DE608314C - Process for the preparation of o-xylylene-1íñ8-naphthalene - Google Patents

Process for the preparation of o-xylylene-1íñ8-naphthalene

Info

Publication number
DE608314C
DE608314C DER85461D DER0085461D DE608314C DE 608314 C DE608314 C DE 608314C DE R85461 D DER85461 D DE R85461D DE R0085461 D DER0085461 D DE R0085461D DE 608314 C DE608314 C DE 608314C
Authority
DE
Germany
Prior art keywords
naphthalene
xylylene
preparation
phthaloylnaphthalene
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
DER85461D
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.)
ALFRED RIECHE DR
Original Assignee
ALFRED RIECHE DR
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 ALFRED RIECHE DR filed Critical ALFRED RIECHE DR
Priority to DER85461D priority Critical patent/DE608314C/en
Application granted granted Critical
Publication of DE608314C publication Critical patent/DE608314C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings

Description

Verfahren zur Darstellung von o-Xylylen-1- 8-naphthalin Es wurde gefunden, daß man o-Xylyleni - 8-naphthalin der Formel in sehr vorteilhafter Weise darstellen kann, wenn man peri-Phthaloylnaphthalin oder seine Halogenderivate mit reduzierend wirkenden Mitteln behandelt. Man verfährt z. B. in der Weise, daß man das Ausgangsmaterial der Zinkstaubdestillation im Wasserstoffstrom oder der katalytischen Reduktion mit Wasserstoff unterwirft. Gegenüber dem zur Darstellung von o-Xylylen-i - 8-naphthalin bereits bekannten Verfahren durch Reduktion von Oxy-i - 8-phthaloylnaphthalin bietet das vorliegende Verfahren den Vorteil, daß man das o-Xylylen-i - 8-naphthalin in wesentlich besseren Ausbeuten erhält. o-Xylyleni # 8-naphthalin stellt ein wichtiges Ausgangsmaterial für die Darstellung von Farbstoffen und pharmazeutischen Produkten dar. Beispiel i Ein Gemisch von 3 Teilen fein pulverisiertem peri-Phthaloylnaphthalin (erhältlich z. B. durch Erhitzen von Phthalsäureanhydrid und Naphthalin in Gegenwart von Aluminiumchlorid) mit 5o Teilen Zinkstaub wird in der üblichen Weise der Zinkstaubdestillation unterworfen. Man erhält in guter Ausbeute ein Rohprodukt, das durch einmaliges Umkristallisieren aus Alkohol den Kohlenwasserstoff in analysenreiner Form liefert. Das o-Xylylen-i - 8-naphthalin bildet farblose Nadeln vom Fp. 1i6,5°, die sich in heißer konzentrierter Schwefelsäure mit blutroter Farbe lösen. Nach einiger Zeit wird diese Lösung braun. Der Kohlenwasserstoff destilliert im Vakuum unzersetzt und kann auch auf diese Weise gereinigt werden. Beispiel e 2-Chlor-i - 8-phthaloylnaphthalin (dargestellt durch Behandeln von 2-Oxy-i - 8-phthaloylnaphthalin mit Phosphorpentachlorid wird, wie in Beispiel i angegeben, der Zinkstaubdestillation unterworfen. Es entsteht ein kristallinisches Rohprodukt, das durch einmaliges Umkristallisieren den reinen Kohlenwasserstoff liefert. Beispiel 3 In einem Druckgefäß werden ioo Teile peri-Phthaloylnaphthalin und 175o Teile Dekahydronaphthalin bei 18o° unter einem Druck von 15o at in Gegenwart von io Teilen eines Katalysators, der im wesentlichen aus Kupfer und Aluminiumoxyd besteht, mit Wasserstoff behandelt. Nach mehrstündiger Behandlung wird abgekühlt und das Reaktionsgemisch noch heiß vom Katalysator abfiltriert. Der nach dem Abdestillieren der Lösungsmittel hinterbleibende Rückstand wird aus Alkohol umkristallisiert. Hierbei erhält man reines o-XylAennaphthalin in einer Ausbeute von 57 °1o der Theorie.Process for the preparation of o-xylylene-1- 8-naphthalene It has been found that o-xylylene-8-naphthalene of the formula can represent in a very advantageous manner if you treat peri-phthaloylnaphthalene or its halogen derivatives with reducing agents. One proceeds z. B. in such a way that the starting material is subjected to zinc dust distillation in a stream of hydrogen or catalytic reduction with hydrogen. Compared to the process already known for the preparation of o-xylylene-1-8-naphthalene by reducing oxy-1-8-phthaloylnaphthalene, the present process offers the advantage that o-xylylene-1-8-naphthalene is obtained in significantly better yields receives. o-Xylyleni # 8-naphthalene is an important starting material for the preparation of dyes and pharmaceutical products. Example i A mixture of 3 parts of finely powdered peri-phthaloylnaphthalene (obtainable e.g. by heating phthalic anhydride and naphthalene in the presence of aluminum chloride) with 50 parts of zinc dust is subjected to zinc dust distillation in the usual manner. A crude product is obtained in good yield which, by recrystallizing once from alcohol, gives the hydrocarbon in analytically pure form. The o-xylylene-1-8-naphthalene forms colorless needles with a melting point of 1.5 °, which dissolve in hot, concentrated sulfuric acid with a blood-red color. After a while this solution will turn brown. The hydrocarbon distills undecomposed in a vacuum and can also be purified in this way. Example e 2-Chloro-1-8-phthaloylnaphthalene (prepared by treating 2-oxy-1-8-phthaloylnaphthalene with phosphorus pentachloride is subjected to zinc dust distillation as indicated in Example I. A crystalline crude product is formed which, by recrystallization once, is the EXAMPLE 3 100 parts of peri-phthaloylnaphthalene and 1750 parts of decahydronaphthalene are treated with hydrogen in a pressure vessel at 180 ° under a pressure of 150 at in the presence of 10 parts of a catalyst consisting essentially of copper and aluminum oxide more hours of treatment is cooled and the reaction mixture is filtered hot from the catalyst. the surviving after distilling off the solvent residue is recrystallized from alcohol. Here, there is obtained pure o-XylAennaphthalin in a yield of 57 ° 1o of theory.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von o-Xylylen-i # 8-naphthalin, dadurch gekennzeichnet, daß man peri-Phthaloylnaphthalin oder seine Halogenderivate mit reduzierend wirkenden Mitteln behandelt.PATENT CLAIM: Process for the preparation of o-xylylene-i # 8-naphthalene, characterized in that peri-phthaloylnaphthalene or its halogen derivatives treated with reducing agents.
DER85461D 1932-07-22 1932-07-22 Process for the preparation of o-xylylene-1íñ8-naphthalene Expired DE608314C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DER85461D DE608314C (en) 1932-07-22 1932-07-22 Process for the preparation of o-xylylene-1íñ8-naphthalene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DER85461D DE608314C (en) 1932-07-22 1932-07-22 Process for the preparation of o-xylylene-1íñ8-naphthalene

Publications (1)

Publication Number Publication Date
DE608314C true DE608314C (en) 1935-01-21

Family

ID=7417349

Family Applications (1)

Application Number Title Priority Date Filing Date
DER85461D Expired DE608314C (en) 1932-07-22 1932-07-22 Process for the preparation of o-xylylene-1íñ8-naphthalene

Country Status (1)

Country Link
DE (1) DE608314C (en)

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