Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2001-02-26
2002-07-23
Killos, Paul J. (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C560S198000, C560S204000, C560S302000, C560S190000, C562S002000, C562S006000, C510S367000, C510S375000, C510S376000
Reexamination Certificate
active
06423868
ABSTRACT:
The present invention is related to a process for the production of an aqueous monoester peroxycarboxylic acid solution. It also concerns the aqueous monoester peroxycarboxylic acid solution obtainable by this process and its use in disinfectant compositions.
Compositions containing monoester percarboxylic acids and their preparation by reaction between a monoester of an aliphatic dicarboxylic acid and hydrogen peroxide have been described in the international patent application WO 95/34537 to SOLVAY INTEROX LIMITED. Such compositions were shown to have no discernible odour and to be effective as microbicide. Although the compositions exhibited a level of available oxygen stability that would enable them to remain effective during several months storage, there is a continuing need to find new solutions of monoester percarboxylic acids.
It is an object of the invention to provide a new or alternative process for the production of monoester peroxycarboxylic acid solutions as well as to provide new monoester peroxycarboxylic acid solutions.
Consequently, the present invention concerns a process for the production of an aqueous monoester peroxycarboxylic acid solution by reaction of a peroxygen compound with at least one polycarboxylic acid and with at least one alcohol optionally in the presence of an acid catalyst. Preferably, the polycarboxylic acid is a dicarboxylic acid. While focused on this preferred embodiment, the present invention is however not limited thereto.
One of the essential characteristics of the process of the invention resides in the nature of the starting materials especially the dicarboxylic acid and the alcohol which render the process particularly performing. Indeed, by using these starting materials new solutions can be produced. It will be recognised that a complex mixture will be obtained using the process according to the invention containing the desired monoester peroxycarboxylic acid (called ester peracid hereafter), water, and may also contain residual amounts of non consumed dicarboxylic acid (called diacid hereafter), peroxygen compound, alcohol and optional acid catalyst, and in situ generated corresponding diester, monoester carboxylic acid, monocarboxylic peroxycarboxylic acid and diperoxycarboxylic acid. The advantage of the process of the invention resides in the possibility to control the relative amounts of the desired ester peracid to all the other products generated in situ. Indeed, by varying the amount of alcohol in the reaction mixture, more or less of the ester peracid will be produced relative to the amount of other products. So, a large variety of solutions can be obtained using a single process.
Another advantage resulting from the nature of the stating materials resides in the duration of the process. Indeed, the diacids used as starting material in the present invention have generally a higher solubility in the reaction mixture than have monoesters of dicarboxylic acids which are used in the known process described in the international patent application WO 95/34537. The higher solubility results in faster dissolution rates and thus shorter production times.
Yet another advantage of the process of the invention resides in the availability of the stating materials. Indeed, diacids and alcohols are more readily available than monoesters of a dicarboxylic acid.
Yet another advantage of the process of the present invention resides in the large choice of the organic radical of the ester group. Indeed, in the known process of the international patent application WO 95134537 the choice of the organic radical of the ester group is determined by the choice of the monoester of a dicarboxylic acid used as starting material whereas in the present invention the organic radical of the ester group originates from the alcohol It is clear that in the process of the invention alcohols can be used which are not available as monoesters.
The diacid used in the process of the invention can be chosen from any compound containing at least two carboxylic acid groups and which is capable of being transformed in an ester peracid in the process of the invention. The diacid can contain up to 20 carbon atoms, preferably up to 10 carbon atoms. The principal chain of the diacid which is substituted by the two carboxylic groups can be linear, branched, cyclic or aromatic, optionally unsaturated and or containing a heteroatom. Oxalic acid is convenient. Diacids with a linear principal chain generally corresponding to the formula COOH—R—COOH in which R is an alkylene group containing up to 6 carbon atoms can also be used. Suitable examples are adipic acid, glutaric acid and succinic acid. Examples of diacids with a branched principal chain are methyl succinic and ethyl malonic acids. Other examples are maleic, fumaric and maleic acids. The preferred diacids are adipic, glutaric and succinic acids. A mixture of two or more different diacids can be used in the process of the invention.
The diacid is generally used in an amount of at least 0,05% wt of the reaction mixture, preferably at least 5% wt The amount of diacid used is usually at most 65% wt in particular at most 25% wt. Quantities from 0,05 to 65% wt of diacid are convenient.
The peroxygen compound used in the process according to the invention can be chosen from hydrogen peroxide or any other peroxygen compound capable of releasing hydrogen peroxide in the reaction mixture of the process of the present invention. The expression “reaction mixture of the process of the invention” means a mixture containing water, the diacid, the alcohol, the peroxygen compound, optionally the acid catalyst, the ester peracid, the corresponding diester, monoester carboxylic acid, monocarboxylic peroxycarboxylic acid and diperoxycarboxylic acid. In particular, the peroxygen compound can be chosen from hydrogen peroxide, inorganic peracids, organic peracids and persalts. An example of inorganic peracid is Caro's acid. Organic acids containing up to 10 carbon atoms are convenient. An example of such an organic peracid is peracetic acid. Examples of persalts are sodium percarbonate and sodium perborate mono- or tetrahydrate. Hydrogen peroxide is preferred.
The peroxygen compound is generally used in an amount of at least 0,01% wt of the reaction mixture, in particular at least 5% wt. The amount of peroxygen compound used is usually at most 30% wt of the reaction mixture, preferably at most 25% wt. Quantities of peroxygen compound from 0,05 to 30% wt are convenient. When hydrogen peroxide is used, it can be added to the reaction mixture in the form of an aqueous solution containing from 1 to 85% wt of hydrogen peroxide. The molar ratio of the peroxygen compound to the diacid can be varied in a wide range. Generally this molar ratio is at least 0,1:1, preferably at least 1:1. The molar ratio is usually at most 35:1, in particular at most 7:1.
The alcohol used in the process of the invention can be chosen from any compound containing at least one hydroxyl group. Monoalcohols containing up to 20 carbon atoms are suitable, those containing up to 10 carbon atoms are preferred. Examples of suitable monoalcohols are methanol and ethanol. Diols containing up to 20 carbon atoms, preferably up to 10 carbon atoms can also be used. Examples of suitable diols are ethylene glycol and propylene glycoL. Polyols containing up to 20 carbon atoms can also be used. Examples of suitable polyols include sorbitol and mannitol. Alcohol ethoxylates could also be used. A mixture of two or more different alcohols can be used in the process of the invention.
The alcohol is generally used in an amount of at least 0,01% wt of the reaction mixture, in particular of at least 2% wt. The amount of alcohol used is usually at most 45% wt. more particularly at most 25% wt Quantities of alcohol from 0,05 to 45% wt are convenient. The molar ratio of the alcohol to the diacid can be varied within a wide range. Generally the ratio is at least 0,1:1, preferably at least 0,5:1. The molar ratio is usually at most 10:1, in particular at most 1:1.
The acid catalyst optio
Carr Graham
James Alun P.
Forohar Farhad
Killos Paul J.
Larson & Taylor PLC
Solvay ( Societe Anonyme)
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