CN111349123A - Sialic acid refining method for improving product quality through ethanol-ethyl acetate - Google Patents
Sialic acid refining method for improving product quality through ethanol-ethyl acetate Download PDFInfo
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- CN111349123A CN111349123A CN201811559842.5A CN201811559842A CN111349123A CN 111349123 A CN111349123 A CN 111349123A CN 201811559842 A CN201811559842 A CN 201811559842A CN 111349123 A CN111349123 A CN 111349123A
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- sialic acid
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- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 title claims abstract description 77
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 title claims abstract description 77
- 238000000034 method Methods 0.000 title claims abstract description 29
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000007670 refining Methods 0.000 title claims abstract description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000000047 product Substances 0.000 claims abstract description 30
- 239000011259 mixed solution Substances 0.000 claims abstract description 28
- 239000012535 impurity Substances 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000002156 mixing Methods 0.000 claims abstract description 16
- 239000012043 crude product Substances 0.000 claims abstract description 13
- 238000001035 drying Methods 0.000 claims abstract description 13
- 239000008367 deionised water Substances 0.000 claims abstract description 11
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 11
- 239000007787 solid Substances 0.000 claims abstract description 9
- 238000002425 crystallisation Methods 0.000 claims abstract description 8
- 230000008025 crystallization Effects 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 239000012071 phase Substances 0.000 claims description 12
- 238000009777 vacuum freeze-drying Methods 0.000 claims description 8
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 238000010981 drying operation Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 244000000626 Daucus carota Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000005770 birds nest Nutrition 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000035790 physiological processes and functions Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000005765 wild carrot Nutrition 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 241000510654 Bupleurum chinense Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 244000061508 Eriobotrya japonica Species 0.000 description 1
- 235000009008 Eriobotrya japonica Nutrition 0.000 description 1
- 102000018697 Membrane Proteins Human genes 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 210000004102 animal cell Anatomy 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- -1 carbohydrate compound Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000000369 enteropathogenic effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 235000020256 human milk Nutrition 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- BQINXKOTJQCISL-GRCPKETISA-N keto-neuraminic acid Chemical compound OC(=O)C(=O)C[C@H](O)[C@@H](N)[C@@H](O)[C@H](O)[C@H](O)CO BQINXKOTJQCISL-GRCPKETISA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- CERZMXAJYMMUDR-UHFFFAOYSA-N neuraminic acid Natural products NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO CERZMXAJYMMUDR-UHFFFAOYSA-N 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
- C07H7/033—Uronic acids
-
- 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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- 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)
Abstract
The invention discloses a sialic acid refining method for improving product quality by ethanol-ethyl acetate, which comprises the following steps: step 1: dissolving the sialic acid crude product in deionized water at 28-35 ℃, and filtering to remove insoluble impurities to obtain a water phase; step 2: taking a proper amount of ethanol and ethyl acetate, mixing the ethanol and the ethyl acetate according to the ratio of 1: 1.12-1: 1.2 in unequal amounts, and mixing the water phase and the ethanol-ethyl acetate mixed solution to obtain a mixed solution; and step 3: and (3) fully stirring the mixed solution in a crystallization tank, standing, centrifuging at 7000-8000 r/min to obtain sialic acid solid, and drying sialic acid to obtain a refined sialic acid product. The sialic acid refining method for improving the product quality by ethanol-ethyl acetate adopts ethanol-ethyl acetate to refine sialic acid; the impurity can be extracted from sialic acid into the mixed solution of ethanol-ethyl acetate to remove the impurity, which is beneficial to improving the production efficiency and the production quality of the product.
Description
Technical Field
The invention relates to the technical field of sialic acid refining, in particular to a sialic acid refining method for improving product quality through ethanol-ethyl acetate.
Background
Sialic acid is a natural carbohydrate compound widely existing in biological systems, plays an indispensable role in a plurality of important biological and physiological processes of a living body, is also called sialic acid (PSA), is a main component with biological activity in the edible bird's nest of the traditional rare food in China, provides immunity for the early growth of infants by sialic acid in breast milk, improves the absorption capacity of vitamin and mineral substances in intestinal tracts, is neuraminic acid, widely exists in animal tissues and microorganisms, is an important component of cell membrane protein, participates in a plurality of physiological functions on the cell surface, plays a very important role in regulating the physiological and biochemical functions of human bodies, is systematically studied internationally in recent years, and scientists have found that sialic acid has a plurality of important biological functions because sialic acid is not degraded by enzymes in digestive systems, can enter the intestinal tract through the digestive tract to prevent the absorption of enteropathogenic bacteria, viruses and cells, and plays an important role in resisting various pathogenic bacteria;
the preparation method of sialic acid mainly comprises a chemical synthesis method, an enzymatic synthesis method, a natural product extraction method, a microbial fermentation method and the like, wherein sialic acid is widely existed on the surface of animal cells in the form of glycoconjugates, so that the sialic acid can be extracted and produced, the natural product extraction method is to extract sialic acid from natural resources with relatively rich sialic acid content and apply the sialic acid to production, for example, the sialic acid content in the bird's nest is about 67g/kg, and casein, poultry eggs, loquat, bupleurum chinense and eggplant also contain different sialic acid contents;
the existing common method for purifying sialic acid is a glacial acetic acid method, the sialic acid yield is low, but impurity removal is incomplete, the use amount of an organic solvent is too large, the drying time of a refined glacial acetic acid product is long (about 96 hours), the process is long in time consumption, and the refined product obtained by crystallization and purification still has impurities with small polarity after a main peak through liquid phase detection; therefore, we have proposed a method for refining sialic acid by improving the quality of the product by ethanol-ethyl acetate, so as to solve the problems proposed above.
Disclosure of Invention
The invention aims to provide a sialic acid refining method for improving the product quality by ethanol-ethyl acetate, which aims to solve the problems that the prior common method for purifying sialic acid proposed by the background technology is a glacial acetic acid method, the sialic acid yield is low, but the impurity removal is incomplete, the use amount of an organic solvent is overlarge, the drying time of a glacial acetic acid refined product is long (about 96 hours), the process is long in time consumption, and the liquid phase detection shows that impurities with small polarity exist after a main peak of a refined product obtained by crystallization purification.
In order to achieve the purpose, the invention provides the following technical scheme: a sialic acid refining process for improving product quality by ethanol-ethyl acetate, the refining process comprising the steps of:
step 1: dissolving the sialic acid crude product in deionized water at 28-35 ℃, and filtering to remove insoluble impurities to obtain a water phase;
step 2: taking a proper amount of ethanol and ethyl acetate, mixing the ethanol and the ethyl acetate according to the ratio of 1: 1.12-1: 1.2 in unequal amounts, and mixing the water phase and the ethanol-ethyl acetate mixed solution to obtain a mixed solution;
and step 3: and (3) fully stirring the mixed solution in a crystallization tank, standing, centrifuging at 7000-8000 r/min to obtain sialic acid solid, and drying sialic acid to obtain a refined sialic acid product.
Preferably, in the step 1, the mass-to-volume ratio of the crude sialic acid product to the deionized water is 1g: 3-1 g:5 mL.
Preferably, the mass-to-volume ratio of the aqueous phase to the ethanol-ethyl acetate mixture in the step 2 is preferably 1g: 25-50 mL.
Preferably, the drying operation in step 3 is vacuum freeze drying.
Preferably, the vacuum freeze drying operation conditions obtained in the step 3 are that the temperature is-60-30 ℃, the vacuum degree is-0.095 MPa, and the drying time is 48-72 h.
Compared with the prior art, the invention has the beneficial effects that: the sialic acid refining method for improving the product quality by ethanol-ethyl acetate adopts ethanol-ethyl acetate to refine sialic acid; by utilizing the principle that sialic acid is not dissolved in the ethanol-ethyl acetate mixed solution and impurities have certain solubility in the mixed solution, the impurities are extracted from the sialic acid into the ethanol-ethyl acetate mixed solution to remove the impurities, so that the production efficiency and the production quality of the product are improved;
in addition, the method can not only completely remove impurities with smaller polarity after the main peak, but also well remove other impurities in the product, thereby obviously improving the liquid phase purity and the content of effective components of the product and ensuring that the purity of the refined product reaches more than 98 percent and is far higher than the current average purity of 0.1 percent. The vacuum freeze-drying method is selected in the drying treatment step, the treatment capacity is greatly enhanced, the yield is improved to 1 ton per day, the yield is improved, the sugar decomposition loss is reduced, and the like.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a technical scheme that: a sialic acid refining method for improving product quality by ethanol-ethyl acetate comprises the following steps:
step 1: dissolving the sialic acid crude product in deionized water at 28-35 ℃, and filtering to remove insoluble impurities to obtain a water phase;
step 2: taking a proper amount of ethanol and ethyl acetate, mixing the ethanol and the ethyl acetate according to the ratio of 1: 1.12-1: 1.2 in unequal amounts, and mixing the water phase and the ethanol-ethyl acetate mixed solution to obtain a mixed solution;
and step 3: and (3) fully stirring the mixed solution in a crystallization tank, standing, centrifuging at 7000-8000 r/min to obtain sialic acid solid, and drying sialic acid to obtain a refined sialic acid product.
In the step 1 in this embodiment, the mass-to-volume ratio of the sialic acid crude product to the deionized water is 1g: 3-1 g:5mL, the sialic acid crude product after freeze drying is favorable for ensuring chemical stability and avoiding excessive activity, and insoluble impurities are conveniently removed by mixing the sialic acid crude product with the deionized water, so as to facilitate post-processing.
In this example, the mass-to-volume ratio of the aqueous phase to the ethanol-ethyl acetate mixture in step 2 is preferably 1g: 25-50 mL, through mixing of sialic acid and ethanol-ethyl acetate, sialic acid is convenient to be dissolved in an ethanol-ethyl acetate mixed solution, and impurities are extracted from sialic acid to the ethanol-ethyl acetate mixed solution to remove the impurities on the principle that the impurities have certain solubility in the mixed solution, so that the purity and quality of a produced product are guaranteed.
In the embodiment, the drying operation in the step 3 is vacuum freeze drying, and meanwhile, the vacuum freeze drying operation conditions obtained in the step 3 are that the temperature is-60-30 ℃, the vacuum degree is-0.095 MPa, and the drying time is 48-72 hours, and the sialic acid solid obtained after stirring and standing is convenient for vacuum drying, sugar decomposition loss and the like are reduced, so that the processing capacity is enhanced, and the sialic acid refining efficiency is improved.
Example 1:
preparing sialic acid from 500g of sialic acid crude product;
mixing 500g of sialic acid crude product with 2000ml of deionized water, and filtering to remove insoluble impurities after fully mixing to obtain a water phase;
mixing the water phase with a mixed solution of ethanol and ethyl acetate which is pre-installed in a ratio of 1:1.15 for mixing, wherein the mass volume ratio of the water phase to the mixed solution of ethanol and ethyl acetate is 1g: 30mL, thereby obtaining a mixed solution;
and fully stirring the mixed solution in a crystallization tank, standing, centrifuging at 7000-8000 r/min to obtain sialic acid solid, and drying the sialic acid solid for 54 hours at the temperature of-25 ℃ and the vacuum degree of-0.095 MPa to obtain 435g of refined sialic acid product with the yield of 87% and the purity: 98.5 percent and less than 0.1 percent of single impurity.
Example 2:
20000g of sialic acid crude product is taken for preparation of sialic acid;
20000g of sialic acid crude product is mixed with 100000ml of deionized water, and after the sialic acid crude product and the deionized water are fully mixed, insoluble impurities are removed through filtration to obtain a water phase;
mixing the water phase with a mixed solution of ethanol and ethyl acetate which is pre-installed in a ratio of 1:1.2 for mixing, wherein the mass volume ratio of the water phase to the mixed solution of ethanol and ethyl acetate is 1g: 35mL, thereby obtaining a mixed solution;
and fully stirring the mixed solution in a crystallization tank, standing, centrifuging at 7000-8000 r/min to obtain sialic acid solid, and drying the sialic acid solid for 72 hours at the temperature of 5 ℃ and the vacuum degree of-0.095 MPa to obtain 17300g of refined sialic acid product with the yield of 86.5 percent and the purity: 98.3 percent and less than 0.1 percent of single impurity.
In conclusion, the method can completely remove impurities with small polarity after the main peak, can well remove other impurities in the product, and obviously improves the liquid phase purity and the content of effective components of the product, so that the purity of the refined product reaches more than 98 percent and is far higher than the current average purity of 0.1 percent. The vacuum freeze-drying method is selected in the drying treatment step, the treatment capacity is greatly enhanced, the yield is improved to 1 ton per day, the yield is improved, the sugar decomposition loss is reduced, and the like.
Although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that various changes in the embodiments and/or modifications of the invention can be made, and equivalents and modifications of some features of the invention can be made without departing from the spirit and scope of the invention.
Claims (5)
1. A sialic acid refining method for improving product quality by ethanol-ethyl acetate is characterized in that: the refining method comprises the following steps:
step 1: dissolving the sialic acid crude product in deionized water at 28-35 ℃, and filtering to remove insoluble impurities to obtain a water phase;
step 2: taking a proper amount of ethanol and ethyl acetate, mixing the ethanol and the ethyl acetate according to the ratio of 1: 1.12-1: 1.2 in unequal amounts, and mixing the water phase and the ethanol-ethyl acetate mixed solution to obtain a mixed solution;
and step 3: and (3) fully stirring the mixed solution in a crystallization tank, standing, centrifuging at 7000-8000 r/min to obtain sialic acid solid, and drying sialic acid to obtain a refined sialic acid product.
2. The method of claim 1, wherein the step of refining sialic acid comprises the steps of: in the step 1, the mass-to-volume ratio of the sialic acid crude product to the deionized water is 1g: 3-1 g:5 mL.
3. The method of claim 1, wherein the step of refining sialic acid comprises the steps of: the mass-to-volume ratio of the aqueous phase to the ethanol-ethyl acetate mixed solution in the step 2 is preferably 1g: 25-50 mL.
4. The method of claim 1, wherein the step of refining sialic acid comprises the steps of: the drying operation in the step 3 is vacuum freeze drying.
5. The method of claim 4, wherein the step of refining sialic acid comprises the steps of: the vacuum freeze drying operation conditions obtained in the step 3 are that the temperature is-60-30 ℃, the vacuum degree is-0.095 MPa, and the drying time is 48-72 hours.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811559842.5A CN111349123A (en) | 2018-12-20 | 2018-12-20 | Sialic acid refining method for improving product quality through ethanol-ethyl acetate |
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| CN201811559842.5A CN111349123A (en) | 2018-12-20 | 2018-12-20 | Sialic acid refining method for improving product quality through ethanol-ethyl acetate |
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| CN111349123A true CN111349123A (en) | 2020-06-30 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102532208A (en) * | 2012-01-06 | 2012-07-04 | 南京工业大学 | Method for continuously separating sialic acid |
| CN106883274A (en) * | 2015-12-15 | 2017-06-23 | 中科鸿基生物科技有限公司 | Sialic acid process for purification |
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2018
- 2018-12-20 CN CN201811559842.5A patent/CN111349123A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102532208A (en) * | 2012-01-06 | 2012-07-04 | 南京工业大学 | Method for continuously separating sialic acid |
| CN106883274A (en) * | 2015-12-15 | 2017-06-23 | 中科鸿基生物科技有限公司 | Sialic acid process for purification |
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