WO2022239027A1 - Procédé et système de purification de d-allulose et/ou de fructose - Google Patents

Procédé et système de purification de d-allulose et/ou de fructose Download PDF

Info

Publication number
WO2022239027A1
WO2022239027A1 PCT/IN2022/050452 IN2022050452W WO2022239027A1 WO 2022239027 A1 WO2022239027 A1 WO 2022239027A1 IN 2022050452 W IN2022050452 W IN 2022050452W WO 2022239027 A1 WO2022239027 A1 WO 2022239027A1
Authority
WO
WIPO (PCT)
Prior art keywords
column
columns
raffinate
extract
allulose
Prior art date
Application number
PCT/IN2022/050452
Other languages
English (en)
Inventor
Rahul Raju KANUMURU
Muthuvaduganathan NAGASUNDRAM
Binay Kumar Giri
Original Assignee
Petiva Private Limited
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 Petiva Private Limited filed Critical Petiva Private Limited
Publication of WO2022239027A1 publication Critical patent/WO2022239027A1/fr

Links

Classifications

    • 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
    • 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—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns recycling of the fraction to be distributed
    • B01D15/1821—Simulated moving beds
    • B01D15/185—Simulated moving beds characterized by the components to be separated
    • 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
    • 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 present subject matter disclosed herein in general, relates to a process and system for purifying allulose and/or fructose from a mixture obtained in the production of allulose from a sugar source such as sucrose by heterogeneous or homogeneous catalysis which includes chemical and/or enzymatic catalysis.
  • D-allulose (known as D-psicose), a rare sugar and C-3 epimer of fructose, is an ideal sugar substitute and has sweetness like dextrose or 70 % to sucrose. Allulose is when metabolized by a human body, does not raise blood sugar or insulin levels, and provides minimal calories. A caloric value of allulose is 0.2 kcal per gram and prevents the formation of body fat. Further, it has been reported that allulose is non-cariogenic. Thus, allulose is of great interest in the nutraceutical applications.
  • Allulose can be produced by chemical or enzymatic processes.
  • the processes for preparing allulose from a sugar source, preferably from fructose, according to the prior art are not satisfactory in every aspect and there is a need for improvements, and there is presently no industrially applicable method for producing D-allulose.
  • KA absorption coefficient
  • the conventional apparatus and method have less productivity to get desire (more than 97%) purity in extract phase, thereby decreasing the efficiency of the apparatus and process.
  • present disclosure relates to a method and a system for separating allulose from a sugar mixture.
  • present disclosure relates to a method and a system for purifying D-allulose from a sugar mixture.
  • the system is configured to purify D- allulose and/or fructose from a binary sugar mixture obtained in the production of D-allulose from a sugar source such as sucrose.
  • the present disclosure relates to a method and a system for purifying D-allulose from a mixture obtained in the production of D-allulose from a sugar source such as sucrose.
  • the process for producing D-allulose from sugar source comprises the steps of: (i) mixing the sugar source with water or with an aqueous liquid and adjusting the concentration of dissolved sugar, such as sucrose thereby providing a first solution of sugar source; (ii) converting sucrose to glucose and fructose, under heterogeneous or homogeneous catalysis which includes chemical and/or enzymatic catalysis thereby providing a second solution comprising glucose and fructose; and (iii) converting fructose of the second solution to D-allulose under enzymatic catalysis thereby providing a mixture comprising fructose and allulose.
  • the present disclosure provides a method for purifying allulose from a mixture in a system comprising continuous simulated moving bed (SMB) apparatus comprising four or more columns positioned adjacent to each other and fluidly connected in series forming a closed loop configuration, the method comprises the steps of: i) providing a feed mixturecomprising the allulose and one or more of its isomers; and ii) simultaneously, a) continuously feeding the mixture of step i) through a feed port into the simulated moving bed chromatographic (SMB) apparatus comprising four or more columns; b) continuously feeding eluent into the apparatus through an eluent port; c) continuously withdrawing the extract through an extract port; and d) continuously withdrawing the raffinate through a raffinate port.
  • SMB simulated moving bed
  • the present disclosure relates to a process for producing pure D-allulose from sugar source, the process comprises:
  • Figure 2 schematically illustrates a process for producing allulose according to an embodiment of the present disclosure
  • Figure 3 illustrates HPLC chromatogram of raffinate phase in accordance with example 1 of the present disclosure
  • Figure 4 illustrates HPLC chromatogram of extract phase in accordance with example 1 of the present disclosure
  • Figure 5 illustrates HPLC chromatogram of extract phase in accordance with an example 1 of the present disclosure
  • Figure 6 illustrates HPLC chromatogram of raffinate phase in accordance with example 1 of the present disclosure
  • Figure 7 illustrates HPLC chromatogram of extract phase in accordance with example 2 of the present disclosure
  • Figure 8 illustrates HPLC chromatogram of extract phase in accordance with example 2 of the present disclosure
  • Figure 9 illustrates HPLC chromatogram of raffinate phase in accordance with an example 2 of the present disclosure
  • Figure 1 illustrates HPLC chromatogram of raffinate phase in accordance with example 2 of the present disclosure.
  • Figure 12 illustrates HPLC chromatogram of extract phase in accordance with an example 2 of the present disclosure.
  • the present disclosure relates to a method and a system for purifying D-allulose from a mixture.
  • the system is configured to purify D- allulose and/or fructose from a binary sugar mixture obtained in the production of D-allulose from a sugar source such as sucrose.
  • the present disclosure relates to a method and a system for purifying D-allulose from a mixture obtained in the production of D-allulose from a sugar source such as sucrose.
  • the process for producing D-allulose from sugar source comprises the steps of: (i) mixing the sugar source with water or with an aqueous liquid and adjusting the concentration of dissolved sugar, preferably sucrose thereby providing a first solution of sugar source;(ii) converting sucrose to glucose and fructose, under heterogeneous or homogeneous catalysis which includes chemical and/or enzymatic catalysis thereby providing a second solution comprising glucose and fructose; and(iii) converting fructose of the second solution to D-allulose under enzymatic catalysis thereby providing a mixture comprising fructose and allulose.
  • the detailed procedure for the conversion of sucrose to glucose, and fructose to allulose is well known in the art.
  • the system generally identified by reference numeral 100.
  • the system 100 is more particularly, but not exclusively used for separating sugars and to obtain about 80% to about 97% allulose from a binary mixture. It is believed that those skilled in the art will readily recognize that as the description proceeds, such systemlOO may be utilized also for obtaining allulose continuously from a sugar mixture comprising the allulose, one or more isomers of allulose, optionally one or more additional sugars.
  • the systemlOO comprises of a feed tank 10, at least one eluent tank 20, and a simulated moving bed chromatographic (SMB) apparatus 30.
  • SMB simulated moving bed chromatographic
  • a feed tank 10 configured to contain and store the sugar mixture [interchangeably referred as “mixture”].
  • the sugar mixture comprises allulose, one or more isomers of allulose, optionally one or more additional sugars.
  • the feed tank 10 is in fluid communication with each of the four or more columns of the simulated moving bed chromatographic (SMB) apparatus 30.
  • the feed tank is configured to continuously feed the mixture into at least one of the four or more columns of the SMB apparatus 30.
  • the mixture is supplied to at least one of the four or more columns via at least one pump 11.
  • the feed tank 10 is in fluid flow communication with at least one first pre-heater 12.
  • the first pre-heater 12 is disposed between the feed tank 10 and the at least one of four or more columns.
  • the first pre heater 12 is used for heating the mixture to a first pre-determined temperature prior to supplying the mixture into the at least one of four or more columns.
  • the first pre-determined temperature may be about 50-70 °C.
  • the system 100 further comprises an eluent tank 20 to store eluent.
  • the eluent may be water and any other suitable eluent may be used to meet the requirement.
  • the eluent tank 20 is in fluid flow communication with each of the four or more columns of the SMB apparatus 30.
  • the eluent tank 20 is configured to continuously feed the eluent into at least one of the four or more columns of the SMB apparatus 30.
  • the eluent is supplied to at least one of the four more columns via at least one pump 21 as shown in Figure 1.
  • the eluent tank 20 may be in fluid flow communication with at least one second pre-heater23 via at least one pump 21.
  • the at least one second preheater 23 is configured to heat the eluent at a second predetermined temperature before the eluent is supplied to at least one of the four or more columns.
  • the second predetermined temperature of the eluent may be about 50-70 °C.
  • the system 100 comprises a raffinate tank 50fluidly connected with each of the four or more columns of the SMB apparatus 30.
  • the raffinate tank 50 is configured to continuously withdraw the raffinate from at least one of the four or more columns via a raffinate port lg to 8g of the SMB apparatus 30.
  • the raffinate is withdrawn from at least one of the four more columns via at least one pump 51 as shown in Figure 1.
  • the raffinate comprises one or more isomers of allulose.
  • the raffinate comprises glucose and fructose which is about 95%pure.
  • the system 100 includes an extract tank 40 fluidly connected with each of the four or more columns of the SMB apparatus 30.
  • the extract tank 40 is configured to continuously withdraw the extract from at least one of the four or more columns via an extract port If to 8f.
  • the extract is withdrawn from at least one of the four more columns via at least one pump 41 as shown in Figure 1.
  • the extract comprises allulose.
  • the extract comprises allulose which is about 95% pure.
  • the system 100 comprises the continuous simulated moving bed (SMB) apparatus 30.
  • the SMB apparatus 30 includes four or more columns positioned adjacent to each other and are fluidly connected in series forming a closed loop configuration.
  • the system may include minimum of four columns and maximum of eight or more columns and there is no limitation in higher side.
  • the SMB apparatus 30 may include eight columns which comprises a first column Cl, a second column C2, a third column C3, a fourth column C4, a fifth column C5, a sixth column C6, a seventh column C7 and an eighth column C8 and so on.
  • the columns Cl to C8 are connected to each other in series and further the eighth column C8 or last column is connected to first column Cl to form the closed loop configuration.
  • the columns of the SMB apparatus 30 employ a chromatographic separation system to obtain the D-allulose.
  • Each of the columnsCl to C8 of the SMB apparatus 30 is configured vertically.
  • the columns Cl to C8 may have hollow elongated structure to enclose a resin bed and securely support other components required to perform chromatographic separation to obtain the D- allulose.
  • each column Cl to C8 is configured to react with the mixture when supplied by the feed tank 10.
  • the resin in the resin bed is calcium-based resin.
  • Each of the four or more columns is surrounded by a jacket le. The jacket le aids in maintaining a required temperature within the column. In an embodiment, the jacket leencloses the column Cl to C8.
  • each of the four or more columns, Cl to C8 as per Figure 1 comprises a feed port la, 2a, 3a, 4a, 5a, 6a 7a and 8a and an eluent port lb, 2b, 3b, 4b, 5b, 6b, 7b and 8b.
  • the feed port la to 8a of each column Cl to C8 is in fluid flow communication with the feed tank 10 for supplying the mixture via the first preheater 12at the first predetermined temperature.
  • the eluent port lb to 8b of each column Cl toC8 is in fluid flow communication with the eluent tank 20 via the second pre-heater 23 to supply the eluent at the second predetermined temperature.
  • the feed port and the eluent port may be provided at one end the four or more columns Cl to C8.
  • Each column of the four or more columns comprises at least one inlet valve manifolds fluidly connected to the each of the feed port la to 8a and the eluent port lb to 8b for selectively receiving the sugar mixture and the eluent from the feed tank and the eluent tank, respectively.
  • the inlet valves manifolds include a first inlet valve lc, 2c, 3c, 4c, 5c, 6c, 7c and 8c and second inlet valve Id, 2d, 3d, 4d, 5d, 6d, 7d and 8d.
  • the first inlet valve lc to 8c may be disposed between the first preheater 12 and the feed port la to 8a.
  • the second inlet valve Id to 8d may be disposed between the second preheater 12 and the eluent port la to 8a.
  • the at least one first inlet valve and the second inlet valve is configured to control or regulate the supply of at least one of the mixtures and the eluent via feed port and the eluent port from the feed tank 10 and the eluent tank 20.
  • Each column of the four or more columns Cl to C8are comprises with the extract port If to 8f, and the raffinate port lg to 8g.
  • the extract port If to 8f and the raffinate portlg to 8g enablescontinuous withdrawal of extract and raffinate, respectively.
  • the extract port If to 8f and the raffinate ports lg to 8g may be provided at another end of each of the four or more column Cl to C8.
  • Each column of the four or more columns comprises at least one outlet valve manifolds fluidly connected to the each of the extract port If to 8f and the raffinate port lg to 8g for selectively withdrawing and supplying the extract and raffinate to the extract tank 40 and the raffinate tank, respectively.
  • the outlet valves manifolds include a first outlet valve li to 8i and second outlet valve lj to 8j.
  • the first outlet valve li to 8i may be disposed between the at least one pump 41 and the extract port If to 8f.
  • the second outlet valve lj to 8j may be disposed between the at least one pump 51 and the raffinate port lg to 8g.
  • the at least one first outlet valve li to 8iand the second outlet valve lj to 8jmanifolds are configured to control or regulate the supply of withdrawn extract and the raffinate via extract port 1 f to 8f and the raffinate port lg to 8g into the extract tank 40 and the raffinate tank 50.
  • first and second inlet (lc to 8c and Id to 8d) and the first and second outlet valve (li to 8i and lj to 8j) manifolds may be manually operated or actuator- controlled e.g., programmable logic controller (PLC).
  • PLC programmable logic controller
  • the feeding of the sugar mixture and the eluent into the four or more columns Cl to C8, and withdrawal of the extract and the raffinate from the four or more columns Cl to C8, are incremented in series towards adjacent columns, at a predetermined time intervals.
  • the first preheaterl2, the second preheater23 comprises at least one temperature sensor (not shown in figures) to detect the temperature of the mixture and the eluent that is supplied to the four or more columns Cl to C8.
  • each of the four or more columns is provided with a liquid distributor lh to 8h to allow uniform distribution of the mixture and the eluent within the four or more columns Cl to C8.
  • the liquid distributor lh to 8h may be disposed at a portion of either ends within each of the four or more column Cl to C8.
  • the system 100 includes an auxiliary tank 60to store and circulate a fluid, at a predetermined temperature, into jackets le to 8esurroundingeach of the four or more columns Cl to C8.
  • the fluid may be water, or any suitable fluid known in the art.
  • the pre determined temperature of the fluid may be about 50-70 °C.
  • the system 100 may comprises at least one refractive index detector (not shown in figures) coupled to each column Cl to C8to detect and monitor properties of the eluent and the mixture within each column Cl to C 8.
  • the properties of the eluent and the mixture may include, temperatures, concentrations, viscosity, flow rate, quantity, time period and the like.
  • the system 100 includes at least one controller communicatively coupled to at least one pump 11, 21, 41, 51 and the inlet/ outlet valve manifolds.
  • the controller actuates the at least one pump 11, 21 to supply the mixture and the eluent, into each column Cl to C8 from the feed tank 10, and the eluent tank 20.
  • the pumps 41 and 51 are actuated to withdraw and collect the extract, and the raffinate into extract tank 40 and the raffinate tank 50, respectively.
  • the controller coupled with the first and second inlet valve (lc to 8c and Id to 8d) and the first and second outlet valve (li to 8i and lj to 8j) is configured to control and monitor the flow of the feed, eluent, extract and the raffinate, respectively.
  • the controller is coupled to the at least one temperature sensor and the refractive index detector to detect temperature and the properties of the feed and the eluent supplied to each of the four or more columnsCl to C8. Further, the controller is connected with at least one display unit (not shown in figures) for displaying the detected parameters such as temperature, properties etc of the feed and the eluent, extract and raffinate.
  • the system further includes a recirculation pump disposed between and in fluid communication with a last column and a first column of the four or more columns C 1 to C8.
  • the recirculation pump configured in between last and first column aids to transfer the sugar solution from one column to another column.
  • design, and dimensions of components of the system 100 such as the feed tank 10, eluent tank 20, the four or more columns Cl to C8, raffinate tank 50, extract tank 40, preheaters 21, 23 etc., can be altered based on the requirements/application.
  • the present disclosure further provides a method for purifying D-allulose from a mixture.
  • the method is used for separating sugars to obtain about 80% to about 100% of allulose from the mixture.
  • the mixture is a binary mixture comprising sugars.
  • the mixture comprises allulose, one or more isomers of allulose, and optionally one or more additional sugars.
  • thepresent disclosure provides a method for purifying allulose from a mixture (also referred to as “feed mixture”) in a system comprising a continuous simulated moving bed (SMB) apparatus comprising four or more columnspositioned adjacent to each other and fluidly connected in series forming a closed loop configuration.
  • a mixture also referred to as “feed mixture”
  • SMB continuous simulated moving bed
  • the method comprises the steps of: i) providing a feed mixture comprising the allulose and one or more of its isomers; and ii) simultaneously, a) continuously feeding the mixture of step i) through a feed port into the simulated moving bed chromatographic (SMB) apparatus comprising four or more columns; b) continuously feeding eluent into the apparatus through an eluent port; c) continuously withdrawing the extract through an extract port; and d) continuously withdrawing the raffinate through a raffinate port.
  • SMB simulated moving bed chromatographic
  • the SMB apparatus comprises six columns positioned adjacent to each other and fluidly connected in series forming a closed loop configuration
  • the method comprises the steps of: simultaneously, feeding the mixture of step i) through a feed port into a simulated moving bed chromatographic (SMB) apparatus comprising six columns; feeding an eluent at a fifth column; withdrawing raffinate at a second column; and withdrawing extract at the fifth column.
  • SMB simulated moving bed chromatographic
  • the SMB apparatus comprises eight columns positioned adjacent to each other and fluidly connected in series forming a closed loop configuration
  • the method comprises the steps of: simultaneously, a) introducing a feed mixture from a feed tank into a column through a feed inlet; b) introducing an eluent from an eluent tank into a column, wherein the column is separated by four columns from the column of step a); c) withdrawing an extract from the column which is separated by six columns from the column of step a); wherein the extract comprises allulose; and d) withdrawing a raffinate from the column which is separated by one column from the column of step a); wherein the raffinate comprises one or more isomers of allulose.
  • Each of the four or more columns comprises a resin bed and a jacket surrounding the four or more columns, and wherein the resin bed enables separation of the sugar mixture.
  • Any resin that is suitable for separation of sugars can be used in the.
  • the resin is calcium-based resin.
  • resin include, but are not limited to, UBK 555 (Mitsubishi chemicals) and PCR642Ca++(Purolite)
  • UBK is from Mitsubishi Company and is a strongly acidic gel type on polystyrene divinylbenzene.
  • PCR642Ca++ is from Purolite Company and is gel type polystyrene cross-linked with divinylbenzene.
  • the feeding of the sugar mixture and the eluent into the four or more columns Cl to C8, and withdrawal of the extract and the raffinate from the four or more columns Cl to C8, are incremented in series towards adjacent columns, at a predetermined time intervals.
  • the method may comprise switching periodically the feed stream, raffinate, eluent, extract forward one column position at a time in the direction of the flow.
  • the switching time and liquid phase flow rates in each column are chosen properly to achieve a separation of the sugars. This switching is continued in a cyclic fashion and helps to efficiently separate the sugar streams utilizing a much smaller amount of resin.
  • the switching time is about 50-160 minutes.
  • the feed stream has a flow rate of about 10 cm/hr to about 50 cm/hr
  • the diluent/eluent has a flow rate of from about 60 cm/hr to about 80 cm/hr
  • the extract flow rate is from about 40 cm/hr to about 65 cm/hr
  • the raffinate flow rate is from about 40 cm/hr to about 60 cm/hr.
  • the SMB apparatus comprises eight columns positioned adjacent to each other and fluidly connected in series forming a closed loop configuration, and the method comprises one or more of the following cycles: cycle- 1: introducing feed into a first column Cl; introducing diluent into fifth column C5; withdrawing extract (D-allulose) from a seventh column C7; withdrawing raffinate (such as fructose) from the second column C2; cycle-2: introducing feed into a second column C2; introducing diluent into sixth column C6; withdrawing extract (D-allulose) from an eighth column C8; withdrawing raffinate (such as fructose) from the third column C3; cycle-3: introducing feed into a third column C3; introducing diluent into seventh column C7; withdrawing extract (D-allulose) from a first column Cl; withdrawing raffinate (such as fructose) from the fourth column C4; cycle-4: introducing feed into a fourth column C
  • the feed mixture (feed stream), and eluent are supplied from a suitable tank(s).
  • the method after a certain time, the method reaches a cyclic steady state (CSS).
  • the CSS is particularly reached after a certain number of cycles as depicted above, but the system state is still varying over the time because of the periodic movement of the inlet and outlet ports along the columns.
  • the extract and the raffinate are collected continuously. The extract and the raffinate are collected in an extract tank and a raffinate tank, respectively.
  • the method is carried out at a temperature of about 50-70 °C.
  • temperature of each column in the SMB is maintained by recirculating hot water into a jacket surrounding each column.
  • the feed stream, and the eluent are heated at a temperature of about 50-70 °C prior to introducing into the SMB apparatus.
  • the diluent is water. In some instances, the eluent is water.
  • the feed stream comprises allulose, and fructose.
  • the extract comprises allulose which is about 90-100% pure, and the raffinate comprises fructose which is about 70-100% pure.
  • the present disclosure provides a process for producing pure D-allulose from sugar source.
  • the process comprises: (i) mixing the sugar source with water or with an aqueous liquid and adjusting the concentration of dissolved sugar, such as sucrose thereby providing a first solution of sugar source;
  • step (i) water is added to sugar source such that the final concentration of sugar source, such as sucrose, is about 30% w/v to 60% w/v. In certain embodiments, the final concentration of sugar source is about 35% w/v or 40% w/v or 45% w/v or 50% w/v or 55% w/v or 60% w/v.
  • sugar source is ‘sucrose source’ and denotes any medium, solid, or liquid containing sucrose in different concentrations, in particular from about 1 to about 100% of sucrose.
  • the conversion of the sugar source to glucose and fructose can be done using conventional methods.
  • the sugar source is converted to glucose and fructose under heterogeneous or homogeneous catalysis which includes chemical and/or enzymatic catalysis.
  • the conversion of the sugar source to glucose and fructose according to step (ii) is performed using a strong cation exchange resin.
  • Suitable resins for a given conversion are known to a skilled person and commercially available. Examples of resins include, but are not limited to, PK216H (Mitsubishi chemicals), C124SH (Purolite; Indion) and 225H (Ion exchange).
  • the mixture of sugars is separated efficiently by using eight column SMB.
  • Suitable resins for separation are known to a skilled person and commercially available. Examples of resins include, but are not limited to, UBK 555 (Mitsubishi chemicals), PCR642Ca++(Purolite).
  • any suitable enzyme can be used in the process of step (iv).
  • the conversion according to step (iv) is performed under enzymatic catalysis by immobilized glucose isomarase enzyme.
  • the conversion of glucose to fructose is carried out at a temperature of about 50-55 °C, at a pH of about 8-9 and with a residence time of about 10-150 min.
  • the enzyme may be freely dissolved or immobilized on a solid carrier.
  • the enzyme may be present in dissolved state and may be retained in the reactor by membranes.
  • the enzyme may be immobilized on a solid support.
  • the enzyme may be present in microorganisms that in turn are retained in the reactor by membranes.
  • the enzyme may be present in microorganisms that in turn are immobilized on a solid support.
  • solid support materials include, but are not limited to, resins, plastics, and glass.
  • the enzyme may also be encapsulated by the solid support material, e.g., in form of alginate beads.
  • Step (v) can be performed using conventional methods.
  • fructose to allulose is done by enzymatic catalysisin the solution to allulose Any suitable enzyme can be used in the process.
  • the conversion according to step (v) is performed under enzymatic catalysis by immobilized D-tagatose 3-epimerase.
  • the conversion of fructose to allulose is carried out at a temperature of about 50-55 °C, at a pH of about 8-9 and with a residence time of about 10-50 min.
  • the enzyme may be freely dissolved or immobilized on a solid carrier.
  • the enzyme may be present in dissolved state and may be retained in the reactor by membranes.
  • the enzyme may be immobilized on a solid support.
  • the enzyme may be present in microorganisms that in turn are retained in the reactor by membranes.
  • the enzyme may be present in microorganisms that in turn are immobilized on a solid support.
  • solid support materials include, but are not limited to, resins, plastics, and glass.
  • the enzyme may also be encapsulated by the solid support material, e.g., in form of alginate beads.
  • step(iii) or fructose and allulose mixture in step(vi) are separated by simulated moving bed (SMB)
  • SMB simulated moving bed
  • the SMB is operated with conditions (in particular flow of feed and flow of solvent) that make it possible to obtain a highly pure allulose.
  • Typical arrangement of the simulated moving bed (SMB) chromatographic separation system and the SMB process are described above.
  • the fraction obtained from SMB comprises about 80% to about 100% allulose. In further embodiments, the fraction obtained comprises about 95% to about 100% allulose.
  • the fraction rich in allulose may be concentrated to provide a concentrated allulose.
  • the concentrated allulose may be purified further to get a pure allulose as syrup or solid.
  • the pure solid allulose can be obtained by precipitation, preferably by crystallization. Any suitable crystallization method known in the art can be employed.
  • the mixed bed comprises strong base anion exchange resin and weak acidic cation exchange resin.
  • Any suitable strong base anion exchange resin and weak acidic cation exchange resin can be used in the process.
  • the strong base anion exchange resin is SAF11AL-C1 (Mitsubishi chemicals) or C150SH (Purolite), and the weak acidic cation exchange resin WK40L (Mitsubishi chemicals) or A133S (Purolite).
  • the process depicted above is performed continuously and the purity of the allulose obtained is about 80% to about 100%. In further embodiments, the purity of the allulose is about 95% to about 100%.
  • the process has one or more of the following cycles:
  • Cycle -1 If the feed is pumped in column 1, then the diluent is added to column 5. The extract (honeytose or D-allulose) is collected from column 5. The raffinate (fructose) is withdrawn from column 2.
  • Cycle-2 If the feed is pumped in column 2, then the diluent is added to column 6. The extract (honeytose) is collected from column 6. The raffinate (fructose) is withdrawn from column 3.
  • Cycle-3 If the feed is pumped in column 3, then the diluent is added to column 1. The extract (honeytose) is collected from column 1. The raffinate (fructose) is withdrawn from column 4.
  • Cycle-4 If the feed is pumped in column 4, then the diluent is added to column 2. The extract (honeytose) is collected from column 2. The raffinate (fructose) is withdrawn from column 5.
  • Cycle-5 If the feed is pumped in column 5, then the diluent is added to column 3, the extract (honeytose) is collected from column 3 and the raffinate (fructose) is withdrawn from column 6.
  • Cycle-6 If the feed is pumped in column 6, then the diluent is added to column 4. The extract (honeytose) is collected from column 4. The raffinate (fructose) is withdrawn from column 1.
  • the entire SMB process is carried out at about 60 °C.
  • the temperature of the column is maintained by recirculation of hot water in the jacket.
  • the feed solution is heated through preheater in order to get desire temperature.
  • the diluent is heated through preheater in order to get desire temperature.
  • Each in line Brix meter is connected in the between the two columns. There are six such in line Brix meter is present in the SMB set up.
  • One pressure gauge is connected in between the column 6 and column 1. This pressure gauge should be placed in the recycle pump discharge side which is also connected in between column 1 and column 6.
  • Process parameters were as follows: Feed flow rate: 69.0 ml/min (22.82 cm/hr), Diluent Flow rate: 207.5 ml/min (68.64 cm/hr), Extract flow rate: 144.7 ml/min (47.86 cm/hr), Raffinate flow rate: 137.5 ml/min (45.48 cm/hr), Switching Time: 80 min, Extract purity: 97.3%, Raffinate Purity: 99.9%.
  • EXAMPLE 3 SEPARATION OF ALLULOSE-FRUCTOSE MIXTURE USING 8 COLUMN SMB 8 column SMB set up was used for separation of allulose-fmctose mixture in the following feed compositions by using water as an eluent.
  • Process parameters were as follows: Process temperature:60°Caverage; average feed flow rate: 72.0 ml/min, average diluent flow rate: 135.03 ml/min to 144 ml/min (40.3-43.0 cm/hr), average extract flow rate:59.86 ml/min to 61 ml/min, average raffinate flow rate: 147.1 ml/min to 150 ml/min, Switching Time: 80 -160 mins. The process has the following cycles.
  • cycle- 1 when feed is introduced into a first column Cl; diluent is introduced into fifth column C5; extract(D-allulose) is withdrawn from seventh column C7; raffinate (such as fructose) is withdrawn from the second column C2; cycle-2: when feed is introduced into a second column C2; diluent is introduced into sixth column C6; extract (D-allulose) is withdrawn from eighth column C8; raffinate (such as fructose) is withdrawn from the third column C3; cycle-3: when feed is introduced into a third column C3; diluent is introduced into seventh column C7; extract (D-allulose) is withdrawn from first column Cl; raffinate (such as fructose) is withdrawn from the fourth column C4; cycle-4: when feed is introduced into a fourth column C4; diluent is introduced into eighth column C8; extract (D-allulose) is withdrawn from second column C2; raffinate (such as fructos
  • Average Raffinate phase concentration (includes glucose): 28.94%;
  • EXAMPLE 4 SEPARATION OF ALLULOSE-FRUCTOSE MIXTURE USING 8 COLUMN SMB 8 column SMB was used for separation of allulose-fmctose mixture in the following feed compositions by using water as an eluent.
  • Average diluent flow rate 133.18 ml/min; Average raffinate flow rate: 147.03ml/min; and
  • Average Raffinate phase concentration (includes glucose): 29.12%;
  • Extract phase Concentration 13.96%
  • Average Raffinate purity 97.02%
  • the present disclosure relates to a method and a system that is simple, easy to operate and affordable.
  • the method and system according to the present disclosure is easy and inexpensive to manufacture.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Sustainable Development (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)

Abstract

La présente divulgation concerne un système et un procédé de purification de D-allulose et/ou de fructose à partir d'un mélange binaire.
PCT/IN2022/050452 2021-05-08 2022-05-08 Procédé et système de purification de d-allulose et/ou de fructose WO2022239027A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN202141007141 2021-05-08
IN202141007141 2021-05-08

Publications (1)

Publication Number Publication Date
WO2022239027A1 true WO2022239027A1 (fr) 2022-11-17

Family

ID=84029512

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2022/050452 WO2022239027A1 (fr) 2021-05-08 2022-05-08 Procédé et système de purification de d-allulose et/ou de fructose

Country Status (1)

Country Link
WO (1) WO2022239027A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102876817A (zh) * 2012-09-24 2013-01-16 厦门世达膜科技有限公司 一种分离果葡糖浆中的葡萄糖和阿洛酮糖的方法
US20200157131A1 (en) * 2017-06-30 2020-05-21 Samyang Corporation Method for producing sweetener allulose

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102876817A (zh) * 2012-09-24 2013-01-16 厦门世达膜科技有限公司 一种分离果葡糖浆中的葡萄糖和阿洛酮糖的方法
US20200157131A1 (en) * 2017-06-30 2020-05-21 Samyang Corporation Method for producing sweetener allulose

Similar Documents

Publication Publication Date Title
JP4371434B2 (ja) クロマトグラフ疑似移動床プロセスによる溶液分別方法
Kruschitz et al. Downstream processing technologies in the biocatalytic production of oligosaccharides
TW201835335A (zh) 用回收製造阿洛酮糖的方法
US8802843B2 (en) Tagatose production using simulated moving bed separation
CN110062762A (zh) 有效制备阿洛酮糖的方法
WO2019004579A1 (fr) Procédé de production d'édulcorant à base d'allulose
CN109721632B (zh) 一种高纯度神经节苷脂gm1及其制备方法
WO2022239027A1 (fr) Procédé et système de purification de d-allulose et/ou de fructose
Ching et al. An improved adsorption process for the production of high‐fructose syrup
CN110387391B (zh) 由葡萄糖生产果糖的方法
US11661635B2 (en) Fructose purification method
WO2022239028A1 (fr) Procédé et système de purification de d-allulose, de fructose et/ou de glucose
WO2008150298A1 (fr) Séparation de l'acide citrique de l'acide gluconique dans un bouillon de fermentation en utilisant un adsorbant à base de résine échangeuse d'ions anionique faiblement ou fortement basique
CN115073539B (zh) 一种2’-岩藻糖基乳糖分离纯化的方法
KR100508724B1 (ko) 트레할로오스및당알코올의제조방법
CN101066989A (zh) 四区模拟移动床分离纯化发酵液中谷胱甘肽的方法
US20180030077A1 (en) Process for preparing high-purity l-arabinose by using arabic gum as raw material
Jeon et al. L-Ribose from L-arabinose by epimerization and its purification by 3-zone simulated moving bed chromatography
Kochergin et al. Existing biorefinery operations that benefit from fractal-based process intensification
WO2022244018A1 (fr) Système et procédé pour augmenter la concentration en sucre dans une solution aqueuse de sucre
CN113209670B (zh) 顺序式模拟移动床耦合结晶过程的低聚木糖分离纯化系统及工艺
CN110305129B (zh) 三区带异步切换模拟移动床分离吴茱萸碱和吴茱萸次碱的方法
CN220468002U (zh) 一种高果糖去除杂糖的装置
EP3643786A2 (fr) Procédé de production de d-psicose à partir d'un complexe de d-psicose-borate à l'aide d'une chromatographie et composition contenant du d-psicose
CN110256197A (zh) 从由前体氢化获得的混合物中生产和分离甘露醇和山梨醇的方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 22806996

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 22806996

Country of ref document: EP

Kind code of ref document: A1