DE350737C - Process for the production of thionaphthene from coal tar - Google Patents

Process for the production of thionaphthene from coal tar

Info

Publication number
DE350737C
DE350737C DENDAT350737D DE350737DD DE350737C DE 350737 C DE350737 C DE 350737C DE NDAT350737 D DENDAT350737 D DE NDAT350737D DE 350737D D DE350737D D DE 350737DD DE 350737 C DE350737 C DE 350737C
Authority
DE
Germany
Prior art keywords
thionaphthene
sodium
coal tar
production
naphthalene
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
DENDAT350737D
Other languages
German (de)
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.)
Gesellschaft fuer Teerverwertung mbH
Original Assignee
Gesellschaft fuer Teerverwertung mbH
Publication date
Application granted granted Critical
Publication of DE350737C publication Critical patent/DE350737C/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Gewinnung von Thionaphthen aus Steinkohlenteer. Im Verfolg der Untersuchungen über das im Steinkohlenteer entdeckte Thionaphthen wurde gefunden, daß dieses mit Natriumamid eine feste Verbindung eingeht, welche unlöslich in Kohlenwasserstoffen ist, dagegen finit Wasser leicht in Natronlauge und Thionaphthen zerfällt. Diese Verbindung, deren Konstitution bisher nicht aufgeklärt worden ist, die aber, da die Reaktion des Tionaphthens mit dein Amid unter Ammoniakentwicklung erfolgt, als eine Natriumverbindung (res Schwefelkörpers angesehen werden muß, eignet sich nun zu einer überraschend einfachen Abscheidung des Thionaphthens aus dein Naplitlialin des Steinkohlenteers. Wird letzteres mit ausreichenden Mengen Natriumamid bei etwa iq.o bis 1q.5° in Reaktion gebracht, so entweicht Ammoniak, und nach beendeter Einwirkung und Entfernung de-. nicht ang°griffenen Naphthalins hinterbleibt die Natriumverbindung des Thionaphthens als dunkle, amorphe Masse, welche bei der Behandlung mit Wasser in der obenerwähnten Weise zerfällt und die Gewinnung des Thionaphthens in reinem, krystallisiertem Zustand ermöglicht. Das Natriumamid kann hierbei auch durch das in einem Ammoniakstrom zur Einwirkung gelangende Natrium, schwieriger dagegen durch Natrium allein, ersetzt werden, da letzteres bei höherer Temperatur mit großer Heftigkeit und nur unter Abspaltung von Schwefel auf Thionaphthen einwirkt.Process for the production of thionaphthen from coal tar. In pursuit the investigations on the thionaphthene discovered in coal tar were found that this forms a solid bond with sodium amide, which is insoluble in hydrocarbons whereas finite water easily breaks down into caustic soda and thionaphthene. These Connection, the constitution of which has not yet been clarified, but which is there the reaction of Tionaphthens with your amide takes place with evolution of ammonia, as a sodium compound (res sulfur body must be considered, is now suitable to a surprisingly simple separation of the thionaphthene from your naplitlialin of coal tar. The latter is done with sufficient amounts of sodium amide at around iq.o to 1q.5 ° reacted, then ammonia escapes, and after the end of the action and removal de-. If naphthalene is not attacked, the sodium compound remains of thionaphthene as a dark, amorphous mass, which when treated with water disintegrates in the manner mentioned above and the extraction of thionaphthene in pure, crystallized state allows. The sodium amide can also be used by the Sodium acting in a stream of ammonia is more difficult to penetrate Sodium alone, since the latter can be replaced with great violence at higher temperatures and only acts on thionaphthene by splitting off sulfur.

Beispiel. ioo kg gepreßtes und durch Destillation sorgfältig von Wasser befreites Rohnaphthalin «-erden mit 5 bis 7 kg Natriumamid in einem gußeisernen Rührkessel bei einer Teiiiperatur von iq.o bis 1d.5° während 5 Stunden unter gutem Durchrühren zur Reaktion gebracht. Nachdem diese beendet ist, was man schon an dem Nachlassen der Ainnioniakentwicklung feststellen kann, läßt man langsam erkalten und absitzen, entfernt das nicht angegriffene, noch flüssige Naphthalin größtenteils durch Abgießen oder Abhebern und behandelt die zurückbleibende, meist krümelige, am Boden sitzende Thionaphthennatriumverbin dung niit Toluol zwecks Entfernung alles anhaftenden Naphthalins. Zum Schluß bringt man das Thionaphthennatrium auf ein Filter, wäscht nochmals finit Toluol aus und trägt die noch toluolfeuchte Masse in Wasser ein, mit welchem sie unter bedeutender Wärmeentwicklung reagiert. Das abgeschiedene Rohthionaphthen wird durch eine einmalige Destillation von etwas toluolhaltigeni Vorlauf sowie geringen Mengen hochsieden-«ein Rückstand befreit und als kristallisierte Verbindung von einheitlichem Siedepunkt 21g biS 22U' gewonnen.Example. 100 kg of pressed water and carefully distilled off Freed crude naphthalene earth with 5 to 7 kg of sodium amide in a cast iron Stirring kettle at a Teiiiperatur from iq.o to 1d.5 ° for 5 hours under good Stirring brought to reaction. After this is over, what can be done about it If the development of ammonia can be determined, it is allowed to cool slowly and settle down, removes most of the unaffected, still liquid naphthalene by pouring or siphoning off and treats the remaining, mostly crumbly, Sodium thionaphthene compound sitting on the floor with toluene for the purpose of removing everything adhering naphthalene. Finally, the sodium thionaphthene is placed on a filter, washes out finite toluene again and carries the still toluene-moist mass into water one with which it reacts while generating significant heat. The secluded Crude thionaphthene is produced by a one-time distillation of some toluene-containing First run and small amounts of high boiling «freed a residue and crystallized Compound obtained from a uniform boiling point of 21g to 22U '.

Claims (1)

PATENTANSPRUCH: Verfahren zur Gewinnung von Thionaphthen aus Steinkohlenteer durch Behandlung des aus letzterem gewonnenen Naphthalins mit Natriumamid oder mit Natrium in Gegenwart von Ammoniak oder mit Natrium allein, dadurch gekennzeichnet, daß man die von dem nicht angegriffenen Naphthalin abgetrennte Natriumverbindung des Thionaphthens mit Wasser spaltet.PATENT CLAIM: Process for the extraction of thionaphthene from coal tar by treating the naphthalene obtained from the latter with sodium amide or with Sodium in the presence of ammonia or with sodium alone, characterized in that the sodium compound separated from the unaffected naphthalene of thionaphthene splits with water.
DENDAT350737D Process for the production of thionaphthene from coal tar Expired DE350737C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE350737T

Publications (1)

Publication Number Publication Date
DE350737C true DE350737C (en) 1922-03-25

Family

ID=6263980

Family Applications (1)

Application Number Title Priority Date Filing Date
DENDAT350737D Expired DE350737C (en) Process for the production of thionaphthene from coal tar

Country Status (1)

Country Link
DE (1) DE350737C (en)

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