CN116444586A - Refining method of D-tagatose - Google Patents
Refining method of D-tagatose Download PDFInfo
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- CN116444586A CN116444586A CN202310437283.5A CN202310437283A CN116444586A CN 116444586 A CN116444586 A CN 116444586A CN 202310437283 A CN202310437283 A CN 202310437283A CN 116444586 A CN116444586 A CN 116444586A
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- tagatose
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- LKDRXBCSQODPBY-OEXCPVAWSA-N D-tagatose Chemical compound OCC1(O)OC[C@@H](O)[C@H](O)[C@@H]1O LKDRXBCSQODPBY-OEXCPVAWSA-N 0.000 title claims abstract description 69
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000007670 refining Methods 0.000 title claims abstract description 15
- 239000013078 crystal Substances 0.000 claims abstract description 71
- 238000002425 crystallisation Methods 0.000 claims abstract description 45
- 230000008025 crystallization Effects 0.000 claims abstract description 45
- 238000001816 cooling Methods 0.000 claims abstract description 37
- 239000007788 liquid Substances 0.000 claims description 39
- 238000003756 stirring Methods 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 239000011549 crystallization solution Substances 0.000 claims description 2
- 238000004042 decolorization Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 239000002245 particle Substances 0.000 abstract description 8
- 230000009286 beneficial effect Effects 0.000 abstract description 4
- 239000012452 mother liquor Substances 0.000 abstract description 2
- 238000011081 inoculation Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000009826 distribution Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- BJHIKXHVCXFQLS-PQLUHFTBSA-N keto-D-tagatose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-PQLUHFTBSA-N 0.000 description 2
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- IUKHSWVQCORLGA-UWOGQDNDSA-N (3s,4s,5r)-1,3,4,5,6-pentahydroxyhexan-2-one Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO.OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO IUKHSWVQCORLGA-UWOGQDNDSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 235000021474 generally recognized As safe (food) Nutrition 0.000 description 1
- 235000021473 generally recognized as safe (food ingredients) Nutrition 0.000 description 1
- 230000002641 glycemic effect Effects 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 235000013406 prebiotics Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a refining method of D-tagatose, which relates to the technical field of D-tagatose production, adopts a technical stage of combining gradient cooling crystallization and constant temperature crystallization, can obtain high-purity large-particle crystals, solves the problem that the products in the prior art are mostly powder-shaped, ensures that the large-particle D-tagatose product has wider application range and higher price advantage, and large-particle crystals are also beneficial to separating crystals from mother liquor, and the subsequent operation is simple.
Description
Technical Field
The invention relates to the technical field of D-tagatose production, in particular to a refining method of D-tagatose.
Background
D-Tagatose (D-Tagatose) is a hexose with molecular formula C 6 H 12 O 6 Is an epimer of fructose and is also an aldone isomer of galactose. It is a rare monosaccharide which naturally exists, and is mainly used in dairy products such as yogurt, milk powder, etc. The sweetness characteristics are similar to those of sucrose, and only one third of the calories are produced, so they are called low calorie sweeteners. Tagatose was formally approved by the United States Food and Drug Administration (USFDA) as a universally recognized safety food (GRAS) in 2001 and was approved by the european union for market in europe in 2005. Tagatose has important functions of low calorific value, zero glycemic index, blood sugar passivation effect, no decayed tooth, prebiotic effect, antioxidation activity and the like, and has been widely used in the fields of food, beverage, tooth care products and the like.
The current method for obtaining the D-tagatose crystal comprises an organic solvent method and the like, and the organic solvent crystallization adopts organic solvents such as ethanol, acetone and the like, and corresponding special equipment is required to be provided, so that the production cost is greatly increased, and the safe production is not facilitated. The commercial D-tagatose products mainly comprise liquid products and powdery solid products, the D-tagatose is used as a low-calorie sweetener, the powdery solid products are aggregated together when the addition amount is large, the rapid dissolution is difficult, and the application range of the product is limited.
Disclosure of Invention
The technical problems to be solved by the invention are as follows: aiming at the defects existing in the prior art, the refining method of the D-tagatose is provided, the production cost is low, the safety coefficient is high, and the granularity of the obtained D-tagatose crystal is large.
In order to solve the technical problems, the technical scheme of the invention is as follows:
a refining method of D-tagatose comprises the following steps:
a: adding the seed crystal into the D-tagatose liquid at 50-60 ℃ and uniformly stirring to ensure that the seed crystal is completely dispersed in the D-tagatose liquid;
b: the D-tagatose sugar solution added with the seed crystal is subjected to gradient cooling crystallization at the speed of 0.3-1.2 ℃/h, and a constant temperature is selected and stirred for 2-5 hours in four temperature intervals of 45-43 ℃, 40-38 ℃, 35-33 ℃ and 30-28 ℃ respectively until the temperature of the D-tagatose sugar solution reaches 25 ℃, and crystallization is stopped to obtain a crystallization solution;
c: the crystallization liquid is filtered by a 10um sand core funnel, the obtained crystal is washed by pure water at 4 ℃, and then dried under the conditions of the temperature of 45-55 ℃ and the vacuum degree of-0.07 to-0.09 MPa to obtain white D-tagatose crystal.
Preferably, the solid content of the D-tagatose liquid in the step A is more than or equal to 80% (W/W), and the purity is more than or equal to 95%.
Preferably, the seed crystals in step A have a particle size in the range of 50 to 100 mesh.
Preferably, the seed crystal in the step A is added in an amount of 0.1-1% of the solid matter in the D-tagatose liquid.
In the step A, the stirring speed is 100-150 rpm, and the stirring time is 30-60 s.
And (C) stirring at 30-80 rpm in the whole cooling process in the step (B).
And C, more than 80% of D-tagatose crystals obtained in the step C are 20-40 meshes.
In the step C, the purity of the D-tagatose crystal is more than or equal to 99 percent, and the crystallization yield is more than or equal to 80 percent.
And C, mixing the filtrate with the water washing liquid, decolorizing by using active carbon, wherein the dosage of the active carbon is 0.5-5% (W/V) of the volume of the mixed liquid, filtering by using 10um filter paper after decolorizing, concentrating to the solid content of more than or equal to 80% at the temperature of 40-70 ℃ under the vacuum of less than or equal to-0.09 MPa, and sleeving the concentrated solution in the D-tagatose sugar liquid in the step A.
Due to the adoption of the technical scheme, the invention has the beneficial effects that:
1. the invention adopts the technical stage of combining gradient cooling crystallization and constant temperature crystallization, can obtain high-purity large-particle crystals, solves the problem that the products in the prior art are mostly powder, ensures that the large-particle D-tagatose product has wider application range and higher price advantage, and the large-particle crystals are also beneficial to the separation of crystals and mother liquor, and the subsequent operation is simple.
2. The method avoids the crystallization mode of the organic solvent, has low requirements on equipment, simple process, low energy consumption, low preparation cost and convenient actual production, is particularly suitable for large-scale industrialized production and processing, has higher safety in production and operation without using the organic solvent, and has no recycling problem of the organic solvent, simple process and low cost.
3. In the invention, the gradient cooling is carried out at 0.3-1.2 ℃/h, and the low supersaturation degree of the sugar solution is maintained in the crystallization process, so that the formation probability of small crystal nuclei is reduced, and the growth of crystals is facilitated.
4. The low stirring speed of 30-80 rpm is adopted in the cooling crystallization process, so that the probability of crushing large crystals by the stirring paddles is reduced on one hand, and in addition, the low stirring speed is more beneficial to the growth of large-particle crystals.
5. In the invention, the functions of crystal growth and crystal adjustment are realized in each constant-temperature crystallization stage, so that the crystal size tends to be averaged, the crystal granularity is effectively increased, the generation of tiny crystals is inhibited, the finally obtained D-tagatose has larger crystal form and concentrated crystal size distribution.
6. The purity of the D-tagatose crystal obtained by the method is more than or equal to 99%, the crystallization yield is more than or equal to 80%, and the grain size distribution of more than 80% is 20-40 meshes.
Drawings
FIG. 1 is a diagram showing the crystal form of D-tagatose crystals under a 10-fold microscope in example 1 of the present invention;
FIG. 2 is a diagram showing the crystal form of D-tagatose crystals under a 10-fold microscope in example 2 of the present invention;
FIG. 3 is a diagram showing the crystal form of D-tagatose crystals under a 10-fold microscope in example 3 of the present invention.
Detailed Description
The invention is further illustrated by the following examples.
Example 1
1. D-tagatose seed crystal is added into the D-tagatose liquid, the volume of the D-tagatose liquid is 1L, the solid content is 84%, the purity is 97%, the temperature is 50 ℃, the mesh number of the added seed crystal is 50 meshes, the adding amount of the D-tagatose seed crystal is 4.2g, and after the seed crystal is added, the seed crystal is stirred for 50s at a stirring speed of 120rpm, so that the seed crystal is uniformly dispersed into a sugar liquid system, and an inoculation liquid is obtained.
2. Cooling the inoculation liquid to 44 ℃ at a cooling rate of 0.8 ℃/h, and keeping the constant temperature of 44 ℃ for crystallization for 2h;
then cooling to 39 ℃ at a cooling rate of 0.8 ℃/h, and keeping the constant temperature of 39 ℃ for crystallization for 2h;
then cooling to 34 ℃ at a cooling rate of 0.8 ℃/h, and keeping the constant temperature of 34 ℃ for crystallization for 2h;
then cooling to 29 ℃ at a cooling rate of 0.8 ℃/h, and keeping the constant temperature of 29 ℃ for crystallization for 2h;
finally, the temperature is reduced to 25 ℃ at the cooling rate of 0.8 ℃/h, the crystallization is stopped, and the crystallization liquid is obtained, and the stirring rotating speed is controlled to be 50rpm in the whole crystallization process.
3. The crystallization liquid is filtered by a 10um sand core funnel, then washed by pure water at 4 ℃, and dried in vacuum under the conditions of 50 ℃ and minus 0.09MPa to obtain 701g of D-tagatose crystal, the purity of the D-tagatose crystal is 99.6 percent, the crystallization yield is 83.5 percent, and 82 percent of crystal size is distributed between 20 and 40 meshes.
4. Mixing the filtrate in the step 3 with water washing liquid to obtain 0.37L, decolorizing with activated carbon, wherein the dosage of activated carbon is 3.7g, filtering to remove activated carbon by using 10um filter paper after decolorizing, concentrating at 40deg.C under vacuum degree-0.09 MPa until the solid content is more than or equal to 80% (W/W), adding 0.13L, and returning to the D-tagatose liquid in the step 1.
Example 2
1. D-tagatose seed crystal is added into the D-tagatose liquid, the volume of the D-tagatose liquid is 1L, the solid content is 80%, the purity is 97.3%, the temperature is 55 ℃, the mesh number of the added seed crystal is 80 meshes, the adding amount of the D-tagatose seed crystal is 8g, and after the seed crystal is added, the seed crystal is stirred for 30s at a stirring speed of 150rpm, so that the seed crystal is uniformly dispersed into a sugar liquid system, and an inoculation liquid is obtained.
2. Cooling the inoculation liquid to 45 ℃ at a cooling rate of 0.3 ℃/h, and keeping the constant temperature of 45 ℃ for crystallization for 3.5h;
then cooling to 40 ℃ at a cooling rate of 0.3 ℃/h, and keeping the constant temperature of 40 ℃ for crystallization for 3.5h;
then cooling to 35 ℃ at a cooling rate of 0.3 ℃/h, and keeping the constant temperature of 35 ℃ for crystallization for 3.5h;
then cooling to 30 ℃ at a cooling rate of 0.3 ℃/h, and keeping the constant temperature of 30 ℃ for crystallization for 3.5h;
and finally, cooling to 25 ℃ at a cooling rate of 0.3 ℃/h, stopping crystallization to obtain a crystallization liquid, and controlling the stirring rotating speed to be 30rpm in the whole crystallization process.
3. After crystallization, filtering by using a 10um sand core funnel, washing by using pure water at 4 ℃, and vacuum drying at 50 ℃ and minus 0.09MPa to obtain 688g of D-tagatose crystal, wherein the purity of the D-tagatose crystal is 99.7%, the crystallization yield is 83.2%, and the 83% crystal size distribution is 20-40 meshes.
4. Mixing the filtrate subjected to suction filtration in the step 3 with the water washing liquid to obtain 0.38L, decolorizing with activated carbon, wherein the dosage of the activated carbon is 8g, filtering with 10um filter paper after decolorizing, concentrating at 55 ℃ under the vacuum degree of-0.09 MPa until the solid content is more than or equal to 80%, adding 0.14L, and returning to the D-tagatose sugar solution in the step 1.
Example 3
1. D-tagatose seed crystal is added into the D-tagatose liquid, the volume of the D-tagatose liquid is 1L, the solid content is 90%, the purity is 97.7%, the temperature is 60 ℃, the mesh number of the added seed crystal is 100 meshes, the adding amount of the D-tagatose seed crystal is 0.9g, and after the seed crystal is added, the seed crystal is stirred for 60s at a stirring speed of 100rpm, so that the seed crystal is uniformly dispersed into a sugar liquid system, and an inoculation liquid is obtained.
2. Cooling the inoculation liquid to 43 ℃ at a cooling rate of 1.2 ℃/h, and keeping the temperature of 43 ℃ for 5h for constant-temperature crystallization;
then cooling to 38 ℃ at a cooling rate of 1.2 ℃/h, and keeping the constant temperature of 38 ℃ for crystallization for 5h;
then cooling to 33 ℃ at a cooling rate of 1.2 ℃/h, and keeping the constant temperature of 33 ℃ for crystallization for 5h;
then cooling to 28 ℃ at a cooling rate of 1.2 ℃/h, and keeping the constant temperature of 28 ℃ for crystallization for 5 hours;
and finally, cooling to 25 ℃ at a cooling rate of 1.2 ℃/h, stopping crystallization to obtain a crystallization liquid, and controlling the stirring rotating speed to be 80rpm in the whole crystallization process.
3. After crystallization, filtering by using a 10um sand core funnel, washing by using pure water at 4 ℃, and vacuum drying at 50 ℃ and minus 0.09MPa to obtain 742g of D-tagatose crystal, wherein the purity of the D-tagatose crystal is 99.9%, the crystallization yield is 84.1%, and the size distribution of 84% of crystals is 20-40 meshes.
4. Mixing the filtrate subjected to suction filtration in the step 3 with the water washing liquid to obtain 0.42L, decolorizing with active carbon, wherein the dosage of the active carbon is 21g, filtering with 10um filter paper after decolorizing, concentrating to solid content of more than or equal to 80% at 70 ℃ under the vacuum degree of-0.09 MPa, adding 0.15L, and returning to the D-tagatose sugar solution in the step 1.
It is to be understood that these examples are illustrative of the present invention and are not intended to limit the scope of the present invention. Further, it is understood that various changes and modifications may be made by those skilled in the art after reading the teachings of the present invention, and such equivalents are intended to fall within the scope of the claims appended hereto.
Claims (9)
1. The refining method of the D-tagatose is characterized by comprising the following steps of:
a: adding the seed crystal into the D-tagatose liquid at 50-60 ℃ and uniformly stirring to ensure that the seed crystal is completely dispersed in the D-tagatose liquid;
b: the D-tagatose sugar solution added with the seed crystal is subjected to gradient cooling crystallization at the speed of 0.3-1.2 ℃/h, and a constant temperature is selected and stirred for 2-5 hours in four temperature intervals of 45-43 ℃, 40-38 ℃, 35-33 ℃ and 30-28 ℃ respectively until the temperature of the D-tagatose sugar solution reaches 25 ℃, and crystallization is stopped to obtain a crystallization solution;
c: the crystallization liquid is filtered by a 10um sand core funnel, the obtained crystal is washed by pure water at 4 ℃, and then dried under the conditions of the temperature of 45-55 ℃ and the vacuum degree of-0.07 to-0.09 MPa to obtain white D-tagatose crystal.
2. The method for refining D-tagatose according to claim 1, wherein: in the step A, the solid content of the D-tagatose liquid is more than or equal to 80 percent (W/W), and the purity is more than or equal to 95 percent.
3. The method for refining D-tagatose according to claim 1, wherein: the grain size range of the seed crystal in the step A is 50-100 meshes.
4. The method for refining D-tagatose according to claim 1, wherein: the adding amount of the seed crystal in the step A is 0.1-1% of the solid mass in the D-tagatose liquid.
5. The method for refining D-tagatose according to claim 1, wherein: in the step A, the stirring speed is 100-150 rpm, and the stirring time is 30-60 s.
6. The method for refining D-tagatose according to claim 1, wherein: and (C) stirring at 30-80 rpm in the whole cooling process in the step (B).
7. The method for refining D-tagatose according to claim 1, wherein: and C, more than 80% of D-tagatose crystals obtained in the step C are 20-40 meshes.
8. The method for refining D-tagatose according to claim 1, wherein: in the step C, the purity of the D-tagatose crystal is more than or equal to 99 percent, and the crystallization yield is more than or equal to 80 percent.
9. The method for refining D-tagatose according to claim 1, wherein: mixing the filtrate in the step C with the water washing liquid, and decolorizing with active carbon, wherein the dosage of the active carbon is the volume of the mixed liquid
0.5-5% (W/V), filtering with 10um filter paper after decolorization, vacuum-reducing to-0.09 MPa at 40-70deg.C,
and (3) concentrating until the solid content is more than or equal to 80%, and then sleeving the concentrated solution in the D-tagatose liquid in the step (A).
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