DE904531C - Process for the preparation of dipyridyl violet salts - Google Patents
Process for the preparation of dipyridyl violet saltsInfo
- Publication number
- DE904531C DE904531C DED5112D DED0005112D DE904531C DE 904531 C DE904531 C DE 904531C DE D5112 D DED5112 D DE D5112D DE D0005112 D DED0005112 D DE D0005112D DE 904531 C DE904531 C DE 904531C
- Authority
- DE
- Germany
- Prior art keywords
- dipyridyl
- violet
- salts
- salt
- preparation
- 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
- 150000003839 salts Chemical class 0.000 title claims description 18
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000012670 alkaline solution Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
Verfahren zur Herstellung von Dipyridylviolettsalzen Die Erfindung betrifft ein Verfahren zur Herstellung von Dipyridylviolettsalzen. Es ist bereits bekannt, diese Substanzen durch Reduktion der quaternären Dipyridylsalze mit starken Reduktionsmitteln, wie Zink oder Chromosalz, in saurer Lösung herzustellen. Die Reduktion ist auch in alkalischer Lösung mittels Natriumhydrosulfit, Hydroxylamin, Zink und Eisen durchgeführt worden. Diese Verfahren sind jedoch für eine technische Herstellung nicht geeignet. da die genannten Substanzen auf diesem Wege nur unrein und mit geringen Ausbeuten erhalten werden. Dies trifft insbesondere für die Herstellung mit Hydrosulfit zu.Process for the preparation of dipyridyl violet salts The invention relates to a process for the preparation of dipyridyl violet salts. It is already known, these substances by reducing the quaternary dipyridyl salts with strong To produce reducing agents, such as zinc or chromosalt, in acidic solution. the Reduction is also possible in alkaline solution using sodium hydrosulfite, hydroxylamine, Zinc and iron have been carried out. However, these procedures are for a technical one Manufacture not suitable. since the substances mentioned are only impure in this way and are obtained with low yields. This is particularly true for manufacturing with hydrosulfite too.
Die Erfindung vermeidet die Nachteile der bekannten Herstellungsverfahren und ermöglicht die Herstellung von reinen Dipyridylviolettsalzen in guter Ausbeute. Das erfindungsgemäße Verfahren besteht darin, daß das dem erstrebten Enderzeugnis entsprechende Dipyridyliumsalz in alkalischer Lösung bis zur Dihydrostufe reduziert und das so erhaltene Zwischenerzeugnis anschließend durch Hinzufügen der äquivalenten Menge des entsprechenden Dipyridyliumsalzes zum Dipyridylviolettsalz umgesetzt wird. Das erfindungsgemäße Verfahren läßt sich insbesondere deshalb glatt durchführen, weil die Reduktion bis zur Dihydrostufe unter den genannten Bedingungen außerordentlich schnell und glatt verläuft, während eine Weiterreduktion über die Dihydrostufe hinaus im Vergleich dazu sehr lange Einwirkungszeiten erfordert. Die Reduktion wird vornehmlich in schwach alkalischer Lösung durchgeführt. Als Reduktionsmittel können Metalle, wie Zink, Magnesium, Aluminium u. dgl., sowie auch die stark reduzierenden Salze der niederen Oxydationsstufen von Schwermetallen verwendet werden. Die Reduktion kann auch vorteilhaft elektrolytisch durchgeführt werden. Die Reduktion kann weiterhin in wäßriger Lösung vorgenommen werden, jedoch ist für eine spätere Isolierung des Dipyridylviolettsalzes die Verwendung geeigneter organischer Lösungsmittel zweckmäßig. Es werden hierbei Lösungen eines genau bestimmten Gehaltes an Dipyridylviolettsalz erhalten, aus denen das Dipyridylviolettsalz in an sich bekannter Weise isoliert werden kann. Die Natur der an den Stiekstof der Dipy ridyliumsalze gebundenen Reste spielt bei dem erfindungsgemäßen Verfahren keine Rolle. Selbstverständlich beschränkt sich das Verfahren nicht auf die Anwendung der einfachen quaternären Dipyridyliumsalze, sondern ist auch für deren Substitutionsprodukte,wie z. B. für die entsprechenden Derivate des Dilutidyls und ähnlicher Verbindungen, anwendbar.The invention avoids the disadvantages of the known manufacturing processes and enables the production of pure dipyridyl violet salts in good yield. The inventive method consists in that the desired end product corresponding dipyridylium salt reduced in alkaline solution to the dihydro stage and then the intermediate product thus obtained by adding the equivalent Amount of the corresponding dipyridylium salt is converted to the dipyridyl violet salt. The method according to the invention can therefore be carried out smoothly in particular, because the reduction to the dihydro stage under the conditions mentioned is extraordinary runs quickly and smoothly, while a further reduction beyond the dihydric level requires very long exposure times in comparison. The reduction becomes predominant carried out in weakly alkaline solution. Metals, such as zinc, magnesium, aluminum and the like, as well as the strongly reducing salts of the lower levels of oxidation be used by heavy metals. The reduction can also advantageously be carried out electrolytically. The reduction can still be done in aqueous solution, but is for a later Isolation of the dipyridyl violet salt using suitable organic solvents expedient. This results in solutions with a precisely determined content of dipyridyl violet salt obtained, from which the dipyridyl violet salt isolated in a manner known per se can be. The nature of the residues bound to the starch of the dipyridylium salts does not play a role in the method according to the invention. Limited, of course the process does not apply to the simple quaternary dipyridylium salts, but is also for their substitution products, such as. B. for the appropriate Derivatives of dilutidyl and similar compounds, applicable.
Die nach dem erfindungsgemäßen Verfahren hergestellten Verbindungen eignen sich insbesondere zum Nachweis und zur quantitativen Bestimmung von Sauerstoff in Gasen und Lösungen.The compounds prepared by the process of the invention are particularly suitable for the detection and quantitative determination of oxygen in gases and solutions.
Das erfindungsgemäße Verfahren sei an Hand eines Beispiels näher erläutert.The method according to the invention will be explained in more detail using an example.
Beispiel 4,1 g Dimethyldipyridyliummethylsulfat werden in rooo ccm Wasser gelöst, mit 20 ccm konzentriertem Ammoniak versetzt und mit io g fein geraspeltem Zink geschüttelt, bis die anfänglich gebildete tiefviolette Farbe wieder verschwunden ist. Dann wird die Lösung von weiteren 4. ,1 g Dimethyldipyridyliummethylsulfat in 98o ccm Wasser zugegeben, einmal umgeschüttelt und abfiltriert. Die Lösung enthält fast genau 1/"o Mol Dipyridylviolettsalz pro Liter, was durch Titration mit einer Kupfersalzlösung von bekanntem Gehalt bestimmt werden kann. Selbstverständlich sind hierbei alle Operationen unter Sauerstofausschluß durchzuführen. Ebenso ist für die Lösungen sauerstofffreies Wasser zu verwenden.Example 4.1 g of dimethyldipyridylium methyl sulfate are dissolved in rooo ccm Dissolved water, mixed with 20 ccm of concentrated ammonia and added 10 g of finely grated Zinc shaken until the initially formed deep purple color disappeared again is. Then the solution of a further 4th, 1 g of dimethyldipyridylium methyl sulfate added in 98o ccm of water, shaken once and filtered off. The solution contains almost exactly 1 / "o mole of dipyridyl violet salt per liter, which can be determined by titration with a Copper salt solution of known content can be determined. Of course are carry out all operations with the exclusion of oxygen. Likewise is for the solutions to use oxygen-free water.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED5112D DE904531C (en) | 1944-12-02 | 1944-12-02 | Process for the preparation of dipyridyl violet salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED5112D DE904531C (en) | 1944-12-02 | 1944-12-02 | Process for the preparation of dipyridyl violet salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE904531C true DE904531C (en) | 1954-02-18 |
Family
ID=7031262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED5112D Expired DE904531C (en) | 1944-12-02 | 1944-12-02 | Process for the preparation of dipyridyl violet salts |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE904531C (en) |
-
1944
- 1944-12-02 DE DED5112D patent/DE904531C/en not_active Expired
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