DE260562C - - Google Patents
Info
- Publication number
- DE260562C DE260562C DENDAT260562D DE260562DA DE260562C DE 260562 C DE260562 C DE 260562C DE NDAT260562 D DENDAT260562 D DE NDAT260562D DE 260562D A DE260562D A DE 260562DA DE 260562 C DE260562 C DE 260562C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- acid
- dichloroanthracene
- monosulfonic
- mesodichloranthracene
- 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.)
- Active
Links
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- MGDFBMDVXFZGSJ-UHFFFAOYSA-N 1,2-dichloroanthracene Chemical compound C1=CC=CC2=CC3=C(Cl)C(Cl)=CC=C3C=C21 MGDFBMDVXFZGSJ-UHFFFAOYSA-N 0.000 description 2
- XENVCRGQTABGKY-ZHACJKMWSA-N Chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 2
- ISQCHBWNUCJSFR-UHFFFAOYSA-N ClC=1C(=C(C2=CC3=CC=CC=C3C=C2C=1)S(=O)(=O)O)Cl Chemical class ClC=1C(=C(C2=CC3=CC=CC=C3C=C2C=1)S(=O)(=O)O)Cl ISQCHBWNUCJSFR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- -1 sulfo- Chemical class 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 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
- C07C309/33—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
- C07C309/38—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 at least three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Die übliche Sulfierung des Mesodichloranthracens mittels Oleums liefert bekanntlich zwei isomere Dichloranthracensulfosäuren, so daß die Darstellung der praktisch wichtigen Mesodichloranthracen-ß-monosulfosäure für sich allein bisher nicht gelungen ist.The usual sulphonation of mesodichloranthracene using oleum is known to provide two isomeric dichloroanthracene sulfonic acids, see above that the representation of the practically important mesodichloranthracene-ß-monosulfonic acid for itself alone has not yet succeeded.
Es hat sich nun gezeigt, daß sich das Mesodichloranthracen leicht und in äußerst glatter Weise in die Mesodichloranthracen-ß-monosulfosäure überführen läßt, wenn man die Sulfierung mittels der erforderlichen Menge Schwefelsäurechlorhydrin vornimmt, zweckmäßig bei Anwesenheit eines indifferenten Verdünnungs- bzw. Lösungsmittels.It has now been shown that mesodichloroanthracene is easy and extremely smooth Way can be converted into the mesodichloranthracene-ß-monosulfonic acid if the Carries out sulfonation using the required amount of sulfuric acid chlorohydrin, expedient in the presence of an inert diluent or solvent.
Ein gleiches gilt für die Darstellung anderer Mesohalogenanthracen-ß-monosulfosäuren.The same applies to the representation of other mesohalogenanthracene-ß-monosulfonic acids.
100 Teile Dichloranthracen werden in 1000 Teilen reinem Chloroform suspendiert und auf 300C. angewärmt. Hierzu läßt man 50 Teile Chlorsulfonsäure langsam zulaufen. Nach 4 stündigem Rühren bei 40° läßt man erkalten, saugt den Rückstand ab und trocknet. Die so dargestellte Dichloranthracenmonosulfosaure besteht fast ausschließlich aus der ß-Verbindung; sie bildet ein gelbes, in Wasser ziemlich leicht lösliches Pulver; die wäßrige Lösung zeigt eine schöne blaue Fluoreszenz. Analog verfährt man bei Verwendung anderer indifferenter Mittel oder anderer Mesohalogenanthracene. 100 parts dichloroanthracene are suspended in 1000 parts of pure chloroform and warmed to 30 0 C.. To this end, 50 parts of chlorosulfonic acid are slowly run in. After stirring for 4 hours at 40 °, the mixture is allowed to cool, the residue is filtered off with suction and dried. The dichloroanthracene monosulfonic acid thus represented consists almost exclusively of the ß-compound; it forms a yellow powder which is fairly easily soluble in water; the aqueous solution shows a beautiful blue fluorescence. The procedure is analogous when using other indifferent agents or other mesohalogenanthracenes.
100 Teile Dibromanthracen werden in 1000 Teilen Chloroform suspendiert auf 40 ° erwärmt. Alsdann läßt man 60 Teile Chlorsulfonsäure hinzulaufen und hält die Reaktionsmasse bis zu beendeter Salzsäureentwicklung bei dieser Temperatur. Das kristallinisch abgeschiedene Reaktionsprodukt wird abgesaugt und getrocknet. Es zeigt ähnliche Eigenschaften wie die Mesodichloranthracensulfo-100 parts of dibromanthracene are used in 1000 Parts of chloroform suspended heated to 40 °. 60 parts of chlorosulfonic acid are then left run in and keep the reaction mass at this temperature until the evolution of hydrochloric acid has ended. The crystalline deposited The reaction product is filtered off with suction and dried. It shows similar properties like the mesodichloranthracene sulfo-
saure.acid.
Beispiel III.Example III.
4545
100 Teile Dichloranthracen werden in ein Gemenge von 300 Teilen Monohydrat und 50 Teilen Chlorsulfonsäure innerhalb 1Z4 Stunde eingetragen. Nach 3 stündigem Rühren bei 300 ist die Sulfierung beendet. Die grün gefärbte Schmelze wird in 5000 Teile Wasser gegossen, aufgekocht, mittels 60 Teilen Kochsalz ausgesalzen und nach dem Erkalten das ausgeschiedene dichloranthracenmonosulfosaure Natrium abfiltriert.100 parts of dichloroanthracene are added to a mixture of 300 parts of monohydrate and 50 parts of chlorosulfonic acid over a period of 1 Z 4 hours. After 3 hours of stirring at 30 0 sulfonation is completed. The green colored melt is poured into 5000 parts of water, boiled, salted out using 60 parts of common salt and, after cooling, the precipitated sodium dichloroanthracene monosulfonic acid is filtered off.
Paten τ-Anspruch:Sponsorship τ claim:
Verfahren zur Darstellung von Mesohalogenanthracen-ß-monosulfosäure, darin bestehend, daß man Mesohalogenanthracen mit Schwefelsäurechlorhydrin behandelt.Process for the preparation of mesohalogenanthracene-ß-monosulfonic acid, consisting in treating mesohalanthracene with sulfuric acid chlorohydrin.
BERLIN. GEDRUCKT IN DER REICHSDRUCKEREI.BERLIN. PRINTED IN THE REICHSDRUCKEREI.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE260562C true DE260562C (en) |
Family
ID=518195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT260562D Active DE260562C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE260562C (en) |
-
0
- DE DENDAT260562D patent/DE260562C/de active Active
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