CH294179A - Process for the preparation of pyridyl mercury chloride. - Google Patents
Process for the preparation of pyridyl mercury chloride.Info
- Publication number
- CH294179A CH294179A CH294179DA CH294179A CH 294179 A CH294179 A CH 294179A CH 294179D A CH294179D A CH 294179DA CH 294179 A CH294179 A CH 294179A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- pyridine
- pyridyl
- solution
- mercury
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- -1 pyridyl mercury chloride Chemical compound 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 150000002730 mercury Chemical class 0.000 claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000000645 desinfectant Substances 0.000 claims description 2
- 230000002070 germicidal effect Effects 0.000 claims description 2
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000000853 adhesive Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- GKZFRRZFPOQSHI-UHFFFAOYSA-N N1=CC=CC=C1.[Hg] Chemical compound N1=CC=CC=C1.[Hg] GKZFRRZFPOQSHI-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- IRJYVGQWVKGHJL-UHFFFAOYSA-M chloro(pyridin-2-yl)mercury Chemical compound Cl[Hg]C1=CC=CC=N1 IRJYVGQWVKGHJL-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 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
- C07F3/14—Heterocyclic substances containing mercury
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung von Pyridylquecksilberehlorid. Man hat vorgeschlagen, Py ridin bei er höhter Temperatur von 155 bzw.<B>1800</B> im Druckgefäss zu merkurieren, indem man Pyri- din in Anwesenheit von Wasser Quecksilber acetat zusetzt und das Gemisch mehrere Stun den iin Autoklaven erhitzt.
Man erhält mono- inerkurierte Substitutionsprodukte, wie Pyri- dylqueeksilberaeetat,Pyridylquecksilberehlorid n. a. (11e. Clelland und Wilson 1. Chem. Soe., London 1032, 1263, und 1I. MV. Swaney, 1I. J.
S'keeters und R.llorris Shreve, Industr. and Engineering Chemistry 1940, Vol. 3'2, Nr.3, S. 360). Dabei waren nicht nur die Ausbeu ten unbefriedigend, sondern es bereitete auch Kehwierigkeiten, dieses Verfahren in den Grossbetrieb zu überführen.
Es müssen Druek- gefiisse verwendet werden, die gegen anorga nische Quecksilbersalze, Pyridin und den sieh bildenden Eisessig beständig sein müssen.
Es wurde nun gefunden, dass man diese Nachteile vermeiden und PyridylqLieeksilbei-- chlorid in guter Ausbeute einfach und wirt schaftlich herstellen kann, wenn man erfin dungsgemäss eine Lösung eines in Pyridin lös baren Quecksilbersalzes einer niederen Fett säure in mehr als 10 llol Pyridin bei ge- wölinliehem Druel;
länger als 12 Stunden am Rückfloss zitin Sieden erhitzt., darauf das über schüssige Pyridin abdestilliert, den Rückstand in Wasser löst, die Lösung mit. Alkalilauge versetzt, vom Niederschlag trennt und aus dem Filtrat durch Zusatz einer Fettsäure die Pyridin-Quecksilber-Fettsäure-Verbindung gewinnt und diese mit wässeriger Natrium chloridlösung in das Pyridylquecksilberchlorid überführt.
<I>Beispiel:</I> 20,0 g Quecksilber(II)acetat werden in 100 em33 Py ridin gelöst (iVIolv erhältnis etwa 1 : 20) und 72 Stunden am Rückfliisskühler zum Sieden erhitzt. Nach dem Erkalten wird die Lösung filtriert. und das Pyridin im Vakuum abdestilliert. Dieses kann wieder für einen N euansatz verwendet erden.
Der Rück stand wird in Wasser gelöst und mit. 30 prozentiger Natronlauge versetzt, bis kein Niederschlag mehr entsteht. Es wird abfil- triert. In dem Filtrat befindet sieh Pyridyl- quecksilberhydroxyd, das durch Zusatz von Eisessig in das Pyridylquecksilberacetat über geführt wird. Um das Pyridylquecksilber- aeetat in das Chlorid umzuwandeln, wird diese Lösung mit 10prozentiger Kochsalzlösung ausgefällt. Der entstehende rein weisse Nie derschlag wird abgesaugt, mit. \Nasser gewa schen und getrocknet.
Rohausbeute: 9,45 g (etwa -18 /o der theo retischen). Das Py rid@Tlquecksilberelilorid lässt sieb aus 30- bis 50prozentigen Pyridin- Wasser-Geinischen unter Zusatz von Kohle umkristallisieren. Es bildet Nadeln vom Zer setzungspunkt 2600.
Der Stickstoffgehalt be- trägt -1,68 la gegenüber dem berechneten von -1,54 0/a. Es enthält 63,9 % Hg gegen- über dem berechneten Gehalt von 6-1,7 010.
Die Verbindung ist in Lauge und Pvridin leicht, in Salzsäure etwas schwerer löslich. Mit Schwefelwasserstoff entsteht kein Queck silbersulfid. Durch Bromierung erhält man 3-Brom-Pv ridin vom Siedepunkt 173 . Das Pvridvlqtteeksilberclilorid ist ein wirksames bakterizides und keimtötendes Mittel, das mit Vorteil als Desinfektionsmittel verwendet werden kann.
Process for the preparation of pyridyl mercury chloride. It has been proposed to mercury pyridine at an elevated temperature of 155 or 1800 in the pressure vessel by adding mercury acetate to pyridine in the presence of water and heating the mixture in an autoclave for several hours.
One receives monohydric substitution products, such as pyridylqueekilberaetate, pyridylmercuric chloride n.a. (11e. Clelland and Wilson 1. Chem. Soe., London 1032, 1263, and 1I. MV. Swaney, 1I. J.
S'keeters and R.llorris Shreve, Industr. and Engineering Chemistry 1940, Vol. 3'2, No. 3, p. 360). Not only were the yields unsatisfactory, but it was also difficult to transfer this process to large-scale operations.
Pressure vessels must be used that are resistant to inorganic mercury salts, pyridine and the glacial acetic acid that forms.
It has now been found that these disadvantages can be avoided and pyridyl silicone chloride can be produced easily and economically in good yield if, according to the invention, a solution of a pyridine-soluble mercury salt of a lower fatty acid in more than 10 llol pyridine at wölinliehem druel;
Heated at the reflux for more than 12 hours, then the excess pyridine is distilled off, the residue is dissolved in water, the solution with. Alkali hydroxide solution is added, the precipitate is separated off and the pyridine-mercury-fatty acid compound is obtained from the filtrate by adding a fatty acid and this is converted into the pyridyl mercury chloride with aqueous sodium chloride solution.
<I> Example: </I> 20.0 g of mercury (II) acetate are dissolved in 100 cubic meters of pyridine (ratio approx. 1:20) and heated to the boil for 72 hours on a reflux condenser. After cooling, the solution is filtered. and the pyridine is distilled off in vacuo. This can be used again for a new approach.
The residue is dissolved in water and with. 30 percent sodium hydroxide solution is added until no more precipitate forms. It is filtered off. The filtrate contains pyridyl mercury hydroxide, which is converted into pyridyl mercury acetate by adding glacial acetic acid. In order to convert the pyridyl mercury acetate into the chloride, this solution is precipitated with 10 percent saline solution. The resulting pure white precipitate is sucked off with. \ Nwater washed and dried.
Crude yield: 9.45 g (about -18 / o of the theoretical). The pyridine @ mercury eliloride can be recrystallized from 30 to 50 percent pyridine-water mixtures with the addition of charcoal. It forms needles from decomposition point 2600.
The nitrogen content is -1.68 la compared to the calculated value of -1.54 0 / a. It contains 63.9% Hg compared to the calculated level of 6-1.7 010.
The compound is easily soluble in lye and pvridine, and somewhat less soluble in hydrochloric acid. No mercury sulfide is formed with hydrogen sulfide. Bromination gives 3-bromine-PVC with a boiling point of 173. Pvridvlqtteksilberclilorid is an effective bactericidal and germicidal agent, which can be used with advantage as a disinfectant.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE294179X | 1944-04-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH294179A true CH294179A (en) | 1953-10-31 |
Family
ID=6083574
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH294179D CH294179A (en) | 1944-04-27 | 1945-03-13 | Process for the preparation of pyridyl mercury chloride. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH294179A (en) |
-
1945
- 1945-03-13 CH CH294179D patent/CH294179A/en unknown
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