DE1445149A1 - Verfahren zur Herstellung von L-alpha-Aminolactam aus einem Gemisch von D- und L-alpha-Aminolactam - Google Patents
Verfahren zur Herstellung von L-alpha-Aminolactam aus einem Gemisch von D- und L-alpha-AminolactamInfo
- Publication number
- DE1445149A1 DE1445149A1 DE19601445149 DE1445149A DE1445149A1 DE 1445149 A1 DE1445149 A1 DE 1445149A1 DE 19601445149 DE19601445149 DE 19601445149 DE 1445149 A DE1445149 A DE 1445149A DE 1445149 A1 DE1445149 A1 DE 1445149A1
- Authority
- DE
- Germany
- Prior art keywords
- aminolactam
- salt
- pyrrolidonecarboxylic acid
- solution
- liquid
- 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
- 238000000034 method Methods 0.000 title claims description 31
- 239000000203 mixture Substances 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000007788 liquid Substances 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 29
- 239000000243 solution Substances 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000002798 polar solvent Substances 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 10
- 229940079889 pyrrolidonecarboxylic acid Drugs 0.000 claims description 10
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 150000002500 ions Chemical class 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- DQAKJEWZWDQURW-UHFFFAOYSA-N pyrrolidonecarboxylic acid Chemical compound OC(=O)N1CCCC1=O DQAKJEWZWDQURW-UHFFFAOYSA-N 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 230000029142 excretion Effects 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- CBCIHIVRDWLAME-UHFFFAOYSA-N hexanitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O CBCIHIVRDWLAME-UHFFFAOYSA-N 0.000 claims 1
- 150000003951 lactams Chemical class 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 7
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Natural products O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 235000013405 beer Nutrition 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YJUFCXMAKCLEJZ-UHFFFAOYSA-N [C].N1C(CCC1)=O Chemical compound [C].N1C(CCC1)=O YJUFCXMAKCLEJZ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- AXVNRAPIEOXCTC-UHFFFAOYSA-N azane;pyrrolidin-2-one Chemical compound N.O=C1CCCN1 AXVNRAPIEOXCTC-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007958 sleep Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
- C07D223/12—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL241310 | 1959-07-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1445149A1 true DE1445149A1 (de) | 1969-01-23 |
Family
ID=19751831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19601445149 Pending DE1445149A1 (de) | 1959-07-15 | 1960-07-14 | Verfahren zur Herstellung von L-alpha-Aminolactam aus einem Gemisch von D- und L-alpha-Aminolactam |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE593068A (enrdf_load_stackoverflow) |
| CH (1) | CH391709A (enrdf_load_stackoverflow) |
| DE (1) | DE1445149A1 (enrdf_load_stackoverflow) |
| ES (1) | ES259646A1 (enrdf_load_stackoverflow) |
| FI (1) | FI40542B (enrdf_load_stackoverflow) |
| GB (1) | GB954207A (enrdf_load_stackoverflow) |
| LU (1) | LU38944A1 (enrdf_load_stackoverflow) |
| SE (1) | SE301808B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6606261A (enrdf_load_stackoverflow) * | 1966-05-07 | 1967-11-08 |
-
1960
- 1960-07-12 GB GB2428560A patent/GB954207A/en not_active Expired
- 1960-07-13 LU LU38944D patent/LU38944A1/xx unknown
- 1960-07-13 SE SE687060A patent/SE301808B/xx unknown
- 1960-07-14 ES ES0259646A patent/ES259646A1/es not_active Expired
- 1960-07-14 DE DE19601445149 patent/DE1445149A1/de active Pending
- 1960-07-14 CH CH805160A patent/CH391709A/de unknown
- 1960-07-15 BE BE593068A patent/BE593068A/fr unknown
- 1960-07-15 FI FI121060A patent/FI40542B/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| LU38944A1 (enrdf_load_stackoverflow) | 1960-10-08 |
| ES259646A1 (es) | 1960-12-16 |
| CH391709A (de) | 1965-05-15 |
| GB954207A (en) | 1964-04-02 |
| BE593068A (fr) | 1960-10-31 |
| SE301808B (enrdf_load_stackoverflow) | 1968-06-24 |
| FI40542B (enrdf_load_stackoverflow) | 1968-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH641432A5 (de) | Verfahren zur aufspaltung von racemischer 6-methoxy-alpha-methyl-2-naphthalinessigsaeure in die optischen antipoden. | |
| DE3043766A1 (de) | Verfahren zur wiedergewinnung von carbonsaeuren | |
| DE3334863A1 (de) | Verfahren zur gewinnung von waessrigen glyoxylsaeureloesungen | |
| DE60115954T2 (de) | Verfahren zur herstellung von gabapentin | |
| DE2530386B2 (de) | Verfahren zum entfernen von von aussen in ein xylan- hydrolyse- und xylose-extraktionssystem zugefuehrter starker saeure und von bei der hydrolyse entstandener essigsaeure und ameisensaeure aus der erzeugten, diese komponenten enthaltenden waessrigen xyloseloesung unter verwendung von ionenaustauschern | |
| DE1542249A1 (de) | Verfahren zum Herstellen eines Metallsalzes aus einem Metallchlorid und einer Saeure | |
| DE68911727T2 (de) | Ionenaustausch-Gewinnung von L-Lysin. | |
| DE1445149A1 (de) | Verfahren zur Herstellung von L-alpha-Aminolactam aus einem Gemisch von D- und L-alpha-Aminolactam | |
| EP0505596B1 (de) | Verfahren zur Herstellung eines Feuchthaltemittels | |
| DE2700851C3 (de) | Verfahren zur getrennten Gewinnung geradkettiger und verzweigter Carbonsäuren mit 8 bis 22 Kohlenstoffatomen aus Gemischen wasserlöslicher geradkettiger und verzweigter Carbonsäuren | |
| DE1814575C3 (de) | Verfahren zur Gewinnung von optisch aktivem Lysin sowie das DL-, D- und L-Lysinphenoxyacetat | |
| DE1949585C3 (de) | Verfahren zur Gewinnung von L-Lysin oder einem Säureadditionssalz davon aus DL-Lysin | |
| DE1038052B (de) | Verfahren zur Gewinnung von Aminocarbonsaeuren, ª‡, ªÏ-Dicarbonsaeuren und ª‡, ªÏ-Diaminen aus Polyamiden | |
| DE2556040A1 (de) | Antipodentrennverfahren und verbindungen | |
| DE3342984A1 (de) | Verfahren zur isolierung von alkalisulfat-armen paraffinsulfonaten und schwefelsaeure aus paraffin-sulfoxidation-reaktionsgemischen | |
| DE1927698C3 (de) | Verfahren zur Gewinnung von optisch aktivem Lysin | |
| DE1518353C3 (de) | Verfahren zur Herstellung von optisch aktivem Lysin oder einer Ver bindung desselben | |
| DE654025C (de) | Verfahren zur Trennung von in Wasser leicht loeslichen Aminosaeuren und Ammoniumsulfat | |
| DE977347C (de) | Verfahren zum Reinigen von waessrigen Loesungen von rohen Caprolactamloesungen | |
| DE860054C (de) | Verfahren zur Herstellung von aliphatischen Diaminen oder ihren N-substituierten Abkoemmlingen | |
| DE2230794C3 (de) | Verfahren zur Trennung von Orthophosphorsäuremono- und di'estern | |
| DE1543546A1 (de) | Verfahren zur Herstellung von Cholinsalzen | |
| DE505460C (de) | Verfahren zur Darstellung optisch aktiver aromatischer Aminoalkohole | |
| DE951366C (de) | Verfahren zur Herstellung von 1-Phenyl-2, 3, 4-trimethylpyrazolon-(5) | |
| DE1092018B (de) | Verfahren zur Gewinnung von lactamoligomerhaltigen Lactamen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |