CN111718272B - Preparation method and application of alanine metal chelate - Google Patents
Preparation method and application of alanine metal chelate Download PDFInfo
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- CN111718272B CN111718272B CN202010673644.2A CN202010673644A CN111718272B CN 111718272 B CN111718272 B CN 111718272B CN 202010673644 A CN202010673644 A CN 202010673644A CN 111718272 B CN111718272 B CN 111718272B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/142—Amino acids; Derivatives thereof
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/20—Inorganic substances, e.g. oligoelements
- A23K20/24—Compounds of alkaline earth metals, e.g. magnesium
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/20—Inorganic substances, e.g. oligoelements
- A23K20/30—Oligoelements
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic System without C-Metal linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
- C07F1/08—Copper compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic System
- C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic System compounds without a metal-carbon linkage
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic System without C-Metal linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
- C07F3/02—Magnesium compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
- C07F3/06—Zinc compounds
Abstract
The invention relates to a preparation method of an alanine metal chelate, which comprises the following steps: adding a metal salt solution into an alanine solution, performing chelation reaction under an acidic condition, concentrating the obtained reaction solution, precipitating, separating and drying to obtain the product. The method has the advantages of high chelation rate, simple and convenient operation, obviously shortened production period and obviously reduced production cost, and is suitable for large-scale industrial production.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a preparation method and application of an alanine metal chelate.
Background
Essential trace elements (such as iron, copper, manganese, zinc, etc.) play a very important role in animal nutrition. The conventional feed has low and incomplete trace element content, is difficult to meet the requirements of livestock and poultry, and needs to be manually added. For over half a century, a great deal of research has been conducted on trace element additives. The amino acid metal chelate is a novel microelement feed additive developed in recent years, and is known as a third-generation product. The amino acid metal chelate is the reaction product of metal ions and amino acids, and methionine, tyrosine, tryptophan, leucine, glycine, hydrolyzed protein and the like are often used as ligands. The chemical stability of the metal amino acid chelate is far higher than that of inorganic compounds or complexes due to the cyclic structure of the chelate. The amino acid metal chelate has the effects of resisting interference, relieving antagonism competition between minerals, and the like. The chelate has neutral intramolecular charge, good solubility under the condition of the environment in the organism, easy release of metal ions, direct digestion and absorption by intestinal tracts, and improved utilization rate and bioavailability of trace elements.
The amino acid metal chelate is prepared by mixing and chelating metal salt and amino acid. But the problems of low yield, low utilization rate of amino acid and metal salt, increased production cost, resource waste and the like generally exist.
Disclosure of Invention
The invention aims to provide a preparation method of an alanine metal chelate, which comprises the following steps: adding a metal salt solution into an alanine solution, and performing chelation reaction under an acidic condition to obtain the alanine metal chelate, wherein the obtained reaction solution is preferably concentrated, separated and dried to obtain the alanine metal chelate.
In a preferred embodiment of the present invention, the metal salt is selected from any one of zinc salt, calcium salt, magnesium salt, iron salt, copper salt, and chromium salt, preferably any one of zinc chloride, calcium chloride, magnesium chloride, ferric chloride, cupric chloride, chromium chloride, zinc nitrate, calcium nitrate, magnesium nitrate, ferric nitrate, cupric nitrate, chromium nitrate, zinc sulfate, calcium sulfate, magnesium sulfate, ferric sulfate, cupric sulfate, and chromium sulfate, or a combination thereof.
In a preferred embodiment of the present invention, the alanine is selected from any one of L-alanine, D-alanine, alpha-alanine, beta-alanine, DL-alanine, or a combination thereof.
In a preferred embodiment of the invention, alanine is present in the chelation reaction: the molar ratio of the metal salts is 1:1 to 4:1, preferably 2:1 to 3:1.
In a preferred embodiment of the invention, the reaction solution undergoes a chelation reaction at a pH of 4 to 6.5, preferably a pH of 5 to 6.0.
In a preferred embodiment of the present invention, the acid-base regulator for regulating the pH of the reaction solution is selected from any one of sodium hydroxide, potassium hydroxide, sodium bicarbonate, sodium carbonate, or a combination thereof.
According to the preferred technical scheme of the invention, the chelating reaction temperature is 70-100 ℃, preferably 80-90 ℃.
In a preferred embodiment of the invention, the chelation reaction is carried out with stirring and simultaneously with ultrasonic treatment.
In a preferred embodiment of the present invention, the ultrasonic power is 60-120W, more preferably 80-100W.
In a preferred technical scheme of the invention, the ultrasonic time is 1-6h, preferably 2.0-4h.
In a preferred embodiment of the present invention, the number of times of ultrasound is 1 to 6, preferably 3 to 4.
In a preferred embodiment of the present invention, the concentration is selected from any one of vacuum concentration, membrane concentration, normal pressure concentration, ultrafiltration concentration, and centrifugal concentration, or a combination thereof.
In a preferred embodiment of the present invention, the separation is selected from any one of crystallization, filtration, centrifugation, membrane treatment, or a combination thereof.
In a preferred embodiment of the present invention, the collected isolated solid is washed and dried, preferably the solvent used for washing is water.
In a preferred embodiment of the present invention, the drying is selected from any one of vacuum drying, reduced pressure drying, normal pressure drying, spray drying, and boiling drying, or a combination thereof.
According to the preferred technical scheme, the prepared alanine chelated metal salt is subjected to crystallization and purification treatment, and the frequency of crystallization and purification treatment is preferably not less than 1 time, and preferably 2-4 times.
In a preferred embodiment of the present invention, the crystallization purification solvent is selected from any one of ethanol, propanol, methanol, butanol, acetone, isopropanol, isobutanol, ethyl acetate, or a combination thereof.
It is a further object of the present invention to provide the use of an alanine metal chelate for the preparation of an animal feed.
In a preferred embodiment of the present invention, the animal feed is selected from any one of chicken feed, duck feed, goose feed, pig feed, cow feed, horse feed, donkey feed, cat feed, dog feed, fish feed, rabbit feed, sheep feed.
In the preferred technical scheme of the invention, the feed is prepared by adding 0.05% -1% of alanine chelated metal salt into animal feed base ration, and the addition amount of the alanine chelated metal salt in the animal feed base ration is preferably 0.1% -0.8%, and more preferably 0.2% -0.5%.
In the preferred technical scheme, the basic ration is selected from any one of chicken basic ration, duck basic ration, goose basic ration, pig basic ration, cow basic ration, horse basic ration, donkey basic ration, cat basic ration, dog basic ration, fish basic ration, rabbit basic ration and sheep basic ration.
In a preferred technical scheme of the invention, the alanine metal chelate is one or more selected from alanine zinc chelate, alanine calcium chelate, alanine iron chelate, alanine copper chelate, alanine magnesium chelate and alanine chromium chelate.
Unless otherwise indicated, the detection method of the invention adopts EDTA (disodium ethylenediamine tetraacetate) standard titration method to determine the chelation rate in a sample, and comprises the following specific steps:
1. the inorganic metal ions in the sample were extracted with methanol and the supernatant and precipitate were centrifuged.
2. 1g of precipitate was weighed, extracted with 25ml of absolute methanol, filtered, 0.1ml of filtrate was taken and 3ml of dithizone chloroform solution was added, and the sample was bluish green (dithizone color) and no red color was observed. If a red color appears, it is indicated that free metal ions are present in the chelate.
3. Titration of metal ions in the supernatant with EDTA solution, recording the volume of EDTA solution consumed by the titration as V 1 . After ashing the sample, titrating the total metal element in the sample by using EDTA solution, and recording the volume of the EDTA solution consumed by titration as V 2 。
4. The chelation rate of the sample is calculated as follows:
wherein: concentration of C-Standard EDTA (mol/L)
V 1 Titration of the volume (ml) of EDTA solution consumed by the free metallic element
V 2 -volume of EDTA solution (ml) consumed by titration of total amount of metallic elements
Unless otherwise indicated, when the invention relates to a percentage between liquids, the percentages are volume/volume percentages; the invention relates to the percentage between liquid and solid, said percentage being volume/weight percentage; the invention relates to the percentage between solids and liquids, the percentage being weight/volume percentage; the balance being weight/weight percent.
Compared with the prior art, the invention has the following beneficial technical effects:
1. according to the invention, the quality, purity and chelation rate of the alanine metal chelate are obviously improved and the production cost is obviously reduced by optimizing the chelation reaction conditions of the alanine and the metal salt.
2. The preparation method provided by the invention is simple and convenient to operate, the production period is obviously shortened, the production cost is obviously reduced, and the preparation method is suitable for large-scale industrial production.
Detailed Description
The present invention is described below with reference to examples, but the present invention is not limited to the examples.
Example 1Preparation of alanine chelated zinc
(1) 267.3g alanine was dissolved in 3L water to prepare an alanine solution;
(2) According to alanine: adding zinc chloride solution into the prepared alanine solution with the molar ratio of zinc chloride being 2:1, adding sodium hydroxide solution under the stirring condition, adjusting the pH value of the reaction solution to 6.0, and then placing the reaction solution in a water bath at 80 ℃ for ultrasonic treatment with the ultrasonic power of 100w for 1h to obtain the reaction solution;
(3) Vacuum concentrating (-0.085 MPa-0.095 MPa) to 500mL in water bath at 60-70deg.C;
(4) Adding 1.5L of absolute ethyl alcohol into the concentrated solution prepared in the step (3), placing the concentrated solution in a water bath at 70 ℃ for 1h, and then carrying out vacuum concentration (-0.085 MPa to-0.095 MPa) to be anhydrous at 70 ℃ to precipitate a large amount of white crystals;
(5) Adding 3.0-4.0L of absolute ethyl alcohol into the white crystal prepared in the step (4), stirring, cooling to 10 ℃, stirring a large amount of obtained white fine crystal suspension for 1h, centrifuging, collecting crystals, leaching with 0.5-1.0L of ethyl alcohol, and drying at 70 ℃ to obtain the alanine metal chelate.
The chelation rate is 91% when the detection method is adopted for detection.
Example 2Preparation of alanine chelated magnesium
(1) 300g of alanine was dissolved in 3.3L of water to prepare an alanine solution;
(2) According to alanine: adding a magnesium chloride solution into the prepared alanine solution at a molar ratio of 2:1, adding a sodium hydroxide solution under stirring, adjusting the pH value of the reaction solution to 6.0, and then placing the reaction solution in a water bath at 90 ℃ for ultrasonic treatment with ultrasonic power of 100w for 1h to obtain a reaction solution;
(3) - (5) the same as in example 1.
The chelation rate is 93% when the detection method is adopted for detection.
Example 3Preparation of alanine chelated copper
(1) 267.3g of alanine was weighed and dissolved in 3L of water to prepare an alanine solution;
(2) According to alanine: adding copper chloride solution into the prepared alanine solution according to the molar ratio of 2:1, stirring, dissolving, adding sodium hydroxide solution into the prepared reaction solution, adjusting the pH value of the reaction solution to 5.5, placing the reaction solution in a water bath at 80 ℃ for ultrasonic treatment, wherein the ultrasonic power is 100w, and the ultrasonic time is 1h, so as to obtain the reaction solution;
(3) - (5) the same as in example 1.
The chelation rate is 94% when the detection method is adopted for detection.
Example 4Preparation of alanine chelate chromium
(1) 350g of alanine was weighed and dissolved in 3.9L of water to prepare an alanine solution;
(2) According to alanine: adding a chromium chloride solution into the prepared alanine solution according to the molar ratio of 3:1, stirring, dissolving, adding a sodium hydroxide solution into the prepared reaction solution, adjusting the pH value of the reaction solution to 6.0, and then placing the reaction solution in a water bath at 80 ℃ for ultrasonic treatment with the ultrasonic power of 100w for 1h to obtain a reaction solution;
(3) - (5) the same as in example 1.
The chelation rate is 92% when the detection method is adopted for detection.
Example 5Preparation of alanine chelate calcium
(1) 250g of alanine was weighed and dissolved in 2.8L of water to prepare an alanine solution;
(2) According to alanine: adding a calcium chloride solution into the prepared alanine solution according to the molar ratio of 2:1, stirring, dissolving, adding a sodium hydroxide solution into the prepared reaction solution, adjusting the pH value of the reaction solution to 6.0, placing the reaction solution in a water bath at 80 ℃ for ultrasonic treatment, wherein the ultrasonic power is 100w, and the ultrasonic time is 2 hours to obtain the reaction solution;
(3) - (5) the same as in example 1.
The chelation rate is 94% when the detection method is adopted for detection.
Example 6Preparation of alanine chelated zinc
(1) 400g of alanine was weighed and dissolved in 4.5L of water to prepare an alanine solution;
(2) According to alanine: adding zinc chloride solution into the prepared alanine solution according to the molar ratio of 2:1, stirring, dissolving, adding sodium hydroxide solution into the prepared reaction solution, adjusting the pH value of the reaction solution to 6.0, placing the reaction solution in a water bath at 80 ℃ for ultrasonic treatment, wherein the ultrasonic power is 100w, and the ultrasonic time is 3.5 hours to obtain the reaction solution;
(3) - (5) the same as in example 1.
The chelation rate is 98% when the detection method is adopted for detection.
Comparative example 1Preparation of alanine chelated zinc
(1) 400g of alanine was weighed and dissolved in 4.5L of water to prepare an alanine solution;
(2) According to alanine: adding zinc chloride solution into the prepared alanine solution according to the molar ratio of zinc chloride of 2:1, stirring, dissolving, adding sodium hydroxide solution into the prepared reaction solution, adjusting the pH value of the reaction solution to 6.0, placing the reaction solution in a water bath at 50 ℃ for stirring treatment, wherein the stirring speed is 30r/min, and the stirring time is 1h, thus obtaining the reaction solution;
(3) - (5) the same as in example 1.
The chelation rate is 51% when the detection method is adopted for detection.
Comparative example 2Preparation of alanine chelated magnesium
(1) 300g of alanine was weighed and dissolved in 3.3L of water to prepare an alanine solution according to: adding a magnesium chloride solution into the prepared alanine solution according to the molar ratio of 2:1, stirring, dissolving, adding a sodium hydroxide solution into the prepared reaction solution, and regulating the pH value of the reaction solution to 7.0;
(2) Placing the mixed solution with the pH value adjusted in a water bath environment for stirring treatment, wherein the stirring speed is 30r/min, the stirring time is 1h, and the reaction temperature is 80 ℃ to obtain a reaction solution;
(3) - (9) the same as in example 1.
The chelation rate is 55% when the detection method is adopted for detection.
Comparative example 3Preparation of alanine chelated copper
(1) 267.3g of alanine was weighed and dissolved in 3L of water to prepare an alanine solution according to: adding copper chloride solution into the prepared alanine solution according to the molar ratio of 1:1, stirring, dissolving, adding sodium hydroxide solution into the prepared reaction solution, and regulating the pH value of the reaction solution to 6.0;
(2) Placing the mixed solution with the pH value adjusted in a water bath environment for stirring treatment, wherein the stirring speed is 30r/min, the stirring time is 1h, and the reaction temperature is 80 ℃ to obtain a reaction solution;
(3) - (9) the same as in example 1.
The chelation rate is 53% when the detection method is adopted for detection.
Comparative example 4Preparation of alanine chelate chromium
(1) 350g of alanine was weighed and dissolved in 3.9L of water to prepare an alanine solution according to: adding a chromium chloride solution into the prepared alanine solution according to the molar ratio of 2:1, stirring, dissolving, adding a sodium hydroxide solution into the prepared reaction solution, and adjusting the pH value of the reaction solution to 6.0;
(2) Placing the mixed solution with the pH value adjusted in a water bath environment for stirring treatment, wherein the stirring speed is 30r/min, the stirring time is 0.5h, and the reaction temperature is 80 ℃ to obtain a reaction solution;
(3) - (9) the same as in example 1.
The chelation rate is 59% when the detection method is adopted for detection.
The above description of the embodiments of the present invention is not intended to limit the present invention, and those skilled in the art can make various changes or modifications according to the present invention without departing from the spirit of the present invention, and shall fall within the scope of the claims of the present invention.
Claims (12)
1. The preparation method of the alanine metal chelate is characterized by comprising the following steps of: adding a metal salt solution into an alanine solution, performing chelation reaction under an acidic condition, concentrating, separating and drying the obtained reaction solution to obtain an alanine metal chelate;
in the chelation reaction, alanine: the molar ratio of the metal salt is 2:1-3:1, the chelating reaction pH is 5.5-6.0, and the chelating reaction temperature is 80-90 ℃; the chelation reaction is carried out ultrasonic treatment while stirring;
the metal salt is selected from any one or combination of zinc chloride, calcium chloride, magnesium chloride, ferric chloride, cupric chloride, chromium chloride, zinc nitrate, calcium nitrate, magnesium nitrate, ferric nitrate, cupric nitrate, chromium nitrate, zinc sulfate, calcium sulfate, magnesium sulfate, ferric sulfate, cupric sulfate and chromium sulfate.
2. The method of claim 1, wherein the alanine is selected from any one of L-alanine, D-alanine, a-alanine, β -alanine, DL-alanine, or a combination thereof.
3. The method of claim 1, wherein the chelation reaction pH is adjusted using an acid-base modifier selected from any one of sodium hydroxide, potassium hydroxide, sodium bicarbonate, sodium carbonate, or a combination thereof.
4. The method of claim 1, wherein the power of the sonication is 60-120W.
5. The method of claim 1, wherein the reaction time under the sonication conditions is from 1 to 6 hours.
6. The method of claim 1, wherein the number of sonications is 1-6.
7. The method of claim 1, wherein the concentrating is selected from any one of vacuum concentrating, membrane concentrating, atmospheric concentrating, ultrafiltration concentrating, centrifugal concentrating, or a combination thereof.
8. The method of claim 1, wherein the separation is selected from any one or a combination of crystallization, filtration, centrifugation, membrane treatment.
9. The method of claim 1, wherein the collected isolated solid is washed and dried.
10. The method of claim 1, wherein the drying is selected from any one of vacuum drying, reduced pressure drying, atmospheric pressure drying, spray drying, ebullient drying, or a combination thereof.
11. The method according to claim 1, wherein the produced alanine metal chelate complex is subjected to crystallization purification treatment.
12. The method of claim 11, wherein the crystallization purification treatment solvent is selected from any one of ethanol, propanol, methanol, butanol, acetone, isopropanol, isobutanol, ethyl acetate, or a combination thereof.
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| CN112409200B (en) * | 2020-11-27 | 2023-06-20 | 长沙兴嘉生物工程股份有限公司 | Preparation method and application of isoleucine chelate metal |
| CN112679234A (en) * | 2020-12-28 | 2021-04-20 | 秦皇岛华恒生物工程有限公司 | Comprehensive utilization method of beta-alanine crystallization mother liquor |
| CN112825968B (en) * | 2021-01-08 | 2024-02-13 | 广西壮族自治区畜牧研究所 | Buffalo feed based on amino acid metal ion chelate and application thereof |
| CN114014771B (en) * | 2021-06-30 | 2023-12-12 | 安徽华恒生物科技股份有限公司 | Ultra-high purity amino acid, preparation method and application thereof |
| CN114159422B (en) * | 2021-09-29 | 2023-02-28 | 北京天赋神奇科技有限公司 | Application of magnesium-containing water-soluble omega 3 fatty acid in promoting small intestine absorption capacity |
| CN115611759A (en) * | 2022-12-08 | 2023-01-17 | 维卓(嘉兴)营养品有限公司 | Preparation method of (R) -3-aminobutyric acid chelated calcium |
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