DE508890C - Process for the preparation of 1'-chloro-1-methylnaphthalene - Google Patents

Process for the preparation of 1'-chloro-1-methylnaphthalene

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Publication number
DE508890C
DE508890C DEI36705D DEI0036705D DE508890C DE 508890 C DE508890 C DE 508890C DE I36705 D DEI36705 D DE I36705D DE I0036705 D DEI0036705 D DE I0036705D DE 508890 C DE508890 C DE 508890C
Authority
DE
Germany
Prior art keywords
chloro
methylnaphthalene
preparation
naphthalene
formaldehyde
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
DEI36705D
Other languages
German (de)
Inventor
Dr Hans Lange
Dr Gustav Reddehen
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 DEI36705D priority Critical patent/DE508890C/en
Application granted granted Critical
Publication of DE508890C publication Critical patent/DE508890C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds

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

Description

Verfahren zur Darstellung von 1'-Chlor-l-methylnaphthalin w-Chlormethylderivate ,aromatischer Kohlenwasserstoffe werden bekanntlich durch Einwirkung von polymerisiertem Formaldehyd (Trioxymethylen) auf Kohlenwasserstoffe in Gegenwart gasförmiger Chlorwasserstoffsäure und eines Kondensationsmittels, wie Chlorzink, erhalten (G. B 1 a n c, Bulletin de la Soc. chim. de France, Serie q., Band 33 vo,m Jahre 1923, S.313/3I9; Chem. Centralblatt 1923, 1, S. 1571). Es wird dabei besonders betont, daß beim Arbeiten mit Naphthalin ein Lösungsmittel (Petroläther) erforderlich ist. Die Ausbeute an Chlormethylnaphthalin beträgt wegen der gleichzeitigen Bildung von Dinaphthylmethanderivaten nur etwa 27 0/0 der Theorie.Process for the preparation of 1'-chloro-l-methylnaphthalene w-chloromethyl derivatives, aromatic hydrocarbons, are known to be obtained by the action of polymerized formaldehyde (trioxymethylene) on hydrocarbons in the presence of gaseous hydrochloric acid and a condensing agent such as zinc chloride (G. B 1 anc, Bulletin de la Soc. chim. de France, series q., volume 33 vo, m years 1923, p. 313/319; Chem. Centralblatt 1923, 1, p. 1571). It is particularly emphasized that a solvent (petroleum ether) is required when working with naphthalene. The yield of chloromethylnaphthalene is due to the simultaneous formation of Dinaphthylmethanderivaten only about 27 0/0 of theory.

Es wurde nun überraschenderweise gefunden, daß sich die Überführung des Naphthalins in das i'-Chlor-i-methylnaphthalin in einfacher Weise und mit guter Ausbeute ermöglichen läßt, ohne Verwendung eines Lösungs- und Kondensationsmittels oder von polymerisiertem Formaldehyd, wenn man kristallisiertes Naphthalin in wäßriger Suspension mit monomolekularem Formaldehyd und konz. Chlorwasserstolfsäur e zusammenbringt und das Gemisch unter vorsichtigem Erwärmen rührt, wobei zweckmäßig durch gleichzeitiges Einleiten von gasförmigem Chlorwasserstoff für die Aufrechterhaltung einer hinreichenden Konzentration gesorgt wird. Bei Temperaturen von etwa 6o bis 65° werden leicht Ausbeuten von über 6o % der Theorie erhalten.It has now surprisingly been found that the transfer of the naphthalene in the i'-chloro-i-methylnaphthalene in a simple manner and with good Allow yield without the use of a solvent and condensing agent or of polymerized formaldehyde, if you crystallized naphthalene in aqueous Suspension with monomolecular formaldehyde and conc. Brings hydrochloric acid e and stir the mixture with careful heating, advantageously by simultaneous Introduction of gaseous hydrogen chloride to maintain sufficient Concentration is taken care of. Yields are easy at temperatures of about 60 to 65 ° received more than 60% of theory.

Das i'-Chlor-i-methylnaphthalin stellt ein wertvolles Zwischenprodukt, z. B. für die Herstellung von Farbstoffen, dar. Beispiel 768 Teile gepulvertes Naphthalin werden in 75o Teile wäßrige Formaldehydlösung (3oprozentig) und 3ooo Teile konz. Chlorwasserstoffsäure eingetragen, worauf das Gemisch unter Rühren und Einleiten von Chlorwasserstoff auf 6o bis 65° erwärmt wird. Nach io Stunden trennt man das auf der Oberfläche schwimmende öl ab und fraktioniert es im Vakuum. Man erhält neben Zoo Teilen wiedergewonnenem Naphthalin 649 Teile i'- Chlor-i -methylnaphthalüi = 61,q. % der Theorie oder 83,1 %, bezogen auf verbrauchtes Naphthalin. Das i'-Chlor-i-methylnaphthalin siedet unter 12 mm Druck bei 153°, erstarrt in der Kälte und läßt sich aus Alkohol umkristallisieren. Es schmilzt bei 31 bis 32".The i'-chloro-i-methylnaphthalene is a valuable intermediate, z. B. for the manufacture of dyes. Example 768 parts of powdered naphthalene are concentrated in 75o parts of aqueous formaldehyde solution (3%) and 3ooo parts. Added hydrochloric acid, whereupon the mixture is stirred and introduced is heated by hydrogen chloride to 6o to 65 °. After ten hours you separate them oil floating on the surface and fractionates it in a vacuum. One receives besides Zoo parts of recovered naphthalene 649 parts of i'-chloro-i -methylnaphthalii = 61, q. % of theory or 83.1%, based on naphthalene consumed. The i'-chloro-i-methylnaphthalene boils under 12 mm pressure at 153 °, solidifies in the cold and can be made from alcohol recrystallize. It melts at 31 to 32 ".

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von V-Chlori-methylnaphthalin, dadurch gekennzeichnet, da13 man auf eine wäßrige Suspension von kristallisiertem Naphthalin monorizolekularen Formaldehyd in Gegenwart von konzentrierter Chlorwasserstoffsäure zweckmäßig unter Einleiten von gasförmigem Chlorwasserstoff und Erwärmen einwirken läßt.PATENT CLAIM: Process for the preparation of V-chloro-methylnaphthalene, characterized in that an aqueous suspension of crystallized Naphthalene monorizolecular formaldehyde in the presence of concentrated hydrochloric acid expediently act with the introduction of gaseous hydrogen chloride and heating leaves.
DEI36705D 1929-01-12 1929-01-13 Process for the preparation of 1'-chloro-1-methylnaphthalene Expired DE508890C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI36705D DE508890C (en) 1929-01-12 1929-01-13 Process for the preparation of 1'-chloro-1-methylnaphthalene

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE337289X 1929-01-12
DEI36705D DE508890C (en) 1929-01-12 1929-01-13 Process for the preparation of 1'-chloro-1-methylnaphthalene

Publications (1)

Publication Number Publication Date
DE508890C true DE508890C (en) 1930-10-02

Family

ID=25817201

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI36705D Expired DE508890C (en) 1929-01-12 1929-01-13 Process for the preparation of 1'-chloro-1-methylnaphthalene

Country Status (1)

Country Link
DE (1) DE508890C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE846163C (en) * 1949-12-16 1952-08-11 Ferdinand Dr Meyer Process for the production of synthetic resins
DE1082893B (en) * 1957-05-02 1960-06-09 Bergwerksverband Gmbh Process for the chloroalkylation of aromatic compounds

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE846163C (en) * 1949-12-16 1952-08-11 Ferdinand Dr Meyer Process for the production of synthetic resins
DE1082893B (en) * 1957-05-02 1960-06-09 Bergwerksverband Gmbh Process for the chloroalkylation of aromatic compounds

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