CN101289411B - Method for preparing zinc threonine - Google Patents
Method for preparing zinc threonine Download PDFInfo
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- CN101289411B CN101289411B CN200810106870.1A CN200810106870A CN101289411B CN 101289411 B CN101289411 B CN 101289411B CN 200810106870 A CN200810106870 A CN 200810106870A CN 101289411 B CN101289411 B CN 101289411B
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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 the crystal water: C
8h
16n
2o
6zn2H
2the threonine zinc preparation method of O.
Technical background
At present, the trace element that China's food and feed adds in producing is mainly inorganic metal mineral substance.Mainly there is following problem in inorganic microelement additive:
(1) absorption rate is low: inorganic metal ion phytic acid, phosphoric acid, oxalic acid equimolecular easily and in food or feed in gi tract forms the insoluble chemical compound being difficult for by human body and animal absorption, different divalent-metal ions may produce antagonism, affect its absorption at small intestine and body utilization ratio, even if cause in a large number, adding, still may there is trace element deficiency in human body or animal.
(2) destruction to other nutrient substances: free divalent-metal ion easily makes some VITAMIN oxidation inactivation, fats oxidn in induction food or feed produces peroxylradicals, body is produced to harm, as cause immunological competence decline, production performance reduction etc.
(3) drawback that excess is added: excess is added inorganic mineral can cause pessimal stimulation to animal gastrointestinal tract, promotes harmful bacteria breeding, increases the sickness rate of digestive tract diseases.Meanwhile, too much metallic element is discharged with ight soil, gives environment.
In feed, adding appropriate organic microelement chelate is to solve inorganic microelement excess in feed to add, improve relatively effective means of absorption of trace elements utilization ratio.Organic microelement chelate (Organic Micrometal Chelates, OMC) refers to atom centered by trace element ion, and by the ring compound forming after coordinate bond and part coordination, molecular weight is generally no more than 800.Research shows, the Lethal Dose 50 of microelements aminophenol chelated is greater than inorganic salt, is safer third generation trace mineral supplement.
Microelements aminophenol chelated is to take amino acid as part, by amino acid whose carboxyl oxygen atom and amino nitrogen atom and central metallic ions formation coordinate bond, with 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) pH environment stability inferior and solvability are better in vivo, and specific absorption exceeds inorganic salt more than three times, has higher biological value.
(2) there is good biochemical stability, in digestive tube, greatly reduce the antagonistic action between divalent-metal ion, also reduced the chance with the combination such as phytic acid, oxalic acid simultaneously, be conducive to absorbing of enteron aisle.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 directly be absorbed and be entered blood plasma by mucous membrane of small intestine with the form of similar dipeptides, 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, 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 producing: C
8h
16n
2o
6zn, or molecular formula is when the crystal water: C
8h
16n
2o
6zn2H
2o) can meet human body and the animal nutritional needs to zinc, also can be human body and animal provides indispensable amino acid---the nutrition of Threonine.
The present invention is achieved like this, and take Threonine and zinc oxide as raw material, in water medium, reacts, and it is characterized in that Threonine and zinc mol ratio are for (7.00-2.00): 1, and at 50 ℃ of-100 ℃ of temperature, stirring reaction to solution is clarified.Continue reaction 0.5-3.0h, finish reaction, reaction solution cooling spontaneous nucleation, filtering separation, washing, dry, pulverize, and prepares threonine zinc product.
Spontaneous nucleation after above-mentioned reaction solution cooling, the filtrate after separation and Extraction threonine zinc, can continue to utilize, and as the reaction medium reacting next time, raw material makes full use of, and reaches the object reducing costs.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, so there is no other by product in last reactant, improved the purity of product, and reduced the discharge of by product, meet the current requirement to environmental protection.The present invention has the advantages such as technique is simple, yield is high, quality of finished is good.
Also available zinc subcarbonate, zinc carbonate, zinc hydroxide replacement zinc oxide are raw material in the present invention.
In the present invention, after reaction finishes, in reaction solution, can add organic solvent, as methyl alcohol or ethanol, acetone etc. carry out rapid precipitation product, filtering separation, washing, dry, prepare threonine zinc product.
In the present invention, after reaction finishes, reaction solution can vacuum concentration, partial crystallization, and filtering separation, washing, dry, pulverize, and prepares threonine zinc product.
Advantage of the present invention is: the present invention utilizes market value to belong to cheaply, again the indispensable amino acid of human body and animal---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: be 1. neutral; 2. molecular weight is little, and molecular weight is 301.60, and during containing two crystal water, molecular weight is 337.63; 3. can integral body be absorbed.With other amino-acid zinc inner complex comparisons on market, demonstrate unique feature.With zinc glycinate comparison, Threonine, as one of the indispensable amino acids of livestock and poultry (the second limiting amino acid, bird the 3rd limiting amino acid in pig), is widely used in livestock and poultry; With zinc methionine, lysine-zn comparison, it does not have methionine(Met), the special peculiar smell of Methionin.
The Bioexperiment result that the threonine zinc that the present invention makes supplements zinc for 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%.With Zinc Gluconate comparison, 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 for showing the research experiment result of performance in layers and Egg Quality impact: threonine zinc can improve performance in layers, contrasts and compares with zinc sulfate, adds 35ppm with in 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 to add the efficiency that absorbs that threonine zinc improves zinc.With zinc lactate comparison, add 70ppm with in 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 Threonine 71.4g (0.60mol), be dissolved in 250mL water.Then in Threonine solution, slowly add Zinc oxide powder 20.3g (0.25mol), the mol ratio of Threonine and zinc oxide is 2.4: 1, at 95 ℃ of stirring reaction to solution, clarifies, and 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, pulverize, and obtains 74.7g threonine zinc.Reaction yield 88.50%, molecular formula is: C
8h
16n
2o
6zn.
Embodiment 2
The threonine zinc reacting liquid filtering generating in example 1 falls crystallized product, and filtrate is stand-by.Can continue to add Zinc oxide powder reaction; Or as reaction solvent, the medium reacting with zinc oxide as Threonine, recycles.Threonine 100% is utilized, and reaction yield almost can reach 100%, and molecular formula is: C
8h
16n
2o
6zn.
Embodiment 3
Take Threonine 71.4g (0.60mol), be dissolved in 250mL water.Then in Threonine solution, slowly add Zinc oxide powder 20.3g (0.25mol), the mole ratio of Threonine and zinc oxide is 2.4: 1, at 95 ℃ of stirring reaction to solution, clarifies, and continues reaction 0.5h.Stopped reaction, cooling, add ethanol, make threonine zinc Precipitation, be precipitated as slightly micro-light yellow solid, filter, washing, 50 ℃, 0.10MPa vacuum-drying, pulverize, and obtains 80.60g threonine zinc.Reaction yield 95.50%, molecular formula is: C
8h
16n
2o
6zn2H
2o.
Embodiment 4
Take Threonine 71.4g (0.60mol), be dissolved in 250mL water.Then in Threonine solution, slowly add Zinc oxide powder 16.20g (0.20mol), the mol ratio of Threonine and zinc oxide is 3.0: 1, at 85 ℃ of stirring reaction to solution, clarifies, and 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, pulverize, and obtains 60.8g threonine zinc.Reaction yield 90.00%, molecular formula is: C
8h
16n
2o
6zn.
Embodiment 5
Take Threonine 35.7g (0.300mol), be dissolved in 200mL water.Then in Threonine solution, slowly add zinc subcarbonate (3Zn (OH)
22ZnCO
3) 11g (0.02mol), the mol ratio of Threonine and zinc is 3: 1, at 90 ℃ of stirring reactions, reacts to solution clarification, continues reaction 1h.Stopped reaction, cooling, standing over night, threonine zinc Precipitation, throw out, for the translucent block crystal of band metalluster granulated sugar shape milk yellow, filters, washing, 60 ℃, 0.10MPa vacuum-drying, pulverize, and obtains 28.3g threonine zinc.Reaction yield 83.82%, molecular formula is: C
8h
16n
2o
6zn2H
2o.
Embodiment 6
Take Threonine 35.7g (0.300mol), be dissolved in 200mL water.Then in Threonine solution, slowly add zinc subcarbonate (3Zn (OH)
22ZnCO
3) 11g (0.02mol), the mol ratio of Threonine and zinc is 3: 1, at 90 ℃ of stirring reactions, reacts to solution clarification, continues reaction 1h.Stopped reaction, cooling, add the quick crystallization of ethanol of a certain amount of volume, be precipitated as slightly micro-light yellow solid, filter, washing, 60 ℃, 0.10MPa vacuum-drying, pulverize, and obtains 30.1g threonine zinc.Reaction yield 89.15%, molecular formula is: C
8h
16n
2o
6zn2H
2o.
Embodiment 7
Take Threonine 47.6g (0.400mol), be dissolved in 250mL water.Then in Threonine solution, slowly add zinc subcarbonate (3Zn (OH)
22ZnCO
3) 11g (0.02mol), the mol ratio of Threonine and zinc is 4: 1, at 85 ℃ of stirring reactions, reacts to solution clarification, continues reaction 1.5h.Stopped reaction, cooling, standing over night, threonine zinc Precipitation, throw out, for the translucent block crystal of band metalluster granulated sugar shape milk yellow, filters, washing, 60 ℃, 0.10MPa vacuum-drying, pulverize, and obtains 29.2g threonine zinc.Reaction yield 86.62%, molecular formula is: C
8h
16n
2o
6zn.
Embodiment 8
Take Threonine 35.7g (0.300mol), be dissolved in 200mL water.Then in Threonine solution, slowly add zinc subcarbonate (3Zn (OH)
22ZnCO
3) 11g (0.02mol), the mol ratio of Threonine and zinc is 3: 1, at 90 ℃ of stirring reactions, reacts to solution clarification, continues reaction 1h.Stopped reaction, cooling, standing over night, threonine zinc Precipitation, throw out, for the translucent block crystal of band metalluster granulated sugar shape milk yellow, filters, washing, 60 ℃, 0.10MPa vacuum-drying, pulverize, and obtains 28.3g threonine zinc.Reaction yield 83.82%, molecular formula is: C
8h
16n
2o
6zn2H
2o.
Embodiment 9
Take Threonine 71.4g (0.300mol), be dissolved in 200mL water.Then in Threonine solution, slowly add zinc subcarbonate (3Zn (OH)
22ZnCO
3) 11g (0.02mol), the mol ratio of Threonine and zinc is 6: 1, at 50 ℃ of stirring reactions, reacts to solution clarification, continues reaction 3.0h.Stopped reaction, cooling, standing over night, threonine zinc Precipitation, throw out, for the translucent block crystal of band metalluster granulated sugar shape milk yellow, filters, washing, 60 ℃, 0.10MPa vacuum-drying, pulverize, and obtains 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 take Threonine and zinc oxide is raw material, in water medium, reacts, the mol ratio that it is characterized in that Threonine and zinc is 7.00～2.00: 1, at 50 ℃～100 ℃ temperature, stirring reaction to solution is clarified, and continues reaction 0.5～3.0h, finishes reaction, reaction solution cooling spontaneous nucleation, filtering separation, washing, dry, pulverize, prepare threonine zinc product.
2. the preparation method of threonine zinc according to claim 1, is characterized in that with zinc subcarbonate, zinc carbonate, zinc hydroxide, replacing zinc oxide is raw material.
3. the preparation method of threonine zinc according to claim 1 after it is characterized in that reaction finishes, adds organic solvent methyl alcohol, ethanol or acetone to carry out rapid precipitation product in reaction solution, filtering separation, and washing, dry, pulverize, and prepares threonine zinc product.
4. the preparation method of threonine zinc according to claim 1, after it is characterized in that reaction finishes, reaction solution vacuum concentration, partial crystallization, filtering separation, washing, dry, pulverize, and prepares threonine zinc product.
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|---|---|---|---|
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|---|---|---|---|
| CN200810106870.1A CN101289411B (en) | 2008-05-23 | 2008-05-23 | Method for preparing zinc threonine |
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| CN101289411B true CN101289411B (en) | 2014-04-09 |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1529774A2 (en) * | 2003-11-04 | 2005-05-11 | Grillo Zinkoxid GmbH | Process for the preparation of an organozinc derivative and its use in a zinc-containing composition as nutritional supplement |
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- 2008-05-23 CN CN200810106870.1A patent/CN101289411B/en not_active Expired - Fee Related
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1529774A2 (en) * | 2003-11-04 | 2005-05-11 | Grillo Zinkoxid GmbH | Process for the preparation of an organozinc derivative and its use in a zinc-containing composition as nutritional supplement |
Non-Patent Citations (1)
| Title |
|---|
| 高胜利等.锌添加剂的合成.《化学通报》.1999,第1999年卷(第11期),30-34页. * |
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