Methods for synthesis and purification of allulose

Abstract

The present invention relates to a process for the preparation of an allulose product comprising: enzymatic conversion of fructose to allulose; separation of the crude product thus obtained by chromatography into (i) one or more allulose-enriched fractions, (ii) a fructose-enriched fraction, and optionally (iii) a purge fraction, preferably by simulated moving bed chromatography; and recycling of the fructose-enriched fraction to the enzymatic conversion.

Description

[0001] Priority is claimed to European patent application number 24 152 156.6, filed on January 16, 2024.

[0002] The present invention relates to a method for preparing an allulose product, comprising: enzymatically converting fructose into allulose; preferably separating the crude product therefrom by chromatographic separation of (i) one or more allulose-rich fractions, (ii) fructose-rich fractions, and optionally (iii) purge fractions by simulated moving bed chromatography; and recycling the fructose-rich fractions back to the enzymatic conversion.

[0003] According to existing technology, fructose is enzymatically converted to allulose. However, this conversion is incomplete due to product inhibition and other factors affecting the enzyme's catalytic conversion. Instead, a considerable amount of unconverted fructose starting material remains in the crude product. To obtain a high-purity allulose product, it is necessary to separate the residual fructose from the allulose. This can be achieved by chromatography, typically simulated moving bed (SMB) chromatography, thus providing an allulose-rich fraction and a fructose-rich fraction. Since the fructose-rich fraction usually contains a significant amount of fructose, it is advantageous to recycle the fructose-rich fraction back into the process.

[0004] Depending on the source of the fructose used to provide the starting material, the starting material may contain other carbohydrates.

[0005] When fructose is obtained from sucrose, it can be cleaved into a 1:1 mixture of fructose and glucose (invert sugar), and the glucose can be separated from the fructose, for example, by chromatography. Preferably, glucose can first be isomerized to fructose under the enzymatic catalysis of a suitable isomerase, and then, for example, only the residual, i.e., unisomerized glucose, can be separated from the fructose by chromatography. In either case, the fructose thus purified may still contain some glucose and / or sucrose.

[0006] When fructose is obtained from starch or cellulose, the starch or cellulose can first be degraded into glucose, which is then isomerized to fructose under the enzymatic catalysis of a suitable isomerase. Subsequently, the residual (i.e., unisomerized) glucose can be separated from the fructose, for example by chromatography. In these cases, the fructose thus purified may still contain some glucose and / or glucose oligosaccharides and / or cellulosic oligosaccharides.

[0007] Furthermore, additional byproducts and impurities may form depending on subsequent post-processing measures and recirculation, such as at high temperatures. The content of such byproducts and impurities in allulose products should be as low as possible. Therefore, the chromatographic separation of allulose and fructose is typically optimized for the purity of the allulose-rich fraction, thereby reducing the purity of the fructose-rich fraction, which, in addition to fructose, should contain most of the byproducts and impurities.

[0008] However, when allulose and fructose are separated chromatographically and the fructose-rich fraction is recycled back into the process, byproducts and impurities are also recycled and accumulate over time. Each recycling step increases the total amount of byproducts and impurities in the cycle. To remove byproducts and impurities from the cycle, they need to be removed periodically along with the fructose-rich fraction, thus also removing valuable fructose. From an economic perspective, this is disadvantageous.

[0009] There is a need for a method to produce allulose from fructose that overcomes these shortcomings of the prior art.

[0010] Simulated moving bed (SMB) chromatography is known to those skilled in the art and has been used to prepare allulose and allulose-containing products (see, for example, N. Wagner et al., Org. Process Res. Dev. 2012, 16, 323-330; N. Wagner et al., Journal of Chromatography A, 1398 (2015) 47–56; N. Wagner et al., Angew. Chem. Int. Ed. 2015, 54, 4182-4186; N. Wagner et al., Chemical Engineering Science 137 (2015) 423-435; X. Wen et al., Process Biochemistry, 2022, Vol. 119, pp. 29-38; US 4,692,514, US 4,880,920, US 2010 0213130, US...). 2017 0313734, US2019 0177351, US 2019 0315790 (WO 2018 / 087261 A1), US 2019 0315791, US20200157131, US 2020 0172945, US 2020 0377540, US2020 0385415, US2020 0407389, US2021 0324434, US2022 0315618, US2022 0380400, US2023 0046104 and US20230058087).

[0011] WO 2021 146134 A1 relates to a method comprising separating a mixture of allulose, fructose, glucose and glucose oligosaccharides, wherein the separation comprises using simulated moving bed chromatography and recovering allulose in high purity and high yield.

[0012] WO 2022 239027 A1 relates to systems and methods for purifying D-allulose and / or fructose from binary mixtures.

[0013] EP 3 553 069 A1 relates to a method for preparing allulose by utilizing fructose residue obtained during the separation of allulose conversion products by high-purity chromatography.

[0014] FR 3 061 413 A1 relates to a method for producing D-allulose crystals, which is capable of continuous operation and yields high production rates. It also relates to the use of a nanofiltration device during the production of D-allulose crystals to improve the yield and / or quality of the resulting crystals.

[0015] US 11 401 292 B2 relates to a method for preparing a crystalline functional sweetener, wherein the method improves the crystallization yield and increases the particle size by controlling the content or generation of impurities in the solution used to prepare the crystals.

[0016] The object of this invention is to provide a superior method for preparing allulose from fructose compared to existing technologies. This method allows for the economical production of allulose products with high purity on an industrial scale. The handling of valuable substances, such as residual fructose, should be minimized.

[0017] This objective has been achieved by the subject matter of the patent claims.

[0018] A first aspect of the present invention relates to a method for preparing an allulose product, comprising the following steps: (a) Providing a starting composition comprising (α) fructose and (β) Optionally one or more impurities and / or glucose and / or sucrose; (b) Contacting the starting composition with allulose-3-epimerase to convert fructose to allulose, thereby obtaining a crude product comprising: (α) Allulose, (β) fructose and (γ) One or more impurities and / or glucose and / or sucrose; (c) Optionally, the crude product is subjected to one or more pre-purification measures to obtain a pre-purified product containing the following substances: (α) Allulose, (β) fructose and (γ) One or more impurities and / or glucose and / or sucrose; (d) Separating the crude product or the pre-purified product by chromatography. (α) One or more allulose-rich fractions (extracts), each fraction having an allulose content of at least 85% by weight relative to the dry solids content of the allulose-rich fraction; (β) A fructose-rich fraction (extraction residue) having a fructose content of at least 85% by weight relative to the dry solids content of the fructose-rich fraction; and (γ) Optionally, a scavenging fraction rich in one or more impurities and / or glucose and / or sucrose; (e) Optionally, the fructose-rich fraction is subjected to one or more concentration and / or purification measures to obtain a concentrated and / or purified fructose-rich fraction having a fructose content of at least 85% by weight relative to the dry solids content of the concentrated and / or purified fructose-rich fraction. (f) Recycle the fructose-rich fraction or the concentrated and / or purified fructose-rich fraction to step (a) or (b); The one or more impurities mentioned therein are any organic compounds other than allulose, fructose, glucose and sucrose.

[0019] The method according to the present invention includes steps (a), (b), (d), and (f), and optionally further includes (c) and / or (e). In a preferred embodiment, the method includes steps (a), (b), (c), (d), and (f); or (a), (b), (d), (e), and (f); or (a), (b), (c), (d), (e), and (f).

[0020] Preferably, these method steps are performed in alphabetical order.

[0021] In a preferred embodiment, the method is performed in batches.

[0022] In other preferred embodiments, the method is performed in a semi-intermittent manner.

[0023] In a further preferred embodiment, the method is performed continuously. Those skilled in the art will recognize that in these cases, one or more of the method steps can be performed simultaneously, or at least partially simultaneously.

[0024] Unless otherwise expressly stated, all percentages are by weight. Unless otherwise expressly stated, all percentages are relative to the dry solids content of the corresponding process flow.

[0025] For the purposes of this specification, and / or "meaning" Or "、" or "or" as well as ",Right now" A and / or B "meaning" It's either A or not B. ",or" It's either B or not A. ",or" A and B ".

[0026] Unless otherwise explicitly stated, all carbohydrates are present in the D configuration. While the L configuration is also hypothesized, the D configuration is preferred.

[0027] Unless otherwise explicitly stated, impurities refer to any organic compound other than allulose, fructose, glucose and sucrose.

[0028] In a preferred embodiment, in step (d), the crude product or pre-purified product is separated by chromatography into... (α) One or more allulose-rich fractions (extracts), each fraction having an allulose content of at least 85% by weight relative to the dry solids content of the allulose-rich fraction; (β) A fructose-rich fraction (extraction residue) having a fructose content of at least 85% by weight relative to the dry solids content of the fructose-rich fraction; and (γ) A scavenging fraction rich in one or more impurities and / or glucose and / or sucrose, i.e., a scavenging fraction is required.

[0029] In a preferred embodiment, the allulose product is solid, preferably at least partially crystalline.

[0030] In other preferred embodiments, the allulose product is a liquid, preferably a syrup.

[0031] In step (a) of the method according to the invention, a starting composition is provided comprising (α) fructose and (β) optional one or more impurities and / or glucose and / or sucrose.

[0032] Preferably, the fructose content of the starting composition is at least 40% by weight, preferably at least 60% by weight, more preferably at least 70% by weight, even more preferably at least 80% by weight, even more preferably at least 90% by weight, most preferably at least 95% by weight, and particularly at least 98% by weight, relative to the dry solids content of the starting composition.

[0033] Preferably, the starting composition comprises glucose.

[0034] Preferably, the glucose content of the starting composition is at most 8.0% by weight, preferably at most 7.0% by weight, more preferably at most 6.0% by weight, even more preferably at most 5.0% by weight, even more preferably at most 4.0% by weight, most preferably at most 3.0% by weight, and particularly at most 2.0% by weight, relative to the dry solids content of the starting composition.

[0035] Preferably, the glucose content of the starting composition is at least 0.0001 wt%, more preferably at least 0.001 wt%, more preferably at least 0.01 wt%, even more preferably at least 0.1 wt%, even more preferably at least 0.2 wt%, most preferably at least 0.3 wt%, and particularly at least 0.4 wt%, relative to the dry solids content of the starting composition.

[0036] Preferably, the starting composition comprises sucrose.

[0037] Preferably, the sucrose content of the starting composition is at most 1.8% by weight, preferably at most 1.6% by weight, more preferably at most 1.4% by weight, even more preferably at most 1.2% by weight, even more preferably at most 1.0% by weight, most preferably at most 0.8% by weight, and particularly at most 0.6% by weight, relative to the dry solids content of the starting composition.

[0038] In step (b) of the method according to the invention, the starting composition provided in step (a) is contacted with allulose-3-epimerase to convert fructose into allulose, thereby obtaining a crude product comprising (α) allulose, (β) fructose and (γ) one or more impurities and / or glucose and / or sucrose.

[0039] Technicians are familiar with suitable allulose-3-epimerases and reaction conditions. Certain tagatose-3-epimerases can also be used (see, for example, S. Jiang et al.). Review on D-Allulose: In vivo Metabolism, Catalytic Mechanism, Engineering StrainConstruction, Bio- Production Technology , Front Bioeng Biotechnol. Feb 2020 3:8:26, 1-10).

[0040] In a preferred embodiment, at least one of one or more impurities is formed in step (b), for example as a byproduct of enzymatic catalytic conversion.

[0041] In a preferred embodiment, at least one of one or more impurities is formed in one or more steps following step (b), for example, during post-processing at high temperature.

[0042] Preferably, the one or more impurities include allulose dimer, allulose-fructobiose, allulose-glucose bisaccharide, allulose tetramer, and diallulose anhydride. (anhydride), levulinic acid, γ-hydroxyvalerate (GVA), furfural, hydroxymethylfurfural (HMF), 2,5-dimethylfuran, 2,5-furandicarboxylic acid (FDCA), 5-hydroxymethylfuran-2-carboxylic acid, 2,5-formylfurancarboxylic acid, 2,5-furandialdehyde, 2,5-bis-(hydroxy-methyl)furan, bis(5-formyl-2-furfural) ether, furan-2-carboxylic acid, furan-3-carboxylic acid, 5-hydroxyfurfural, 2,5-dihydro-2,5-dimethoxyfuran, (2R)-5-oxotetrahydro-2-furancarboxylic acid, bis(5-methylfurfural) ether, 5,5'-methylene-bis(furan-2-carboxylic acid) or any combination thereof.

[0043] Preferably, the one or more impurities include lactic acid, maltol, furanol, allosone, glucone, 1-deoxyglucone, 3-deoxyglucone, 3-deoxygalactone, formic acid, acetic acid, propionic acid, glyoxal, or any combination thereof.

[0044] Preferably, the one or more impurities include 2,3-butanedione, acetaldehyde, 2-keto-D-glucose (glucose ketone), 3-deoxyglucose ketone, or any combination thereof.

[0045] In a particularly preferred embodiment, one or more impurities include 2,3-butanedione (diacetyl), namely CH3C(=O)C(C=O)CH3.

[0046] In a particularly preferred embodiment, the one or more impurities include acetaldehyde, i.e., CH3C(=O)H.

[0047] In a particularly preferred embodiment, the one or more impurities include 2-keto-D-glucose (glucone), i.e. .

[0048] In a particularly preferred embodiment, the one or more impurities include allone, i.e. .

[0049] In a particularly preferred embodiment, the one or more impurities include 3-deoxyglucosone, i.e. .

[0050] Preferably, the total impurity content of the crude product is at least 0.0001 wt%, more preferably at least 0.001 wt%, more preferably at least 0.01 wt%, even more preferably at least 0.1 wt%, even more preferably at least 0.2 wt%, most preferably at least 0.3 wt%, and particularly at least 0.5 wt%, relative to the dry solids content of the crude product.

[0051] Preferably, the total impurity content of the crude product is at most 7.0% by weight, more preferably at most 6.0% by weight, more preferably at most 5.0% by weight, even more preferably at most 4.0% by weight, even more preferably at most 3.0% by weight, most preferably at most 2.0% by weight, and particularly at most 1.0% by weight, relative to the dry solids content of the crude product.

[0052] Preferably, the allulose content of the crude product is at least 15% by weight, more preferably at least 23% by weight, more preferably at least 32% by weight, even more preferably at least 40% by weight, even more preferably at least 48% by weight, most preferably at least 57% by weight, and particularly at least 65% by weight, relative to the dry solids content of the crude product.

[0053] Preferably, the fructose content of the crude product is at most 85% by weight, more preferably at most 77% by weight, more preferably at most 68% by weight, even more preferably at most 60% by weight, even more preferably at most 52% by weight, most preferably at most 44% by weight, and particularly at most 35% by weight, relative to the dry solids content of the crude product.

[0054] Preferably, the glucose content of the crude product is at most 8.0% by weight, more preferably at most 7.0% by weight, more preferably at most 6.0% by weight, even more preferably at most 5.0% by weight, even more preferably at most 4.0% by weight, most preferably at most 3.0% by weight, and particularly at most 2.0% by weight, relative to the dry solids content of the crude product.

[0055] Preferably, the sucrose content of the crude product is at most 5.00% by weight, more preferably at most 4.25% by weight, more preferably at most 3.50% by weight, even more preferably at most 2.75% by weight, even more preferably at most 2.00% by weight, most preferably at most 1.25% by weight, and particularly at most 0.50% by weight, relative to the dry solids content of the crude product.

[0056] Preferably, the hydroxymethylfurfural (HMF) content of the crude product is in the range of 1 to 10,000 ppmw, more preferably 1 to 8,000 ppmw, more preferably 1 to 6,000 ppmw, even more preferably 1 to 4,000 ppmw, even more preferably 1 to 2,000 ppmw, most preferably 1 to 1,000 ppmw, and particularly in the range of 1 to 500 ppmw, relative to the dry solids content of the crude product.

[0057] Preferably, the 2,3-butanedione content of the crude product is in the range of 1 to 10,000 ppmw, more preferably 1 to 8,000 ppmw, more preferably 1 to 6,000 ppmw, even more preferably 1 to 4,000 ppmw, even more preferably 1 to 2,000 ppmw, most preferably 1 to 1,000 ppmw, and particularly in the range of 1 to 500 ppmw, relative to the dry solids content of the crude product.

[0058] Preferably, the acetaldehyde content of the crude product is in the range of 1 to 10,000 ppmw, more preferably 1 to 8,000 ppmw, more preferably 1 to 6,000 ppmw, even more preferably 1 to 4,000 ppmw, even more preferably 1 to 2,000 ppmw, most preferably 1 to 1,000 ppmw, and particularly in the range of 1 to 500 ppmw, relative to the dry solids content of the crude product.

[0059] Preferably, the 2-keto-D-glucose content of the crude product is in the range of 1 to 10,000 ppmw, more preferably 1 to 8,000 ppmw, more preferably 1 to 6,000 ppmw, even more preferably 1 to 4,000 ppmw, even more preferably 1 to 2,000 ppmw, most preferably 1 to 1,000 ppmw, and particularly in the range of 1 to 500 ppmw, relative to the dry solids content of the crude product.

[0060] Preferably, the allolone content of the crude product is in the range of 1 to 10,000 ppmw, more preferably 1 to 8,000 ppmw, more preferably 1 to 6,000 ppmw, even more preferably 1 to 4,000 ppmw, even more preferably 1 to 2,000 ppmw, most preferably 1 to 1,000 ppmw, and particularly in the range of 1 to 500 ppmw, relative to the dry solids content of the crude product.

[0061] Preferably, the 3-deoxyglucone content of the crude product is in the range of 1 to 10,000 ppmw, more preferably 1 to 8,000 ppmw, more preferably 1 to 6,000 ppmw, even more preferably 1 to 4,000 ppmw, even more preferably 1 to 2,000 ppmw, most preferably 1 to 1,000 ppmw, and particularly in the range of 1 to 500 ppmw, relative to the dry solids content of the crude product.

[0062] In optional step (c) of the method according to the invention, the crude product obtained in step (b) is subjected to one or more pre-purification measures to obtain a pre-purified product, said pre-purified product comprising (α) allulose, (β) fructose and (γ) one or more impurities and / or glucose and / or sucrose.

[0063] Preferably, the one or more pre-purification measures include filtration, preferably ultrafiltration.

[0064] Technicians are familiar with suitable methods for filtration (including ultrafiltration), and suitable membranes are commercially available. Typical membrane and pore filter separation limits are between 0.1 and 0.01 µm.

[0065] Preferably, the one or more pre-purification measures include demineralization and / or decolorization (discoloration).

[0066] Those skilled in the art are aware of suitable methods for demineralization, including but not limited to ion exchange chromatography. Suitable ion exchange resins are commercially available.

[0067] Technicians are also aware of suitable methods for decolorization, including but not limited to adsorption. Suitable adsorbents such as activated carbon are commercially available.

[0068] In step (d) of the method according to the invention, the crude product obtained in step (b) or the pre-purified product obtained in optional step (c) is separated by chromatography into... (α) One or more allulose-rich fractions, each fraction having an allulose content of at least 85% by weight relative to the dry solids content of the allulose-rich fractions; (β) A fructose-rich fraction having a fructose content of at least 85% by weight relative to the dry solids content of the fructose-rich fraction; and (γ) Optionally, a scavenging fraction rich in one or more impurities and / or glucose and / or sucrose.

[0069] In a preferred embodiment, the crude product obtained in step (b) of the chromatographic separation or the pre-purified product obtained in step (c) is... (α) The dry solids content (dry matter content) relative to the total weight of the crude product and the pre-purified product, respectively, is within the following ranges: 55.0 ± 15.0 wt%, preferably 55.0 ± 13.0 wt%, more preferably 55.0 ± 11.0 wt%, even more preferably 55.0 ± 9.0 wt%, even more preferably 55.0 ± 7.0 wt%, even more preferably 55.0 ± 6.0 wt%, most preferably 55.0 ± 5.0 wt%, and particularly 55.0 ± 4.0 wt%; and / or (β) The allulose content, relative to the dry solids content of the crude product and the pre-purified product, is within the following ranges: 30.0 ± 12.0 wt%, preferably 30.0 ± 11.0 wt%, more preferably 30.0 ± 10.0 wt%, even more preferably 30.0 ± 9.0 wt%, even more preferably 30.0 ± 8.0 wt%, even more preferably 30.0 ± 7.0 wt%, most preferably 30.0 ± 6.0 wt%, and particularly 30.0 ± 5.0 wt%; and / or (γ) The fructose content, relative to the dry solids content of the crude product and the pre-purified product, is within the following ranges: 65.0 ± 12.0 wt%, preferably 65.0 ± 11.0 wt%, more preferably 65.0 ± 10.0 wt%, even more preferably 65.0 ± 9.0 wt%, even more preferably 65.0 ± 8.0 wt%, even more preferably 65.0 ± 7.0 wt%, most preferably 65.0 ± 6.0 wt%, and particularly 65.0 ± 5.0 wt%; and / or (δ) The glucose content relative to the dry solids content of the crude and pre-purified products is in the following range: 1.7 ± 1.7 wt%, preferably 1.7 ± 1.5 wt%, more preferably 1.7 ± 1.3 wt%, even more preferably 1.7 ± 1.1 wt%, even more preferably 1.7 ± 0.9 wt%, even more preferably 1.7 ± 0.7 wt%, most preferably 1.7 ± 0.5 wt%, and particularly 1.7 ± 0.3 wt%; and / or (ε) The sucrose content relative to the dry solids content of the crude product and the pre-purified product is in the following range: 0.50 ± 0.50 wt%, preferably 0.50 ± 0.45 wt%, more preferably 0.50 ± 0.40 wt%, even more preferably 0.50 ± 0.35 wt%, even more preferably 0.50 ± 0.30 wt%, even more preferably 0.50 ± 0.25 wt%, most preferably 0.50 ± 0.20 wt%, and particularly 0.50 ± 0.15 wt%.

[0070] Preferably, chromatographic separation provides - One or more allulose-rich fractions (extracts), wherein, relative to the dry solids content of the one or more allulose-rich fractions, the allulose content is in the range of 90 to 100% by weight, the fructose content is in the range of 0 to 5% by weight (50,000 ppmw), and the glucose content is in the range of 0 to 0.5% by weight (5,000 ppmw). - A fructose-rich fraction (extraction residue), wherein, relative to the dry solids content of the fructose-rich fraction, the fructose content is in the range of 90 to 100% by weight, the allulose content is in the range of 0 to 5% by weight (50,000 ppmw), and the glucose content is in the range of 0 to 1.5% by weight (15,000 ppmw).

[0071] Preferably, the chromatographic separation includes at least one simulated moving bed chromatography (SMB), more preferably sequential simulated moving bed chromatography (SSMB). Simulated moving bed chromatography is common and general knowledge (see, for example, A.E. Rodrigues et al.). Simulated Moving Bed Technology - Principles, Design and Process Applications(Elsevier, 2015). Sequential Simulated Moving Bed (SSMB) technology is an improved SMB technology that divides the switching cycle into three sub-steps, thereby generating different flow patterns to reduce solvent consumption at high purity.

[0072] Suitable stationary phases for SMBs are known to those skilled in the art. Preferred stationary phases are calcium-type strong acid ion exchange resins. Suitable resins can be, for example, from Purolite. ® Obtained commercially from corporations or Dow Chemicals, such as DOWEX ® 50 WX4-400.

[0073] like Figure 3 As shown, SMB is characterized by the ratio of freshwater volume to feed volume, i.e., the water-to-feed ratio. According to the present invention, a lower water-to-feed ratio (v / v) for SMB is desirable.

[0074] Preferably, the water-to-feed ratio (v / v) of the SMB is at most 4.0, more preferably at most 3.7, even more preferably at most 3.4, even more preferably at most 3.1, even more preferably at most 2.8, most preferably at most 2.5, and particularly at most 2.2.

[0075] Preferably, the water-to-feed ratio (v / v) of the SMB is at least 0.8, more preferably at least 0.9, even more preferably at least 1.0, even more preferably at least 1.1, even more preferably at least 1.2, most preferably at least 1.3, and particularly at least 1.4.

[0076] A water-to-feed ratio (v / v) of SMB in the range of 1.5 to 3.6 is particularly preferred. In a preferred embodiment, the water-to-feed ratio (v / v) of SMB is in the range of 1.5 to 2.0. In a preferred embodiment, the water-to-feed ratio (v / v) of SMB is in the range of 2.0 to 3.6.

[0077] In addition, such as Figure 3 As shown, SMB is characterized by the ratio of the volume of the extract (product) to the volume of the raffinate, i.e., the extract to raffinate ratio. The extract to raffinate ratio corresponds to the ratio of the volume of the allulose-rich fraction to the volume of the fructose-rich fraction.

[0078] Preferably, the extract to residue ratio (v / v) of the SMB is at most 1.6, more preferably at most 1.5, even more preferably at most 1.4, even more preferably at most 1.3, even more preferably at most 1.2, most preferably at most 1.1, and particularly at most 1.0.

[0079] Preferably, the extract to residue ratio (v / v) of the SMB is at least 0.25, more preferably at least 0.30, even more preferably at least 0.35, even more preferably at least 0.40, even more preferably at least 0.45, most preferably at least 0.50, and particularly at least 0.55.

[0080] In a preferred embodiment, the extract to residue ratio (v / v) of the SMB is in the following range: 0.64±0.40, preferably 0.64±0.35, more preferably 0.64±0.30, even more preferably 0.64±0.25, even more preferably 0.64±0.20, even more preferably 0.64±0.15, most preferably 0.64±0.10, and particularly preferably 0.64±0.05.

[0081] In a further preferred embodiment, the extract-to-residue ratio (v / v) of the SMB is in the following range: 0.88±0.40, preferably 0.88±0.35, more preferably 0.88±0.30, even more preferably 0.88±0.25, even more preferably 0.88±0.20, even more preferably 0.88±0.15, most preferably 0.88±0.10, and particularly preferably 0.88±0.05.

[0082] In other preferred embodiments, the extract-to-residue ratio (v / v) of the SMB is in the range of: 0.99±0.40, preferably 0.99±0.35, more preferably 0.99±0.30, even more preferably 0.99±0.25, even more preferably 0.99±0.20, even more preferably 0.99±0.15, most preferably 0.99±0.10, and particularly preferably 0.99±0.05.

[0083] Preferably, the purity of allulose in the fraction rich in allulose in the extract is at least 93%, more preferably at least 94%, even more preferably at least 95%, even more preferably at least 96%, even more preferably at least 97%, most preferably at least 98%, and particularly at least 99%.

[0084] A purity of allulose in the range of 95 to 99% by weight is particularly preferred.

[0085] Preferably, the purity of allulose is determined by HPLC according to ICUMSA GS3-50.

[0086] SMB further characterizes this by the recovery rate of allulose, which is the amount of allulose in the extract (product) relative to the amount of allulose in the feed.

[0087] Preferably, the recovery rate of allulose is at least 79%, more preferably at least 80%, even more preferably at least 81%, even more preferably at least 82%, even more preferably at least 83%, most preferably at least 84%, and particularly at least 85%.

[0088] Preferably, the recovery rate of allulose is at least 86%, more preferably at least 87%, even more preferably at least 88%, still more preferably at least 89%, even more preferably at least 90%, most preferably at least 91%, and particularly at least 92%.

[0089] Preferably, the recovery rate of allulose is at least 93%, more preferably at least 94%, even more preferably at least 95%, even more preferably at least 96%, even more preferably at least 97%, most preferably at least 98%, and particularly at least 99%.

[0090] In a preferred embodiment, the method according to the invention includes a single simulated moving bed (SMB) chromatography, preferably a single sequential simulated moving bed (SSMB) chromatography.

[0091] Preferably, in step (d), the crude product obtained in step (b) or optionally the pre-purified product obtained in step (c) is then separated by chromatography into... (α) An allulose-rich fraction having an allulose content of at least 85% by weight relative to the dry solids content of the allulose-rich fraction; (β) A fructose-rich fraction having a fructose content of at least 85% by weight relative to the dry solids content of the fructose-rich fraction; and (γ) A scavenging fraction rich in one or more impurities and / or glucose and / or sucrose.

[0092] In the flow direction of the crude product obtained in step (b) or optionally the pre-purified product obtained in step (c), the allulose-rich fraction is preferably separated downstream of the fructose-rich fraction.

[0093] In a preferred embodiment, the scavenging fraction is separated upstream of the fructose-rich fraction by chromatography, and the allulose-rich fraction is separated downstream of the fructose-rich fraction (scavenging -> fructose -> allulose).

[0094] In other preferred embodiments, the fructose-rich fraction is separated upstream of the allulose-rich fraction by chromatography, and the scavenging fraction is separated downstream of the allulose-rich fraction (fructose -> allulose -> scavenging).

[0095] In a further preferred embodiment, the first scavenging fraction is separated by chromatography upstream of the fructose-rich fraction, the allulose-rich fraction is separated downstream of the fructose-rich fraction, and the second scavenging fraction is separated downstream of the allulose-rich fraction (first scavenging -> fructose -> allulose -> second scavenging).

[0096] When the scavenging fraction is separated upstream of the fructose-rich fraction, the flow rate of the scavenging fraction preferably reaches at most 9.0 wt% of the flow rate of the fructose-rich fraction, more preferably at most 8.0 wt%, even more preferably at most 7.0 wt%, even more preferably at most 6.0 wt%, even more preferably at most 5.0 wt%, most preferably at most 4.0 wt%, and particularly at most 3.0 wt%.

[0097] When the scavenging fraction is separated downstream of the allulose-rich fraction, the flow rate of the scavenging fraction preferably reaches at most 9.0 wt% of the flow rate of the allulose-rich fraction, more preferably at most 8.0 wt%, even more preferably at most 7.0 wt%, even more preferably at most 6.0 wt%, even more preferably at most 5.0 wt%, most preferably at most 4.0 wt%, and particularly at most 3.0 wt%.

[0098] In other preferred embodiments, the method according to the invention comprises two simulated moving bed (SMB) chromatograms, preferably two sequential simulated moving bed (SSMB) chromatograms.

[0099] Preferably, step (d) includes the following sub-steps: (d1) The crude product or the pre-purified product is separated by chromatography into (α) a first allulose-rich fraction and (β) an intermediate fraction rich in (i) fructose and (ii) one or more impurities and / or glucose and / or sucrose. (d2) The intermediate fraction was separated by chromatography into (α) a second allulose-rich fraction; (β) a fructose-rich fraction; and (γ) a scavenging fraction; and (d3) Optionally, the first allulose-rich fraction and the second allulose-rich fraction are combined with each other.

[0100] In a preferred embodiment, in the flow direction of the crude product obtained in step (b) or optionally the pre-purified product obtained in step (c), in sub-step (d1), the first allulose-rich fraction is preferably separated downstream of the intermediate fraction.

[0101] In a preferred embodiment, the scavenging fraction is separated by chromatography upstream of the intermediate fraction, and the first allulose-rich fraction is separated downstream of the intermediate fraction (scavenging -> intermediate -> first allulose).

[0102] In other preferred embodiments, the intermediate fraction is separated upstream of the first allulose-rich fraction by chromatography, and the scavenging fraction is separated downstream of the first allulose-rich fraction (intermediate -> first allulose -> scavenging).

[0103] In a further preferred embodiment, the first scavenging fraction is separated by chromatography upstream of the intermediate fraction, the first allulose-rich fraction is separated downstream of the intermediate fraction, and the second scavenging fraction is separated downstream of the first allulose-rich fraction (first scavenging -> intermediate fraction -> first allulose -> second scavenging).

[0104] When the clearing stage is separated upstream of the intermediate stage, the flow rate of the clearing stage preferably reaches at most 9.0 wt% of the flow rate of the intermediate stage, preferably at most 8.0 wt%, more preferably at most 7.0 wt%, even more preferably at most 6.0 wt%, even more preferably at most 5.0 wt%, most preferably at most 4.0 wt%, and particularly at most 3.0 wt%.

[0105] When the scavenging fraction is separated downstream of the first allulose-rich fraction, the flow rate of the scavenging fraction preferably reaches at most 9.0 wt% of the flow rate of the first allulose-rich fraction, preferably at most 8.0 wt%, more preferably at most 7.0 wt%, even more preferably at most 6.0 wt%, even more preferably at most 5.0 wt%, most preferably at most 4.0 wt%, and particularly at most 3.0 wt%.

[0106] In other preferred embodiments, in the flow direction of the crude product obtained in step (b) or the pre-purified product obtained in optional step (c), the second allulose-rich fraction is separated downstream of the fructose-rich fraction in sub-step (d2).

[0107] In a preferred embodiment, the scavenging fraction is separated by chromatography upstream of the fructose-rich fraction, and the second allulose-rich fraction is separated downstream of the fructose-rich fraction (scavenging -> fructose -> second allulose).

[0108] In other preferred embodiments, the fructose-rich fraction is separated upstream of the second allulose-rich fraction by chromatography, and the scavenging fraction is separated downstream of the second allulose-rich fraction (fructose -> second allulose -> scavenging).

[0109] In a further preferred embodiment, the first scavenging fraction is separated upstream of the fructose-rich fraction by chromatography, the second allulose-rich fraction is separated downstream of the fructose-rich fraction, and the second scavenging fraction is separated downstream of the second allulose-rich fraction (first scavenging -> fructose -> second allulose -> second scavenging).

[0110] When the scavenging fraction is separated upstream of the fructose-rich fraction, the flow rate of the scavenging fraction preferably reaches at most 9.0 wt% of the flow rate of the fructose-rich fraction, more preferably at most 8.0 wt%, even more preferably at most 7.0 wt%, even more preferably at most 6.0 wt%, even more preferably at most 5.0 wt%, most preferably at most 4.0 wt%, and particularly at most 3.0 wt%.

[0111] When the scavenging fraction is separated downstream of the second allulose-rich fraction, the flow rate of the scavenging fraction preferably reaches at most 9.0 wt% of the flow rate of the second allulose-rich fraction, preferably at most 8.0 wt%, even more preferably at most 7.0 wt%, even more preferably at most 6.0 wt%, even more preferably at most 5.0 wt%, most preferably at most 4.0 wt%, and particularly at most 3.0 wt%.

[0112] Regardless of whether the method includes single or two simulated moving bed chromatography, the fractions separated from each other by chromatography have a preferred composition as defined below: Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have an allulose content of at least 87.5% by weight, preferably at least 90.0% by weight, more preferably at least 92.5% by weight, even more preferably at least 95.0% by weight, even more preferably at least 97.5% by weight, most preferably at least 98.5% by weight, and particularly at least 99.0% by weight.

[0113] Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a fructose content of up to 12.5% ​​by weight, preferably up to 7.5% by weight, more preferably up to 5.0% by weight, even more preferably up to 2.5% by weight, even more preferably up to 1.0% by weight, most preferably up to 0.1% by weight, and particularly up to 0.01% by weight.

[0114] Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a total impurity content of up to 2.0% by weight, preferably up to 1.8% by weight, more preferably up to 1.6% by weight, even more preferably up to 1.4% by weight, and still more preferably up to 1.2% by weight.

[0115] Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a total impurity content of up to 1.0% by weight, preferably up to 0.8% by weight, more preferably up to 0.6% by weight, even more preferably up to 0.4% by weight, even more preferably up to 0.2% by weight, most preferably up to 0.1% by weight, and particularly up to 0.01% by weight.

[0116] Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a glucose content of up to 3.0% by weight, preferably up to 2.0% by weight, more preferably up to 1.5% by weight, even more preferably up to 1.0% by weight, even more preferably up to 0.5% by weight, most preferably up to 0.1% by weight, and particularly up to 0.01% by weight.

[0117] Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a sucrose content of up to 3.0% by weight, preferably up to 2.0% by weight, more preferably up to 1.5% by weight, even more preferably up to 1.0% by weight, even more preferably up to 0.5% by weight, most preferably up to 0.1% by weight, and particularly up to 0.01% by weight.

[0118] Preferably, relative to the total weight of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a dry solids content of at least 4.0% by weight, preferably at least 6.0% by weight, more preferably at least 8.0% by weight, even more preferably at least 10% by weight, even more preferably at least 12% by weight, even more preferably at least 14% by weight, most preferably at least 16% by weight, and particularly at least 18% by weight.

[0119] Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a hydroxymethylfurfural (HMF) content of up to 10,000 ppmw, preferably up to 8,000 ppmw, more preferably up to 6,000 ppmw, even more preferably up to 4,000 ppmw, even more preferably up to 3,000 ppmw, most preferably up to 2,000 ppmw, and particularly up to 1,500 ppmw. Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a hydroxymethylfurfural (HMF) content of up to 1,000 ppmw, preferably up to 800 ppmw, more preferably up to 600 ppmw, even more preferably up to 400 ppmw, even more preferably up to 200 ppmw, most preferably up to 100 ppmw, and particularly up to 50 ppmw.

[0120] Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a 2,3-butanedione content of up to 10,000 ppmw, preferably up to 8,000 ppmw, more preferably up to 6,000 ppmw, even more preferably up to 4,000 ppmw, even more preferably up to 3,000 ppmw, most preferably up to 2,000 ppmw, and particularly up to 1,500 ppmw. Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a 2,3-butanedione content of up to 1,000 ppmw, preferably up to 800 ppmw, more preferably up to 600 ppmw, even more preferably up to 400 ppmw, even more preferably up to 200 ppmw, most preferably up to 100 ppmw, and particularly up to 50 ppmw.

[0121] Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have an acetaldehyde content of up to 10,000 ppmw, preferably up to 8,000 ppmw, more preferably up to 6,000 ppmw, even more preferably up to 4,000 ppmw, even more preferably up to 3,000 ppmw, most preferably up to 2,000 ppmw, and particularly up to 1,500 ppmw. Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have an acetaldehyde content of up to 1,000 ppmw, preferably up to 800 ppmw, more preferably up to 600 ppmw, even more preferably up to 400 ppmw, even more preferably up to 200 ppmw, most preferably up to 100 ppmw, and particularly up to 50 ppmw.

[0122] Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a 2-keto-D-glucose content of up to 10,000 ppmw, preferably up to 8,000 ppmw, more preferably up to 6,000 ppmw, even more preferably up to 4,000 ppmw, even more preferably up to 3,000 ppmw, most preferably up to 2,000 ppmw, and particularly up to 1,500 ppmw. Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a 2-keto-D-glucose content of up to 1,000 ppmw, preferably up to 800 ppmw, more preferably up to 600 ppmw, even more preferably up to 400 ppmw, even more preferably up to 200 ppmw, most preferably up to 100 ppmw, and particularly up to 50 ppmw.

[0123] Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have an allolone content of up to 10,000 ppmw, preferably up to 8,000 ppmw, more preferably up to 6,000 ppmw, even more preferably up to 4,000 ppmw, even more preferably up to 3,000 ppmw, most preferably up to 2,000 ppmw, and particularly up to 1,500 ppmw. Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have an allolone content of up to 1,000 ppmw, preferably up to 800 ppmw, more preferably up to 600 ppmw, even more preferably up to 400 ppmw, even more preferably up to 200 ppmw, most preferably up to 100 ppmw, and particularly up to 50 ppmw.

[0124] Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a 3-deoxyglucone content of up to 10,000 ppmw, preferably up to 8,000 ppmw, more preferably up to 6,000 ppmw, even more preferably up to 4,000 ppmw, even more preferably up to 3,000 ppmw, most preferably up to 2,000 ppmw, and particularly up to 1,500 ppmw. Preferably, relative to the dry solids content of one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a 3-deoxyglucone content of up to 1,000 ppmw, preferably up to 800 ppmw, more preferably up to 600 ppmw, even more preferably up to 400 ppmw, even more preferably up to 200 ppmw, most preferably up to 100 ppmw, and particularly up to 50 ppmw.

[0125] Preferably, the fructose content of the fructose-rich fraction is at least 70.0% by weight, more preferably at least 72.5% by weight, more preferably at least 75.0% by weight, even more preferably at least 77.5% by weight, and still more preferably at least 80.0% by weight, most preferably at least 82.5% by weight, and particularly at least 85.0% by weight, relative to the dry solids content of the fructose-rich fraction.

[0126] Preferably, the fructose content of the fructose-rich fraction is at least 87.5% by weight, more preferably at least 90.0% by weight, more preferably at least 92.5% by weight, even more preferably at least 95.0% by weight, even more preferably at least 97.5% by weight, most preferably at least 98.5% by weight, and particularly at least 99.0% by weight, relative to the dry solids content of the fructose-rich fraction.

[0127] Preferably, the allulose content of the fructose-rich fraction is at most 12.5% ​​by weight, more preferably at most 7.5% by weight, more preferably at most 5.0% by weight, even more preferably at most 2.5% by weight, even more preferably at most 1.0% by weight, most preferably at most 0.1% by weight, and particularly at most 0.01% by weight, relative to the dry solids content of the fructose-rich fraction.

[0128] Preferably, the total impurity content of the fructose-rich fraction is at most 4.5% by weight, more preferably at most 4.0% by weight, more preferably at most 3.5% by weight, even more preferably at most 3.0% by weight, even more preferably at most 2.5% by weight, most preferably at most 2.0% by weight, and particularly at most 1.5% by weight, relative to the dry solids content of the fructose-rich fraction.

[0129] Preferably, the total impurity content of the fructose-rich fraction is at most 1.0 wt%, more preferably at most 0.8 wt%, more preferably at most 0.6 wt%, even more preferably at most 0.4 wt%, even more preferably at most 0.2 wt%, most preferably at most 0.1 wt%, and particularly at most 0.01 wt%, relative to the dry solids content of the fructose-rich fraction.

[0130] Preferably, the glucose content of the fructose-rich fraction is at most 3.0% by weight, more preferably at most 2.0% by weight, more preferably at most 1.5% by weight, even more preferably at most 1.0% by weight, even more preferably at most 0.5% by weight, most preferably at most 0.1% by weight, and particularly at most 0.01% by weight, relative to the dry solids content of the fructose-rich fraction.

[0131] Preferably, the sucrose content of the fructose-rich fraction is at most 3.0% by weight, more preferably at most 2.0% by weight, more preferably at most 1.5% by weight, even more preferably at most 1.0% by weight, even more preferably at most 0.5% by weight, most preferably at most 0.1% by weight, and particularly at most 0.01% by weight, relative to the dry solids content of the fructose-rich fraction.

[0132] Preferably, the dry solids content of the fructose-rich fraction (preferably the second scavenging fraction) is at least 5.0% by weight, preferably at least 10% by weight, more preferably at least 15% by weight, even more preferably at least 20% by weight, even more preferably at least 25% by weight, even more preferably at least 30% by weight, most preferably at least 35% by weight, and particularly at least 40% by weight, relative to the total weight of the fructose-rich fraction.

[0133] Preferably, the hydroxymethylfurfural (HMF) content of the fructose-rich fraction is at most 10,000 ppmw, more preferably at most 8,000 ppmw, more preferably at most 6,000 ppmw, even more preferably at most 4,000 ppmw, even more preferably at most 3,000 ppmw, most preferably at most 2,000 ppmw, and particularly at most 1,500 ppmw, relative to the dry solids content of the fructose-rich fraction. Preferably, the hydroxymethylfurfural (HMF) content of the fructose-rich fraction is at most 1,000 ppmw, more preferably at most 800 ppmw, more preferably at most 600 ppmw, even more preferably at most 400 ppmw, even more preferably at most 200 ppmw, most preferably at most 100 ppmw, and particularly at most 50 ppmw, relative to the dry solids content of the fructose-rich fraction.

[0134] Preferably, the content of 2,3-butanedione in the fructose-rich fraction is at most 10,000 ppmw, more preferably at most 8,000 ppmw, more preferably at most 6,000 ppmw, even more preferably at most 4,000 ppmw, even more preferably at most 3,000 ppmw, most preferably at most 2,000 ppmw, and particularly at most 1,500 ppmw, relative to the dry solids content of the fructose-rich fraction. Preferably, the content of 2,3-butanedione in the fructose-rich fraction is at most 1,000 ppmw, more preferably at most 800 ppmw, more preferably at most 600 ppmw, even more preferably at most 400 ppmw, even more preferably at most 200 ppmw, most preferably at most 100 ppmw, and particularly at most 50 ppmw, relative to the dry solids content of the fructose-rich fraction.

[0135] Preferably, the acetaldehyde content of the fructose-rich fraction is at most 10,000 ppmw, more preferably at most 8,000 ppmw, more preferably at most 6,000 ppmw, even more preferably at most 4,000 ppmw, even more preferably at most 3,000 ppmw, most preferably at most 2,000 ppmw, and particularly at most 1,500 ppmw, relative to the dry solids content of the fructose-rich fraction. Preferably, the acetaldehyde content of the fructose-rich fraction is at most 1,000 ppmw, more preferably at most 800 ppmw, more preferably at most 600 ppmw, even more preferably at most 400 ppmw, even more preferably at most 200 ppmw, most preferably at most 100 ppmw, and particularly at most 50 ppmw, relative to the dry solids content of the fructose-rich fraction.

[0136] Preferably, the 2-keto-D-glucose content of the fructose-rich fraction is at most 10,000 ppmw, more preferably at most 8,000 ppmw, more preferably at most 6,000 ppmw, even more preferably at most 4,000 ppmw, even more preferably at most 3,000 ppmw, most preferably at most 2,000 ppmw, and particularly at most 1,500 ppmw, relative to the dry solids content of the fructose-rich fraction. Preferably, the 2-keto-D-glucose content of the fructose-rich fraction is at most 1,000 ppmw, more preferably at most 800 ppmw, more preferably at most 600 ppmw, even more preferably at most 400 ppmw, even more preferably at most 200 ppmw, most preferably at most 100 ppmw, and particularly at most 50 ppmw, relative to the dry solids content of the fructose-rich fraction.

[0137] Preferably, the allone content of the fructose-rich fraction is at most 10,000 ppmw, more preferably at most 8,000 ppmw, more preferably at most 6,000 ppmw, even more preferably at most 4,000 ppmw, even more preferably at most 3,000 ppmw, most preferably at most 2,000 ppmw, and particularly at most 1,500 ppmw, relative to the dry solids content of the fructose-rich fraction. Preferably, the allone content of the fructose-rich fraction is at most 1,000 ppmw, more preferably at most 800 ppmw, more preferably at most 600 ppmw, even more preferably at most 400 ppmw, even more preferably at most 200 ppmw, most preferably at most 100 ppmw, and particularly at most 50 ppmw, relative to the dry solids content of the fructose-rich fraction.

[0138] Preferably, the 3-deoxyglucone content of the fructose-rich fraction is at most 10,000 ppmw, more preferably at most 8,000 ppmw, more preferably at most 6,000 ppmw, even more preferably at most 4,000 ppmw, even more preferably at most 3,000 ppmw, most preferably at most 2,000 ppmw, and particularly at most 1,500 ppmw, relative to the dry solids content of the fructose-rich fraction. Preferably, the 3-deoxyglucone content of the fructose-rich fraction is at most 1,000 ppmw, more preferably at most 800 ppmw, more preferably at most 600 ppmw, even more preferably at most 400 ppmw, even more preferably at most 200 ppmw, most preferably at most 100 ppmw, and particularly at most 50 ppmw, relative to the dry solids content of the fructose-rich fraction.

[0139] It is envisioned that the total impurity content of the removed fraction may be higher than the total impurity content of one or more allulose-rich fractions.

[0140] It is envisioned that the total impurity content of the purified fraction can be higher than that of the fructose-rich fraction.

[0141] Preferably, the total impurity content of the removal fraction is at least 0.001 wt%, more preferably at least 0.01 wt%, more preferably at least 0.1 wt%, even more preferably at least 0.5 wt%, even more preferably at least 1.0 wt%, most preferably at least 1.5 wt%, and particularly at least 2.0 wt%, relative to the dry solids content of the removal fraction.

[0142] Preferably, the allulose content of the scavenging fraction is at most 5.0 wt%, preferably at most 3.5 wt%, more preferably at most 2.0 wt%, even more preferably at most 1.0 wt%, even more preferably at most 0.5 wt%, most preferably at most 0.1 wt%, and particularly at most 0.01 wt%, relative to the dry solids content of the scavenging fraction.

[0143] Preferably, the fructose content of the scavenging fraction is at most 95% by weight, more preferably at most 90% by weight, more preferably at most 85% by weight, even more preferably at most 80% by weight, even more preferably at most 75% by weight, most preferably at most 70% by weight, and particularly at most 65% by weight, relative to the dry solids content of the scavenging fraction.

[0144] Preferably, the fructose content of the scavenging fraction is at most 5.0% by weight, more preferably at most 3.5% by weight, more preferably at most 2.0% by weight, even more preferably at most 1.0% by weight, even more preferably at most 0.5% by weight, most preferably at most 0.1% by weight, and particularly at most 0.01% by weight, relative to the dry solids content of the scavenging fraction.

[0145] Preferably, the glucose content of the removed fraction is at most 99% by weight, more preferably at most 95% by weight, more preferably at most 90% by weight, even more preferably at most 85% by weight, even more preferably at most 80% by weight, most preferably at most 75% by weight, and especially at most 70% by weight, relative to the dry solids content of the removed fraction.

[0146] Preferably, the sucrose content of the removed fraction is at most 95% by weight, more preferably at most 84% by weight, more preferably at most 73% by weight, even more preferably at most 62% by weight, even more preferably at most 51% by weight, most preferably at most 40% by weight, and particularly at most 30% by weight, relative to the dry solids content of the removed fraction.

[0147] Preferably, the dry solids content of the cleaning fraction (preferably the first cleaning fraction) is at least 4.0 wt%, preferably at least 6.0 wt%, more preferably at least 8.0 wt%, even more preferably at least 10 wt%, even more preferably at least 12 wt%, even more preferably at least 14 wt%, most preferably at least 16 wt%, and particularly at least 18 wt%, relative to the total weight of the cleaning fraction.

[0148] Preferably, the dry solids content of the removal fraction (preferably the second removal fraction) is at least 5.0% by weight, preferably at least 10% by weight, more preferably at least 15% by weight, even more preferably at least 20% by weight, even more preferably at least 25% by weight, even more preferably at least 30% by weight, most preferably at least 35% by weight, and particularly at least 40% by weight, relative to the total weight of the removal fraction.

[0149] Preferably, the hydroxymethylfurfural (HMF) content of the scavenging fraction is at least 1 ppmw, more preferably at least 5 ppmw, more preferably at least 10 ppmw, even more preferably at least 25 ppmw, even more preferably at least 50 ppmw, most preferably at least 100 ppmw, and particularly at least 250 ppmw, relative to the dry solids content of the scavenging fraction.

[0150] Preferably, the 2,3-butanedione content of the scavenging fraction is at least 1 ppmw, more preferably at least 5 ppmw, more preferably at least 10 ppmw, even more preferably at least 25 ppmw, even more preferably at least 50 ppmw, most preferably at least 100 ppmw, and particularly at least 250 ppmw, relative to the dry solids content of the scavenging fraction.

[0151] Preferably, the acetaldehyde content of the scavenging fraction is at least 1 ppmw, more preferably at least 5 ppmw, more preferably at least 10 ppmw, even more preferably at least 25 ppmw, even more preferably at least 50 ppmw, most preferably at least 100 ppmw, and particularly at least 250 ppmw, relative to the dry solids content of the scavenging fraction.

[0152] Preferably, the 2-keto-D-glucose content of the scavenging fraction is at least 1 ppmw, more preferably at least 5 ppmw, more preferably at least 10 ppmw, even more preferably at least 25 ppmw, even more preferably at least 50 ppmw, most preferably at least 100 ppmw, and particularly at least 250 ppmw, relative to the dry solids content of the scavenging fraction.

[0153] Preferably, the allolone content of the scavenging fraction is at least 1 ppmw, more preferably at least 5 ppmw, more preferably at least 10 ppmw, even more preferably at least 25 ppmw, and even more preferably at least 50 ppmw, most preferably at least 100 ppmw, and particularly at least 250 ppmw, relative to the dry solids content of the scavenging fraction.

[0154] Preferably, the 3-deoxyglucone content of the scavenging fraction is at least 1 ppmw, more preferably at least 5 ppmw, more preferably at least 10 ppmw, even more preferably at least 25 ppmw, even more preferably at least 50 ppmw, most preferably at least 100 ppmw, and particularly at least 250 ppmw, relative to the dry solids content of the scavenging fraction.

[0155] In an optional step (e) of the method according to the invention, the fructose-rich fraction obtained in step (d) is subjected to one or more concentration and / or purification measures to obtain a concentrated and / or purified fructose-rich fraction having a fructose content of at least 85% by weight relative to the dry solids content of the concentrated and / or purified fructose-rich fraction.

[0156] Preferably, the one or more concentration and / or purification measures include concentration; preferably reverse osmosis and / or evaporation.

[0157] Preferably, the one or more concentration and / or purification measures include demineralization and / or decolorization.

[0158] Those skilled in the art are aware of suitable methods for demineralization, including but not limited to ion exchange chromatography. Suitable ion exchange resins are commercially available.

[0159] Technicians are also aware of suitable methods for decolorization, including but not limited to adsorption. Suitable adsorbents such as activated carbon are commercially available.

[0160] In step (f) of the method according to the invention, the fructose-rich fraction obtained in step (d) or the concentrated and / or purified fructose-rich fraction obtained in optional step (e) is recycled to step (a) or (b).

[0161] In a preferred embodiment, the fructose-rich fraction or the concentrated and / or purified fructose-rich fraction is recycled to step (a).

[0162] In other preferred embodiments, the fructose-rich fraction or the concentrated and / or purified fructose-rich fraction is recycled to step (b).

[0163] In a preferred embodiment, the method according to the invention further includes the following steps: (g) Concentrate at least one of the one or more allulose-rich fractions to obtain a concentrated allulose-rich fraction; (h) Crystallize allulose from the concentrated allulose-rich fraction to obtain a suspension comprising allulose crystals and a liquid phase or substantially composed thereof; (i) separating the allulose crystals and the liquid phase from each other; preferably by centrifugation; and (j) Optionally, the allulose crystals are washed to obtain washed allulose crystals and washing water.

[0164] In a preferred embodiment, the method according to the invention further includes the following steps: (k) The liquid phase is recycled to the crude product or the pre-purified product for subsequent chromatographic separation in step (d).

[0165] Preferably, step (d) includes the following sub-steps: (d1) The crude product or the pre-purified product is separated by chromatography into (α) a first allulose-rich fraction and (β) an intermediate fraction rich in (i) fructose and (ii) one or more impurities and / or glucose and / or sucrose. (d2) The intermediate fraction was separated by chromatography into (α) a second allulose-rich fraction; (β) a fructose-rich fraction; and (γ) a scavenging fraction; and (d3) Optionally, the first allulose-rich fraction and the second allulose-rich fraction are combined with each other; And it also includes the following steps: (k') The liquid phase is recycled to an intermediate fraction for subsequent chromatographic separation in sub-step (d2).

[0166] In a preferred embodiment, the method according to the invention further includes the following steps: (l) The wash water is recycled to at least one of the one or more allulose-rich fractions for subsequent concentration in step (g).

[0167] Another aspect of the present invention relates to a method for preparing allulose products, comprising the following steps: (a) A starting composition comprising (α) fructose and (β) optional one or more impurities and / or glucose and / or sucrose; (b) Contact the starting composition with allulose-3-epimerase to convert fructose to allulose, thereby obtaining a crude product comprising (α) allulose, (β) fructose and (γ) one or more impurities and / or glucose and / or sucrose; (c) Optionally, the crude product is subjected to one or more pre-purification measures to obtain a pre-purified product, said pre-purified product comprising (α) allulose, (β) fructose and (γ) one or more impurities and / or glucose and / or sucrose; (d) Separating the crude product or the pre-purified product by chromatography. (α) One or more allulose-rich fractions, each fraction having an allulose content of at least 85% by weight relative to the dry solids content of the allulose-rich fractions; and (β) A fructose-rich fraction having a fructose content of at least 85% by weight relative to the dry solids content of the fructose-rich fraction; wherein the total impurity content of the fructose-rich fraction is at most 1.0% by weight, preferably at most 0.8% by weight, more preferably at most 0.6% by weight, even more preferably at most 0.4% by weight, even more preferably at most 0.2% by weight, most preferably at most 0.1% by weight, and particularly at most 0.01% by weight.

[0168] (e) Optionally, the fructose-rich fraction is subjected to one or more concentration and / or purification measures to obtain a concentrated and / or purified fructose-rich fraction having a fructose content of at least 85% by weight relative to the dry solids content of the concentrated and / or purified fructose-rich fraction. (f) Recycle the fructose-rich fraction or the concentrated and / or purified fructose-rich fraction to step (a) or (b); The one or more impurities mentioned therein are any organic compounds other than allulose, fructose, glucose and sucrose; Preferably, the one or more impurities include (i) allulose dimer, allulose-fructobiose, allulose-glucose-biose, allulose tetramer, bisallulose anhydride, levulinic acid, γ-hydroxyvalerate (GVA), furfural, hydroxymethylfurfural (HMF), 2,5-dimethylfuran, 2,5-furandicarboxylic acid (FDCA), 5-hydroxymethylfuran-2-carboxylic acid, 2,5-formylfurancarboxylic acid, 2,5-furandialdehyde, 2,5-bis-(hydroxy-methyl)furan, bis(5-formyl-2-furfural) ether, furan-2-carboxylic acid, furan-3-carboxylic acid, 5-hydroxyfurfural, 2,5-dihydro-2,5-dimethoxyfuran, (2R)-5-oxotetrahydro-2-furancarboxylic acid, bis(5-methylfurfural) ether, 5,5'-methylene-di(furan-2-carboxylic acid) or any combination thereof; and / or (ii) Lactic acid, maltol, furanol, allolone, glucone, 1-deoxyglucone, 3-deoxyglucone, 3-deoxygalactone, formic acid, acetic acid, propionic acid, glyoxal, or any combination thereof; and / or (iii) 2,3-Butanedione, acetaldehyde, 2-keto-D-glucose (glucose ketone), 3-deoxyglucose ketone or any combination thereof.

[0169] All preferred embodiments described above with respect to the method according to the first aspect of the invention are similarly applicable to the method according to the other aspect of the invention, and therefore will not be repeated below.

[0170] Figures 1 to 6 The invention is further illustrated, but should not be construed as limiting its scope.

[0171] Figure 1 A preferred embodiment of the invention is illustrated schematically, relating to a simulated moving bed chromatography method providing three fractions. Crystalline or syrupy fructose starting material from a fructose storage tank (1) and demineralized water (2) are preferably supplied to a mixing unit (3), and after mixing, preferably to a pH adjustment / demineralization unit (4). The starting composition thus prepared is preferably supplied to an enzyme reactor (5) equipped with an ultrafiltration device, wherein the starting composition is contacted with allulose-3-epimerase to convert fructose to allulose, thereby obtaining a crude product containing allulose and residual, i.e., unconverted fructose. The crude product further contains one or more impurities and / or one or more of glucose and / or sucrose, which may originate from various sources, particularly from recycling. After ultrafiltration, the crude reaction product is preferably pre-purified in a first demineralization / decolorization unit (6), and the resulting pre-purified product is preferably supplied to a simulated moving bed chromatography unit (7).

[0172] The simulated moving bed chromatography preferably provides three process streams: (i) a fructose-rich fraction preferably supplied to the first concentration unit (8); (ii) an allulose-rich fraction preferably supplied to the second concentration unit (11); and (iii) a scavenging fraction preferably treated as a scavenging solution (10).

[0173] The fructose-rich fraction is selectively concentrated, for example by reverse osmosis and / or evaporation, in a first concentration unit (8), and then preferably supplied to a second demineralization / decolorization unit (9), whereby the concentrated and / or purified fructose-rich fraction is preferably recycled to a mixing unit (3). Therefore, one or more impurities and / or glucose and / or sucrose that may be present and / or generated during enzymatic conversion and / or subsequent post-processing, and that may not be completely separated from the fructose-rich fraction by simulated moving bed chromatography, are also recycled to the mixing unit (3). This is a possible source of one or more impurities and / or glucose and / or sucrose in the crude product.

[0174] The post-processing of allulose-rich fractions depends on the nature of the desired allulose product.

[0175] When the allulose product is an allulose syrup, the allulose-rich fraction is preferably decolorized in a decolorization unit (12), followed by aseptic filtration in a sterile filtration unit (13). At this stage, the quality of the allulose product can be controlled at a first critical control point (14), and then the allulose syrup is preferably stored in a syrup storage tank (15).

[0176] When the allulose product is a solid, preferably at least partially crystalline material, the allulose-rich fraction is preferably further concentrated in a third concentration unit (16) for subsequent crystallization in a crystallization unit (17). The suspension exiting the crystallization unit (17) comprises allulose crystals and a liquid phase or substantially consists of both, and the allulose crystals and liquid phase are preferably separated from each other by centrifugation in a centrifugation unit (18). The resulting liquid phase is preferably recycled to the pre-purified product for subsequent chromatographic separation in a simulated moving bed chromatography unit (7). This is, among other things, another possible source of one or more impurities and / or glucose and / or sucrose in the crude product after recycling the fructose-rich fraction. The resulting allulose crystals are preferably washed with deionized water to obtain washed allulose crystals and wash water. The wash water is preferably recycled to the third concentration unit (16) or the second concentration unit (11). Among other things, this is also a further possible source of one or more impurities and / or glucose and / or sucrose in the crude product after recycling the fructose-rich fraction. The resulting washed allulose crystals are preferably dried in a drying unit (19). At this stage, the quality of the allulose product can be controlled at a second critical control point (20) before the allulose crystals are preferably stored in a crystallized product storage tank (21).

[0177] Figure 2 Another preferred embodiment of the invention is illustrated schematically, which relates to a first simulated moving bed chromatography providing two fractions and a subsequent second simulated moving bed chromatography providing three fractions.

[0178] and Figure 1 The implementation schemes shown are different, according to Figure 2 In the illustrated embodiment, the pre-purified product leaving the first demineralization / decolorization unit (6) is supplied to a first simulated moving bed chromatography unit (7), which preferably provides two process streams: (i) an intermediate fraction rich in fructose and (ii) one or more impurities and / or glucose and / or sucrose, which is preferably supplied to a second simulated moving bed chromatography unit (22); and (ii) a first allulose-rich fraction, which is preferably supplied to a second concentration unit (11). The second simulated moving bed chromatography unit (22) preferably provides three process streams: (i) a fructose-rich fraction preferably supplied to the first concentration unit (8); (ii) a second allulose-rich fraction preferably also supplied to the second concentration unit (11), which is preferably mixed with the first allulose-rich fraction supplied by the first simulated moving bed chromatography unit (7) in the second concentration unit; and (iii) a scavenging fraction preferably treated as a scavenging solution (10).

[0179] Alternatively, ( Figure 2 (Not shown in the text) The first simulated moving bed chromatography unit (7) can provide a third process flow, namely another scavenging fraction.

[0180] Further with Figure 1 The implementation schemes shown are different, according to Figure 2 The embodiment shown preferably recycles the liquid phase obtained by centrifugation in the centrifugation unit (18) to an intermediate fraction for subsequent chromatographic separation in the second simulated moving bed chromatography unit (22).

[0181] Figure 3 The working principle of the simulated moving bed (SMB) chromatography according to the present invention is illustrated schematically. This chromatography comprises, for example, four zones I to IV. Each zone is separated from the others by valves, which are individually adjustable to simulate the movement of a solid bed (stationary phase) against the flow of a fluid (liquid phase) in a countercurrent direction.

[0182] The chamber volume, especially the chamber volumes of regions II and III, is an important parameter that can be advantageously adjusted to optimize the efficiency of the chromatography.

[0183] A liquid feed containing allulose and fructose (i.e., crude or pre-purified product) is fed into the system between zones II and III. Water is introduced into zone I as a fresh liquid eluent. The ratio of water volume to feed volume, i.e., the water-to-feed ratio, is another important parameter that can be advantageously adjusted to optimize chromatographic efficiency. A lower water-to-feed ratio results in higher concentrations of solutions separated chromatographically (i.e., higher solids content) and lower energy consumption for subsequent water evaporation.

[0184] The residue (i.e., the fructose-rich fraction or intermediate fraction) is removed between zones III and IV, while the extract (i.e., the allulose-rich fraction) is removed between zones I and II. The ratio of the volume of extract (product) to the volume of residue, i.e., the extract to residue ratio, is another important parameter that can be advantageously adjusted to optimize the efficiency of the chromatography.

[0185] The chamber volume (especially in zones II and III), water to feed ratio (v / v), and extract to raffinate ratio (v / v) are interrelated and can be optimized to provide... - Allulose-rich fractions (extracts) with high allulose purity, high allulose recovery, and high solids content; and - A fructose-rich fraction (extraction residue) with low allulose content and high solids content.

[0186] Figure 4This is the elution curve of the sequential simulated moving bed (SSMB) chromatography in Example 1.

[0187] Figure 5 The diagram illustrates the effects of chamber volume (C1) in region I, chamber solvent (C4) in region IV, water to feed ratio (W / F), and extract (product) to raffinate ratio (P / R) on chromatographic separation. Large font indicates an increase in the corresponding parameter, small font indicates a decrease in the corresponding parameter, and arrows indicate the direction of change of the corresponding parameter in the graph.

[0188] Figure 6 This is a summary diagram of the evaluation in Example 2.

[0189] List of reference numerals in the attached diagram: 1: Fructose storage tank 2: Demineralized water 3: Hybrid Unit 4: pH Adjustment / Demineralization Unit 5: Enzyme reactor with ultrafiltration unit 6: First Demineralization / Decolorization Unit 7: The first simulated moving bed chromatography unit 8: First Concentration Unit 9: Second Demineralization / Decolorization Unit 10: Clear 11: Second Concentration Unit 12: Decolorization Unit 13: Sterile Filtration Unit 14: First critical control point 15: Syrup storage tank 16: Third Concentration Unit 17: Crystallization unit 18: Centrifuge Unit 19: Drying Unit 20: Second critical control point 21: Crystallized product storage tank 22: Second simulated moving bed chromatography unit The following embodiments further illustrate the present invention, but should not be construed as limiting its scope.

[0190] Example 1 - SSMB with two separation fractions: Fructose was converted to allulose by allulose-3-epimerase. The crude product was then pre-purified to obtain a pre-purified product with the following composition (determined by HPLC according to ICUMSA GS3-50): In a sequential simulated moving bed (SSMB) with two separation fractions, the pre-purified product was separated by chromatography into a residue fraction (fraction rich in fructose) and an extract fraction (fraction rich in allulose).

[0191] The results are as follows Figure 4 As shown.

[0192] As shown, in SSMB with two separation fractions, only partial separation occurs. The peaks of the major components, fructose and allulose, overlap, resulting in meaningful material stream fractions (raffinate and extract). Balanced mass flow means that the sum of all input mass flow rates equals the sum of all output mass flow rates. For SSMB, this means that unwanted components (sucrose, glucose, impurities) must also leave the SSMB via either the raffinate pathway (fructose-rich fraction) or the extract pathway (allulose-rich fraction). Undesirable components cannot be ideally separated, as can already be seen from the fructose and allulose fractions.

[0193] Example 2 - Evaluating the possibility of a third separation stage: To assess the feasibility of a third fraction, a test run was conducted. For this purpose, the raffinate fraction (the fructose-rich fraction) was divided into 10 evenly spaced measurement times. Ten samples of the raffinate fraction (the fructose-rich fraction) and one sample of the feed were analyzed (HPLC analysis according to ICUMSA GS3-50) to determine the absolute content of each component.

[0194] The assessment of absolute content is weighted based on the absolute mass flow rates of the feed stream and the residue stream.

[0195] Figure 6 A summary chart of this assessment is shown.

[0196] For glucose and sucrose, it can be seen that at the end of the entire raffinate fraction, the mass fraction % relative to the feed exceeds 100%. Sucrose reaches a value of 110.7%, while glucose reaches 103.8%. There are two reasons for this. First, the measured concentrations of sucrose and glucose are within the lower limit of quantitation, naturally exhibiting inaccuracies. Second, the mass balance of a continuously operating SSMB is almost never perfectly balanced. Slight flow rate fluctuations and inhomogeneities within the separation column will always cause fluctuations in the mass balance. A mass balance within 100% + / - 5% is generally considered balanced. This is the case for glucose; the case for sucrose is slightly higher. However, this does not change the trend and overall significance of the results.

[0197] As shown, unwanted components with shorter retention times than fructose tend to be present in the raffinate fraction (the fructose-rich fraction). Figure 6As shown, more than 100% of glucose and sucrose from the feed can be recovered at the end of the raffinate fraction (the fructose-rich fraction). The recovery rates of these unwanted components are consistently higher than those of fructose. Conversely, allulose recovery rates are consistently lower than those of fructose. This means the allulose peak is located downstream of the fructose peak. The superposition of fructose and allulose occurs when one of the components is at a higher concentration.

[0198] Therefore, the separation of components with retention times between allulose and fructose is always accompanied by high concentrations of allulose and fructose. Thus, reduction in this region is generally uneconomical.

[0199] However, the situation is different if the separated fraction contains a high proportion of sucrose and glucose (i.e., the components preceding fructose). These substances are consistently present in a higher mass ratio relative to the feed than fructose.

[0200] Fructose loss can be minimized by cutting off the third separation fraction at the beginning of the raffinate fraction (the fructose-rich fraction). When unwanted components accumulate in the system, cutting should be chosen so that the formation or addition of these unwanted components corresponds exactly to the amount of the third fraction. This prevents accumulation, but it also requires accepting the fact that a certain amount of fructose will be lost.

[0201] Example 3 - Two SSMBs, each with a third separation level: To prevent the accumulation of glucose and sucrose, a scheme was chosen that requires a second SSMB while performing classic clearance.

[0202] The mass balance of the main flow was determined to prevent the accumulation of sucrose and glucose, and the resulting losses of fructose and allulose. During continuous operation, a mass flow rate of 0.7 kg / h of sucrose and 1.7 kg / h of glucose must be discharged. The unavoidable fructose loss flow rate of 54.2 kg / h and allulose loss flow rate of 1.7 kg / h are ultimately achieved through a second SSMB and a scavenging flow. Example 4 - A single SSMB with a third separation level: When the same amounts of sucrose and glucose are to be discharged through a single SSMB with a third separation fraction, it can be mathematically proven that approximately 3.3% must be discharged as the third separation fraction at the beginning of the raffinate fraction (the fructose-rich fraction). In this case, 0.7 kg / h of sucrose and 1.7 kg / h of glucose will be discharged. However, the loss flow rate here is only 31.5 kg / h of fructose and 1.2 kg / h of allulose. A third separation fraction was established by using the first 3.3% of the residue fraction as the third separation fraction, effectively preventing the accumulation of unwanted components. Simultaneously, compared to the concept in Example 3, fructose loss was reduced by approximately 40%, and allulose loss was reduced by approximately 30%. Furthermore, the second SSMB can be eliminated, thus saving on investment and operating costs. The feasibility of using the third separation fraction in SSMB to separate unwanted components has been demonstrated. Furthermore, compared with the classic " Clear Compared to additional SSMB, implementing a third separation fraction is a more economical option in terms of raw material costs, investment, and operating costs. Furthermore, the third separation fraction can be operated economically for the separation of components with shorter retention times than fructose.

[0203] Allulose treatment also revealed unwanted components with retention times downstream of allulose. These unwanted components can also be separated by a third separation stage. In this case, the principle is exactly the same as that of the raffinate fraction (the fructose-rich fraction), but it only occurs at the end of the extract fraction (the allulose-rich fraction).

[0204] However, for fractions with retention times between fructose and allulose, a third separation fraction is not expected to be economically feasible. The losses would be substantial due to the high concentrations of fructose and allulose in this region.

Claims

1. A method for preparing allulose products, comprising the following steps: (a) Providing a starting composition comprising (α) fructose and (β) Optionally one or more impurities and / or glucose and / or sucrose; (b) Contacting the starting composition with allulose-3-epimerase to convert fructose to allulose, thereby obtaining a crude product comprising: (α) Allulose, (β) fructose and (γ) One or more impurities and / or glucose and / or sucrose; (c) Optionally, the crude product is subjected to one or more pre-purification measures to obtain a pre-purified product containing the following substances: (α) Allulose, (β) fructose and (γ) One or more impurities and / or glucose and / or sucrose; (d) Separating the crude product or the pre-purified product by chromatography. (α) One or more allulose-rich fractions, each fraction having an allulose content of at least 85% by weight relative to the dry solids content of the allulose-rich fractions; (β) A fructose-rich fraction having a fructose content of at least 85% by weight relative to the dry solids content of the fructose-rich fraction; and (γ) Optionally, a scavenging fraction rich in one or more impurities and / or glucose and / or sucrose; (e) Optionally, the fructose-rich fraction is subjected to one or more concentration and / or purification measures to obtain a concentrated and / or purified fructose-rich fraction having a fructose content of at least 85% by weight relative to the dry solids content of the concentrated and / or purified fructose-rich fraction. (f) Recycle the fructose-rich fraction or the concentrated and / or purified fructose-rich fraction to step (a) or (b); The one or more impurities mentioned therein are any organic compounds other than allulose, fructose, glucose and sucrose.

2. The method according to claim 1, wherein in step (d), the crude product or the pre-purified product is separated by chromatography into... (α) One or more allulose-rich fractions, each fraction having an allulose content of at least 85% by weight relative to the dry solids content of the allulose-rich fractions; (β) A fructose-rich fraction having a fructose content of at least 85% by weight relative to the dry solids content of the fructose-rich fraction; and (γ) A scavenging fraction rich in one or more impurities and / or glucose and / or sucrose.

3. The method according to claim 1 or 2, wherein the allulose product is solid, preferably at least partially crystalline.

4. The method according to claim 1 or 2, wherein the allulose product is a liquid, preferably a syrup.

5. The method according to any one of the preceding claims, wherein the fructose content of the starting composition is at least 40% by weight, preferably at least 60% by weight, more preferably at least 70% by weight, even more preferably at least 80% by weight, even more preferably at least 90% by weight, most preferably at least 95% by weight, and particularly at least 98% by weight, relative to the dry solids content of the starting composition.

6. The method according to any one of the preceding claims, wherein the starting composition comprises glucose.

7. The method according to claim 6, wherein the glucose content of the starting composition is at most 8.0% by weight, preferably at most 7.0% by weight, more preferably at most 6.0% by weight, even more preferably at most 5.0% by weight, even more preferably at most 4.0% by weight, most preferably at most 3.0% by weight, and particularly at most 2.0% by weight, relative to the dry solids content of the starting composition.

8. The method according to claim 6 or 7, wherein the glucose content of the starting composition is at least 0.0001 wt%, preferably at least 0.001 wt%, more preferably at least 0.01 wt%, even more preferably at least 0.1 wt%, even more preferably at least 0.2 wt%, most preferably at least 0.3 wt%, and particularly at least 0.4 wt%, relative to the dry solids content of the starting composition.

9. The method according to any one of the preceding claims, wherein the starting composition comprises sucrose.

10. The method according to claim 9, wherein the sucrose content of the starting composition is at most 1.8 wt%, preferably at most 1.6 wt%, more preferably at most 1.4 wt%, even more preferably at most 1.2 wt%, even more preferably at most 1.0 wt%, most preferably at most 0.8 wt%, and particularly at most 0.6 wt%, relative to the dry solids content of the starting composition.

11. The method according to any one of the preceding claims, wherein at least one of the one or more impurities is formed in step (b).

12. The method according to any one of the preceding claims, wherein at least one of the one or more impurities is formed in one or more steps following step (b).

13. The method according to any one of the preceding claims, wherein the one or more impurities comprise allulose dimer, allulose-fructobiose, allulose-glucose bisaccharide, allulose tetramer, bisallulose anhydride, levulinic acid, γ-hydroxyvalerate (GVA), furfural, hydroxymethylfurfural (HMF), 2,5-dimethylfuran, 2,5-furandicarboxylic acid (FDCA), 5-hydroxymethylfuran-2-carboxylic acid, 2,5-Formylfuran carboxylic acid, 2,5-furandialdehyde, 2,5-bis-(hydroxy-methyl)furan, bis(5-formyl-2-furfuryl) ether, furan-2-carboxylic acid, furan-3-carboxylic acid, 5-hydroxyfurfural, 2,5-dihydro-2,5-dimethoxyfuran, (2R)-5-oxotetrahydro-2-furan carboxylic acid, bis(5-methylfurfuryl) ether, 5,5'-methylene-bis(furan-2-carboxylic acid), or any combination thereof.

14. The method according to any one of the preceding claims, wherein the one or more impurities comprise lactic acid, maltol, furanol, allotropin, glucone (2-keto-D-glucose), 1-deoxyglucone, 3-deoxyglucone, 3-deoxygalactone, formic acid, acetic acid, propionic acid, glyoxal, or any combination thereof.

15. The method according to any one of the preceding claims, wherein the one or more impurities comprise 2,3-butanedione, acetaldehyde, 2-keto-D-glucose (glucone), 3-deoxyglucone, or any combination thereof.

16. The method according to any one of the preceding claims, wherein the total impurity content of the crude product is at least 0.0001 wt%, preferably at least 0.001 wt%, more preferably at least 0.01 wt%, even more preferably at least 0.1 wt%, even more preferably at least 0.2 wt%, most preferably at least 0.3 wt%, and particularly at least 0.5 wt%, relative to the dry solids content of the crude product.

17. The method according to any one of the preceding claims, wherein the total impurity content of the crude product is at most 7.0% by weight, preferably at most 6.0% by weight, more preferably at most 5.0% by weight, even more preferably at most 4.0% by weight, even more preferably at most 3.0% by weight, most preferably at most 2.0% by weight, and particularly at most 1.0% by weight, relative to the dry solids content of the crude product.

18. The method according to any one of the preceding claims, wherein the allulose content of the crude product is at least 15% by weight, preferably at least 23% by weight, more preferably at least 32% by weight, even more preferably at least 40% by weight, even more preferably at least 48% by weight, most preferably at least 57% by weight, and particularly at least 65% by weight, relative to the dry solids content of the crude product.

19. The method according to any one of the preceding claims, wherein the fructose content of the crude product is at most 85% by weight, preferably at most 77% by weight, more preferably at most 68% by weight, even more preferably at most 60% by weight, even more preferably at most 52% by weight, most preferably at most 44% by weight, and particularly at most 35% by weight, relative to the dry solids content of the crude product.

20. The method according to any one of the preceding claims, wherein the glucose content of the crude product is at most 8.0% by weight, preferably at most 7.0% by weight, more preferably at most 6.0% by weight, even more preferably at most 5.0% by weight, even more preferably at most 4.0% by weight, most preferably at most 3.0% by weight, and particularly at most 2.0% by weight, relative to the dry solids content of the crude product.

21. The method according to any one of the preceding claims, wherein the sucrose content of the crude product is at most 5.00% by weight, preferably at most 4.25% by weight, more preferably at most 3.50% by weight, even more preferably at most 2.75% by weight, even more preferably at most 2.00% by weight, most preferably at most 1.25% by weight, and particularly at most 0.50% by weight, relative to the dry solids content of the crude product.

22. The method according to any one of the preceding claims, wherein the hydroxymethylfurfural (HMF) content of the crude product is in the range of 1 to 10,000 ppmw, preferably 1 to 8,000 ppmw, more preferably 1 to 6,000 ppmw, even more preferably 1 to 4,000 ppmw, even more preferably 1 to 2,000 ppmw, most preferably 1 to 1,000 ppmw, and particularly in the range of 1 to 500 ppmw, relative to the dry solids content of the crude product.

23. The method according to any one of the preceding claims, wherein the 2,3-butanedione content of the crude product is in the range of 1 to 10,000 ppmw, preferably 1 to 8,000 ppmw, more preferably 1 to 6,000 ppmw, even more preferably 1 to 4,000 ppmw, even more preferably 1 to 2,000 ppmw, most preferably 1 to 1,000 ppmw, and particularly in the range of 1 to 500 ppmw, relative to the dry solids content of the crude product.

24. The method according to any one of the preceding claims, wherein the acetaldehyde content of the crude product is in the range of 1 to 10,000 ppmw, preferably 1 to 8,000 ppmw, more preferably 1 to 6,000 ppmw, even more preferably 1 to 4,000 ppmw, even more preferably 1 to 2,000 ppmw, most preferably 1 to 1,000 ppmw, and particularly in the range of 1 to 500 ppmw, relative to the dry solids content of the crude product.

25. The method according to any one of the preceding claims, wherein the 2-keto-D-glucose content of the crude product is in the range of 1 to 10,000 ppmw, preferably 1 to 8,000 ppmw, more preferably 1 to 6,000 ppmw, even more preferably 1 to 4,000 ppmw, even more preferably 1 to 2,000 ppmw, most preferably 1 to 1,000 ppmw, and particularly in the range of 1 to 500 ppmw, relative to the dry solids content of the crude product.

26. The method according to any one of the preceding claims, wherein the allolone content of the crude product is in the range of 1 to 10,000 ppmw, preferably 1 to 8,000 ppmw, more preferably 1 to 6,000 ppmw, even more preferably 1 to 4,000 ppmw, even more preferably 1 to 2,000 ppmw, most preferably 1 to 1,000 ppmw, and particularly 1 to 500 ppmw, relative to the dry solids content of the crude product.

27. The method according to any one of the preceding claims, wherein the 3-deoxyglucone content of the crude product is in the range of 1 to 10,000 ppmw, preferably 1 to 8,000 ppmw, more preferably 1 to 6,000 ppmw, even more preferably 1 to 4,000 ppmw, even more preferably 1 to 2,000 ppmw, most preferably 1 to 1,000 ppmw, and particularly in the range of 1 to 500 ppmw, relative to the dry solids content of the crude product.

28. The method according to any one of the preceding claims, wherein the one or more pre-purification measures include filtration, preferably ultrafiltration.

29. The method according to any one of the preceding claims, wherein the one or more pre-purification measures include demineralization and / or decolorization.

30. The method according to any one of the preceding claims, wherein the chromatographic separation in step (d) provides - One or more allulose-rich fractions, wherein, relative to the dry solids content of the one or more allulose-rich fractions, the allulose content is in the range of 90 to 100% by weight, the fructose content is in the range of 0 to 5% by weight (50,000 ppmw), and the glucose content is in the range of 0 to 0.5% by weight (5,000 ppmw). - A fructose-rich fraction, wherein, relative to the dry solids content of the fructose-rich fraction, the fructose content is in the range of 90 to 100% by weight, the allulose content is in the range of 0 to 5% by weight (50,000 ppmw), and the glucose content is in the range of 0 to 1.5% by weight (15,000 ppmw).

31. The method according to any one of the preceding claims, wherein the chromatographic separation comprises at least one simulated moving bed chromatography (SMB), preferably at least one sequential simulated moving bed chromatography (SSMB).

32. The method according to claim 31, wherein the water-to-feed ratio (v / v) of the SMB is at most 4.0, more preferably at most 3.7, even more preferably at most 3.4, even more preferably at most 3.1, even more preferably at most 2.8, most preferably at most 2.5, and particularly at most 2.

2.

33. The method according to claim 31 or 32, wherein the water-to-feed ratio (v / v) of the SMB is at least 0.8, more preferably at least 0.9, even more preferably at least 1.0, even more preferably at least 1.1, even more preferably at least 1.2, most preferably at least 1.3, and particularly at least 1.

4.

34. The method according to any one of claims 31 to 33, wherein the extract to raffinate ratio (v / v) of the SMB is at most 1.6, more preferably at most 1.5, even more preferably at most 1.4, even more preferably at most 1.3, even more preferably at most 1.2, most preferably at most 1.1, and particularly at most 1.

0.

35. The method according to any one of claims 31 to 34, wherein the extract to raffinate ratio (v / v) of the SMB is at least 0.25, more preferably at least 0.30, even more preferably at least 0.35, even more preferably at least 0.40, even more preferably at least 0.45, most preferably at least 0.50, and particularly at least 0.

55.

36. The method according to any one of claims 31 to 35, wherein the purity of allulose in the extract, i.e., the allulose-rich fraction, is at least 93%, more preferably at least 94%, even more preferably at least 95%, even more preferably at least 96%, even more preferably at least 97%, most preferably at least 98%, and particularly at least 99%.

37. The method according to any one of claims 31 to 36, wherein the recovery rate of allulose is at least 79%, more preferably at least 80%, even more preferably at least 81%, still more preferably at least 82%, even more preferably at least 83%, most preferably at least 84%, and particularly at least 85%; preferably wherein the recovery rate of allulose is at least 86%, more preferably at least 87%, even more preferably at least 88%, still more preferably at least 89%, even more preferably at least 90%, most preferably at least 91%, and particularly at least 92%.

38. The method according to any one of claims 31 to 37, wherein the recovery rate of allulose is at least 93%, more preferably at least 94%, even more preferably at least 95%, even more preferably at least 96%, even more preferably at least 97%, most preferably at least 98%, and particularly at least 99%.

39. The method according to any one of the preceding claims, comprising single simulated moving bed (SMB) chromatography, preferably single sequential simulated moving bed (SSMB) chromatography.

40. The method according to any one of the preceding claims, wherein in step (d), the crude product obtained in step (b) or optionally the pre-purified product obtained in step (c) is then separated by chromatography into... (α) An allulose-rich fraction having an allulose content of at least 85% by weight relative to the dry solids content of the allulose-rich fraction; (β) A fructose-rich fraction having a fructose content of at least 85% by weight relative to the dry solids content of the fructose-rich fraction; and (γ) A scavenging fraction rich in one or more impurities and / or glucose and / or sucrose.

41. The method of claim 40, wherein the allulose-rich fraction is separated downstream of the fructose-rich fraction in the flow direction of the crude product obtained in step (b) or optionally the pre-purified product obtained in step (c).

42. The method according to claim 40 or 41, wherein the scavenging fraction is separated upstream of the fructose-rich fraction by chromatography, and the allulose-rich fraction is separated downstream of the fructose-rich fraction.

43. The method according to any one of claims 40 to 42, wherein the fructose-rich fraction is separated upstream of the allulose-rich fraction by chromatography, and the scavenging fraction is separated downstream of the allulose-rich fraction.

44. The method according to any one of claims 40 to 43, wherein the first scavenging fraction is separated upstream of the fructose-rich fraction by chromatography, the allulose-rich fraction is separated downstream of the fructose-rich fraction, and the second scavenging fraction is separated downstream of the allulose-rich fraction.

45. The method according to any one of claims 40 to 44, wherein the scavenging fraction is separated upstream of the fructose-rich fraction, and the flow rate of the scavenging fraction reaches at most 9.0% by weight of the flow rate of the fructose-rich fraction, preferably at most 8.0% by weight, more preferably at most 7.0% by weight, even more preferably at most 6.0% by weight, even more preferably at most 5.0% by weight, most preferably at most 4.0% by weight, and particularly at most 3.0% by weight.

46. ​​The method according to any one of claims 40 to 45, wherein a scavenging fraction is separated downstream of the allulose-rich fraction, and the flow rate of the scavenging fraction reaches at most 9.0% by weight, preferably at most 8.0% by weight, even more preferably at most 7.0% by weight, even more preferably at most 6.0% by weight, even more preferably at most 5.0% by weight, most preferably at most 4.0% by weight, and particularly at most 3.0% by weight.

47. The method according to any one of claims 1 to 38, comprising two simulated moving bed (SMB) chromatograms, preferably two sequential simulated moving bed (SSMB) chromatograms.

48. The method according to any one of the preceding claims, wherein step (d) comprises the following sub-steps: (d1) Separate the crude product or the pre-purified product by chromatography. (α) First allulose-rich fraction and (β) An intermediate fraction rich in (i) fructose and (ii) one or more impurities and / or glucose and / or sucrose; (d2) The intermediate fraction is separated into... by chromatography. (α) Second fraction rich in allulose; (β) the fructose-rich fraction; and (γ) the clearing stage; and (d3) Optionally, the first allulose-rich fraction and the second allulose-rich fraction are combined with each other.

49. The method of claim 48, wherein, in the flow direction of the crude product obtained in step (b) or optionally the pre-purified product obtained in step (c), the first allulose-rich fraction is separated downstream of the intermediate fraction in sub-step (d1).

50. The method according to claim 48 or 49, wherein the scavenging fraction is separated upstream of the intermediate fraction by chromatography, and the first allulose-rich fraction is separated downstream of the intermediate fraction.

51. The method according to any one of claims 48 to 50, wherein the intermediate fraction is separated by chromatography upstream of the first allulose-rich fraction, and the scavenging fraction is separated downstream of the first allulose-rich fraction.

52. The method according to any one of claims 48 to 51, wherein the first scavenging fraction is separated upstream of the intermediate fraction by chromatography, the first allulose-rich fraction is separated downstream of the intermediate fraction, and the second scavenging fraction is separated downstream of the first allulose-rich fraction.

53. The method according to any one of claims 48 to 52, wherein the clearing stage is separated upstream of the intermediate stage, and the flow rate of the clearing stage reaches at most 9.0% by weight of the flow rate of the intermediate stage, preferably at most 8.0% by weight, even more preferably at most 7.0% by weight, even more preferably at most 6.0% by weight, even more preferably at most 5.0% by weight, most preferably at most 4.0% by weight, and particularly at most 3.0% by weight.

54. The method according to any one of claims 48 to 53, wherein a scavenging fraction is separated downstream of the first allulose-rich fraction, and the flow rate of the scavenging fraction reaches at most 9.0 wt% of the flow rate of the first allulose-rich fraction, preferably at most 8.0 wt%, more preferably at most 7.0 wt%, even more preferably at most 6.0 wt%, even more preferably at most 5.0 wt%, most preferably at most 4.0 wt%, and particularly at most 3.0 wt%.

55. The method according to any one of claims 48 to 54, wherein in the flow direction of the crude product obtained in step (b) or optionally the pre-purified product obtained in step (c), the second allulose-rich fraction is separated downstream of the fructose-rich fraction in sub-step (d2).

56. The method according to any one of claims 48 to 55, wherein the scavenging fraction is separated upstream of the fructose-rich fraction by chromatography, and the second allulose-rich fraction is separated downstream of the fructose-rich fraction.

57. The method according to any one of claims 48 to 56, wherein the fructose-rich fraction is separated upstream of the second allulose-rich fraction by chromatography, and the scavenging fraction is separated downstream of the second allulose-rich fraction.

58. The method according to any one of claims 48 to 57, wherein the first scavenging fraction is separated upstream of the fructose-rich fraction by chromatography, the second allulose-rich fraction is separated downstream of the fructose-rich fraction, and the second scavenging fraction is separated downstream of the second allulose-rich fraction.

59. The method according to any one of claims 48 to 58, wherein the scavenging fraction is separated upstream of the fructose-rich fraction, and the flow rate of the scavenging fraction reaches at most 9.0% by weight of the flow rate of the fructose-rich fraction, preferably at most 8.0% by weight, more preferably at most 7.0% by weight, even more preferably at most 6.0% by weight, even more preferably at most 5.0% by weight, most preferably at most 4.0% by weight, and particularly at most 3.0% by weight.

60. The method according to any one of claims 48 to 59, wherein a scavenging fraction is separated downstream of the second allulose-rich fraction, and the flow rate of the scavenging fraction reaches at most 9.0% by weight, preferably at most 8.0% by weight, even more preferably at most 7.0% by weight, even more preferably at most 6.0% by weight, even more preferably at most 5.0% by weight, most preferably at most 4.0% by weight, and particularly at most 3.0% by weight.

61. The method according to any one of the preceding claims, wherein the one or more allulose-rich fractions independently have an allulose content of at least 87.5% by weight, preferably at least 90.0% by weight, more preferably at least 92.5% by weight, even more preferably at least 95.0% by weight, even more preferably at least 97.5% by weight, most preferably at least 98.5% by weight, and particularly at least 99.0% by weight, relative to the dry solids content of the one or more allulose-rich fractions.

62. The method according to any one of the preceding claims, wherein, relative to the dry solids content of the one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a fructose content of up to 12.5% ​​by weight, preferably up to 7.5% by weight, more preferably up to 5.0% by weight, even more preferably up to 2.5% by weight, even more preferably up to 1.0% by weight, most preferably up to 0.1% by weight, and particularly up to 0.01% by weight.

63. The method according to any one of the preceding claims, wherein, relative to the dry solids content of the one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a total impurity content of up to 2.0% by weight, preferably up to 1.8% by weight, more preferably up to 1.6% by weight, even more preferably up to 1.4% by weight, and still more preferably up to 1.2% by weight.

64. The method according to any one of the preceding claims, wherein, relative to the dry solids content of the one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a total impurity content of at most 1.0% by weight, preferably at most 0.8% by weight, more preferably at most 0.6% by weight, even more preferably at most 0.4% by weight, even more preferably at most 0.2% by weight, most preferably at most 0.1% by weight, and particularly at most 0.01% by weight.

65. The method according to any one of the preceding claims, wherein, relative to the dry solids content of the one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a glucose content of at most 3.0% by weight, preferably at most 2.0% by weight, more preferably at most 1.5% by weight, even more preferably at most 1.0% by weight, even more preferably at most 0.5% by weight, most preferably at most 0.1% by weight, and particularly at most 0.01% by weight.

66. The method according to any one of the preceding claims, wherein, relative to the dry solids content of the one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a sucrose content of up to 3.0% by weight, preferably up to 2.0% by weight, more preferably up to 1.5% by weight, even more preferably up to 1.0% by weight, even more preferably up to 0.5% by weight, most preferably up to 0.1% by weight, and particularly up to 0.01% by weight.

67. The method according to any one of the preceding claims, wherein, relative to the total weight of the one or more allulose-rich fractions, the one or more allulose-rich fractions independently have a dry solids content of at least 4.0% by weight, preferably at least 6.0% by weight, more preferably at least 8.0% by weight, even more preferably at least 10% by weight, even more preferably at least 12% by weight, even more preferably at least 14% by weight, most preferably at least 16% by weight, and particularly at least 18% by weight.

68. The method according to any one of the preceding claims, wherein the one or more allulose-rich fractions independently have a dry solids content of up to 10,000 ppmw, preferably up to 8,000 ppmw, more preferably up to 6,000 ppmw, even more preferably up to 4,000 ppmw, even more preferably up to 2,000 ppmw, most preferably up to 1,000 ppmw, and particularly up to 500 ppmw.

69. The method according to any one of the preceding claims, wherein the one or more allulose-rich fractions independently have a 2,3-butanedione content of up to 10,000 ppmw, preferably up to 8,000 ppmw, more preferably up to 6,000 ppmw, even more preferably up to 4,000 ppmw, even more preferably up to 2,000 ppmw, most preferably up to 1,000 ppmw, and particularly up to 500 ppmw, relative to the dry solids content of the one or more allulose-rich fractions.

70. The method according to any one of the preceding claims, wherein the one or more allulose-rich fractions independently have an acetaldehyde content of up to 10,000 ppmw, preferably up to 8,000 ppmw, more preferably up to 6,000 ppmw, even more preferably up to 4,000 ppmw, even more preferably up to 2,000 ppmw, most preferably up to 1,000 ppmw, and particularly up to 500 ppmw, relative to the dry solids content of the one or more allulose-rich fractions.

71. The method according to any one of the preceding claims, wherein the one or more allulose-rich fractions independently have a 2-keto-D-glucose content of up to 10,000 ppmw, preferably up to 8,000 ppmw, more preferably up to 6,000 ppmw, even more preferably up to 4,000 ppmw, even more preferably up to 2,000 ppmw, most preferably up to 1,000 ppmw, and particularly up to 500 ppmw, relative to the dry solids content of the one or more allulose-rich fractions.

72. The method according to any one of the preceding claims, wherein the one or more allulose-rich fractions independently have an allulone content of up to 10,000 ppmw, preferably up to 8,000 ppmw, more preferably up to 6,000 ppmw, even more preferably up to 4,000 ppmw, even more preferably up to 2,000 ppmw, most preferably up to 1,000 ppmw, and particularly up to 500 ppmw, relative to the dry solids content of the one or more allulose-rich fractions.

73. The method according to any one of the preceding claims, wherein the one or more allulose-rich fractions independently have a 3-deoxyglucone content of up to 10,000 ppmw, preferably up to 8,000 ppmw, more preferably up to 6,000 ppmw, even more preferably up to 4,000 ppmw, even more preferably up to 2,000 ppmw, most preferably up to 1,000 ppmw, and particularly up to 500 ppmw, relative to the dry solids content of the one or more allulose-rich fractions.

74. The method according to any one of the preceding claims, wherein the fructose content of the fructose-rich fraction is at least 70.0% by weight, preferably at least 72.5% by weight, more preferably at least 75.0% by weight, even more preferably at least 77.5% by weight, even more preferably at least 80.0% by weight, most preferably at least 82.5% by weight, and particularly at least 85.0% by weight, relative to the dry solids content of the fructose-rich fraction.

75. The method according to any one of the preceding claims, wherein the fructose content of the fructose-rich fraction is at least 87.5% by weight, preferably at least 90.0% by weight, more preferably at least 92.5% by weight, even more preferably at least 95.0% by weight, even more preferably at least 97.5% by weight, most preferably at least 98.5% by weight, and particularly at least 99.0% by weight, relative to the dry solids content of the fructose-rich fraction.

76. The method according to any one of the preceding claims, wherein the allulose content of the fructose-rich fraction is at most 12.5% ​​by weight, preferably at most 7.5% by weight, more preferably at most 5.0% by weight, even more preferably at most 2.5% by weight, even more preferably at most 1.0% by weight, most preferably at most 0.1% by weight, and particularly at most 0.01% by weight, relative to the dry solids content of the fructose-rich fraction.

77. The method according to any one of the preceding claims, wherein the total impurity content of the fructose-rich fraction is at most 4.5% by weight, preferably at most 4.0% by weight, more preferably at most 3.5% by weight, even more preferably at most 3.0% by weight, even more preferably at most 2.5% by weight, most preferably at most 2.0% by weight, and particularly at most 1.5% by weight, relative to the dry solids content of the fructose-rich fraction.

78. The method according to any one of the preceding claims, wherein the total impurity content of the fructose-rich fraction is at most 1.0% by weight, preferably at most 0.8% by weight, more preferably at most 0.6% by weight, even more preferably at most 0.4% by weight, even more preferably at most 0.2% by weight, most preferably at most 0.1% by weight, and particularly at most 0.01% by weight, relative to the dry solids content of the fructose-rich fraction.

79. The method according to any one of the preceding claims, wherein the glucose content of the fructose-rich fraction is at most 3.0% by weight, preferably at most 2.0% by weight, more preferably at most 1.5% by weight, even more preferably at most 1.0% by weight, even more preferably at most 0.5% by weight, most preferably at most 0.1% by weight, and particularly at most 0.01% by weight, relative to the dry solids content of the fructose-rich fraction.

80. The method according to any one of the preceding claims, wherein the sucrose content of the fructose-rich fraction is at most 3.0% by weight, preferably at most 2.0% by weight, more preferably at most 1.5% by weight, even more preferably at most 1.0% by weight, even more preferably at most 0.5% by weight, most preferably at most 0.1% by weight, and particularly at most 0.01% by weight, relative to the dry solids content of the fructose-rich fraction.

81. The method according to any one of the preceding claims, wherein, relative to the total weight of the fructose-rich fraction, the dry solids content of the second scavenging fraction is preferably at least 5.0 wt%, preferably at least 10 wt%, more preferably at least 15 wt%, even more preferably at least 20 wt%, even more preferably at least 25 wt%, even more preferably at least 30 wt%, most preferably at least 35 wt%, and particularly at least 40 wt%.

82. The method according to any one of the preceding claims, wherein the hydroxymethylfurfural (HMF) content of the fructose-rich fraction is at most 10,000 ppmw, preferably at most 8,000 ppmw, more preferably at most 6,000 ppmw, even more preferably at most 4,000 ppmw, even more preferably at most 2,000 ppmw, most preferably at most 1,000 ppmw, and particularly at most 500 ppmw, relative to the dry solids content of the fructose-rich fraction.

83. The method according to any one of the preceding claims, wherein the 2,3-butanedione content of the fructose-rich fraction is at most 10,000 ppmw, preferably at most 8,000 ppmw, more preferably at most 6,000 ppmw, even more preferably at most 4,000 ppmw, even more preferably at most 2,000 ppmw, most preferably at most 1,000 ppmw, and particularly at most 500 ppmw, relative to the dry solids content of the fructose-rich fraction.

84. The method according to any one of the preceding claims, wherein the acetaldehyde content of the fructose-rich fraction is at most 10,000 ppmw, preferably at most 8,000 ppmw, more preferably at most 6,000 ppmw, even more preferably at most 4,000 ppmw, even more preferably at most 2,000 ppmw, most preferably at most 1,000 ppmw, and particularly at most 500 ppmw, relative to the dry solids content of the fructose-rich fraction.

85. The method according to any one of the preceding claims, wherein the 2-keto-D-glucose content of the fructose-rich fraction is at most 10,000 ppmw, preferably at most 8,000 ppmw, more preferably at most 6,000 ppmw, even more preferably at most 4,000 ppmw, even more preferably at most 2,000 ppmw, most preferably at most 1,000 ppmw, and particularly at most 500 ppmw, relative to the dry solids content of the fructose-rich fraction.

86. The method according to any one of the preceding claims, wherein the allolone content of the fructose-rich fraction is at most 10,000 ppmw, preferably at most 8,000 ppmw, more preferably at most 6,000 ppmw, even more preferably at most 4,000 ppmw, even more preferably at most 2,000 ppmw, most preferably at most 1,000 ppmw, and particularly at most 500 ppmw, relative to the dry solids content of the fructose-rich fraction.

87. The method according to any one of the preceding claims, wherein the 3-deoxyglucone content of the fructose-rich fraction is at most 10,000 ppmw, preferably at most 8,000 ppmw, more preferably at most 6,000 ppmw, even more preferably at most 4,000 ppmw, even more preferably at most 2,000 ppmw, most preferably at most 1,000 ppmw, and particularly at most 500 ppmw, relative to the dry solids content of the fructose-rich fraction.

88. The method according to any one of the preceding claims, wherein the total impurity content of the scavenging fraction is higher than the total impurity content of the one or more allulose-rich fractions.

89. The method according to any one of the preceding claims, wherein the total impurity content of the scavenged fraction is higher than the total impurity content of the fructose-rich fraction.

90. The method according to any one of the preceding claims, wherein the total impurity content of the removal fraction is at least 0.001 wt%, preferably at least 0.01 wt%, more preferably at least 0.1 wt%, even more preferably at least 0.5 wt%, even more preferably at least 1.0 wt%, most preferably at least 1.5 wt%, and particularly at least 2.0 wt%, relative to the dry solids content of the removal fraction.

91. The method according to any one of the preceding claims, wherein the allulose content of the scavenging fraction is at most 5.0% by weight, preferably at most 3.5% by weight, more preferably at most 2.0% by weight, even more preferably at most 1.0% by weight, even more preferably at most 0.5% by weight, most preferably at most 0.1% by weight, and particularly at most 0.01% by weight, relative to the dry solids content of the scavenging fraction.

92. The method according to any one of the preceding claims, wherein the fructose content of the scavenging fraction is at most 95% by weight, preferably at most 90% by weight, more preferably at most 85% by weight, even more preferably at most 80% by weight, even more preferably at most 75% by weight, most preferably at most 70% by weight, and particularly at most 65% by weight, relative to the dry solids content of the scavenging fraction.

93. The method according to any one of the preceding claims, wherein the fructose content of the scavenging fraction is at most 5.0 wt%, preferably at most 3.5 wt%, more preferably at most 2.0 wt%, even more preferably at most 1.0 wt%, even more preferably at most 0.5 wt%, most preferably at most 0.1 wt%, and particularly at most 0.01 wt%, relative to the dry solids content of the scavenging fraction.

94. The method according to any one of the preceding claims, wherein the glucose content of the scavenging fraction is at most 99% by weight, preferably at most 95% by weight, more preferably at most 90% by weight, even more preferably at most 85% by weight, even more preferably at most 80% by weight, most preferably at most 75% by weight, and particularly at most 70% by weight, relative to the dry solids content of the scavenging fraction.

95. The method according to any one of the preceding claims, wherein the sucrose content of the scavenging fraction is at most 95% by weight, preferably at most 84% by weight, more preferably at most 73% by weight, even more preferably at most 62% by weight, even more preferably at most 51% by weight, most preferably at most 40% by weight, and particularly at most 30% by weight, relative to the dry solids content of the scavenging fraction.

96. The method according to any one of the preceding claims, wherein the dry solids content of the first cleaning fraction is preferably at least 4.0 wt%, preferably at least 6.0 wt%, more preferably at least 8.0 wt%, even more preferably at least 10 wt%, even more preferably at least 12 wt%, even more preferably at least 14 wt%, most preferably at least 16 wt%, and particularly at least 18 wt%, relative to the total weight of the cleaning fraction.

97. The method according to any one of the preceding claims, wherein the dry solids content of the second removal fraction is preferably at least 5.0 wt%, more preferably at least 10 wt%, more preferably at least 15 wt%, even more preferably at least 20 wt%, even more preferably at least 25 wt%, even more preferably at least 30 wt%, most preferably at least 35 wt%, and particularly at least 40 wt%, relative to the total weight of the removal fraction.

98. The method according to any one of the preceding claims, wherein the hydroxymethylfurfural content of the scavenging fraction is at least 1 ppmw, preferably at least 5 ppmw, more preferably at least 10 ppmw, even more preferably at least 25 ppmw, even more preferably at least 50 ppmw, most preferably at least 100 ppmw, and particularly at least 250 ppmw, relative to the dry solids content of the scavenging fraction.

99. The method according to any one of the preceding claims, wherein the 2,3-butanedione content of the scavenging fraction is at least 1 ppmw, preferably at least 5 ppmw, more preferably at least 10 ppmw, even more preferably at least 25 ppmw, even more preferably at least 50 ppmw, most preferably at least 100 ppmw, and particularly at least 250 ppmw, relative to the dry solids content of the scavenging fraction.

100. The method according to any one of the preceding claims, wherein the acetaldehyde content of the scavenging fraction is at least 1 ppmw, preferably at least 5 ppmw, more preferably at least 10 ppmw, even more preferably at least 25 ppmw, even more preferably at least 50 ppmw, most preferably at least 100 ppmw, and particularly at least 250 ppmw, relative to the dry solids content of the scavenging fraction.

101. The method according to any one of the preceding claims, wherein the 2-keto-D-glucose content of the scavenging fraction is at least 1 ppmw, preferably at least 5 ppmw, more preferably at least 10 ppmw, even more preferably at least 25 ppmw, even more preferably at least 50 ppmw, most preferably at least 100 ppmw, and particularly at least 250 ppmw, relative to the dry solids content of the scavenging fraction.

102. The method according to any one of the preceding claims, wherein the allolone content of the scavenging fraction is at least 1 ppmw, preferably at least 5 ppmw, more preferably at least 10 ppmw, even more preferably at least 25 ppmw, even more preferably at least 50 ppmw, most preferably at least 100 ppmw, and particularly at least 250 ppmw, relative to the dry solids content of the scavenging fraction.

103. The method according to any one of the preceding claims, wherein the 3-deoxyglucone content of the scavenging fraction is at least 1 ppmw, preferably at least 5 ppmw, more preferably at least 10 ppmw, even more preferably at least 25 ppmw, even more preferably at least 50 ppmw, most preferably at least 100 ppmw, and particularly at least 250 ppmw, relative to the dry solids content of the scavenging fraction.

104. The method according to any one of the preceding claims, wherein the one or more concentration and / or purification measures include concentration; preferably reverse osmosis and / or evaporation.

105. The method according to any one of the preceding claims, wherein the one or more concentration and / or purification measures include demineralization and / or decolorization.

106. The method according to any one of the preceding claims, wherein the fructose-rich fraction or the concentrated and / or purified fructose-rich fraction is recycled to step (a).

107. The method according to any one of the preceding claims, wherein the fructose-rich fraction or the concentrated and / or purified fructose-rich fraction is recycled to step (b).

108. The method according to any one of the preceding claims, further comprising the following steps: (g) Concentrate at least one of the one or more allulose-rich fractions to obtain a concentrated allulose-rich fraction; (h) Crystallize allulose from the concentrated allulose-rich fraction to obtain a suspension comprising allulose crystals and a liquid phase or substantially composed thereof; (i) Separating the allulose crystals and the liquid phase from each other; preferably by centrifugation; as well as (j) Optionally, the allulose crystals are washed to obtain washed allulose crystals and washing water.

109. The method of claim 108, further comprising the following steps: (k) The liquid phase is recycled to the crude product or the pre-purified product for subsequent chromatographic separation in step (d).

110. The method according to any one of the preceding claims, wherein step (d) comprises the following sub-steps: (d1) Separate the crude product or the pre-purified product by chromatography. (α) First allulose-rich fraction and (β) An intermediate fraction rich in (i) fructose and (ii) one or more impurities and / or glucose and / or sucrose; (d2) The intermediate fraction is separated into... by chromatography. (α) Second fraction rich in allulose; (β) the fructose-rich fraction; and (γ) the clearing stage; and (d3) Optionally, the first allulose-rich fraction and the second allulose-rich fraction are combined with each other; and It also includes the following steps: (k') The liquid phase is recycled to the intermediate fraction for subsequent chromatographic separation in sub-step (d2).

111. The method according to any one of claims 108 to 110, further comprising the following steps: (l) The wash water is recycled to at least one of the one or more allulose-rich fractions for subsequent concentration in step (g).

112. The method according to any one of the preceding claims, comprising the following steps: (a) Providing a starting composition comprising (α) fructose and (β) Optional one or more impurities and / or glucose and / or sucrose; (b) Contacting the starting composition with allulose-3-epimerase to convert fructose to allulose, thereby obtaining a crude product comprising: (α) Allulose, (β) fructose and (γ) One or more impurities and / or glucose and / or sucrose; (c) Optionally, the crude product is subjected to one or more pre-purification measures to obtain a pre-purified product containing the following substances: (α) Allulose, (β) fructose and (γ) One or more impurities and / or glucose and / or sucrose; (d) Separating the crude product or the pre-purified product by chromatography. (α) One or more allulose-rich fractions, each fraction having an allulose content of at least 85% by weight relative to the dry solids content of the allulose-rich fractions; and (β) A fructose-rich fraction having a fructose content of at least 85% by weight relative to the dry solids content of the fructose-rich fraction; wherein the total impurity content of the fructose-rich fraction is at most 1.0% by weight, preferably at most 0.8% by weight, more preferably at most 0.6% by weight, even more preferably at most 0.4% by weight, even more preferably at most 0.2% by weight, most preferably at most 0.1% by weight, and particularly at most 0.01% by weight; (e) Optionally, the fructose-rich fraction is subjected to one or more concentration and / or purification measures to obtain a concentrated and / or purified fructose-rich fraction having a fructose content of at least 85% by weight relative to the dry solids content of the concentrated and / or purified fructose-rich fraction. (f) Recycle the fructose-rich fraction or the concentrated and / or purified fructose-rich fraction to step (a) or (b); The one or more impurities are any organic compounds other than allulose, fructose, glucose, and sucrose; preferably, the one or more impurities include (i) allulose dimer, allulose-fructobiose, allulose-glucose-biose, allulose tetramer, bisallulose anhydride, levulinic acid, γ-hydroxyvalerate (GVA), furfural, hydroxymethylfurfural (HMF), 2,5-dimethylfuran, 2,5-furandicarboxylic acid (FDCA), 5-hydroxymethylfuran-2-carboxylic acid, 2,5-formylfurancarboxylic acid, 2,5-furandialdehyde, 2,5-bis-(hydroxy-methyl)furan, bis(5-formyl-2-furfural) ether, furan-2-carboxylic acid, furan-3-carboxylic acid, 5-hydroxyfurfural, 2,5-dihydro-2,5-dimethoxyfuran, (2R)-5-oxotetrahydro-2-furancarboxylic acid, bis(5-methylfurfural) ether, 5,5'-methylene-di(furan-2-carboxylic acid) or any combination thereof; and / or (ii) Lactic acid, maltol, furanol, allol, glucone (2-keto-D-glucose), 1-deoxyglucone, 3-deoxyglucone, 3-deoxygalactone, formic acid, acetic acid, propionic acid, glyoxal, or any combination thereof; and / or (iii) 2,3-Butanedione, acetaldehyde, 2-keto-D-glucose (glucose ketone), 3-deoxyglucose ketone or any combination thereof.

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