Note: Descriptions are shown in the official language in which they were submitted.
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A condensa-tion product of glucose and sorbitol is recognized as a
bulking agent suitable for use in an admixture with formulated foods, such as
cakes, candy bases, preserves, puddings and the like. Bulking agents may be
used alone, but often are ernployed with low-calo-rie, high-intensity, artificial
s~eetener products, to render the bulking agent effective and generally as
sweet as sucrose.
United States Patent ~,02~,290 discloses the preparation of bulking
agents by the reaction o glucose and sorbitol in the presence of an acidic
ion-exchange resin, such as a sul~onated styrenedivinylbenzene resin. After
separation of the inedible ion-exchange resin, the major product produced is
glucosylsorbitol. The use of the ion-exchange resin requires purification
procedures, such as neutralization and separation steps, prior to the produc-
tion of the bulking agent. Typically, the use of strong acid, inorganic or
monocarboxylic acid results in an undesirable inedibIe reaction product.
United States Patent 3,766,165 relates to the preparation of poly-
merized polysaccharides in an anhydrous melt polymerization process employing
edible acids as catalysts and cross-linking agents. The polymerized glucose-
sorbitol polymers produced are characteri7ed by high molecular weights; Eor
example, an average molecular weight oF 6,000 to 36,00a.
The present invention relates to a process ror the preparation
ot the condensation product of glucosylsorbitol and to the product so prepared
allcl the use ot the condensltion product as a foocl-bulking agc-~nt.
[t hCLS boen discoverecl that glucose and sorbitol, when reacted in
stoicllioTIletric e(luimoLIr arnoullts with heating preEerably under vacuum to remove
watc3r nnd in the presence ot ecliblc,~ nontoxic, nonvolatile cli or tri organic
carboxyLic acid or acid anhydrides as acid catalysts, provides glucosylsorbitol
1S the l~rirrllry reaction product. 'I'his process and reaction are unusual, since
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it would be expected that SUC}I reaction would provide a high-molecular-weight
glucose-based polymer.
The reaction product resembles sucrose in both texture and bulk.
The product is more hygroscopic than sugar and is tasteless. When used with
other high-intensity sweeteners, it may be incorporated in low-calorie food,
imparting texture~ bulk and appearance of regular food. Many materials have
been proposed for use in dietetic food for this purpose, but none of these
materials satisEy all of the requirements simultaneously.
Our process provides for the direct preparation of the dimer product
as the major product and avoids the difficulties associated with purification
steps to remove inedible acid catalysts.
The process is simply carried out under varying reaction times and
temperature conditions and typically at a temperature of from about 140C to
180C; for example, 150C to 170~C, and in reaction times of from 30 minutes to
3 hours; for example, 3~ minutes to 1 1/2 hours. I~ater may be removed by carry-
ing out the reaction under vacuum, preferably less than 20 inches of mercury.
The reaction is as follows:
CH2H CIH2H CH2}l O - C112
H - C - OH ~ o \ / }I - C - OH
~ OH ~ tlO - C - tl Di- or tri-~01-1 // }10 - C - H
Otl~ ~ 011 1-1 - C - OtlcarboxylicOH~ ~ ~ 1-1 - C - 0}1
11 - C - Otl Vacuum/l-leat~OH 11 - C - 01-1
Glucose l~l2oll 1l2 c~l2o~l
Sorbitol Glucosylsorbitol
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The reaction product produced is composed mainly of the di~er
glueosylsorbitol, with possible trimer amounts of the glucose-sorbitol polymer
and decomposition products of glucose.
The acid catalyst employecl may be a nonvolatile, edible, nontoxic
di or tricarboxylic acid or acid anhydride; for example, C2-C6 organic acids.
Typical acid catalysts include, but are not limited to: citric acid, lactic
acid, fumaric acid, tannic acid, tartaric acid or acid salts thereof, or adipic
acid ~ncl succinic acid anhydride may be used. The amount of the acid catalyst
may ~ary, but typically ranges from abou~ 0.05% to 5.0% by weight of the
glucose-sorbitol mixture; for example, 0.2% to 2.0%.
The process has typically been carried out as follows.
Equimolar quantities of sorbitol and glucose were weighed. Sorbitol
~as transferred in the reaction kettle and heated until it melted down to
~lowable liquid. 1% of total weight ~glucose and sorbitol) of di or tricar-
boxylic acid was added to sorbitol. The contents of the recLction kettle were
agitated for a few minutes. Glucose was then transferred to the kettle and
the temperature was raised to 270F. At this point, vacuum was applied. As
the temperature reached 300F, the reaction was stopped.
The above invention would be understood more fully in Light of the
~ollowing examples:
Example 1.
An intimate mixture oE equimolar quantities oF sorbitoL, g'lucose
(1 lb:l5.8 oz.) and 1% oE citric acid was placed in a vacuum kett'le. It was
hocltocl to 160C and vacuum ~30" of l-lg~ n~aintained Eor 1 hour. The product
obtailled was oE ligllt yellow color. Upon cooling, it set like a glass ancl was
hygroscopic.
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Example 2.
A charge of equimolar quantities of sorkitol and glucose was placed
in a vacuum kettle. The mixture was heated to 160C and 1% (weight o-f the
mixture) of tartaric acid was added to it. Temperature and vacuum (30") were
maintained for 1 hour. The reaction product was similar to that of Example l.
Example 3.
A preblend of equimolar quantities of sorbitol and glucose was
placed in a vacuum kettle. 1% of fumaric acid was addecl to the mixture and the
contents were he~ted to 160C. Temperature and vacuum (30") were maintained
for l hour. The reaction product was of light yellow color and had more un-
reacted sorbitol and glucose as compared to Examples 1 and 2.
Example ~.
An intimate ~ixture of 1 lb. of sorbitol and 15.8 oz. of glucose,
along with 0.32 oz. of succinic anhydride, was placed in a flask and melted
rapidly at a temperature of 16aC. The rapid heating is required in order to
minimize the loss of anhydride by sublimation The ~eaction mixture was held
at 160C and vacuum (30") for 1 hour. A light yellow product was obtained,
which was completely water-solukle.
