CN112961201A - Crystallization method of spherical sucralose - Google Patents
Crystallization method of spherical sucralose Download PDFInfo
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- CN112961201A CN112961201A CN202110332128.8A CN202110332128A CN112961201A CN 112961201 A CN112961201 A CN 112961201A CN 202110332128 A CN202110332128 A CN 202110332128A CN 112961201 A CN112961201 A CN 112961201A
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- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 title claims abstract description 89
- 235000019408 sucralose Nutrition 0.000 title claims abstract description 87
- 239000004376 Sucralose Substances 0.000 title claims abstract description 86
- 238000002425 crystallisation Methods 0.000 title claims abstract description 31
- 239000013078 crystal Substances 0.000 claims abstract description 73
- 238000000034 method Methods 0.000 claims abstract description 32
- 230000008025 crystallization Effects 0.000 claims abstract description 28
- 238000001816 cooling Methods 0.000 claims abstract description 18
- 238000001914 filtration Methods 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 238000002604 ultrasonography Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 230000010355 oscillation Effects 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 3
- 238000009210 therapy by ultrasound Methods 0.000 claims description 3
- 238000003825 pressing Methods 0.000 claims description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000000967 suction filtration Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 11
- 230000003068 static effect Effects 0.000 abstract description 5
- 239000000428 dust Substances 0.000 abstract description 4
- 230000005611 electricity Effects 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- 238000010899 nucleation Methods 0.000 description 4
- 230000006911 nucleation Effects 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 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 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008123 high-intensity sweetener Substances 0.000 description 2
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000007440 spherical crystallization Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
-
- 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
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- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for crystallizing spherical sucralose, which comprises the steps of crystallizing and separating the sucralose. Firstly, cooling crystallization is carried out in solution, and an ultrasonic field with certain frequency and power is added during cooling crystallization to carry out auxiliary crystallization. And filtering and separating the sucralose crystals after the crystallization is finished. The preparation method improves the crystal shape of the sucralose crystals, and obtains transparent sucralose spherical crystals. The obtained spherical crystal of the sucralose has good flowing property and mechanical property, is not easy to generate dust and static electricity and is not easy to agglomerate, thereby achieving the purpose of improving the downstream production efficiency.
Description
Technical Field
The invention relates to a novel method for crystallizing spherical sucralose crystals, which prepares the spherical sucralose crystals through solution crystallization and achieves the purpose of improving the downstream production efficiency.
Background
Sucralose, known collectively as 4, 1 ', 6' -trichloro-41 ', 6' -trideoxygalactosucrose, known by the english name sucralose, abbreviated as TGS, and having the molecular formulaC12H19O8Cl3, molar molecular weight 397.64 g mol-1. Sucralose is a high-intensity sweetener, which takes sucrose as a raw material, is the only sweetener with a structure similar to that of sucrose at present, and has wide application in food and beverage. Sucralose is a pure white crystal, and is not easy to absorb moisture. It is soluble in water, ethanol and methanol and has little effect on the pH of the solution. Sucralose is often sold as needle crystals, which is the final purification of the post-synthesis product, or as a "micronized" product produced in the form of milled crystals. However, in order for high intensity sweeteners to be conveniently used for dry blending and tableting, several criteria should be met. This includes good flow properties, little dust formation during processing, no static problems, and good mechanical strength. However, the needle-shaped crystals after the purification of the product have poor fluidity and generate static electricity during the processing. The grinding of the crystals to micronize the product is prone to dust formation and to agglomeration due to the increased surface area, which should be avoided in the subsequent production.
World patent WO 2008144063a1 reports a new method of sucralose crystallization. The method comprises the steps of dissolving sucralose, dripping the sucralose into liquid nitrogen to be instantly solidified, and removing the solvent by adopting a freeze-drying method to obtain spherical crystals. However, the sucralose crystal obtained has poor mechanical properties due to excessive channels in the crystal, and is easy to absorb water vapor in the air. In addition, this method cannot be applied industrially on a large scale.
A new method of sucralose crystallization is also reported in european patent EP 1863358B 1. Adding a certain amount of seed crystals into a sucralose solution, and then drying and crystallizing in a fluidized bed at 50 ℃ at a certain flow rate to obtain the spherical aggregate of sucralose. The aggregate is spherical, so that the aggregate has good flowing property, and experiments show that the aggregate is not easy to absorb moisture and has good mechanical property. However, because the method uses the fluidized bed for drying at a lower temperature, the method has the disadvantages of higher energy consumption and higher cost. Therefore, it is necessary to find a new method for the spherical crystallization of sucralose.
Disclosure of Invention
The invention aims to provide a novel method for crystallizing spherical sucralose crystals, which can prepare the spherical sucralose crystals more efficiently, and the sucralose crystals obtained by the method have the advantages of low cost, good fluidity and difficult moisture absorption, so that the downstream production efficiency is improved.
In order to achieve the purpose, the invention adopts the following technical scheme:
the crystallization method of the spherical sucralose specifically comprises the following steps:
dissolving sucralose in a crystallizer according to a preset proportion in a solvent, then adding seed crystals, cooling to room temperature under the action of ultrasonic waves, and then crystallizing at constant temperature for 0.5-1.5 h to obtain a crystallization liquid containing spherical sucralose crystals;
filtering the crystallization liquid to obtain spherical crystal of the sucralose
Further, the crystallizer comprises a batch kettle type crystallizer, a continuous kettle type crystallizer, a batch oscillation baffle plate crystallizer or a continuous oscillation baffle plate crystallizer.
Furthermore, the frequency of the ultrasonic wave is 20 kHz-500 kHz, and the power is 1W-1000W.
Further, the time of ultrasonic treatment is 1-1000 min.
Further, the solvent comprises water, methanol, ethanol, ethyl acetate or sec-butyl acetate.
Further, the preset proportion is as follows: the mass ratio of the sucralose to the solvent is 0.1: 1-3: 1.
further, the preset proportion is as follows: the mass ratio of the sucralose to the solvent is 0.5: 1-2: 1.
further, the proportion of seed crystal is 0.001% -10%.
Further, the cooling rate of the cooling crystallization is 0.01-0.5 ℃/min.
Further, the filtering method is filter pressing or suction filtration.
The invention has the advantages that:
the invention provides a novel method for preparing spherical sucralose crystals, which comprises the steps of cooling and crystallizing in a solution, and adding an ultrasonic field with certain frequency and power for auxiliary crystallization during cooling and crystallizing to obtain the spherical sucralose crystals. The product has the advantages of good fluidity, difficult moisture absorption, good mechanical property, difficult dust generation, difficult static generation and the like, so that the production efficiency of a downstream production line is better improved, and the product is more beneficial to further processing and utilizing the downstream production line. At the same time, since the crystallization process is operated in solution, the cost is significantly reduced relative to other prior patents. Furthermore, due to the addition of ultrasound, the time required for crystallization is greatly reduced relative to the previous one, about 20% of the time required for the original process.
Drawings
FIG. 1 is a microscope photograph of sucralose crystals obtained in comparative example 1;
FIG. 2 is a microscope photograph of sucralose crystals obtained in comparative example 2;
FIG. 3 is a microscope photograph of sucralose crystals obtained in example 1;
FIG. 4 is a graph comparing the nucleation rates upon crystallization of comparative example 1 and example 1;
FIG. 5 is a graph comparing the growth rates when comparative example 1 and example 1 were crystallized;
FIG. 6 is a microscope photograph of sucralose crystals obtained in example 2.
Detailed Description
In order to make the present invention more comprehensible, the technical solutions of the present invention are further described below with reference to specific embodiments, but the present invention is not limited thereto.
Comparative example 1
48g of sucralose and 60g of water were added to a three-necked flask, and the mixture was stirred and heated to 55 ℃ to be completely dissolved. Slowly cooling to 50 deg.C, adding 5% sucralose seed crystal, growing crystal for 60min at a rate of 0.1 deg.C/min-1The cooling rate is 200rpm, and the temperature is reduced and the crystal is crystallized. When the temperature is reduced to room temperature, the mixture is continuously stirred and crystallized for 60min at constant temperature. Subjecting the obtained crystal liquid toSuction filtration gave the crystals as shown in FIG. 1. The sucralose crystal recovery rate was 11.24%.
Comparative example 2
48g of sucralose and 60g of water were added to a three-necked flask, and the mixture was stirred and heated to 55 ℃ to be completely dissolved. Slowly cooling to 50 deg.C, adding 5% sucralose seed crystal, growing crystal for 60min at a rate of 0.1 deg.C/min-1The cooling rate is 200rpm, and the temperature is reduced and the crystal is crystallized. When the temperature is reduced to room temperature, the crystallization kettle is placed in an ultrasonic field for crystallization, wherein the ultrasonic frequency is 22.6kHz, the power is 10W, and the ultrasonic time is 60 min. The obtained crystal liquid was suction-filtered to obtain crystals as shown in FIG. 2. The sucralose crystal recovery rate was 25.64%.
Example 1
48g of sucralose and 60g of water are added into a three-neck flask, and the mixture is heated to 55 ℃ by ultrasonic-assisted stirring to be completely dissolved. Slowly cooling to 50 deg.C, adding 5% sucralose seed crystal, growing crystal for 60min at a rate of 0.1 deg.C/min-1The temperature reduction rate of (2) is that the temperature reduction crystallization is carried out in an ultrasonic field with the ultrasonic power of 22.6kHz and the power of 10W. When the temperature is reduced to room temperature, the constant temperature crystallization is continued for 60min, and crystals as shown in FIG. 3 are obtained. The crystal recovery of sucralose was 68.52%.
From the microscope images of the sucralose crystals obtained in the above examples, it can be seen that the sucralose crystals obtained by the present invention are subjected to auxiliary sucralose crystallization by means of ultrasound, and the obtained sucralose crystals are spherical, and the length and diameter of the crystals are smaller than those of the existing products, so that the sucralose crystals have the advantages of good fluidity, less moisture absorption, good mechanical properties, less dusting, less static electricity generation, etc., so that the production efficiency of the downstream production line is better improved, and the sucralose crystals are more beneficial for further processing and utilization of the downstream production line.
The growth rates of crystal faces of the sucralose (101) and the sucralose (110) are higher than those of the crystal faces of the sucralose (011) and the sucralose (002), and the shearing force of the crystal faces of the sucralose is smaller under the stirring condition, so that the sucralose crystals cannot be broken and abraded well, and the crystal habit of the sucralose crystals is needle-shaped at the moment. And the introduction of the ultrasound after cooling crystallization enables a large amount of cavitation bubbles to be generated due to the cavitation effect of the ultrasound in the system, the collapse of the cavitation bubbles can generate a large amount of micro-jets, and the micro-jets impact the crystal of the sucralose to break and wear the crystal of the sucralose, so that the crystal habit of the sucralose approaches to a spherical shape. In the auxiliary crystallization by introducing ultrasound in the cooling crystallization process, the ultrasound can change the growth rate of each crystal face in the crystal, and the microjet generated by the ultrasound can better make the concentration in the system more uniform, so that the growth rate of each crystal face of sucralose in the system is changed, wherein the rates of (101) and (110) are reduced, and the growth rates of (011) and (002) are increased; meanwhile, the ultrasound has the abrasion and crushing functions, and the crystal habit of the sucralose crystals is changed from needle-shaped crystals which are not subjected to the ultrasound treatment into spherical crystals due to the synergistic effect of the two factors.
The nucleation rate and the crystallization rate of comparative example 1 and example 1 were compared at the time of crystallization, and the comparison is shown in fig. 4 and fig. 5. As can be seen from the figure, under the action of the ultrasonic field, the nucleation rate of the sucralose is increased by geometric times relative to that of the sucralose without the ultrasonic field, and the growth rate of the sucralose is also grown to a certain extent, which explains the reason that the sucralose is crystallized at a higher speed under the ultrasonic condition. Therefore, in the ultrasonic field, the crystallization speed of the sucralose can be greatly improved, the time required for crystallization is reduced, the aim of reducing the operation cost is fulfilled, and the production efficiency is improved.
Example 2
An aqueous solution of sucralose was prepared according to the ratio of example 1, and heated to 55 ℃ to completely dissolve it. Pumping the material into a continuous oscillation flow crystallizer by using a peristaltic pump, reducing the temperature to room temperature at a cooling rate of 0.3 ℃/min, and preserving the temperature for 0.5h in oscillation flow. An ultrasonic field is added outside the oscillating flow crystallizer to promote the nucleation and growth of the oscillating flow crystallizer. The residence time of the feed solution in the oscillating flow crystallizer for this process is about 2 h. The sucralose crystals obtained are shown in FIG. 6, and the recovery rate of the sucralose crystals is 65.13%.
In summary, the above-mentioned embodiments are only preferred embodiments of the present invention, and all equivalent changes and modifications made in accordance with the claims of the present invention should be covered by the present invention.
Claims (10)
1. A method for crystallizing spherical sucralose, characterized by: the method comprises the following steps: dissolving sucralose in a solvent in a crystallizer, then adding seed crystals, cooling to room temperature under the action of ultrasound, then crystallizing at constant temperature for 0.5-1.5 h to obtain a crystallization liquid containing spherical sucralose crystals, and filtering to obtain the spherical sucralose crystals.
2. The method of crystallizing sucralose spherical shape of claim 1, wherein: the crystallizer comprises an intermittent kettle type crystallizer, a continuous kettle type crystallizer, an intermittent oscillation baffle plate crystallizer or a continuous oscillation baffle plate crystallizer.
3. The method of crystallizing sucralose spherical shape of claim 1, wherein: the frequency of the ultrasonic wave is 20 kHz-500 kHz, and the power is 1W-1000W.
4. The method of claim 3, wherein the method comprises the steps of: the ultrasonic treatment time is 1-1000 min.
5. The method of crystallizing sucralose spherical shape of claim 1, wherein: the solvent comprises water, methanol, ethanol, ethyl acetate or sec-butyl acetate.
6. The method of crystallizing sucralose spherical shape of claim 1, wherein: the mass ratio of the sucralose to the solvent is 0.1: 1-3: 1.
7. the method of claim 6, wherein the method comprises the steps of: the mass ratio of the sucralose to the solvent is 0.5: 1-2: 1.
8. the method of crystallizing sucralose spherical shape of claim 1, wherein: the seed crystal is added in a proportion of 0.001% -10%.
9. The method of crystallizing sucralose spherical shape of claim 1, wherein: the cooling rate of the cooling crystallization is 0.01-0.5 ℃/min.
10. The method of crystallizing sucralose spherical shape of claim 1, wherein: the filtering method is filter pressing or suction filtration.
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Cited By (2)
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CN111808999A (en) * | 2020-07-23 | 2020-10-23 | 广东省生物工程研究所(广州甘蔗糖业研究所) | Sucrose seed crystal and preparation method thereof |
CN115433245A (en) * | 2022-09-13 | 2022-12-06 | 天津大学 | Crystallization method for improving flowability of sucralose |
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