CS209256B1 - Method of winning of threo-1-/p-nitrophenyl/-2-amino-1,3-propandioli and threo-1-/p-nitrophenyl/-2-dichlor acetamido-1,3-propandiole - Google Patents
Method of winning of threo-1-/p-nitrophenyl/-2-amino-1,3-propandioli and threo-1-/p-nitrophenyl/-2-dichlor acetamido-1,3-propandiole Download PDFInfo
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- CS209256B1 CS209256B1 CS265376A CS265376A CS209256B1 CS 209256 B1 CS209256 B1 CS 209256B1 CS 265376 A CS265376 A CS 265376A CS 265376 A CS265376 A CS 265376A CS 209256 B1 CS209256 B1 CS 209256B1
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- threo
- nitrophenyl
- propanediol
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- amino
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- 238000000034 method Methods 0.000 title claims description 14
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 title claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000012452 mother liquor Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000003957 anion exchange resin Substances 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 230000008929 regeneration Effects 0.000 claims description 5
- 238000011069 regeneration method Methods 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 4
- HKMLRUAPIDAGIE-UHFFFAOYSA-N methyl 2,2-dichloroacetate Chemical compound COC(=O)C(Cl)Cl HKMLRUAPIDAGIE-UHFFFAOYSA-N 0.000 claims description 4
- 239000003791 organic solvent mixture Substances 0.000 claims description 4
- 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 3
- 238000005349 anion exchange Methods 0.000 claims description 3
- 239000003729 cation exchange resin Substances 0.000 claims description 3
- 229960004275 glycolic acid Drugs 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- 238000001179 sorption measurement Methods 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 229960005215 dichloroacetic acid Drugs 0.000 claims description 2
- 238000010828 elution Methods 0.000 claims description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 235000010755 mineral Nutrition 0.000 claims description 2
- 239000012266 salt solution Substances 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims 2
- 239000000706 filtrate Substances 0.000 claims 2
- 238000005342 ion exchange Methods 0.000 claims 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 claims 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- 229960001948 caffeine Drugs 0.000 claims 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000005341 cation exchange Methods 0.000 claims 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000284 extract Substances 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 238000004809 thin layer chromatography Methods 0.000 claims 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 4
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 4
- 229960005091 chloramphenicol Drugs 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- UUNGBBYYZOMGGT-UHFFFAOYSA-N 2,2-dichloro-N-(1,3-dihydroxypropan-2-yl)acetamide Chemical compound ClC(C(=O)NC(CO)CO)Cl UUNGBBYYZOMGGT-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JIIOHQGYIPGZEB-UHFFFAOYSA-N N-(1-chloro-1,3-dihydroxypropyl)acetamide Chemical compound ClC(CCO)(O)NC(=O)C JIIOHQGYIPGZEB-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(54) Způsob získávání threo-l-(p-nitrofenyl)-2-amino-l,3-propandiolu a threol-(p-nitrofenyl)-2-dichloracetamido-l,3-propandiolu(54) A process for obtaining threo-1- (p-nitrophenyl) -2-amino-1,3-propanediol and threol- (p-nitrophenyl) -2-dichloroacetamido-1,3-propanediol
Vynález se týká způsobu získávání threo-l-(pnitrofenyl)-2-amino-l,3-propandiolu a threo-1(p-nitrofenyl)-2-chloracetamido-l,3-propandiolu z matečných louhů po dichloracetylaci threo-l-(pnitro£enyl)-2-amino-l ,3-propandiolu, obsahujících nezreagovaný threo-l-(p-nitrofenyl)-2-amino-l,3-propandiol, nevykrystalovaný threo-l-(pnitrofenyl)-2-dichloracetamido-1,3-propandiol, nezreagovaný a přebytečný dichloroctan methylnatý, kyselinu dichloroctovou, popřípadě hydroxyoctovou, chlorovodík, methanol a vodu. Získávání uvedených dvou látek patří k základním regeneračním pochodům při syntéze antibiotika í chloramfenikolu. Doposud se využívá klasických postupů, tj. odpaření matečného louhu, ochlazeni a krystalizace směsí obou látek. V této směsi se potom threo-l-(p-nitrofenyl)-2-dichloracetamido-1,3-propandiol hydrolýzuje na příslušný 2-ami’ noderivát, který se v poslední fázi převádí na málo rozpustnou Schiffovou bázi, zejména reakcí s ben; zaldehydem na příslušný benzylidenderivát. Nevýi hodou tohoto způsobu je skutečnost, že i při použití přebytku benzaldehydu zůstává v roztoku ještě významné množství nezreagovaných složek, že se zvyšují náklady na obsluhu, suroviny (benzaldehyd) a strojní zařízení. Rovněž je nutno vzít v úvahu výskyt odpadních vod se zvýšeným obsahem organických látek i zhoršení pracovního pro209256 středí v důsledku nutnosti používání benzaldehydu.The invention relates to a process for obtaining threo-1- (pnitrophenyl) -2-amino-1,3-propanediol and threo-1- (p-nitrophenyl) -2-chloroacetamido-1,3-propanediol from mother liquors after the dichloroacetylation of threo-1- (pnitrophenyl) -2-amino-1,3-propanediol, containing unreacted threo-1- (p-nitrophenyl) -2-amino-1,3-propanediol, non-crystallized threo-1- (pnitrophenyl) -2-dichloroacetamido -1,3-propanediol, unreacted and excess methyl dichloroacetate, dichloroacetic acid or hydroxyacetic acid, hydrogen chloride, methanol and water. The recovery of the two compounds is one of the basic regeneration processes in the synthesis of the antibiotic chloramphenicol. So far, classical methods have been used, ie evaporation of the mother liquor, cooling and crystallization of mixtures of both substances. In this mixture, the threo-1- (p-nitrophenyl) -2-dichloroacetamido-1,3-propanediol is then hydrolyzed to the corresponding 2-amino derivative which is ultimately converted to a sparingly soluble Schiff base, in particular by reaction with ben; zaldehyde to the corresponding benzylidene derivative. The disadvantage of this process is the fact that even when an excess of benzaldehyde is used, a significant amount of unreacted constituents remains in the solution, increasing the cost of service, raw materials (benzaldehyde) and machinery. Consideration should also be given to the occurrence of waste water with an increased content of organic substances as well as the deterioration of the working environment due to the need to use benzaldehyde.
Nověji byly studovány možnosti použití ionto! měnné techniky při regeneraci a zpracování produktů a meziproduktů syntézy chloramfenikolu. G. N. Altšuler (Chimiko farní. Ž. 1, č. 9, 54-58, 1967) stanovuje některé kinetické charakteristiky sorpce threo-l-(p-nitrofenyl)-2-amino-l,3-propandiolu z vodných roztoků na katexu a studuje možnost dělení této látky a chloridu sodného na í anexu v chloridovém cyklu, nikoliv však její oddělení od chloramfenikolu, tj. od threo-l-(p-nitrofenyl)-2-dichloracetamido-l,3-propandiolu. Citovaný autor uvádí, že lze threo-l-(p-nitrofenyl)2-amino-l,3-propandiol selektivně adsorbovat na anex v Cl-formě, desorbovat vodou a zkoncentrovat na katexu, odkud se uvolní ve formě hydrochloridu běžně provedenou desorpcí.More recently, the use of ionto! exchange techniques in the regeneration and processing of chloramphenicol synthesis products and intermediates. GN Altšuler (Chimiko farní. Ž. 1, No. 9, 54-58, 1967) determines some kinetic characteristics of sorption of threo-1- (p-nitrophenyl) -2-amino-1,3-propanediol from aqueous solutions on cation exchanger and studies the possibility of separation of this substance and sodium chloride on an anion exchange resin in the chloride cycle, but not its separation from chloramphenicol, ie from threo-1- (p-nitrophenyl) -2-dichloroacetamido-1,3-propanediol. The cited author states that threo-1- (p-nitrophenyl) 2-amino-1,3-propanediol can be selectively adsorbed to the anion exchange resin in Cl-form, desorbed with water and concentrated on a cation exchange resin from which it is released as the hydrochloride by conventional desorption.
Otázka regenerace ekonomicky zajímavých • množství cenných produktů a meziproduktů synté; zy chloramfenikolu řeší podle vynálezu způsob získávání threo-l-(p-nitrofenyl)-2-amino-l,3propandiolu a threo-l-(p-nitrofenyl)-2-dichloracétamido-l,3-propandiolu z matečných louhů po dichloracetylaci threo-l-(p-nitrofenyl)-2-amino1,3-propandiolu, obsahujících nezreagovanýThe question of the regeneration of economically interesting • quantities of valuable synthesis products and intermediates; The present invention provides a process for obtaining threo-1- (p-nitrophenyl) -2-amino-1,3-propanediol and threo-1- (p-nitrophenyl) -2-dichloroacetamido-1,3-propanediol from mother liquors after dichloroacetylation of threo -1- (p-nitrophenyl) -2-amino-1,3-propanediol containing unreacted
Ί threo-l-(p-nitrofenyl)-2-amino-l,3-propandiol, ! nevykrystalovaný threo-l-(p-nitrofenyl)-2-di209256 chloracetamino-l,3-propandiol, nezreagovaný a přebytečný dichloroctan měthylnatý, kyselinu chloroctovou, popřípadě hydroxyoctovou, chlorovodík, methanol a vodu.Threo-1- (p-nitrophenyl) -2-amino-1,3-propanediol; non-crystallized threo-1- (p-nitrophenyl) -2-di209256 chloroacetamino-1,3-propanediol, unreacted and excess methyl dichloroacetate, chloroacetic acid, optionally hydroxyacetic acid, hydrogen chloride, methanol and water.
Podstata tohoto způsobu spočívá v tom, že se matečný louh nejprve zbaví threo-l-(p-nitrofenyl)-2-dichloracetamido-l ,3-propandiolu adsorpcí na silně bázickém anexu v OH-cyklu a z roztoku prošlého anexem se zachytí threo-l-(p-nitrofenyl)-2-amino-l,3-propandiol na středně až silně kyselém katexu v H-cyklu, načež se z anexu elucí organickým rozpouštědlem nebo směsí rozpouštědel, jako alkanolem s 1 až 3 atomy uhlíku nebo esterem kyseliny octové s alkanolem s 1 až 2 atomy uhlíku, s výhodou směsí methanolu s octanem ethylnatým v poměru 1 : 1, izoluje threo-l-(p-nitrofenyl)-2-dichloracetamido-l,3-propandiol a z katexu se elucí zředěnou minerální kyselinou, například chlorovodíkovou, bromovodíkovou nebo sírovou, v koncentraci 5 až 15 %, s výhodou 10 %, za současné regenerace katexu izoluje threo- l-(p-nitrofenyl)-2-amino-1,3-propandiol ve formě roztoku soli s použitou kyselinou.The essence of this method is that the mother liquor is first freed of threo-1- (p-nitrophenyl) -2-dichloroacetamido-1,3-propanediol by adsorption on a strongly basic anion exchange resin in the OH-cycle and threo-l is collected from the anion exchange solution. - (p-nitrophenyl) -2-amino-1,3-propanediol on a medium to strongly acidic cation exchanger in the H-cycle, followed by elution from the anion exchanger with an organic solvent or solvent mixture such as a C 1 -C 3 alkanol or acetic acid ester with a C 1 -C 2 alkanol, preferably a 1: 1 mixture of methanol and ethyl acetate, isolates threo-1- (p-nitrophenyl) -2-dichloroacetamido-1,3-propanediol and elutes with a dilute mineral acid from the cation exchanger, for example, hydrochloric, hydrobromic or sulfuric acid, at a concentration of 5 to 15%, preferably 10%, while recovering the cation exchange resin, isolates the threo- 1- (p-nitrophenyl) -2-amino-1,3-propanediol in the form of a salt solution with the acid used .
Způsob podle vynálezu znamená zjednodušení technologie výroby chloramfenikolu a možnost techniky schůdné regenerace cenných meziproduktů a produktů syntézy, zlepšení pracovních podmínek, zmenšení zněěištění odpadních vod a úsporu provozních nákladů.The process according to the invention entails a simplification of the chloramphenicol production technology and the possibility of a viable regeneration technique of valuable intermediates and synthesis products, improved working conditions, reduced wastewater pollution and savings in operating costs.
Podrobnosti způsobu podle vynálezu jsou zřejmé z příkladu provedení.The details of the process according to the invention are apparent from an exemplary embodiment.
Příklad provedeníExemplary embodiment
2652 litrů vodně methanolického matečného louhu po dichloracetylaci threo-l-(p-nitrofenyl)2-amino-l,3-propandiolu, s obsahem 14,6 kg této látky, 14,6 kg threo-l-(p-nitrofenyl)-2-dichloracetamido-l,3-propandiolu, 58,4 kg dichloroctanu methylnatého a 601 kg methanolu se nechá proté-2652 liters of aqueous methanolic mother liquor after the dichloroacetylation of threo-1- (p-nitrophenyl) 2-amino-1,3-propanediol, containing 14,6 kg of this substance, 14,6 kg of threo-1- (p-nitrophenyl) - Of 2-dichloroacetamido-1,3-propanediol, 58.4 kg of methyl dichloroacetate and 601 kg of methanol are allowed to flow through.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS265376A CS209256B1 (en) | 1976-04-22 | 1976-04-22 | Method of winning of threo-1-/p-nitrophenyl/-2-amino-1,3-propandioli and threo-1-/p-nitrophenyl/-2-dichlor acetamido-1,3-propandiole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS265376A CS209256B1 (en) | 1976-04-22 | 1976-04-22 | Method of winning of threo-1-/p-nitrophenyl/-2-amino-1,3-propandioli and threo-1-/p-nitrophenyl/-2-dichlor acetamido-1,3-propandiole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS209256B1 true CS209256B1 (en) | 1981-11-30 |
Family
ID=5364280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS265376A CS209256B1 (en) | 1976-04-22 | 1976-04-22 | Method of winning of threo-1-/p-nitrophenyl/-2-amino-1,3-propandioli and threo-1-/p-nitrophenyl/-2-dichlor acetamido-1,3-propandiole |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS209256B1 (en) |
-
1976
- 1976-04-22 CS CS265376A patent/CS209256B1/en unknown
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