DE16750C - Process for the preparation of dyes of the rosaniline grater from Niiroleukobasen of triphenylmethane - Google Patents
Process for the preparation of dyes of the rosaniline grater from Niiroleukobasen of triphenylmethaneInfo
- Publication number
- DE16750C DE16750C DENDAT16750D DE16750DA DE16750C DE 16750 C DE16750 C DE 16750C DE NDAT16750 D DENDAT16750 D DE NDAT16750D DE 16750D A DE16750D A DE 16750DA DE 16750 C DE16750 C DE 16750C
- Authority
- DE
- Germany
- Prior art keywords
- rosaniline
- triphenylmethane
- dyes
- niiroleukobasen
- grater
- 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
- NIKFYOSELWJIOF-UHFFFAOYSA-O Fuchsine Chemical compound Cl.C1=C(N)C(C)=CC(C(=C2C=CC(=[NH2+])C=C2)C=2C=CC(N)=CC=2)=C1 NIKFYOSELWJIOF-UHFFFAOYSA-O 0.000 title claims 2
- AAAQKTZKLRYKHR-UHFFFAOYSA-N Triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 title description 2
- 239000000975 dye Substances 0.000 title description 2
- 238000000034 method Methods 0.000 title description 2
- 230000001603 reducing Effects 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 1
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 2
- 150000004992 toluidines Chemical class 0.000 description 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L Iron(II) chloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J Tin(IV) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- -1 iron chlorine Chemical compound 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
- C09B11/20—Preparation from other triarylmethane derivatives, e.g. by substitution, by replacement of substituents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
Dr. OTTO FISCHER in MÜNCHEN.Dr. OTTO FISCHER in MUNICH.
Patentirt im Deutschen Reiche vom 8. Februar 1881 ab.Patented in the German Empire on February 8, 1881.
Durch Einwirkung von Paranitrobittermandelöl auf Anilinsalze bei Gegenwart von Chlorzink erhält man ein Paranitrodiamidotriphenylmethan nach der Gleichung:By the action of paranitro bitter almond oil on aniline salts in the presence of zinc chloride one obtains a paranitrodiamidotriphenylmethane according to the equation:
NO2 -C6H4,. CO H+ 2 C6 H5 - NH2 = NO 2 -C 6 H 4,. CO H + 2 C 6 H 5 - NH 2 =
N0*'C*H*'CH\cV£.NH2 N0 * ' C * H *' CH \ cV £ .NH 2
Diese Nitrobase liefert bei der Reduction Paraleukanilin, welches durch Oxydation in Rosanilin übergeführt werden kann.This nitro base supplies paraleukaniline during the reduction, which by oxidation in Rosaniline can be transferred.
Meine Erfindung ist nun folgende:My invention is now as follows:
Anstatt die oben genannte Nitroleukobase in getrennten Operationen erst zu reduciren und nachher zu oxydiren, führe ich dieselbe durch einen Procefs direct in Rosanilin über.Instead of first reducing and reducing the above-mentioned nitro leuco base in separate operations to oxidize afterwards, I convert it directly into rosaniline by a process.
Zu dem Zweck behandle ich die Nitrobase mit Metallsalzen, welche auf die Nitrogruppe reducirend wirken und gleichzeitig Sauerstoff auf die Methangruppe übertragen.For this purpose I treat the Nitrobase with metal salts, which act on the Nitro group have a reducing effect and at the same time transfer oxygen to the methane group.
Ich erhitze z. B. einen Theil Paranitrodiamidotriphenylmethan mit zwei Theilen festen Eisenchlorürs unter Umrühren auf 160 bis i8o° so lange, bis eine homogene, bronzeglänzende Schmelze entstanden ist.I heat z. B. a part of paranitrodiamidotriphenylmethane with two parts of solid iron chloride, with stirring, to 160 to 180 ° long until a homogeneous, bronze-shining melt has formed.
Die Schmelze wird mit verdünnter Salzsäure ausgekocht, und das gelöste Fuchsin wird nach bekannten Methoden abgeschieden und gereinigt. The melt is boiled with dilute hydrochloric acid, and the dissolved fuchsin is after known methods deposited and cleaned.
Die Bildung des Rosanilins erfolgt nach der Gleichung:.The formation of the rosaniline takes place according to the equation:
C6 H1 - IVH1 C 6 H 1 - IVH 1
NO2 . C6 H, . CH NO 2 . C 6 H,. CH
C6 H1 · NH2 C 6 H 1 • NH 2
C19 H11 N3 + 2 O. C 19 H 11 N 3 + 2 O.
An Stelle des Eisenchlorürs kann man auch andere reducirenden Metallzalze, z. B. Zinnchlorür, anwenden.Instead of iron chlorine, other reducing metal salts can also be used, e.g. B. tin chloride, use.
Die gleiche Reaction läfst sich bei den Homologen des Nitrodiamidotriphenylmethans, welche man durch Condensation von Paranitrobittermandelöl mit Toluidin oder mit einem Gemenge von Anilin und Toluidin erhält, ausführen. The same reaction can be found with the homologues of nitrodiamidotriphenylmethane, which can be obtained by condensation of paranitro bitter almond oil with toluidine or with a Mixture of aniline and toluidine received, run.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE16750C true DE16750C (en) |
Family
ID=293725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT16750D Active DE16750C (en) | Process for the preparation of dyes of the rosaniline grater from Niiroleukobasen of triphenylmethane |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE16750C (en) |
-
0
- DE DENDAT16750D patent/DE16750C/en active Active
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