DE230597C - - Google Patents
Info
- Publication number
- DE230597C DE230597C DENDAT230597D DE230597DA DE230597C DE 230597 C DE230597 C DE 230597C DE NDAT230597 D DENDAT230597 D DE NDAT230597D DE 230597D A DE230597D A DE 230597DA DE 230597 C DE230597 C DE 230597C
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- pyridine
- parts
- reaction
- red
- 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.)
- Active
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000981 basic dye Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000000975 dye Substances 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000001476 alcoholic Effects 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000004576 sand Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-Aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- 229940080423 Cochineal Drugs 0.000 description 1
- 241000854350 Enicospilus group Species 0.000 description 1
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000012730 carminic acid Nutrition 0.000 description 1
- 239000004106 carminic acid Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- -1 chlorozinc pyridine compound Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004753 textile Substances 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
- C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
/■/ ■
fJ .'St1)KVi Λ fJ .'St 1 ) KVi Λ
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- Ja 230597 KLASSE 22 e. GRUPPE- Yes 230597 CLASS 22 e. GROUP
in WÜRZBURG.in WÜRZBURG.
Läßt man auf Pyridin Chlor in Gegenwart indifferenter organischer Verdünnungsmittel bzw. Lösungsmittel, wie z. B. Äther, Tetrachlorkohlenstoff einwirken, so nimmt das Pyridin Chlor auf.If chlorine is left on pyridine in the presence of inert organic diluents or solvents, such as. B. ether, carbon tetrachloride act, the pyridine takes Chlorine on.
Läßt man auf das Reaktionsprodukt Amine einwirken, so geht eine stürmische Reaktion vor sich, die von freiwerdendem Chlor herrührt. Dabei findet nur in untergeordnetemIf amines are allowed to act on the reaction product, a stormy reaction ensues in front of you, which comes from the released chlorine. It only takes place in subordinate
ίο Maße Farbstoffbildung statt.ίο Dimensions of dye formation instead.
Behandelt man unverdünntes Pyridin mit Chlor, so wird dies ebenfalls aufgenommen; das Reaktionsprodukt enthält verschiedene Chlorierungsprodukte des Pyridins, unter welchen sich auch in geringer Menge eine labile Verbindung befindet, die mit Aminen unter Farbstoffbildung reagiert. Zerlegt man aber das Reaktionsprodukt durch Destillation in verschiedene Fraktionen, um den Farbstoffbildner zu isolieren, so findet hierbei anscheinend Zersetzung statt; denn weder der Rückstand noch die einzelnen Fraktionen geben mit Aminen Farbstoff. Eine Anreicherung des Bestandteiles in der Reaktionsmasse, weleher zur Farbstoffbildung befähigt ist, gelingt durch übliche Abänderungen in der Art der Chlorierung nicht.If undiluted pyridine is treated with chlorine, this is also taken up; the reaction product contains various chlorination products of pyridine, among which there is also a small amount of a labile compound that is associated with amines Dye formation reacts. But if you decompose the reaction product by distillation into apparently find different fractions to isolate the dye former Decomposition takes place; because neither the residue nor the individual fractions give with amines dye. An enrichment of the constituent in the reaction mass, whichever is capable of dye formation is achieved by customary changes in the type of Not chlorination.
Behandelt man nun Pyridin mit Chlor unter Zusatz gewisser die Reaktion fördernder Mittel, so wird eine Reaktionsmasse erhalten, welche zur Farbstoffdarstellung gut geeignet ist und bei der Einwirkung von Aminen reichliche Ausbeuten an wertvollen Farbstoffen liefert. Wie festgestellt worden ist, sind solche die Reaktion fördernde Mittel z. B. Chlorüberträger, wie Chlorzink oder Chlorcalcium. Noch besser eignen sich aber andere ganz neutrale Mittel, z. B. Kieselgur, oder noch vorteilhafter Seesand. Pyridin, welches mit einem der genannten Mittel versetzt ist, nimmt Chlor in großen Mengen auf. Das erhaltene Reaktionsprodukt kann unmittelbar zur Darstellung der Farbstoffe benutzt werden. Die bezeichneten Mittel haben auch einen günstigen Einfluß bei Chlorierung von Pyridin in organischen indifferenten Lösungs- oder Verdünnungsmitteln. If you now treat pyridine with chlorine with the addition of certain agents that promote the reaction, in this way a reaction mass is obtained which is well suited for the preparation of dyes and gives ample yields of valuable dyes when exposed to amines. As has been found, such reaction promoting agents are e.g. B. chlorine carrier, such as zinc chloride or calcium chloride. But other completely neutral ones are even better Means, e.g. B. kieselguhr, or even better sea sand. Pyridine, which with a of the agents mentioned is added, chlorine takes up in large quantities. The received Reaction product can be used directly to represent the dyes. the designated agents also have a beneficial effect in the chlorination of pyridine in organic inert solvents or diluents.
50 Teile Pyridin werden mit 5 Teilen wasserfreiem Chlorzink versetzt; unter Wärmeentwicklung entsteht zum Teil eine Chlorzinkpyridinverbindung (WiIh. Lang, Ber. XXI, 1586). Nach dem Abkühlen leitet man aus einem weiten Einleitungsrohr unter stetem Umrühren einen kräftigen Chlorstrom in das möglichst kalt gehaltene Pyridin ein. Entweichendes Chlor kann mit Jodkaliumstärkepapier nicht nachgewiesen werden. Nach einiger Zeit trübt sich die klare, gelblich gefärbte Flüssigkeit unter Abscheidung weißer Kristalle. In diesem Punkt sind 10 Teile Chlor aufgenommen worden. Die Absorption läßt sich bis zu 15 Teilen Chlor treiben, doch tritt dann stärkere Verharzung ein.50 parts of pyridine are mixed with 5 parts of anhydrous zinc chloride; with heat development Partly a chlorozinc pyridine compound is formed (WiIh. Lang, Ber. XXI, 1586). After cooling, one passes from a wide inlet pipe under steady Stir a vigorous stream of chlorine into the pyridine, which is kept as cold as possible. Escaping Chlorine cannot be detected with potassium iodine starch paper. After a while, the clear, yellowish color becomes cloudy Liquid with separation of white crystals. At this point there is 10 parts chlorine been recorded. The absorption can drive up to 15 parts of chlorine, but occurs then stronger resinification.
50 Teile Pyridin werden mit 5 Teilen ausgeglühtem Seesand versetzt. Die vorher wasserhelle Flüssigkeit nimmt beim Einleiten von50 parts of pyridine are mixed with 5 parts of calcined sea sand. The previously water-clear Liquid decreases when discharging
Chlor allmählich eine gelbliche Farbe an, die beim Fortschreiten der Reaktion tiefer wird. Bei Aufnahme von io Teilen Chlor findet eine kurz andauernde Reaktion statt; das Ganze nimmt dunkle Farbe an und wird zum Teil fest.Chlorine gradually turns a yellowish color that deepens as the reaction progresses. If 10 parts of chlorine are absorbed, a brief reaction takes place; the whole takes on dark color and partially solidifies.
10 Teile Pyridin werden mit 40 Teilen Tetrachlorkohlenstoff verdünnt und mit 1 Teil Seesand versetzt, worauf in die Masse Chlor eingeleitet wird. Es gelingt auf diese Weise mit Leichtigkeit, der Reaktionsmasse 9 Teile Chlor einzuverleiben. Dabei bildet sich eine schneeweiße Masse, die durch weiteres Verdünnen mit Tetrachlorkohlenstoff den Gefäßen leicht entnommen werden kann.10 parts of pyridine are mixed with 40 parts of carbon tetrachloride diluted and mixed with 1 part sea sand, whereupon chlorine is introduced into the mass will. It succeeds in this way with ease, the reaction mass 9 parts of chlorine to incorporate. A snow-white mass forms, which by further dilution with carbon tetrachloride can be easily removed from the vessels.
Das nach Beispiel 1 gewonnene chlorierte Pyridin wird filtriert und das Filtrat mit einer alkoholischen Lösung von 10 Teilen p-Toluidin (eine der aufgenommenen Chlormenge gleiche Quantität des Amins) versetzt. Schon in der Kälte tritt eine intensive Rotfärbung ein, die sich nach 1/i stündigem Erwärmen auf dem Wasserbade nicht mehr vertieft. Die alkoholische Lösung wird durch Einfließenlassen in verdünnte Salzsäure gefällt. Es resultiert in guter Ausbeute ein roter Farbstoff.The chlorinated pyridine obtained according to Example 1 is filtered and the filtrate is mixed with an alcoholic solution of 10 parts of p-toluidine (a quantity of amine equal to the amount of chlorine taken up). Even in the cold there is an intense red color, which does not deepen after 1 / i hour of warming on the water bath. The alcoholic solution is precipitated by pouring it into dilute hydrochloric acid. A red dye results in good yield.
Ein nach Beispiel 2 chloriertes Pyridin wird mit einer alkoholischen Lösung von 10 Teilen Dihydro- α-methylindol versetzt. Sofort tritt j intensive Rotfärbung ein, die sich bei kurzem Erwärmen auf dem Wasserbade nicht mehr | verstärkt. Die alkoholische, von Seesand durch Filtration befreite Lösung wird in verdünnte Salzsäure eingegossen und der auffallende cochenillerote Niederschlag filtriert und getrocknet.A pyridine chlorinated according to Example 2 is mixed with an alcoholic solution of 10 parts Dihydro-α-methylindole added. Immediately j intense red color, which no longer changes when heated briefly on the water bath reinforced. The alcoholic solution freed from sea sand by filtration is diluted in Poured hydrochloric acid and filtered the conspicuous cochineal red precipitate and dried.
Die nach Beispiel 3 erhaltene Reaktionsmasse, die einen weißen Kristallbrei vorstellt, wird von der überstehenden Flüssigkeit abgegossen und einige Zeit bei gewöhnlicher Temperatur stehen gelassen. Auf Zusatz von 9 Teilen einer alkoholischen p-Aminophenollösung tritt schon in der Kälte intensiv rote Färbung ein. Nach kurzem Erwärmen auf dem Wasserbade ist die Reaktion beendet; man filtriert vom Seesand ab und gießt in kalte 10 prozentige Salzsäure, wodurch die neue Verbindung als rotbrauner Niederschlag ausfällt.The reaction mass obtained according to Example 3, which presents a white crystal slurry, is poured off from the supernatant and for some time with ordinary Temperature left to stand. On the addition of 9 parts of an alcoholic p-aminophenol solution intensely red color occurs even in the cold. After a short warming on the water bath, the reaction is over; the sea sand is filtered off and poured into cold 10 percent hydrochloric acid, whereby the new compound precipitates as a red-brown precipitate.
Die nach dem beanspruchten Verfahren erhältlichen Farbstoffe gehören in die Gruppe der in der Patentschrift 155782 und in der französischen Patentschrift 395793 beschriebenen; sie färben Textilfasern in roten Nuancen an.The dyes obtainable by the claimed process belong to the group that described in patent 155782 and in French patent 395793; they dye textile fibers in red shades.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE230597C true DE230597C (en) |
Family
ID=490800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT230597D Active DE230597C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE230597C (en) |
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0
- DE DENDAT230597D patent/DE230597C/de active Active
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