CH396027A - Procédé de dédoublement de la DL-lysine - Google Patents
Procédé de dédoublement de la DL-lysineInfo
- Publication number
- CH396027A CH396027A CH676360A CH676360A CH396027A CH 396027 A CH396027 A CH 396027A CH 676360 A CH676360 A CH 676360A CH 676360 A CH676360 A CH 676360A CH 396027 A CH396027 A CH 396027A
- Authority
- CH
- Switzerland
- Prior art keywords
- lysine
- tartrate
- mixed
- sub
- solvent
- Prior art date
Links
- KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 title claims description 58
- 238000000034 method Methods 0.000 title claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 66
- 239000004472 Lysine Substances 0.000 claims description 40
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 29
- 235000019766 L-Lysine Nutrition 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 229940095064 tartrate Drugs 0.000 claims description 22
- 239000000243 solution Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000002425 crystallisation Methods 0.000 claims description 16
- 230000008025 crystallization Effects 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 150000003892 tartrate salts Chemical class 0.000 claims description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 238000006266 etherification reaction Methods 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 235000018977 lysine Nutrition 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 6
- 150000008545 L-lysines Chemical class 0.000 description 6
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 5
- AVTYONGGKAJVTE-OTWIGTIJSA-L dipotassium;(2s,3s)-2,3-dihydroxybutanedioate Chemical compound [K+].[K+].[O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O AVTYONGGKAJVTE-OTWIGTIJSA-L 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229960001367 tartaric acid Drugs 0.000 description 5
- 235000002906 tartaric acid Nutrition 0.000 description 5
- 239000011975 tartaric acid Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 229960001270 d- tartaric acid Drugs 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 150000002306 glutamic acid derivatives Chemical class 0.000 description 3
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical class OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 3
- 235000016337 monopotassium tartrate Nutrition 0.000 description 3
- KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 3
- 229940081543 potassium bitartrate Drugs 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 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 description 3
- 238000005406 washing Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000008564 D-lysines Chemical class 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 2
- NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- -1 potassium-lysine D-tartrates Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
- HOMROMWVNDUGRI-RVZXSAGBSA-N (2s)-2-aminopentanedioic acid;(2s)-2,6-diaminohexanoic acid Chemical compound NCCCC[C@H](N)C(O)=O.OC(=O)[C@@H](N)CCC(O)=O HOMROMWVNDUGRI-RVZXSAGBSA-N 0.000 description 1
- LSPHULWDVZXLIL-LDWIPMOCSA-N (?)-Camphoric acid Chemical compound CC1(C)[C@@H](C(O)=O)CC[C@@]1(C)C(O)=O LSPHULWDVZXLIL-LDWIPMOCSA-N 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- NGPGDYLVALNKEG-OLXYHTOASA-N diammonium L-tartrate Chemical compound [NH4+].[NH4+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O NGPGDYLVALNKEG-OLXYHTOASA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002669 lysines Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR799606A FR1270011A (fr) | 1959-07-07 | 1959-07-07 | Procédé de dédoublement de la dl-lysine et produits pour sa mise en oeuvre |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH396027A true CH396027A (fr) | 1965-07-31 |
Family
ID=8716923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH676360A CH396027A (fr) | 1959-07-07 | 1960-06-14 | Procédé de dédoublement de la DL-lysine |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE591857A (enrdf_load_stackoverflow) |
| CH (1) | CH396027A (enrdf_load_stackoverflow) |
| FR (1) | FR1270011A (enrdf_load_stackoverflow) |
| LU (1) | LU38824A1 (enrdf_load_stackoverflow) |
-
1959
- 1959-07-07 FR FR799606A patent/FR1270011A/fr not_active Expired
-
1960
- 1960-06-14 BE BE591857A patent/BE591857A/fr unknown
- 1960-06-14 CH CH676360A patent/CH396027A/fr unknown
- 1960-06-15 LU LU38824D patent/LU38824A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE591857A (fr) | 1960-10-03 |
| FR1270011A (fr) | 1961-08-25 |
| LU38824A1 (enrdf_load_stackoverflow) | 1960-08-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0308341A1 (fr) | Procédé de synthèse industrielle du périndopril et de ses principaux intermédiaires de synthèse | |
| BE1008403A4 (fr) | Procede de cristallisation d'iopamidol. | |
| FR2571366A1 (fr) | Procede de preparation de la l-carnitine et de ses sels | |
| CH396027A (fr) | Procédé de dédoublement de la DL-lysine | |
| BE506950A (enrdf_load_stackoverflow) | ||
| EP0093128B1 (fr) | Procede de preparation de l'ester-methylique de l'alpha-aspartyl phenylalanine | |
| WO1998039286A1 (fr) | PROCEDE D'OBTENTION D'ENANTIOMERES D'ACIDES α-AMINES ET SELS DIASTEREOISOMERIQUES INTERMEDIAIRES | |
| WO2018015677A1 (fr) | Procédé de dédoublement de sels de baclofène | |
| EP0946467A1 (fr) | Procede de dedoublement de composes 1-amino-alcan-2-ol | |
| EP0023178A1 (fr) | Procédé de préparation de solutions concentrées d'amygdaline sous sa forme naturelle | |
| FR2760016A1 (fr) | Procede de fabrication industrielle de diosmine a partir de l'hesperidine | |
| CH508590A (fr) | Procédé de préparation des esters d'alcoyle inférieurs de l'a-L-aspartyl-L-phénylalanine | |
| EP0524082A1 (fr) | Procédé de préparation du cis-inositol, du méso-inositol, de l'épi-inositol et/ou du cis-quercitol éventuellement deutérés | |
| FR2554813A1 (fr) | Procede pour la recuperation de tryptophane optiquement actif | |
| BE865027A (fr) | Procede de preparation de la 5-(4-jydroxyphenyl)-hydantoine | |
| BE557360A (enrdf_load_stackoverflow) | ||
| CH401082A (fr) | Procédé pour le dédoublement optique de l'acide homocystéique ou d'un sel de monoammonium de celui-ci | |
| BE569211A (enrdf_load_stackoverflow) | ||
| BE541639A (enrdf_load_stackoverflow) | ||
| BE827580A (fr) | Preparation de d et l-2-amino-1-butanol | |
| BE475595A (enrdf_load_stackoverflow) | ||
| BE505022A (enrdf_load_stackoverflow) | ||
| BE402029A (enrdf_load_stackoverflow) | ||
| CH257402A (fr) | Procédé pour la préparation de 5-nitro-anilines présentant en position 2 un reste-OR. | |
| BE898073A (fr) | Procede de preparation de la vincamine. |