CH128644A - Process for the preparation of the diazo compound of para-amidoazobenzene. - Google Patents
Process for the preparation of the diazo compound of para-amidoazobenzene.Info
- Publication number
- CH128644A CH128644A CH128644DA CH128644A CH 128644 A CH128644 A CH 128644A CH 128644D A CH128644D A CH 128644DA CH 128644 A CH128644 A CH 128644A
- Authority
- CH
- Switzerland
- Prior art keywords
- amidoazobenzene
- diazo compound
- preparation
- para
- weight
- Prior art date
Links
- 150000008049 diazo compounds Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung der Diazoverbindung von para-Ainidoazobenzol. Gegenstand dieser Erfindung ist ein Ver fahren zur Darstellung der Diazoverbindung des p-Amidoazobenzols, dadurch gekennzeich net, dass man p-Amidoazobenzol mit Halogen sulfonsäure oder deren Estern in Gegenwart einer tertiären Base in seine Sulfaminsäure überführt und diese mit Mineralsäure und Nitrit behandelt.
<I>Beispiel:</I> In 300 Gewichtsteilen trockenes Pyridin lässt man bei<B>350</B> 36 Gewichtsteile Chlor- sulfonsäure eintropfen, trägt dann 39,4 Ge wichtsteile p-Amidoazobenzol ein und erwärmt eine Stunde auf GO bis 65 0. Man giesst in eine wässerige Lösung von 48 Gewichtsteilen Ätznatron und trennt das Pyridin durch Wasserdampfdestillation ab. Aus dem Destil- lationsrückstand kristallisiert beim Erkalten das Natriumsalz der Sulfaminsäure aus.
Die letzten Reste können durch Aussaizen ge wonnen werden.
Zur Diazotierung suspendiert man 20 Ge- wichtsteile eines 82,3 %igen Produktes in 200 Gewichtsteilen Wasser, fügt 30 Gewichtsteile 20 %iger Salzsäure zu und lässt unter Rühren eine Lösung von 3,85 Gewichtsteilen Natrium nitrit in 25 Gewichtsteilen Wasser einfliessen.
Die Diazoverbindung des p-Amidoazobenzols scheidet sich als bräunliche voluminöse Masse ab. Bei grösseren Verdünnungen erhält man eine rötlich gefärbte Diazolösung. Sowohl diese, als auch die feste Diazoverbindung geben mit ss-Naphtol gekuppelt einen leuch tend blaustichigroten, unlöslichen Farbstoff.
Process for the preparation of the diazo compound of para-ainidoazobenzene. This invention relates to a process for the preparation of the diazo compound of p-amidoazobenzene, characterized in that p-amidoazobenzene is converted into its sulfamic acid with halogen sulfonic acid or its esters in the presence of a tertiary base and this is treated with mineral acid and nitrite.
<I> Example: </I> In 300 parts by weight of dry pyridine, 36 parts by weight of chlorosulphonic acid are added dropwise at <B> 350 </B>, 39.4 parts by weight of p-amidoazobenzene are then added and the mixture is heated to GO for one hour 65 0. It is poured into an aqueous solution of 48 parts by weight of caustic soda and the pyridine is separated off by steam distillation. The sodium salt of sulfamic acid crystallizes out of the distillation residue on cooling.
The last remnants can be won by sawning out.
For diazotization, 20 parts by weight of an 82.3% product are suspended in 200 parts by weight of water, 30 parts by weight of 20% hydrochloric acid are added and a solution of 3.85 parts by weight of sodium nitrite in 25 parts by weight of water is allowed to flow in with stirring.
The diazo compound of p-amidoazobenzene separates out as a brownish voluminous mass. Larger dilutions result in a reddish colored diazo solution. Both this and the solid diazo compound, coupled with s-naphtol, give a bright blue-tinged, insoluble dye.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE128644X | 1926-03-30 | ||
| CH126406T | 1927-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH128644A true CH128644A (en) | 1928-11-01 |
Family
ID=25710672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH128644D CH128644A (en) | 1926-03-30 | 1927-03-24 | Process for the preparation of the diazo compound of para-amidoazobenzene. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH128644A (en) |
-
1927
- 1927-03-24 CH CH128644D patent/CH128644A/en unknown
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