DE2163939A1 - Alkalimetallhalbsalze von 2-Pyrrolidon-5-carbonsäure und Verfahren zu ihrer Herstellung - Google Patents
Alkalimetallhalbsalze von 2-Pyrrolidon-5-carbonsäure und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2163939A1 DE2163939A1 DE19712163939 DE2163939A DE2163939A1 DE 2163939 A1 DE2163939 A1 DE 2163939A1 DE 19712163939 DE19712163939 DE 19712163939 DE 2163939 A DE2163939 A DE 2163939A DE 2163939 A1 DE2163939 A1 DE 2163939A1
- Authority
- DE
- Germany
- Prior art keywords
- pyrrolidone
- carboxylic acid
- alkali metal
- pca
- salts
- 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
- 150000003839 salts Chemical class 0.000 title claims description 20
- ODHCTXKNWHHXJC-UHFFFAOYSA-N 5-oxoproline Chemical class OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 title claims description 18
- 229910052783 alkali metal Inorganic materials 0.000 title claims description 13
- 150000001340 alkali metals Chemical class 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 3
- 239000011734 sodium Substances 0.000 claims description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 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 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000001914 filtration Methods 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000003321 atomic absorption spectrophotometry Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 229960002989 glutamic acid Drugs 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 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 description 1
- MMDZBDLRGFUSSP-UHFFFAOYSA-N 3-(2,5-dioxoimidazolidin-4-yl)propanenitrile Chemical compound O=C1NC(CCC#N)C(=O)N1 MMDZBDLRGFUSSP-UHFFFAOYSA-N 0.000 description 1
- 238000007696 Kjeldahl method Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- -1 alkali metal cation Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Pyrrole Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12745670A JPS4926623B1 (enrdf_load_stackoverflow) | 1970-12-29 | 1970-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2163939A1 true DE2163939A1 (de) | 1972-07-20 |
Family
ID=14960365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712163939 Pending DE2163939A1 (de) | 1970-12-29 | 1971-12-22 | Alkalimetallhalbsalze von 2-Pyrrolidon-5-carbonsäure und Verfahren zu ihrer Herstellung |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4926623B1 (enrdf_load_stackoverflow) |
| CA (1) | CA957378A (enrdf_load_stackoverflow) |
| DE (1) | DE2163939A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2120926A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1331727A (enrdf_load_stackoverflow) |
| IT (1) | IT1033060B (enrdf_load_stackoverflow) |
| NL (1) | NL7118024A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3735263C1 (de) * | 1987-10-17 | 1988-08-25 | Degussa | Verfahren zur Herstellung von Alkalimetallsalzen der L-2-Pyrrolidon-5-carbonsaeure |
-
1970
- 1970-12-29 JP JP12745670A patent/JPS4926623B1/ja active Pending
-
1971
- 1971-12-22 DE DE19712163939 patent/DE2163939A1/de active Pending
- 1971-12-22 GB GB5969171A patent/GB1331727A/en not_active Expired
- 1971-12-27 FR FR7146821A patent/FR2120926A5/fr not_active Expired
- 1971-12-28 IT IT3304171A patent/IT1033060B/it active
- 1971-12-29 CA CA131,347A patent/CA957378A/en not_active Expired
- 1971-12-29 NL NL7118024A patent/NL7118024A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3735263C1 (de) * | 1987-10-17 | 1988-08-25 | Degussa | Verfahren zur Herstellung von Alkalimetallsalzen der L-2-Pyrrolidon-5-carbonsaeure |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4926623B1 (enrdf_load_stackoverflow) | 1974-07-10 |
| IT1033060B (it) | 1979-07-10 |
| NL7118024A (enrdf_load_stackoverflow) | 1972-07-03 |
| CA957378A (en) | 1974-11-05 |
| FR2120926A5 (enrdf_load_stackoverflow) | 1972-08-18 |
| GB1331727A (en) | 1973-09-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2359333A1 (de) | Verfahren zur herstellung eines dopapraeparats | |
| DE2449840A1 (de) | Adamantylamidine und verfahren zu ihrer herstellung | |
| DE2163939A1 (de) | Alkalimetallhalbsalze von 2-Pyrrolidon-5-carbonsäure und Verfahren zu ihrer Herstellung | |
| DE1518110A1 (de) | Verfahren zur Herstellung von Trialkalimetallnitriloctriacetat | |
| DE3104997A1 (de) | Verfahren zur herstellung von waessrigen natriummethioninat-loesungen (a) | |
| DE2625631C3 (de) | Verfahren zur Herstellung von Alkaligoldsulfit | |
| DE2166270C3 (de) | Nicotinoylaminoäthansulfonyl-2amino-thiazol | |
| DE1620332A1 (de) | Verfahren zur Herstellung von 5-ss-Methylmercaptoaethylhydantoin | |
| DE72222C (de) | Verfahren zur Darstellung von /Ji /?3 - Naphtylendiaminmonosulfosäure | |
| DE2433889C2 (de) | Verfahren zur Herstellung reiner allcls-Cyclopentan-1,2,3,4-tetracarbonsäure bzw. ihre Salze | |
| DE2006967B2 (de) | Verfahren zur herstellung von allantoin-polygalacturonsaeure-verbindungen | |
| DE2605567C3 (de) | Verfahren zur Gewinnung von optisch aktivem a Phenylglycin-hydrochlorid | |
| DE1961289A1 (de) | Technisches Verfahren zum Jodieren aromatischer Verbindungen unter Verwendung neuer Jodierungsreagenzien | |
| DE2260208A1 (de) | Herstellung von alkalihydrosulfiten | |
| DE2244673A1 (de) | Verfahren zur herstellung von trichlorisocyanursaeure | |
| DE2044680A1 (de) | Verfahren zur Racemisierung von optisch aktivem Ammonium N acetyl alpha aminophenyl acetat | |
| DE2701253A1 (de) | Verfahren zur herstellung von basischem kupfer (ii)-sulfat | |
| DE399904C (de) | Verfahren zur Herstellung von organischen Quecksilberverbindungen | |
| DE2705247C2 (de) | Verfahren zur Herstellung von wasserlöslichen Alkalimetall- bzw. Ammonium-Eisen (III)-Komplexsalzen von Aminopolycarbonsäuren | |
| DE3309762C1 (de) | Verfahren zur Herstellung von D,L-Homocystin (II) | |
| DE1518050C (de) | Verfahren zur Herstellung \ on Methio ninmethylsulfoniumsalzen | |
| DE693145C (de) | Verfahren zur Herstellung von d-Glutaminsaeure | |
| DE2241875A1 (de) | Herstellung von lysin | |
| CH329716A (de) | Verfahren zur Reinigung von Bis-(B-oxyäthyl)-terephthalat | |
| AT165079B (de) | Verfahren zur Herstellung von Trimethyl-(beta-jodäthyl)-ammoniumjodid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |