JP2022514748A - リシン水溶液からモノリシネート化合物の調製する方法 - Google Patents
リシン水溶液からモノリシネート化合物の調製する方法 Download PDFInfo
- Publication number
- JP2022514748A JP2022514748A JP2021535175A JP2021535175A JP2022514748A JP 2022514748 A JP2022514748 A JP 2022514748A JP 2021535175 A JP2021535175 A JP 2021535175A JP 2021535175 A JP2021535175 A JP 2021535175A JP 2022514748 A JP2022514748 A JP 2022514748A
- Authority
- JP
- Japan
- Prior art keywords
- monolithinate
- lysine
- metal
- compound
- metal salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000004472 Lysine Substances 0.000 title claims abstract description 191
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 title claims abstract description 187
- 150000001875 compounds Chemical class 0.000 title claims abstract description 149
- 238000000034 method Methods 0.000 title claims abstract description 69
- 229910052751 metal Inorganic materials 0.000 claims abstract description 198
- 239000002184 metal Substances 0.000 claims abstract description 198
- 150000003839 salts Chemical class 0.000 claims abstract description 141
- 239000011541 reaction mixture Substances 0.000 claims abstract description 86
- 239000007788 liquid Substances 0.000 claims abstract description 63
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- 238000001035 drying Methods 0.000 claims abstract description 20
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 200
- 229960003646 lysine Drugs 0.000 claims description 191
- 239000000243 solution Substances 0.000 claims description 58
- 239000007864 aqueous solution Substances 0.000 claims description 55
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 32
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 22
- 150000001450 anions Chemical class 0.000 claims description 21
- 239000008187 granular material Substances 0.000 claims description 18
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 claims description 16
- 239000011702 manganese sulphate Substances 0.000 claims description 15
- 235000007079 manganese sulphate Nutrition 0.000 claims description 15
- 229940099596 manganese sulfate Drugs 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 13
- 229910052742 iron Inorganic materials 0.000 claims description 13
- 239000011572 manganese Substances 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052748 manganese Inorganic materials 0.000 claims description 10
- 239000011701 zinc Substances 0.000 claims description 9
- 239000010949 copper Substances 0.000 claims description 8
- 235000013373 food additive Nutrition 0.000 claims description 8
- 239000002778 food additive Substances 0.000 claims description 8
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 8
- 239000003337 fertilizer Substances 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 150000001805 chlorine compounds Chemical class 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 5
- 150000004692 metal hydroxides Chemical class 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 244000144972 livestock Species 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 229910000358 iron sulfate Inorganic materials 0.000 claims description 3
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical group [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 3
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical group [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 150000002505 iron Chemical class 0.000 claims description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 claims 2
- 229960001763 zinc sulfate Drugs 0.000 claims 2
- 235000018977 lysine Nutrition 0.000 description 171
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- 235000001014 amino acid Nutrition 0.000 description 29
- 150000001413 amino acids Chemical class 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 24
- 125000004429 atom Chemical group 0.000 description 20
- 239000007858 starting material Substances 0.000 description 16
- 239000000843 powder Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 13
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 12
- 239000013522 chelant Substances 0.000 description 12
- 238000005260 corrosion Methods 0.000 description 12
- 230000007797 corrosion Effects 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000011573 trace mineral Substances 0.000 description 10
- 235000013619 trace mineral Nutrition 0.000 description 10
- 239000012535 impurity Substances 0.000 description 9
- -1 salt compound Chemical class 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000005469 granulation Methods 0.000 description 8
- 230000003179 granulation Effects 0.000 description 8
- 229910001385 heavy metal Inorganic materials 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000011575 calcium Substances 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 239000012467 final product Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000004471 Glycine Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000000855 fermentation Methods 0.000 description 6
- 230000004151 fermentation Effects 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 229910021645 metal ion Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 238000001694 spray drying Methods 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 150000002697 manganese compounds Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910001510 metal chloride Inorganic materials 0.000 description 5
- 150000002736 metal compounds Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 235000019766 L-Lysine Nutrition 0.000 description 4
- KDXKERNSBIXSRK-YFKPBYRVSA-M L-lysinate Chemical class NCCCC[C@H](N)C([O-])=O KDXKERNSBIXSRK-YFKPBYRVSA-M 0.000 description 4
- 125000000539 amino acid group Chemical group 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000635 electron micrograph Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002500 ions Chemical group 0.000 description 4
- 235000001055 magnesium Nutrition 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 239000005569 Iron sulphate Substances 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- 235000015872 dietary supplement Nutrition 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 150000002506 iron compounds Chemical class 0.000 description 3
- 159000000014 iron salts Chemical class 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 159000000003 magnesium salts Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 235000010689 Lufa Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 2
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 125000005586 carbonic acid group Chemical group 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 210000002808 connective tissue Anatomy 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000003574 free electron Substances 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 2
- 239000011565 manganese chloride Substances 0.000 description 2
- 235000002867 manganese chloride Nutrition 0.000 description 2
- 229940099607 manganese chloride Drugs 0.000 description 2
- 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 description 2
- 238000004137 mechanical activation Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052755 nonmetal Inorganic materials 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 0 CC1=*(C)CCCC1 Chemical compound CC1=*(C)CCCC1 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001274216 Naso Species 0.000 description 1
- 241000080590 Niso Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000034809 Product contamination Diseases 0.000 description 1
- XYQRXRFVKUPBQN-UHFFFAOYSA-L Sodium carbonate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]C([O-])=O XYQRXRFVKUPBQN-UHFFFAOYSA-L 0.000 description 1
- YDFRFVFUBOYQIX-UHFFFAOYSA-H [B+3].C([O-])([O-])=O.C([O-])([O-])=O.C([O-])([O-])=O.[B+3] Chemical compound [B+3].C([O-])([O-])=O.C([O-])([O-])=O.C([O-])([O-])=O.[B+3] YDFRFVFUBOYQIX-UHFFFAOYSA-H 0.000 description 1
- COXUNHIKBNZLLM-UHFFFAOYSA-H [B+3].[B+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O Chemical compound [B+3].[B+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O COXUNHIKBNZLLM-UHFFFAOYSA-H 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 125000003275 alpha amino acid group Chemical group 0.000 description 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000023852 carbohydrate metabolic process Effects 0.000 description 1
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 102000038379 digestive enzymes Human genes 0.000 description 1
- 108091007734 digestive enzymes Proteins 0.000 description 1
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000006052 feed supplement Substances 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 150000004698 iron complex Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000002934 lysing effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 150000004682 monohydrates Chemical group 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000001668 nucleic acid synthesis Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229940081066 picolinic acid Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940018038 sodium carbonate decahydrate Drugs 0.000 description 1
- 229940076133 sodium carbonate monohydrate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
-
- 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
- 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
- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/045—Organic compounds containing nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05F—ORGANIC FERTILISERS NOT COVERED BY SUBCLASSES C05B, C05C, e.g. FERTILISERS FROM WASTE OR REFUSE
- C05F5/00—Fertilisers from distillery wastes, molasses, vinasses, sugar plant or similar wastes or residues, e.g. from waste originating from industrial processing of raw material of agricultural origin or derived products thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- 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
- C07C227/14—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nutrition Science (AREA)
- Health & Medical Sciences (AREA)
- Botany (AREA)
- Environmental & Geological Engineering (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Abstract
Description
・570グラムのモノリシネート硫酸マンガン(57%)
・50重量%のリシン含有量を有する980グラムのリシン水溶液
・700グラムの追加の水。
・570グラムのモノリシネート硫酸鉄(57%)
・50重量%のリシン含有量を有する980グラムのリシン水溶液
・700グラムの追加の水。
102 アミノ酸リシンのアミノ酸残基
104 アミノ酸リシンのアミノ基
106 アミノ酸リシンのカルボキシル基
200 モノリシネート化合物の一般構造式
300 図2のモノリシネートの例
400 モノリシネート化合物の一般構造式
500 図4のモノリシネートの例
600 モノリシネート化合物の一般構造式
602~608 工程
700 図6のモノリシネートの例
702~706 工程
800 モノリシネート化合物の一般構造式
802 リシン分子
804 硫酸マンガン
806 反応率
808 攪拌装置
810 液体反応混合体
900 図8のモノリシネートの例
Claims (19)
- モノリシネート化合物(200、300、400、500、600、700、800、900)の調製方法であって、
リシン(802)および金属塩(404)が溶解する液体反応混合体(810)を提供する工程(502)と、
前記反応混合体に溶解した前記リシン(802)と前記金属塩とを反応させ、モノリシネート化合物を形成する工程(306)と、
前記モノリシネート化合物を取得するため、前記液体反応混合体を乾燥させる工程(308)とを有するものである
方法。 - 請求項1記載の方法において、リシン水溶液を提供する工程(302)と、前記金属塩(404)を前記リシン水溶液に溶解することにより、前記液体反応混合体(810)を調製する工程(304)とを有するものである方法。
- 請求項1~3のいずれか一項記載の方法において、前記モノリシネート化合物において、正確に1つのリシン分子が前記金属塩の正確に1つの金属塩に結合し、前記結合がイオン結合である方法。
- 請求項1~4のいずれか一項記載の方法において、前記金属塩は金属硫酸塩、金属水酸化物、または金属炭酸塩である方法。
- 請求項1~5のいずれか一項記載の方法において、前記金属塩の金属は二価の金属、特にMn2+、Fe2+、Zn2+、Cu2+、Ca2+、Mg2+、Co2+、Na2+、またはNi2+である方法。
- 請求項1~6のいずれか一項記載の方法において、前記モノリシネート化合物は、モノリシネート硫酸マンガン、モノリシネート硫酸鉄である方法。
- 請求項1~7のいずれか一項記載の方法において、前記金属塩は硫酸亜鉛(ZnSO4)、硫酸鉄(FeSO4)、または硫酸マンガン(MnSO4)である方法。
- 請求項1~8のいずれか一項記載の方法において、前記液体反応混合体は、前記リシン1モルに対し前記金属塩の金属原子1モルのモル比で、金属塩を前記リシン水溶液に溶解することにより調製されるものである方法。
- 請求項1~9のいずれか一項記載の方法において、前記反応は、少なくとも摂氏60度、好ましくは摂氏60度~摂氏90度の温度で少なくとも15分間、前記溶解したリシンおよび前記溶解した金属塩を機械的に混合する工程を有するものである方法。
- 請求項1~10のいずれか一項記載の方法において、前記提供されるリシン水溶液は、前記リシン水溶液に対し、少なくとも30重量%、好ましくは少なくとも40重量%のリシン含有量を有するものである方法。
- 請求項1~11のいずれか一項記載の方法において、前記リシン水溶液および前記液体反応混合体は、塩化物およびCl-イオンを実質的に含んでいない、特にリシンHCl塩を実質的に含んでいないものである方法。
- 請求項1~12のいずれか一項記載の方法において、前記液体反応混合体は、pH8.0~8.3で前記金属塩が硫酸マンガンである、pH6.4~6.8で前記金属塩が硫酸鉄である、pH5.5~5.9で前記金属塩が硫酸亜鉛である、またはpH3.6~4.0で前記金属塩が硫酸銅である方法。
- 請求項1~13のいずれか一項記載の方法において、前記リシンン水溶液および前記液体反応混合体は、前記金属塩が鉄塩でない場合、更なる有機酸を全く含んでいない、および/または前記金属塩が鉄塩の場合、有機酸、特にクエン酸を含むものである方法。
- 請求項1~14のいずれか一項記載の方法において、前記乾燥後または前記乾燥中に、前記モノリシネート化合物から顆粒を生成する工程を更に有するものである方法。
- モノリシネート化合物(200、300、400、500、600、700、800、900)であって、
請求項1~15のいずれか一項記載の方法によって生成されるものである
モノリシネート化合物。 - 請求項16~17のいずれか一項記載のモノリシネート化合物において、前記金属塩は金属硫酸塩、金属水酸化物、または金属炭酸塩である、および/または前記金属塩の金属は二価の金属、特にMn2+、Fe2+、Zn2+、Cu2+、Ca2+、Mg2+、Co2+、Na2+、またはNi2+であり、好ましくは塩化物および塩化物イオンを全く含んでいないものであるモノリシネート化合物。
- 請求項16~18のいずれか一項記載のモノリシネート化合物の使用であって、
家畜およびペット用の餌添加物、および/または発酵添加物、および/または肥料添加物、および/または食品添加物、および/または食品補足剤としての
使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP18213331.4A EP3670494B1 (de) | 2018-12-18 | 2018-12-18 | Herstellung einer lysinat-verbindung aus einer wässrigen lysinlösung |
EP18213331.4 | 2018-12-18 | ||
PCT/EP2019/084346 WO2020126647A1 (de) | 2018-12-18 | 2019-12-10 | Herstellung einer lysinat-verbindung aus einer wässrigen lysinlösung |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2022514748A true JP2022514748A (ja) | 2022-02-15 |
JPWO2020126647A5 JPWO2020126647A5 (ja) | 2024-03-13 |
Family
ID=65009517
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2021535175A Pending JP2022514748A (ja) | 2018-12-18 | 2019-12-10 | リシン水溶液からモノリシネート化合物の調製する方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US20220024856A1 (ja) |
EP (2) | EP3670494B1 (ja) |
JP (1) | JP2022514748A (ja) |
KR (1) | KR20210108379A (ja) |
CN (2) | CN113316565B (ja) |
ES (1) | ES2955166T3 (ja) |
PL (1) | PL3670494T3 (ja) |
WO (1) | WO2020126647A1 (ja) |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5061815A (en) * | 1988-07-06 | 1991-10-29 | Zinpro Corporation | Metal lysine complexes and method for producing metal lysine complexes |
US4948594A (en) * | 1989-01-03 | 1990-08-14 | Zinpro Corporation | Copper complexes of alpha-amino acids that contain terminal amino groups, and their use as nutritional supplements |
US6670494B1 (en) * | 2001-12-17 | 2003-12-30 | J H Brotech, Inc. | Method for preparation of metal organic acid chelates |
US7022351B2 (en) * | 2003-01-14 | 2006-04-04 | Zinpro Corporation | Composition for supplementing animals with solutions of essential metal amino acid complexes |
CN101172956A (zh) * | 2007-10-26 | 2008-05-07 | 白家强 | 单体赖氨酸锌及再转为赖氨酸锌络合物的制备和用途 |
FR2935383B1 (fr) * | 2008-08-26 | 2010-10-01 | Pancosma Sa Pour L Ind Des Pro | Procede et dispositif pour la fabrication de complexes organometalliques en poudre. |
DE102011011924B4 (de) | 2011-02-17 | 2012-12-27 | Isf Gmbh | Verfahren zur Herstellung von Aminosäure-Chelat-Verbindungen, Aminosäure-Chelat-Verbindungen und Verwendung von Aminosäure-Chelat-Verbindungen |
US9149057B2 (en) * | 2011-03-01 | 2015-10-06 | Zinpro Corporation | Enhanced bioavailable iodine molecules |
CN104739816B (zh) * | 2015-02-25 | 2017-10-27 | 刘力 | 包括手性异构化合物的赖葡锌药物组合物及其用途 |
WO2018111756A1 (en) * | 2016-12-12 | 2018-06-21 | Novus International Inc. | Metal complexes |
-
2018
- 2018-12-18 PL PL18213331.4T patent/PL3670494T3/pl unknown
- 2018-12-18 EP EP18213331.4A patent/EP3670494B1/de active Active
- 2018-12-18 ES ES18213331T patent/ES2955166T3/es active Active
-
2019
- 2019-12-10 CN CN201980083696.XA patent/CN113316565B/zh active Active
- 2019-12-10 US US17/415,271 patent/US20220024856A1/en active Pending
- 2019-12-10 WO PCT/EP2019/084346 patent/WO2020126647A1/de unknown
- 2019-12-10 KR KR1020217019031A patent/KR20210108379A/ko active Search and Examination
- 2019-12-10 JP JP2021535175A patent/JP2022514748A/ja active Pending
- 2019-12-10 EP EP19813588.1A patent/EP3898576A1/de active Pending
- 2019-12-10 CN CN202410055373.2A patent/CN117924104A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
ES2955166T3 (es) | 2023-11-29 |
US20220024856A1 (en) | 2022-01-27 |
EP3670494C0 (de) | 2023-06-14 |
EP3898576A1 (de) | 2021-10-27 |
WO2020126647A1 (de) | 2020-06-25 |
EP3670494B1 (de) | 2023-06-14 |
BR112021011993A2 (pt) | 2021-09-08 |
EP3670494A1 (de) | 2020-06-24 |
KR20210108379A (ko) | 2021-09-02 |
CN113316565B (zh) | 2024-02-02 |
PL3670494T3 (pl) | 2023-12-04 |
CN113316565A (zh) | 2021-08-27 |
CN117924104A (zh) | 2024-04-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US11807587B2 (en) | Acid treatment for fertilizers to increase zinc solubility and availability | |
JP6534194B2 (ja) | 微量栄養素補助食品 | |
US7691169B2 (en) | Partially chelated carboxylate nutrients and methods for their production and use | |
US9540289B2 (en) | Chelated compositions and methods of making and using the same | |
PL209541B1 (pl) | Obojętne kompleksy 1:1 pierwiastków śladowych i kwasów alfa aminodikarboksylowych | |
CA2347152C (en) | Chelated feed additive and method of preparation | |
WO2002030947A2 (en) | Compositions and methods of preparing amino acid chelates and complexes | |
CN113316565B (zh) | 由赖氨酸水溶液制备单赖氨酸盐化合物 | |
US6387412B1 (en) | Storage stable animal mineral granules | |
BR112021011993B1 (pt) | Processo para a preparação de um composto de monolisinato, composto de monolisinato e uso de um composto de monolisinato | |
CN113165988A (zh) | 具有水溶性微量营养元素的硫酸铵肥料 | |
KR100458132B1 (ko) | 금속 아미노산 복합체의 건조 분말을 제조하는 방법 | |
JPS5830273B2 (ja) | 醗酵廃液を固形化した肥料の製造方法 | |
PL232367B1 (pl) | Stymulator wzrostu i rozwoju roślin na bazie hydrolizatów białkowych | |
CN110419633A (zh) | 一种缓释型饲料级氯化铵及制备方法 | |
PL216951B1 (pl) | Sposób wytwarzania chelatów żelaza (III) kwasu dietylenotriaminopentaoctowego | |
GB2111814A (en) | A method for preparing a feed concentrate for ruminants | |
LT5059B (lt) | Trąšų priedas apimantis magnio ir kalcio sulfatus ir karbonatus |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20221110 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20230922 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20231017 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20240112 |
|
A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20240304 |