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DE441587C - Process for the preparation of halogenation products of perylenetetracarboximide and its derivatives - Google Patents

Process for the preparation of halogenation products of perylenetetracarboximide and its derivatives

Info

Publication number
DE441587C
DE441587C DEK83747D DEK0083747D DE441587C DE 441587 C DE441587 C DE 441587C DE K83747 D DEK83747 D DE K83747D DE K0083747 D DEK0083747 D DE K0083747D DE 441587 C DE441587 C DE 441587C
Authority
DE
Germany
Prior art keywords
perylenetetracarboximide
derivatives
preparation
halogenation products
halogenation
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
DEK83747D
Other languages
German (de)
Inventor
Dr Wilhelm Neugebauer
Dr Maximilian P Schmidt
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.)
Kalle GmbH and Co KG
Original Assignee
Kalle GmbH and Co KG
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 Kalle GmbH and Co KG filed Critical Kalle GmbH and Co KG
Priority to DEK83747D priority Critical patent/DE441587C/en
Application granted granted Critical
Publication of DE441587C publication Critical patent/DE441587C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series

Landscapes

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

Description

Verfahren zur Darstellung von Halogenisierungsprodukten des Perylentetracarbonsäureimids und seiner Derivate. Es ist gefunden worden, daß man Perylentetracarbonsäureimide, die z. B. durch Verschmelzen von Naphthalin-i,8-dicarbonsäureimiden mit Ätzalkali erhältlich sind, glatt und in guter Ausbeute halogenisieren kann, wenn man Chlorsulfonsäure als Lösungsmittel oder Verdünnungsmittel anwendet.Process for the preparation of halogenation products of perylenetetracarboximide and its derivatives. It has been found that perylenetetracarboximides, the z. B. by fusing naphthalene-i, 8-dicarboximides with caustic alkali are obtainable, can be halogenated smoothly and in good yield if chlorosulfonic acid is used uses as a solvent or diluent.

Beispiel. io Gewichtsteile Perylentetracarbönsäurediimid werden unter Vermeidung einer Temperaturerhöhung in etwa i5o Gewichtsteilen Chlorsulfonsäure gelöst und nach Zusatz von etwas Jod bei Zimmertemperatur und gewöhnlichem Druck mit gasförmigem Chlor behandelt. Die Chloraufnahme erfolgt sehr glatt, und man gelangt mühelos bis zur Tetrachlorstufe, was leicht daran zu erkennen ist, daß eine auf Baumwolle aufgefärbte Probe beim kochenden Seifen von einem kräftigen Gelbrot nach Lila umschlägt. Man scheidet das Tetrachlorprodukt durch Eingießen in Eis ab, filtriert und wäscht neutral. Die Ausbeute ist sehr gut. An Stelle von Jod können auch andere Halogenüberträger, z. B. Eisenpulver, verwendet werden, doch läßt sich das Verfahren auch ohne solche ausführen.Example. 10 parts by weight of perylenetetracarbonic acid diimide are below Avoidance of a temperature increase in about 150 parts by weight of chlorosulfonic acid dissolved and after adding a little iodine at room temperature and ordinary pressure treated with gaseous chlorine. The chlorine uptake is very smooth, and you get there effortlessly up to the tetrachlor stage, which can be easily recognized by the fact that a Cotton-colored sample after boiling soapy from a strong yellow-red Purple turns. The tetrachloro product is separated off by pouring into ice and filtered and washes neutral. The yield is very good. Instead of iodine, others can Halogen carriers, e.g. B. iron powder, can be used, but the method run even without such.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Halogenisierungsprodukten des Perylentetracarbonsäureimids und seiner Derivate, dadurch gekennzeichnet, daß man die Halogenisierung des Perylentetracarbonsäureimids oder seiner Derivate (unter Ausschluß der Farbstoffe nach Patentschrift 276 956) in Gegenwart von Chlorsulfonsäure ausführt.Claim: Process for the preparation of halogenation products of perylenetetracarboximide and its derivatives, characterized in that the halogenation of perylenetetracarboximide or its derivatives (excluding the dyes according to patent specification 276 956) is carried out in the presence of chlorosulfonic acid.
DEK83747D 1922-10-27 1922-10-27 Process for the preparation of halogenation products of perylenetetracarboximide and its derivatives Expired DE441587C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEK83747D DE441587C (en) 1922-10-27 1922-10-27 Process for the preparation of halogenation products of perylenetetracarboximide and its derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEK83747D DE441587C (en) 1922-10-27 1922-10-27 Process for the preparation of halogenation products of perylenetetracarboximide and its derivatives

Publications (1)

Publication Number Publication Date
DE441587C true DE441587C (en) 1927-03-03

Family

ID=7234867

Family Applications (1)

Application Number Title Priority Date Filing Date
DEK83747D Expired DE441587C (en) 1922-10-27 1922-10-27 Process for the preparation of halogenation products of perylenetetracarboximide and its derivatives

Country Status (1)

Country Link
DE (1) DE441587C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3631678A1 (en) * 1986-09-18 1988-03-24 Basf Ag TETRACHLORPERYLEN-3,4,9,10-TETRACARBONSAEUREDIIMIDPIGMENT AND THEIR USE

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3631678A1 (en) * 1986-09-18 1988-03-24 Basf Ag TETRACHLORPERYLEN-3,4,9,10-TETRACARBONSAEUREDIIMIDPIGMENT AND THEIR USE

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