DE105198C - - Google Patents
Info
- Publication number
- DE105198C DE105198C DENDAT105198D DE105198DA DE105198C DE 105198 C DE105198 C DE 105198C DE NDAT105198 D DENDAT105198 D DE NDAT105198D DE 105198D A DE105198D A DE 105198DA DE 105198 C DE105198 C DE 105198C
- Authority
- DE
- Germany
- Prior art keywords
- dimethylaniline
- leuco
- sesquichlorohydrate
- leuco base
- base
- 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
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000004961 triphenylmethanes Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LXZGVFCKZRHKMU-UHFFFAOYSA-N N-benzyl-N-methylaniline Chemical compound C=1C=CC=CC=1N(C)CC1=CC=CC=C1 LXZGVFCKZRHKMU-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229960000583 Acetic Acid Drugs 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 210000003298 Dental Enamel Anatomy 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- JPIYZTWMUGTEHX-UHFFFAOYSA-N auramine O free base Chemical compound C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 JPIYZTWMUGTEHX-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 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
- 230000000875 corresponding Effects 0.000 description 1
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 1
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000009114 investigational therapy Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000008379 phenol ethers Chemical class 0.000 description 1
- -1 phenolic ethers Chemical class 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In dem Patent Nr. 103858 wurde ein Verfahren zur Herstellung von Benzhydrylamin, dessen Homologen und Analogen beschrieben. Diese Basen werden durch Einwirkung von Blausä'uresesquichlorhydrat (Ber. der deutschen chemischen Gesellschaft, Bd. 16, S. 308) bei Gegenwart von Aluminiumchlorid auf aromatische Kohlenwasserstoffe und Phenolä'ther dargestellt. Im Verlauf der Untersuchung über das Blausä'uresesquichlorhydrat wurde dieser Körper auch auf tertiäre Amine einwirken gelassen und wurden dabei neue überraschende Ergebnisse erhalten.In the patent No. 103858 a process for the preparation of benzhydrylamine, its homologues and analogs are described. These bases are made by the action of Prussic acid sesquichlorohydrate (report of the German chemical society, vol. 16, p. 308) Presence of aluminum chloride on aromatic hydrocarbons and phenolic ethers shown. In the course of the investigation on the hydrogen cyanide sesquichlorohydrate, this Bodies also left to act on tertiary amines and were thereby surprising new ones Get results.
Läfst man z. B. Blausäuresesquichlorhydrat auf Dimethylanilin einwirken, so tritt Condensation ein, ohne dafs es nöthig ist, Aluminiumchlorid zuzufügen. Höchstwahrscheinlich verläuft die Reaction zunächst analog der Einwirkung desBIausäuresesquichlorides auf Kohlenwasserstoffe und Phenoläther, indem sich intermediär das Teframethyldiamidobenzhydrylamin, d. h. die Leukobase des AuraminsIf you let z. B. prussic acid sesquichlorohydrate act on dimethylaniline, then condensation occurs without the need to add aluminum chloride. Most likely it will happen the reaction initially analogous to the action of the organic acid sesquichloride on hydrocarbons and phenol ethers, in which teframethyldiamidobenzhydrylamine, d. H. the leuco base of auramine
[CeH1N(CHJt]2 C H- NH,[CeH 1 N (CHJt] 2 C H-NH,
bildet. Diese Verbindung setzt sich indessen, wie durch Patent Nr. 64270 bekannt geworden ist, sofort mit einem weiteren Molecül Dimethylanilin zur Leukobase des Krystallvioletts umforms. However, this connection continues, as made known by patent no is, immediately with another molecule of dimethylaniline to the leuco base of crystal violet
[C6 H, N(CHJ,], CH[NH,'+H C6 H1 N(C HJ, = NH3 + C H[C6 H1N(CHJ, [C 6 H, N (CHJ,], CH [NH, '+ HC 6 H 1 N (C HJ, = NH 3 + CH [C 6 H 1 N (CHJ,
In genau derselben Weise gelangt man bei Anwendung anderer tertiärer Amine zu den entsprechenden Leukobasen.In exactly the same way one arrives at the use of other tertiary amines corresponding leuco bases.
i. Leukobase aus Dimethylanilin (Krystallviolettleukobase). i. Leuco base from dimethylaniline (crystal violet leuco base).
15 kg Dimethylanilin werden ca. 5 Stunden lang mit 5 kg Blausäuresesquichlorhydrat auf 120 bis 1300 erhitzt. Das Reactionsproduct wird in Wasser .gegossen, mit Natronlauge alkalisch gemacht und das überschüssige Dimethylanilin mit Wasserdämpfen übeYgetrieben. Es hinterbleibt dann in fast theoretischer Ausbeute die Leukobase des Krystallvioletts. Durch Erwärmen mit wenig Alkohol, wodurch die Verunreinigungen entzogen werden, wird dieselbe in weifsen, silberglänzenden Blättchen erhalten, die aus einer Mischung von Benzol und Ligroi'n in Form prächtiger weilser Nadeln krystallisiren und direct den richtigen Schmelzpunkt 1730 zeigen.15 kg dimethylaniline are heated for about 5 hours with 5 kg of 120 to 130 Blausäuresesquichlorhydrat on 0th The reaction product is poured into water, made alkaline with sodium hydroxide solution, and the excess dimethylaniline is driven over with steam. The leuco base of crystal violet then remains in an almost theoretical yield. Be removed by heating with a small amount of alcohol, whereby the impurities in the same whites is obtained silvery flakes which crystallize from a mixture of benzene and Ligroi'n in the form of needles and splendid weilser direct show the correct melting point 173 0th
2. Leukobase aus Methylbenzylanilin.2. Methylbenzylaniline leuco base.
50 kg Methylbenzylanilin und 10 kg Blausäuresesquichlorid werden mehrere Stunden lang auf ca. 1500 erhitzt. Das rothbraun gefärbte Schmelzproduct wird mit Wasser übergössen, mit Natronlauge alkalisch gemacht und mit überhitztem Wasserdampf das überschüssige Methylbenzylanilin abdestillirt. Die hinterbleibende Leukobase wird mit Salzsäure aufgenommen und durch Zusatz von Natrium-50 kg and 10 kg Methylbenzylanilin Blausäuresesquichlorid be heated for several hours to approximately 150 0th The red-brown colored enamel is poured over with water, made alkaline with caustic soda, and the excess methylbenzylaniline is distilled off with superheated steam. The remaining leuco base is absorbed with hydrochloric acid and by adding sodium
acetat wieder ausgefällt. Sie scheidet sich dabei als OeI ab, welches nach einiger Zeit dickflüssig wird.acetate precipitated again. It is deposited as an oil, which becomes thick after some time will.
Zur .weiteren Reinigung wird die Substanz mit etwas warmem Alkohol behandelt, .wobei leicht lösliche Verunreinigungen in Lösung gehen. ■' Der Rückstand wird in Aether gelöst, abfiltrirt und die Lösung zur Trockne verdampft., Die Base hinterbleibt als braunes, bei gewöhnlicher Temperatur zähflüssiges OeI, welches gegen o° zu einer spröden Masse erstarrt. Dieselbe ist in kaltem Alkohol sehr schwer löslich, etwas leichter in heifsem, unlöslich in Ligro'in. In Benzol, Aether und Eisessig löst sich die Substanz schon in der Kälte in jedem Verhältnifs. Die Lösung in Eisessig nimmt bei Zusatz von etwas Bleisuperoxyd sofort eine tief blaugrüne Farbe an.The substance is used for further cleaning treated with a little warm alcohol, where easily soluble impurities go into solution. ■ 'The residue is dissolved in ether, filtered off and the solution evaporated to dryness., The base remains behind as a brown, with Oil that is viscous at ordinary temperature and solidifies to a brittle mass towards 0 °. It is very sparingly soluble in cold alcohol, somewhat more easily in hot alcohol, insoluble in Ligro'in. In benzene, ether and glacial acetic acid, the substance dissolves in everyone even in the cold Proportion. The solution in glacial acetic acid immediately absorbs a little lead peroxide deep blue-green color.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE105198C true DE105198C (en) |
Family
ID=375506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT105198D Active DE105198C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE105198C (en) |
-
0
- DE DENDAT105198D patent/DE105198C/de active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE105198C (en) | ||
| DE539403C (en) | Process for the preparation of N-haloacylarylsulfamides | |
| DE634275C (en) | Process for the preparation of N-arylglucamines | |
| DE17340C (en) | Process for the preparation of a blue dye | |
| DE642148C (en) | Process for the preparation of clusters of phenylenediamines | |
| DE206537C (en) | ||
| DE644999C (en) | Process for the preparation of carboxylated carboline compounds | |
| DE724161C (en) | Process for the preparation of condensation products of the isoquinoline series | |
| DE495336C (en) | Process for the preparation of basic oxime ethers and their salts | |
| DE602338C (en) | Process for the production of dyes | |
| DE581328C (en) | Process for the preparation of acridone and substituted acridones | |
| DE462843C (en) | Process for the preparation of an iodine derivative of a diamino alcohol which is readily soluble in water | |
| DE305885C (en) | ||
| DE335877C (en) | Process for the preparation of ethers of p-oxyphenylcarbamide | |
| DE513205C (en) | Process for the preparation of derivatives of the aminoarylantimony compounds | |
| DE285604C (en) | ||
| DE528270C (en) | Process for the preparation of ephedrine derivatives | |
| DE737193C (en) | Process for the preparation of unsymmetrical heptamethine cyanine dyes | |
| DE582245C (en) | Process for the preparation of basic particles of catechol | |
| DE601720C (en) | Process for the preparation of nitro dyes | |
| DE537767C (en) | Production of acridyl-9-carbamic acid esters | |
| AT105341B (en) | Process for the representation of ice colors (development colors). | |
| DE116354C (en) | ||
| DE452064C (en) | Process for the preparation of organic phosphorus compounds | |
| DE420754C (en) | Process for the preparation of chlorine-substituted aromatic amines |