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US4692279A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of acyloxy benzene sulfonate

Assignee: Stepan Co
•
Filing: 1985-04-15
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Granted: 1987-09-08
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Expires: 2005-04-15
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Abstract

Abstract A process is provided for making acyloxy benzene sulfonates by the steps of sulfonating with SO 3 , digesting the sulfonation adduct, and neutralizing. The sulfonation adduct can spontaneously rearrange. Unless the rearrangement is controlled as taught in the sulfonating and digesting steps, product yields of acyloxy benzene sulfonate drop to unusable levels and the color of the product is poor and the content of by-products is excessive in the product.

Inventors

  • 👤 Marvin Nussbaum

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 21:43
CPC Classifications
C; C07; C07C; C07C303/00; C07C303/02; C07C303/04; C07C303/06; C07C309/00; C07C309/01; C07C309/28; C07C309/41; C07C309/42

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 172 words
A process for making an acyloxy benzene sulfonate salt of at least about 80 weight percent purity on a total composition dry weight basis from a corresponding acyloxy benzene comprising the steps of (a) contacting substantially pure acyloxy benzene with SO 3 at a temperature ranging from about -20° to 50° C. to produce an intermediate reaction product which comprises about a 1:1 molar adduct of said SO 3 and said acyloxy benzene, (b) maintaining said intermediate reaction product at an average temperature in the range from about 25° to 75° C. for a time inversely ranging from about 0.1 to 4 hours sufficient to produce a product composition containing at least about 80 weight percent of the corresponding acyloxy benzene sulfonic acid, and (c) admixing the resulting said acyloxy benzene sulfonic acid with an aqueous solution of a base of a cation selected from the group consisting of alkali metal salts, alkaline earth metals, and ammonium to produce an aqueous solution containing the corresponding salt of said acyloxy benzene sulfonic acid.
Claim 2
Dependent Claim 172 words
A process for making an acyloxy benzene sulfonate salt of at least about 80 weight percent purity on a total composition dry weight basis from a corresponding acyloxy benzene comprising the steps of (a) contacting substantially pure acyloxy benzene with SO 3 at a temperature ranging from about -20° to 50° C. to produce an intermediate reaction product which comprises about a 1:1 molar adduct of said SO 3 and said acyloxy benzene, (b) maintaining said intermediate reaction product at an average temperature in the range from about 25° to 75° C. for a time inversely ranging from about 0.1 to 4 hours sufficient to produce a product composition containing at least about 80 weight percent of the corresponding acyloxy benzene sulfonic acid, and (c) admixing the resulting said acyloxy benzene sulfonic acid with an aqueous solution of a base of a cation selected from the group consisting of alkali metal salts, alkaline earth metals, and ammonium to produce an aqueous solution containing the corresponding salt of said acyloxy benzene sulfonic acid.
Claim 3
Dependent Claim 29 words
The process of claim 1 wherein said acyloxy benzene is cahracterized by the formula: ##STR3## where R is a saturated aliphatic group containing from 2 through 19 carbon atoms.
Claim 4
Dependent Claim 43 words
The process of claim 2 wherein said sulfonation is carried out in a zone wherein the average temperature ranges from about -30° to +50° C., and the mole ratio of said SO 3 to said acyloxy benzene ranges from about 0.9:1 to 1.1:1.
Claim 5
Dependent Claim 22 words
The process of claim 2 wherein each said aliphatic group is an alkyl group which contains from 7 through 11 carbon atoms.
Claim 6
Dependent Claim 21 words
The process of claim 2 wherein said contacting is carried out in a liquid phase in the presence of a diluent.
Claim 7
Dependent Claim 19 words
The process of claim 5 wherein said contacting is carried out with said acyloxybenzene being in a liquid state.
Claim 8
Dependent Claim 22 words
The process of claim 1 wherein said digesting is carried out at an average temperature ranging from about 40° to 75° C.
Claim 9
Dependent Claim 28 words
The process of claim 1 wherein said admixing is carried out continuously and the product neutralized solution has a pH in the range from about 4.5 to 7.
Claim 10
Dependent Claim 46 words
The process of claim 1 wherein the final product solution has a pH ranging from about 3 to 8 and wherein the concentration of said salt of said acyloxy benzene sulfonic acid ranges from about 5 to 60 weight percent based on total aqueous solution weight.
Claim 11
Dependent Claim 180 words
A process for making an acyloxy benzene sulfonate salt which has an APHA color that is less that about 100 comprising the steps of sequentially: (A) contacting SO 3 with at least one acyloxybenzene of the formula: ##EQU1## where R is a saturated aliphatic group containing from about 2 to 19 carbon atoms inclusive under liquid phase conditions in the presence of a substantially inert liquid to produce a reaction product wherein the combined mole ratio of SO 3 to acyloxybenzene ranges from about 0.9 to 1.1, (B) evaporating said inert liquid from said reaction product at a rate sufficient to maintain said reaction product at a temperature from about -10° to 15° C. (C) maintaining said resulting reaction product at a temperature in the range from about 10° to 75° C. for a time inversely ranging from about 0.1 to about 4 hours until said reaction product has been substantially completely rearranged, thereby to produce acyloxybenzene sulfonic acid, and (D) admixing said acid with dilute aqueous base solution under liquid phase conditions at a temperature below about 35° C.
Claim 12
Dependent Claim 180 words
A process for making an acyloxy benzene sulfonate salt which has an APHA color that is less that about 100 comprising the steps of sequentially: (A) contacting SO 3 with at least one acyloxybenzene of the formula: ##EQU1## where R is a saturated aliphatic group containing from about 2 to 19 carbon atoms inclusive under liquid phase conditions in the presence of a substantially inert liquid to produce a reaction product wherein the combined mole ratio of SO 3 to acyloxybenzene ranges from about 0.9 to 1.1, (B) evaporating said inert liquid from said reaction product at a rate sufficient to maintain said reaction product at a temperature from about -10° to 15° C. (C) maintaining said resulting reaction product at a temperature in the range from about 10° to 75° C. for a time inversely ranging from about 0.1 to about 4 hours until said reaction product has been substantially completely rearranged, thereby to produce acyloxybenzene sulfonic acid, and (D) admixing said acid with dilute aqueous base solution under liquid phase conditions at a temperature below about 35° C.
Claim 13
Dependent Claim 43 words
The process of claim 10 wherein said acyloxybenzene sulfonic acid is dissolved in water under liquid phase conditions at a temperature below about 5° C. to produce a dilute aqueous acid solution and said solution is then so admixed with said base solution.
Claim 14
Dependent Claim 13 words
The process of claim 10 wherein said resulting mixed slurry is spray dried.
Claim 15
Dependent Claim 70 words
In a sulfonation process for making a sulfonated salt by sulfonating with SO 3 and neutralizing, the improvement which comprises reacting an acyloxy benzene with SO 3 at low temperatures followed by a controlled rearrangement step between said sulfonating and said neutrualizing, said controlled rearrangement step comprising maintaining the sulfonation reaction product at a temperature of from about 15° to 75° C. until said reaction product is substantially completely rearranged.
Claim 16
Dependent Claim 70 words
In a sulfonation process for making a sulfonated salt by sulfonating with SO 3 and neutralizing, the improvement which comprises reacting an acyloxy benzene with SO 3 at low temperatures followed by a controlled rearrangement step between said sulfonating and said neutrualizing, said controlled rearrangement step comprising maintaining the sulfonation reaction product at a temperature of from about 15° to 75° C. until said reaction product is substantially completely rearranged.

References Cited (Backward Citations)

CA545620A Cited
US3169142A Cited
US3358017A Cited
US4148821A Cited
US4390474A Cited
US4588533A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-09-07 1991-03-09 1991-09-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-09-07 1995-03-09 1995-09-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-09-07 1999-03-09 1999-09-08 $7700.00 Window Closed / Lapsed

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