DE52827C - Process for the preparation of sulphurized oxydiphenylamine - Google Patents
Process for the preparation of sulphurized oxydiphenylamineInfo
- Publication number
- DE52827C DE52827C DENDAT52827D DE52827DA DE52827C DE 52827 C DE52827 C DE 52827C DE NDAT52827 D DENDAT52827 D DE NDAT52827D DE 52827D A DE52827D A DE 52827DA DE 52827 C DE52827 C DE 52827C
- Authority
- DE
- Germany
- Prior art keywords
- oxydiphenylamine
- sulfur
- alkali
- preparation
- thiooxydiphenylamine
- 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
- 238000000034 method Methods 0.000 title claims 3
- 238000002360 preparation method Methods 0.000 title claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- -1 alkalis Substances 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229960000583 Acetic Acid Drugs 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008043 acidic salts Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/36—Seven-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Nach Beobachtung des Erfinders läfst sich das m - Oxydiphenylamin (Calm, Ber. XVI, 2786) durch Erwärmen seiner Salze mit Schwefel in Thiosubstitutionsproducte überführen. After observing the inventor, it can be done the m - oxydiphenylamine (Calm, Ber. XVI, 2786) by heating its salts with Convert sulfur into thio substitution products.
Es ist hierbei nicht erforderlich, die trockenen Salze mit Schwefel zu erhitzen, sondern es genügt, in die heifsen Lösungen der Alkalisalze des Oxydiphenylamins Schwefel einzutragen und längere Zeit zu kochen. Sehr vortheilhaft zur Beendigung der Reaction ist es, Alkali in gröfserer Menge anzuwenden, als zur Salzbildung mit dem Oxydiphenylamin erforderlich ist, indem durch dieses der entstehende Schwefelwasserstorf gebunden und die Reaction beschleunigt wird. Ist überschüssiges Alkali nicht vorhanden, so geht die Reaction unter Schwefelwasserstoffentwickelung vor sich.It is not necessary to heat the dry salts with sulfur, but rather it is sufficient to add sulfur to the hot solutions of the alkali salts of oxydiphenylamine and to cook for a long time. It is very advantageous to terminate the reaction Use more alkali than is necessary for salt formation with the oxydiphenylamine is, in that the hydrogen sulphide formed is bound by this and the reaction is accelerated. If there is no excess alkali, the reaction goes under Development of hydrogen sulfide ahead.
Derselbe Effect wird erzielt, wenn man Polysulfide auf Oxydiphenylamin einwirken läfst bezw. wenn man den Schwefel zunächst durch Kochen mit Alkali in Lösung bringt und alsdann in die heifse alkalische Lösung des Alkalipolysulfids das Oxydiphenylamin einträgt. The same effect is achieved when polysulphides act on oxydiphenylamine runs resp. if the sulfur is first brought into solution by boiling with alkali and then introduces the oxydiphenylamine into the hot alkaline solution of the alkali polysulphide.
Die Abscheidung des Thiooxydiphenylamins kann durch Zusatz von Säuren zu dem Reactionsproduct erfolgen. Es gelingt jedoch, auch durch Zusatz von sauren Salzen, wie Natriumbicarbonat u. s. w. , dasselbe auszufällen. The deposition of the thiooxydiphenylamine can be achieved by adding acids to the reaction product take place. However, it is also possible to precipitate the same by adding acidic salts such as sodium bicarbonate and so on.
Das Thiooxydiphenylamin gehört zu der Klasse ■ der Disulfide.
Formel:The thiooxydiphenylamine belongs to the class ■ of the disulfides.
Formula:
Es kommt ihm dieIt comes to him
OHOH
Der Körper stellt ein hellgelbes, geruch- und geschmackloses, in festen Alkalien leicht, in Ammoniak und Alkalicarbonaten schwieriger lösliches Pulver dar. Alkalisulfide lösen es leicht auf, ebenso Alkohol, Aether, Aceton, Eisessig, Benzol u. s.w. Durch Benzin wird das Thiooxydiphenylamin aus seinen. Lösungen in Kohlenwasserstoffen abgeschieden. Der Schmelzpunkt der Substanz liegt bei ca. 15 50.The body is a pale yellow, odorless and tasteless powder, easily soluble in solid alkalis, more difficult to dissolve in ammonia and alkali carbonates. Alkali sulfides dissolve it easily, as does alcohol, ether, acetone, glacial acetic acid, benzene, etc. The thiooxydiphenylamine is converted from its gasoline. Solutions deposited in hydrocarbons. The melting point of the substance is approx. 15 5 0 .
Beim Uebergiefsen des Thiooxydiphenylamins mit Essigsäureanhydrid unter Zusatz von trockenem Natriumacetat wird dasselbe unter lebhafter Erwärmung acetylirt.When Uebergiefsen the thiooxydiphenylamine with acetic anhydride with the addition of dry sodium acetate is acetylated with vigorous warming.
Die entstehende Acetylverbindung ist schwach gelb gefärbt, in Alkohol, Aether etc. löslich, in Alkalien in der Kälte unlöslich. Beim Erwärmen löst sie sich unter Abspaltung der Acetylgruppe. Diese Substanz schmilzt bei ca. 130 bis 13 30.The resulting acetyl compound is pale yellow in color, soluble in alcohol, ether, etc., and insoluble in alkalis in the cold. When heated, it dissolves, splitting off the acetyl group. This substance melts at approx. 130 to 13 3 0 .
Vorschriften für die Darstellung desRules for the presentation of the
Thiooxydiphenylamins.
Beispiel I. Man löst 370 Theile Oxydiphenylamin (2 Molecule) unter Zusatz vonThiooxydiphenylamine.
Example I. 370 parts of oxydiphenylamine (2 molecules) are dissolved with the addition of
8o Theilen Natriumhydroxyd (2 Molecule) in Wasser. Es bildet sich alsdann unter Absättigung der Hydroxylgruppe das Natronsalz dieses Körpers und geht in Lösung. Trägt man nunmehr in die siedende Lösung successive 96 Theile Schwefel ein und erhält im Sieden, so bildet sich unter Schwefelwasserstoffentwickelung Thiooxydiphenylamin. Die Abscheidung kann durch Säuren oder saure Salze erfolgen.80 parts of sodium hydroxide (2 molecules) in water. It then forms under saturation the hydroxyl group removes the sodium salt of this body and goes into solution. One now carries it successively into the boiling solution 96 parts of sulfur are incorporated and obtained on boiling, it is formed with the evolution of hydrogen sulfide Thiooxydiphenylamine. The separation can be done by acids or acidic salts.
Zur Reinigung krystallisirt man aus Alkohol oder löst in heifsem Benzol und versetzt die erkaltete Lösung mit Benzin.To clean it, crystallize from alcohol or dissolve in hot benzene and add it cooled solution with gasoline.
Beispiel II. Man löst 240 Theile Natriumhydroxyd in Wasser und fügt hierauf 18 5 Theile Oxydiphenylamin hinzu. In die so erhaltene Lösung werden unter Erhitzen successive 200 Theile Schwefel eingetragen und bis zur völligen Lösung desselben erwärmt.Example II. 240 parts of sodium hydroxide are dissolved in water and 18 5 parts are then added Oxydiphenylamine added. In the solution obtained in this way, 200 Part of the sulfur entered and heated until it was completely dissolved.
Durch Zusatz von Natriumbicarbonat zu der heifsen Reactionsmasse fällt das Thioproduct als hellgelbes Pulver aus. Durch Auflösen in kalter Alkalilauge und Ausfällen mit Essigsäure wird es rein erhalten.The thioproduct precipitates by adding sodium bicarbonate to the hot reaction mass as a light yellow powder. By dissolving in cold alkali lye and precipitating with acetic acid it will be kept pure.
Beispiel III. 250 Theile Natriumhydroxyd werden in Wasser gelöst und mit 200 Theilen Schwefel so lange erhitzt, bis sich kein Schwefel mehr löst. Alsdann giefst man von etwa noch ungelöstem Schwefel ab und erhitzt diese Lösung darauf in geschlossenem Digestor mit 145 Theilen Oxydiphenylamin auf 150 bis 2000. Die Verarbeitung des Reactionsproductes geschieht wie in Beispiel I oder II.Example III. 250 parts of sodium hydroxide are dissolved in water and heated with 200 parts of sulfur until no more sulfur dissolves. Then you giefst on as yet undissolved sulfur and this solution is heated to in a closed digester with 145 parts Oxydiphenylamin to 150 to 200 0th The reaction product is processed as in Example I or II.
Das Thiooxydiphenylamin soll vornehmlich als Arzeneimittel dienen. Es kann aber auch zur Herstellung von Azofarbstoffen Verwendung finden.The thiooxydiphenylamine is primarily intended to be used as a medicinal product. But it can also find use for the production of azo dyes.
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE52827C true DE52827C (en) |
Family
ID=327511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT52827D Expired - Lifetime DE52827C (en) | Process for the preparation of sulphurized oxydiphenylamine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE52827C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5281579A (en) * | 1984-03-23 | 1994-01-25 | Baxter International Inc. | Purified virus-free hemoglobin solutions and method for making same |
-
0
- DE DENDAT52827D patent/DE52827C/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5281579A (en) * | 1984-03-23 | 1994-01-25 | Baxter International Inc. | Purified virus-free hemoglobin solutions and method for making same |
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