CN107445868A - N carbamylglutamic acid Chelated Manganeses and preparation method thereof - Google Patents
N carbamylglutamic acid Chelated Manganeses and preparation method thereof Download PDFInfo
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- CN107445868A CN107445868A CN201710664689.1A CN201710664689A CN107445868A CN 107445868 A CN107445868 A CN 107445868A CN 201710664689 A CN201710664689 A CN 201710664689A CN 107445868 A CN107445868 A CN 107445868A
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- manganese
- carbamylglutamic
- acids
- carbamylglutamic acids
- bivalent compound
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- LCQLHJZYVOQKHU-VKHMYHEASA-N carglumic acid Chemical compound NC(=O)N[C@H](C(O)=O)CCC(O)=O LCQLHJZYVOQKHU-VKHMYHEASA-N 0.000 title claims abstract description 72
- 235000002908 manganese Nutrition 0.000 title claims abstract description 71
- 238000002360 preparation method Methods 0.000 title description 11
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 59
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 52
- 239000011572 manganese Substances 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 20
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910001947 lithium oxide Inorganic materials 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 229910021380 Manganese Chloride Inorganic materials 0.000 claims description 17
- 239000011565 manganese chloride Substances 0.000 claims description 17
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 claims description 16
- 235000002867 manganese chloride Nutrition 0.000 claims description 16
- 229940099607 manganese chloride Drugs 0.000 claims description 16
- 229940071125 manganese acetate Drugs 0.000 claims description 10
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
- -1 acyl glutamic acid Chemical compound 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 229940099596 manganese sulfate Drugs 0.000 claims description 6
- 235000007079 manganese sulphate Nutrition 0.000 claims description 6
- 239000011702 manganese sulphate Substances 0.000 claims description 6
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 6
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 239000002736 nonionic surfactant Substances 0.000 claims description 5
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004220 glutamic acid Substances 0.000 claims description 3
- 235000013922 glutamic acid Nutrition 0.000 claims description 3
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 150000002696 manganese Chemical class 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 150000007513 acids Chemical class 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 238000003756 stirring Methods 0.000 description 11
- 238000005457 optimization Methods 0.000 description 10
- 235000001014 amino acid Nutrition 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 239000013522 chelant Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
- 235000016709 nutrition Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000035764 nutrition Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000004475 Arginine Substances 0.000 description 2
- 241000040710 Chela Species 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 235000013619 trace mineral Nutrition 0.000 description 2
- 239000011573 trace mineral Substances 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
- RFMMMVDNIPUKGG-YFKPBYRVSA-N N-acetyl-L-glutamic acid Chemical compound CC(=O)N[C@H](C(O)=O)CCC(O)=O RFMMMVDNIPUKGG-YFKPBYRVSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000019728 animal nutrition Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 238000000205 computational method Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003248 enzyme activator Substances 0.000 description 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- ZHUXMBYIONRQQX-UHFFFAOYSA-N hydroxidodioxidocarbon(.) Chemical group [O]C(O)=O ZHUXMBYIONRQQX-UHFFFAOYSA-N 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910001437 manganese ion Inorganic materials 0.000 description 1
- KNLQKHUBPCXPQD-UHFFFAOYSA-N manganese;sulfuric acid Chemical compound [Mn].OS(O)(=O)=O KNLQKHUBPCXPQD-UHFFFAOYSA-N 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/16—Inorganic salts, minerals or trace elements
- A23L33/165—Complexes or chelates
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/17—Amino acids, peptides or proteins
- A23L33/175—Amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/16—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by carboxyl groups
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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Abstract
The invention discloses a kind of method for preparing N carbamylglutamic acid Chelated Manganeses, comprise the following steps：(1) it is N carbamylglutamic acids, lithia or/and lithium hydroxide is soluble in water, it is well mixed, obtains N carbamylglutamic acids chelating lithium solution；(2) bivalent compound of manganese is added into step (1) resulting solution, after being well mixed, is reacted at 60~80 DEG C, obtains N carbamylglutamic acid Chelated Manganeses；Products therefrom is through examining, and manganese content can reach 17.29%, and carbamylglutamic acid containing N can reach 61.21%.N carbamylglutamic acid Chelated Manganeses are prepared by the method for the present invention, reaction condition is gentle, and reaction is easy, the cycle is short, and yield is high, and production cost is relatively low, and product characteristicses are stable, and purity is high (can reach 98%).
Description
Technical field
The present invention relates to a kind of preparation method of organic chelate, especially N- carbamylglutamic acids Chelated Manganese and its preparation
Method.
Background technology
Manganese is one of essential trace element of animal, the composition of many enzymes or albumen in organism is participated in, such as super oxygen
Thing mutase (SOD) etc., and in body important enzyme activator, participate in generation of body carbohydrate, fat and protein
Thank, played an important role in immunity of organism, the formation of bone and cerebral function etc..Life occurs in animal manganese deficiency
The symptoms such as length is obstructed, reproductive performance declines, skeleton development is obstructed.At present, in animal and fowl fodder, most-often used is inorganic sulfuric acid
Manganese.In Modern Animal Husbandry production, it has been recognized that relatively low utilization rate, easy moisture absorption caking, Oxidative demage be present in inorganic manganese
The problems such as vitamin in feed, to improve manganese element biology utilization rate, reduce manganese element in diet and drained with excrement to ring
The pollution in border, develop and added using chemical property stabilization, the new Organic Manganese high with internal existence form convergence, absorption rate
Add agent, it has also become the focus of manganese element nutrient research.Wherein, chelating amino acids manganese have improve manganese ion absorption in vivo and
Using, chemical stability is good, palatability is good the advantages that, be the effective way for preparing the feed containing manganese.N- carbamylglutamic acids are made
It is a kind of green, efficient functional amino accelerator for arginic endogenous activator, while is also that a kind of nutrition is strong
Agent or health products, Lean mass can be dramatically increased.Therefore, design has strong with synthesis N- carbamylglutamic acids Chelated Manganese
Big potentiality value, can be used as functional drug, food additives or feed addictive.
In place of the method Shortcomings of the existing amino acid trace element chelated manganese of production, such as：1. existing chelating amino acids
The part of manganese is substantially all the simple amino acid for glycine etc, without function affect；2. by metal manganese source directly with
Amino acid reaction, chelate effect is poor, will be with the presence of substantial amounts of free metal amino acid and metal ion in product.It is in addition, existing
N- carbamyls-Pidolidone manganese complex technology of preparing low yield, product purity is not high, contains more free manganese element.
The content of the invention
Based on this, a kind of feature amino is provided it is an object of the invention to overcome above-mentioned the deficiencies in the prior art part
The preparation method of sour accelerator, this method reaction condition is gentle, and reaction is easy, the cycle is short, and yield is high, and production cost is relatively low, production
Physical property matter is stable, and purity is high (can reach 98%).
To achieve the above object, the technical scheme taken of the present invention is：A kind of N- carbamylglutamic acid Chelated Manganeses of preparing
Method, comprise the following steps：(1) it is N- carbamylglutamic acids, lithia or/and lithium hydroxide is soluble in water, it is well mixed, obtains
Lithium solution is chelated to N- carbamylglutamic acids；(2) bivalent compound of manganese is added into step (1) resulting solution, is well mixed
Afterwards, reacted at 60~80 DEG C, obtain described N- carbamylglutamic acid Chelated Manganeses.
It should be noted that N- carbamylglutamic acids (Arginine activator additive, AAA) are N- acetyl
The analog of glutamic acid (N-acetylglutamate, NAG), can be with Effective Regulation as a kind of new functional amino
Endogenous arginine synthesizes, and then promotes growth of animal performance.
As the further optimization to above-mentioned technical proposal, methods described also includes step (3)：It is molten to step (2) gained
Nonionic surfactant is added in liquid, constant temperature is stirred and adds ethanol, and 10~30min of constant temperature, natural cooling, is obtained at room temperature
Crystallized to N- carbamylglutamic acids Chelated Manganese.
As the further optimization to above-mentioned technical proposal, the bivalent compound of manganese described in step (2) is the oxidation of manganese
Thing, hydroxide or inorganic manganese salt.
As the further optimization to above-mentioned technical proposal, the bivalent compound of manganese described in step (2) is manganese chloride, sulphur
At least one of sour manganese, manganese acetate.
As the further optimization to above-mentioned technical proposal, the bivalent compound of the manganese is manganese chloride, manganese sulfate or
The mol ratio of manganese acetate, the N- carbamylglutamic acids and manganese chloride, manganese sulfate or manganese acetate is 0.93~1.48:1.
As the further optimization to above-mentioned technical proposal, the bivalent compound of the manganese is manganese chloride, the N- ammonia first
The mol ratio of acyl glutamic acid and manganese chloride is 1:1.Present inventor has found through many experiments, when N- carbamylglutamic acids with
The mol ratio of manganese chloride is 1:When 1, the yield of N- carbamylglutamic acid Chelated Manganeses is obviously improved.
As the further optimization to above-mentioned technical proposal, N- carbamylglutamic acids described in step (1) and lithia or/
Mol ratio with elemental lithium in lithium hydroxide is 1:0.85~1.2.
As the further optimization to above-mentioned technical proposal, the reaction time is 1.5~2h in the step (2).
As the further optimization to above-mentioned technical proposal, nonionic surfactant is polyoxy second in the step (3)
Alkene octyl phenol ether 10 or polyoxyethylene sorbitan monoleate.
As the further optimization to above-mentioned technical proposal, in the step (2), 1.5~2h is reacted at 60~80 DEG C
Afterwards, add the solution of manganese chloride, manganese sulfate or manganese acetate through cooling down, filter, dry after obtain described N- carbamyl paddy ammonia
Sour Chelated Manganese.
As another aspect of the present invention, present invention also offers one kind to use N- carbamyls paddy ammonia made from the above method
Sour Chelated Manganese.
As the further optimization to above-mentioned technical proposal, the quality percentage of manganese in the N- carbamylglutamic acids Chelated Manganese
Content is that the weight/mass percentage composition of 17.29%, N- carbamylglutamic acids is 61.21%.
In summary, beneficial effects of the present invention are：
1st, because N- carbamylglutamic acids are a kind of functional aminos, its introducing had both added the nutrition work(of chelate
Can, be advantageous to environmental protection again；
2nd, because the N- carbamylglutamic acid Chelated Manganeses of the present invention are a kind of chelates using manganese element as part center, because
This has good stability；
3rd, N- carbamylglutamic acids have synergy with manganese, and this improves the bioavailability of manganese element；
4th, N- carbamylglutamic acids Chelated Manganese has good dissolubility energy, and its preparation is easy to dissolve, reduce cost and
Toxicity.
Brief description of the drawings
Fig. 1 is the infrared spectrogram of N- carbamylglutamic acid Chelated Manganeses made from the method for the present invention；
Wherein, 1, N- carbamylglutamic acids, 2, N- carbamylglutamic acid Chelated Manganeses；
The O-H keys in N- carbamylglutamic acids carboxyl are in 2544cm as shown in Figure 1-1Nearby with the presence of wide distribution of peaks, and it is somebody's turn to do
Peak is disappeared in the infrared spectrum of chelate, and the H in O-H on this explanation N- carbamylglutamic acid carboxyl is substituted, carboxyl oxygen
Atom is sloughed hydrogen atom and is coordinated with manganese.
Embodiment
The present invention is used as part using functional amino accelerant N-carbamylglutamic acid, by N- carbamylglutamic acids and
Elemental lithium in molar ratio 1:0.85~1.2 adds lithia or/and lithium hydroxide, stirs 20~30min, obtains colorless and clear liquid
Body；Then, by manganese chloride, manganese sulfate or manganese acetate and N- carbamylglutamic acids in molar ratio 1：0.93~1.48 addition is colourless
In supernatant liquid, 1.5~2h is stirred at 60~80 DEG C, obtains clear liquid, cold filtration, filtrate is N- carbamylglutamic acid chelas
Manganese solution is closed, 0.15~0.50ml nonionic surfactants are added into the N- carbamylglutamic acids chelating manganese solution of heat, it is permanent
Temperature 12~30min of stirring, is slowly added into 10~50ml ethanol, is incubated 10~28min, natural cooling obtains N- ammonia first at room temperature
Acyl glutamate chelate manganese crystallizes.
To better illustrate the object, technical solutions and advantages of the present invention, below in conjunction with the drawings and specific embodiments pair
The present invention is described further.
Embodiment 1
A kind of embodiment of the N- carbamylglutamic acid Chelated Manganeses of the present invention, the preparation of the N- carbamylglutamic acid Chelated Manganeses
Method comprises the following steps：
(1) it is N- carbamylglutamic acids is soluble in water, by N- carbamylglutamic acids and elemental lithium mol ratio 1:0.85 adds
Lithia, stir 20min；
(2) manganese oxide is added into step (1) resulting solution, is heated to 80 DEG C, kept constant temperature, at the uniform velocity stir, reacted
1.5h, obtain N- carbamylglutamic acids chelating manganese solution；
(3) 0.15ml polyoxethylene octylphenyls phenol ether 10,80 DEG C of stirrings of constant temperature are added into hot solution obtained by step (2)
30min, 50ml ethanol is slowly added into, is incubated 28min, natural cooling obtains N- carbamylglutamic acid Chelated Manganese knots at room temperature
It is brilliant；Through chemical examination, its (mass fraction) containing manganese 17.29%, carbamylglutamic acid containing N- 61.21% (mass fraction), its infrared light
Spectrogram is as shown in Figure 1.
Wherein, the mol ratio of N- carbamylglutamic acids and manganese oxide is 0.93:1；The quality of N- carbamylglutamic acids and water
Volume ratio is 1g：3.5ml.
Embodiment 2
A kind of embodiment of the N- carbamylglutamic acid manganese complexs of the present invention, chemical formula C6H10N2O5MnCl2, the N-
The preparation method of carbamylglutamic acid manganese complex comprises the following steps：
(1) it is N- carbamylglutamic acids is soluble in water, by N- carbamylglutamic acids and elemental lithium mol ratio 1:1 adds hydrogen-oxygen
Change lithium, stir 30min；(2) manganese chloride is added into step (1) resulting solution, is heated to 71 DEG C, kept constant temperature, at the uniform velocity stir,
React 1.8h；(3) 0.30ml polyoxyethylene sorbitan monoleates are added into hot solution obtained by step (2), 71 DEG C of constant temperature stirs 21min, slowly
40ml ethanol is added, is incubated 19min, natural cooling obtains the crystallization of N- carbamylglutamic acids manganese, its infrared spectrogram at room temperature
As shown in Figure 1.
Wherein, the mol ratio of N- carbamylglutamic acids and manganese chloride is 1:1；The quality volume of N- carbamylglutamic acids and water
Than for 1g：4.3ml.
Embodiment 3
A kind of embodiment of the N- carbamylglutamic acid manganese complexs of the present invention, the N- carbamylglutamic acid manganese complexs
Preparation method comprises the following steps：
(1) it is N- carbamylglutamic acids is soluble in water, by N- carbamylglutamic acids and elemental lithium mol ratio 1:1.2 add oxygen
Change lithium, stir 25min；
(2) manganese acetate is added into step (1) resulting solution, is heated to 60 DEG C, kept constant temperature, at the uniform velocity stir, reacted
2.0h, (3) add 0.50ml polyoxyethylene sorbitan monoleates into step (2) gained hot solution, 60 DEG C of stirring 12min of constant temperature, are slowly added into
10ml ethanol, 10min is incubated, natural cooling obtains the crystallization of N- carbamylglutamic acids manganese, its infrared spectrogram such as Fig. 1 at room temperature
It is shown,
Wherein, the mol ratio of N- carbamylglutamic acids and manganese acetate is 1.48:1；The quality of N- carbamylglutamic acids and water
Volume ratio is 1g：4.9ml.
Shadow of the mol ratio of embodiment 4N- carbamylglutamic acids and manganese element to the yield of N- carbamylglutamic acid Chelated Manganeses
Ring
N- carbamylglutamic acid Chelated Manganeses, as a control group, preparation method and reality are prepared using the preparation method of embodiment 2
It is consistent to apply example 2, differ only in N- carbamylglutamic acids and manganese mol ratio and manganese classes of compounds it is different, then calculate N-
The yield of carbamylglutamic acid Chelated Manganese, the computational methods of the yield are：The N- carbamylglutamic acids of yield=100% × acquisition
Chelated Manganese mole amount/input water in N- carbamylglutamic acids mole amount.The production of N- carbamylglutamic acid Chelated Manganeses
Rate is as shown in table 1 below.
The yield of table 1N- carbamylglutamic acid Chelated Manganeses
As shown in Table 1, when the mol ratio of N- carbamylglutamic acids and manganese chloride is 1:When 1, N- carbamylglutamic acid chelas
The yield highest (close with control group 5) of manganese is closed, and the yield substantially than control group 1,2,3,4,6 and 7 is high.
The Animal nutrition experiment of the N- carbamylglutamic acids Chelated Manganese produced by the present invention of embodiment 5
N- carbamylglutamic acids Chelated Manganese made from 1-3 of the embodiment of the present invention is carried out in the SD rats of 33-61 ages in days
Nutritional test, 10mg/kg (according to American Nutrition Society's AIN-93 standards) is added in rat daily ration, application effect see the table below 2.
Table 2N- carbamylglutamic acids are complexed the effectiveness of manganese
Experimental result (being shown in Table 2) shows that N- carbamylglutamic acids Chelated Manganese can effectively facilitate the growth of SD rats, and
Effect is better than inorganic manganese.
Finally, it should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention rather than the present invention is protected
The limitation of scope is protected, although being explained in detail with reference to preferred embodiment to the present invention, one of ordinary skill in the art should
Understand, technical scheme can be modified or equivalent substitution, without departing from the essence of technical solution of the present invention
And scope.
Claims (10)
- A kind of 1. method for preparing N- carbamylglutamic acid Chelated Manganeses, it is characterised in that comprise the following steps：(1) it is N- carbamylglutamic acids, lithia or/and lithium hydroxide is soluble in water, it is well mixed, obtains N- carbamyl paddy ammonia Acid chelating lithium solution；(2) bivalent compound of manganese is added into step (1) resulting solution, after being well mixed, reacts, obtains at 60~80 DEG C Described N- carbamylglutamic acids chelating manganese solution.
- 2. the method as described in claim 1, it is characterised in that methods described also includes step (3)：It is molten to step (2) gained Nonionic surfactant is added in liquid, constant temperature is stirred and adds ethanol, and 10~30min of constant temperature, natural cooling, is obtained at room temperature Crystallized to N- carbamylglutamic acids Chelated Manganese.
- 3. the method as described in claim 1, it is characterised in that the bivalent compound of manganese described in step (2) is the oxidation of manganese Thing, hydroxide or inorganic manganese salt.
- 4. the method as described in claim 1, it is characterised in that the bivalent compound of manganese described in step (2) is manganese chloride, sulphur At least one of sour manganese, manganese acetate.
- 5. the method as described in claim 1, it is characterised in that the bivalent compound of the manganese be manganese chloride, manganese sulfate or The mol ratio of manganese acetate, the N- carbamylglutamic acids and manganese chloride, manganese sulfate or manganese acetate is 0.93~1.48:1.
- 6. method as claimed in claim 5, it is characterised in that the bivalent compound of the manganese is manganese chloride, the N- ammonia first The mol ratio of acyl glutamic acid and manganese chloride is 1:1.
- 7. the method as described in claim 1, it is characterised in that N- carbamylglutamic acids described in step (1) and lithia or/ Mol ratio with elemental lithium in lithium hydroxide is 1:0.85~1.2.
- 8. the method as described in claim 1, it is characterised in that the reaction time is 1.5~2h in the step (2).
- 9. method as claimed in claim 2, it is characterised in that nonionic surfactant is polyoxy second in the step (3) Alkene octyl phenol ether 10 or polyoxyethylene sorbitan monoleate.
- 10.N- carbamylglutamic acid Chelated Manganeses, it is characterised in that the N- carbamylglutamic acids manganese uses such as claim 1~9 Method described in any one is made.
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|---|---|---|---|---|
| GB1182815A (en) * | 1967-06-13 | 1970-03-04 | Prodotti Antibiotici Spa | New Salts of N-Carbamyl-Glutamic Acid and of N-Carbamyl-Aspartic Acid. |
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| GB1182815A (en) * | 1967-06-13 | 1970-03-04 | Prodotti Antibiotici Spa | New Salts of N-Carbamyl-Glutamic Acid and of N-Carbamyl-Aspartic Acid. |
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