CN103922954A - Method for preparing glycine zinc chelate - Google Patents
Method for preparing glycine zinc chelate Download PDFInfo
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- CN103922954A CN103922954A CN201410131404.4A CN201410131404A CN103922954A CN 103922954 A CN103922954 A CN 103922954A CN 201410131404 A CN201410131404 A CN 201410131404A CN 103922954 A CN103922954 A CN 103922954A
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- zinc
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- glycine
- sodium hydroxide
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- UOXSXMSTSYWNMH-UHFFFAOYSA-L zinc;2-aminoacetate Chemical compound [Zn+2].NCC([O-])=O.NCC([O-])=O UOXSXMSTSYWNMH-UHFFFAOYSA-L 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 14
- 229940038842 glycine zinc chelate Drugs 0.000 title abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 99
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 66
- 239000000243 solution Substances 0.000 claims abstract description 52
- 239000004471 Glycine Substances 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 150000003751 zinc Chemical class 0.000 claims abstract description 21
- 230000032683 aging Effects 0.000 claims abstract description 9
- 239000012266 salt solution Substances 0.000 claims abstract description 7
- 239000013078 crystal Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract 2
- 229940071566 zinc glycinate Drugs 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 17
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000004246 zinc acetate Substances 0.000 claims description 3
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 3
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 229960001763 zinc sulfate Drugs 0.000 claims description 2
- 238000000151 deposition Methods 0.000 claims 4
- 230000008021 deposition Effects 0.000 claims 4
- 230000015572 biosynthetic process Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 30
- 239000002244 precipitate Substances 0.000 abstract description 15
- 230000001276 controlling effect Effects 0.000 abstract description 7
- 230000001105 regulatory effect Effects 0.000 abstract description 6
- 239000000047 product Substances 0.000 abstract description 5
- 238000005265 energy consumption Methods 0.000 abstract description 3
- RUECTJATXCACED-UHFFFAOYSA-N 2-aminoacetic acid;hydrate Chemical compound [OH-].[NH3+]CC(O)=O RUECTJATXCACED-UHFFFAOYSA-N 0.000 abstract 2
- HGSXDBRNFBJIMX-UHFFFAOYSA-N 2-aminoacetic acid;zinc Chemical compound [Zn].NCC(O)=O HGSXDBRNFBJIMX-UHFFFAOYSA-N 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 230000036632 reaction speed Effects 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 18
- 239000008367 deionised water Substances 0.000 description 13
- 229910021641 deionized water Inorganic materials 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 10
- 239000011701 zinc Substances 0.000 description 10
- 229910052725 zinc Inorganic materials 0.000 description 10
- 238000000967 suction filtration Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000036039 immunity Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UOURRHZRLGCVDA-UHFFFAOYSA-D pentazinc;dicarbonate;hexahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[O-]C([O-])=O.[O-]C([O-])=O UOURRHZRLGCVDA-UHFFFAOYSA-D 0.000 description 2
- 238000010532 solid phase synthesis reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 239000011573 trace mineral Substances 0.000 description 2
- 235000013619 trace mineral Nutrition 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000014860 sensory perception of taste Effects 0.000 description 1
- 229940126680 traditional chinese medicines Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for preparing a glycine zinc chelate. The method comprises steps of 1, preparing zinc salt solution, glycine water solution and sodium hydroxide water solution; 2, simultaneously dripping zinc salt solution and sodium hydroxide water solution into the glycine water solution, regulating the speed of dripping the sodium hydroxide water solution, controlling the pH value of a reaction solution to be 5-7, reacting so as to obtain white precipitate, ageing the white precipitate in the reaction solution for 8-15 hours; 3, carrying out suction filtering on the mixture formed by the white precipitate obtained in step 2 and the reaction solution at reduced pressure, and then drying the mixture, so as to obtain tabular white crystal. As the soluble zinc salt and glycine react in water solution, the method has characteristics of high reaction speed and high product purity. In addition, the method can be carried out at room temperature and has the advantage of low energy consumption. Moreover, the prepared glycine zinc has the platelike geometrical shape.
Description
Technical field
The present invention relates to, containing chelates of zinc preparing technical field, particularly relate to a kind of preparation method of zinc glycinate inner complex.
Background technology
Zinc is one of life trace element, is also that humans and animals sustains life and one of the requisite nutrient substance of growing, and participates in composition and the metabolism of plurality of enzymes in body.Zinc has accelerating growth to be grown, improves the sense of taste, regulate human body immunity, protect from infection and promote the functions such as wound healing, and scarce zinc can produce various diseases.A large number of experiments show that, zinc glycinate can improve immunity of organisms, and breeding performonce fo animals is provided, and has no side effect, and compares with inorganic zinc salt, has that bioavailability is high, absorption rate is fast and good chemical stability.
The preparation method of zinc glycinate can be divided into solid-phase synthesis and aqueous phase synthesis method conventionally.The prior art of solid-phase synthesis (chemistry world, 2005,9:547-550) take glycine and zinc acetate as raw material, adopt scorification to synthesize Zinc bisglycinate.When synthetic, raw material need be heated to 125 ℃, under molten state, reacts 0.5h.The method power consumption is higher, and the zinc glycinate of generation is not containing crystal water, and product does not have definite geometrical shape.The prior art of aqueous phase synthesis method (journal of Zhejiang university (Edition), 2008,35 (4)) take glycine and zinc subcarbonate as raw material, because the solubleness of zinc subcarbonate is lower, need between 90～95 ℃, heated and stirred react 6h, filtered while hot.Filtrate obtains product through operations such as heating in water bath, concentrated, crystallization, suction filtration, washings again.The method reaction times is longer, operates more loaded down with trivial details.
As can be seen here, also there is the shortcomings such as process is loaded down with trivial details, time consumption and energy consumption in existing various preparation methods, is difficult for realizing suitability for industrialized production.
Summary of the invention
Technical problem to be solved by this invention is to overcome that preparation process in prior art is loaded down with trivial details, time consumption and energy consumption, be difficult for realizing the shortcoming of suitability for industrialized production, and zinc glycinate prepared by the method has definite crystal shape, and product purity is high.
The technical scheme that the present invention solves the problems of the technologies described above is as follows: a kind of preparation method of zinc glycinate inner complex, and adopt soluble zinc salt and glycine to react in the aqueous solution, by sodium hydroxide, regulate the pH value of reaction solution, generate tabular zinc glycinate crystal.Specifically comprise the following steps:
Step 1, takes a certain amount of soluble zinc salt, joins in deionized water, through stirring, forms the zinc salt solution that volumetric molar concentration is 0.5～3.0mol/L; Take a certain amount of glycine, join in deionized water, through stirring, form the glycine solution that volumetric molar concentration is 0.5～3.0mol/L; Take a certain amount of sodium hydroxide, join in deionized water, through stirring, form the aqueous sodium hydroxide solution that volumetric molar concentration is 0.5～2.0mol/L.Preferably, described zinc salt is selected from one or more in zinc sulfate, zinc chloride and zinc acetate.
Step 2, pours zinc salt solution and aqueous sodium hydroxide solution respectively in two separating funnels, is added drop-wise in glycine solution simultaneously.Adjust the rate of addition of hydrogen aqueous sodium hydroxide solution, the pH value of controlling reaction soln is 5～7, and reaction obtains white precipitate, is deposited in ageing 8h～15h in reaction soln, preferably 12h.
Step 3, by the white precipitate precipitation vacuum pump using circulatory water suction filtration of step 2 gained, being deposited at 50～80 ℃ of obtaining is dried 4～10h, obtains zinc glycinate inner complex solid.
Zinc glycinate inner complex prepared by the present invention can be used for adding of trace element zinc in fodder additives.
Utilize the preparation method of zinc glycinate inner complex of the present invention, because reaction is to be carried out in the aqueous solution by soluble zinc salt and glycine, there is speed of response fast, the feature that product purity is high.Meanwhile, present method can be carried out at normal temperatures, has advantages of that power consumption is low.In addition the zinc glycinate that, adopts present method to prepare presents tabular geometric shape.In addition, the plant and instrument using due to the preparation method of a kind of zinc glycinate inner complex of the present invention is simple, and technological process is simple and process tolerant is wide, thereby is conducive to realize scale operation.
Accompanying drawing explanation
Fig. 1 is X-ray diffraction (XRD) figure of the zinc glycinate inner complex of preparation in embodiment 1;
Fig. 2 is scanning electronic microscope (SEM) picture of the zinc glycinate inner complex of preparation in embodiment 1.
Embodiment
Below in conjunction with accompanying drawing, principle of the present invention and feature are described, example, only for explaining the present invention, is not intended to limit scope of the present invention.
The present invention's zinc salt, glycine and sodium hydroxide used is purchased from Shanghai reagent company of traditional Chinese medicines group, and reagent is analytical pure.
The model of the instrument that the present invention is used, specification, the information such as manufacturer are as shown in table 1.
The model of table 1 instrument of the present invention, specification, manufacturer
Embodiment 1
(1), take the ZnSO of 13.9g
47H
2o, joins in 25ml deionized water, through stirring, forms the ZnSO that volumetric molar concentration is 2.0mol/L
4the aqueous solution; Take the glycine of 7.5g, join in 50ml ionized water, through stirring, form the glycine solution that volumetric molar concentration is 2.0mol/L; Take the sodium hydroxide of 4g, join in 100ml deionized water, through stirring, form the aqueous sodium hydroxide solution that volumetric molar concentration is 1.0mol/L.
(2), by ZnSO
4the aqueous solution and aqueous sodium hydroxide solution are poured into respectively in two separating funnels, be added drop-wise in glycine solution simultaneously, regulating the titration speed of zinc solution and sodium hydroxide solution is 5ml/min, and the pH value of controlling reaction soln is 6.0, and the zinc salt entering and the mol ratio of glycine are 2:1.Reaction obtains white precipitate, is deposited in ageing 12h in mother liquor.
(3), by the white precipitate vacuum pump using circulatory water suction filtration of step (2) gained, what obtain is deposited at 80 ℃ dry 6h, obtains zinc glycinate inner complex solid.
The X-ray diffraction of gained zinc glycinate (XRD) collection of illustrative plates as shown in Figure 1, is that 11.8 °, 20.2 ° and 22.5 ° etc. locate to occur sharp-pointed diffraction peak at 2 θ angles, illustrates that the crystallization degree of gained zinc glycinate is higher.As shown in Figure 2, zinc glycinate presents tabular geometric shape to scanning electron microscope (SEM) photograph.
Embodiment 2
(1), take the ZnSO of 13.9g
47H
2o, joins in 25ml deionized water, through stirring, forms the ZnSO that volumetric molar concentration is 2.0mol/L
4the aqueous solution; Take the glycine of 7.5g, join in 50ml ionized water, through stirring, form the glycine solution that volumetric molar concentration is 2.0mol/L; Take the sodium hydroxide of 4g, join in 100ml deionized water, through stirring, form the aqueous sodium hydroxide solution that volumetric molar concentration is 1.0mol/L.
(2), by ZnSO
4the aqueous solution and aqueous sodium hydroxide solution are poured into respectively in two separating funnels, be added drop-wise in glycine solution simultaneously, regulating the titration speed of zinc solution and sodium hydroxide solution is 5ml/min, and the pH value of controlling reaction soln is 5.0, and the zinc salt entering and the mol ratio of glycine are 2:1.Reaction obtains white precipitate, is deposited in ageing 8h in mother liquor.
(3), by the white precipitate vacuum pump using circulatory water suction filtration of step (2) gained, what obtain is deposited at 50 ℃ dry 10h, obtains zinc glycinate inner complex solid.
Embodiment 3
(1), take the ZnSO of 13.9g
47H
2o, joins in 25ml deionized water, through stirring, forms the ZnSO that volumetric molar concentration is 2.0mol/L
4the aqueous solution; Take the glycine of 7.5g, join in 50ml ionized water, through stirring, form the glycine solution that volumetric molar concentration is 2.0mol/L; Take the sodium hydroxide of 4g, join in 100ml deionized water, through stirring, form the aqueous sodium hydroxide solution that volumetric molar concentration is 1.0mol/L.
(2), the ZnSO4 aqueous solution and aqueous sodium hydroxide solution are poured into respectively in two separating funnels, be added drop-wise in glycine solution simultaneously, regulating the titration speed of zinc solution and sodium hydroxide solution is 5ml/min, and the pH value of controlling reaction soln is 5.5, the zinc salt entering and the mol ratio of glycine are 2:1.Reaction obtains white precipitate, is deposited in ageing 15h in mother liquor.
(3), by the white precipitate vacuum pump using circulatory water suction filtration of step (2) gained, what obtain is deposited at 80 ℃ dry 4h, obtains zinc glycinate inner complex solid.
Embodiment 4
(1), take the ZnSO of 13.9g
47H
2o, joins in 25ml deionized water, through stirring, forms the ZnSO that volumetric molar concentration is 2.0mol/L
4the aqueous solution; Take the glycine of 7.5g, join in 50ml ionized water, through stirring, form the glycine solution that volumetric molar concentration is 2.0mol/L; Take the sodium hydroxide of 4g, join in 100ml deionized water, through stirring, form the aqueous sodium hydroxide solution that volumetric molar concentration is 1.0mol/L.
(2), by ZnSO
4the aqueous solution and aqueous sodium hydroxide solution are poured into respectively in two separating funnels, be added drop-wise in glycine solution simultaneously, regulating the titration speed of zinc solution and sodium hydroxide solution is 5ml/min, and the pH value of controlling reaction soln is 6.5, and the zinc salt entering and the mol ratio of glycine are 2:1.Reaction obtains white precipitate, is deposited in ageing 10h in mother liquor.
(3), by the white precipitate vacuum pump using circulatory water suction filtration of step (2) gained, what obtain is deposited at 60 ℃ dry 8h, obtains zinc glycinate inner complex solid.
Embodiment 5
(1), take the ZnSO of 13.9g
47H
2o, joins in 25ml deionized water, through stirring, forms the ZnSO that volumetric molar concentration is 2.0mol/L
4the aqueous solution; Take the glycine of 7.5g, join in 50ml ionized water, through stirring, form the glycine solution that volumetric molar concentration is 2.0mol/L; Take the sodium hydroxide of 4g, join in 100ml deionized water, through stirring, form the aqueous sodium hydroxide solution that volumetric molar concentration is 1.0mol/L.
(2), by ZnSO
4the aqueous solution and aqueous sodium hydroxide solution are poured into respectively in two separating funnels, be added drop-wise in glycine solution simultaneously, regulating the titration speed of zinc solution and sodium hydroxide solution is 5ml/min, and the pH value of controlling reaction soln is 7.0, and the zinc salt entering and the mol ratio of glycine are 2:1.Reaction obtains white precipitate, is deposited in ageing 14h in mother liquor.
(3), by the white precipitate vacuum pump using circulatory water suction filtration of step (2) gained, what obtain is deposited at 70 ℃ dry 5h, obtains zinc glycinate inner complex solid.
The foregoing is only preferred embodiment of the present invention, in order to limit the present invention, within the spirit and principles in the present invention not all, any modification of doing, be equal to replacement, improvement etc., within all should being included in protection scope of the present invention.
Claims (6)
1. a preparation method for zinc glycinate inner complex, said method comprising the steps of:
Step 1, preparation zinc salt solution, glycine solution and aqueous sodium hydroxide solution;
Step 2, zinc salt solution and hydrogen aqueous sodium hydroxide solution are added drop-wise in glycine solution simultaneously, adjust the rate of addition of hydrogen aqueous sodium hydroxide solution, the pH value of controlling reaction soln is 5～7, reaction obtains white depositions, by white depositions ageing 8h～15h in reaction soln;
Step 3, carries out decompress filter and drying treatment by the mixture of the white depositions of step 2 gained and reaction soln formation, obtains tabular white crystal.
2. the preparation method of zinc glycinate inner complex according to claim 1, it is characterized in that, the concentration of zinc salt solution is 0.5～3.0mol/L, and the concentration of glycine solution is 0.5～3.0mol/L, and the concentration of aqueous sodium hydroxide solution is 0.5～2.0mol/L.
3. the preparation method of zinc glycinate inner complex according to claim 1, is characterized in that, in step 1, described zinc salt is selected from one or more in zinc sulfate, zinc chloride and zinc acetate.
4. the preparation method of zinc glycinate inner complex according to claim 1, is characterized in that, in step 2, the zinc salt adding and the mol ratio of glycine are 2:1.
5. the preparation method of zinc glycinate inner complex according to claim 1, is characterized in that, in step 2, white depositions is ageing 12h in reaction soln.
6. the preparation method of zinc glycinate inner complex according to claim 1, is characterized in that, in step 3, is deposited in dry 4h～10h at 50 ℃～80 ℃ described in inciting somebody to action.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410131404.4A CN103922954A (en) | 2014-04-02 | 2014-04-02 | Method for preparing glycine zinc chelate |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410131404.4A CN103922954A (en) | 2014-04-02 | 2014-04-02 | Method for preparing glycine zinc chelate |
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| CN201410131404.4A Pending CN103922954A (en) | 2014-04-02 | 2014-04-02 | Method for preparing glycine zinc chelate |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106928085A (en) * | 2017-01-22 | 2017-07-07 | 陕西师范大学 | A kind of L theanine chelates of zinc and preparation method and tea beverage and preparation method containing the chelate |
| CN107098770A (en) * | 2017-06-26 | 2017-08-29 | 福州大学化肥催化剂国家工程研究中心 | A kind of chelating amino acids zinc fertilizer and preparation method thereof |
| CN107652196A (en) * | 2017-10-20 | 2018-02-02 | 衡阳德邦新金生物科技有限公司 | A kind of removal technique of the glycine zine crystallization water |
| CN110041215A (en) * | 2019-05-09 | 2019-07-23 | 河北力维素科技有限公司 | A kind of preparation method of food-grade glycine zine chelate |
| CN110330439A (en) * | 2019-07-12 | 2019-10-15 | 辽阳华路催化技术研发有限公司 | A kind of zinc-glycine complex and preparation method thereof not introducing foreign ion |
| CN115160168A (en) * | 2022-08-11 | 2022-10-11 | 长沙兴嘉生物工程股份有限公司 | Zinc glycinate crystal and preparation method and application thereof |
| CN115819263A (en) * | 2022-12-07 | 2023-03-21 | 贵州大学 | A kind of organic zinc selenium chelate, functional fertilizer, and its preparation method and application |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106928085A (en) * | 2017-01-22 | 2017-07-07 | 陕西师范大学 | A kind of L theanine chelates of zinc and preparation method and tea beverage and preparation method containing the chelate |
| CN107098770A (en) * | 2017-06-26 | 2017-08-29 | 福州大学化肥催化剂国家工程研究中心 | A kind of chelating amino acids zinc fertilizer and preparation method thereof |
| CN107652196A (en) * | 2017-10-20 | 2018-02-02 | 衡阳德邦新金生物科技有限公司 | A kind of removal technique of the glycine zine crystallization water |
| CN110041215A (en) * | 2019-05-09 | 2019-07-23 | 河北力维素科技有限公司 | A kind of preparation method of food-grade glycine zine chelate |
| CN110330439A (en) * | 2019-07-12 | 2019-10-15 | 辽阳华路催化技术研发有限公司 | A kind of zinc-glycine complex and preparation method thereof not introducing foreign ion |
| CN115160168A (en) * | 2022-08-11 | 2022-10-11 | 长沙兴嘉生物工程股份有限公司 | Zinc glycinate crystal and preparation method and application thereof |
| CN115819263A (en) * | 2022-12-07 | 2023-03-21 | 贵州大学 | A kind of organic zinc selenium chelate, functional fertilizer, and its preparation method and application |
| CN115819263B (en) * | 2022-12-07 | 2024-10-11 | 贵州大学 | Organic zinc selenium chelate, functional fertilizer, and preparation method and application thereof |
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