EP1112004A1 - Compositions de xylitol liquide non-crystallisables et procedes de production desdites compositions par co-hydrogenation - Google Patents

Compositions de xylitol liquide non-crystallisables et procedes de production desdites compositions par co-hydrogenation

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Publication number
EP1112004A1
EP1112004A1 EP99949615A EP99949615A EP1112004A1 EP 1112004 A1 EP1112004 A1 EP 1112004A1 EP 99949615 A EP99949615 A EP 99949615A EP 99949615 A EP99949615 A EP 99949615A EP 1112004 A1 EP1112004 A1 EP 1112004A1
Authority
EP
European Patent Office
Prior art keywords
xylitol
composition
dry solids
weight percent
component
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.)
Withdrawn
Application number
EP99949615A
Other languages
German (de)
English (en)
Inventor
Mary Lou Cunningham
Charles E. Kuenzle
Marguerite Yang
Peter Jamieson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SPI Polyols Inc
Original Assignee
SPI Polyols Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by SPI Polyols Inc filed Critical SPI Polyols Inc
Publication of EP1112004A1 publication Critical patent/EP1112004A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/346—Finished or semi-finished products in the form of powders, paste or liquids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/10—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/34—Sugar alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
    • A23G2200/06—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents containing beet sugar or cane sugar if specifically mentioned or containing other carbohydrates, e.g. starches, gums, alcohol sugar, polysaccharides, dextrin or containing high or low amount of carbohydrate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures

Definitions

  • the present invention relates to non-crystallizing xylitol compositions, and in particular, to liquid xylitol compositions that are non-crystallizing at low temperatures.
  • the invention also relates to a co-hydrogenation process for producing non-crystallizing liquid xylitol compositions, and a co-hydrogenation process for producing liquid xylitol compositions that are non- crystallizing at low temperatures.
  • xylitol as an ingredient in popular consumer products, such as chewing gums and candies.
  • Xylitol has a sweet taste, a cooling effect in its crystalline form, and is non-cariogenic. The latter property provides a beneficial advantage of using xylitol, instead of sugar, as a sweetening agent.
  • xylitol instead of sugar, as a sweetening agent.
  • xylitol actually repairs tooth decay. More recently, oral care companies also have begun to include xylitol in product formulations for toothpastes, mouthwashes, rinses, and the like.
  • Xylitol has been shown in many studies in countries outside the United States to have positive health benefits from reducing ear infections to recalcification of teeth. Many oral care and food manufacturers are exploring means to incorporate xylitol into their products. Developers and manufacturers want the xylitol that they have incorporated into their products to remain in solution form. Many food products are stored at refrigerated and frozen storage temperatures, intentionally and unintentionally.
  • Xylitol is a sweetner that is as-sweet as sucrose. Crystalline xylitol, though, has a large negative heat of solution of -36.7 cal/g. When xylitol crystallizes in a product, the flavor profile changes and the product becomes cooling in the mouth, an objectionable characteristic in many products, such as toothpaste and fruit filings.
  • xylitol In many of its current applications in the confectionary and oral care industries, xylitol is employed in its crystalline (or dry) form.
  • Crystalline xylitol being hygroscopic, quickly absorbs moisture and hardens, thereby making it difficult to handle.
  • the use of crystalline xylitol to produce an end product provides an added cost to that end product, since crystalline xylitol itself and its manufacturing process is expensive.
  • liquid xylitol has been proposed as an alternative to crystalline xylitol.
  • the benefits of liquid xylitol are primarily in ease of handling and also potentially in cost, if the use of crystalline xylitol is avoided.
  • liquid xylitol has a tendency to crystallize out of solution, particularly at high concentrations on a dry solids basis. This makes it difficult to store liquid xylitol.
  • the quality of end products can be diminished significantly.
  • a crystallizing liquid xylitol will crystallize out of toothpaste and plug up tube orifices or pumps, or crystallize in a bottle or around a bottle cap in the case of rinses or mouthwashes.
  • U.S. PatentNo. 5,144,024 discloses anon-crystallizing liquid xylitol composition having a dry solids content of 60-80%, wherein the dry solids are comprised of 50-90% xylitol and 10-50% non-xylitol monomeric or dimeric polyols.
  • the non-xylitol polyols are selected from maltitol, sorbitol, mannitol, glycerol and mixtures thereof.
  • the '024 patent does not teach or suggest liquid xylitol compositions that are non- crystallizing at low temperatures.
  • liquid xylitol/sorbitol formulations at 70% dry solids comprising 70% and 80% xylitol, and at 65% dry solids comprising 80% xylitol, will crystallize after only two weeks at both 5 °C. and 10 °C. Because products are often transported through and/or stored in cold environments, it is desirable to have a liquid xylitol that remains non-crystallizing at low temperatures.
  • the '024 patent teaches using a by-product stream from a xylitol crystallization process that is rich in xylitol, to make a liquid xylitol composition.
  • liquid xylitol can be made by mixing a solution of pure xylitol with a solution containing other polyols.
  • crystalline xylitol is expensive. It desired, therefore, to have process for making liquid xylitol that does not use crystalline xylitol or employ a xylitol crystallization step.
  • An object of the present invention is to provide a non-crystallizing liquid xylitol composition.
  • a non-crystallizing liquid xylitol composition comprises, at between about 65 and about 90 weight percent dry solids, xylitol, in an amount between about 10 and about 50 weight percent of the dry solids, and sorbitol, in an amount between about 50 and about 90 weight percent of the dry solids.
  • Another object of this invention is to provide a liquid xylitol composition that is non- crystallizing at low temperatures.
  • a liquid xylitol composition which comprises, at between about 65 and about 90 weight percent dry solids, xylitol, in an amount between about 10 and about 50 weight percent of the dry solids, and sorbitol, in an amount between about 50 and about
  • 90 weight percent of the dry solids is non-crystallizing at between about 0 °C. and about 10 °C.
  • Another object of this invention is to provide a co-hydrogenation process for producing liquid xylitol compositions.
  • the process comprises co-hydrogenating a sugar syrup mixture comprising a sugar syrup having a dextrose equivalence (DE) of between about 20DE and about 99DE, in an amount between about 55 and about 95 weight percent of the mixture, and xylose, in an amount between about 15 and about 55 weight percent of the mixture.
  • the co- hydrogenating step takes place preferably at a temperature of between about 120 °C. and about 170 °C, and a hydrogen pressure of between about 200 psi and about 2000 psi, for between about 90 and about 180 minutes.
  • a further object of this invention is to provide a co-hydrogenation process for producing non-crystallizing liquid xylitol.
  • the process comprises co-hydrogenating a sugar syrup mixture comprising a sugar syrup having a dextrose equivalence (DE) of between about 20DE and about 99DE, in an amount between about 55 and about 95 weight percent of the mixture, and xylose, in an amount between about 15 and about 55 weight percent of the mixture, to produce a liquid xylitol composition that is non-crystallizing at low temperatures.
  • the co- hydrogenating step takes place preferably at a temperature between about 120 °C.
  • the non-crystallizing liquid xylitol produced by this co-hydrogenation process preferably comprises, at between about 65 and about 90 weight percent dry solids, xylitol, in an amount between about 10 and about 50 weight percent of the dry solids, and sorbitol, in an amount between about 50 and about 90 weight percent of the dry solids.
  • a liquid xylitol composition produced by this co-hydrogenation process is preferably non-crystallizing at between about 0 °C. and about 10 °C.
  • Xylitol in its dry form will crystallize out of products at low temperatures, creating objectionable textures in an ingestible composition such as but not limited to oral care products such as, but not limited to, toothpaste, mouth wash and embedded in the coating of dental floss and food products, such as but not limited to a form of confection , chewing gum and fruit syrup.
  • oral care products such as, but not limited to, toothpaste, mouth wash and embedded in the coating of dental floss and food products, such as but not limited to a form of confection , chewing gum and fruit syrup.
  • the crystals will dissolve in the mouth and create an objectionable mouth sensation.
  • Other co-hydrogenated xylitol/sorbitol sources can also crystallize out at cool temperatures, also causing objectionable textures and a cooling mouth sensation.
  • Liquid xylitol compositions in accordance with this invention comprise preferably between about 60 and about 95 weight percent and preferably between about 65 and 90 weight percent dry solids, more preferably between about 65 and about 80 weight percent dry solids, and even more preferably between about 70 and about 80 weight percent dry solids.
  • a non-crystallizing liquid xylitol composition in accordance with this invention comprises both a xylitol component and a non-xylitol polyol component.
  • a liquid xylitol composition that is non-crystallizing at low temperatures in accordance with this invention, also comprises both a xylitol component and a non-xylitol polyol component.
  • the xylitol component comprises, on a dry solids basis, preferably between about 10 and about 50 weight percent of the dry solids, more preferably between about 20 and about 40 weight percent of the dry solids, and even more preferably between about 30 and about 40 weight percent of the dry solids.
  • the non-xylitol polyol component comprises at least one non-xylitol polyol selected from the group consisting of sorbitol, mannitol, maltitol, maltitriitol, and other larger chain sugar alcohols (i.e., DP4 and greater).
  • the non-xylitol polyol component comprises, on a dry solids basis, preferably between about 50 and about 90 weight percent of the dry solids, more preferably between about 60 and about 80 weight percent of the dry solids, and even more preferably between about 60 and about 70 weight percent of the dry solids.
  • the non-xylitol polyol component comprises non-xylitol monomeric polyols.
  • the non- xylitol polyol component comprises sorbitol.
  • a liquid xylitol composition that is non-crystallizing at low temperatures is non- crystallizing at a temperature of preferably between about 0 °C. and about 10 °C, more preferably between about 0 °C. and about 5 °C, and even more preferably between about 0 °C. and about 3 °C.
  • the liquid xylitol composition is non-crystallizing for preferably at least about 2 months, more preferably at least about 3 months, and even more preferably at least about 4 months.
  • a process for producing a liquid xylitol composition that does not use crystalline xylitol or employ a xylitol crystallization step comprises a co-hydrogenation step.
  • the co- hydrogenation step comprises hydrogenating a sugar syrup mixture.
  • the sugar syrup mixture preferably comprises both xylose and a sugar syrup component.
  • the xylose can be in the form of either a syrup, a solid, or a combination thereof.
  • the sugar syrup component comprises preferably at least one sugar syrup that functions as a source for non-xylitol polyols, and even more preferably at least one sugar syrup that functions as a source for non-xylitol monomeric polyols.
  • Sugar syrups may include dextrose (as a source for sorbitol), maltose (as a source for maltitol), and other starch hydrolysates as sources for larger chain sugar alcohols (e.g., DP3 and greater)
  • the sugar syrup component comprises dextrose.
  • the xylose should have a xylose assay of preferably about 92%, more preferably about
  • Any sugar syrup employed should have a dextrose equivalence (DE) of preferably between about 20DE and about 99DE, more preferably between about 43DE and about 99DE, and even more preferably about 99DE.
  • DE dextrose equivalence
  • a preferred source of xylose is Cultor Food Science/Xyrofin (New York, NY).
  • Preferred sugar syrup sources include A.E. Staley Manufacturing Company (Decatur, IL) and Corn Product, CPC International (Argo, IL).
  • the xylose comprises preferably between about 15 and about 55 weight percent of the sugar syrup mixture, more preferably between about 25 and about 45 weight percent of the sugar syrup mixture, and even more preferably between about 35 and about 45 weight percent of the sugar syrup mixture.
  • the sugar syrup component comprises preferably between about 55 and about 95 weight percent of the sugar syrup mixture, more preferably between about 65 and about 85 weight percent of the sugar syrup mixture, and even more preferably between about 65 and about 75 weight percent of the sugar syrup mixture.
  • the co-hydrogenation step is conducted at a temperature of preferably between about 120 °C. and about 170 °C, more preferably between about 120 °C. and about 150 °C, and even more preferably between about 140 °C. and about 150 °C.
  • Co-hydrogenation is achieved by heating the polyol syrup mixture in an elevated hydrogen pressure environment.
  • the hydrogen pressure is preferably between about 200 psi and about 2000 psi, more preferably between about 200 psi and about 550 psi, and even more preferably between about 200 psi and about 250 psi.
  • Another preferred hydrogen pressure is between about 550 psi and about 2000 psi.
  • Catalysts may be employed during the co-hydrogenation step.
  • the catalyst comprises preferably a nickel catalyst, more preferably a sponge nickel catalyst, and even more preferably a molybdenum promoted sponge nickel catalyst.
  • a preferred brand of catalyst is A7063 (available from Activated Metals and Chemicals, Inc., Sevierville, TN).
  • Any conventional hydrogenation equipment may be used to conduct co-hydrogenation processes according to this invention.
  • the residence time for carrying out the co-hydrogenation step is preferably between about 90 minutes about 180 minutes, more preferably between about 120 minutes and about 150 minutes, and even more preferably about 150 minutes.
  • Non-crystallizing liquid xylitol compositions including liquid xylitol compositions that are non-crystallizing at low temperatures, in accordance with this invention, may be produced by co-hydrogenation processes in accordance with this invention.
  • Example I-IV comprise preferred embodiments of this invention.
  • Example V is a comparative example involving preferred embodiments of this invention. All references to percentages and percent values in the Examples are references to weight percentages and weight percent values, unless otherwise indicated. The present invention is not limited to these Examples.
  • Samples 1.1 through 1.7 were made by co-hydrogenation of sugar mixtures comprising 35%) xylose and 65% dextrose on a dry solids basis at 50 weight percent dry solids. All sugar mixtures were combinations of crystalline xylose and 99DE dextrose syrup.
  • the catalyst employed in Example I was a sponge nickel catalyst type A7063 (available from Activated Metals and Chemicals, Inc., Sevierville, TN). This is a molybdenum promoted catalyst, typically containing approximately 1.5% molybdenum and 85% nickel. As shown in Table 1, the initial catalyst charge was 5% on a dry solids basis. For each subsequent sample, the same catalyst was recycled and an additional percentage amount was added to compensate for physical losses and losses in activity.
  • Samples 1.1 through 1.7 were each produced in a set of Parr rocking reactors (total volume 3 L), to which the standard charge weight was 850 grams.
  • the operating conditions of temperature, hydrogen pressure, and residence time are indicated in Table 1.
  • each sample was cooled, pressure was relieved and the reaction mass was discharged to a graduated cylinder to allow the nickel catalyst to settle to the bottom. Typically, each sample was allowed to settle overnight. After catalyst settling, the supernant liquid was decanted off the top and filtered through a Buchner funnel to remove fines.
  • the sample was then ion exchanged through AMBERLITE A200 strong acid cation resin (available from Rohm & Haas, Philadelphia, PA) and either Mitsubishi RD A 416 strong base anion resin (available from Mitsubishi Chemical, White Plains, NY) or A651 strong base anion resin (available from Sybron, Birmingham, NJ).
  • AMBERLITE A200 strong acid cation resin available from Rohm & Haas, Philadelphia, PA
  • Mitsubishi RD A 416 strong base anion resin available from Mitsubishi Chemical, White Plains, NY
  • A651 strong base anion resin available from Sybron, Birmingham, NJ
  • Table 1 indicates the xylitol and sorbitol percentanges of each ion-exchanged sample.
  • the notation "d.b.” indicates dry solids basis.
  • Samples 2.1 through 2.6 were made by co-hydrogenation of sugar mixtures comprising 50% xylose and 50% dextrose on a dry solids basis at 50 weight percent dry solids. All sugar mixtures were combinations of crystalline xylose and 99DE dextrose syrup.
  • Example II The catalyst employed in Example II was a continuing recycle of the same recycled sponge nickel catalyst type A7063 employed in Example I. As shown in Table 2, for each sample, the catalyst was recycled and an additional percentage amount was added to compensate for physical losses and losses in activity.
  • Samples 2.1 through 2.6 were each produced in a set of Parr rocking reactors (total volume 3 L), to which the standard charge weight was 850 grams.
  • the operating conditions of temperature, hydrogen pressure, and residence time are indicated in Table 2.
  • each sample was cooled, pressure was relieved and the reaction mass was discharged to a graduated cylinder to allow the nickel catalyst to settle to the bottom. Typically, each sample was allowed to settle overnight. After catalyst settling, the supernant liquid was decanted off the top and filtered through a Buchner funnel to remove fines. The sample was then ion exchanged through AMBERLITE A200 strong acid cation resin (available from Rohm & Haas, Philadelphia, PA) and either Mitsubishi RDA 416 strong base anion resin (available from Mitsubishi Chemical, White Plains, NY) or A651 strong base anion resin (available from Sybron, Birmingham, NJ). The ion exchanged sample was evaporated to about 70 weight percent dry solids.
  • AMBERLITE A200 strong acid cation resin available from Rohm & Haas, Philadelphia, PA
  • Mitsubishi RDA 416 strong base anion resin available from Mitsubishi Chemical, White Plains, NY
  • A651 strong base anion resin available from Sybron, Birmingham, NJ.
  • Table 2 indicates the xylitol and sorbitol percentanges of each ion-exchanged sample.
  • the notation “d.b.” indicates dry solids basis. Otherwise, the percentages are "as is” (i.e., including percent water).
  • EXAMPLE III Referring to Table 3, Samples 3.1 through 3.6 were made by co-hydrogenation of sugar mixtures comprising 65% xylose and 35% dextrose on a dry solids basis at 50 weight percent dry solids. All sugar mixtures were combinations of crystalline xylose and 99DE dextrose syrup.
  • Example III The catalyst employed in Example III was a continuing recycle of the same recycled sponge nickel catalyst type A7063 employed in Example II. As shown in Table 3, for each sample, the catalyst was recycled and an additional percentage amount was added to compensate for physical losses and losses in activity. Samples 3.1 through 3.6 were each produced in a set of Parr rocking reactors (total volume 3 L), to which the standard charge weight was 850 grams. The operating conditions of temperature, hydrogen pressure, and residence time are indicated in Table 3.
  • each sample was cooled, pressure was relieved and the reaction mass was discharged to a graduated cylinder to allow the nickel catalyst to settle to the bottom. Typically, each sample was allowed to settle overnight. After catalyst settling, the supernant liquid was decanted off the top and filtered through a Buchner funnel to remove fines. The sample was then ion exchanged through AMBERLITE A200 strong acid cation resin (available from Rohm & Haas, Philadelphia, PA) and either Mitsubishi RDA 416 strong base anion resin (available from Mitsubishi Chemical, White Plains, NY) or A651 strong base anion resin (available from Sybron, Birmingham, NJ). The ion exchanged sample was evaporated to about 70 weight percent dry solids.
  • AMBERLITE A200 strong acid cation resin available from Rohm & Haas, Philadelphia, PA
  • Mitsubishi RDA 416 strong base anion resin available from Mitsubishi Chemical, White Plains, NY
  • A651 strong base anion resin available from Sybron, Birmingham, NJ.
  • Blend 4.1 was made from a combination of Samples 1.2 through 1.7.
  • Blend 4.2 was made from a combination of Samples 2.1 through 2.6.
  • Blend 4.3 was made from a combination of Samples 3.1 through 3.6.
  • Table 4 indicates the water, xylitol and sorbitol weight percentanges of each Blend.
  • the notation "d.b.” indicates dry solids basis.
  • Comparative Blends Al through A3 and Bl through B3 represent three xylitol/sorbitol ratios, as shown in Table 5. Comparative Blends Al through A3 were made by combining dry xylitol, dry sorbitol and water. Comparative Blends Bl through B3 were made by combining dry xylitol and liquid sorbitol. Each of the six Comparative Blends had a dry solids content of approximately 70 weight percent. These Comparative Blends were set up for a stability test at room temperature
  • Blends 4.1 through 4.3 were also set up for stability under the same temperature conditions.
  • Comparative Blends A3 and B3 (containing approximately 65% xylitol d.b.) showed crystal growth at 3 °C.
  • Blend 4.3 (containing approximately 62% xylitol d.b.) showed no crystal growth at 3 °C.
  • Blend 4.3 has yet to show any crystal growth at 3 °C. None of the other comparative blends or blends showed crystal growth at either room temperature or at 3°C.
  • Examples 5-1 and 5-2 were a toothpaste formulation with 65% Xylitol/35%) Sorbitol and contained the following ingredients:
  • Carboxymethyl-cellulose 26 1.30 Sodium Saccharin 14 0.70 De-ionized water 306 15.09
  • the example 5-2 demonstrated toothpaste that had a more white color than comparison example 5-1. This was determined by the use of the Gardner "color meter”.
  • Example 5-2 demonstrated more cohesion than comparison example 5-1. This was determined by the use of the Instron.
  • Example 5-1 had less gloss than example 5-2.
  • Example 5-1 appeared to be not as white as example 5-2.
  • Example 5-1 appeared to skin where example 5-2 did not.
  • Example 6 illustrates the liquid xylitol composition being used in candy. Dry and liquid materials were used in an open pan. 10 grams of extra water were added to formulas A, C and E below to allow the dry materials to dissolve when they were heated. Extra water was not need, with the co-hydrogenated mixture.
  • the co-hydrogenated mixture used in this example had a 70% level of solids and contained 65% xylitol and 35%) sorbitol. The mixtures were heated over a gas flame until their weight revealed the loss of weight sufficient to make the cooked candy less than 5% moisture. Samples were then poured onto cooling pan and into plastic lined molds. Samples were evaluated over 48 hours.
  • Formula A Fastest crystal growth (less than one hour).
  • the final cooled product is very hard and has very visible large crystals.
  • the hard candy is not sticky.
  • Formula B Second slowest crystal growth.
  • the final cooled product is hard, homogeneous, and has much less noticeable crystals.
  • the hard candy is not sticky.
  • Formula C Slowest crystal growth. When the others samples were hard homogeneous after 24 hours, this sample was still greatly syrup with visible large crystals. The Candy is very sticky (even the crystallized part) after 24 hours, though hard and non-sticky after 72 hours.
  • Formula D Faster crystal growth than Formula B and slower than Formula E.
  • Final cooled product is hard, with slightly less visible crystals than Formula E. The hard candy is not sticky.
  • co-hydrogenated xylitol allows the manufacturing of high xylitol candy with greater ease than with solid xylitol alone or with dry xylitol and dry sorbitol.
  • the water in the co-hydrogenated material eliminates the need for added water to dissolve the polyols before cooking.
  • the co-hydrogenated xylitol/non-xylitol polyol (such as but not limited to sorbitol) slows the crystallization down and yet allows for less noticeable, smaller crystals in the finished product. Just adding sorbitol and xylitol does not effect the crystal growth in the same way.
  • the invention is not limited by the percentage of xylitol, thus co-hydrogenated xylitol/sorbitol at 35/65 ratio should perform with the same properties as that at the higher xylitol ratio.

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Abstract

L'invention concerne une composition de xylitol liquide non-crystallisable contenant entre environ 65 et 90 % en poids de matières sèches, une quantité de xylitol comprise entre environ 10 et 50 % en poids des matières sèches, et une quantité de sorbitol comprise entre environ 50 et 90 % en poids des matières sèches. De préférence, cette composition de xylitol liquide ne crystallise pas à une température comprise entre environ 0 et 10 °C. L'invention concerne également un procédé de production de compositions de xylitol liquide par co-hydrogénation, qui consiste à co-hydrogéner un mélange de sirop de sucre, dont la quantité de sirop de sucre, d'équivalent-dextrose (DE) compris entre environ 20 et 99 DE, est comprise entre environ 55 et 95 % en poids du mélange, et un xylose dont la quantité est comprise entre environ 15 et 55 % en poids du mélange. Ce procédé peut être mis en oeuvre pour produire des compositions de xylitol liquide non-crystallisables.
EP99949615A 1998-09-10 1999-09-09 Compositions de xylitol liquide non-crystallisables et procedes de production desdites compositions par co-hydrogenation Withdrawn EP1112004A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US9974798P 1998-09-10 1998-09-10
US99747P 1998-09-10
PCT/US1999/020745 WO2000015048A1 (fr) 1998-09-10 1999-09-09 Compositions de xylitol liquide non-crystallisables et procedes de production desdites compositions par co-hydrogenation

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WO (1) WO2000015048A1 (fr)

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CN103442583B (zh) * 2011-03-31 2015-09-09 亿滋日本株式会社 流体性食品组合物和糖食
WO2017143118A1 (fr) 2016-02-19 2017-08-24 Intercontinental Great Brands Llc Procédé de création de flux de valeurs multiples à partir de sources de biomasse
CN112704221A (zh) * 2020-12-29 2021-04-27 浙江华康药业股份有限公司 一种山梨糖醇液的制备方法
WO2024062157A1 (fr) * 2022-09-19 2024-03-28 Lajoie Oy Composition d'édulcorant, produit alimentaire, procédé de production d'un produit alimentaire et utilisation d'ensembles supramoléculaires
FI20225811A1 (en) * 2022-09-19 2024-03-20 Lajoie Oy Sweetening composition, food product and process for making food product

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DE1058038B (de) * 1956-12-12 1959-05-27 Udic Sa Lausanne Verfahren zur Herstellung haltbarer konzentrierter waesseriger Loesungen mehrwertiger Alkohole
US5144024A (en) * 1990-10-11 1992-09-01 Tammy Pepper Shelf stable liquid xylitol compositions
US5728225A (en) * 1993-07-26 1998-03-17 Roquette Freres Viscous liquid compositions of xylitol and a process for preparing them
FR2726829B1 (fr) * 1994-11-10 1997-01-17 Roquette Freres Composition de polyols, son procede de preparation et ses applications

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CA2344078C (fr) 2007-04-17
AU6245299A (en) 2000-04-03
JP2002524479A (ja) 2002-08-06
BR9913216A (pt) 2001-10-02
CA2344078A1 (fr) 2000-03-23
WO2000015048A1 (fr) 2000-03-23

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