CH149412A - Process for the production of a nitrogen-containing condensation product. - Google Patents
Process for the production of a nitrogen-containing condensation product.Info
- Publication number
- CH149412A CH149412A CH149412DA CH149412A CH 149412 A CH149412 A CH 149412A CH 149412D A CH149412D A CH 149412DA CH 149412 A CH149412 A CH 149412A
- Authority
- CH
- Switzerland
- Prior art keywords
- allo
- nitrogen
- production
- condensation product
- containing condensation
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000003929 acidic solution Substances 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 3
- 235000005811 Viola adunca Nutrition 0.000 claims description 3
- 240000009038 Viola odorata Species 0.000 claims description 3
- 235000013487 Viola odorata Nutrition 0.000 claims description 3
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000006396 nitration reaction Methods 0.000 claims description 3
- 150000002828 nitro derivatives Chemical class 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Braking Arrangements (AREA)
- Coloring (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Verfahren zai7 Herstellung eines sticlatoffhaltigen Kondensationsproduktes. Es wurde gefunden, dass man ein wert volles, stickstoffhaltiges Kondensationsprodukt erhalten kann, wenn man das aus dem durch direktes Nitrieren von allo-ms-Naphtodianthrorr und Reduzieren der entstandenen Nitrover- bindung dargestellte Amino-allo-ms-naphto- dianthron oder aus dem so dargestellten Nitro-allo-ms-rraphtodianthron selbst und Gly zerin oder seinen Derivaten durch Einwirkung wasserentziehender Mittel in saurer Lösung erhältliche
Pyridino-allo-ms-naphtodianthron in saurer Lösung mit einem dehydrierend wirkenden Mittel behandelt. Geeignete de hydrierend wirkende Mittel sind z. B. Braun stein, salpetrige Säure, Chromsäure, Alumi niumchlorid etc.
Das Reaktionsprodukt kristallisiert in orangefarbenen Nadeln und liefert auf Baum wolle aus blauvioletter Küpe kräftige, orange farbene, vorzüglich echte Färbungen.
<I>Beispiel 1:</I> 40 Teile des durch direkte Nitrierung von allo-ms-Naphtodianthron und Reduktion der entstandenen Nitroverbindung erhältlichen Amino-allo-ms-rraphtodianthroris werden in 1350 Teilen konzentrierter Schwefelsäure gelöst und nach Zugabe von 24 Teilen Nitro- benzol und 65 Teilen Glyzerin unter Rühren langsam auf 110-1200 C erhitzt. Wenn eine entnommene Probe eine chlorechte rote Fär bung liefert, lässt man abkühlen, giesst in Wasser, saugt ab, wäscht neutral und trock net.
Das erhaltena Pyridino-allo-ms-naphto- dianthron stellt ein braunrotes Pulver dar, löst sich in konzentrierter Schwefelsäure mit grüner Farbe, liefert eine rotviolette Küpe, aus der Baumwolle in kräftigen, roten Tönen von guter Echtheit gefärbt wird. Es kristal lisiert in roten Nadeln, die bei 350-352 C schmelzen.
10 Teile des Pyridino-allo-ms-naphtodian- throns werden in 150 Teilen konzentrierter Schwefelsäure gelöst. Darauf trägt man unter Rühren 10 Teile Braunstein ein, wobei unter Selbsterwärmung die grüne Farbe der Lösung in blauviolett übergeht. Nach Beendigung der Reaktion saugt man ab, giesst das Filtrat auf Eis und arbeitet wie üblich auf.
Das Reaktionsprodukt kann gegebenen falls über sein Oxoniumsalz oder Ammonium salz oder durch Behandeln mit Oxydations mitteln, z. B. in Form seiner wässerigen Paste mit Hypochlorit, gereinigt werden.
Verwendet man an Stelle von Monoamino- allo-ms-naphtodianthron das entsprechende Mononitro-allo-ms-naphtodianthron, wobei man die Darstellung des Pyridino-allo-ms-naphto- dianthrons bei 140-150 C vornimmt, und verfährt im übrigen in gleicher Weise wie oben angegeben, so erhält man das gleiche Produkt. <I>Beispiel 2:</I> 5 Teile Monoamino-allo-ms-naphtodian- thron werden in etwa 200 Teilen konzentrier ter Phosphorsäure bei 120 C gelöst. Man fügt 3-4 Teile Nitrobenzol und 6 Teile Gly zerin hinzu und erhitzt kurze Zeit auf 1_80 bis 190 C.
Nach dem Abkühlen giesst man auf Eis und arbeitet wie üblich auf. Das Reaktionsprodukt kann aus Nitrobenzol um kristallisiert werden. Man behandelt das er- haltene Reaktionsprodukt in der in Beispiel 1, Absatz 2, angegebenen Weise und erhält das gleiche Endprodukt wie in Beispiel 1.
Process zai7 Production of a sticlatoff-containing condensation product. It has been found that a valuable, nitrogen-containing condensation product can be obtained if the amino-allo-ms-naphthodianthrone prepared by direct nitration of allo-ms-naphthodianthrone and reducing the resulting nitro compound or from the so shown nitro-allo-ms-rraphtodianthron itself and glycerine or its derivatives obtainable by the action of dehydrating agents in acidic solution
Pyridino-allo-ms-naphtodianthron treated in acidic solution with a dehydrating agent. Suitable de hydrogenating agents are, for. B. brown stone, nitrous acid, chromic acid, aluminum chloride etc.
The reaction product crystallizes in orange-colored needles and delivers strong, orange-colored, extremely true colors on cotton from a blue-violet vat.
<I> Example 1: </I> 40 parts of the amino-allo-ms-rraphtodianthrone obtainable by direct nitration of allo-ms-naphtodianthrone and reduction of the nitro compound formed are dissolved in 1350 parts of concentrated sulfuric acid and, after addition of 24 parts of nitro benzene and 65 parts of glycerine slowly heated to 110-1200 ° C. with stirring. If a sample taken has a chlorine-fast red color, it is allowed to cool, poured into water, suction filtered, washed neutral and dried.
The obtained pyridino-allo-ms-naphthodianthrone is a brown-red powder, dissolves in concentrated sulfuric acid with a green color, provides a red-violet vat from which cotton is dyed in strong, red shades of good fastness. It crystallizes in red needles that melt at 350-352 C.
10 parts of the pyridino-allo-ms-naphtodian- throne are dissolved in 150 parts of concentrated sulfuric acid. 10 parts of manganese dioxide are then introduced, with stirring, the green color of the solution changing to blue-violet with self-heating. When the reaction has ended, the mixture is filtered off with suction, the filtrate is poured onto ice and worked up as usual.
The reaction product can, if appropriate, via its oxonium salt or ammonium salt or by treating with oxidizing agents, eg. B. in the form of its aqueous paste with hypochlorite, cleaned.
If, instead of monoamino-allo-ms-naphtodianthrone, the corresponding mononitro-allo-ms-naphtodianthrone is used, the pyridino-allo-ms-naphthodianthrone is represented at 140-150 C, and the rest of the procedure is the same as indicated above, the same product is obtained. <I> Example 2: </I> 5 parts of monoamino-allo-ms-naphthodianthron are dissolved in about 200 parts of concentrated phosphoric acid at 120.degree. 3-4 parts of nitrobenzene and 6 parts of glycerin are added and the mixture is heated to between 180 and 190 ° C. for a short time.
After cooling, pour onto ice and work up as usual. The reaction product can be recrystallized from nitrobenzene. The reaction product obtained is treated in the manner indicated in example 1, paragraph 2, and the same end product as in example 1 is obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE149412X | 1929-06-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH149412A true CH149412A (en) | 1931-09-15 |
Family
ID=5673323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH149412D CH149412A (en) | 1929-06-21 | 1930-06-20 | Process for the production of a nitrogen-containing condensation product. |
Country Status (2)
| Country | Link |
|---|---|
| AT (1) | AT149412B (en) |
| CH (1) | CH149412A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE756550C (en) * | 1938-12-04 | 1952-05-19 | Fried Krupp A G | Switching device of a drive transmission for rail vehicles, especially locomotives, consisting of a flow gear and a mechanical reversing gear |
| DE1003785B (en) * | 1953-08-01 | 1957-03-07 | Eisen & Stahlind Ag | Training of the drive switch used for power control for drives of vehicles, in particular of rail vehicles |
| DE967305C (en) * | 1954-05-18 | 1957-10-31 | Maybach Motorenbau G M B H | Power transmission, in particular for motor vehicles |
-
1930
- 1930-06-20 CH CH149412D patent/CH149412A/en unknown
-
1936
- 1936-05-07 AT AT149412D patent/AT149412B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AT149412B (en) | 1937-04-26 |
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