Method for synthesizing acyloxycarboxylic acids

Reference Number: N 03-07

Inventors: Rowland, Richard R

Owner: NISTAC

USPTO Link: 5091560

Invention Summary

It is an object of the present invention to provide a method for synthesizing acyloxycarboxylic acids simply and in high yields, which acids are usefully converted to alkanoyloxyperacetic acids via ester precursors.

In one aspect of the present invention, a method for synthesizing an acyloxycarboxylic acid, useful as a starting material for conversion to various esters, comprises providing a reaction chamber, establishing sources of an .alpha.-hydroxycarboxylic acid and an acid chloride, and repeatedly contacting substantially equimolar amounts of the o-hydroxycarboxylic acid and the acid chloride within the reaction chamber. The sources of .alpha.-hydroxycarboxylic acid and acid chloride are separated from one another, and are preferably repeatedly contacted at a predetermined, relatively slow rate within the reaction chamber. However, if the mixture within the reaction chamber is sufficiently agitated and cooled, then the .alpha.-hydroxycarboxylic acid and acid chloride reactants can be contacted at relatively rapid rates.

The reaction chamber includes a basic component in an effective amount to neutralize a hydrogen chloride by-product during formation of the reaction product. The reaction product of this method is typically isolatable as at least about 65% of theoretical yield and has the structure ##STR1## wherein R.sub.1 is an alkyl group having two to about twelve carbon atoms, and R.sub.2 is hydrogen, methyl, ethyl, or propyl and R.sub.3 is hydrogen, methyl, ethyl, propyl, and substituted or unsubstituted phenyl or benzyl.

In another aspect of the present invention, the just described reaction product, whether isolated or not, is converted to an ester which, when placed in aqueous solution with a source of hydrogen peroxide, results in a peracid having the structure (where R.sub.1, R.sub.2 and R.sub.3 are as previously described).