DE863040C - Verfahren zur Herstellung von Acetylaceton - Google Patents
Verfahren zur Herstellung von AcetylacetonInfo
- Publication number
- DE863040C DE863040C DED11085A DED0011085A DE863040C DE 863040 C DE863040 C DE 863040C DE D11085 A DED11085 A DE D11085A DE D0011085 A DED0011085 A DE D0011085A DE 863040 C DE863040 C DE 863040C
- Authority
- DE
- Germany
- Prior art keywords
- acetone
- ethyl acetate
- acetylacetone
- alkali metals
- alkali
- 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
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 21
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 4
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 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 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- -1 alcohols alkali metals Chemical class 0.000 description 1
- RAWGYCTZEBNSTP-UHFFFAOYSA-N aluminum potassium Chemical compound [Al].[K] RAWGYCTZEBNSTP-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- XSBOOIFPDDTOMH-UHFFFAOYSA-N pentane-2,4-dione;sodium Chemical compound [Na].CC(=O)CC(C)=O XSBOOIFPDDTOMH-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- UAKCMIIOSJFOTD-UHFFFAOYSA-M sodium;3-oxobutanoate Chemical compound [Na+].CC(=O)CC([O-])=O UAKCMIIOSJFOTD-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
- Verfahren zur Herstellung von Acetylaceton Im Patent 824 040 ist ein Verfahren zur Herstellung von Acetylaceton aus Aceton, Essigester und Al.kalialkoholat angegeben, welches im wesentlichen darin besteht, daß zu einem Gemisch von Alikalialkoholat und Essigester bei erhöhter Temperatur, zweckmäßig bei 3o bis 5o°, allmählich Aceton, vorteilhaft gleichzeitig mit Essigester, zugesetzt wird, und sobald der Gehalt des Umsetzungsgemisches an Aceton geringe Mengen übersteigt, dieser zusammen mit Alkohol abdestilliert wird, wobei Alkohol, Essigester und Aceton übergehen, während Acetylacetonnatrium und gegebenenfalls Acetessigesternatrium zurückbleiben, worauf das Gemisch durch Ansäuern und fraktionierte Destillation in bekannter Weise zerlegt wird. Es wurde nun gefunden, daß eine Erhöhung der Ausbeute erzielt werden kann, wenn unter Beibehaltung .des Verfahrens gemäß dem Hauptpatent anstatt Alkalialkohole Alkalimetalle oder -hydride, z.. B-. Natrium bzw. Natriumhydrid, verwendet werden. Die Verwendung der Alkalimetalle wird wesentlich erleichtert, wenn sie in Form von Emulsionen in indifferenten Flüssigkeiten zur Anwendung kommen. Die Alkalimetalle bzw. -hydride werden portionsweise dem -Umsetzungsgemisch zugesetzt. Ferner kann der Essigester, wie noch festgestellt wurde, von Anfang an Aceton enthalten, so daß von einem Gemisch von Alkalimetallen bzw. -hydrilden, Essigester und Aceton ausgegangen wird. Allerdings soll vermieden werden, daß der Gehalt des Umsetzungsgemisches an Aceton bei der folgenden Zugabe des Ess;,gester-Aceton-Gemisches erheblich ansteigt; das Aceton wird dann, sobald dies der Fall ist, nach Verbrauch des Natriums bzw. Natriumhydrnds mit Alkohol abdestilliert.
Claims (3)
- PATENTANSPRÜCHE: i. Abänderung des. Verfahrens zur Herstellung von Acetylaceton aus Aceton, Essigester und Alkalialkoholat bei erhöhter Temperatur gemäß Patent 8124 040, dadurch gekennzeichnet, daß an Stelle von Alkalialkoholaten Alkalimetalle oder -hy,dride verwendet werden.
- 2. Verfahren nach Anspruch i, dadurch gekennzeichnet, dtaß die Alkalimetalle in einer inerten Flüssigkeit emulgiert verwendet- werden.
- 3. Verfahren nach Anspruch i und 2, dadurch gekennzeichnet, daß von einem Gemisch aus Alkalimetallen bzw. -hydriden, Essigester und Aceton ausgegangen wird.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED11085A DE863040C (de) | 1951-12-11 | 1951-12-11 | Verfahren zur Herstellung von Acetylaceton |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED11085A DE863040C (de) | 1951-12-11 | 1951-12-11 | Verfahren zur Herstellung von Acetylaceton |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE863040C true DE863040C (de) | 1953-01-15 |
Family
ID=7033621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED11085A Expired DE863040C (de) | 1951-12-11 | 1951-12-11 | Verfahren zur Herstellung von Acetylaceton |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE863040C (de) |
-
1951
- 1951-12-11 DE DED11085A patent/DE863040C/de not_active Expired
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