DE708822C - Process for the production of carboxylic acid anhydrides - Google Patents
Process for the production of carboxylic acid anhydridesInfo
- Publication number
- DE708822C DE708822C DEA84420D DEA0084420D DE708822C DE 708822 C DE708822 C DE 708822C DE A84420 D DEA84420 D DE A84420D DE A0084420 D DEA0084420 D DE A0084420D DE 708822 C DE708822 C DE 708822C
- Authority
- DE
- Germany
- Prior art keywords
- acid anhydrides
- carboxylic acid
- production
- anhydride
- acetate
- 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 5
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 229940011182 cobalt acetate Drugs 0.000 claims description 3
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 3
- 229940071125 manganese acetate Drugs 0.000 claims description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000011572 manganese Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 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
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 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)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Carbonsäureanhydriden Gegenstand des Patents 705 641 ist ein Verfahren zur Herstellung von Carbonsäureanhydriden, gemäß welchem Aldehyde in die entsprechenden Säureanhydride übergeführt werden, und zwar in Gegenwart von Acetaten der Metalle, wie z. B. Kobalt, Nickel, Quecksilber, Natrium, Uran, Zinn und Silber.Process for the production of carboxylic acid anhydrides The subject of the patent 705 641 is a process for the production of carboxylic acid anhydrides, according to which aldehydes are converted into the corresponding acid anhydrides, in the presence of acetates of the metals, such as. B. cobalt, nickel, mercury, sodium, uranium, tin and silver.
Bei weiterer Bearbeitung dieses Verfahrens wurde nun gefunden, daß das bisher nicht genannte Acetat des Kupfers eine ausgesprochene Sonderstellung einnimmt und es mit Hilfe dieses Katalysators gelingt, die Ausbeute an Anhydrid noch ganz wesentlich zu steigern.Further processing of this process has now found that the previously unmentioned copper acetate has a very special position occupies and it succeeds with the help of this catalyst, the yield of anhydride can still be increased significantly.
Das Kupferacetat wird zusammen mit Mangan- und bzw. oder Kobaltacetat angewandt. Beispiel In -ein mit kräftigen Kühlvorrichtungen ausgestattetes Rührgefäß werden 72o Gewichtsteile Eisessig vorgelegt und nach Zugabe von 6 Gewichtsteilen Kupfer- und 5 Gewichtsteilen Kobaltacetat 18o Gewichtsteile Acetaldehyd zugefügt. Es wird bei einer Temperatur von q.2° und einem Überdruck von etwa i Atm. Sauerstoff eingeleitet, so daß die Umsetzung des Aldehyds nach 23 Minuten beendet ist.The copper acetate is used together with manganese and / or cobalt acetate applied. Example In -a stirred vessel equipped with powerful cooling devices 72o parts by weight of glacial acetic acid are presented and after adding 6 parts by weight Copper and 5 parts by weight of cobalt acetate 18o parts by weight of acetaldehyde were added. It is at a temperature of q.2 ° and an overpressure of about 1 atm. oxygen initiated so that the reaction of the aldehyde is complete after 23 minutes.
Hierauf wird das Reaktionsgemisch schnell auf .etwa - i o' heruntergekühlt.The reaction mixture is then rapidly cooled down to about - i o '.
Es werden etwa 8o0;0 des angewandten Aldehyds zu Essigsäureanhydrid umgesetzt. Durch fraktionierte Vakuumdestillation können etwa 7q.o/o des theoretisch aus dem angewandten, Aldehyd zu erwartenden Anhydrids in reiner Form erhalten werden.About 80.0 of the aldehyde used turns into acetic anhydride implemented. By fractional vacuum distillation, about 7q.o / o of the theoretical can be obtained in pure form from the applied aldehyde expected anhydride.
Wird in dem vorstehenden .Beispiel das Kupferacetat durch die gleiche Menge Mangan.acetat ersetzt, so erhält man unter sonst gleichen Reaktionsbedingungen im Reaktionsgelnisch nur etwa .190'0 Ausbeute an Anhydrid. Durch Vakuumdestillation können nur etwa 450 'o Rein.anhydrid gewonnen werden.In the previous example, the copper acetate is replaced by the same Replaced amount of manganese acetate is obtained under otherwise identical reaction conditions in the reaction gel niche only about .190,0 yield of anhydride. By Only about 450% pure anhydride can be obtained by vacuum distillation.
Wird die Oxydation unter sonst gleichen Reaktionsbedingungen ohne Zusatz von Katalysatoren ausgeführt, so erhält man nur eine Ausbeute von .140.o Anhydrid im Reaktionsgemisch. Durch Vakuumdestillation werden 4oo'o Reinanhydrid erhalten.If the oxidation is not carried out under otherwise identical reaction conditions If the addition of catalysts is carried out, only a yield of .140.o is obtained Anhydride in the reaction mixture. 40,000 pure anhydride are obtained by vacuum distillation obtain.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA84420D DE708822C (en) | 1934-03-24 | 1934-03-24 | Process for the production of carboxylic acid anhydrides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA84420D DE708822C (en) | 1934-03-24 | 1934-03-24 | Process for the production of carboxylic acid anhydrides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE708822C true DE708822C (en) | 1941-07-29 |
Family
ID=6949177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA84420D Expired DE708822C (en) | 1934-03-24 | 1934-03-24 | Process for the production of carboxylic acid anhydrides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE708822C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2463114A1 (en) * | 1979-08-09 | 1981-02-20 | Celanese Corp | PROCESS FOR THE PRODUCTION OF SATURATED ALIPHATIC MONOCARBOXYLIC ACIDS |
-
1934
- 1934-03-24 DE DEA84420D patent/DE708822C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2463114A1 (en) * | 1979-08-09 | 1981-02-20 | Celanese Corp | PROCESS FOR THE PRODUCTION OF SATURATED ALIPHATIC MONOCARBOXYLIC ACIDS |
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