Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Reexamination Certificate
1999-06-10
2001-03-27
Carr, Deborah D. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
Reexamination Certificate
active
06207843
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
Salts of acyloxybenzenesulfonic acids are known for use as bleach activators in laundry detergents; see EPA 0 355 384 A1 and U.S. Pat. Nos. 5,534,642 and 5,414,099. As noted in the references cited hereinafter, various syntheses for such materials have been disclosed in the art. However, as can be seen from an inspection of these references, product yields are sub-optimal and the overall process can be complicated. As with any process which is conducted on a commercial scale, there is a continuing search for means to increase product yields and to otherwise facilitate plant operations. The present invention provides simple, yet effective, means for improving the process for manufacturing these bleach activator compounds.
BACKGROUND ART
U.S. Pat. No. 5,466,840 to Lutz, Zima and Bernard, issued Nov. 14, 1995; U.S. Pat. No. 5,391,780 to Zima and Williams, issued Feb. 21, 1995; U.S. Pat. No. 5,393,901 to Zima, Williams, Lutz and Dickason, issued Feb. 28, 1995; U.S. Pat. Nos. 5,393,905 to Zima. Williams and Shelton, issued Feb. 28. 1995; and 5,523,434 to Burns and Simpson, issued Jun. 4, 1996. all relate to various aspects of the synthesis and/or purification of compounds of the present type.
SUMMARY OF THE INVENTION
The present invention encompasses, in a process for preparing a sulfophenyl amido alkanoate by reacting acetoxy benzene sulfonate with an amido carboxylic acid, the improvement which comprises conducting the reaction in the presence of a tertiary amine.
The amido carboxylic acids used herein are 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 1 to about 8. In a highly preferred mode, the amido carboxylic acid is
The tertiary amines used herein are of the formula R
2
R
3
R
4
N, wherein substituents R
2
, R
3
and R
4
may be the same or different and are members selected from the group consisting of hydrocarbyl, e.g., C
1
-C
18
alkyl, alkenyl, branched or straight-chain, and alkoxy such as methoxy, ethoxy, propoxy, and the like, provided that any —OH substituents on the alkoxy substituents are capped with alkyl groups such as methyl. The substituents (e.g. R
2
and R
3
) may be cyclized to form a ring. Preferred amines include members selected from the group consisting of tris[2-(2-methoxyethoxy)ethyl]amine, N,N-dimethyldodecylamine, and imidazole. The process uses the amine in an amount ranging from at least about 0.1, preferably from about 0.3 to about 1.0, molar equivalent based on the amido acid reactant.
The invention also encompasses in a process for preparing a sulfophenyl amido alkanoate by reacting acetoxy benzene sulfonate with an amido carboxylic acid, the improvement which comprises conducting the reaction in the presence of an (non-amido carboxylic acid) amido solvent. Again, the amido carboxylic acid is of the formula shown above and is preferably
In this process, the preferred amido solvent has a boiling point of at least about 200° C. Most preferably, the amido solvent is free from N-H substituents. Such amido solvents include members selected from the group consisting of cyclic amides, N-substituted imides and urea derivatives. Examples of amido solvents useful herein include members selected from the group consisting of 1-cyclohexyl-2-pyrrolidinone, N-methylpyrrolidone, N-acetylmorpholine, and mixtures thereof.
In another aspect, the manufacturer may elect to use the amido solvent in combination with the amine catalyst.
All percentages, ratios and proportions disclosed herein are on a mole basis, unless otherwise specified. All documents cited are, in relevant part, incorporated herein by reference.
DETAILED DESCRIPTION OF THE INVENTION
As noted above, the use of the organic compounds which can be manufactured by the improved process disclosed herein as bleach activators is known and forms no part of the present invention. Rather, the invention herein relates to an improvement in the process for manufacturing said compounds.
The invention herein comprises two aspects, and, optionally, combinations thereof In one aspect, key steps of the process are conducted in the presence of amine compounds, preferably tertiary amines, which substantially improve the yield of the desired end product. These amines seem to act as a “catalyst”, inasmuch as they substantially increase product yields. However, they are typically used in higher proportions than one might expect for conventional “catalysts”. Thus, it may be speculated that these amines actually function to modify the phase behavior of the reactants used in the process, thereby providing improved solubility/reactivity of the reactants. Or, it may be speculated that the amines function as a transacylation catalyst (e.g., imidazole). Whatever the reason for the improvement in the overall process, these amines may conveniently referred to as “phase transfer catalysts”.
In another aspect, amido solvents are used in the reaction. These solvents provide reactant and product mixtures which are easier to work with on an industrial scale (i.e., improved processability) than the sulfur-containing solvents described in the above-cited references.
In another optional mode, combinations of the amido solvent and the amine “phase transfer catalyst” are used to improve the process, either with respect to overall product yields, overall processability, or both.
The details of a process for manufacturing preferred bleach activators such as the 4-[N-(alkanoyl)aminoalkanoyloxy]benzenesulfonate are described in U.S. Pat. No. 5,466,840 and the other patents cited above, all of which are incorporated herein by reference. Such patents can be readily referred to for experimental procedures such as reaction times, temperatures, handling techniques, purification steps, and the like.
As an overall proposition, the synthesis disclosed in this art, and which is the subject of the improved process herein, comprises the following reactions, which may be conducted in a single vessel without isolation of the ABS compound. In this regard, the reaction can comprise the joint admixture of the SPS, acetic anhydride and amido acid.
Thus the present invention comprises, in a process for preparing an N-(alkanoyl)aminoalkanoyloxy benzenesulfonate Product by reacting ABS with an amido carboxylic acid, the improvement which comprises conducting the reaction in the presence of a tertiary amine, or in the presence of an amido solvent, or both.
REFERENCES:
patent: 5391780 (1995-02-01), Zima et al.
patent: 5393901 (1995-02-01), Zima et al.
patent: 5393905 (1995-02-01), Zima et al.
patent: 5414099 (1995-05-01), Heinzman et al.
patent: 5466840 (1995-11-01), Lutz et al.
patent: 5523434 (1996-06-01), Burns et al.
patent: 5534642 (1996-07-01), Heinzman et al.
Dupont Jeffrey Scott
Heinzman Stephen Wayne
Carr Deborah D.
Cook C. Brant
Miller Steven W.
The Procter & Gamble & Company
William Zerby Kim
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