CH209331A - Process for the mercuration of benzene. - Google Patents
Process for the mercuration of benzene.Info
- Publication number
- CH209331A CH209331A CH209331DA CH209331A CH 209331 A CH209331 A CH 209331A CH 209331D A CH209331D A CH 209331DA CH 209331 A CH209331 A CH 209331A
- Authority
- CH
- Switzerland
- Prior art keywords
- acetic acid
- benzene
- amount
- glacial acetic
- anhydride
- Prior art date
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims description 48
- 238000000034 method Methods 0.000 title claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 34
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 30
- 229960000583 acetic acid Drugs 0.000 claims description 17
- 239000012362 glacial acetic acid Substances 0.000 claims description 17
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- XEBWQGVWTUSTLN-UHFFFAOYSA-M phenylmercury acetate Chemical compound CC(=O)O[Hg]C1=CC=CC=C1 XEBWQGVWTUSTLN-UHFFFAOYSA-M 0.000 description 2
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
- 229940076134 benzene Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000010438 heat treatment Methods 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
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
- C07F3/12—Aromatic substances containing mercury
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur blerenrierung von Benzol. Die Mercurierung von Benzol mit Mer- curiacetat in Gegenwart von Eisessig unter Druck und Erhitzung ist bekannt. Um das Arbeiten unter Druck zu vermeiden, ist be reits vorgeschlagen worden, die Mercurierung unter Anwendung von grösseren Mengen Eis essig, die ein Mehrfaches der angewendeten Benzolmenge betragen, vorzunehmen.
Es ist nun gefunden worden, dass man ohne Anwendung von Druck mit verhältnis mässig geringen Mengen Eisessig, d. b. Eis essigmengen, die nur einen Bruchteil der angewendeten Menge des Benzols darstellen, in kurzer Zeit eine vollkommene Mercurierung des Benzols erreichen kann, wenn man einen Teil des Eisessigs durch Essigsäureanhydrid ersetzt.
Gemäss der Erfindung wird daher Mer- curiacetat auf Benzol in Gegenwart von Eis essig und Essigsäureanhydrid, vorzugsweise bei gewöhnlichem Druck, einwirken gelassen. Die Umsetzung kann dabei in Gegenwart verhältnismässig geringer Mengen von Eis essig stattfinden. Zweckmässig beträgt die zur Anwendung gelangende Menge von Eisessig und Essigsäureanhydrid einen Bruch teil der Menge des Benzols. Es hat sich hierbei als vorteilhaft erwiesen, die Mengen verhältnisse so zu wählen, dass die ange wendete Menge von Eisessig und Essigsäure anhydrid zusammen etwa der Hälfte der Benzolmenge entspricht.
Die Essigsäureanhy- dridmenge beträgt dabei vorteilhaft wiederum etwa die Hälfte oder etwas mehr der ange wendeten Eisessigmenge.
Das Verfahren gemäss der Erfindung zeichnet sich, wie Versuche ergaben, durch eine kurze Reaktionsdauer für die Mercu- rierung und geringe Destillationszeit aus und gestattet eine besonders gute Ausnutzung der Apparatur, da nur vergleichsweise ge ringe Mengen von Eisessig angewendet zu werden brauchen. Ferner wird, wie sich zeigte, eine sehr gute Ausbeute erhalten, da Verluste durch Zersetzung des gebildeten Mercurierungsproduktes vollkommen zu ver- nachlässigen sind.
Das Verfahren gemäss der Erfindung wird nachstehend an Hand eines Beispiels näher erläutert.
<I>Beispiel:</I> Es wurden 11,8 Teile Alercuriacetat in einem Gemisch von 62 Teilen Benzol, 18 Teilen Eisessig und 11 Teilen Essigsäure anhydrid aufgenommen und unter Rückfluss zum Kochen erhitzt. Die Kochtemperatur betrug dabei etwa<B>850.</B> Nach Verlauf von etwa 4 bis 4'/2 Stunden war die Mereurie- rung des Benzols beendet. Nach dem Ab destillieren von Benzol, Eisessig und Essig säureanhydrid wurde eine weissliche, feste kristalline Masse erhalten, die kein ionisier tes Quecksilber enthielt und aus Phenyl- quecksilberacetat bestand.
An Stelle von Quecksilberacetat kann auch die äquivalente Menge Quecksilberoxyd zur Anwendung ge langen.
Das nach dem Verfahren gemäss der Er findung hergestellte Phenylquecksilber-acetat ist insbesondere zur Weiterverarbeitung auf Mittel geeignet, die zur Desinfektion, Kon servierung und zum Beizen von Saatgut Ver wendung finden.
Process for the fermentation of benzene. The mercuration of benzene with mercuriacetate in the presence of glacial acetic acid under pressure and with heating is known. In order to avoid working under pressure, it has already been proposed to carry out the mercuration using large amounts of glacial acetic acid which are several times the amount of benzene used.
It has now been found that without the application of pressure with relatively small amounts of glacial acetic acid, i. b. Amounts of glacial acetic acid, which represent only a fraction of the amount of benzene used, can achieve complete mercuration of the benzene in a short time if one replaces part of the glacial acetic acid with acetic anhydride.
According to the invention, mercuriacetate is therefore allowed to act on benzene in the presence of glacial acetic acid and acetic anhydride, preferably under normal pressure. The reaction can take place in the presence of relatively small amounts of glacial acetic acid. The amount of glacial acetic acid and acetic anhydride used is advantageously a fraction of the amount of benzene. It has proven to be advantageous here to choose the proportions in such a way that the amount of glacial acetic acid and acetic anhydride used together corresponds to about half the amount of benzene.
The amount of acetic anhydride is in turn advantageously about half or slightly more of the amount of glacial acetic acid used.
As experiments have shown, the process according to the invention is distinguished by a short reaction time for the mercuring and a short distillation time and allows particularly good utilization of the apparatus, since only comparatively small amounts of glacial acetic acid need to be used. Furthermore, as has been shown, a very good yield is obtained since losses due to decomposition of the mercuration product formed can be completely neglected.
The method according to the invention is explained in more detail below using an example.
<I> Example: </I> 11.8 parts of alercuriacetate were taken up in a mixture of 62 parts of benzene, 18 parts of glacial acetic acid and 11 parts of acetic acid anhydride and heated to the boil under reflux. The boiling temperature was about 850. After about 4 to 4 1/2 hours, the mergerization of the benzene was complete. After benzene, glacial acetic acid and acetic acid anhydride had been distilled off, a whitish, solid crystalline mass was obtained which did not contain any ionized mercury and consisted of phenyl mercury acetate.
Instead of mercury acetate, the equivalent amount of mercury oxide can also be used.
The phenyl mercury acetate produced by the method according to the invention is particularly suitable for further processing on agents that are used for disinfection, preservation and dressing of seeds.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE209331X | 1937-07-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH209331A true CH209331A (en) | 1940-04-15 |
Family
ID=5794708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH209331D CH209331A (en) | 1937-07-05 | 1938-07-05 | Process for the mercuration of benzene. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH209331A (en) |
-
1938
- 1938-07-05 CH CH209331D patent/CH209331A/en unknown
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