CH645340A5 - Verfahren zur herstellung von reinem, lagerbestaendigem acetoacetamid. - Google Patents
Verfahren zur herstellung von reinem, lagerbestaendigem acetoacetamid. Download PDFInfo
- Publication number
- CH645340A5 CH645340A5 CH738681A CH738681A CH645340A5 CH 645340 A5 CH645340 A5 CH 645340A5 CH 738681 A CH738681 A CH 738681A CH 738681 A CH738681 A CH 738681A CH 645340 A5 CH645340 A5 CH 645340A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acetoacetamide
- diketene
- ammonia
- excess
- reaction
- Prior art date
Links
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 title claims description 39
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 52
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 32
- 229910021529 ammonia Inorganic materials 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 6
- 239000012452 mother liquor Substances 0.000 claims description 6
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- UAUSQEVPWPGBHG-IHWYPQMZSA-N (z)-3-aminobut-2-enamide Chemical compound C\C(N)=C\C(N)=O UAUSQEVPWPGBHG-IHWYPQMZSA-N 0.000 claims description 2
- ULZPHVRGOPLRGP-UHFFFAOYSA-N 3-acetyl-4-hydroxy-6-methyl-1h-pyridin-2-one Chemical compound CC(=O)C1=C(O)NC(C)=CC1=O ULZPHVRGOPLRGP-UHFFFAOYSA-N 0.000 claims description 2
- KXAZVCRSYYAAAX-UHFFFAOYSA-N 5-acetyl-6-hydroxy-4-methyl-1H-pyridin-2-one Chemical compound CC(=O)C=1C(C)=CC(=O)NC=1O KXAZVCRSYYAAAX-UHFFFAOYSA-N 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 230000003405 preventing effect Effects 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 239000012429 reaction media Substances 0.000 claims 3
- 239000007788 liquid Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- QMDFHZOGAYONLN-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridine-3-carboxylic acid Chemical compound OC(=O)C1CNC=CC1 QMDFHZOGAYONLN-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000009257 reactivity Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000000725 suspension Substances 0.000 description 9
- 239000006286 aqueous extract Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic chlorinated hydrocarbons Chemical class 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- UKVYVZLTGQVOPX-IHWYPQMZSA-N (z)-3-aminobut-2-enoic acid Chemical compound C\C(N)=C\C(O)=O UKVYVZLTGQVOPX-IHWYPQMZSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical class CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 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
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B04—CENTRIFUGAL APPARATUS OR MACHINES FOR CARRYING-OUT PHYSICAL OR CHEMICAL PROCESSES
- B04B—CENTRIFUGES
- B04B5/00—Other centrifuges
- B04B5/10—Centrifuges combined with other apparatus, e.g. electrostatic separators; Sets or systems of several centrifuges
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/90—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813101650 DE3101650C2 (de) | 1981-01-20 | 1981-01-20 | Verfahren zur Herstellung von reinem, lagerbeständigem Acetoacetamid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH645340A5 true CH645340A5 (de) | 1984-09-28 |
Family
ID=6122957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH738681A CH645340A5 (de) | 1981-01-20 | 1981-11-17 | Verfahren zur herstellung von reinem, lagerbestaendigem acetoacetamid. |
Country Status (4)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2777590A1 (fr) | 1998-04-15 | 1999-10-22 | Midi Moulages Plast | Dispositif anti-relevage de securite de volet roulant |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3335425A1 (de) * | 1983-09-29 | 1985-04-18 | Wacker-Chemie GmbH, 8000 München | Verfahren zur stabilisierung waessriger loesungen von acetoacetamiden unter gleichzeitiger verminderung des gehaltes an ss-aminocrotonsaeureamiden |
| US5025106A (en) * | 1990-10-22 | 1991-06-18 | Eastman Kodak Company | Preparation of aqueous solutions of acetoacetamide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7201363A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-02-12 | 1972-08-15 |
-
1981
- 1981-01-20 DE DE19813101650 patent/DE3101650C2/de not_active Expired
- 1981-11-02 IN IN1220/CAL/81A patent/IN156500B/en unknown
- 1981-11-17 CH CH738681A patent/CH645340A5/de not_active IP Right Cessation
-
1982
- 1982-01-20 JP JP620982A patent/JPS57139045A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2777590A1 (fr) | 1998-04-15 | 1999-10-22 | Midi Moulages Plast | Dispositif anti-relevage de securite de volet roulant |
Also Published As
| Publication number | Publication date |
|---|---|
| IN156500B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-08-17 |
| JPS57139045A (en) | 1982-08-27 |
| DE3101650C2 (de) | 1984-11-08 |
| DE3101650A1 (de) | 1982-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |