DE102017218260A1 - Process for the specific separation of D-fructose from fruit juices or fruit juice concentrates - Google Patents

Abstract

The invention relates to a process for the separation of D-fructose from fruit juices or fruit juice concentrates by chromatography, a fructose-reduced extract, wherein the fructose-reduced extract is a fruit juice extract or fruit juice concentrate extract, and the use of the method for producing a fructose-reduced extract.

Description

The invention relates to a method for the specific separation of D-fructose from fruit juices or fruit juice concentrates by means of chromatography, a fructose-reduced extract, wherein the fructose-reduced extract is a fruit juice extract or a fruit juice concentrate extract, and the use of the method for producing a fructose-reduced extract ,

Due to the increasing demand in the food market, the pharmaceutical and cosmetic industry for valuable, natural ingredients, such as vitamins, colors, flavors, fatty acids and fruit acids, new, gentle processes for the isolation of natural ingredients are needed.

One of the aims is the development of methods for the specific separation of selected fruit ingredients such as sugars, especially fructose.

Known processes for the separation of fructose are membrane separation processes, electrodialysis, the use of boronic acids for the specific reduction of fructose and fermentative processes.

Membrane separation techniques include reverse osmosis (RO), dialysis, ultrafiltration (UF) and nanofiltration (NF). EP 0516769 B1 describes a two-stage membrane separation process for the selective removal of sugar from beverages, wherein in the first step macromolecules, colloidal turbidity and suspended particles of the raw material (eg fruit juice) are separated by micro- or ultrafiltration and then a concentration of mono- and disaccharides of the UF permeate a nanofiltration or reverse osmosis takes place, sugar-reduced permeate is obtained. Further describes EP 0589890 B1 a process optimization via a targeted pressure control on the retentate side. Further disclosed EP 0562100 B1 a three-stage membrane separation process for producing a low-sugar and a sugar-rich fruit juice product. Disadvantageously, by means of this membrane separation process, only an unspecific separation of sugars from the raw juice is carried out, whereby ingredients of similar molecular size, such as ascorbic acid and organic acids, are likewise removed. A further disadvantage is a high re-dilution of the products.
A special form of membrane separation processes is electrodialysis, in which a separation of ionogenic constituents from aqueous solutions by means of ion exchange membranes takes place with the application of an electrical potential difference (Strathmann and Chmiel, 1984). EP 0 458 389 B1 describes the separation of organic substances from a mixture containing a weak acid. Here, sugars are separated by their different tendency to bind to a weak acid. The weak acid is boric acid.

Fermentative processes for the degradation of sugar are traditionally used for the production of alcoholic beverages such as beer and wine, as well as in the production of kefir and kombucha, the differences in the yeast or bacterial culture used, the process control and in the pre- and post-treatment of fermenting product lie. EP0526460 A1 or. WO 9111920 A1 discloses the specific degradation of sucrose and D-glucose. Common after-treatment steps are the distillation to remove the ethanol formed, the neutralization of the lactic acid by calcium carbonate and the separation of the biomass by centrifugation or filtration.

One alternative is provided by chromatographic processes, where a great challenge is to identify suitable separation materials with sufficient selectivity.

The document McFeeters et al. discloses the use of reverse phase chromatography under aqueous conditions to separate sugars and organic acids, particularly fruit acids (McFeeters et al., 1984).

US 4193817 A discloses the decolorization of raw sugar solutions using heterodisperse ion exchangers, in particular a strong base anion exchanger comprising styrene / divinylbenzene (SDVB) with quaternary ammonium groups DE 10056193 A1 describes the sugar juice decolorization by means of monodisperse anion exchangers, whereby a higher capacity, a lower pressure loss, a higher mechanical and osmotic stability and sharper separation fronts are achieved. The application of the adsorbent resins is carried out in heatable columns, wherein the raw sugar solution is heated to temperatures in the range of 55 to 85 ° C and eluted with water. Sugar solutions can be decolorized by up to 92%.

Further describes EP 0609279 B1 the production of corn syrup (high-fructose corn syrup, HFCS) by means of adsorber resins, in particular ion exchange resins in the form of strong cation exchangers with sulfonic acid groups and calcium as the counterion.
The document US 2008/0044531 A1 or. WO 2006081530 A1 discloses the use of a synthetic cation exchange resin in the Ca ²⁺ -form based on polystyrene cross-linked with divinylbenzene with sulfonate groups to reduce sugars in fruit juices, in particular the example of fructose solutions and various juice concentrates. Disadvantageously describes US 2008/0044531 A1 no specific separation of D-fructose. Another disadvantage is metal ion-loaded ion exchangers, especially the Ca ²⁺ form, unstable in an application for fruit juices and thus regeneration steps needed.

The document EP 1348 037 B1 describes a weakly acidic cation exchanger, in particular a synthetic cation exchanger based on polyacrylic acid, crosslinked by divinylbenzene, for use in the separation of carbohydrates, in particular mono-, di- or oligosaccharides and sugar alcohols. The preferred use is disclosed at a pH in the range pH 2 to 4 or pH 5 to 10.

Disadvantageously, the state of the art does not describe a process for the specific separation of D-fructose from fruit juice or fruit juice concentrates.

Therefore, the object of the present invention is to provide a process for the specific separation of D-fructose from fruit juice or fruit juice concentrates.

It is another object of the invention to provide a natural D-fructose-reduced fruit extract.

1. a) Bereitstellen einer Lösung umfassend mindestens einen Fruchtsaft oder ein Fruchtsaftkonzentrat,
2. b) Bereitstellen eines Chromatographiesystems umfassend eine stationäre Phase und eine wässrige mobile Phase, wobei die stationäre Phase ein Ionenaustauscher mit Sulfonsäuregruppen in protonierter Form ist, wobei die wässrige mobile Phase einen pH-Wert im Bereich von pH 3 bis pH 7 aufweist,
3. c) Injektion der Lösung in das Chromatographiesystem, und
4. d) Elution mindestens einer D-Fructose reduzierten Fraktion.

According to the invention the object is achieved by a process for the separation of D-fructose from fruit juices or fruit juice concentrates by means of chromatography comprising the steps

1. a) providing a solution comprising at least one fruit juice or a fruit juice concentrate,
2. b) providing a chromatography system comprising a stationary phase and an aqueous mobile phase, the stationary phase being an ion exchanger having sulfonic acid groups in protonated form, the aqueous mobile phase having a pH in the range from pH 3 to pH 7,
3. c) injection of the solution into the chromatography system, and
4. d) Elution of at least one D-fructose reduced fraction.

Advantageously, the method according to the invention specifically reduces solutions comprising natural fruit juices or fruit juice concentrates by D-fructose, preferably by at least 50% (m / v) in relation to the fruit juice or fruit juice concentrate. With further advantage the process according to the invention is carried out under aqueous conditions and at low temperatures, preferably at a maximum of 35 ° C.

Further advantageously, the inventive method has a high productivity of the D-fructose reduced fraction, preferably a productivity of solids of at least 1.5 g / (min · l), more preferably a productivity of solids of at least 30 g / (min · l ).

According to the invention, the process is carried out with an order of steps a), b), c) and d) or b), a), c) and d).

Chromatography is understood to mean a process for the separation of mixtures of different compounds by the different distribution of the compounds between a stationary and a mobile phase. Preferably, the chromatography is liquid chromatography.

Fruit juice or fruit juice concentrate is understood to mean a fluid comprising at least one fruit whose fruit content is at least 100%.

In one embodiment of the method, the solution comprising at least one fruit juice or fruit juice concentrate is selected from apple juice, apple juice concentrate, orange juice, orange juice concentrate, lemon juice, lemon juice concentrate, sour cherry juice or sour cherry juice concentrate, preferably from apple juice, apple juice concentrate, orange juice or orange juice concentrate.

The solution comprising at least one fruit juice or a fruit juice concentrate preferably has 0.5 ° Brix to 50 ° Brix, preferably 25 ° Brix to 37.5 ° Brix. By "° Brix" is meant a unit of measurement for the relative density of a liquid. The determination of the relative density of a liquid is carried out with a refractometer.

The solution comprising at least one fruit juice or a fruit juice concentrate is particularly preferably an apple juice concentrate with 25 ° Brix.

A stationary phase is understood to mean an immobile solid or liquid substance on which a separation of mixtures of different compounds takes place by interactions in the chromatographic process. Preferably, the stationary phase is a solid substance in the form of a packed column.

According to the invention, the stationary phase is an ion exchanger with sulfonic acid groups in protonated form. An ion exchanger is understood as meaning a solid which can absorb ions from a solution and thereby emits an equivalent amount of ions.

Advantageously, the ion exchanger with sulfonic acid groups in protonated form is a strong cation exchanger. A cation exchanger is understood as meaning an ion exchanger which exchanges cations from a solution for other cations. It is furthermore advantageously achieved by means of the stationary phase, an ion exchanger having sulfonic acid groups in protonated form, a high specificity of the separation of D-fructose from fruit juice or fruit juice concentrates.

In one embodiment, the stationary phase is a polymer having covalently bonded polar functional groups, in particular sulfonic acid groups in protonated form.

In one embodiment, the stationary phase is a polystyrene, preferably a crosslinked polystyrene. Crosslinked polystyrenes advantageously have a high chemical stability. A crosslinked polystyrene is understood to mean a three-dimensionally crosslinked polystyrene-divinylbenzene copolymer prepared by copolymerization of styrene and divinylbenzene. The use of three-dimensionally crosslinked polystyrene-divinylbenzene copolymers as the stationary phase advantageously produces low prepressures.

In one embodiment, the stationary phase is a sulfonated polystyrene-divinylbenzene copolymer in protonated form.

The stationary phase is particularly preferably Nucleogel Sugar 810 H (Machery Nagel) or Purolite PCR 833 H (Purolite Ltd.).

In one embodiment, the stationary phase has a particle size in the range of 5 .mu.m to 350 .mu.m, preferably 5 .mu.m to 15 .mu.m. Particle size is understood to mean the average diameter of the stationary phase particles.

In one embodiment, the stationary phase has a column inner diameter in the range of 4 mm to 1.0 m, preferably 20 mm to 100 mm. Column internal diameter is understood to mean the diameter of a packed column of stationary phase.

In one embodiment, the stationary phase has a pore size in the range of 60 Å to 2000 Å, preferably 90 Å to 120 Å. By pore size is meant the average diameter of the pores of the stationary phase.

In one embodiment, the stationary phase has a porosity in the range of 0.2 to 0.4. By porosity is meant the ratio of the volume of the pores to the total volume of the stationary phase.

In a preferred embodiment, the stationary phase has a porosity in the range of 0.2 to 0.4 for stationary phases with a column inner diameter in the range of 8 mm to 20 mm. More preferably, the stationary phase has a porosity in the range of 0.23 to 0.24. By porosity is meant the ratio of the volume of the pores to the total volume of the stationary phase. The determination of the porosity can be calculated from the ratio of the volume of the mobile phase V _mobil and the column volume V _total or by means of the dead time t _{0 of} the column and the flow velocity v: $$\mathrm{\epsilon }=\frac{{\text{V}}_{\text{mobile}}}{{\text{V}}_{\text{total}}}=\frac{v\cdot {\text{t}}_{\text{0}}}{{\text{V}}_{\text{total}}},$$

The determination of the dead time t _{0 of} the column by means of a substance which does not penetrate into the pores of the stationary phase and does not interact, for. B. Dextran T 2000 with an average molecular weight of 1,950,000 g / mol.

According to the invention, the aqueous mobile phase has a pH in the range from pH 3 to pH 7, preferably in the range from pH 3.8 to pH 6, particularly preferably pH 6. Advantageously, the pH in the range of pH 3 to pH 7 shows a specific separation of D-fructose and D-sorbitol from the solution comprising at least one fruit juice or a fruit juice concentrate on the basis of the sequence of the elution in the chromatographic method.

A mobile phase is understood as meaning a mobile liquid or gaseous substance. Advantageously, the mobile phase dissolves and transports the mixture of compounds to be separated in the chromatographic process.

In a preferred embodiment, the aqueous mobile phase is water or an aqueous buffer solution, more preferably water.

In one embodiment of the method, the solution is injected into the chromatography system in step c) under concentration and / or volume overload of the chromatography column. Concentration overload is understood to mean an increase in the concentration of a sample at a constant injection volume. A volume overload is understood to mean an increase in the injection volume of a sample at a constant concentration. In a preferred embodiment of the preparative method, the solution is injected into the chromatography system in step c) with a concentration overload in the range of 0.5 ° Brix to 50 ° Brix, more preferably in the range of 10 ° Brix to 30 ° Brix.

According to the invention, the elution of at least one reduced D-fructose fraction in step d). A fraction is understood as part of a mixture of various compounds, in particular the solution comprising at least one fruit juice or a fruit juice concentrate. A reduction of D-fructose is understood to mean a reduced content of D-fructose relative to the solution comprising at least one fruit juice or a fruit juice concentrate.

Advantageously, the D-fructose reduced fraction further comprises a composition according to the composition of the solution comprising at least one fruit juice or a fruit juice concentrate.

Preferably, the D-fructose reduced fraction comprises glucose, sucrose, L-malic acid, citric acid and water. Preferably, the D-fructose reduced fraction comprises 90% to 100% (m / m) of the absolute content of glucose, sucrose, L-malic acid and citric acid of the solution comprising at least one fruit juice or a fruit juice concentrate.

In one embodiment, the D-fructose reduced fraction further comprises minerals and / or polyphenols.

In a preferred embodiment, the at least one D-fructose reduced fraction comprises a reduction of D-fructose by 50% to 98% (m / v) relative to the solution comprising at least one fruit juice or a fruit juice concentrate.

In one embodiment, the D-fructose reduced fraction has a D-fructose content of at most 5% (m / v), preferably at most 3% (m / v).

Preferably, the elution of at least one D-fructose reduced fraction in step d) comprises the union of the at least one fraction.

In one embodiment of the method, step c) and step d) are carried out continuously or discontinuously.

In one embodiment of the method, step d) is carried out by means of countercurrent chromatography, preferably by means of simulated moving bed chromatography. Simulated Moving Bed Chromatography (SMB Chromatography) is understood as a continuous, chromatographic process in which an opposite motion of solid stationary phase and liquid mobile phase is simulated. Advantageously, a separation takes place in several zones.

Advantageously, the SMB chromatography has a low consumption of the mobile phase. Preferably, by means of SMB chromatography, a consumption of the mobile phase of not more than 4 l / g, more preferably of not more than 0.4 l / g is achieved. Further advantageously, a higher purity is achieved by means of SMB chromatography.

In one embodiment of the method, step d) takes place with recycling of the mobile phase.

In one embodiment of the method, the at least one D-fructose reduced fraction in step d) D-sorbitol is reduced. A reduction of D-sorbitol is understood to mean a reduced content of D-sorbitol relative to the solution comprising at least one fruit juice or a fruit juice concentrate.

In a preferred embodiment of the process in the D-fructose reduced fraction in step d) D-sorbitol is reduced by 98% to 100% (m / v), based on the solution comprising at least one fruit juice or a fruit juice concentrate.

In one embodiment, the D-fructose reduced fraction has a maximum D-sorbitol content of 0.5% (m / v).

In one embodiment, the method comprises at least one further step, the further step being after the steps a), b), c) and step d), and an elution of at least one D-fructose-enriched fraction. An enrichment of D-fructose is understood to mean an increased content of D-fructose, based on the solution comprising at least one fruit juice or a fruit juice concentrate.

Advantageously, the process achieves a high recovery of D-fructose in the fraction enriched in at least one D-fructose, preferably a recovery of at least 90% (m / v) based on the solution comprising at least one fruit juice or a fruit juice concentrate, more preferably one Recovery of at least 95% (m / v) based on the solution comprising at least one fruit juice or a fruit juice concentrate.

Preferably, the fraction enriched in at least one D-fructose comprises 90% to 100% (m / m) of the absolute content of D-fructose of the solution comprising at least one fruit juice or a fruit juice concentrate.

In one embodiment of the method, the at least one D-fructose enriched fraction D-sorbitol is enriched. An enrichment of D-sorbitol is understood as meaning an increased content of D-sorbitol, based on the solution comprising at least one fruit juice or a fruit juice concentrate.

Preferably, the D-fructose enriched fraction comprises 90% to 100% (m / m) of the absolute D-sorbitol content of the solution comprising at least one fruit juice or fruit juice concentrate.

In one embodiment, the method comprises at least one further step, wherein the further step is selected from a concentration and / or purification, preferably a filtration and / or vacuum evaporation. The process preferably comprises concentration and / or purification of the fraction reduced in size of at least one D-fructose, particularly preferably filtration and / or vacuum evaporation of the fraction which is reduced in D-fructose.

The invention also provides a fructose-reduced extract comprising glucose, sucrose, L-malic acid, citric acid and water, wherein the fructose-reduced extract is a fruit juice extract or fruit juice concentrate extract, wherein the fructose-reduced extract has a D-fructose content of not more than 5% ( m / v).

An extract is understood as meaning an extract or a part of a mixture of various compounds from plants, in particular a fruit juice or a fruit juice concentrate.

Advantageously, the fructose-reduced extract is natural and / or has natural ingredients. Further advantageously, the fructose-reduced extract has no modifications or additions of compounds which have been prepared by biotechnological or chemical synthesis.

With further advantage, the fructose-reduced extract has a composition corresponding to the composition of the solution comprising at least one fruit juice or a fruit juice concentrate. Preferably, the fructose-reduced extract comprises 90% to 100% (m / m) of the absolute content of glucose, sucrose, L-malic acid and citric acid of the solution comprising at least one fruit juice or a fruit juice concentrate.

In one embodiment, the fructose-reduced extract comprises minerals and / or polyphenols.

In one embodiment, the fructose-reduced extract has a maximum D-sorbitol content of 0.5% (m / v).

In one embodiment, the fructose-reduced extract is an apple juice extract or an orange juice extract.

In a preferred embodiment, the fructose-reduced extract has a D-fructose content of not more than 3% (m / v).

Another aspect of the invention relates to the use of the method according to the invention for producing a fructose-reduced extract.

For the realization of the invention, it is also expedient to combine the above-described embodiments and features of the claims.

embodiments

The invention will be explained in more detail with reference to some embodiments and associated figures. The embodiments are intended to describe the invention without limiting it.

• 1 A eine Überlagerung von Chromatogrammen der Hauptinhaltsstoffe eines Fruchtsaftes an einem Ionenaustauscher mit Sulfonsäuregruppen in protonierter Form bei pH = 1,5 und
• 1 B eine Überlagerung von Chromatogrammen der Hauptinhaltsstoffe eines Fruchtsaftes an einem Ionenaustauscher mit Sulfonsäuregruppen in protonierter Form bei pH = 3,8.
• 2 ein Chromatogramm eines Apfelsaftes (Probenverdünnung 1:10, Fließgeschwindigkeit 0,4 mL/min, T = 25 °C, Eluent Wasser, RI-Detektor) an einem Ionenaustauscher mit Sulfonsäuregruppen in protonierter Form.

The show

• 1 A a superposition of chromatograms of the main ingredients of a fruit juice on an ion exchanger with sulfonic acid groups in protonated form at pH = 1.5 and
• 1 B a superposition of chromatograms of the main ingredients of a fruit juice on an ion exchanger with sulfonic acid groups in protonated form at pH = 3.8.
• 2 a chromatogram of an apple juice (sample dilution 1:10, flow rate 0.4 mL / min, T = 25 ° C, eluent water, RI detector) on an ion exchanger with sulfonic acid groups in protonated form.

1 A shows a chromatogram of the quantitatively occurring main constituents of a fruit juice on an ion exchanger with sulfonic acid groups in protonated form at pH = 1.5. The substances elute in the following order: sucrose, citric acid, D-glucose, D-fructose, L-malic acid and D-sorbitol. A specific separation of D-fructose or D-sorbitol from the fruit juice mixture would not be possible. By increasing the pH to between pH 3.8 and pH 6.0, the retention order is changed as follows: citric acid, sucrose, L-malic acid, D-glucose, D-fructose and D-sorbitol (see 1 B) , This effect only allows the use of a chromatographic method for the specific separation of D-fructose and D-sorbitol.

EMBODIMENT 1: Process for the separation of D-fructose from a solution comprising apple juice

D-fructose is separated from diluted 1.12 ° Brix apple juice, 11.2 ° Brix apple juice or 22.4 ° Brix apple juice concentrate (ASK) by simulated moving bed chromatography (SMB chromatography). with the SMB system CSEP C9116 (KNAUER Scientific Equipment GmbH) (parameters see Table 1) on an ion exchanger with sulfonic acid groups in protonated form, wherein a purity (P r), a yield (Rec), a productivity (Pr), an eluent consumption ( EC) and a product dilution (Verd) according to Table 2 was achieved. Table 1: Parameters for SMB chromatography with the four volumetric flows V̇ _{1, SMB} , V̇ _{2, SMB} , V̇ _{3, SMB} , V̇ _{4, SMB} , the switching time t _s and the sample volume flow (Feed) V̇ _Feed . sample V̇ _{1, SMB} V̇ _{2, SMB} V̇ _{3, SMB} V̇ _{4, SMB} t _s V̇ _Feed (ML / min) (ML / min) (ML / min) (ML / min) (Min) (ML / min) diluted apple juice (1,12) 1.61 1.49 1.57 1.43 21.2 0.08 Apple juice (11,20) 1.61 1.49 1.57 1.43 21.2 0.08 ASK (22,40) 1.61 1.48 1.53 1.43 22.2 0.03 Table 2: Purity (Pur), Yield (Rec), Productivity (Pr), Eluent Consumption (EC) and Product Dilution (Verd) relative to the raw material at various raw material concentrations (n = 3 ± s) (D-Fructose Enriched Fraction - FaF, D-fructose reduced fraction - FrF). Raw material (° Brix) product Pure (%) Rec (%) Pr (g / (min · L)) EC (L / g) Verd diluted FaF 100 ± 1.3 104 ± 2.4 2.3 2.6 2.0 Apple juice (1,12) FrF 97 ± 1.0 95 ± 1.8 1.5 3.7 2.3 Apple juice (11,20) FaF 98 ± 1.0 103 ± 1.6 22.3 0.3 2.0 FrF 96 ± 0.9 94 ± 1.8 15.3 0.4 2.4 ASK (22,40) FaF 99 ± 0.9 102 ± 2.0 43.5 0.1 1.8 FrF 97 ± 0.8 95 ± 1.7 30.9 0.2 2.4

2 shows the chromatogram of the diluted apple juice with the main constituents occurring quantitatively on an ion exchanger with sulfonic acid groups in protonated form at pH = 6 and the fractionation of the eluted samples in the D-fructose reduced fraction and D-fructose enriched fraction. The substances elute in the following order: sucrose, L-malic acid, D-glucose, D-fructose and D-sorbitol.

Using apple juice concentrate (ASK), the productivity of the process can be doubled (15.3 g / (min.L) to 30.9 g / (min.L)) compared to apple juice. Eluent consumption decreases by 50% from 0.4 L / g to 0.2 L / g. The process can be operated more efficiently by using higher concentrations of raw materials. Therefore, the use of ASK is suitable for the production of a fructose-reduced extract.

The first eluted fraction, the fructose-reduced extract, has a content of D-fructose of 1 g / L. Thus, in the D-fructose reduced fraction, D-fructose is reduced by 98% (m / v) relative to apple juice.

The contents of D-glucose at 31.3 g / L and L-malic acid at 2.1 g / L are in the concentration range of the apple juice.

In an alternative embodiment of the embodiment, the concentration of the fructose-reduced extract takes place.

Embodiment 2: A method for separating D-fructose from a solution comprising orange juice

The separation of D-fructose is carried out starting from orange juice with 11.2 ° Brix by means of SMB chromatography with the SMB system CSEP C9116 (KNAUER Scientific Equipment GmbH) on an ion exchanger with sulfonic acid groups in protonated form, wherein a purity (PUR), a Yield (Rec), productivity (Pr), eluent consumption (EC) and product dilution (Verd) according to Table 3 were achieved. Table 3: Purity (Pur), Yield (Rec), Productivity (Pr), Eluent Consumption (EC) and Product Dilution (Verd) relative to the raw material (n = 3 ± s) (D-Fructose Enriched Fraction - FaF, D-Fructose reduced fraction - FrF). Raw material (° Brix) product Pure (%) Rec (%) Pr (g / (min · L)) EC (L / g) Verd Orange juice (11,20) FaF 98 ± 1.0 106 ± 3.0 10 0.5 1.6 FrF 98 ± 0.8 96 ± 2.7 26 0.2 2.3

Quoted non-patent literature

Strathmann H, Chmiel H (1984) Electrodialysis - a membrane method with many applications. Chemical engineer technology. 56: 214-220 ,

LIST OF REFERENCE NUMBERS

1

sucrose

2

citric acid

3

glucose

4

D-fructose

5

L-malic acid

6

D-sorbitol

7

at least one D-fructose reduced fraction

8th

at least one D-fructose enriched fraction

QUOTES INCLUDE IN THE DESCRIPTION

This list of the documents listed by the applicant has been generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

Cited patent literature

• EP 0516769 B1 [0005]
• EP 0589890 B1 [0005]
• EP 0562100 B1 [0005]
• EP 0458389 B1 [0005]
• EP 0526460 A1 [0006]
• WO 9/111920 A1 [0006]
• US 4193817 A [0009]
• DE 10056193 A1 [0009]
• EP 0609279 B1 [0010]
• US 2008/0044531 A1 [0010]
• WO 2006081530 A1 [0010]
• EP 1348037 B1 [0011]

Cited non-patent literature

• Strathmann H, Chmiel H (1984) Electrodialysis - a membrane method with many applications. Chemical engineer technology. 56: 214-220 [0081]

Claims (15)

Process for the separation of D-fructose from fruit juices or fruit juice concentrates by means of chromatography comprising the steps a) providing a solution comprising at least one fruit juice or a fruit juice concentrate, b) providing a chromatography system comprising a stationary phase and an aqueous mobile phase, the stationary phase being an ion exchanger having sulfonic acid groups in protonated form, the aqueous mobile phase having a pH in the range from pH 3 to pH 7, c) injection of the solution into the chromatography system, and d) Elution of at least one D-fructose reduced fraction. Method according to Claim 1 , characterized in that the stationary phase is a sulfonated polystyrene-divinylbenzene copolymer in protonated form. Method according to Claim 1 or 2 , characterized in that the stationary phase has a porosity in the range of 0.2 to 0.4. Method according to one of Claims 1 to 3 , characterized in that the aqueous mobile phase is water or an aqueous buffer solution. Method according to one of Claims 1 to 4 , characterized in that the at least one fraction reduced D-fructose has a reduction of D-fructose by 50% to 98% (m / v) based on the solution comprising at least one fruit juice or a fruit juice concentrate. Method according to one of Claims 1 to 5 , characterized in that step c) and d) are carried out continuously or discontinuously. Method according to one of Claims 1 to 6 , characterized in that step d) by means of countercurrent chromatography, preferably by means of simulated moving bed chromatography, is performed. Method according to one of Claims 1 to 7 , characterized in that the at least one D-fructose reduced fraction in step d) D-sorbitol is reduced. Method according to Claim 8 , characterized in that the at least one reduced D-fructose fraction has a reduction of D-sorbitol by 98% to 100% (m / v) based on the solution comprising at least one fruit juice or a fruit juice concentrate. Method according to one of Claims 1 to 9 , characterized in that the method comprises at least one further step, wherein the further step after the steps a), b), c) and step d) takes place and is an elution of at least one D-fructose enriched fraction. Method according to one of Claims 1 to 10 , characterized in that the method comprises at least one further step, wherein the further step is selected from a concentration and / or purification. A fructose-reduced extract comprising glucose, sucrose, L-malic acid, citric acid and water, wherein the fructose-reduced extract is a fruit juice extract or fruit juice concentrate extract, wherein the fructose-reduced extract has a maximum D-fructose content of 5% (m / v). Fructose-reduced extract after Claim 12 comprising minerals and / or polyphenols. Fructose-reduced extract after Claim 12 or 13 , characterized in that the fructose-reduced extract has a maximum D-sorbitol content of 0.5% (m / v). Use of a method according to one of Claims 1 to 11 for producing a fructose-reduced extract.

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