Process for producing a reduced calorie fat mimetic composition

Reference Number: N 04-04

Inventors: Cooper, Charles F.

Owner: NISTAC

USPTO Link: 5288884

Invention Summary

This invention provides a process for producing a reduced calorie fat mimetic composition comprising the steps of contacting a first esterified alkoxylated polyol characterized by the presence of C.sub.20 -C.sub.24 unsaturated linear acyl groups with hydrogen in the presence of a transition metal catalyst for a time and at a temperature effective to accomplish hydrogenation of the C.sub.20 -C.sub.24 unsaturated linear acyl group to yield a second esterified alkoxylated polyol characterized by the presence of at least one C.sub.20 -C.sub.24 saturated linear acyl group and the absence of C.sub.22 unsaturated linear acyl groups. The second esterified alkoxylated polyol is contacted with a third esterified alkoxylated polyol characterized by the presence of at least one C.sub.6 -C.sub.19 unsaturated acyl group in the presence of a basic catalyst for a time and at a temperature effective to accomplish interchange of the C.sub.20 -C.sub.24 saturated linear acyl group and the C.sub.6 -C.sub.19 unsaturated acyl group to yield the reduced calorie fat mimetic composition.

The incorporation of C.sub.20 -C.sub.24 saturated linear acyl groups into the final esterified alkoxylated polyol at high levels renders it better tolerated in the digestive tract, as described in the aforementioned copending application. At any level, however, C.sub.20 -C.sub.24 saturated linear acyl groups have the beneficial effect of increasing the melting or solidification point of an esterified alkoxylated polyol. This increase in melting point may be utilized to help counteract the effect of introducing higher proportions of oxyalkylene groups in an esterified alkoxylated polyol. That is, an increasing degree of propoxylation (moles of propylene oxide reacted per mole of polyol) tends to enhance the non-digestibility and lower the available caloric content of an esterified alkoxylated polyol but also generally depresses the melting point of such a composition. The solid fat index of the substance at a given temperature may consequently be too low for the substance to be directly substitutable for a conventional high-melting triglyceride in a margarine, shortening, cheese, or hard butter (confectionary) application. Increasing the proportion of C.sub.20 -C.sub.24 saturated linear acyl groups relative to shorter chain, branched, and/or unsaturated acyl groups will favorably affect the melting characteristics of such substances. Another benefit of introducing C.sub.20 -C.sub.24 linear acyl groups into an esterified alkoxylated polyol is that the caloric availability of the fat mimetic tends to be lower when such groups are present rather than shorter chain acyl groups.

A distinct advantage of the present invention is that it completely avoids the use of free C.sub.20 -C.sub.24 saturated linear fatty acids in a direct esterification step, thereby minimizing the handling and processing problems which are otherwise encountered. Another advantage is that the relative proportion of shorter chain unsaturated acyl groups in the esterified alkoxylated polyol composition may be varied as desired without introducing possible harmful levels of acyl groups derived from erucic acid.