BE583109A - - Google Patents

Info

Publication number

BE583109A

BE583109A BE583109DA BE583109A BE 583109 A BE583109 A BE 583109A BE 583109D A BE583109D A BE 583109DA BE 583109 A BE583109 A BE 583109A

Authority

BE

Belgium

Prior art keywords

bis

threonine

solution

aldehyde

copper

Prior art date

Links

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• AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 34
• AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 27
• 239000004473 Threonine Substances 0.000 claims description 23
• 239000010949 copper Substances 0.000 claims description 21
• 229910052802 copper Inorganic materials 0.000 claims description 18
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 17
• 239000000203 mixture Substances 0.000 claims description 13
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 7
• 239000012535 impurity Substances 0.000 claims description 7
• 229910000037 hydrogen sulfide Inorganic materials 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
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
• 239000003729 cation exchange resin Substances 0.000 claims description 5
• -1 aliphatic aldehyde Chemical class 0.000 claims description 4
• 239000013522 chelant Substances 0.000 claims description 4
• 239000012141 concentrate Substances 0.000 claims description 4
• 238000002955 isolation Methods 0.000 claims description 4
• 238000000034 method Methods 0.000 claims description 4
• 239000000725 suspension Substances 0.000 claims description 4
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
• 239000007900 aqueous suspension Substances 0.000 claims description 3
• 238000001914 filtration Methods 0.000 claims description 2
• 239000002244 precipitate Substances 0.000 claims description 2
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 6
• 239000002609 medium Substances 0.000 claims 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
• 239000012736 aqueous medium Substances 0.000 claims 2
• 125000004432 carbon atom Chemical group C* 0.000 claims 2
• 150000003588 threonines Chemical class 0.000 claims 2
• 229910021529 ammonia Inorganic materials 0.000 claims 1
• 239000003054 catalyst Substances 0.000 claims 1
• 238000001556 precipitation Methods 0.000 claims 1
• 238000000746 purification Methods 0.000 claims 1
• 239000011347 resin Substances 0.000 claims 1
• 229920005989 resin Polymers 0.000 claims 1
• 239000002904 solvent Substances 0.000 claims 1
• 150000003587 threonine derivatives Chemical class 0.000 claims 1
• 229960002898 threonine Drugs 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 9
• 150000001299 aldehydes Chemical class 0.000 description 7
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
• 239000000047 product Substances 0.000 description 6
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
• 150000001875 compounds Chemical class 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• 229940116318 copper carbonate Drugs 0.000 description 3
• GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 3
• NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
• 238000004458 analytical method Methods 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000008025 crystallization Effects 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• VSSZGOGPSUSTIV-PZXRSRGQSA-N (2S,3R)-2-amino-3-hydroxybutanoic acid copper Chemical compound [Cu].C[C@@H](O)[C@H](N)C(O)=O.C[C@@H](O)[C@H](N)C(O)=O VSSZGOGPSUSTIV-PZXRSRGQSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• 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 1
• VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 230000005587 bubbling Effects 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 150000001879 copper Chemical class 0.000 description 1
• BWFPGXWASODCHM-UHFFFAOYSA-N copper monosulfide Chemical compound [Cu]=S BWFPGXWASODCHM-UHFFFAOYSA-N 0.000 description 1
• 239000002198 insoluble material Substances 0.000 description 1
• 238000004816 paper chromatography Methods 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 1