DE482944C - Process for the preparation of uniform 1-monosulfonic acids of the 2-oxynaphthalene-3-carboxylic acid arylides - Google Patents
Process for the preparation of uniform 1-monosulfonic acids of the 2-oxynaphthalene-3-carboxylic acid arylidesInfo
- Publication number
- DE482944C DE482944C DEF59930D DEF0059930D DE482944C DE 482944 C DE482944 C DE 482944C DE F59930 D DEF59930 D DE F59930D DE F0059930 D DEF0059930 D DE F0059930D DE 482944 C DE482944 C DE 482944C
- Authority
- DE
- Germany
- Prior art keywords
- oxynaphthalene
- carboxylic acid
- uniform
- preparation
- arylides
- 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
Links
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
- C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
- C07C309/60—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- 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
- C07C309/33—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of six-membered aromatic rings being part of condensed ring systems
- C07C309/34—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of six-membered aromatic rings being part of condensed ring systems formed by two rings
- C07C309/35—Naphthalene sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von einheitlichen 1-Iffonosulfosäuren der 2-Oxynaphthalin-3-carbonsäurearylide Es wurde gefunden, daß man einheitlich in i-Stellung sulfierte z-Oxynaphthalin-3-carbonsäurearylide erhält, wenn man 2-Oxynaphthalin-3-carbonsäurearylide in Gegenwart indifferenter Lösungsmittel in der Wärme mit der äquivalenten Menge Chlorsulfonsäure oder deren Ester behandelt. Daß die erhaltenen sulfierten Produkte die Sulfogruppe in der i-Stellung enthalten, geht daraus hervor, daß bei der Einwirkung von z. B. Broni unter Verlust der Sulfogruppe i -Brom-2 -oxynaphthalin-3 -carbonsäurearylide gebildet werden, wie daraus, daß bei der Einwirkung von Diazoverbindungen schwefelfreie, unlösliche Azofarbstoffe gebildet werden, welche identisch sind mit den mit gleichen Diazoverbindungen aus den entsprechenden 2-Oxynaphthalin-3-carbonsäurearyliden erhältlichen.Process for the preparation of uniform 1-Iffonosulfoäuren der 2-Oxynaphthalene-3-carboxylic acid arylides It has been found that one is uniformly in the i-position sulfated z-oxynaphthalene-3-carboxylic acid arylides are obtained when 2-oxynaphthalene-3-carboxylic acid arylides in the presence of inert solvents in the heat with the equivalent amount Treated chlorosulfonic acid or its ester. That the sulfated products obtained contain the sulfo group in the i-position, it follows that upon exposure from Z. B. Broni with loss of the sulfo group i -Bromo-2 -oxynaphthalene-3-carboxylic acid arylides are formed, as from the fact that when diazo compounds act, sulfur-free, insoluble azo dyes are formed which are identical to those with the same Diazo compounds obtainable from the corresponding 2-oxynaphthalene-3-carboxylic acid arylides.
Nach dem Verfahren der Patentschrift 397 313, welches die Verwendung von Schwefelsäure oder Monohydrat vorschreibt, entstehen nur Gemische verschiedener Sulfosäuren der 2-Oxynaphthalin-3-carbonsäurearylamide, welche den Sulforest in 6-, ?- und auch in i-Stellung enthalten. Nur nach sehr umständlichem Verfahren sind aus diesem Gemische die allein wertvollen i-Sulfosäuren zu gewinnen und dazu nur in sehr unzureichender Menge.According to the process of patent specification 397 313, which prescribes the use of sulfuric acid or monohydrate, only mixtures of different sulfonic acids of the 2-oxynaphthalene-3-carboxylic acid arylamides are formed, which contain the sulfo radical in the 6-,? - and also in the i-position. The only valuable i-sulfonic acids can only be obtained from this mixture after a very laborious process, and only in very inadequate quantities.
Die i-Monosulfosäuren der 2-Oxynaphthalin-3-carbonsäurearyläde sind wichtige Zwischenprodukte zur Herstellung von Farbstoffen, und die - glatte, einheitliche Darstellung dieser in reinem Zustande bisher nicht bekannten Sulfosäuren stellt einen erheblichen technischen Fortschritt dar.The i-Monosulfosäuren the 2-oxynaphthalene-3-carbonsäurearyläde are important intermediates for the production of dyes, and - smooth, uniform presentation of this previously unknown in the pure state sulfonic acids represents a significant technical progress.
Beispiele 26,3 Gewichtsteile 2-Oxynaphthalin-3-carbonsäureanilid suspendiert znan in 2oo g Tetrachloräthan, erhitzt auf 8o' und läßt bei dieser Temperatur unter gutem Rühren langsam 15 g Chlorsulfonsäure zutropfen. Das schwach gelblich gefärbte, körnige Produkt saugt man ab, löst in Soda, filtriert und salzt aus. Man erhält so das Natriumsalz des i-Sulfo-2-oxynaphthalin-3-carbonsäureanilids in reiner Form. Es ist leicht löslich in Natronlauge, Soda, schwerer in Natriumacetat.EXAMPLES 26.3 parts by weight of 2-oxynaphthalene-3-carboxylic acid anilide suspended in 2oo g of tetrachloroethane, heated to 80 'and slowly added dropwise at this temperature with 15 g of chlorosulfonic acid. The pale yellowish colored, granular product is filtered off with suction, dissolved in soda, filtered and salted out. The sodium salt of i-sulfo-2-oxynaphthalene-3-carboxylic acid anilide is thus obtained in pure form. It is easily soluble in caustic soda, soda, more difficultly in sodium acetate.
2. In das siedende Gemisch von 62,2 g 2-Oxynaphthalin-3-carbonsäure-4'-chlor-2'-methyl-i'-anilld und 6oo g Tetrachlorkohlenstoff läßt man unter gutem Rühren 24 9 Chlorsulfonsäure zutropfen. Unter lebhafter HO-Entwicklung entsteht das i-Sulfo-2-oxynaphthalin-3-carbonsäure-4'-chlor-2'-methyl-i'-anilid als körniges Pulver, das abgesaugt, in Soda gelöst, filtriert und mit Kochsalz ausgesalzen wird.2. In the boiling mixture of 62.2 g of 2-oxynaphthalene-3-carboxylic acid-4'-chloro-2'-methyl-i'-anilld and 6oo g of carbon tetrachloride is allowed with good stirring is added dropwise 24 9 chlorosulfonic acid. With vigorous HO development, i-sulfo-2-oxynaphthalene-3-carboxylic acid 4'-chloro-2'-methyl-i'-anilide is formed as a granular powder, which is suctioned off, dissolved in soda, filtered and salted out with common salt .
3. Ein Gemisch von 27,7 9 2-Oxynaphthalin-3-carbonsäure-2.'-methyl-i'-anilid und 2oo g Tetrachlorkohlenstoff wird zum Sieden erhitzt und unter Rühren tropfenweise mit 12 g Chlorsulfonsiure versetzt. Das entstandene Produkt wird abgesaugt, in Soda gelöst, filtriert und mit Kochsalz ausgesalzen. Man erhält so das Na-Salz der i - Sulfo-2-oxynaphthalin -3 - carbonsäure-2'-me thyl-i'-anüid. 3. A mixture of 27.7 g of 2-oxynaphthalene-3-carboxylic acid-2'-methyl-i'-anilide and 200 g of carbon tetrachloride is heated to the boil and 12 g of chlorosulfonic acid are added dropwise with stirring. The resulting product is filtered off with suction, dissolved in soda, filtered and salted out with common salt. The Na salt of i - sulfo-2-oxynaphthalene -3 - carboxylic acid 2'-methyl-i'-anuide is obtained in this way.
4. 27,7 g 2-Oxynaphthalin-3-carbonsäure-4'-methyl-i'-anilid werden in 2oo g Tetrachloräthansuspendiertundauf ioobis iio' erhitztund tropfenweise mit 13 9 Chlorsulfonsäuremethylester versetzt. Nach dem Absaugen wird der entstandene Sulfosäureester r:mit verdünnter Sodalösung erwärmt, wobei das i-Sulfo-:z-oxynaphthalin-3-carbonsäure-4'-methyl-i'-anilid als Natriumsalz in Lösung geht. Es wird ausgesalzen, abgesaugt, mit verdünnter Kochsalzlösung gewaschen und getrocknet.4. 27.7 g of 2-oxynaphthalene-3-carboxylic acid-4'-methyl-i'-anilide are suspended in 2oo g of tetrachloroethane and heated to 100% and 13 g of methyl chlorosulfonate are added dropwise. After suctioning off, the sulfonic acid ester formed is heated with dilute soda solution, the i-sulfo-: z-oxynaphthalene-3-carboxylic acid 4'-methyl-i'-anilide going into solution as the sodium salt. It is salted out, filtered off with suction, washed with dilute sodium chloride solution and dried.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF59930D DE482944C (en) | 1925-10-01 | 1925-10-01 | Process for the preparation of uniform 1-monosulfonic acids of the 2-oxynaphthalene-3-carboxylic acid arylides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF59930D DE482944C (en) | 1925-10-01 | 1925-10-01 | Process for the preparation of uniform 1-monosulfonic acids of the 2-oxynaphthalene-3-carboxylic acid arylides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE482944C true DE482944C (en) | 1929-09-23 |
Family
ID=7108939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF59930D Expired DE482944C (en) | 1925-10-01 | 1925-10-01 | Process for the preparation of uniform 1-monosulfonic acids of the 2-oxynaphthalene-3-carboxylic acid arylides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE482944C (en) |
-
1925
- 1925-10-01 DE DEF59930D patent/DE482944C/en not_active Expired
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