AT22981B - Process for the preparation of Indoxyl BEzw. Indigo and its homologues. - Google Patents
Process for the preparation of Indoxyl BEzw. Indigo and its homologues.Info
- Publication number
- AT22981B AT22981B AT22981DA AT22981B AT 22981 B AT22981 B AT 22981B AT 22981D A AT22981D A AT 22981DA AT 22981 B AT22981 B AT 22981B
- Authority
- AT
- Austria
- Prior art keywords
- bezw
- indoxyl
- homologues
- indigo
- preparation
- Prior art date
Links
- PCKPVGOLPKLUHR-UHFFFAOYSA-N indoxyl Chemical group C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- 235000000177 Indigofera tinctoria Nutrition 0.000 title description 4
- 229940097275 indigo Drugs 0.000 title description 4
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 title description 4
- 238000009833 condensation Methods 0.000 claims description 9
- 230000005494 condensation Effects 0.000 claims description 9
- -1 aromatic glycines Chemical class 0.000 claims description 3
- 239000003518 caustics Substances 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000219995 Wisteria Species 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Catalysts (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Indoxyl bezw. Indigo und dessen Homologen.
Die bisherigen Verfahren, Indoxyl bezw. Indigo und dessen Homologen aus aromatischen Glyzinen und deren Derivaten durch Kondensation derselben mit Alkalihydroxyden usw. darzustellen, fuhren zu mangelhaften Ausbeuten ; so ergibt bekanntlich die hermann'ache
EMI1.1
das Glyzin gerochnet.
Vorliegender Erfindung nach lassen sich diese Ausbeuten beträchtlich erhöhen, wenn man die Kondensationen bei Gegenwart von Ammoniakgas bewerkstelligt. Zur Ausübung des vorliegenden Verfahrens wird Ammoniakgas über, in oder durch das Gemenge der aromatischen Glyzine und der Kondensationsmittel bei Abwesenheit oder Anwesenheit von Erdalkalimetallen bezw. deren Verbindungen oder Metallen der Magnesiumgruppe bezw. deren Verbindungen während des Kondensationsprozesses stetig bei normalem, erhöhtem oder vermindertem Drucke streichen gelassen.
Es soll nicht unerwähnt bleiben, dass die Darstellung von Indoxyl durch Kondensation
EMI1.2
günstigen Einwirkung des Ammoniakgases auf die Kondensationen der aromatischen Glyzine mit den billigen und leicht zugänglichen At7. alkalien mit oder ohne Zusätze von anderen Kondensationsmitteln beruht, bezieht sich auf das Durchleiten von, von aussen zugeführtem Ammoniakgas durch die Reaktionsmischung.
Beispiel : 3 Gewichtsteile trockenes itzkali oder ein Gemisch von 5 Gewichtsteilen Ätzkali und 3#5 Gewichtsteilen Ätznatron, 1 -2 Gewichtsteilen Ätzkalk, 1 Gewichts- teil Phenylglyzinkalium werden innig vermischt in ein entsprechendes Gefäss gebracht und in dasselbe trockenes Ammoniakgas eingeleitet, das man zweckmässig während des ganzen Kondensationsprozesses, den man vorteilhaft bei einer zwischen 50-3000 C liegenden
EMI1.3
kann, wird dasselbe in Wasser gelöst und aus dieser Lösung der Indigo durch LuftsauerstoffoderanderegeeigneteOxydationsmittelabgeschieden.
Beispiele für die Kondensation bei erhöhtem oder vermindertem Druck, sowie für die anderen Derivate (Äther, Amide usw.) der aromatischen Glyzine ergeben sich nach obigem von selbst.
Um sich Beispiele für Zusätze von Verbindungen der Magnesiumgruppe - Metalle - zu konstruieren, braucht man im obigen Beispiel bloss den Ätzkalk, z. B. durch Magnesium. zu ersetzen.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of Indoxyl BEzw. Indigo and its homologues.
The previous processes, Indoxyl respectively. Producing indigo and its homologues from aromatic glycines and their derivatives by condensation of the same with alkali metal hydroxides etc. lead to poor yields; as is well known, the hermann'ache results
EMI1.1
smelled the wisteria.
According to the present invention, these yields can be increased considerably if the condensations are carried out in the presence of ammonia gas. To exercise the present method, ammonia gas is BEZW over, in or through the mixture of aromatic glycines and the condensing agent in the absence or presence of alkaline earth metals. their compounds or metals of the magnesium group BEZW. their compounds are steadily deleted during the condensation process at normal, increased or reduced pressure.
It should not go unmentioned that the representation of indoxyl by condensation
EMI1.2
favorable effect of ammonia gas on the condensation of aromatic glycine with cheap and easily accessible At7. alkalis with or without the addition of other condensation agents refers to the passage of externally supplied ammonia gas through the reaction mixture.
Example: 3 parts by weight of dry itzkali or a mixture of 5 parts by weight of caustic potash and 3 # 5 parts by weight of caustic soda, 1-2 parts by weight of caustic lime, 1 part by weight of phenylglyzine potassium are intimately mixed, placed in a corresponding vessel and introduced into the same dry ammonia gas that is conveniently used during of the entire condensation process, which is advantageous at a temperature between 50-3000 C.
EMI1.3
can, it is dissolved in water and the indigo is separated from this solution by atmospheric oxygen or other suitable oxidizing agents.
Examples of the condensation at increased or reduced pressure, as well as for the other derivatives (ethers, amides, etc.) of the aromatic glycine result from the above automatically.
In order to construct examples of additions of compounds of the magnesium group - metals -, in the above example only quick lime is needed, e.g. B. by magnesium. to replace.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT22981T | 1903-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT22981B true AT22981B (en) | 1906-02-10 |
Family
ID=3531749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT22981D AT22981B (en) | 1903-02-22 | 1903-02-22 | Process for the preparation of Indoxyl BEzw. Indigo and its homologues. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT22981B (en) |
-
1903
- 1903-02-22 AT AT22981D patent/AT22981B/en active
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