CN112724032A - Threonine calcium product and production method thereof - Google Patents
Threonine calcium product and production method thereof Download PDFInfo
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- CN112724032A CN112724032A CN202011583940.XA CN202011583940A CN112724032A CN 112724032 A CN112724032 A CN 112724032A CN 202011583940 A CN202011583940 A CN 202011583940A CN 112724032 A CN112724032 A CN 112724032A
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- threonine
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title claims abstract description 102
- 239000011575 calcium Substances 0.000 title claims abstract description 101
- 229910052791 calcium Inorganic materials 0.000 title claims abstract description 101
- 239000004473 Threonine Substances 0.000 title claims abstract description 96
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 title claims abstract description 85
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims abstract description 107
- 229960002898 threonine Drugs 0.000 claims abstract description 95
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- 239000000047 product Substances 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000003756 stirring Methods 0.000 claims abstract description 19
- 238000001914 filtration Methods 0.000 claims abstract description 18
- 239000002994 raw material Substances 0.000 claims abstract description 11
- 238000001694 spray drying Methods 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 9
- 238000002425 crystallisation Methods 0.000 claims abstract description 8
- 239000000706 filtrate Substances 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 230000009920 chelation Effects 0.000 claims description 42
- 239000000376 reactant Substances 0.000 claims description 24
- 239000013078 crystal Substances 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 11
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000292 calcium oxide Substances 0.000 claims description 9
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 9
- 230000035484 reaction time Effects 0.000 claims description 9
- 238000001704 evaporation Methods 0.000 claims description 8
- 239000012528 membrane Substances 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 6
- 239000012065 filter cake Substances 0.000 claims description 6
- 230000008020 evaporation Effects 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 9
- 238000009776 industrial production Methods 0.000 abstract description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 3
- 239000011707 mineral Substances 0.000 abstract description 3
- 230000001502 supplementing effect Effects 0.000 abstract description 3
- 229960005069 calcium Drugs 0.000 description 77
- 239000000243 solution Substances 0.000 description 31
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 28
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 27
- 229960001484 edetic acid Drugs 0.000 description 27
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 19
- 229910001424 calcium ion Inorganic materials 0.000 description 19
- 229940024606 amino acid Drugs 0.000 description 18
- 150000001413 amino acids Chemical class 0.000 description 18
- 229910000019 calcium carbonate Inorganic materials 0.000 description 14
- 229960003563 calcium carbonate Drugs 0.000 description 14
- 238000012360 testing method Methods 0.000 description 12
- 230000029087 digestion Effects 0.000 description 8
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 8
- 239000013522 chelant Substances 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 238000000502 dialysis Methods 0.000 description 7
- 210000001035 gastrointestinal tract Anatomy 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 101001018064 Homo sapiens Lysosomal-trafficking regulator Proteins 0.000 description 4
- 102100033472 Lysosomal-trafficking regulator Human genes 0.000 description 4
- 235000010703 Modiola caroliniana Nutrition 0.000 description 4
- 244000038561 Modiola caroliniana Species 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 4
- 239000004312 hexamethylene tetramine Substances 0.000 description 4
- 210000004379 membrane Anatomy 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 159000000007 calcium salts Chemical class 0.000 description 3
- 229940038879 chelated zinc Drugs 0.000 description 3
- 238000010668 complexation reaction Methods 0.000 description 3
- 238000003926 complexometric titration Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- -1 hydrogen ions Chemical class 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 230000000968 intestinal effect Effects 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 229940055695 pancreatin Drugs 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 108010019160 Pancreatin Proteins 0.000 description 2
- 102000057297 Pepsin A Human genes 0.000 description 2
- 108090000284 Pepsin A Proteins 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 229940069978 calcium supplement Drugs 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 235000015872 dietary supplement Nutrition 0.000 description 2
- 238000004134 energy conservation Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229940111202 pepsin Drugs 0.000 description 2
- 229940068041 phytic acid Drugs 0.000 description 2
- 239000000467 phytic acid Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 230000009919 sequestration Effects 0.000 description 2
- 239000013589 supplement Substances 0.000 description 2
- 239000011573 trace mineral Substances 0.000 description 2
- 235000013619 trace mineral Nutrition 0.000 description 2
- ORZHVTYKPFFVMG-UHFFFAOYSA-N xylenol orange Chemical compound OC(=O)CN(CC(O)=O)CC1=C(O)C(C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C=C(CN(CC(O)=O)CC(O)=O)C(O)=C(C)C=2)=C1 ORZHVTYKPFFVMG-UHFFFAOYSA-N 0.000 description 2
- 108010011619 6-Phytase Proteins 0.000 description 1
- OPSXJNAGCGVGOG-DKWTVANSSA-L Calcium L-aspartate Chemical compound [Ca+2].[O-]C(=O)[C@@H](N)CC([O-])=O OPSXJNAGCGVGOG-DKWTVANSSA-L 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
- 239000001354 calcium citrate Substances 0.000 description 1
- 229960004256 calcium citrate Drugs 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000004227 calcium gluconate Substances 0.000 description 1
- 229960004494 calcium gluconate Drugs 0.000 description 1
- 235000013927 calcium gluconate Nutrition 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- NEEHYRZPVYRGPP-UHFFFAOYSA-L calcium;2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Ca+2].OCC(O)C(O)C(O)C(O)C([O-])=O.OCC(O)C(O)C(O)C(O)C([O-])=O NEEHYRZPVYRGPP-UHFFFAOYSA-L 0.000 description 1
- OFNJDDJDXNMTHZ-UHFFFAOYSA-L calcium;2-aminoacetate Chemical compound [Ca+2].NCC([O-])=O.NCC([O-])=O OFNJDDJDXNMTHZ-UHFFFAOYSA-L 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- WPEXVRDUEAJUGY-UHFFFAOYSA-B hexacalcium;(2,3,4,5,6-pentaphosphonatooxycyclohexyl) phosphate Chemical compound [Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])(=O)OC1C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C1OP([O-])([O-])=O WPEXVRDUEAJUGY-UHFFFAOYSA-B 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002366 mineral element Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229940085127 phytase Drugs 0.000 description 1
- 235000002949 phytic acid Nutrition 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/76—Metal complexes of amino carboxylic acids
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
- C07C227/42—Crystallisation
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- 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 threonine calcium product and a production method thereof, and the threonine calcium product is prepared by the following steps: (1) putting a certain amount of water into a reaction kettle, heating to 40-65 ℃, then putting the L-threonine and calcium raw materials in proportion, and stirring and mixing uniformly; (2) adjusting the pH and temperature of the solution, and carrying out synthetic reaction in a closed reaction kettle for a plurality of times; (3) after the synthesis reaction is finished, filtering for later use; (4) and (3) treating the filtrate by adopting a spray drying method or a crystallization method to prepare a threonine calcium product. The production method of the threonine calcium product has simple process, and the produced product has stable property and is suitable for industrial production. The prepared threonine calcium product can achieve the aim of balancing and supplementing mineral substances.
Description
Technical Field
The invention belongs to the technical field of amino acid microelement chelates, and particularly relates to a threonine calcium product and a production method thereof.
Background
Calcium plays an extremely important role in human metabolism and is an essential element in our life. At present, common calcium supplement products comprise calcium carbonate, calcium citrate, calcium gluconate, calcium glycinate, calcium L-aspartate and the like. The amino acid microelement chelate is a third-generation microelement supplement, is a chelate with a ring structure, integrates amino acid and microelements, has good stability and solubility in a pH environment in vivo, has absorption rate more than three times higher than that of inorganic salt, and has higher biological potency. Has good biochemical stability, and greatly reduces the antagonism between divalent metal ions in the digestive tract.
The amino acid calcium as a novel calcium nutrition enhancer can supplement the required amino acid while supplementing calcium, and the amino acid calcium can completely enter the blood plasma through small intestinal mucosa by utilizing the absorption channels of the amino acid and the small peptide and is transported to a target organ, so that oxalate, phosphate and the like in food are prevented from forming insoluble substances with calcium and being difficult to absorb, and the calcium supplement calcium has the advantages of good stability, high absorption and utilization rate and the like.
Disclosure of Invention
The invention aims to provide a production method of a threonine calcium product, which takes threonine and solid calcium salt as raw materials to synthesize an amino acid type mineral chelate, namely threonine calcium. The production process of the threonine calcium product is simple, and the obtained product has stable performance and is suitable for industrial production.
The purpose of the invention is realized by the following technical scheme:
the threonine calcium is prepared by preparing an aqueous solution from L-threonine and solid calcium salt according to a certain proportion, then carrying out synthetic reaction in a closed container, filtering, and carrying out spray drying or crystallization.
The invention provides a production method of a threonine calcium product, which comprises the following steps:
(1) putting a certain amount of water into a reaction kettle, heating to 40-65 ℃, then putting the L-threonine and calcium raw materials in proportion, and stirring and mixing uniformly;
(2) adjusting the pH and the temperature of the solution, and carrying out a synthesis reaction in the closed reaction kettle for a plurality of times;
(3) and after the synthesis reaction is finished, filtering for later use.
(4) And (3) treating the filtrate by adopting a spray drying method or a crystallization method to prepare a finished product of the threonine calcium.
Preferably, the calcium raw material comprises calcium oxide, calcium hydroxide, calcium sulfate, calcium chloride or calcium carbonate. Further preferably, the calcium raw material is one of calcium oxide, calcium carbonate, calcium sulfate, and calcium chloride.
Preferably, the mass ratio of the L-threonine to the calcium raw material in the step (1) is 190-210: 75-200% and the concentration of the reactant is 30-80%. Further preferably, the concentration of the reactant is 58-60%. The reactant concentration refers to the mass ratio of total reaction substrate to water.
Preferably, the temperature of the synthesis reaction in the step (3) is 45-90 ℃, the pH value is 6-10, and the reaction time is 1.5-4 h.
Preferably, the aperture of the filter membrane filtered in the step (3) is 0.1-0.45 mm. Further preferably, the pore size of the filter membrane filtered in the step (3) is 0.45 mm.
Preferably, the process for preparing the threonine calcium product by adopting the spray drying method in the step (4) comprises the following steps: atomizing the filtrate into 10-200 micron atomized particles through an atomizer, and directly contacting with hot air for heat exchange and drying to obtain threonine calcium solid powder.
Preferably, the spray drying method adopted in the step (4) has the following process conditions: the temperature of the air inlet is 150-300 ℃, the temperature of the air outlet is 50-150 ℃, and the feeding speed is 40-80 kg/h.
Preferably, the process for preparing the threonine calcium product by adopting the crystallization method in the step (4) comprises the following steps: evaporating and concentrating the filtrate until threonine calcium crystals are separated out, stopping concentrating, slowly cooling, filtering after a large amount of crystals are gradually separated out, and washing and drying the filter cake to obtain the threonine calcium crystals with uniform particles.
Preferably, the process conditions of the crystallization method adopted in the step (4) are as follows: the temperature of evaporation concentration is 40-90 ℃, the stirring speed is 10-25 r/min, and the temperature reduction gradient is 5-15 ℃/h.
The invention also provides a threonine calcium product prepared by the method.
The threonine calcium product prepared by the invention can be used as a food additive or a nutritional supplement and is widely applied to the fields of food, beverage, cosmetics, biomedicine, health care and the like.
Compared with the prior art, the invention has the following beneficial effects:
the invention synthesizes the calcium threonine chelate by using threonine and soluble calcium salt which have low market price and are essential amino acids for human bodies and animals as raw materials, has the advantages of high utilization rate of the raw materials, less loss, simple and easy operation process, energy conservation and environmental protection, and the prepared calcium threonine product has stable quality and high chelation rate, meets the requirement of food grade, and is suitable for industrial production.
The method adopted by the invention for preparing the threonine calcium product does not use any organic solvent, and compared with the traditional method for obtaining the final product by alcohol precipitation, the method realizes the purposes of energy conservation and environmental protection, and the final product has no residual alcohol substances and better meets the food-grade requirements.
The threonine calcium product prepared by the invention has good chemical and biochemical stability, good solubility in vivo, easy absorption, high bioavailability, no toxic or side effect, anti-interference performance, double functions of supplementing amino acid and mineral substances, can be used as a food additive or a nutritional supplement, and can be widely applied to the fields of food, beverage, cosmetics, biomedicine, health care and the like.
Drawings
FIG. 1 is a graph showing the effect of pH on threonine calcium chelation rate;
FIG. 2 is the effect of reaction temperature on threonine calcium chelation rate;
FIG. 3 is the effect of reaction time on threonine calcium chelation rate;
FIG. 4 is a graph of the effect of reactant concentration on threonine calcium chelation rate;
FIG. 5 is a graph showing the comparison of chelation rates of examples 1 to 4 in the present invention;
FIG. 6 is a graph showing a comparison of yields in examples 1 to 4 of the present invention;
FIG. 7 is an infrared spectrum of L-threonine;
FIG. 8 is an infrared spectrum of calcium threonine;
FIG. 9 is a graph showing a comparison of the solubility of calcium threonine and calcium carbonate to simulate different rates of sequestration following gastric digestion;
FIG. 10 is a graph showing a comparison of the dissolution rates of calcium threonine and calcium carbonate to simulate different rates of sequestration following intestinal digestion;
fig. 11 is a graph showing a comparison of the dialysance of calcium threonine and calcium carbonate to simulate different rates of chelation in the intestine.
Detailed Description
For a better understanding of the present invention, reference is made to the following examples. It is to be understood that these examples are for further illustration of the invention and are not intended to limit the scope of the invention. In addition, it should be understood that the invention is not limited to the above-described embodiments, but is capable of various modifications and changes within the scope of the invention.
Example 1
25kg of water is weighed into a reaction kettle, and 11.9kg of threonine is added while stirring after the temperature is raised to about 50 ℃. After the threonine solution is fully dissolved, 2.8kg of calcium oxide is added, the concentration of a reactant is controlled to be 58.8%, the temperature of the feed liquid is controlled to be about 80 ℃, the pH of the feed liquid is adjusted to be 8.5, after stirring and reaction are carried out for 3 hours, a 0.45mm membrane is adopted for filtration, and then spray drying is carried out to obtain the threonine calcium dry powder, wherein the set spray drying parameters are that the feed speed is 40kg/h, the rotating speed is 560r/min, the air inlet temperature is 200 ℃, and the air outlet temperature is 90 ℃.
Example 2
25kg of water is weighed into a reaction kettle, and 11.9kg of threonine is added while stirring after the temperature is raised to about 45 ℃. After the amino acid solution is fully dissolved, 2.8kg of calcium oxide is added, the concentration of a reactant is controlled to be 58.8%, the temperature of a feed liquid is controlled to be about 85 ℃, the pH value of the feed liquid is adjusted to be 8.0, after stirring and reacting for 2.5 hours, a 0.45mm membrane is adopted for filtering, and then spray drying is carried out to prepare the threonine calcium dry powder, wherein the set spray drying parameters are that the feed speed is 40kg/h, the rotating speed is 560r/min, the air inlet temperature is 200 ℃, and the air outlet temperature is 90 ℃.
Example 3
25kg of water is weighed into a reaction kettle, and 11.9kg of threonine is added while stirring after the temperature is raised to about 50 ℃. After threonine is fully dissolved, adding 2.8kg of calcium oxide, controlling the concentration of a reactant to be 58.8%, controlling the temperature of a feed liquid to be about 90 ℃, adjusting the pH of the feed liquid to be 8.5, stirring for reacting for 2 hours, filtering by using a 0.45mm membrane, then carrying out evaporation concentration, adjusting the temperature to be 60 ℃, stirring at a speed of 25r/min, reducing the temperature gradient to be 10 ℃/h, concentrating until crystals are separated out, stopping concentrating, slowly reducing the temperature at 10 ℃/h, filtering after a large amount of crystals are gradually separated out, washing and drying a filter cake, and obtaining the calcium threonine crystals with uniform particles.
Example 4
24.5kg of water is weighed into a reaction kettle, 11.9kg of threonine is added while stirring after the temperature is raised to about 50 ℃. After threonine is fully dissolved, 2.8kg of calcium oxide is added, the concentration of a reactant is controlled to be 60%, the temperature of a feed liquid is controlled to be about 80 ℃, the pH value of the feed liquid is adjusted to be 8, after stirring reaction is carried out for 2 hours, a 0.45mm0.45mm membrane is adopted for filtration and then evaporation concentration is carried out, the temperature is adjusted to be 60 ℃, the stirring speed is 25r/min, the temperature reduction gradient is 10 ℃/h, concentration is stopped when crystals are separated out, slow cooling is started at 10 ℃/h, after a large amount of crystals are gradually separated out, filtration is carried out, a filter cake is washed and dried, and the calcium threonine crystals with uniform particles can be obtained.
The chelating ratio of the calcium threonine crystals prepared in example 4 was 97.1%.
Test examples
Test example 1
This example illustrates screening of experimental conditions.
Weighing a certain amount of L-threonine in distilled water, heating in a water bath to about 60 ℃, adding calcium oxide, heating, stirring and reacting for a certain time until the feed liquid becomes clear. Filtering to remove insoluble substances, evaporating and concentrating the filtrate until crystals are separated out, stopping concentrating, slowly cooling, filtering after a large amount of crystals are gradually separated out, and washing and drying the filter cake to obtain the threonine calcium product. The factors influencing the amino acid trace element chelation reaction mainly comprise temperature, time, pH, reaction solution concentration and the like, and the influence of each factor on the chelation rate is respectively researched by taking the chelation rate as an index: regulating the reaction temperature to 80 ℃, controlling the concentration of reactants to be 60%, reacting for 2 hours under the conditions of different pH values, measuring the chelation rate, and analyzing the influence of the pH value. Adjusting the pH value of the solution to 7.5, adjusting the concentration of reactants to 60%, reacting for 2 hours at different temperatures, measuring the chelation rate, and analyzing the influence of the temperature. Regulating the pH value of the solution to 7.5, controlling the concentration of reactants to be 60%, reacting for different times at the temperature of 80 ℃, measuring the chelation rate, and analyzing the influence of the reaction time. Adjusting the temperature of the solution to 80 ℃, adjusting the pH value to 7.5, reacting for 2 hours under the conditions of different reactant concentrations, measuring the chelation rate, and analyzing the influence of the reactant concentrations.
(1) The chelation rate was determined as follows:
the calcium ion chelation rate is measured by EDTA complexation titration.
The method for processing the sample when the total calcium content is measured comprises the following steps: 5mL of threonine-calcium reaction solution is taken, and the volume of deionized water is adjusted to 50 mL.
The method for processing the sample during the determination of the calcium threonine content comprises the following steps: and adding 3 times of volume of absolute ethyl alcohol into another 5mL of reaction solution, fully and uniformly mixing, centrifuging at 10000r/min for 15min, removing supernatant, and fixing the volume of the precipitate to 50mL by using deionized water.
EDTA complexometric titration: and (3) taking 20mL of reaction liquid with constant volume, dropwise adding a xylenol orange indicator, dropwise adding 20% by mass of hexamethylenetetramine until the solution is in a stable mauve color, then adding 4mL of hexamethylenetetramine, titrating by using 0.01mol/L EDTA, and finally obtaining the end point when the solution is changed from the mauve color to yellow color.
In the formula, C: the concentration of EDTA solution, mol/L;
blank V: replacing the required volume of EDTA (ethylene diamine tetraacetic acid) of the solution to be detected by using deionized water, wherein the volume is mL;
v total: the total calcium content was measured as the volume of EDTA consumed at that time, mL;
v, chelation: the volume of EDTA (ethylene diamine tetraacetic acid) consumed in the determination of the content of the chelated calcium is mL;
the results are as follows:
the pH value is an important factor for forming the amino acid microelement chelate, hydrogen ions and metal ions compete for electron donating groups under the condition of low pH value, the formation of the amino acid microelement chelate is not facilitated, and hydroxyl groups and electron donating groups compete for metal ions to form hydroxide precipitates under the condition of high pH value. As can be seen from FIG. 1, at a lower pH, the chelating rate increases with an increase in pH, and after a pH of 7.5 is reached, the tendency of the chelating rate to increase is insignificant or even decreases, indicating that the chelating reaction is complete.
As can be seen from FIG. 2, the increase of the chelation rate with the increase of the temperature indicates that the chelation degree is continuously deepened, and the increase of the chelation rate is not obvious after the temperature is increased to 80 ℃, which indicates that 80 ℃ is the optimal reaction temperature. The chelating rate is increased slowly at 80 ℃, and is decreased slightly when the chelating rate is higher than 80 ℃, so that the chelating rate is maximum when the temperature is 80 ℃.
As can be seen from FIG. 3, the chelating rate increased with the increase of the reaction time, and the chelating rate did not increase significantly after the reaction time exceeded 2 hours, so that the chelating rate was the maximum at the reaction time of 2 hours.
The concentration of the reactant has a remarkable influence on the chelating rate of the amino acid trace elements. From the perspective of mass transfer, the concentration of reactants is an important influence factor in the chelation reaction process, and within a certain concentration range, the concentration of the reactants is small, the concentration of solute in a liquid phase is increased quickly in the chelation process, and the concentration difference between the two phases disappears quickly, so that the mass transfer driving force is attenuated quickly; when the reactant concentration is high, the mass transfer driving force can be obviously improved, but the reaction is easy to be incomplete due to the too high reactant concentration. The results of the binding assay are shown in FIG. 3, with an alternative reactant concentration of 60% being preferred.
On the basis of a single-factor test, 4 factors of temperature (A), pH (B), reactant concentration (C) and time (D) are selected as independent variables, threonine calcium chelation energy rate (Y) is taken as a response value, a four-factor three-level response surface test is carried out, level codes are shown in table 1, and analysis results are shown in table 2.
TABLE 1 orthogonal test factors and horizontal coding
TABLE 2 results of orthogonal experiments
According to the R in the table 1, the order of the factors influencing the calcium chelation rate of threonine is as follows: reaction temperature > reaction time > reactant concentration > pH value. The optimal combination is A2B3C2D2 from the perspective of the chelation rate of different levels of threonine calcium, and the chelation rate is 97.1% as verified by further experiments with the combination of A2B3C2D 2. Therefore, the optimal synthesis process of L-threonine and calcium oxide is as follows: the temperature is 80 ℃, the pH value is 8, the reactant concentration is 60 percent, and the reaction time is 2 hours.
Test example 2
This test example shows the calcium threonine chelation rate and yield in examples 1 to 4.
(1) The chelation rate was determined as follows:
the calcium ion chelation rate is measured by EDTA complexation titration.
The method for processing the sample when the total calcium content is measured comprises the following steps: 5mL of threonine-calcium reaction solution is taken, and the volume of deionized water is adjusted to 50 mL.
The method for processing the sample during the determination of the calcium threonine content comprises the following steps: and adding 3 times of volume of absolute ethyl alcohol into another 5mL of reaction solution, fully and uniformly mixing, centrifuging at 10000r/min for 15min, removing supernatant, and fixing the volume of the precipitate to 50mL by using deionized water.
EDTA complexometric titration: and (3) taking 20mL of reaction liquid with constant volume, dropwise adding a xylenol orange indicator, dropwise adding 20% by mass of hexamethylenetetramine until the solution is in a stable mauve color, then adding 4mL of hexamethylenetetramine, titrating by using 0.01mol/L EDTA, and finally obtaining the end point when the solution is changed from the mauve color to yellow color.
In the formula, C: the concentration of EDTA solution, mol/L;
Vblank space: replacing the required volume of EDTA (ethylene diamine tetraacetic acid) of the solution to be detected by using deionized water, wherein the volume is mL;
Vgeneral assembly: the total calcium content was measured as the volume of EDTA consumed at that time, mL;
Vchelation: the volume of EDTA (ethylene diamine tetraacetic acid) consumed in the determination of the content of the chelated calcium is mL;
the test results show that the chelation rates of calcium threonine in examples 1 to 4 are shown in fig. 5, in which the chelation rate of example 1 is 96.5%, the chelation rate of example 2 is 95.9%, the chelation rate of example 3 is 96.6%, and the chelation rate of example 4 is the highest and 97.1%.
(2) The yield was determined as follows:
accurately weighing the mass of the amino acid and zinc raw material to be added, calculating the theoretical mass of a product obtained by reaction according to a chemical method and a reaction principle, and finally comparing the theoretical mass with the mass of the amino acid chelated zinc collected actually. The calculation formula is shown in the following chart:
in the formula, the actual yield is the mass of the amino acid chelated zinc actually obtained, and the unit is g; the theoretical yield is the theoretical mass of the amino acid chelated zinc obtained by the reaction calculated according to a chemical method and a reaction principle, and the unit is g.
The yields of calcium threonine in examples 1 to 4 of the present invention measured by the test are shown in fig. 6, in which the yield of example 1 is 97.1%, the yield of example 2 is 96.5%, the yield of example 3 is 98.5%, and the yield of example 4 is 98.1%.
Test example 3
This experimental example illustrates the structural characterization of calcium threonine.
Scanning and analyzing the threonine calcium (example 4) and the L-threonine prepared under the optimal process conditions by using a Nexus470 intelligent Fourier transform infrared spectrometer to obtain infrared spectra shown in figures 7 to 8. After L-threonine and calcium ions are subjected to chelation reaction, the corresponding characteristic peak position is obviously shifted. As can be seen, L-threonine is 3170cm-1The characteristic absorption peak of the N-H bond is obviously shifted after forming a chelate and appears at 3390cm-1、3330cm-1. 1590cm of carboxylate ions in calcium threonine-1、1420cm-1Compared with the characteristic peak 1640cm of the carboxylate ions in threonine-1And 1460cm-1Blue shift occurs, which indicates that carboxyl participates in coordination reaction, and proves the generation of threonine calcium.
Test example 4
This test example illustrates the simulated digestion of calcium threonine in vitro at different chelation rates
Dissolving threonine calcium and calcium carbonate with different chelation rates in deionized water, adjusting the pH value of the solution to 2.0 by using 1mol/L HCl, adding pepsin in a certain proportion, mixing uniformly, and oscillating in a water bath at 37 ℃ for 2 hours; after the reaction is finished, adding pancreatin and bile extract in a certain proportion into the mixed system, adjusting the pH value of the system to 7.2, transferring the mixture into a dialysis bag (6000Da), and shaking the water bath at 37 ℃ for 2 h.
(1) Determination of calcium ion dissolution rate
In the simulated digestion process, after the pepsin is digested for 2 hours and the pepsin-pancreatin is digested for 4 hours, the supernatant is taken, and the calcium ion content in the supernatant is determined by using an EDTA (ethylene diamine tetraacetic acid) complexation titration method so as to represent the calcium ion dissolution rate in different digestion stages.
V1: titrating the volume of EDTA solution required by calcium ions in the supernatant, namely mL;
v2: titrating the volume of EDTA solution required by calcium ions in the equal volume of the solution, wherein the volume is mL;
c: concentration of EDTA solution, mol/L.
(2) Determination of calcium ion dialysance
After the digestion by pancreatin, the water solution outside the dialysis bag is taken, and the calcium ion content in the water solution is determined by EDTA complexometric titration to show the calcium ion content penetrating through the simulated intestinal tract.
V1: titrating the volume of EDTA solution required by calcium ions in the supernatant, namely mL;
v2: titrating the volume of EDTA solution required by calcium ions in the equal volume of the solution, wherein the volume is mL;
c: concentration of EDTA solution, mol/L.
The factors influencing the utilization rate of calcium in diet are many, the absorption rate of calcium in diet is low in human body, the main reason is that calcium and phytic acid can form insoluble complex in small intestine, the insoluble calcium-phytic acid complex can not be absorbed and utilized by human body due to lack of corresponding phytase in human intestine, the bioavailability of calcium is greatly reduced, the bioavailability of mineral elements can be evaluated by using in vitro simulated gastrointestinal tract digestion-dialysis method, the dialysance and solubility of threonine calcium and calcium carbonate with different chelation rates are measured according to the experimental method described by Wolfgor and the like, and the dissolubility and dialysance of two substances after gastrointestinal tract digestion are shown in fig. 9-11. From the experimental results, the dissolution rate shows a rising trend after gastrointestinal tract digestion along with the increase of the chelation rate, and the maximum dissolution rates in the stomach and the intestinal tract are 98.91 percent and 54.42 percent respectively; the dissolution rates of calcium ions in the calcium carbonate after being digested by the stomach and the intestinal tract are 97.99 percent and 35.84 percent respectively. In addition, along with the increase of the chelation rate, the dialysis filtration of calcium ions in the threonine calcium also shows a rising trend, the maximum dialysis rate is 43.14%, while the dialysis rate of the calcium ions in the calcium carbonate is 23.01%, the dialysis rate of the calcium ions in the threonine calcium is obviously higher than that of the calcium ions in the calcium carbonate, and although the calcium carbonate exists in a dissolved state in a stomach environment, the solubility of the calcium carbonate is obviously reduced after entering an intestinal environment, so that the calcium ions in the threonine calcium can more easily enter the intestinal environment, which shows that the bioavailability of the threonine calcium is higher compared with the calcium carbonate, and the increase of the chelation rate of the threonine calcium can improve the bioavailability of the threonine calcium.
The above embodiments are only used for illustrating the technical solution of the present invention, and not for limiting the same; although the invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that various changes may be made and equivalents may be substituted for elements thereof; but it is also intended to cover such modifications or alterations insofar as they come within the scope of the appended claims.
Claims (10)
1. A production method of a threonine calcium product is characterized by comprising the following steps:
(1) putting a certain amount of water into a reaction kettle, heating to 40-65 ℃, then putting the L-threonine and calcium raw materials in proportion, and stirring and mixing uniformly;
(2) adjusting the pH and temperature of the solution, and carrying out synthetic reaction in a closed reaction kettle for a plurality of times;
(3) after the synthesis reaction is finished, filtering for later use;
(4) and (3) treating the filtrate by adopting a spray drying method or a crystallization method to prepare a threonine calcium product.
2. The production method of the threonine calcium product as claimed in claim 1, wherein the mass ratio of the L-threonine to the calcium raw material in the step (1) is 190-210: 75-200% and the concentration of the reactant is 30-80%.
3. The method for producing a threonine calcium product as claimed in claim 2, wherein the reaction temperature in the step (2) is 45-90 ℃, the pH value is 6-10, and the reaction time is 1.5-4 h.
4. The method for producing a threonine calcium product as claimed in claim 3, wherein the filter membrane for filtration in the step (3) has a pore size of 0.1-0.45 mm.
5. The method for producing a threonine calcium product as claimed in claim 4, wherein the spray drying method adopted in the step (4) comprises the following process conditions: the temperature of the air inlet is 150-300 ℃, the temperature of the air outlet is 50-150 ℃, and the feeding speed is 40-80 kg/h.
6. The method for producing the threonine calcium product as claimed in claim 4, wherein the process for preparing the threonine calcium product by adopting the crystallization method in the step (4) comprises the following steps: evaporating and concentrating the filtrate until threonine calcium crystals are separated out, stopping concentrating, slowly cooling, filtering after a large amount of crystals are gradually separated out, and washing and drying the filter cake to obtain the threonine calcium crystals with uniform particles.
7. The method for producing a threonine calcium product as claimed in claim 6, wherein the crystallization in step (4) is carried out under the following conditions: the temperature of evaporation concentration is 40-90 ℃, the stirring speed is 10-25 r/min, and the temperature reduction gradient is 5-15 ℃/h.
8. A production method of a threonine calcium product is characterized by comprising the following steps: weighing 24.5kg of water in a reaction kettle, and adding 11.9kg of threonine while stirring after the temperature is raised to 50 ℃; after threonine is fully dissolved, adding 2.8kg of calcium oxide, controlling the concentration of a reactant to be 60%, controlling the temperature of a feed liquid to be 80 ℃, adjusting the pH value of the feed liquid to be 8, stirring and reacting for 2 hours, filtering by adopting a 0.45mm membrane, then carrying out evaporation concentration, adjusting the temperature to be 60 ℃, stirring at a speed of 25r/min, reducing the temperature gradient to be 10 ℃/h, stopping concentration when crystals are separated out, starting to slowly reduce the temperature at 10 ℃/h, filtering after a large amount of crystals are gradually separated out, washing and drying a filter cake, and obtaining calcium threonine crystals.
9. A threonine calcium product prepared by the production method according to any one of claims 1 to 8.
10. A threonine calcium product as claimed in claim 9, which has a 97.1% chelation rate.
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