CH106401A - Process for the production of a new intermediate product in the tar color industry. - Google Patents
Process for the production of a new intermediate product in the tar color industry.Info
- Publication number
- CH106401A CH106401A CH106401DA CH106401A CH 106401 A CH106401 A CH 106401A CH 106401D A CH106401D A CH 106401DA CH 106401 A CH106401 A CH 106401A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- phenylenediamine
- production
- hol
- intermediate product
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000013067 intermediate product Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 7
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 7
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 6
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 229910001919 chlorite Inorganic materials 0.000 claims 1
- 229910052619 chlorite group Inorganic materials 0.000 claims 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- DRXLHYPPJRAJSL-UHFFFAOYSA-N n-(3-aminophenyl)formamide Chemical compound NC1=CC=CC(NC=O)=C1 DRXLHYPPJRAJSL-UHFFFAOYSA-N 0.000 description 2
- 229940044174 4-phenylenediamine Drugs 0.000 description 1
- 101100108644 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) alo-1 gene Proteins 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Paper (AREA)
Description
Verfahren zur Herstellung eines neuen Zwischenproduktes der Teerfarbenindustrie. Es wurde gefunden, dass man ein neues Zwischenprodukt, das symmetrische ditertiäre Kondensationsprodukt von zwei Mol. Cyanur- ehlorid, einem Mol. 1,4-Phenylendiamin, zwei Mol. 1,3-Phenylendiamin - 4 - sulfosäure und zwei Mol. 1,3-Phenylendi,amin, erhält,
wenn man auf zwei Mol. Cyanurchlorid in beliebi- ger Reihenfolge ein AIo1. 1,4-Phenylendi-amin, zwei Mol. 1,3-Phenylendia.min - 4 - sulfosäure und zwei Mod. Monoformyl-1,3-Phenylendia- min einwirken lässt, und das so erhaltene Pro dukt verseift.
Diese Kondensation wird durch Zusam menrühren der Komponenten in einem geeig neten Verdünnungsmittel durchgeführt, und es wurde gefunden, dass Wasser als solches in Überraschender Weise sehr gut geeignet ist. Das symmetrische ditertiäre Kondensations produkt aus zwei Mol. Cyanurchlorid mit einem Mol. 1,4-Phenylendi.amin, zwei Mol. 1,3-Phenylendiamin - 4 - sulfosäure und zwei 112o1. 1,3-Phenylendiamin bildet als Alkalisalz ein in Wasser lösliches,
fast farbloses Pulver. Es enthält 4 diazotierbare Aminogruppen, kein reaktionsfähiges Chloratom mehr und stellt ein wertvolles Ausgangsmaterial zur Herstellung von Farbstoffen dar.
<I>Beispiel:</I> In eine Aussehlemmung von 37 Teilen Cyanurchlorid und<B>1000</B> Teilen Wasser giesst. man eine Lösung aus 37,8 Teilen 1,3-Phenyl- endiamin-4-sulfosäure und 10.8 Teilen Soda in 1000 Teilen Wasser.
Die Temperatur -wird bei 0 gehalten und die gebildete Mineralsäure neutralisiert. Sobald die Komponenten ver schwunden sind, fügt man 10,8 Teile 1,4 Phenylendiamin hinzu und rührt mehrere Stunden auf 40 bis<B>50'.</B> Hierauf neutralisiert man genau, fügt 27,2 Teile 2lonoformyl-1.3- Phenylendiamin hinzu und kocht einige Zeit am RückfluZkühler. Wenn das Monoformyl- 1,3-Phenylendiamin verschwunden ist, wer den 20 Teile Natronhydrat zugegeben und noch eine Viertelstunde gekocht.
Nach dem Erkalten wird das symmetrische ditertiäre Kondensationsprodukt aus zwei Mol. Cyanur- ,ehlorid, einem Mol. 1,4-Phenylendia.min, zwei
EMI0002.0001
Hol. <SEP> 1,3-Phenylendiamin <SEP> - <SEP> $ <SEP> - <SEP> sulfos*i.ure <SEP> und
<tb> zwei <SEP> Mol. <SEP> 1,3-Phenylendiamin <SEP> durch <SEP> Aus salzen <SEP> und <SEP> Aussäuern <SEP> isoliert.
Process for the production of a new intermediate product in the tar color industry. It has been found that a new intermediate product, the symmetrical ditertiary condensation product of two moles of cyanuric chloride, one mole of 1,4-phenylenediamine, two moles of 1,3-phenylenediamine-4-sulfonic acid and two moles of 1,3 -Phenylenedi, amine, receives,
if you add an Alo1 to two moles of cyanuric chloride in any order. 1,4-phenylenediamine, two moles. 1,3-phenylenediamine-4-sulfonic acid and two mod. Monoformyl-1,3-phenylenediamine are allowed to act, and the product thus obtained is saponified.
This condensation is carried out by stirring the components together in a suitable diluent, and it has been found that water as such is surprisingly very suitable. The symmetrical ditertiary condensation product of two moles of cyanuric chloride with one mole of 1,4-phenylenediamine, two moles of 1,3-phenylenediamine-4-sulfonic acid and two 112o1. As an alkali salt, 1,3-phenylenediamine forms a water-soluble,
almost colorless powder. It contains 4 diazotizable amino groups, no more reactive chlorine atom and is a valuable starting material for the production of dyes.
<I> Example: </I> Pour 37 parts of cyanuric chloride and <B> 1000 </B> parts of water into a lockout. a solution of 37.8 parts of 1,3-phenylenediamine-4-sulfonic acid and 10.8 parts of soda in 1000 parts of water.
The temperature is kept at 0 and the mineral acid formed is neutralized. As soon as the components have disappeared, 10.8 parts of 1.4 phenylenediamine are added and the mixture is stirred for several hours at 40 to 50 '. This is followed by precise neutralization, 27.2 parts of 2lonoformyl-1,3-phenylenediamine are added and boil for some time on the reflux condenser. When the monoformyl-1,3-phenylenediamine has disappeared, who added 20 parts of sodium hydrate and cooked for a quarter of an hour.
After cooling, the symmetrical ditertiary condensation product of two moles of cyanuric chloride, one mole of 1,4-phenylenediamine, two
EMI0002.0001
Hol. <SEP> 1,3-phenylenediamine <SEP> - <SEP> $ <SEP> - <SEP> sulfos * i.ure <SEP> and
<tb> two <SEP> moles <SEP> 1,3-phenylenediamine <SEP> isolated by <SEP> from salts <SEP> and <SEP> acidifying <SEP>.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH103430T | 1922-09-07 | ||
| FR106401X | 1923-01-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH106401A true CH106401A (en) | 1924-08-16 |
Family
ID=25706463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH106401D CH106401A (en) | 1922-09-07 | 1923-11-28 | Process for the production of a new intermediate product in the tar color industry. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH106401A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2544071A (en) * | 1951-03-06 | Diethylenetrimelamine and method |
-
1923
- 1923-11-28 CH CH106401D patent/CH106401A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2544071A (en) * | 1951-03-06 | Diethylenetrimelamine and method |
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