DE65236C - Process for the preparation of two p-amidophenol disulfonic acids - Google Patents
Process for the preparation of two p-amidophenol disulfonic acidsInfo
- Publication number
- DE65236C DE65236C DENDAT65236D DE65236DA DE65236C DE 65236 C DE65236 C DE 65236C DE NDAT65236 D DENDAT65236 D DE NDAT65236D DE 65236D A DE65236D A DE 65236DA DE 65236 C DE65236 C DE 65236C
- Authority
- DE
- Germany
- Prior art keywords
- amidophenol
- acid
- solution
- hydrochloric acid
- preparation
- 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 18
- 150000007513 acids Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 7
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 7
- 159000000000 sodium salts Chemical class 0.000 claims description 7
- 230000002378 acidificating Effects 0.000 claims description 5
- 229940001607 sodium bisulfite Drugs 0.000 claims description 5
- XKSMZERMIZKQLH-UHFFFAOYSA-N N,N-dimethyl-2-nitrosoaniline;hydrochloride Chemical compound Cl.CN(C)C1=CC=CC=C1N=O XKSMZERMIZKQLH-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000001376 precipitating Effects 0.000 claims 1
- 235000002639 sodium chloride Nutrition 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- LGDPTPLJZGPOJL-UHFFFAOYSA-N N,N-dimethyl-2-nitrosoaniline Chemical compound CN(C)C1=CC=CC=C1N=O LGDPTPLJZGPOJL-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 2
- 241000015157 Attalea maripa Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- -1 oxyazobenzenetrisulfonic acid Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 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
-
- 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
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/46—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Wird salzsaures Nitrosodimethylanilin mit einer Lösung von Natriumbisulfit zusammengebracht , so bildet sich. zuerst die von A. W. Forsberg (Ber. XX, 107. Ref.) beschriebene Verbindung, ein amorpher, in Wasser unlöslicher Körper. Noch nicht bekannt ist es aber, dafs dieser durch weitere Einwirkung von Bisulfit in Lösung geht, unter Bildung eines in Wasser leicht löslichen Condensationsproductes von 1 Molecül Nitrosodimethylanilin mit 2 Molecülen Natriumbisulfit der Formel (C H3), N— C6 H, N= (S O3 NaJ2. If hydrochloric acid nitrosodimethylaniline is brought into contact with a solution of sodium bisulfite, it is formed. first the compound described by AW Forsberg (Ber. XX, 107. Ref.), an amorphous body insoluble in water. It is not yet known, however, that this dissolves through further action of bisulphite, with the formation of a condensation product, which is easily soluble in water, of 1 mol of nitrosodimethylaniline with 2 mol of sodium bisulphite of the formula (CH 3 ), N - C 6 H, N = ( SO 3 NaJ 2 .
In letzterer Verbindung können die noch am Stickstoff befindlichen Sulfogruppen unter gewissen Bedingungen mit Leichtigkeit gegen Austausch für Wasserstoff in den Benzolkern wandern, wobei zugleich eine Abspaltung von Dimethylamin stattfindet, während als Endproducte zwei isomere Disulfosäuren des p-Amidophenols resultiren, die durch die Buchstaben α und β unterschieden werden.In the latter compound, the sulfo groups still on the nitrogen can under under certain conditions with ease in exchange for hydrogen in the benzene nucleus migrate, at the same time an elimination of dimethylamine takes place, while as end products two isomeric disulfonic acids of p-amidophenol result, denoted by the letters A distinction can be made between α and β.
Beispiele:
Darstellung der a-p-Amidophenoldisulfosäure.Examples:
Representation of ap-amidophenol disulfonic acid.
5 kg salzsaures Nitrosodimethylanilin werden unter Rühren in 15 kg Natriumbisulfitlösung von 380B. eingetragen. Unter Temperaturerhöhung der Mischung bis 550C. geht ersteres rasch in Lösung. Diese wird von wenig Harz abfiltrirt, das Filtrat mit 23 kg concentrirter Salzsäure versetzt und durch Einleiten von directem Dampf zwei Stunden lang zum Kochen erhitzt. Dann läfst man erkalten, worauf die a-p-Amidophenoldisulfosäure als saures Natronsalz in Form langer, seideglänzender , verfilzter Nadeln auskrystallisirt, welche durch Pressen von der sauren, dimethylaminhaltigen Mutterlauge befreit werden.5 kg muriate nitrosodimethylaniline are introduced with stirring in 15 kg of sodium bisulfite solution of 38 0 B.. When the temperature of the mixture is increased to 55 ° C., the former quickly dissolves. This is filtered off from a little resin, the filtrate is mixed with 23 kg of concentrated hydrochloric acid, and heated to the boil for two hours by the introduction of direct steam. It is then allowed to cool, whereupon the ap-amidophenol disulfonic acid crystallizes out as acid sodium salt in the form of long, shiny, matted needles, which are freed from the acidic mother liquor containing dimethylamine by pressing.
Darstellung der ß-p-Amidophenoldisulfosäure.Representation of ß-p-amidophenol disulfonic acid.
Eine von der obigen ganz verschiedene p-Amidophenoldisulfosäure entsteht, wenn man die Lösung des Nitrosodimethylanilins in Natriumbisulfit für sich so lange zum Kochen erhitzt und eindampft, bis die Temperatur derselben auf 115 bis i2o° C. gestiegen ist, dann erkalten läfst,· mit etwas Wasser und circa dem gleichen Volumen concentrirter Salzsäure versetzt und den nach Verlauf einiger Stunden gebildeten dichten Niederschlag des saurenNatronsalzes der ß-p-Amidophenoldisulfosäure abfiltrirt und aus kochendem Wasser umkrystallisirt. Dasselbe krystallisirt, im Gegensatz zu den langen Nadeln der α-Verbindung, in kleinen kurzen Prismen.A completely different from the above p-amidophenol disulfonic acid is formed if one the solution of the nitrosodimethylaniline in sodium bisulphite so long for itself to boil heated and evaporated until the temperature of the same has risen to 115 to 120 ° C., then cool with a little water and about the same volume of concentrated hydrochloric acid added and the dense precipitate of the acidic sodium salt formed after a few hours the β-p-amidophenol disulfonic acid is filtered off and recrystallized from boiling water. In contrast to the long needles of the α-connection, it crystallizes in small short prisms.
Beide Disulfosäuren zeigen in verdünnter alkalischer Lösung eine prachtvoll blaue Fluorescenz. Both disulfonic acids show a splendid blue fluorescence in a dilute alkaline solution.
An Stelle von Natriumbisulfit können in vorstehenden Beispielen auch andere saure Salze der schwefligen Säure verwendet werden.Instead of sodium bisulfite, other acidic ones can also be used in the above examples Salts of sulphurous acid can be used.
Vergleichende Zusammenstellung der Eigenschaften und Reactionen der erhaltenen p-Amido-Comparative compilation of the properties and reactions of the p-amido-
phenoldisulfosäuren.phenol disulfonic acids.
α - ρ - Amidophenöldisulfosäure erhält man durch Zerlegung ihres Bleisalzes vermittelst Schwefelwasserstoff als eine in Wasser äufserst leicht lösliche, strahlig krystallinische Masse.α - ρ - amidophenöldisulfonic acid is obtained by breaking down its lead salt Hydrogen sulphide as a radiant crystalline mass which is extremely easily soluble in water.
Eine nicht zu verdünnte wässerige Lösung mit Kochsalz versetzt, erstarrt zu einem Brei seideglänzender Nadeln ihres sauren Natronsalzes. A not too dilute aqueous solution mixed with table salt solidifies to a paste silky needles of their acid sodium salt.
Giebt mit Bleizuckerlösung sofortige Fällung eines schweren krystallinischen, in Wasser und Essigsäure unlöslichen Bleisalzes.With lead sugar solution gives immediate precipitation of a heavy crystalline, in water and Acetic acid insoluble lead salt.
Giebt, wie ihre Salze, in wässeriger Lösung mit Eisenchlorid eine rothviolette, bald mifsfarbig werdende Färbung.Gives, like its salts, in aqueous solution with ferric chloride a reddish-violet, soon mif colored nascent coloring.
Ihre Diazoverbindung fällt noch aus ziemlich verdünnter Lösung auf Zusatz von Kochsalz als Natronsalz in Form gelber verfilzter Nadeln aus.Your diazo compound still falls from a fairly dilute solution on the addition of table salt as a sodium salt in the form of yellow matted needles.
β -ρ- Amidophenöldisulfosäure, aus ihrem basischen Bleisalz in gleicher Weise wie die α-Säure abgeschieden, krystallisirt in Nadeln oder Prismen, die sich leicht in warmem, schwieriger in kaltem Wasser lösen. β -ρ- Amidophenöldisulfonic acid, deposited from its basic lead salt in the same way as the α-acid, crystallizes in needles or prisms, which dissolve easily in warm water, more difficultly in cold water.
Ihre mit Kochsalz versetzte Lösung scheidet nur allmälig das saure Natronsalz in kurzen dünnen Prismen ab.Your solution mixed with common salt only gradually separates the acidic sodium salt in brief thin prisms.
Giebt mit Bleizucker keine Fällung, dagegen mit ammoniakalischer Bleizuckerlösung einen amorphen weifsen Niederschlag eines in Essigsäure leicht löslichen basischen Bleisalzes.There is no precipitation with lead sugar, but one with ammoniacal lead sugar solution amorphous white precipitate of a basic lead salt which is easily soluble in acetic acid.
Giebt mit Eisenchlorid eine violettschwarze unbeständige Färbung.Gives a violet-black, inconsistent coloration with ferric chloride.
Ihre Diazoverbindung läfst sich auch aus concentrirter Lösung nicht aussalzen.Their diazo compound cannot be salted out even from concentrated solution.
Die a-p-Amidophenoldisulfosäure scheint mit der von WiIsing aus Oxyazobenzoltrisulfosäure erhaltenen p-Amidophenoldisulfosäure (Ann. 215, S. 237) identisch zu sein, da sie in allen Reactionen mit jener übereinstimmt.The a-p-amidophenol disulfonic acid appears with the p-amidophenol disulfonic acid obtained by WiIsing from oxyazobenzenetrisulfonic acid (Ann. 215, P. 237) to be identical, since it agrees with the former in all reactions.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE65236C true DE65236C (en) |
Family
ID=339046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT65236D Expired - Lifetime DE65236C (en) | Process for the preparation of two p-amidophenol disulfonic acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE65236C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE956127C (en) * | 1953-10-05 | 1957-01-17 | Cfmc | Process for the preparation of 4-amino-diarylamine-N-sulfonic acids |
-
0
- DE DENDAT65236D patent/DE65236C/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE956127C (en) * | 1953-10-05 | 1957-01-17 | Cfmc | Process for the preparation of 4-amino-diarylamine-N-sulfonic acids |
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