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US 5,288,884 AGranted
Process for producing a reduced calorie fat mimetic composition
AssigneesArco Chemical Technology, L.P., CPC International Inc.
InventorCharles F. Cooper
Life of this patent
Estimating the term…
Abstract
A convenient method of obtaining a reduced calorie esterified alkoxylated polyol containing both long chain saturated linear acyl groups and shorter chain unsaturated acyl groups is provided.
Claims20
A process for producing a reduced calorie fat mimetic comprising the steps of
- (a) contacting a first esterified alkoxylated polyol characterized by the presence of at least one C.sub.20 -C.sub.24 unsaturated linear acyl group 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 any C.sub.22 unsaturated linear acyl group;
- and
- (b) contacting the second esterified alkoxylated polyol 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 at least one C.sub.20 -C.sub.24 saturated linear acyl group and at least one C.sub.6 -C.sub.19 unsaturated acyl group to yield the reduced calorie fat mimetic.
A process for producing a reduced calorie fat mimetic composition comprising the steps of
- (a) contacting a first esterified alkoxylated polyol comprised of (i) a first polyol residue derived from a first polyhydric aliphatic compound and (ii) 2 to 8 fatty acid-esterified oxyalkylene groups connected to said first polyol residue wherein at least one-half of the fatty acid-esterified oxyalkylene groups have the general structure ##STR17## wherein OA.sup.1 is a first oxyalkylene unit derived from a first C.sub.2 -C.sub.10 aliphatic epoxide, n is from 1 to 20, and ##STR18## is an acyl group derived from a C.sub.20 -C.sub.24 unsaturated linear fatty acid with hydrogen in the presence of a catalyst containing nickel or copper at a pressure of from 0.5 to 20 atmospheres and a temperature of from 75.degree. C. to 275.degree. C. for a time effective to accomplish hydrogenation of the acyl group derived from the C.sub.20 -C.sub.24 unsaturated linear fatty acid 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 any C.sub.22 unsaturated linear acyl groups;
- and
- b) contacting the second esterified alkoxylated polyol with a third esterified alkoxylated polyol comprised of (i) a second polyol residue which is the same as or different from the first polyol residue derived from a second polyhydric aliphatic compound which is the same as or different from the first polyhydric aliphatic compound and (ii) from 2 to 8 fatty acid-esterified oxyalkylene groups connected to said second polyol residue wherein at least one of the fatty acid-esterified oxyalkylene groups has the general structure ##STR19## wherein OA.sup.2 is a second oxyalkylene unit derived from a second C.sub.2 -C.sub.10 aliphatic epoxide which may be the same as or different from the first C.sub.2 -C.sub.10 aliphatic epoxide, m is from 1 to 20, and ##STR20## is an acyl group derived from a C.sub.6 -C.sub.19 unsaturated fatty acid in the presence of an alkali metal or alkali metal compound at a temperature of from 0.degree. C. to 275.degree. C. for a time effective to accomplish interchange of at least one C.sub.20 -C.sub.24 saturated linear acyl group in the second esterified alkoxylated polyol and at least one acyl group derived from a C.sub.6 -C.sub.19 unsaturated fatty acid in the third esterified alkoxylated polyol to yield the reduced calorie fat mimetic composition.
Dependencies are inferred from the claim text.