DE49857C - Process for the preparation of amido - /? - naphthol and a - (j - dioxynaphthalene disulfonic acids - Google Patents
Process for the preparation of amido - /? - naphthol and a - (j - dioxynaphthalene disulfonic acidsInfo
- Publication number
- DE49857C DE49857C DENDAT49857D DE49857DA DE49857C DE 49857 C DE49857 C DE 49857C DE NDAT49857 D DENDAT49857 D DE NDAT49857D DE 49857D A DE49857D A DE 49857DA DE 49857 C DE49857 C DE 49857C
- Authority
- DE
- Germany
- Prior art keywords
- ponceau
- preparation
- naphthol
- dioxynaphthalene
- amido
- 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.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 title claims description 13
- 150000007513 acids Chemical class 0.000 title claims description 8
- 125000003368 amide group Chemical group 0.000 title 1
- 230000002378 acidificating Effects 0.000 claims description 7
- 159000000000 sodium salts Chemical class 0.000 claims description 6
- 235000002639 sodium chloride Nutrition 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- HPGGPRDJHPYFRM-UHFFFAOYSA-J Tin(IV) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 3
- 239000000987 azo dye Substances 0.000 claims description 2
- 230000000875 corresponding Effects 0.000 claims description 2
- HSXUHWZMNJHFRV-QIKYXUGXSA-L orange G Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1\N=N\C1=CC=CC=C1 HSXUHWZMNJHFRV-QIKYXUGXSA-L 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- OJDKOFDWEFUYHH-PJPCBWKISA-N (4S)-5-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-3-carboxy-1-[[(2S,3R)-1-[[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl Chemical compound NCCCC[C@H](N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 OJDKOFDWEFUYHH-PJPCBWKISA-N 0.000 claims 1
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims 1
- -1 Echtroth D Chemical compound 0.000 claims 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N Ethyl phenyl ether Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 claims 1
- 101700043280 FST Proteins 0.000 claims 1
- 238000010411 cooking Methods 0.000 claims 1
- OBRMNDMBJQTZHV-UHFFFAOYSA-N cresol red Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C=C(C)C(O)=CC=2)=C1 OBRMNDMBJQTZHV-UHFFFAOYSA-N 0.000 claims 1
- TUAHFTHBSAWMRI-DSDYZSRDSA-L disodium;(8Z)-8-(naphthalen-1-ylhydrazinylidene)-7-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(N\N=C3/C(=O)C=CC=4C=C(C=C(C=43)S([O-])(=O)=O)S(=O)(=O)[O-])=CC=CC2=C1 TUAHFTHBSAWMRI-DSDYZSRDSA-L 0.000 claims 1
- IVNZBWNBYXERPK-DZGBHZPSSA-K trisodium;(8Z)-7-oxo-8-[(4-sulfonatonaphthalen-1-yl)hydrazinylidene]naphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N\N=C3/C(=O)C=CC=4C=C(C=C(C=43)S([O-])(=O)=O)S(=O)(=O)[O-])=CC=C(S([O-])(=O)=O)C2=C1 IVNZBWNBYXERPK-DZGBHZPSSA-K 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229920001864 tannin Polymers 0.000 description 3
- 239000001648 tannin Substances 0.000 description 3
- 235000018553 tannin Nutrition 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VXMKYRQZQXVKGB-CWWHNZPOSA-N Tannin Chemical compound O([C@H]1[C@H]([C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]([C@H]2O)O1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 VXMKYRQZQXVKGB-CWWHNZPOSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- CUXQLKLUPGTTKL-UHFFFAOYSA-M Microcosmic salt Chemical compound [NH4+].[Na+].OP([O-])([O-])=O CUXQLKLUPGTTKL-UHFFFAOYSA-M 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/41—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton
- C07C309/43—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTPATENT OFFICE
Sulfosäuren, des benachbarten α - β - Dioxynaphtalins (ß-Hydronaphtochinons) sind bis jetzt nicht bekannt gewesen. Disulfosäuren dieses Körpers lassen sich auf nachfolgende Weise leicht und glatt gewinnen.Sulfonic acids, of the neighboring α - β - dioxynaphthalene (ß-hydronaphtoquinones) have not been known up to now. Disulfonic acids of this body can be traced back to Winning way easily and smoothly.
Wenn man die aus einer der beiden bekannten Disulfosäuren R und G des ß-Naphtols oder aus einem Gemisch derselben mit Hülfe beliebiger Diazoverbindungen in bekannter Weise hergestellten Azofarbstoffe mittelst saurer Zinnchlorürlösung reducirt, so erhält man eine farblose Lösung, welche neben dem zur Diazotirung benutzten, bei der Reduction regenerirten Amin das saure Natriumsalz einer Amido-ß-Naphfoldisulfosäure enthält, welches aus dieser Lösung durch Zusatz von Kochsalz in krystallisirter Form abgeschieden werden kann.If one of the two well-known disulfonic acids R and G of ß-naphthol or from a mixture of these with the aid of any diazo compounds in a known manner Azo dyes prepared in this way are reduced by means of an acidic tin chloride solution a colorless solution, which was used in addition to that for diazotization, in the reduction regenerated amine contains the acidic sodium salt of an amido-ß-naphfoldisulfonic acid, which precipitated in crystallized form from this solution by the addition of common salt can be.
40 kg des unter dem Namen »Orange G« im Handel bekannten Natriumsalzes der Anilinazo - β - naphtoldisulfosäure werden in 250 1 siedenden Wassers gelöst. Zu dieser Lösung fügt man die warme Auflösung von 45 kg Zinnchlorür in 50 1 Salzsäure (spec. Gewicht 1,19), worauf alsbald völlige' Entfärbung der Flüssigkeit eintritt. Löst man in der erhaltenen farblosen Lösung 60 kg Kochsalz auf, so scheidet sich alsbald das saure Natriumsalz der Amidonapbtoldisulfosäure:40 kg of the sodium salt of anilinazo, known commercially under the name "Orange G" - β - naphthol disulphonic acid are dissolved in 250 liters of boiling water. To this solution the warm solution of 45 kg of tin chloride in 50 l of hydrochloric acid (spec. weight 1.19), whereupon complete 'discoloration' the liquid enters. If you dissolve 60 kg of common salt in the colorless solution obtained, so the acidic sodium salt of amidonapbtoldisulfonic acid soon separates:
(NH,(NH,
C HC H
s O3Hs O 3 H
S O3NaSO 3 Na
in weifsen Krystallen ab, welche gesammelt und getrocknet werden können in white crystals, which can be collected and dried
Dieses Salz erleidet, wenn man es in siedendem Wasser auflöst und die Lösung kurze Zeit im Sieden erhält, eine moleculare Umlagerung, welche durch nachfolgende Gleichung ausgedrückt wird:This salt suffers if you dissolve it in boiling water and the solution briefly Time in the boil, a molecular rearrangement, which is shown by the following equation is expressed:
OHOH
S O2H 'SO 2 H '
S O3NaSO 3 Na
OH OHOH OH
S O3 SO 3
S O3Na ' ,
d. h. das saure Natriumsalz der Amidoß-naphtoldisulfosäure verwandelt sich unter
Wasseraufnahme in das neutrale Natriumammoniumsalz der entsprechenden Dioxynaphtalindisulfosäure,
und zwar treten. sämmtliche beschriebenen Erscheinungen in ganz
gleicher Weise ein, ob nun ein Derivat der einen oder der anderen der beiden bekannten
Naphtoldisulfosäuren oder ein Gemisch beider als Ausgangsproduct zur Anwendung kam. SO 3 Na ',
that is, the acidic sodium salt of amidos-naphtholedisulphonic acid is transformed into the neutral sodium ammonium salt of the corresponding dioxynaphthalenedisulphonic acid when water is absorbed. All of the described phenomena apply in exactly the same way, whether a derivative of one or the other of the two known naphthol disulfonic acids or a mixture of both was used as the starting product.
Die entstandenen Disulfosäuren des Dioxynaphtälins sind aufserordentlich leicht löslich. Behufs ihrer Verwendung ist eine Abscheidung gar nicht erforderlich, sondern die durch Aufkochen der Amidonaphtolverbindung mit Wasser erhaltene Lösung kann direct benutzt werden. Diese Benutzung gründet sich darauf, dafs diese Lösung fast in allen Eigenschaften einer Auflösung von Tannin entspricht und sich infolge dessen zu allen Anwendungen eignet, für welche bisher Tannin benutzt wurde. Sie fällt z. B. eine mit Essigsäure leicht angesäuerte Leimlösung und läfst sichThe resulting disulfonic acids of dioxynaphthalene are extremely easily soluble. For their use, separation is not required at all, but that by boiling the solution obtained with water of the amidonaphthol compound can be used directly. This use is based on that this solution corresponds in almost all properties to a dissolution of tannin and As a result, it is suitable for all applications for which tannin was previously used became. She falls z. B. a glue solution slightly acidified with acetic acid and dissolves
daher zum Gerben thierischer Häute benutzen. Sie fällt ferner die Auflösungen aller basischen Anilinfarbstorfe und kann daher in der Färberei und namentlich im Baumwolldruck statt des Tannins als Beize angewendet werden. Aus diesem Grunde sollen die Disulfösäuren des a-ß-Dioxynaphtalins als »Naphtotannine« bezeichnet werden.therefore use it for tanning animal hides. It also falls on the dissolutions of all basic ones Aniline peat and can therefore be used in dyeing and especially in cotton printing instead of Tannins can be used as a stain. For this reason, the disulfoic acids des a-ß-Dioxynaphtalins are called "naphtotannins".
Claims (1)
Publications (1)
Publication Number | Publication Date |
---|---|
DE49857C true DE49857C (en) |
Family
ID=324753
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT49857D Expired - Lifetime DE49857C (en) | Process for the preparation of amido - /? - naphthol and a - (j - dioxynaphthalene disulfonic acids |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE49857C (en) |
-
0
- DE DENDAT49857D patent/DE49857C/en not_active Expired - Lifetime
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