CH204698A - Process for the production of an organic mercury compound. - Google Patents
Process for the production of an organic mercury compound.Info
- Publication number
- CH204698A CH204698A CH204698DA CH204698A CH 204698 A CH204698 A CH 204698A CH 204698D A CH204698D A CH 204698DA CH 204698 A CH204698 A CH 204698A
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- mercury compound
- mercury
- production
- organic mercury
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 229940100892 mercury compound Drugs 0.000 title description 14
- 150000002731 mercury compounds Chemical class 0.000 title description 14
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229940079877 pyrogallol Drugs 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- -1 R.Hg.OH Chemical class 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229940100890 silver compound Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- MSYUMXXVCSLXMR-UHFFFAOYSA-N phenylmercury;hydrate Chemical compound O.[Hg]C1=CC=CC=C1 MSYUMXXVCSLXMR-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- UKHWJBVVWVYFEY-UHFFFAOYSA-M silver;hydroxide Chemical compound [OH-].[Ag+] UKHWJBVVWVYFEY-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 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 Herstellung einer organischen Quecksilberverbindung. Es ist bereits vorgeschlagen worden, Organokomplexquecksilberverbindungen vom Typ R . Hg . OH, worin R einen aroma tischen Rest, wie Phenyl, Tolyl usw., dar stellt, mit Phenol und seinen Homologen um zusetzen. Hierbei tritt die Hydroxylgruppe des Phenols mit der Quecksilberverbindung unter Wasserabspaltung in Reaktion. Die da bei entstehenden Quecksilberverbindungen sind praktisch in Wasser unlöslich.
Lässt man Quecksilberverbindungen vom Typ R. Hg. OH auf mehrwertige Phenole, wie Resorcin oder Hydrochinon einwirken, so erhält man ebenfalls Verbindungen, bei denen analog den obengenannten bekannten Verbindungen die vorhandenen Hydroxyl- gruppen mit der Quecksilberverbindung in Reaktion getreten sind, wobei jede phenolische Rydroxylgruppe mit einem 1VIol der Queck silberverbindung umgesetzt wird.
Es wurde nun gefunden, dass dieser Ge setzmässigkeit P- #rogallol, ein dreiwertiges Phenol, bei dem sich die Hydroxylgruppen in 1. 2. 3-Stellung befinden, nicht folgt. Das Pyrogallol tritt so in Reaktion mit der Quecksilberverbindung R. Hg. OH, dass eine Hydroxylgruppe frei bleibt.
Es findet somit bei diesem dreiwertigen Phenol eine selektive Umsetzung der Hy- droxylgruppen mit der Quecksilberverbin- dung statt, die nicht vorauszusehen war.
Die Erfindung besteht demgemäss in einem Verfahren zur Herstellung einer orga nischen Diquecksilberverbindung mit dem Kennzeichen, dass man Pyrogallol, bei dem eine Hydroxylgruppe an der Reaktion nicht teilnimmt, mit Phenylquecksilberhydroxyd umsetzt.
Die dabei entstehende neue Quecksilber verbindung zeichnet sich gegenüber den be kannten Reaktionsprodukten aus Phenol und dem Hydroxyd eines mercurierten aroma tischen Kohlenwasserstoffes, nämlich R.Hg.OH, durch ihre Löslichkeit in verdünnten wä.ss- rigen Alkalien aus, deren pH-Wert über dem von Soda. liegen muss.
Bedingt durch die vor handene freie Hydroxylgruppe ist die neue Quecksilberverbindung in den wässrigen Lö sungen dieser Alkalien unzersetzt löslich, da sie sieh aus solchen Lösungen mit Säuren wie Kohlensäure oder mit stark verdünnter Schwefelsäure unzersetzt ausfällen lässt.
Die neue Quecksilberverbindung soll zum Beispiel als Desinfektions-, Konservierungs- und Saatgutbeizmittel zur Anwendung langen.
Beispiel: 29,4g Pheaylquecl@silberhydroxvd wur den in 800 cm' siedendem Wasser gelöst und hierzu 15 g Pv rogallol, gelöst in 100 ein' Wasser, hinzugegeben. Die Pyrogallolcliiecl@- silberverbindung schied sich als graubrauner Körper mit fast theoretischer Ausbeute ab. Die Quecksilberverbindung zeigte keinen ein- wandfreien Schmelzpunkt, da sie sich beim Brhitzen zersetzte.
Gefundener Quecksilber wert 59,8 0",'. Theoretischer Quecksilberwert der Pyrogallol-diquecl@silberdiphenylverbin- d-aiIg 59,1 ö .
Process for the production of an organic mercury compound. It has already been proposed to use organocomplex mercury compounds of the type R. Ed. OH, where R is an aromatic radical, such as phenyl, tolyl, etc., is to react with phenol and its homologues. The hydroxyl group of the phenol reacts with the mercury compound with elimination of water. The resulting mercury compounds are practically insoluble in water.
If mercury compounds of the R.Hg.OH type are allowed to act on polyvalent phenols such as resorcinol or hydroquinone, compounds are also obtained in which the hydroxyl groups present have reacted with the mercury compound analogously to the above-mentioned known compounds, with each phenolic hydroxyl group is reacted with a 1VIol of the mercury compound.
It has now been found that P- #rogallol, a trivalent phenol in which the hydroxyl groups are in the 1. 2. 3-position, does not follow this legality. The pyrogallol reacts with the mercury compound R. Hg. OH in such a way that a hydroxyl group remains free.
With this trihydric phenol there is a selective conversion of the hydroxyl groups with the mercury compound, which could not be foreseen.
The invention accordingly consists in a process for the preparation of an organic dimeric silver compound with the characteristic that pyrogallol, in which a hydroxyl group does not take part in the reaction, is reacted with phenylmercuric hydroxide.
The resulting new mercury compound is distinguished from the known reaction products of phenol and the hydroxide of a mercurized aromatic hydrocarbon, namely R.Hg.OH, by its solubility in dilute aqueous alkalis, whose pH value is above of soda. must lie.
Due to the existing free hydroxyl group, the new mercury compound is insoluble in the aqueous solutions of these alkalis, since it can precipitate without decomposition from such solutions with acids such as carbonic acid or with highly dilute sulfuric acid.
The new mercury compound should, for example, be used as a disinfectant, preservative and seed dressing agent.
Example: 29.4 g of Pheaylquecl® silver hydroxide were dissolved in 800 cm boiling water and 15 g of PVC rogallol, dissolved in 100% of water, were added. The pyrogallol silver compound deposited as a gray-brown body with an almost theoretical yield. The mercury compound did not show a perfect melting point because it decomposed when heated.
Found mercury value 59.8 0 ". Theoretical mercury value of the pyrogallol-diquecl @ silver-diphenyl compound d-aiIg 59.1 Ö.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE204698X | 1936-04-24 | ||
| CH200062T | 1938-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH204698A true CH204698A (en) | 1939-05-15 |
Family
ID=25723407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH204698D CH204698A (en) | 1936-04-24 | 1937-03-22 | Process for the production of an organic mercury compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH204698A (en) |
-
1937
- 1937-03-22 CH CH204698D patent/CH204698A/en unknown
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