent Claim
23 words
A method according to claim 14, wherein the molar ratio of sulfur trioxide to phenyl ester is from about 1.45:1 to about 1.65:1.
Claim 17
Dependent Claim
23 words
A method according to claim 15, wherein the molar ratio of quench reagent to sulfur trioxide excess is about 0.75:1 to about 0.95:1.
Claim 18
Dependent Claim
37 words
A method according to claim 1, further comprising: (a) neutralizing the sulfonic acid with a solution of a base having a cation selected from the group consisting of alkali metals, ammonium, organic ammonium cations and mixtures thereof.
Claim 19
Independent Claim
146 words
A method for preparing a p-phenyl sulfonic acid acyl glycolate of the formula ##STR16## where R represents branched or straight chain alkyl having 6-12 carbon atoms comprising the steps of: (a) treating a phenyl ester of the formula ##STR17## where R represents branches or straight chain alkyl having 6-12 carbon atoms with sulfur trioxide at a sulfur trioxide to phenyl ester molar ratio of 1.5:1 to form intermediate sulfonation products; (b) transmuting the intermediate sulfonation products for a period of about 3 to 4 hours at a temperature of about 30° C.; and (c) quenching the transmuted intermediate sulfonation products with a straight or branched chain alkaryl quench reagent having 1 to 18 alkyl carbon atoms at a molar ratio of quench reagent to sulfur trioxide excess of about 0.85:1 at a temperature of about 30° C. for a period of about 3 to 4 hours.
Claim 20
Independent Claim
146 words
A method for preparing a p-phenyl sulfonic acid acyl glycolate of the formula ##STR16## where R represents branched or straight chain alkyl having 6-12 carbon atoms comprising the steps of: (a) treating a phenyl ester of the formula ##STR17## where R represents branches or straight chain alkyl having 6-12 carbon atoms with sulfur trioxide at a sulfur trioxide to phenyl ester molar ratio of 1.5:1 to form intermediate sulfonation products; (b) transmuting the intermediate sulfonation products for a period of about 3 to 4 hours at a temperature of about 30° C.; and (c) quenching the transmuted intermediate sulfonation products with a straight or branched chain alkaryl quench reagent having 1 to 18 alkyl carbon atoms at a molar ratio of quench reagent to sulfur trioxide excess of about 0.85:1 at a temperature of about 30° C. for a period of about 3 to 4 hours.
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) | 1995-06-23 | 1995-12-23 | 1996-06-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-06-23 | 1999-12-23 | 2000-06-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-06-23 | 2003-12-23 | 2004-06-23 | $7700.00 | Window Closed / Lapsed |