BE542933A - - Google Patents

Info

Publication number

BE542933A

BE542933A BE542933DA BE542933A BE 542933 A BE542933 A BE 542933A BE 542933D A BE542933D A BE 542933DA BE 542933 A BE542933 A BE 542933A

Authority

BE

Belgium

Prior art keywords

lysine

acid

glutamic acid

salt

water

Prior art date

Links

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• WHUUTDBJXJRKMK-UHFFFAOYSA-N glutamic acid Chemical compound OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 46
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 45
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 44
• 239000004472 Lysine Substances 0.000 claims description 32
• 229960002989 glutamic acid Drugs 0.000 claims description 29
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 20
• 235000018977 lysine Nutrition 0.000 claims description 20
• CKLJMWTZIZZHCS-UHFFFAOYSA-N Aspartic acid Chemical compound OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims description 19
• 239000002253 acid Substances 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 19
• 238000000034 method Methods 0.000 claims description 17
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
• 235000019766 L-Lysine Nutrition 0.000 claims description 12
• 239000000203 mixture Substances 0.000 claims description 8
• 230000004048 modification Effects 0.000 claims description 7
• 238000012986 modification Methods 0.000 claims description 7
• 239000013078 crystal Substances 0.000 claims description 6
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 5
• 239000003729 cation exchange resin Substances 0.000 claims description 5
• 239000000706 filtrate Substances 0.000 claims description 4
• GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical group [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 4
• 238000005342 ion exchange Methods 0.000 claims description 4
• 239000012452 mother liquor Substances 0.000 claims description 4
• 230000003287 optical effect Effects 0.000 claims description 4
• 239000011541 reaction mixture Substances 0.000 claims description 4
• 239000011347 resin Substances 0.000 claims description 4
• 229920005989 resin Polymers 0.000 claims description 4
• 238000003756 stirring Methods 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 3
• 238000001914 filtration Methods 0.000 claims description 3
• 229920001467 poly(styrenesulfonates) Polymers 0.000 claims description 3
• WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 claims description 3
• 125000001176 L-lysyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])C([H])([H])C(N([H])[H])([H])[H] 0.000 claims description 2
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 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 claims description 2
• -1 L-lysine L-glutamate monohydrate Chemical compound 0.000 claims 2
• OZDAOHVKBFBBMZ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrate Chemical compound O.OC(=O)[C@@H](N)CCC(O)=O OZDAOHVKBFBBMZ-DFWYDOINSA-N 0.000 claims 1
• 239000000126 substance Substances 0.000 claims 1
• 239000004220 glutamic acid Substances 0.000 description 14
• 235000013922 glutamic acid Nutrition 0.000 description 13
• CKLJMWTZIZZHCS-UWTATZPHSA-N D-aspartic acid Chemical compound OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 11
• HOMROMWVNDUGRI-RVZXSAGBSA-N (2s)-2-aminopentanedioic acid;(2s)-2,6-diaminohexanoic acid Chemical group NCCCC[C@H](N)C(O)=O.OC(=O)[C@@H](N)CCC(O)=O HOMROMWVNDUGRI-RVZXSAGBSA-N 0.000 description 7
• 229960005261 aspartic acid Drugs 0.000 description 7
• 238000006243 chemical reaction Methods 0.000 description 5
• 230000035484 reaction time Effects 0.000 description 5
• 235000003704 aspartic acid Nutrition 0.000 description 4
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 4
• 239000007787 solid Substances 0.000 description 4
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
• WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 description 3
• 235000011114 ammonium hydroxide Nutrition 0.000 description 3
• 150000001875 compounds Chemical class 0.000 description 3
• 238000000926 separation method Methods 0.000 description 3
• RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical compound Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• 229930182847 D-glutamic acid Natural products 0.000 description 2
• KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• 239000008346 aqueous phase Substances 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• 239000003795 chemical substances by application Substances 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• GGZZISOUXJHYOY-UHFFFAOYSA-N 8-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1O GGZZISOUXJHYOY-UHFFFAOYSA-N 0.000 description 1
• 241001501536 Alethe Species 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• 229930195713 D-glutamate Natural products 0.000 description 1
• NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
• 238000013019 agitation Methods 0.000 description 1
• 229940024606 amino acid Drugs 0.000 description 1
• 235000001014 amino acid Nutrition 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 229910052799 carbon Inorganic materials 0.000 description 1
• 238000005341 cation exchange Methods 0.000 description 1
• 238000001311 chemical methods and process Methods 0.000 description 1
• 239000013065 commercial product Substances 0.000 description 1
• PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 238000011081 inoculation Methods 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• 230000001376 precipitating effect Effects 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 230000006340 racemization Effects 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 239000011877 solvent mixture Substances 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 238000005406 washing Methods 0.000 description 1