DE705641C - Process for the production of carboxylic acid anhydrides - Google Patents
Process for the production of carboxylic acid anhydridesInfo
- Publication number
- DE705641C DE705641C DEA76525D DEA0076525D DE705641C DE 705641 C DE705641 C DE 705641C DE A76525 D DEA76525 D DE A76525D DE A0076525 D DEA0076525 D DE A0076525D DE 705641 C DE705641 C DE 705641C
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- acid anhydrides
- carboxylic acid
- production
- 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
- 238000000034 method Methods 0.000 title claims description 10
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 title claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 229940071125 manganese acetate Drugs 0.000 claims description 5
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052753 mercury Inorganic materials 0.000 claims 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 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052770 Uranium Inorganic materials 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
- 150000008064 anhydrides Chemical class 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 229940078494 nickel acetate Drugs 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Carbonsäureanhydriden Gegenstand des Patents 69q.699 ist ein Verfahren zur Herstellung von Carbonsäureanhydriden, gemäß welchem die Aldehyde von Carbonsäuren in die entsprechenden Säureanhydride übergeführt werden, gegebenenfalls in Gegenwart von Manganacetat.Process for the preparation of carboxylic acid anhydrides Patent 69q.699 is a process for the preparation of carboxylic acid anhydrides, according to which the aldehydes of carboxylic acids are converted into the corresponding acid anhydrides , optionally in the presence of manganese acetate.
Bei weiterer Bearbeitung dieses Verfahrens wurde nun gefunden, daß an Stelle von Manganacetat auch das Acetat eines anderen Metalls verwendet werden kann; besonders das Acetat von solchen Metallen, welche mehrere Wertigkeitsstufen bilden. Es wurde weiter gefunden, daß die Verwendung mehrerer Metallacetate in Mischung miteinander, wobei die Mischung such Manganacetat enthalten kann, unter Umständen Vorteile hinsichtlich des Reaktionsverlaufes mit sich bringen kann.Further processing of this process has now found that Instead of manganese acetate, the acetate of another metal can also be used can; especially the acetate of those metals which have several degrees of valence form. It was further found that the use of several metal acetates in a mixture with each other, whereby the mixture can also contain manganese acetate, under certain circumstances Can bring advantages with regard to the course of the reaction.
Als Beispiele seien genannt die Acetate von Kobalt, Nickel, Quecksilber, Natrium, Uran, Zinn und Silber.Examples are the acetates of cobalt, nickel, mercury, Sodium, uranium, tin and silver.
Beispiele i. In ein mit Kühlvorrichtung versehenes Rührgefäß werden 7o Gewichtsteile Eisessig mit 2 Gewichtsteilen Mangan-, 2 Gewichtsteilen Kobalt- und 2 Gewichtsteilen Nickelacetat vorgelegt und dazu 4oo Gewichtsteile Acetaldehyd gegeben. Bei einem Druck von 2 Atü und 3o bis 5o° wird so lange Sauerstoff eingeleitet, bis die Oxydation beendet ist. Es werden 40% des angewandten Acetaldehyds zu Anhydrid umgesetzt.Examples i. In a stirred vessel provided with a cooling device 7o parts by weight of glacial acetic acid with 2 parts by weight of manganese, 2 parts by weight of cobalt and 2 parts by weight of nickel acetate and 400 parts by weight of acetaldehyde given. At a pressure of 2 atmospheres and 3o to 5o °, oxygen is introduced as long as until the oxidation is complete. 40% of the acetaldehyde used becomes anhydride implemented.
Durch fraktionierte Vakuumdestillation können etwa 35% des theoretisch aus dem angewandten Aldehyd zu erwartenden Anhydrids in reiner Form erhalten werden.By fractional vacuum distillation, about 35% of the theoretical can be obtained from the applied aldehyde expected anhydride in pure form.
2. Arbeitsweise wie Beispiel i; es werden jedoch 4oo Gewichtsteile Eisessig vorgelegt mit i, 5 Gewichtsteilen Mangan-, 6 Gewichtsteilen Kobalt-, o, i Gewichtsteilen Quecksilber- und o,2 Gewichtsteilen Natriumacetat und ioo Gewichtsteile Acetaldehyd zugegeben; Ausbeute 49% Anhydrid.2. Procedure as in example i; however, it becomes 400 parts by weight Glacial acetic acid presented with 1.5 parts by weight of manganese, 6 parts by weight of cobalt, o, i parts by weight of mercury and 0.2 parts by weight of sodium acetate and 100 parts by weight Acetaldehyde added; Yield 49% anhydride.
Nach der im Beispiel i am Schluß beschriebenen Arbeitsweise kann man 42,5% der Theorie an Reinanhydrid isolieren.After the procedure described in Example i at the end, one can Isolate 42.5% of theory of pure anhydride.
3. In einem mit entsprechenden Kühlvorrichtungen versehenen Reaktionsturm
wird ein Gemisch von 264 Gewichtsteilen Acetaldehyd und 6oo Gewichtsteilen Eisessig,
in welchem 6 Gewichtsteile Kobaltacetat gelöst
sind, im Laufe i
Stunde kontinuierlich eingetragen, und gleichzeitig werden kontinuierlich unter
guter Durchmischung 96 Gewichtsteile Sauer-
Nach der im Beispiel i am Schluß beschriebenen Arbeitsweise kann man 39% der Theorie an Reinanhydrid isolieren.After the procedure described in Example i at the end, one can Isolate 39% of theory of pure anhydride.
4. Arbeitsweise wie bei Beispiel 3; es werden 0,74 Gewichtsteile Kobalt- und 0,74 Gewichtsteile Nickelacetat zugegeben; Ausbeute 520;`o des oxydierten Acetaldehyds in Form von Anhydrid. Nach der im Beispiel i am Schluß beschriebenen Arbeitsweise kann man 45% der Theorie an Reinanhydrid isolieren.4. Procedure as in Example 3; 0.74 parts by weight of cobalt and 0.74 parts by weight of nickel acetate are added; Yield 520; `o of the oxidized acetaldehyde in the form of anhydride. 45% of theory of pure anhydride can be isolated using the procedure described at the end in Example i.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA76525D DE705641C (en) | 1934-02-02 | 1934-02-02 | Process for the production of carboxylic acid anhydrides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA76525D DE705641C (en) | 1934-02-02 | 1934-02-02 | Process for the production of carboxylic acid anhydrides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE705641C true DE705641C (en) | 1941-05-05 |
Family
ID=6946812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA76525D Expired DE705641C (en) | 1934-02-02 | 1934-02-02 | Process for the production of carboxylic acid anhydrides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE705641C (en) |
-
1934
- 1934-02-02 DE DEA76525D patent/DE705641C/en not_active Expired
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