Sugar alcohol composition

Abstract

The present invention relates to a liquid sugar alcohol composition comprising talitol and allitol, wherein the solid content of allitol is less than 11 wt% with respect to 100 wt% of the liquid sugar alcohol composition, and in which crystal precipitation is prevented.

Description

sugar alcohol composition

[0001] The present invention relates to a mixed sugar alcohol composition comprising alitol and tallitol, wherein crystal precipitation is prevented.

[0002] Recently, rare sugars, which exist in nature in extremely small quantities, have been attracting attention as new functional sugar sources and bioactive substances. These rare sugars are used as non-calorie sweeteners, as ingredients in dietary supplements, and as food ingredients with coloring and flavoring properties.

[0003] Rare saccharides include monosaccharides with reducing power (e.g., D-allulose, D-tagatose, D-allose) and sugar alcohols without reducing power (e.g., D-talitol, D-mannitol). However, the number of commercially available products, such as D-allulose and D-tagatose, is limited, and mass production methods have not yet been established, making them expensive.

[0004] Alitol and tallitol are monosaccharides classified as sugar alcohols, and are rare sugar alcohols rarely found in nature. Recently, demand for various types of sugar alcohols has increased, necessitating the development of methods for easily and stably producing new sugar alcohols. Sugar alcohol production methods include chemical and biological methods. One such method is an organic chemical method, which can be used to reduce monosaccharides such as allose, allulose, and tagatose using high-temperature, high-pressure hydrogen in the presence of a metal catalyst.

[0005] Possible methods for producing D-talitol include chemical and biological methods. Among these chemical methods, a common chemical synthesis method involves hydrogen reduction using allulose as a starting material under high temperature and high pressure. Among biological methods, research is underway on methods for producing D-talitol by extracting it from organisms that contain relatively large quantities of it, or on methods using microorganisms.

[0006] Hydrogenation of allulose yields a mixture of alitol and tallitol. While asymmetric reduction is possible through microbial reactions, efficient reduction of allulose to alitol is not feasible. Therefore, an industrially inexpensive reduction (hydrogenation) method is desirable. However, the hydrogenation reaction of allulose produces two polyols, alitol and tallitol, from the ketose allulose. Furthermore, the chromatographic elution positions of alitol and tallitol are close together, making it difficult to separate alitol from D-talitol.

[0007] One example of the present invention provides a sugar alcohol composition comprising tallitol, in which the content of impurities other than tallitol is very low and the mixing ratio of two or more types of sugar alcohols is desirable.

[0008] Another example of the present invention is to provide a stabilized high-concentration sugar alcohol composition without crystal precipitation or clouding and a method for producing the same.

[0009] Another example of the present invention provides a method for preventing crystal precipitation or white clouding of a sugar alcohol composition containing tallitol by controlling the mixing ratio of two or more types of sugar alcohols, for example, the content ratio of alitol in a sugar alcohol composition containing tallitol and alitol, and a use of alitol for the same.

[0010] The present invention aims to provide a sugar alcohol composition having improved properties of a sugar alcohol including tallitol. In a specific example, the present invention relates to a sugar alcohol composition containing tallitol that prevents or delays crystal precipitation or white clouding in a mixed sugar alcohol composition containing tallitol, and a stabilized sugar alcohol composition containing tallitol that does not cause crystal precipitation or white clouding even under harsh conditions such as room temperature as well as low temperature, the presence of crystal-inducing substances, or long-term storage.

[0011] The present invention provides a sugar alcohol composition containing tallitol and alitol at a specific mixing ratio, with a very small content of impurities other than tallitol. The present invention relates to a method for preventing crystal precipitation or white clouding of a sugar alcohol composition containing tallitol by controlling the mixing ratio of two or more types of sugar alcohols, for example, the content ratio of alitol in a sugar alcohol composition containing tallitol and alitol, and to a use of alitol for the same.

[0012] The sugar alcohols included in the above mixed sugar alcohol composition are tallitol and allitol, which may include D or L-stereoisomers, for example, in the form of D-allitol or D-talitol.

[0013] The present invention relates to a liquid sugar alcohol composition comprising tallitol, alitol, and water, such as a sugar alcohol syrup, which may be a stabilized sugar alcohol composition free from crystal precipitation or clouding. The crystals mainly comprise alitol, and for example, the solid content of alitol may be 50 wt% or more, 60 wt% or more, 70 wt% or more, 80 wt% or more, 90 wt% or more, 95 wt% or more, 96 wt% or more, 97 wt% or more, 98 wt% or more, 99 wt% or more, or 99.5 wt% or more.

[0014] Specifically, a liquid sugar alcohol composition comprising alitol and talitol may be a sugar alcohol composition that prevents crystal precipitation, wherein the solid content of alitol is less than 11 wt% based on 100 wt% of the liquid sugar alcohol composition, and specifically, the solid content of alitol may be 10 wt% or less, 9 wt% or less, 8 wt% or less, 7 wt% or less, 6 wt% or less, 5 wt% or less, or 4 wt% or less, for example, 0.001 wt% or more to less than 11 wt%, 0.01 wt% or more to less than 11 wt%, 0.1 wt% or more to less than 11 wt%, or 0.5 wt% or more to less than 11 wt%. When the solid content of alitol in the sugar alcohol composition is excessively high, crystals are easily formed due to alitol, and white turbidity occurs.

[0015] In addition, in the sugar alcohol liquid composition, the content of the tallitol solid content may be 50 wt% or more, 55 wt% or more, 56 wt% or more, 57 wt% or more, 58 wt% or more, 59 wt% or more, or 60 wt% or more, for example, 50 wt% to 99 wt%, 55 wt% to 99 wt%, 56 wt% to 99 wt%, 57 wt% to 99 wt%, 58 wt% to 99 wt%, 59 wt% to 99 wt%, or 60 wt% to 99 wt%, and more specifically, 67 to 76 wt%.

[0016] The liquid sugar alcohol composition comprising alitol and tallitol according to the present invention is a sugar alcohol composition comprising tallitol as a main component, which means that the solid content of tallitol is 50 wt% or more based on 100 wt% of the total composition, or the solid content of tallitol is 50 wt% or more based on 100 wt% of the solid content of the composition comprising tallitol.

[0017] The total solids content of the above sugar alcohol liquid composition may be 20 wt% or more, 25 wt% or more, 30 wt% or more, 35 wt% or more, 40 wt% or more, 45 wt% or more, 50 wt% or more, 55 wt% or more, 60 wt% or more, or 70 wt% or more, for example, 65 wt% to 70 wt%, 65 wt% to 80 wt%, 65 wt% to 85 wt%, 70 wt% to 80 wt%, 70 wt% to 85 wt%, or 70 to 80 Brix. In the present specification, 'syrup' is a liquid, and includes, for example, a solution.

[0018] The sugar alcohol composition according to the present invention may further include allulose in addition to tallitol and alitol, and for example, the sugar alcohol composition may have an allulose solid content of 5 wt% or less, 3 wt% or less, 2.5 wt% or less, 2 wt% or less, or 1.6 wt% or less, based on the total weight% of the sugar alcohol composition, and more specifically, may be 0.01 to 5 wt%, 0.01 to 3 wt%, 0.01 to 2.5 wt%, 0.01 to 2 wt%, or 0.01 to 1.6 wt%, for example, may be 0.07 to 1.6 wt%.

[0019] The liquid sugar alcohol composition comprising alitol and tallitol according to the present invention can be manufactured by various methods, such as chemical methods, extraction methods, and biological conversion reactions, and can be obtained, for example, by manufacturing, separating, and purifying a raw material including allulose. The sugar alcohol composition may be a tallitol fraction obtained by high-purity separation of a reaction product obtained by hydrogenation of allulose in the presence of a metal catalyst using SMB chromatography.

[0020] Hereinafter, the sugar alcohol composition of the present invention can be manufactured by various methods, including chemical methods, extraction methods, and biological conversion reactions. For example, it can be manufactured by hydrogenation reaction using a metal catalyst and obtained by performing SMB high-purity separation. Hereinafter, a method for manufacturing a sugar alcohol composition including tallitol and alitol will be described in detail as an example.

[0021]

[0022] (1) Hydrogenation reaction of allulose

[0023] The metal catalyst used in the method for producing sugar alcohol of the present invention is a catalyst containing a metal selected from elements of Group 8 of the periodic table. Elements of Group 8 of the periodic table refer to elements of iron, cobalt, nickel, and the platinum group. Here, the platinum group elements refer to six elements: ruthenium, rhodium, palladium, osmium, iridium, and platinum. Among the metals selected from elements of Group 8 of the periodic table, metals selected from nickel and platinum group elements are preferably used as the catalyst in the present invention. More preferably, the metal is selected from nickel, ruthenium, platinum, and palladium. In addition, the properties of the catalyst used in the reduction reaction are not solely dependent on the type of metal, but are also influenced by the support on which the metal is supported. Supports on which the metal catalyst used in the present invention is supported include, but are not limited to, activated carbon, metal oxides such as titanium oxide and alumina, barium sulfate, diatomaceous earth, and the like.

[0024] The specific embodiment of the method for producing the sugar alcohol of the present invention is not particularly limited, but typically, ketohexose is dissolved in a solvent such as water, the metal catalyst is added, and then placed in a pressure vessel. By injecting hydrogen into the pressure vessel, a hydrogenation reaction of ketohexose can be performed.

[0025] In this case, the solvent used is usually water, but may also be an alcohol solvent such as ethanol, methyl acetate, ethyl acetate, a mixed solvent thereof, or a mixed solvent of these solvents and water. The concentration of ketohexose in the hydrogenation reaction solution is usually 1 to 60 w / v %, preferably 5 to 50 w / v %.

[0026] In addition, the reaction temperature is 10 to 150℃, and the reaction pressure is 1 to 200kg / cm 2 It can be. The reaction temperature is usually 10 to 150℃, preferably 10 to 70℃ to reduce the production of reaction by-products, and more preferably 30 to 60℃. The reaction pressure is usually 1 to 200kg / ㎠, and preferably 5 to 100kg / ㎠.

[0027] The progress of the reaction can be monitored by sampling the hydrogenation reaction solution at regular intervals and analyzing the ketohexose and sugar alcohol in the reaction solution. Analysis of ketohexose and sugar alcohol can be performed using various methods, such as HPLC analysis.

[0028] After the hydrogenation reaction, the catalyst can be easily removed by filtration, centrifugation, etc. By removing the catalyst in this way, a solution containing the desired sugar alcohol can be obtained.

[0029] In addition, in the method for producing sugar alcohols of the present invention, the production ratio of sugar alcohols such as D-talitol and alitol can be changed depending on the type of metal catalyst used. That is, the production ratio of two or more sugar alcohols can vary depending on conditions such as the type of metal contained in the catalyst and the type of support.

[0030] When using Raney nickel in the production of tallitol and alitol, it is preferable to obtain a tallitol:allitol production ratio of about 50:50 to 40:60, and when using platinum, it is preferable to obtain a tallitol:alitol production ratio of about 30:70 to 42:58.

[0031] As described above, according to the method of the present invention, a mixture containing a large amount of a specific sugar alcohol such as alitol or tallitol can be easily obtained.

[0032]

[0033] (2) Separation and purification of sugar alcohol reaction products

[0034] The process for manufacturing a sugar alcohol composition according to the present invention includes an ion purification and simulated moving bed (SMB) chromatography separation process of the hydrogenation reaction product of the allulose. In a specific example, the hydrogenation reaction product of the allulose is separated into a tallitol fraction having a higher tallitol content than the hydrogenation reaction product and an alitol raffinate by performing an ion purification and SMB chromatography separation process, and the tallitol fraction can be input into a tallitol concentration process or a crystallization process. The above-mentioned talitol fraction may be a concentrate obtained as such or by concentration, and the concentrate may have a solids content of, for example, 60 wt% or more, 65 wt% or more, or 70 wt% or more, for example, 60 to 99 wt%, 65 to 99 wt%, 70 to 99 wt%, 60 to 95 wt%, 65 to 95 wt%, 70 to 95 wt%, 60 to 90 wt%, 65 to 90 wt%, 70 to 90 wt%, 60 to 85 wt%, 65 to 85 wt%, 70 to 85 wt%, 60 to 83 wt%, 65 to 83 wt%, or 70 to 83 wt%.

[0035] The content of the above-mentioned tallitol solids may include separating / purifying such that the content is 50 wt% or more, 55 wt% or more, 60 wt% or more, 65 wt% or more, 66 wt% or more, 67 wt% or more, 68 wt% or more, 69 wt% or more, 70 wt% or more, 71 wt% or more, 72 wt% or more, 73 wt% or more, 74 wt% or more, 75 wt% or more, 76 wt% or more, 80 wt% or more, or 90 wt% or more, for example, 65 to 80 wt% or 67 to 76 wt%, based on the total weight % of the tallitol fraction or concentrate thereof, i.e., the liquid sugar alcohol composition.

[0036] The content of the above-mentioned alitol solids may include separating / purifying the alitol fraction or its concentrate, i.e., less than 11 wt%, 10 wt% or less, 9 wt% or less, 8 wt% or less, 7 wt% or less, 6 wt% or less, 5 wt% or less, or 4 wt% or less, for example, 0.1 wt% or more and less than 11 wt%, based on the total weight of the liquid sugar alcohol composition.

[0037] The tallitol fraction or concentrate thereof, i.e., the liquid sugar alcohol composition, may further comprise allulose in addition to tallitol and alitol, and the content of the allulose solids may be 5 wt% or less, 3 wt% or less, 2.5 wt% or less, 2 wt% or less, or 1.6 wt% or less, based on the total weight of the tallitol fraction or concentrate thereof, i.e., the liquid sugar alcohol composition, and more specifically, may be 0.01 to 5 wt%, 0.01 to 3 wt%, 0.01 to 2.5 wt%, 0.01 to 2 wt%, or 0.01 to 1.6 wt%, for example, may be 0.07 to 1.6 wt%.

[0038] In the above tallitol manufacturing process, the ion purification process is a process for removing ions contained in the reactants, and can be performed before and / or after the SMB chromatography separation process. The first ion purification process, which is performed before performing the high-purity separation using the SMB chromatography, can be performed by the same or different method as the second ion purification of the tallitol fraction below, and can be performed, for example, using one or two or more separation columns filled with ion exchange resins of the same or different types. The ion purification process can be performed at a temperature of 35 to 50°C, for example, 38 to 58°C, taking into account the physical properties of the resin used for ion purification and the ion purification efficiency.

[0039] The above SMB chromatography separation process can be performed at a temperature of 45 to 70°C, for example, 50 to 65°C.

[0040] In one embodiment of the present invention, before performing the first ion purification process of the talito-hydrogenated product, a process of optionally treating the talito-hydrogenated product with activated carbon may be additionally performed. In addition, optionally, after performing the first ion purification process and before performing the SMB chromatography separation process, a process of concentrating the product to a solid content of 45 to 55% may be additionally performed. Accordingly, the separation process of the talito-hydrogenated product according to the present invention may include the first ion purification process and the SMB chromatography separation process for the talito-hydrogenated product, or the activated carbon treatment, the first ion purification process, and the SMB chromatography separation process for the talito-hydrogenated product, and after the first ion purification process and before performing the SMB chromatography separation process, a concentration process may be additionally optionally performed.

[0041] The high-purity separation process using the above SMB chromatography is a separation method that is easy to secure the stability of the material because there is no phase change during the separation process. Among these adsorption separation methods, the simulated moving bed (SMB) adsorption separation method can be used as a liquid-phase adsorption separation method, and the high-purity separation using the SMB chromatograph has the advantage of superior purity and productivity and the use of less solvent compared to the existing batch chromatography by separating continuously using a number of columns. The above simulated moving bed (SMB) adsorption separation process is a process in which the injection of the mixture to be separated and the production of the raffinate and extract are performed continuously.

[0042] The basic principle of SMB is to simulate the countercurrent flow of the stationary and mobile phases by moving the columns at regular time intervals, thereby enabling continuous separation. Fast-moving substances with a low affinity for the adsorbent move in the direction of the liquid phase flow and are collected as an extract, while slow-moving substances with a high affinity for the adsorbent move in the direction of the stationary phase flow and are collected as a raffinate. The columns are connected in series, with the inlet containing the mixture and mobile phase, and the outlet containing the target extract and raffinate.

[0043] Conventionally, adsorption separation methods using ion exchange resins have been known as methods for separating sugar alcohols. Reduction of ketohexose yields two types of sugar alcohols. These two types of sugar alcohols, obtained in this manner, require further separation into individual sugar alcohols with distinct properties.

[0044] Meanwhile, a separation method utilizing a simulated moving bed chromatography separation device is known as a method for separating a specific component from a stock solution containing two or more components. Such a simulated moving bed chromatography separation device generally has a plurality of packed columns in which an adsorbent having a selective adsorption capacity for a specific component among two or more components contained in the stock solution is serially filled through a pipe.

[0045] The purpose of the present invention is to focus on the properties and functionality of sugar alcohols, particularly specific sugar alcohols, and to operate a simulated moving bed from a stock solution containing two types of sugar alcohols under specific conditions. Another purpose of the present invention is to provide a method capable of separating solutions containing each sugar alcohol with a high recovery rate.

[0046] To solve the above problems, the inventors of the present invention have developed a method for continuously chromatographically separating a solution containing two types of sugar alcohols with high purity and high recovery rate from a solution containing each sugar alcohol, thereby continuously producing industrially effective high-purity, high-recovery sugar alcohol solution. Mass production is possible.

[0047] In a method for chromatographically separating fractions containing large amounts of each of tallitol and allitol from a crude solution containing tallitol and allitol as sugar alcohols using water as an eluent,

[0048] A method for separating sugar alcohols is provided, characterized in that a raw solution having a sugar concentration of 20% or more and an eluent are supplied to a packed column filled with a calcium-type strong acid cation exchange resin as an adsorbent having a selective adsorption ability for tallitol and alitol, and the circulating solution is continuously chromatographically separated into a tallitol fraction and an alitol fraction.

[0049] That is, the method for separating sugar alcohols according to the present invention comprises a method for chromatographically separating a raw solution containing tallitol and alitol into a tallitol fraction containing a lot of tallitol and an alitol fraction containing a lot of alitol using water as an eluent, characterized in that a plurality of packed columns filled with a calcium-type strong acid cation exchange resin having calcium ions as an adsorbent having a selective adsorption ability for tallitol and alitol form a pseudo-moving bed of the adsorbent, and continuously chromatographically separating the circulating solution into a tallitol fraction and an alitol fraction.

[0050] The purpose is to present a composition of a crystal stock solution that suppresses the formation of alitol crystals in a talito fraction after high-purity separation of SMB. This is an efficient high-purity separation system for alitol and talito using SMB.

[0051]

[0052] (3) Use of sugar alcohol composition containing tallow

[0053] The sugar alcohol composition manufactured, separated and purified according to the present invention, and containing tallitol as a main component, can be manufactured in a liquid form as is or can be manufactured by concentrating it, and can then be manufactured into a product by performing a crystallization process to form crystals containing tallitol as a main component. The composition containing tallitol as a main component means that the solid content of tallitol is contained at 50 wt% or more based on 100 wt% of the total content of the entire composition.

[0054] The sugar alcohol composition manufactured above can be manufactured into a liquid, powder or crystal form and can be sold as a final product in that form or used in the same manner as conventional sugar alcohols or as a sweetener, as a food, food additive, beverage or beverage additive.

[0055] The present invention relates to a liquid composition comprising stabilized high-concentration tallitol as a main component, which does not cause crystal precipitation or white turbidity, and more specifically, to a stabilized high-concentration tallitol-containing sugar alcohol composition, which does not cause crystal precipitation or white turbidity not only at room temperature but also under harsh conditions such as low temperature, the presence of a crystal-inducing substance, or long-term storage.

[0056] Figure 1 is calcium (Ca 2+ This graph shows the results of HPLC analysis showing that tallitol was separated with high purity up to approximately 97% using a stimulated moving bed (SMB) filled with ion exchange resin of the type.

[0057] Figures 2 and 3 are photographs taken after storing sugar alcohol syrups having various compositions under specific storage conditions according to Example 4, and are photographs that can confirm the presence or absence of crystal precipitation.

[0058] The present invention will be described in more detail with reference to the following examples, but the scope of the invention is not intended to be limited to the following examples.

[0059]

[0060] Example 1: Preparation of sugar alcohol using allulose

[0061] Crystalline allulose was dissolved in distilled water to prepare an allulose syrup having an allulose purity of 99% or higher and a solids content of 30 wt%. 1 L of the allulose syrup was injected into a hydrogenation reactor, and a hydrogenation reaction was performed using 25 ml of nickel as a catalyst. The hydrogenation reaction was performed under conditions of a temperature of 85 to 95°C and a pressure of 75 to 85 bar.

[0062] After the above hydrogenation reaction was completed, the reaction product was filtered through a filter with pores of 1 μm in diameter to remove nickel, and the reaction product from which nickel had been removed was desalted by passing it through a column filled with a mixture of cation exchange resin and anion exchange resin at a rate of 5 times the volume of ion exchange resin per hour. The product after the above ion purification was concentrated in a concentrator at a temperature of 60°C and concentrated to a Brix range of 30 to 50 to produce a concentrate.

[0063] The components and composition of the above concentrate were analyzed by HPLC, and the HLPC analysis conditions were as follows. HPLC sugar composition analysis was performed using Biorad's Aminex HPX-87C column (80°C) by injecting water solvent into 10 μL of the sample at a flow rate of 0.6 ml / min and detecting with RID.

[0064] In the above-obtained sugar alcohol liquid composition, 52.1 wt% of allitol, 45.9 wt% of tallitol, 0.5 wt% of allulose, and 1.5 wt% of other components were included based on 100 wt% of solid content.

[0065]

[0066] Example 2: High-purity separation of sugar alcohols

[0067] The mixture of alitol and tallitol of 30 to 50 Brix prepared in Example 1 was added to calcium (Ca 2+ ) type ion exchange resin was filled to obtain a high-purity separation process using a stimulated moving bed (SMB) to obtain a tallitol fraction with tallitol as the main component.

[0068] The components and composition of the tallitol fraction obtained by the above SMB high-purity separation were analyzed by HPLC, and the analysis results are shown in Figure 1. The HLPC analysis conditions are as follows. HPLC sugar composition analysis was performed using an Aminex HPX-87C column (80°C) from Biorad, and water solvent was injected into 10 μL of the sample at a flow rate of 0.6 ml / min, and detected by RID.

[0069] As shown in Figure 1, calcium (Ca 2+ ) type ion exchange resin was used to separate the content of tallitol with a high purity of up to about 97%, which was confirmed through HPLC. Based on 100 wt% of the total solid content of tallitol, alitol, and allulose contained in the liquid product obtained through the high-purity separation, the sugar composition was confirmed to be that the solid content of tallitol was about 97 wt%, the solid content of alitol was 1.8 wt%, and the solid content of allulose was 1.2 wt%. Accordingly, the tallitol fraction obtained through the SMB high-purity separation was a tallitol fraction including a solid content of tallitol of 80 wt% or more, based on 100 wt% of the total solid content of tallitol, alitol, and allulose.

[0070]

[0071] Example 3: Purification and concentration of sugar alcohols

[0072] The tallitol fraction obtained by performing high-purity separation according to Example 2 was desalted by passing it through a column filled with a resin in which a cation exchange resin and an anion exchange resin were mixed at a rate of 5 times the volume of the ion exchange resin per hour. After that, the desalted product was concentrated to a Brix range of 70 to 80 using a concentrator, thereby obtaining a concentrate of the tallitol fraction.

[0073] The components and composition of the above-mentioned talitol fraction concentrate were analyzed by HPLC, and the analysis results are shown as sample 14 in Table 1 below. The HLPC analysis conditions are as follows. HPLC sugar composition analysis was performed using an Aminex HPX-87C column (80°C) from Biorad, injecting 10 μL of water solvent into the sample at a flow rate of 0.6 ml / min, and detecting with RID.

[0074] In addition, the alitol and tallitol mixture obtained in Example 1 was used to obtain a product with a variety of compositions of the tallitol fraction as an SMB high-purity separation product by controlling the flow rates of the tallitol fraction and the raffinate (high-allitol fraction) of the SMB high-purity separation device in Example 2. The tallitol fraction was treated in a method substantially the same as the desalting and concentration method of Sample 14, thereby obtaining tallitol fraction concentrates of Samples 1 to 13, and the components and compositions thereof were analyzed by HPLC, and the analysis results are shown in Samples 1 to 13 in Table 1 below.

[0075] Based on 100 wt% of the total solid content of tallitol, alitol, and allulose contained in the concentrate of the tallitol fractions of samples 1 to 14 described in Table 1 below, the solid content composition of tallitol, alitol, and allulose was obtained, and the specific results are shown in Table 2 below.

[0076] Item Talitol content (w / w%) Allitol content (w / w%) Allulose content (w / w%) Solid content of talitol fraction concentrate (w / w%) Sample 164.2 15.8 0.0880 Sample 256.1 13.8 0.0770 Sample 366.3 13.5 0.1680 Sample 467 12.9 0.0880 Sample 558 11.8 0.1470 Sample 668.8 11.10 0.0880 Sample 759.4 10.6 0.0770 Sample 871.68 20.1680 Sample 972.67 30.1680 Sample 1062.77 20.1470 Sample 1163.5 6.4 0.1470 Sample Sample 12763.80.2480 Sample 1366.53.30.2170 Sample 1467.91.30.870

[0077] Item Talitol content (w / w%) Allitol content (w / w%) Allulose content (w / w%) Sample 180.2 19.7 0.1 Sample 280.2 19.7 0.1 Sample 382.9 16.9 0.2 Sample 483.8 16.10.1 Sample 582.9 16.9 0.2 Sample 686 13.9 0.1 Sample 784.8 15.10.1 Sample 889.5 10.3 0.2 Sample 990.7 9.10.2 Sample 1089.5 10.3 0.2 Sample 1190.7 9.10.2 Sample 1295 4.7 0.3 Sample 1395 4.7 0.3 Sample 1497 1.8 1.2

[0078]

[0079] Example 4: Crystal formation test of sugar alcohol

[0080] The concentrates (samples 1 to 14) of the talc fractions obtained in the above Example 3 were stored for 7 days at a storage temperature of 4°C (refrigerated storage) or 25°C (room temperature storage). After 7 days of storage, the presence or absence of crystal precipitation was visually observed. If crystal precipitation was observed, it was marked as O, and if no crystals were observed, it was marked as X. The analysis results are shown in Table 3 and Figures 2 to 3 below.

[0081] In Table 3 below, the content (wt / wt%) of each component is expressed as the solid content of each component in wt% based on 100 wt% of the concentrate of the separated and concentrated tallitol fraction, i.e., the liquid sugar alcohol composition.

[0082] Allitol content (w / w%) Storage temperature 4℃ (refrigerated) Crystal formation Storage temperature 25℃ (room temperature) Crystal formation Sample 115.8○○ Sample 213.8○○ Sample 313.5○○ Sample 412.9○○ Sample 511.8○○ Sample 611.1○○ Sample 710.6XX Sample 88.2XX Sample 97.3XX Sample 107.2XX Sample 116.4XX Sample 123.8XX Sample 133.3XX Sample 141.3XX

[0083] As shown in the experimental results of Table 3 and FIGS. 2 to 3, based on 100 wt% of the liquid sugar alcohol composition, i.e., the concentrate of the separated and concentrated talitol fraction, crystals were precipitated when the solid content of alitol included in the liquid sugar alcohol composition was 11 wt% or more, and crystals were not precipitated when the solid content of alitol was less than 11 wt%.

[0084] In summary, based on the results of Examples 2 and 3, when the concentrate of the separated and concentrated talitol fraction, i.e., the alitol solid content contained in the liquid sugar alcohol composition, is less than 11 wt% based on 100 wt% of the total liquid sugar alcohol composition, it was possible to obtain a stabilized talitol syrup that can maintain the quality of the product for a long time without crystallization even under long-term room temperature and refrigerated temperature conditions.

Claims

1. A liquid sugar alcohol composition containing talitol and alitol, wherein the solid content of alitol is less than 11 wt% based on 100 wt% of the liquid sugar alcohol composition, and crystallization is prevented.

2. A liquid sugar alcohol composition in which cloudiness or crystallization is reduced or prevented in the first paragraph.

3. A liquid sugar alcohol composition in claim 1, wherein the solid content of the alitol has a range of 0.001 wt% or more to less than 11 wt% based on 100 wt% of the liquid sugar alcohol composition.

4. A liquid sugar alcohol composition in the first paragraph, wherein the solid content of the tallitol is 50 wt% or more based on 100 wt% of the liquid sugar alcohol composition.

5. A liquid sugar alcohol composition further comprising allulose according to any one of claims 1 to 4.

6. In paragraph 5, a sugar alcohol composition wherein the solid content of the allulose is 5 wt% or less based on 100 wt% of the sugar alcohol composition.

7. In the first paragraph, the sugar alcohol composition is a sugar alcohol composition which is a tallitol fraction obtained by performing SMB high-purity separation on a hydrogenation reaction product of allulose.

8. A method for preventing crystal formation in a liquid sugar alcohol composition by controlling the solid content of alitol to less than 11 wt% based on 100 wt% of a liquid sugar alcohol composition containing allitol and tallitol.

9. A method for preventing crystal formation in a liquid sugar alcohol composition by controlling the solid content of alitol to less than 11 wt% based on 100 wt% of the liquid sugar alcohol composition containing alitol and tallitol in paragraph 8.

10. A method in paragraph 8, wherein the solid content of the tallitol is 50 wt% or more based on 100 wt% of the liquid sugar alcohol composition.

11. A method according to any one of claims 8 to 10, wherein the sugar alcohol composition further comprises allulose.

12. A method according to claim 11, wherein the solid content of the allulose is 5 wt% or less based on 100 wt% of the sugar alcohol composition.

13. A method in claim 8, wherein the sugar alcohol composition is a tallitol fraction obtained by performing SMB high-purity separation on a hydrogenation reaction product of allulose.

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