CA1179334A - Process for the manufacture of glucosylsorbitol - Google Patents
Process for the manufacture of glucosylsorbitolInfo
- Publication number
- CA1179334A CA1179334A CA000375552A CA375552A CA1179334A CA 1179334 A CA1179334 A CA 1179334A CA 000375552 A CA000375552 A CA 000375552A CA 375552 A CA375552 A CA 375552A CA 1179334 A CA1179334 A CA 1179334A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- glucosylsorbitol
- food
- glucose
- bulking agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- SERLAGPUMNYUCK-YJOKQAJESA-N 6-O-alpha-D-glucopyranosyl-D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SERLAGPUMNYUCK-YJOKQAJESA-N 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 20
- 239000008103 glucose Substances 0.000 claims abstract description 20
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims abstract description 17
- 239000000600 sorbitol Substances 0.000 claims abstract description 17
- 239000003377 acid catalyst Substances 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 13
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims abstract description 12
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims abstract description 12
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 8
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 8
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 235000019843 food bulking agent Nutrition 0.000 claims abstract 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 12
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 5
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
- 235000013305 food Nutrition 0.000 claims description 4
- 239000001530 fumaric acid Substances 0.000 claims description 4
- 235000002906 tartaric acid Nutrition 0.000 claims description 4
- 239000011975 tartaric acid Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- 239000001263 FEMA 3042 Substances 0.000 claims description 3
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims description 3
- 235000015165 citric acid Nutrition 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 235000011087 fumaric acid Nutrition 0.000 claims description 3
- LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052753 mercury Inorganic materials 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims description 3
- 235000015523 tannic acid Nutrition 0.000 claims description 3
- 229920002258 tannic acid Polymers 0.000 claims description 3
- 229940033123 tannic acid Drugs 0.000 claims description 3
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 3
- 239000013638 trimer Substances 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- JPSKCQCQZUGWNM-UHFFFAOYSA-N 2,7-Oxepanedione Chemical compound O=C1CCCCC(=O)O1 JPSKCQCQZUGWNM-UHFFFAOYSA-N 0.000 claims 2
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000004067 bulking agent Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- LTSFKYMMVSEWPP-NYRIJBPWSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O LTSFKYMMVSEWPP-NYRIJBPWSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 235000014105 formulated food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000008123 high-intensity sweetener Substances 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
A process of preparing glucosylsorbitol suitable for direct use as a food-bulking agent, which process consists essentially of heating equi-molar quantities of a mixture of glucose and sorbitol under vacuum in the presence of an effective amount of a nontoxic, edible di or tri carboxylic acid or acid anhydride as an acid catalyst, to provide a nontoxic, edible mixture containing glucosylsorbitol as a major component thereof.
A process of preparing glucosylsorbitol suitable for direct use as a food-bulking agent, which process consists essentially of heating equi-molar quantities of a mixture of glucose and sorbitol under vacuum in the presence of an effective amount of a nontoxic, edible di or tri carboxylic acid or acid anhydride as an acid catalyst, to provide a nontoxic, edible mixture containing glucosylsorbitol as a major component thereof.
Description
33~
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 ~L~79~3~
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 ~L~33~
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.
'9' 33~
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.
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 ~L~79~3~
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 ~L~33~
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.
'9' 33~
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.
Claims (11)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process of preparing glucosylsorbitol suitable for direct use as a food-bulking agent, which process consists essentially of heating equimolar quantities of a mixture of glucose and sorbitol under vacuum in the presence of an effective amount of a nontoxic, edible, di or tri carboxylic acid or acid anhydride as an acid catalyst) to provide a nontoxic, edible mixture containing glucosylsorbitol as a major component thereof.
2. The process of claim 1 wherein the acid catalyst is present in an amount of from about 0.05% to 5.0% by weight of the glucose and sorbitol.
3. The process of claim 1 wherein the mixture is heated to a temperature of about 140°C to 200°C and under a vacuum greater than about 20 inches of mercury.
4. The process of claim 1 wherein the acid catalyst comprises a C2-C6 di or tri carboxylic organic acid or acid anhydride.
5. The process of claim 1 wherein the acid catalyst is selected from the group consisting of citric acid, tartaric acid, fumaric acid, lactic acid, tannic acid, succinic acid anhydride and adipic acid anhydride and combinations thereof.
6. The process of claim 1 which includes directly employing the reaction product of glucosylsorbitol as a food-bulking agent in a food composition.
7. A food bulking agent containing glucosylsorbitol as a major amount in admixture with trimer glucosylsorbitol polymer or decomposition products of glucose or both, which food-bulking agent is produced by the process of claim 1.
8. A process of preparing glycosylsorbitol suitable for direct use as a food-bulking agent, which process consists essentially of heating equimolar quantities of a mixture of glucose and sorbitol heated to a temperature of about 140°C to 200°C and under a vacuum greater than about 20 inches of mercury in the presence of an effective amount of a nontoxic, edible, di or tri C2-C6 organic carboxylic acid or acid anhydride as an acid catalyst present in an amount of from about 0.05% to 5.0%
by weight of the glucose and sorbitol, the acid catalyst consist-ing of citric acid, tartaric acid, fumaric acid, lactic acid, tannic acid, succinic acid anhydride and adipic acid anhydride and combinations thereof, to provide a nontoxic, edible mixture containing glucosylsorbitol as a major component thereof.
by weight of the glucose and sorbitol, the acid catalyst consist-ing of citric acid, tartaric acid, fumaric acid, lactic acid, tannic acid, succinic acid anhydride and adipic acid anhydride and combinations thereof, to provide a nontoxic, edible mixture containing glucosylsorbitol as a major component thereof.
9. The process of claim 8 wherein the acid catalyst is present in an amount of from about 0.2% to 2.0% by weight.
10. The process of claim 8 wherein the reaction is carried out at a temperature of from about 140°C to 180°C and in a reaction time of from about 30 minutes to 3 hours.
11. A food bulking agent containing glucosylsorbitol as a major amount in admixture with trimer glucosylsorbitol polymer or decomposition products of glucose or both, which food-bulking agent is produced by the process of claim 8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000375552A CA1179334A (en) | 1981-04-15 | 1981-04-15 | Process for the manufacture of glucosylsorbitol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000375552A CA1179334A (en) | 1981-04-15 | 1981-04-15 | Process for the manufacture of glucosylsorbitol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1179334A true CA1179334A (en) | 1984-12-11 |
Family
ID=4119748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000375552A Expired CA1179334A (en) | 1981-04-15 | 1981-04-15 | Process for the manufacture of glucosylsorbitol |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1179334A (en) |
-
1981
- 1981-04-15 CA CA000375552A patent/CA1179334A/en not_active Expired
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