CH204697A - Process for the production of an organic mercury compound. - Google Patents
Process for the production of an organic mercury compound.Info
- Publication number
- CH204697A CH204697A CH204697DA CH204697A CH 204697 A CH204697 A CH 204697A CH 204697D A CH204697D A CH 204697DA CH 204697 A CH204697 A CH 204697A
- Authority
- CH
- Switzerland
- Prior art keywords
- mercury compound
- production
- mercury
- compound
- organic mercury
- Prior art date
Links
- 229940100892 mercury compound Drugs 0.000 title claims description 11
- 150000002731 mercury compounds Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- PQSXNIMHIHYFEE-UHFFFAOYSA-N 4-(1-phenylethyl)benzene-1,3-diol Chemical group C=1C=C(O)C=C(O)C=1C(C)C1=CC=CC=C1 PQSXNIMHIHYFEE-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229940106025 phenylethyl resorcinol Drugs 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- -1 monomercury compound Chemical class 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- MSYUMXXVCSLXMR-UHFFFAOYSA-N phenylmercury;hydrate Chemical compound O.[Hg]C1=CC=CC=C1 MSYUMXXVCSLXMR-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- DWVXFVWWARTDCQ-UHFFFAOYSA-N 2-ethylbenzene-1,3-diol Chemical compound CCC1=C(O)C=CC=C1O DWVXFVWWARTDCQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 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
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000001035 drying Methods 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
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005406 washing 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 Herstellung einer organischen quecksilbei#verbindung. Es ist bereits vorgeschlagen worden, Organakomplexqwecksilberverbindungen vom Typ R. Hg. OH. worin R einen aromatischen Rest, wie Phenyl, Tolyl usw., darstellt, mit Phenol und seinen Homologen umzusetzen.
Hierbei tritt die Hydroxylgruppe des Phenols mit d er Quecksilberverbindung unter Was@ser- abspaltun:g in Reaktion. Die .dabei entstehen- den: Quecksilberverbindungen sind praktiseh in Wasser unlöslich.
Lässt man Quecksilb-ervexbindungen vom Typ R.. Hg. OH auf mehrwertige Phenale, wie Resorcin oder Hydrochinon, ,einwirken, so erhält man ebenfalls Verbindungen, bei denen analog den obergenannten bekannten Verbindungen die vorhandenen Hydroxyl- gruppen mit der in Reaktion getreten sind,
wobei jede phenoli- sche Hydroxylgrupp.e mit einem Mol der Quecksilberverbindung umgesetzt wird.
Es wurde nun gefunden,. dass Phenyl:äthyl- resorcin von der Formel
EMI0001.0046
das also ein 1-Phenyläthyl-2;4--dioxy Benzol ist, bei dem ,die Phenyläthylgruppe sich in .der o,Stellung zu der einen OH-Gruppe und in p-Stellung zu der andern OH-Gruppe be findet, dieser Gesetzmässigkeit nicht folgt.
Das Phenyläthylresorcin tritt so in Reaktion mit der Quecksilberverbindung P.. Hg. OH; dasseine Hydroxylgruppe frei bleibt.
Es findet somit bei diesem zweiwertigen Phenol eine selektive Umsetzung der Hydro- xylgruppen mit .der Quecksilberverbindung statt, die nicht vorauszusehen war.
Die Erfindung besteht demgemäss in einem Verfahren zur Herstellung einer orga nischen Monoquecksilberverbindung mit dem Kennzeichen, .dass man Phenyläthylresorain der Formel
EMI0002.0004
mit Phenylquecksilberhydroxyd umsetzt, wo bei eins Hydroxylgruppe :des Phenyläthyl- resorcins an :der Reaktion nicht teilnimmt.
Die dabei entstandene neue Quecksilber verbindung zeichnet sich gegenüber den bekannten Reaktionsprodukten aus Phenol und dem Hydroxyd eines mercurierten aromatischen Kohlenwasserstoffes, nämlich R . Hg. OH, durch ihre Löslichkeit in ver- dünnten wässrigen Alkalien aus, deren pH- Wert über dem von Soda liegen muss.
Be dingt .durch clie vorhandene freie Hydroxyl- gruppe ist die neue Quecksilberverbindung in den wässrigeii Lösungen dieser Alkalien un- zersetzt löslich, da sie sich aus solchen Lö sungen mit Säuren, wie Kohlensäure, oder mit stark verdünnter Schwefelsäure unzer- setzt ausfällen lässt.
Die neue Quecksilberverbindung soll z. B. als Desinfekiions-, Konservierungs,- und Saat- gutbeizmittel zur Anwendung gelangen. <I>Beispiel:</I> 5 g Phenylquecksilberhydroxyd wurden in 2;00 cm' siedendem Wasser gelöst und hierzu 4 g Phenyläthylresorain der Formel
EMI0002.0047
gegeben.
Das Reahtionsgemenge wurde 20 Minuten auf dem Wasserbad erhitzt. Zuerst bildete sich auf dem Boden eine klebrige Schmiere, die aber allmählich fest wurde und sich schliesslich in ein braungelbes Pul ver verwandelte. Nach dem Auswaschen und Trocknen zeibte dieses Pulver den Schmelz punkt 145 . Ausbeute fast theoretisch.
Ge fundener Quecksilberwert 10,G0%. Theore- tiseher Quecksilberwert der P'henylä-th.yl- res.orein -1:Iono - Queck,silberphenylverbindun g 40,88 % .
Process for making an organic mercury compound. It has already been proposed to use organocomplex silver compounds of the R. Hg. OH. where R is an aromatic radical such as phenyl, tolyl, etc., to react with phenol and its homologues.
Here, 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 conjugate bonds of the R .. Hg. OH type are allowed to act on polyvalent phenals such as resorcinol or hydroquinone, compounds are also obtained in which the hydroxyl groups present have reacted with the above-mentioned known compounds,
each phenolic hydroxyl group being reacted with one mole of the mercury compound.
It has now been found. that phenyl: ethyl resorcinol of the formula
EMI0001.0046
which is a 1-phenylethyl-2; 4-dioxy benzene in which the phenylethyl group is in the o position to the one OH group and in the p position to the other OH group, according to this law does not follow.
The phenylethylresorcinol thus reacts with the mercury compound P .. Hg. OH; that one hydroxyl group remains free.
In the case of this dihydric phenol, a selective reaction of the hydroxyl groups with the mercury compound takes place, which could not have been foreseen.
The invention accordingly consists in a process for the preparation of an organic monomercury compound having the characteristic that one is phenylethylresorain of the formula
EMI0002.0004
with phenylmercuric hydroxide, where one of the hydroxyl groups of phenylethyl resorcinol does not participate in the reaction.
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, due to their solubility in dilute aqueous alkalis, the pH of which must be higher than that of soda.
Due to the free hydroxyl group present, the new mercury compound is insoluble without decomposition in the aqueous solutions of these alkalis, since it can be precipitated without decomposition from such solutions with acids, such as carbonic acid, or with very dilute sulfuric acid.
The new mercury compound should z. B. as disinfectants, preservatives, - and seed dressing are used. <I> Example: </I> 5 g of phenyl mercury hydroxide were dissolved in 2; 00 cm 'boiling water and 4 g of phenylethylresorain of the formula
EMI0002.0047
given.
The reaction mixture was heated on the water bath for 20 minutes. At first a sticky smear formed on the floor, but it gradually solidified and finally turned into a brownish-yellow powder. After washing out and drying, this powder had a melting point of 145. Almost theoretical yield.
Found mercury value 10, G0%. Theoretical mercury value of the phenyleth.ylres.orein -1: Iono - mercury, silver phenyl compound 40.88%.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE204697X | 1936-04-24 | ||
| CH200062T | 1938-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH204697A true CH204697A (en) | 1939-05-15 |
Family
ID=25723406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH204697D CH204697A (en) | 1936-04-24 | 1937-03-22 | Process for the production of an organic mercury compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH204697A (en) |
-
1937
- 1937-03-22 CH CH204697D patent/CH204697A/en unknown
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