DE583055C - Process for the preparation of bis (halooxyaryl) sulfides - Google Patents

Process for the preparation of bis (halooxyaryl) sulfides

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Publication number
DE583055C
DE583055C DEI43463D DEI0043463D DE583055C DE 583055 C DE583055 C DE 583055C DE I43463 D DEI43463 D DE I43463D DE I0043463 D DEI0043463 D DE I0043463D DE 583055 C DE583055 C DE 583055C
Authority
DE
Germany
Prior art keywords
bis
sulfides
halooxyaryl
preparation
chloride
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
DEI43463D
Other languages
German (de)
Inventor
Dr Friedrich Muth
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI43463D priority Critical patent/DE583055C/en
Application granted granted Critical
Publication of DE583055C publication Critical patent/DE583055C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Catalysts (AREA)
  • Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)

Description

Verfahren zur Darstellung von Bis-(halogenoxyaryl)-sulfiden Es ist bekannt, Bis-(halogenoxyaryl)-sulfide durch Kondensation von p-Monohalogenphenolen mit Schwefelchloriden herzustellen. Beim Einwirken von Schwefelchlorid auf Trichlorphenol entstehen jedoch nur harzartige Produkte. Ebenso lassen sich Dihalogenphenole mit .Schwefelchloriden nicht ohne weiteres zu Bis-(halogenoxyaryl)-sulfiden kondensieren.Process for the preparation of bis (halooxyaryl) sulfides It is known bis (halogenoxyaryl) sulfides by condensation of p-monohalophenols with sulfur chlorides. When sulfur chloride acts on trichlorophenol however, only resin-like products are created. Dihalophenols can also be used .Sulfur chlorides do not readily condense to bis (halooxyaryl) sulfides.

Es wurde nun gefunden, daß man die beim Einwirken von Schwefelchloriden auf Di-oder Trihalogenphenole bestehenden Schwierigkeiten überwinden kann, wenn man die. Kondensation in Gegenwart von Aluminiumchlorid durchführt. Beispiel i 82 g 2, 4-Dichlorphenol werden in 250 ccm Schwefelkohlenstoff oder Tetrachlorkohlenstoff gelöst, 5o g fein pulverisiertes Aluminiumchlorid eingetragen und 22 g Schwefelchlorid eingetropft. Es entwickelt sich reichlich Chlorwasserstoff. Nach etwa 12stündigem Stehen zersetzt man mit Eis, gibt noch konzentrierte Salzsäure zu und treibt mit Wasserdampf das Lösungsmittel und etwas unverändertes Chlorphenol ab. Der Rückstand wird abgesaugt und mit Wasser ausgewaschen. Das neue Bis-(dichloroxyphenyl)-sulfid kristallisiert aus Toluol oder verdünntem Alkohol in farblosen Nadeln vom F. z88°.It has now been found that you can overcome the existing difficulties in the action of sulfur chlorides on di- or trihalophenols if you use the. Carries out condensation in the presence of aluminum chloride. Example i 82 g of 2,4-dichlorophenol are dissolved in 250 cc of carbon disulfide or carbon tetrachloride, 50 g of finely powdered aluminum chloride are added and 22 g of sulfur chloride are added dropwise. Plenty of hydrogen chloride develops. After standing for about 12 hours, it is decomposed with ice, concentrated hydrochloric acid is added and the solvent and some unchanged chlorophenol are driven off with steam. The residue is filtered off with suction and washed out with water. The new bis (dichloroxyphenyl) sulfide crystallizes from toluene or dilute alcohol in colorless needles with a temperature of z88 °.

In entsprechender Weise entsteht aus 2, 5-Dichlorphenol ein Bis-(dichloroxyphenyl)-sulfid vom F. t77°, aus 2, 6-Dichlorphenol vom F. i4o° und aus 2, 4, 6-Trichlorphenot,vom F. 285°. Beispiel e 126 g 2, 4-Dibromphenol werden in 6oo ccm Schwefelkohlenstoff gelöst und 5o g fein gepulvertes Aluminiumchlorid eingetragen. In die entstandene klare Lösung werden unter Eiskühlung und Rühren langsam 22 g Schwefelchlorid eingetropft, und es wird, wie in Beispiel i angegeben, aufgearbeitet.In a corresponding manner, 5-dichlorophenol formed from 2, a bis (dichloroxyphenyl) sulfide, melting at t77 °, from 2, 6-dichlorophenol, melting i4o ° and 2, 4, 6-Trichlorphenot, mp 285 ° . Example e 1 26 g of 2,4-dibromophenol are dissolved in 600 cc of carbon disulfide and 50 g of finely powdered aluminum chloride are added. 22 g of sulfur chloride are slowly added dropwise to the resulting clear solution, while cooling with ice and stirring, and it is worked up as indicated in Example i.

Das neue Bis-(dibromoxyphenyl)-sulfid kristallisiert aus Toluol in farblosen glänzenden Nadeln vom F. 2i2°. Beispici3 82 g 2, 4-Dichlorphenol werden in 25o ccm Schwefelkohlenstoff gelöst, dann bei 2o bis 22° ioo g fein gepulvertes Aluminiumchlorid eingetragen und 35 g Schwefelchlorür eingetropft. Nach 8stündigem Rühren gibt man auf Eis und bläst das Lösungsmittel ab. Der Rückstand wird durch Lösen in verdünnter Natronlauge und Fällen mit Salzsäure gereinigt.The new bis (dibromoxyphenyl) sulfide crystallizes from toluene in colorless shiny needles of F. 2i2 °. Beispici3 82 g of 2,4-dichlorophenol Dissolved in 25o ccm carbon disulfide, then at 20 to 22 ° 100 g finely powdered Entered aluminum chloride and added dropwise 35 g of sulfuric chloride. After 8 hours Stirring is added to ice and the solvent is blown off. Of the Residue is cleaned by dissolving in dilute sodium hydroxide solution and precipitating with hydrochloric acid.

Aus Toluol oder Eisessig umkristallisiert schmilzt das Kondensationsprodukt bei z85°. Der Mischschmelzpunkt mit dem nach Beispiel i erhaltenen zeigt keine Depression.Recrystallized from toluene or glacial acetic acid, the condensation product melts at z85 °. The mixed melting point with that obtained according to Example i shows no depression.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Bis-(halogenoxyaryl)-sulfiden, dadurch gekennzeichnet, daB man Di- oder Trihalogenphenole und ein Schwefelchlorid in Gegenwart von Aluminiumchlorid kondensiert.PATENT CLAIM: Process for the preparation of bis (halogenoxyaryl) sulfides, characterized in that one is di- or trihalophenols and a sulfur chloride condensed in the presence of aluminum chloride.
DEI43463D 1932-01-13 1932-01-13 Process for the preparation of bis (halooxyaryl) sulfides Expired DE583055C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI43463D DE583055C (en) 1932-01-13 1932-01-13 Process for the preparation of bis (halooxyaryl) sulfides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI43463D DE583055C (en) 1932-01-13 1932-01-13 Process for the preparation of bis (halooxyaryl) sulfides

Publications (1)

Publication Number Publication Date
DE583055C true DE583055C (en) 1933-08-28

Family

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Family Applications (1)

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DEI43463D Expired DE583055C (en) 1932-01-13 1932-01-13 Process for the preparation of bis (halooxyaryl) sulfides

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1024089B (en) * 1955-05-18 1958-02-13 Bayer Ag Process for the production of sulfides of multiply halogenated phenols
US2849494A (en) * 1956-05-17 1958-08-26 Monsanto Chemicals 2, 2'-thiobis
US2868841A (en) * 1956-05-31 1959-01-13 Monsanto Chemicals Purifying 2, 2'-thiobis(polyhalophenols)
US2937208A (en) * 1955-05-18 1960-05-17 Bayer Ag Metasulfides of polyhalogenated phenols

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1024089B (en) * 1955-05-18 1958-02-13 Bayer Ag Process for the production of sulfides of multiply halogenated phenols
US2937208A (en) * 1955-05-18 1960-05-17 Bayer Ag Metasulfides of polyhalogenated phenols
US2849494A (en) * 1956-05-17 1958-08-26 Monsanto Chemicals 2, 2'-thiobis
US2868841A (en) * 1956-05-31 1959-01-13 Monsanto Chemicals Purifying 2, 2'-thiobis(polyhalophenols)

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