# US 10,246,476 B2 · Method for preparing D-psicose crystal

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- Number: US 10,246,476 B2
- Document ID: US10246476B2
- Status: Granted
- Kind: B2
- Application number: 15/520,786
- Filed: 2015-08-09
- Published: 2017-11-02
- Granted: 2019-04-02
- Earliest claimed: 2014-10-20
- Assignees: Cj Cheiljedang Corporation
- Applicants: Cj Cheiljedang Corporation
- Inventors: Seong Bo Kim; Seung Won Park; Jun Gap An; Joo Hang Lee
- Web page: https://patentgrep.com/patent/US10246476B2

## CPC

- C07H 1/06: Separation; Purification
- B01D 9/0013: {by indirect heat exchange}
- B01D 9/0036: {Crystallisation on to a bed of product crystals; Seeding}
- B01D 15/185: {characterised by the components to be separated}
- B01D 15/363: {Anion-exchange}
- C07H 3/02: Monosaccharides
- A23L 27/33: {containing sugars or derivatives}
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

A method for producing high purity D-psicose crystals having a purity of 98% (w/w) or more and a grain size of MA200 or more. The method includes: removing impurities from a D-psicose solution to obtain a purified D-psicose solution; concentrating the purified D-psicose solution; cooling the concentrated D-psicose solution to 30° C. to 40° C. through a heat exchanger; seed crystallizing the D-psicose solution at 30° C. to 40° C. to obtain a seed crystallized massecuite; and full-scale crystallizing the seed crystallized massecuite. The method can produce pure D-psicose crystals in a suitable form for industrial application through an economical crystallization process from the D-psicose solution without using organic solvents.

## Claims

### Claim 1

A method for producing D-psicose crystals having a grain size of MA200 μm or larger, comprising:
removing impurities from a D-psicose solution to obtain a purified D-psicose solution;
concentrating the purified D-psicose solution to provide a concentrated D-psicose solution having a concentration of 80 Brix (%) to 85 Brix (%);
performing rapid cooling of the concentrated D-psicose solution to 30° C. to 40° C. in a heat exchanger to provide a copied D-psicose solution having a temperature between 3° C. and 4° C., wherein the rapid cooling is performed at a cooling rate of 5° C. to 20° C. per hour;
placing the cooled D-psicose solution at a temperature between 30° C. and 40° C. to a crystallizer and adding D-psicose seed crystals to the crystallizer;
performing seeded crystallization of D-psicose in the crystallizer while controlling temperature to stay between 30° C. and 40° C., which provides a D-psicose massecuite having a temperature between 30° C. and 40° C.; and
performing full-scale crystallization of D-psicose using the D-psicose massecuite while controlling temperature to stay between 30° C. and 40° C., which provides D-psicose crystals having a grain size of MA200 μm or larger.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the step of removing impurities from a D-psicose solution to obtain a purified D-psicose solution comprises:
decoloring the D-psicose solution by passing through a column packed with a decoloring agent;
desalting the decolored D-psicose solution via ion exchange resin chromatography; and
passing the desalted D-psicose solution through a continuous chromatography column packed with an ion exchange resin to which calcium activating groups are attached.

### Claim 3 (depends on 2)

The method according to claim 2, wherein the ion exchange resin used in the ion exchange resin chromatography is a 100% weak basic anion resin.

### Claim 4 (depends on 2)

The method according to claim 2, wherein the step of passing through a continuous chromatography column is a simulated moving bed (SMB) process.

### Claim 5 (depends on 2)

The method according to claim 2, wherein the D-psicose solution purified through the continuous chromatography column has a purity of 95% (w/w) or more.

### Claim 6 (depends on 1)

The method for producing high purity D-psicose crystals according to claim 1, wherein performing seeded crystallization comprises
adding seeds of D-psicose to the cooled D-psicose solution at a temperature between 30° C. and 40° C.; and
adding additional D-psicose solutions to the seeds-added D-psicose solution.

### Claim 7 (depends on 6)

The method according to claim 6, wherein the concentration of the additional D-psicose solutions is in a range of 80 Brix (%) to 85 Brix (%).

### Claim 8 (depends on 6)

The method according to claim 6, wherein the volume of the additional D-psicose solutions is in a range of 5 (v/v) % to 20 (v/v) % based on the volume of the seed-added D-psicose solution.

### Claim 9 (depends on 1)

The method according to claim 1, wherein the full-scale crystallization comprises:
adding another D-psicose solution having a purity of 95% (w/w) or higher and a concentration of 80 Brix (%) to 85 Brix (%) to the seed crystallized massecuite, and
subsequently, repeating heating and cooling the resulting solution within the range of 30° C. to 40° C.

### Claim 10 (depends on 9)

The method according to claim 9, wherein repeating heating and cooling the resulting solution comprises adding, to the resulting solution, an additional D-psicose solution at a temperature of 30° C. to 40° C. two times or more an interval of 10 hours to 20 hours.

### Claim 11 (depends on 10)

The method according to claim 10, wherein the additional D-psicose solution is added each time in an amount of 5 (v/v) % to 20 (v/v) % based on the volume of the resulting solution to which the additional D-psicose solution is added.

### Claim 12

A method of crystallizing D-psicose, the method comprising:
concentrating a D-psicose solution to provide a concentrated D-psicose solution having a concentration of 80 Brix (%) to 85 Brix (%);
performing rapid cooling of the concentrated D-psicose solution to 30° C. to 40° C. to provide a cooled D-psicose solution having a temperature between 30° C. and 40° C., wherein the rapid cooling is performed by heat exchange at a cooling rate of 5° C. to 20° C. per hour;
placing, in a first crystallizer, the cooled D-psicose solution having a temperature between 30° C. and 40° C. and adding D-psicose crystal seeds to the first crystallizer;
performing seeded crystallization of D-psicose in the first crystallizer while controlling a temperature of the D-psicose solution in the first crystallizer to stay between 30° C. and 40° C., which provides a D-psicose massecuite;
placing the D-psicose massecuite to a second crystallizer and adding thereto a processed D-psicose solution to provide a crystallization mixture in the second crystallizer, wherein the processed D-psicose has a concentration between 80 Brix (%) and 85 Brix (%) and a temperature between 30° C. and 40°; and
performing crystallization of D-psicose in the second crystallizer while controlling a temperature of the crystallization mixture in the crystallizer to stay between 30° C. and 40° C., which provides D-psicose crystals having a grain size of MA200 μm or larger.

### Claim 13 (depends on 12)

The method of claim 12, wherein performing seeded crystallization in the first crystallizer comprises adding an additional D-psicose solution to the first crystallizer at least once, wherein the additional D-psicose solution is at a temperature between 30° C. and 40° C. when added.

### Claim 14 (depends on 12)

The method of claim 12, wherein performing crystallization in the second crystallizer comprises adding an additional D-psicose solution to the second crystallizer at least once, wherein the additional D-psicose solution is at a temperature between 30° C. and 40° C. when added.