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DE365169C - Process for the preparation of organic sulfur compounds - Google Patents

Process for the preparation of organic sulfur compounds

Info

Publication number
DE365169C
DE365169C DEF45226D DEF0045226D DE365169C DE 365169 C DE365169 C DE 365169C DE F45226 D DEF45226 D DE F45226D DE F0045226 D DEF0045226 D DE F0045226D DE 365169 C DE365169 C DE 365169C
Authority
DE
Germany
Prior art keywords
preparation
sulfur compounds
organic sulfur
weight
parts
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
Application number
DEF45226D
Other languages
German (de)
Inventor
Dr Rudolf Berendes
Dr Hans Hahl
Dr Hermann Weyland
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Farbenfabriken Vorm Friedr Bayer and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Farbenfabriken Vorm Friedr Bayer and Co filed Critical Farbenfabriken Vorm Friedr Bayer and Co
Priority to DEF45226D priority Critical patent/DE365169C/en
Application granted granted Critical
Publication of DE365169C publication Critical patent/DE365169C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
    • C07G99/00—Subject matter not provided for in other groups of this subclass
    • C07G99/002—Compounds of unknown constitution containing sulfur
    • C07G99/0022—Compounds of unknown constitution containing sulfur derived from hydrocarbons

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Working-Up Tar And Pitch (AREA)

Description

Verfahren zur Darstellung organischer Schwefelverbindungen. Friedel & Crafts häben (Ann. de chim. et phys. Ser. 6, Bd. 1q., S. 437 [1888]) durch Einwirkung von Schwefel und großen Mengen Aluminiumchlorid auf Benzol ein Gemenge von Thiophenol, Diphenylsulfid und Diphenylendisulfid erhalten. Diese Methode zur Darstellung von Arylmerkaptanen auf die Homologen des Benzols :angewandt, gab jedoch wegen der vielerlei entstehenden Nebenprodukte kein Resultat (Patentschrift 296986, K1. 12q, S. i, Zeile 53 bis 55), und zwar offenbar deshalb, weil die großen dabei verwendeten Mengen Aluminiumchlorn.dinfolge ihrer auf-und abbauenden Wirkung die Reaktion ungünstig beeinflußten. Über die Natur der Nebenprodukte wird in dieser Patentschrift nichts angegeben.Process for the preparation of organic sulfur compounds. Friedel & Crafts had (Ann. De chim. Et phys. Ser. 6, Vol. 1q., P. 437 [1888]) The effect of sulfur and large amounts of aluminum chloride on benzene is a mixture obtained from thiophenol, diphenyl sulfide and diphenylene disulfide. This method for Representation of aryl mercaptans on the homologues of benzene: applied, but gave no result due to the many by-products formed (patent specification 296986, K1. 12q, p. I, lines 53 to 55), apparently because the big ones are there Amounts of aluminum chlorine used due to their building up and degrading effect Adversely affected the reaction. The nature of the by-products is discussed in this Patent specification not specified.

Es wurde nun gefunden, daß man durch Einwirkwng von geringen .Mengen Aluminiumchlorid und Schwefel auf Toluol in der Wärme neben einer kleinen Menge isomerer Thiokresole und etwas asphaltartigem Rückstand im, wesentlichen ein dickflüssiges Öl erhält, das zwischen 16o bis 2q.0° (1o mm) siedet. Zweckmäßig verwendet man nicht mehr als 15 Prozent an Al C13, um einen möglichst hohen Gehalt an hochsiedendem Öl zu erzielen. Man führt die Reaktion zweckmäßig in der Weise aus, daß man z. B. Zoo Gewichts= teile Toluol mit etwa 25 bis 35 Gewichtsteilen Schwefel und 7 bis 1o Gewichtsteilen Aluminiumchlorid langsam erwärmt und so lange im Sieden (12o bis 13o°) erhält, bis die Entwicklung von Salzsäure und Schwefelwasserstoff beendet ist. Das auf diese Weise erhaltene Öl zeigt neben Reizlosigkeit und Geruchlosigkeit eine ganz hervorragende Wirkung gegen Skabies. Statt Toluol kann man mit demselben Erfolg Xylol verwenden. Beispiel s. 1 ooo Gewichtsteile Toluol, 33o Gewichtsteile Schwefel und 8o Gewichtsteile Alumliniumchlorid werden langsam am Rückflußkühler -im Ölbade erhitzt und im, Sieden erhalten, .bis die 'Entwicklung von Schwefelwasserstoff und Salzsäure beendet ist. Die Mischung wird durch Eingießen in Wasser vom überschüssigen Aluminiumchlorid befreit,und nach der Entwässerung irn Vakuum fraktioniert. Man erhält nach dem Übergehen des überschüssigen Toluols bei 3 mm Druck etwa 5oo Gewichtsteile eines zwischen i5o° und 23o° siedenden gelben Öles, dem sein unangenehmer Geruch durch Schütteln mit Lauge entzogen wird. Das gereinigte t51 enthält 23 bis 25 Prozent Schwefel. Es ist gegen Säuren und Laugen unempfindlich Lund ergibt mit Oxydationsmitteln, wie Wasserstoffsuperoxyd, keine Schwefelsäure. Rauchende Sal- petersäure zerstört es nur sehr schwer. Bei der Destillation des Rohöles hinterbleiben geringe Mengen einer asphaltartigen, in der Kälte spröden, schwarzen Masse.It has now been found that by the action of small amounts of aluminum chloride and sulfur on toluene in the heat, in addition to a small amount of isomeric thiocresols and some asphalt-like residue, essentially a viscous oil is obtained which is between 160 to 2q.0 ° (10 mm ) boils. It is advisable not to use more than 15 percent of Al C13 in order to achieve the highest possible high-boiling oil content. The reaction is expediently carried out in such a way that one z. B. Zoo weight = parts toluene with about 25 to 35 parts by weight of sulfur and 7 to 1o parts by weight of aluminum chloride slowly heated and kept boiling (12o to 13o °) until the development of hydrochloric acid and hydrogen sulfide is complete. The oil obtained in this way shows, in addition to lack of irritation and odor, a very excellent effect against scabies. Instead of toluene, one can use xylene with the same success. Example see 100 parts by weight of toluene, 33o parts by weight of sulfur and 80 parts by weight of aluminum chloride are slowly heated in a reflux condenser in an oil bath and kept in the boil until the evolution of hydrogen sulfide and hydrochloric acid has ended. The mixture is freed from excess aluminum chloride by pouring it into water and, after dehydration, fractionated in a vacuum. After the excess toluene has passed over at 3 mm pressure, about 500 parts by weight of a yellow oil boiling between 150 ° and 230 ° are obtained, from which its unpleasant odor is removed by shaking with lye. The purified t51 contains 23 to 25 percent sulfur. It is insensitive to acids and alkalis. Lund does not produce sulfuric acid with oxidizing agents such as hydrogen peroxide. Fuming nitric acid destroys it very difficult. When the crude oil is distilled, small amounts of an asphalt-like black mass that is brittle in the cold are left behind.

Beispiel 2.Example 2.

75 Gewichtsteile Xylol, 25 Gewichtsteile Schwefel und 6 Gewichtsteile Aluminiumchlorid werden wie in Beispiel i erhitzt. Nach Beendigung der Reaktion wird in Wasser eingegossen und die Xylollösung fraktioniert destilliert. Bei 3 bis 5 mm Druck wird der zwischen i5o und 23o° übergehende Anteil aufgefangen. Es ist ein dunkelgelbes Öl, welches sich von dem aus Toluol gewonnenen Produkt hauptsächlich durch seine erheblich --rößere Viskosität unterscheidet.75 parts by weight of xylene, 25 parts by weight of sulfur and 6 parts by weight Aluminum chloride are heated as in Example i. After the reaction has ended is poured into water and the xylene solution is fractionally distilled. At 3 to 5 mm of pressure, the portion passing between 15o and 23o ° is absorbed. It is a dark yellow oil, which is mainly different from the product obtained from toluene differs due to its considerably higher viscosity.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung organischer Schwefelverbindungen, darin bestehend, daB man Benzolhomologe, wie Toluol oder Xylol, mit Schwefel bei Gegenwart geringer Mengen von Aluminiumchlorid erhitzt. PATENT CLAIM: Process for the preparation of organic sulfur compounds, consisting in heating benzene homologues such as toluene or xylene with sulfur in the presence of small amounts of aluminum chloride.
DEF45226D 1919-09-04 1919-09-04 Process for the preparation of organic sulfur compounds Expired DE365169C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF45226D DE365169C (en) 1919-09-04 1919-09-04 Process for the preparation of organic sulfur compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF45226D DE365169C (en) 1919-09-04 1919-09-04 Process for the preparation of organic sulfur compounds

Publications (1)

Publication Number Publication Date
DE365169C true DE365169C (en) 1922-12-08

Family

ID=7100396

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF45226D Expired DE365169C (en) 1919-09-04 1919-09-04 Process for the preparation of organic sulfur compounds

Country Status (1)

Country Link
DE (1) DE365169C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2817685A (en) * 1954-11-04 1957-12-24 Geigy Ag J R Process for the production of organic sulphur compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2817685A (en) * 1954-11-04 1957-12-24 Geigy Ag J R Process for the production of organic sulphur compounds

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