DE3101650C2 - Verfahren zur Herstellung von reinem, lagerbeständigem Acetoacetamid - Google Patents
Verfahren zur Herstellung von reinem, lagerbeständigem AcetoacetamidInfo
- Publication number
- DE3101650C2 DE3101650C2 DE19813101650 DE3101650A DE3101650C2 DE 3101650 C2 DE3101650 C2 DE 3101650C2 DE 19813101650 DE19813101650 DE 19813101650 DE 3101650 A DE3101650 A DE 3101650A DE 3101650 C2 DE3101650 C2 DE 3101650C2
- Authority
- DE
- Germany
- Prior art keywords
- acetoacetamide
- diketene
- excess
- ammonia
- temperatures
- 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.)
- Expired
Links
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 54
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000725 suspension Substances 0.000 abstract description 10
- 239000006286 aqueous extract Substances 0.000 abstract description 7
- 239000011541 reaction mixture Substances 0.000 abstract description 5
- -1 aliphatic chlorinated hydrocarbons Chemical class 0.000 abstract description 2
- 238000005119 centrifugation Methods 0.000 abstract description 2
- 238000004140 cleaning Methods 0.000 abstract description 2
- 230000006641 stabilisation Effects 0.000 abstract description 2
- 238000011105 stabilization Methods 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- RIVCNRZZXJLAHE-UHFFFAOYSA-N 2,4-dimethyl-6-oxo-1h-pyridine-3-carboxamide Chemical compound CC1=CC(=O)NC(C)=C1C(N)=O RIVCNRZZXJLAHE-UHFFFAOYSA-N 0.000 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 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 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
- 230000000087 stabilizing effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 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
- 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 description 1
- LQSXKWKNDWKEHE-UHFFFAOYSA-N 3-oxobutanamide;sodium Chemical compound [Na].CC(=O)CC(N)=O LQSXKWKNDWKEHE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000003405 preventing effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 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)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813101650 DE3101650C2 (de) | 1981-01-20 | 1981-01-20 | Verfahren zur Herstellung von reinem, lagerbeständigem Acetoacetamid |
| IN1220/CAL/81A IN156500B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-01-20 | 1981-11-02 | |
| CH738681A CH645340A5 (de) | 1981-01-20 | 1981-11-17 | Verfahren zur herstellung von reinem, lagerbestaendigem acetoacetamid. |
| JP620982A JPS57139045A (en) | 1981-01-20 | 1982-01-20 | Manufacture of pure storage-stable acetoacetamide |
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 (2)
| Publication Number | Publication Date |
|---|---|
| DE3101650A1 DE3101650A1 (de) | 1982-08-26 |
| DE3101650C2 true DE3101650C2 (de) | 1984-11-08 |
Family
ID=6122957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813101650 Expired DE3101650C2 (de) | 1981-01-20 | 1981-01-20 | Verfahren zur Herstellung von reinem, lagerbeständigem Acetoacetamid |
Country Status (4)
Families Citing this family (3)
| 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 |
| FR2777590B1 (fr) | 1998-04-15 | 2000-06-16 | Midi Moulages Plast | Dispositif anti-relevage de securite de volet roulant |
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
Also Published As
| Publication number | Publication date |
|---|---|
| IN156500B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-08-17 |
| JPS57139045A (en) | 1982-08-27 |
| DE3101650A1 (de) | 1982-08-26 |
| CH645340A5 (de) | 1984-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07C103/127 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |