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WO2025153524A1 - Procédé de synthèse et de purification d'allulose - Google Patents

Procédé de synthèse et de purification d'allulose

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Publication number
WO2025153524A1
WO2025153524A1 PCT/EP2025/050865 EP2025050865W WO2025153524A1 WO 2025153524 A1 WO2025153524 A1 WO 2025153524A1 EP 2025050865 W EP2025050865 W EP 2025050865W WO 2025153524 A1 WO2025153524 A1 WO 2025153524A1
Authority
WO
WIPO (PCT)
Prior art keywords
ppmw
allulose
fraction
fructose
process according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/EP2025/050865
Other languages
English (en)
Inventor
Thomas HÄSSLER
Peter ZETLAU
Sebastian HANFT
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Savanna Ingredients GmbH
Original Assignee
Savanna Ingredients GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Savanna Ingredients GmbH filed Critical Savanna Ingredients GmbH
Publication of WO2025153524A1 publication Critical patent/WO2025153524A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/02—Monosaccharides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
    • B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
    • B01D15/1814—Recycling of the fraction to be distributed
    • B01D15/1821—Simulated moving beds
    • B01D15/185—Simulated moving beds characterised by the components to be separated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/02—Monosaccharides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y501/00—Racemaces and epimerases (5.1)
    • C12Y501/03—Racemaces and epimerases (5.1) acting on carbohydrates and derivatives (5.1.3)

Definitions

  • the starting material may contain other carbohydrates.
  • sucrose When the fructose is obtained from sucrose, sucrose may be cleaved into a 1: 1 mixture of fructose and glucose (invert sugar), and the glucose may be separated from the fructose, e.g. by chromatography.
  • the glucose may first be isomerized into fructose under enzymatic catalysis of a suitable isomerase and subsequently, merely the residual, i.e. not isomerized glucose may be separated from the fructose, e.g. by chromatography. In either case, the thus purified fructose may still contain certain amounts of glucose and/or sucrose.
  • the starch or cellulose may first be degraded into glucose and subsequently be isomerized into fructose under enzymatic catalysis of a suitable isomerase. Subsequently, the residual, i.e. not isomerized glucose may likewise be separated from the fructose, e.g. by chromatography. Under these circumstances, the thus purified fructose may still contain certain amounts of glucose and/or glucooligosaccharides and/or cellooligosaccharides.
  • WO 2021 146134 Al relates to a method comprising separating a mixture of allulose, fructose, glucose, and glucooligosaccharides, wherein the separating comprises using simulated moving bed chromatography, and recovering allulose at a high purity and yield.
  • WO 2022 239027 Al relates to a system and method for purifying D-allulose and/or fructose from a binary mixture.
  • EP 3 553 069 Al relates to a method for utilizing fructose raffinate obtained in the process for separating psicose conversion product with a high purity chromatography in the process for preparing psicose.
  • FR 3 061 413 Al relates to a process for the manufacture of D-allulose crystals which makes it possible to work continuously and to obtain a high yield. It further relates to the use of a nanofiltration unit in a process for producing D-allulose crystals in order to improve the yield and/or the quality of the crystals obtained.
  • US 11 401 292 B2 relates to a method for preparing a crystalline functional sweetener for raising the crystallization yield and increasing the particle size by controlling the content of impurities or production of impurities comprised in a solution for preparing the crystal.
  • the process should allow for economic preparation of allulose products with high purity on industrial scale. Disposal of valuable substances such as residual fructose should be minimized.
  • a first aspect of the invention relates to a process for the preparation of an allulose product comprising the steps of
  • (P) optionally, one or more impurities and/or glucose and/or sucrose;
  • step (e) optionally, subjecting the fructose enriched fraction to one or more concentration and/or purification measures thereby obtaining a concentrated and/or purified fructose enriched fraction having a fructose content of at least 85 wt.-%, relative to the dry solids content of the concentrated and/or purified fructose enriched fraction; (f) recirculating the fructose enriched fraction or the concentrated and/or purified fructose enriched fraction to step (a) or (b); wherein the one or more impurities are any organic compounds other than allulose, fructose, glucose, and sucrose.
  • the process according to the invention comprises steps (a), (b), (d) and (f), and optionally also
  • the process comprises steps (a), (b), (c), (d) and (f); or (a), (b),
  • the process steps are performed in alphabetical order.
  • the process is performed as a batch process.
  • the process is performed as a semi-batch process.
  • the process is performed continuously.
  • one or more of the process steps may be performed simultaneously or at least partially simultaneously.
  • impurities are any organic compounds other than allulose, fructose, glucose, and sucrose.
  • step (d) the crude product or the pre-purified product is chroma- tographically separated into
  • the allulose product is solid, preferably at least partially crystalline.
  • a starting composition comprising (a) fructose and ( ) optionally, one or more impurities and/or glucose and/or sucrose.
  • the starting composition has a fructose content of at least 40 wt.-%, preferably at least 60 wt.-%, more preferably at least 70 wt.-%, yet more preferably at least 80 wt.-%, even more preferably at least 90 wt.-%, most preferably at least 95 wt.-%, and in particular at least 98 wt.-%, relative to the dry solids content of the starting composition.
  • the starting composition comprises glucose.
  • the starting composition has a glucose content of at most 8.0 wt.-%, preferably at most 7.0 wt.-%, more preferably at most 6.0 wt.-%, yet more preferably at most 5.0 wt.-%, even more preferably at most 4.0 wt.-%, most preferably at most 3.0 wt.-%, and in particular at most 2.0 wt.-%, relative to the dry solids content of the starting composition.
  • the starting composition has a glucose content of at least 0.0001 wt.-%, preferably at least 0.001 wt.-%, more preferably at least 0.01 wt.-%, yet more preferably at least 0.1 wt.-%, even more preferably at least 0.2 wt.-%, most preferably at least 0.3 wt.-%, and in particular at least 0.4 wt.- %, relative to the dry solids content of the starting composition.
  • the starting composition has a sucrose content of at most 1.8 wt.-%, preferably at most 1.6 wt.-%, more preferably at most 1.4 wt.-%, yet more preferably at most 1.2 wt.-%, even more preferably at most 1.0 wt.-%, most preferably at most 0.8 wt.-%, and in particular at most 0.6 wt.-%, relative to the dry solids content of the starting composition.
  • step (b) pf the process according to the invention the starting composition provided in step (a) is contacted with an allulose-3 -epimerase to convert fructose into allulose thereby obtaining a crude product comprising (a) allulose, ( ) fructose, and (y) one or more impurities and/or glucose and/or sucrose.
  • the one or more impurities comprise allulose dimer, allulose-fructose disaccharide, allulose-glucose disaccharide, allulose tetramer, diallulose anhydride, levulinic acid, y-hydroxy valeric acid (GVA), furfural, hydroxymethyl furfural (HMF), 2,5-dimethylfurane, 2,5-furane dicarboxylic acid (FDCA), 5 -hydroxymethyl furane 2-carboxylic acid, 2,5-formyl furane carboxylic acid, 2,5-furane dialdehyde, 2,5-bis-(hydroxy-methyl)furane, bis(5-formyl-2-furfuryl)ether), furane-2-carboxylic acid, furane-3 -carboxylic acid, 5 -hydroxyfurfural, 2,5-dihydro-2,5-dimethoxyfurane, (2R)-5-oxote
  • the one or more impurities comprise 2,3-butanedione, acetaldehyde, 2-keto-D-glu- cose (glucosone), 3 -desoxyglucosone, or any combination thereof.
  • the one or more impurities comprise 2-keto-D-glucose (glucosone), i.e.
  • the crude product has a glucose content of at most 8.0 wt.-%, preferably at most 7.0 wt.-%, more preferably at most 6.0 wt.-%, yet more preferably at most 5.0 wt.-%, even more preferably at most 4.0 wt.-%, most preferably at most 3.0 wt.-%, and in particular at most 2.0 wt.-%, relative to the dry solids content of the crude product.
  • the crude product has a sucrose content of at most 5.00 wt.-%, preferably at most 4.25 wt.-%, more preferably at most 3.50 wt.-%, yet more preferably at most 2.75 wt.-%, even more preferably at most 2.00 wt.-%, most preferably at most 1.25 wt.-%, and in particular at most 0.50 wt.- %, relative to the dry solids content of the crude product.
  • step (c) of the process according to the invention the crude product obtained in step (b) is subjected to one or more pre-purification measures thereby obtaining a pre-purified product comprising (a) allulose, ( ) fructose, and (y) one or more impurities and/or glucose and/or sucrose.
  • the one or more pre-purification measures comprise a filtration, preferably an ultrafiltration.
  • Suitable methods for filtration including ultrafiltration are known to the skilled person and suitable membranes are commercially available. Typical membranes and pore filters have separation limits between 0.1 and 0.01 pm.
  • step (d) of the process according to the invention the crude product obtained in step (b) or the pre-purified product obtained in optional step (c) is chromatographically separated into
  • (y) optionally, a purge fraction enriched with one or more impurities and/or glucose and/or sucrose.
  • the crude product obtained in step (b) or the pre-purified product obtained in optional step (c) that is subjected to chromatographic separation (a) has a dry solids content (dry substance content) within the range of 55.0 ⁇ 15.0 wt.-%, preferably 55.0 ⁇ 13.0 wt.-%, more preferably 55.0 ⁇ 11.0 wt.-%, still more preferably 55.0 ⁇ 9.0 wt.-%, yet more preferably 55.0 ⁇ 7.0 wt.-%, even more preferably 55.0 ⁇ 6.0 wt.-%, most preferably 55.0 ⁇ 5.0 wt.-%, and in particular 55.0 ⁇ 4.0 wt.-%, relative to the total weight of the crude product and the prepurified product, respectively; and/or
  • (P) has an allulose content within the range of 30.0 ⁇ 12.0 wt.-%, preferably 30.0 ⁇ 11.0 wt.-%, more preferably 30.0 ⁇ 10.0 wt.-%, still more preferably 30.0 ⁇ 9.0 wt.-%, yet more preferably 30.0 ⁇ 8.0 wt.-%, even more preferably 30.0 ⁇ 7.0 wt.-%, most preferably 30.0 ⁇ 6.0 wt.-%, and in particular 30.0 ⁇ 5.0 wt.-%, relative to the dry solids content of the crude product and the pre-purified product, respectively; and/or
  • (a) has a sucrose content within the range of 0.50 ⁇ 0.50 wt.-%, preferably 0.50 ⁇ 0.45 wt.-%, more preferably 0.50 ⁇ 0.40 wt.-%, still more preferably 0.50 ⁇ 0.35 wt.-%, yet more preferably 0.50 ⁇ 0.30 wt.-%, even more preferably 0.50 ⁇ 0.25 wt.-%, most preferably 0.50 ⁇ 0.20 wt.-%, and in particular 0.50 ⁇ 0. 15 wt. -%, relative to the dry solids content of the crude product and the pre-purified product, respectively.
  • fructose enriched fraction wherein relative to the dry solids content of the fructose enriched fraction, the content of fructose is within the range of from 90 to 100 wt.-%, the content of allulose is within the range of from 0 to 5 wt.-% (50000 ppmw), and the content of glucose is within the range of from 0 to 1.5 wt.-% (15000 ppmw).
  • the SMB is characterized by the ratio of the volume of fresh water to the volume of feed, i.e. the water to feed ratio. According to the invention, a low value for the water to feed ratio (v/v) of the SMB is desirable.
  • the extract to raffinate ratio (v/v) of the SMB is at least 0.25, more preferably at least 0.30, still more preferably at least 0.35, yet more preferably at least 0.40, even more preferably at least 0.45, most preferably at least 0.50, and in particular at least 0.55.
  • the purity of allulose in the extract is at least 93%, more preferably at least 94%, still more preferably at least 95%, yet more preferably at least 96%, even more preferably at least 97%, most preferably at least 98%, and in particular at least 99%.
  • the purity of allulose is determined by HPLC according to ICUMSA GS3-50.
  • the flow of the purge fraction preferably amounts to at most 9.0 wt.-% of the flow of the first allulose enriched fraction, preferably at most 8.0 wt.-%, still more preferably at most 7.0 wt.-%, yet more preferably at most 6.0 wt.-%, even more preferably at most 5.0 wt.-%, most preferably at most 4.0 wt.-%, and in particular at most 3.0 wt.-%.
  • the flow of the purge fraction preferably amounts to at most 9.0 wt.-% of the flow of the fructose enriched fraction, preferably at most 8.0 wt.-%, still more preferably at most 7.0 wt.-%, yet more preferably at most 6.0 wt.-%, even more preferably at most 5.0 wt.-%, most preferably at most 4.0 wt.-%, and in particular at most 3.0 wt.-%.
  • the flow of the purge fraction preferably amounts to at most 9.0 wt.-% of the flow of the second allulose enriched fraction, preferably at most 8.0 wt.-%, still more preferably at most 7.0 wt.-%, yet more preferably at most 6.0 wt.-%, even more preferably at most 5.0 wt.-%, most preferably at most 4.0 wt.-%, and in particular at most 3.0 wt.-%.
  • the one or more allulose enriched fractions independently of one another have an allulose content of at least 87.5 wt.-%, preferably at least 90.0 wt.-%, more preferably at least 92.5 wt.- %, yet more preferably at least 95.0 wt.-%, even more preferably at least 97.5 wt.-%, most preferably at least 98.5 wt.-%, and in particular at least 99.0 wt.-%, relative to the dry solids content of the one or more allulose enriched fractions.
  • the one or more allulose enriched fractions independently of one another have a content of hydroxymethyl furfural (HMF) of at most 1000 ppmw, preferably at most 800 ppmw, more preferably at most 600 ppmw, yet more preferably at most 400 ppmw, even more preferably at most 200 ppmw, most preferably at most 100 ppmw, and in particular at most 50 ppmw, relative to the dry solids content of the one or more allulose enriched fractions.
  • HMF hydroxymethyl furfural
  • the one or more allulose enriched fractions independently of one another have a content of 2,3-butanedione of at most 1000 ppmw, preferably at most 800 ppmw, more preferably at most 600 ppmw, yet more preferably at most 400 ppmw, even more preferably at most 200 ppmw, most preferably at most 100 ppmw, and in particular at most 50 ppmw, relative to the dry solids content of the one or more allulose enriched fractions.
  • the one or more allulose enriched fractions independently of one another have a content of allosone of at most 1000 ppmw, preferably at most 800 ppmw, more preferably at most 600 ppmw, yet more preferably at most 400 ppmw, even more preferably at most 200 ppmw, most preferably at most 100 ppmw, and in particular at most 50 ppmw, relative to the dry solids content of the one or more allulose enriched fractions.
  • the fructose enriched fraction has a fructose content of at least 70.0 wt.-%, preferably at least 72.5 wt.-%, more preferably at least 75.0 wt.-%, yet more preferably at least 77.5 wt.-%, even more preferably at least 80.0 wt.-%, most preferably at least 82.5 wt.-%, and in particular at least 85.0 wt.-%, relative to the dry solids content of the fructose enriched fraction.
  • the fructose enriched fraction has an allulose content of at most 12.5 wt.-%, preferably at most 7.5 wt.-%, more preferably at most 5.0 wt.-%, yet more preferably at most 2.5 wt.-%, even more preferably at most 1.0 wt.-%, most preferably at most 0.1 wt.-%, and in particular at most 0.01 wt.-%, relative to the dry solids content of the fructose enriched fraction.
  • the fructose enriched fraction has a total content of impurities of at most 4.5 wt.-%, preferably at most 4.0 wt.-%, more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.- %, even more preferably at most 2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.-%, relative to the dry solids content of the fructose enriched fraction.
  • the fructose enriched fraction has a sucrose content of at most 3.0 wt.-%, preferably at most 2.0 wt.-%, more preferably at most 1.5 wt.-%, yet more preferably at most 1.0 wt.-%, even more preferably at most 0.5 wt.-%, most preferably at most 0.1 wt.-%, and in particular at most 0.01 wt.-%, relative to the dry solids content of the fructose enriched fraction.
  • the fructose enriched fraction preferably second purge fraction
  • the fructose enriched fraction has a content of hydroxymethyl furfural (HMF) of at most 10,000 ppmw, preferably at most 8,000 ppmw, more preferably at most 6,000 ppmw, yet more preferably at most 4,000 ppmw, even more preferably at most 3,000 ppmw, most preferably at most 2,000 ppmw, and in particular at most 1,500 ppmw, relative to the dry solids content of the fructose enriched fraction.
  • HMF hydroxymethyl furfural
  • the fructose enriched fraction has a content of hydroxymethyl furfural (HMF) of at most 1000 ppmw, preferably at most 800 ppmw, more preferably at most 600 ppmw, yet more preferably at most 400 ppmw, even more preferably at most 200 ppmw, most preferably at most 100 ppmw, and in particular at most 50 ppmw, relative to the dry solids content of the fructose enriched fraction.
  • HMF hydroxymethyl furfural
  • the fructose enriched fraction has a content of 2,3-butanedione of at most 10,000 ppmw, preferably at most 8,000 ppmw, more preferably at most 6,000 ppmw, yet more preferably at most 4,000 ppmw, even more preferably at most 3,000 ppmw, most preferably at most 2,000 ppmw, and in particular at most 1,500 ppmw, relative to the dry solids content of the fructose enriched fraction.
  • the fructose enriched fraction has a content of 2,3-butanedione of at most 1000 ppmw, preferably at most 800 ppmw, more preferably at most 600 ppmw, yet more preferably at most 400 ppmw, even more preferably at most 200 ppmw, most preferably at most 100 ppmw, and in particular at most 50 ppmw, relative to the dry solids content of the fructose enriched fraction.
  • the purge fraction has a total content of impurities of at least 0.001 wt.-%, preferably at least 0.01 wt.-%, more preferably at least 0.1 wt.-%, yet more preferably at least 0.5 wt.-%, even more preferably at least 1.0 wt.-%, most preferably at least 1.5 wt.-%, and in particular at least 2.0 wt.-%, relative to the dry solids content of the purge fraction.
  • the purge fraction has an allulose content of at most 5.0 wt.-%, preferably at most 3.5 wt.-%, more preferably at most 2.0 wt.-%, yet more preferably at most 1.0 wt.-%, even more preferably at most 0.5 wt.-%, most preferably at most 0. 1 wt.-%, and in particular at most 0.01 wt.-%, relative to the dry solids content of the purge fraction.
  • the purge fraction has a fructose content of at most 95 wt.-%, preferably at most 90 wt.-%, more preferably at most 85 wt.-%, yet more preferably at most 80 wt.-%, even more preferably at most 75 wt.-%, most preferably at most 70 wt.-%, and in particular at most 65 wt.-%, relative to the dry solids content of the purge fraction.
  • the purge fraction has a fructose content of at most 5.0 wt.-%, preferably at most 3.5 wt.-%, more preferably at most 2.0 wt.-%, yet more preferably at most 1.0 wt.-%, even more preferably at most 0.5 wt.-%, most preferably at most 0.1 wt.-%, and in particular at most 0.01 wt.-%, relative to the dry solids content of the purge fraction.
  • the purge fraction has a glucose content of at most 99 wt.-%, preferably at most 95 wt.-%, more preferably at most 90 wt.-%, yet more preferably at most 85 wt.-%, even more preferably at most 80 wt.-%, most preferably at most 75 wt.-%, and in particular at most 70 wt.-%, relative to the dry solids content of the purge fraction.
  • the purge fraction has a sucrose content of at most 95 wt.-%, preferably at most 84 wt.-%, more preferably at most 73 wt.-%, yet more preferably at most 62 wt.-%, even more preferably at most 51 wt.-%, most preferably at most 40 wt.-%, and in particular at most 30 wt.-%, relative to the dry solids content of the purge fraction.
  • the purge fraction preferably first purge fraction
  • the purge fraction has a content of hydroxymethyl furfural (HMF) of at least 1 ppmw, preferably at least 5 ppmw, more preferably at least 10 ppmw, yet more preferably at least 25 ppmw, even more preferably at least 50 ppmw, most preferably at least 100 ppmw, and in particular at least 250 ppmw, relative to the dry solids content of the purge fraction.
  • HMF hydroxymethyl furfural
  • the purge fraction has a content of acetaldehyde of at least 1 ppmw, preferably at least 5 ppmw, more preferably at least 10 ppmw, yet more preferably at least 25 ppmw, even more preferably at least 50 ppmw, most preferably at least 100 ppmw, and in particular at least 250 ppmw, relative to the dry solids content of the purge fraction.
  • step (e) of the process according to the invention the fructose enriched fraction obtained in step (d) is subjected to one or more concentration and/or purification measures thereby obtaining a concentrated and/or purified fructose enriched fraction having a fructose content of at least 85 wt.-%, relative to the dry solids content of the concentrated and/or purified fructose enriched fraction.
  • the fructose enriched fraction or the concentrated and/or purified fructose enriched fraction is recirculated to step (b).
  • the process according to the invention additionally comprises the steps of
  • the process according to the invention additionally comprises the step of (k) recirculating the liquid phase to the crude product or the pre-purified product for subsequent chromatographic separation in step (d).
  • step (d) comprises the sub-steps
  • step (g) (1) recirculating the washing water to the at least one of the one or more allulose enriched fractions for subsequent concentration in step (g).
  • Another aspect of the invention relates to a process for the preparation of an allulose product comprising the steps of
  • pre-purified product comprising (a) allulose, (P) fructose, and (y) one or more impurities and/or glucose and/or sucrose;
  • step (f) recirculating the fructose enriched fraction or the concentrated and/or purified fructose enriched fraction to step (a) or (b); wherein the one or more impurities are any organic compounds other than allulose, fructose, glucose, and sucrose; preferably wherein the one or more impurities comprise
  • the fructose enriched fraction is preferably concentrated in first concentration unit (8), e.g. by reverse osmosis and/or evaporation, and subsequently, preferably supplied to second demineralization/decoloring unit (9) before the thus obtained concentrated and/or purified fructose enriched fraction is preferably recirculated to mixing unit (3).
  • first concentration unit (8) e.g. by reverse osmosis and/or evaporation
  • second demineralization/decoloring unit (9) before the thus obtained concentrated and/or purified fructose enriched fraction is preferably recirculated to mixing unit (3).
  • One or more impurities and/or glucose and/or sucrose that may have been present and/or that may have been produced in the course of enzymatic conversion and/or subsequent work-up measures and that may not have been completely separated from the fructose enriched fraction by simulated moving bed chromatography are thus recirculated to mixing unit (3) as well. This is one possible source, among others,
  • the ratio of the volume of water to the volume of feed, i.e. the water to feed ratio, is another important parameter that is advantageously adjusted in order to optimize efficiency of the chromatography. The lower the water to feed ratio, the more concentrated to solutions that are chromatographically separated from one another (i.e. the higher their solids content) and the lower the energy consumption for subsequent water evaporation.
  • Raffinate i.e. a fructose enriched fraction orthe intermediate fraction, respectively
  • extract i.e. an allulose enriched fraction
  • the ratio of the volume of the extract (product) to the volume of the raffinate, i.e. the extract to raffinate ratio, is a further important parameter that is advantageously adjusted in order to optimize efficiency of the chromatography.
  • Figure 4 is an elution profile of a sequential simulated moving bed (SSMB) chromatography of Example 1.
  • Figure 5 schematically illustrates the influence of chamber volume of zone I (Cl), chamber volume of zone IV (C4), water to feed ratio (W/F), and extract (product) to raffinate ratio (P/R) on the chromatographic separation, whereas large font indicates an increase and small font indicates a decrease of the respective parameter, and the arrow indicates the direction of the change of the graph for the respective parameter.
  • a test run was carried out to evaluate the possibility of a third cut.
  • the raffinate cut (fructose enriched fraction) was divided into 10 evenly spaced measurement times.
  • the 10 samples of the raffinate cut (fructose enriched fraction) and one sample of the feed were analyzed (HPLC according to ICUMSA GS3-50) in order to determine the absolute contents of the components.
  • Fructose loss can be minimized when a third separation fraction is cut at the beginning of the raffinate cut (fructose enriched fraction).
  • the cut should be selected so that the formation of such unwanted component or the addition of this unwanted component to the system corresponds exactly to the quantity of the third cut. In this way, accumulation is stopped, but at the same time it must be accepted that a certain amount of fructose will also be lost.
  • Example 4 single SSMB with a third separation fraction:

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Abstract

L'invention concerne un procédé de préparation d'un produit d'allulose comprenant la conversion enzymatique du fructose en allulose ; la séparation chromatographique du produit brut ainsi obtenu en (i) une ou plusieurs fractions enrichies en allulose, (ii) une fraction enrichie en fructose, et éventuellement (iii) une fraction de purge, de préférence par chromatographie en lit mobile simulé ; et la recirculation de la fraction enrichie en fructose pour la conversion enzymatique.
PCT/EP2025/050865 2024-01-16 2025-01-15 Procédé de synthèse et de purification d'allulose Pending WO2025153524A1 (fr)

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US4880920A (en) 1985-12-20 1989-11-14 Uop Process for separating ketoses from alkaline-or pyridine-catalyzed isomerization products
US20100213130A1 (en) 2009-02-25 2010-08-26 Danisco A/S Separation process
US20170313734A1 (en) 2014-10-20 2017-11-02 Cj Cheiljedang Corporation Method for preparing d-psicose crystal
WO2018087261A1 (fr) 2016-11-11 2018-05-17 Pfeifer & Langen GmbH & Co. KG Synthèse de d-allulose
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