CN101289411A - Method for preparing zinc threonine - Google Patents
Method for preparing zinc threonine Download PDFInfo
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- CN101289411A CN101289411A CNA2008101068701A CN200810106870A CN101289411A CN 101289411 A CN101289411 A CN 101289411A CN A2008101068701 A CNA2008101068701 A CN A2008101068701A CN 200810106870 A CN200810106870 A CN 200810106870A CN 101289411 A CN101289411 A CN 101289411A
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Abstract
The invention relates to a preparation method of zinc threonine which takes threonine and zinc oxide as raw materials reacting in water medium. The molar ratio of the threonine to the zinc oxide is (7.00 to 2.00) to 1. The product of zinc threonine (the formula is C8H16N2O6Zn or the formula with crystal water is C8H16N2O6Zn.2H2O) is prepared by reaction of being stirred at the temperature of 50 DEG C to 100 DEG C. The method takes the threonine, the zinc oxide and other zinc salt which are low in market price and indispensable to human body and animal as raw materials to synthesize the zinc threonine. The prepared zinc threonine meets the requirement of physiological conditions: (1) being neutral; (2) small molecular weight of 301.60, and 337.63 with two crystal waters; (3) being capable of being absorbed as a whole.
Description
Technical field
The present invention relates to a kind of preparation method of threonine zinc, relate in particular to molecular formula and be: C
8H
16N
2O
6Zn, or molecular formula is when containing crystal water: C
8H
16N
2O
6Zn2H
2The threonine zinc preparation method of O.
Technical background
At present, the trace element that adds in China's food and the fodder production mainly is the inorganic metal mineral substance.Mainly there is following problem in the inorganic microelement additive:
(1) absorption rate is low: inorganic metal ion in gi tract easily with food or feed in phytic acid, phosphoric acid, oxalic acid equimolecular form the insoluble chemical compound that is difficult for by human body and animal absorption, different divalent-metal ions may produce antagonism, influence its absorption and body utilization ratio at small intestine, even cause heavy addition, human body or animal still trace element deficiency may occur.
(2) to the destruction of other nutrient substances: the free divalent-metal ion easily makes some VITAMIN oxidation inactivation, induce the fats oxidn in food or the feed to produce peroxylradicals, body is produced harm, as cause immunological competence decline, production performance reduction etc.
(3) drawback of excess interpolation: excess is added inorganic mineral can cause pessimal stimulation to animal gastrointestinal tract, promotes harmful bacterium breeding, the sickness rate of increase digestive tract diseases.Simultaneously, too much metallic element is discharged with ight soil, pollutes to environment.
Adding an amount of organic microelement chelate in feed is to solve relatively effective means of inorganic microelement excess interpolation in the feed, the micro-absorption rate of raising.(Organic Micrometal Chelates OMC) is meant that with micro-ion be central atom to organic microelement chelate, and by the ring compound that forms after coordinate bond and the part coordination, molecular weight generally is no more than 800.Studies show that the Lethal Dose 50 of microelements aminophenol chelated is safer third generation trace mineral supplements greater than inorganic salt.
Microelements aminophenol chelated is to be part with amino acid, by amino acid whose carboxyl oxygen atom and amino nitrogen atom and central metallic ions formation coordinate bond, have the coordination compound of five-ring or six-ring, it is neutral that intramolecular charge is, compare with corresponding inorganic salt, its major advantage is:
(1) following stability of pH environment and solvability are better in vivo, and specific absorption exceeds inorganic salt more than three times, has higher biological value.
(2) have good biochemical stability, in digestive tube, greatly reduce the antagonistic action between divalent-metal ion, also reduced and bonded chances such as phytic acid, oxalic acid simultaneously, help absorbing of enteron aisle.The absorption approach and the metabolic mechanism of microelements aminophenol chelated are different from inorganic salt, and it can enter intestinal cells by the absorption approach of amino acid or peptide.Metal-amino acid chelate can be with the form of similar dipeptides, directly absorbed by mucous membrane of small intestine to enter blood plasma, and the approach of the active absorption of needn't going further, thereby reduced energy consumption, improved specific absorption.
(3) under same dose, organic trace element can effectively promote growth of animal, improve efficiency of feed utilization, increases trace element (as iron, zinc, selenium, chromium etc.) content in meat, egg, the milk, improves its nutritive value.
Summary of the invention
The object of the present invention is to provide the preparation method of threonine zinc, (molecular formula is the threonine zinc of being produced: C
8H
16N
2O
6Zn, or molecular formula is when containing crystal water: C
8H
16N
2O
6Zn2H
2O) can satisfy human body and animal nutritional needs, also can be human body and animal provides indispensable amino acid zinc---the nutrition of Threonine.
The present invention is achieved like this, and is raw material with Threonine and zinc oxide, reacts in water medium, it is characterized in that Threonine and zinc mol ratio are (7.00-2.00): 1, and stirring reaction to solution is clarified under 50 ℃ of-100 ℃ of temperature.Continue reaction 0.5-3.0h, finish reaction, reaction solution cooling spontaneous nucleation, filtering separation, washing, drying is pulverized, and prepares the threonine zinc product.
Above-mentioned reaction solution cooling back spontaneous nucleation, the filtrate behind the separation and Extraction threonine zinc can continue to utilize, and as the reaction medium that reacts next time, raw material makes full use of, and reaches the purpose that reduces cost.The present invention utilizes the acidity of Threonine and the alkalescence of zinc oxide directly to carry out neutralization reaction, do not need to add other reagent,, improved the purity of product so in last reactant, there is not other by product, and reduced the discharge of by product, meet now to environmental protection requirement.The present invention has advantages such as technology is simple, yield is high, quality of finished is good.
It is raw material that also available in the present invention zinc subcarbonate, zinc carbonate, zinc hydroxide are replaced zinc oxide.
After reaction finishes, can add organic solvent in the reaction solution among the present invention, carry out rapid precipitation product, filtering separation, washing, drying, prepare the threonine zinc product as methyl alcohol or ethanol, acetone etc.
After reaction finished, reaction solution can vacuum concentration among the present invention, partial crystallization, and filtering separation, washing, drying is pulverized, and prepares the threonine zinc product.
Advantage of the present invention is: the present invention utilizes market value to belong to the indispensable amino acid of human body and animal cheaply, again---and Threonine and zinc oxide and other zinc salts are raw material, have synthesized threonine zinc.The threonine zinc that the present invention makes meets physiological condition and requires: 1. be neutral; 2. molecular weight is little, and molecular weight is 301.60, and molecular weight is 337.63 when containing two crystal water; 3. can integral body be absorbed.Compare with other amino-acid zinc inner complexs on the market, demonstrate unique characteristics.With zinc glycinate relatively, Threonine is widely used in livestock and poultry as one of the indispensable amino acids of livestock and poultry (second limiting amino acid, bird the 3rd limiting amino acid in the pig); Compare with zinc methionine, lysine-zn, it does not have methionine(Met), the special peculiar smell of Methionin.
The Bioexperiment result that the threonine zinc that the present invention makes is used for the additional zinc of weanling pig shows: with ZnSO
4Relatively, can improve piglet average daily gain (ADG) 28.3%, per day food consumption (ADFI) 29.6% increases by 2.41 times of serum zinc concentration and IgG content 1.62%.Compare with Zinc Gluconate, can improve piglet average daily gain (ADG) 15.3%, per day food consumption (ADFI) 18.2% increases by 1.31 times of serum zinc concentration and IgG content 1.03%.
The threonine zinc that the present invention makes is used for the research experiment result of laying hen production performance and the influence of egg product matter is shown: threonine zinc can improve the laying hen production performance, compares with the zinc sulfate contrast, adds 35ppm with under the dosage situation, and laying rate improves 10.91%; Average daily output egg size improves 8.25%; Efficiency of feed utilization improves 9.32%; The deposition of egg zinc is higher; Add threonine zinc and significantly improve laying hen serum zinc and alkaline phosphatase enzyme level, show and add the efficient that absorbs that threonine zinc improves zinc.Compare with zinc lactate, add 70ppm with under the dosage situation, laying rate improves 5.85%; Average daily output egg size improves 5.02%; Efficiency of feed utilization improves 6.32%; The deposition of egg zinc is higher.
Embodiment
Embodiment 1
Take by weighing Threonine 71.4g (0.60mol), be dissolved in the 250mL water.Slowly add Zinc oxide powder 20.3g (0.25mol) then in Threonine solution, the mol ratio of Threonine and zinc oxide is 2.4: 1, clarifies at 95 ℃ of stirring reaction to solution, continues reaction 0.5h.Stopped reaction, standing over night, solution precipitation goes out the colourless translucent crystal of a large amount of rosettes, filters, washing, 50 ℃, 0.10MPa vacuum-drying are pulverized, and obtain the 74.7g threonine zinc.Reaction yield 88.50%, molecular formula is: C
8H
16N
2O
6Zn.
Embodiment 2
The threonine zinc reacting liquid filtering that generates in the example 1 falls crystallized product, and filtrate is stand-by.Can continue to add the Zinc oxide powder reaction; Or as reaction solvent, the medium as Threonine and zinc oxide reaction recycles.Threonine 100% is utilized, and reaction yield almost can reach 100%, and molecular formula is: C
8H
16N
2O
6Zn.
Embodiment 3
Take by weighing Threonine 71.4g (0.60mol), be dissolved in the 250mL water.Slowly add Zinc oxide powder 20.3g (0.25mol) then in Threonine solution, the mole ratio of Threonine and zinc oxide is 2.4: 1, clarifies at 95 ℃ of stirring reaction to solution, continues reaction 0.5h.Stopped reaction, cooling adds ethanol, and the threonine zinc precipitation is separated out, and is precipitated as slightly little light yellow solid, filter, washing, 50 ℃, 0.10MPa vacuum-drying are pulverized, and obtain the 80.60g threonine zinc.Reaction yield 95.50%, molecular formula is: C
8H
16N
2O
6Zn2H
2O.
Embodiment 4
Take by weighing Threonine 71.4g (0.60mol), be dissolved in the 250mL water.Slowly add Zinc oxide powder 16.20g (0.20mol) then in Threonine solution, the mol ratio of Threonine and zinc oxide is 3.0: 1, clarifies at 85 ℃ of stirring reaction to solution, continues reaction 0.5h.Stopped reaction, standing over night, solution precipitation goes out the colourless translucent crystal of a large amount of rosettes, filters, washing, 50 ℃, 0.10MPa vacuum-drying are pulverized, and obtain the 60.8g threonine zinc.Reaction yield 90.00%, molecular formula is: C
8H
16N
2O
6Zn.
Embodiment 5
Take by weighing Threonine 35.7g (0.300mol), be dissolved in the 200mL water.In Threonine solution, slowly add zinc subcarbonate (3Zn (OH) then
22ZnCO
3) 11g (0.02mol), the mol ratio of Threonine and zinc is 3: 1, at 90 ℃ of stirring reactions, reacts to the solution clarification, continues reaction 1h.Stopped reaction, cooling, standing over night, the threonine zinc precipitation is separated out, and throw out filters for the translucent block crystal of band metalluster granulated sugar shape milk yellow, washing, 60 ℃, 0.10MPa vacuum-drying are pulverized, and obtain the 28.3g threonine zinc.Reaction yield 83.82%, molecular formula is: C
8H
16N
2O
6Zn2H
2O.
Embodiment 6
Take by weighing Threonine 35.7g (0.300mol), be dissolved in the 200mL water.In Threonine solution, slowly add zinc subcarbonate (3Zn (OH) then
22ZnCO
3) 11g (0.02mol), the mol ratio of Threonine and zinc is 3: 1, at 90 ℃ of stirring reactions, reacts to the solution clarification, continues reaction 1h.Stopped reaction, cooling adds the quick crystallization of a certain amount of volume of ethanol, is precipitated as slightly little light yellow solid, filter, washing, 60 ℃, 0.10MPa vacuum-drying are pulverized, and obtain the 30.1g threonine zinc.Reaction yield 89.15%, molecular formula is: C
8H
16N
2O
6Zn2H
2O.
Embodiment 7
Take by weighing Threonine 47.6g (0.400mol), be dissolved in the 250mL water.In Threonine solution, slowly add zinc subcarbonate (3Zn (OH) then
22ZnCO
3) 11g (0.02mol), the mol ratio of Threonine and zinc is 4: 1, at 85 ℃ of stirring reactions, reacts to the solution clarification, continues reaction 1.5h.Stopped reaction, cooling, standing over night, the threonine zinc precipitation is separated out, and throw out filters for the translucent block crystal of band metalluster granulated sugar shape milk yellow, washing, 60 ℃, 0.10MPa vacuum-drying are pulverized, and obtain the 29.2g threonine zinc.Reaction yield 86.62%, molecular formula is: C
8H
16N
2O
6Zn.
Embodiment 8
Take by weighing Threonine 35.7g (0.300mol), be dissolved in the 200mL water.In Threonine solution, slowly add zinc subcarbonate (3Zn (OH) then
22ZnCO
3) 11g (0.02mol), the mol ratio of Threonine and zinc is 3: 1, at 90 ℃ of stirring reactions, reacts to the solution clarification, continues reaction 1h.Stopped reaction, cooling, standing over night, the threonine zinc precipitation is separated out, and throw out filters for the translucent block crystal of band metalluster granulated sugar shape milk yellow, washing, 60 ℃, 0.10MPa vacuum-drying are pulverized, and obtain the 28.3g threonine zinc.Reaction yield 83.82%, molecular formula is: C
8H
16N
2O
6Zn2H
2O.
Embodiment 9
Take by weighing Threonine 71.4g (0.300mol), be dissolved in the 200mL water.In Threonine solution, slowly add zinc subcarbonate (3Zn (OH) then
22ZnCO
3) 11g (0.02mol), the mol ratio of Threonine and zinc is 6: 1, at 50 ℃ of stirring reactions, reacts to the solution clarification, continues reaction 3.0h.Stopped reaction, cooling, standing over night, the threonine zinc precipitation is separated out, and throw out filters for the translucent block crystal of band metalluster granulated sugar shape milk yellow, washing, 60 ℃, 0.10MPa vacuum-drying are pulverized, and obtain the 30.3g threonine zinc.Reaction yield 84.28%, molecular formula is: C
8H
16N
2O
6Zn.
Claims (4)
1, the preparation method of threonine zinc, it is a raw material with Threonine and zinc oxide, reacts in water medium, the mol ratio that it is characterized in that Threonine and zinc is 7.00-2.00: 1, stirring reaction to solution is clarified under 50 ℃ of-100 ℃ of temperature, continues reaction 0.5-3.0h, finishes reaction, reaction solution cooling spontaneous nucleation, filtering separation, washing, drying, pulverize, prepare the threonine zinc product.
2,, it is characterized in that it is raw material that available zinc subcarbonate, zinc carbonate, zinc hydroxide are replaced zinc oxide according to the preparation method of the described threonine zinc of claim 1.
3,, after it is characterized in that reacting end, can in reaction solution, add organic solvent according to the preparation method of the described threonine zinc of claim 1, carry out the rapid precipitation product as methyl alcohol, ethanol, acetone, filtering separation, washing, drying is pulverized, and prepares the threonine zinc product.
4, according to the preparation method of the described threonine zinc of claim 1, it is characterized in that reaction finishes after, reaction solution can vacuum concentration, partial crystallization, filtering separation, washing, drying is pulverized, and prepares the threonine zinc product.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810106870.1A CN101289411B (en) | 2008-05-23 | 2008-05-23 | Method for preparing zinc threonine |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810106870.1A CN101289411B (en) | 2008-05-23 | 2008-05-23 | Method for preparing zinc threonine |
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| Publication Number | Publication Date |
|---|---|
| CN101289411A true CN101289411A (en) | 2008-10-22 |
| CN101289411B CN101289411B (en) | 2014-04-09 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200810106870.1A Expired - Fee Related CN101289411B (en) | 2008-05-23 | 2008-05-23 | Method for preparing zinc threonine |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102488098A (en) * | 2011-12-28 | 2012-06-13 | 长沙兴加生物技术有限公司 | Zinc threonine for animal feed additive and preparation method and application thereof |
| CN110897039A (en) * | 2019-12-26 | 2020-03-24 | 长沙兴嘉生物工程股份有限公司 | Preparation method and application of manganese valine |
| CN111072508A (en) * | 2019-12-25 | 2020-04-28 | 长沙兴嘉生物工程股份有限公司 | Preparation method and application of zinc valine |
| CN115385812A (en) * | 2022-07-29 | 2022-11-25 | 宁夏太康药业有限公司 | Preparation method of sarcosine zinc chelate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10352129A1 (en) * | 2003-11-04 | 2005-06-16 | Grillo Zinkoxid Gmbh | A process for preparing an organozinc compound and its use in a zinciferous composition for nutritional supplementation |
-
2008
- 2008-05-23 CN CN200810106870.1A patent/CN101289411B/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102488098A (en) * | 2011-12-28 | 2012-06-13 | 长沙兴加生物技术有限公司 | Zinc threonine for animal feed additive and preparation method and application thereof |
| CN102488098B (en) * | 2011-12-28 | 2014-05-14 | 长沙兴加生物技术有限公司 | Zinc threonine for animal feed additive and preparation method and application thereof |
| CN111072508A (en) * | 2019-12-25 | 2020-04-28 | 长沙兴嘉生物工程股份有限公司 | Preparation method and application of zinc valine |
| CN111072508B (en) * | 2019-12-25 | 2021-08-10 | 长沙兴嘉生物工程股份有限公司 | Preparation method and application of zinc valine |
| CN110897039A (en) * | 2019-12-26 | 2020-03-24 | 长沙兴嘉生物工程股份有限公司 | Preparation method and application of manganese valine |
| CN110897039B (en) * | 2019-12-26 | 2023-02-03 | 长沙兴嘉生物工程股份有限公司 | Preparation method and application of manganese valine |
| CN115385812A (en) * | 2022-07-29 | 2022-11-25 | 宁夏太康药业有限公司 | Preparation method of sarcosine zinc chelate |
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| Publication number | Publication date |
|---|---|
| CN101289411B (en) | 2014-04-09 |
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