Synthesis of bleach activators

Details Synthesis of bleach activators Synthesis of bleach activators

2001-05-07

2003-06-24

Delcotto, Gregory (Department: 1751)

Cleaning compositions for solid surfaces, auxiliary compositions

Cleaning compositions or processes of preparing

For cleaning a specific substrate or removing a specific...

C510S376000, C510S501000, C554S068000, C554S070000, C252S186380

Reexamination Certificate

active

06583095

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to an improved process for synthesizing organic compounds for use as bleach activators.
BACKGROUND OF THE INVENTION
The synthesis of ingredients for use in low unit cost consumer goods such as laundry detergents, fabric softeners, and the like is of considerable interest to manufacturers. Indeed, the low cost synthesis of ingredients is typically the rate limiting step in the course of bringing a consumer product to the market. Due to the large number of ingredients in consumer goods such as laundry detergents, the expense of individual ingredients must be minimized in order to keep the cumulative product cost within acceptable ranges. The expense associated with the manufacture of consumer goods ingredients is often due to either the cost of the raw materials used to make such ingredients or to the complex reaction and processing chemistry which is required in their manufacture. Accordingly, manufacturers conduct a continuing search for both inexpensive raw materials or simplified reaction sequences.
Amido acid phenyl ester sulfonates form a class of materials which can serve as bleach activators in laundry detergents and other types of bleach-containing cleaning compositions. Such activators have several desirable attributes including excellent bleaching performance with minimal color damage on fabrics dyes, good washing machine compatibility and a good odor profile in the wash. While these materials are potentially obtainable from inexpensive raw materials, the synthesis is somewhat complicated and typically involves the use of solvents. Problems can also arise in the formation of color impurities, caused by the reaction of color forming bodies, in the end product. These color forming impurities or bodies result in a finished product which is undesirable to consumers and consequently unusable because of its appearance. This results in additional steps to remove the colored impurities. These additional steps have the problem that not only do they remove the colored impurities, add additional time and cost, but they also remove some of the amido acid phenyl ester sulfonates along with the colored impurities. Thus, the synthesis of amido acid phenyl ester sulfonates is not straightforward and can be surprisingly problematic.
Accordingly, the need remains for a simple, inexpensive yet effective process for the production of amido acid phenyl ester sulfonates which does not result in the formation of colored impurities in the final product.
BACKGROUND ART
U.S. Pat. Nos. 5,466,840, 5,391,780, 5,393,901, 5,393,905, 5,523,434, 5,391,780, 5,414,099, 5,534,642, 5,153,541, 5,650,527, 5,286,879 and 5,523,434.
SUMMARY OF THE INVENTION
This need is met by the present invention, wherein improved process for preparing a purified amido acid phenyl ester sulfonate are provided.
According to a first aspect of the present invention, a process for the preparation a 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate is provided. The process comprises the steps of:
reacting an acetoxy benzene sulfonate salt with a high purity amido carboxylic acid, wherein said high purity amido carboxylic acid comprises least about 90%, preferably about 95%, even more preferably about 97% by weight, of a amido carboxylic acid of the formula:
 wherein R is C
5
-C
21
hydrocarbyl, R
1
is selected from hydrogen and C
1
-C
3
alkyl, and n is an integer from about 1 to about 8; and less than about 10% by weight, of color forming bodies;
wherein the process is performed in the presence of less than about 10 ppm, preferably less than about 5 ppm, more preferably less than about 2 ppm, even more preferably less than about 0.5 ppm of transition metals, preferably selected from the group consisting of iron, nickel, chromium and mixtures thereof, more preferably iron, nickel, and mixtures thereof
According to a second aspect of the present invention, the process for preparing a 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate comprising the steps of:
(a) reacting a high purity amido carboxylic acid, wherein said high purity amido carboxylic acid comprises least about 90%, preferably about 95%, even more preferably about 97% by weight, of an amido carboxylic acid of the formula:
 wherein R is C
5
-C
21
hydrocarbyl, R
1
is selected from hydrogen and C
1
-C
3
alkyl, and n is an integer from about 1 to about 8, M is H or an alkali metal salt; and less than about 10% by weight of color forming bodies;
 wherein the process is performed in the presence of less than about 10 ppm, preferably less than about 5 ppm, more preferably less than about 2 ppm, even more preferably less than about 0.5 ppm of transition metals, preferably selected from the group consisting of iron, nickel, chromium and mixtures thereof, more preferably iron, nickel, and mixtures thereof, with an acid halide to prepare the corresponding amido acid halide; and
(b) reacting the amido acid chloride of step (a) with a phenolsulfonate salt.
According to a third aspect to provide 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate when prepared according to either the first or second aspect of the present invention.
According to a fourth aspect to provide cleaning compositions comprising 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate prepared according to either the first or second aspect of the present invention.
Accordingly, it is an aspect of the present invention to provide a process for preparing a 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate. It is yet another aspect of the present invention to provide flexibility to a process for preparing a 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate. These, and other aspects, features and advantages of the present invention will be recognizable to one of ordinary skill in the art from the following description and the appended claims.
All percentages, ratios and proportions herein are on a weight basis unless otherwise indicated. All documents cited herein are hereby incorporated by reference.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The process of the present invention for preparing amido acid phenyl ester sulfonates involves as an important feature limiting the amount of transition metals and color forming bodies present in the process. As earlier noted, it is the reduction of the transition metals and color forming bodies content in the process which leads to the benefits and advantages of the present invention.
According to a first aspect of the present invention, a process for the preparation a 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate is provided. The process comprises the steps of:
reacting an acetoxy benzene sulfonate salt with a high purity amido carboxylic acid, wherein said high purity amido carboxylic acid comprises least about 90%, preferably about 95%, even more preferably about 97% by weight, of a amido carboxylic acid of the formula:
 wherein R is C
5
-C
21
hydrocarbyl, preferably C
5
-C
14
hydrocarbyl, more preferably C
6
-C
12
alkyl, C
6
-C
12
alkenyl, even more preferably C
6
-C
10
alkyl, R
1
is selected from hydrogen and C
1
-C
3
alkyl, preferably H, methyl, more preferably methyl, and n is an integer from about 1 to about 8; preferably an integer from about 2 to about 7, more preferably an integer from about 3 to about 6 and less than about 10%, preferably less than about 5%, more preferably less than about 2%, even more preferably less than about 1% by weight, of color forming bodies;
wherein the process is performed in the presence of less than about 10 ppm, preferably less than about 5 ppm, more preferably less than about 2 ppm, even more preferably less than about 0.5 ppm of transition metals, preferably selected from the group consisting of iron, nickel, chromium and mixtures thereof, more preferably iron, nickel, and mixtures thereof.
It is preferred that the high purity amido carboxylic acid comprises least about 95%, more preferably 97%, of a amido carboxylic acid of the formula:
The total impurities indicated above negatively influence

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