DE1149349B - Process for the preparation of N, N, N'-triacetylmethylenediamine or N, N, N ', N'-tetraacetylmethylenediamine or mixtures thereof - Google Patents

Process for the preparation of N, N, N'-triacetylmethylenediamine or N, N, N ', N'-tetraacetylmethylenediamine or mixtures thereof

Info

Publication number
DE1149349B
DE1149349B DEK45423A DEK0045423A DE1149349B DE 1149349 B DE1149349 B DE 1149349B DE K45423 A DEK45423 A DE K45423A DE K0045423 A DEK0045423 A DE K0045423A DE 1149349 B DE1149349 B DE 1149349B
Authority
DE
Germany
Prior art keywords
tetraacetylmethylenediamine
triacetylmethylenediamine
mixtures
acetic anhydride
preparation
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.)
Pending
Application number
DEK45423A
Other languages
German (de)
Inventor
Cornelis Ugo Kloosterman
Wilhelmus Johannes Corn Viveen
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.)
KONINK IND MIJ VOORHEEN NOURY
Original Assignee
KONINK IND MIJ VOORHEEN NOURY
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 KONINK IND MIJ VOORHEEN NOURY filed Critical KONINK IND MIJ VOORHEEN NOURY
Publication of DE1149349B publication Critical patent/DE1149349B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3917—Nitrogen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/06—Inorganic compounds
    • C11D9/08—Water-soluble compounds
    • C11D9/10—Salts

Description

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

K 45423 IVb/12 οK 45423 IVb / 12 ο

ANMELDETAG: 27. MAI 1960 REGISTRATION DATE: MAY 27, 1960

BEKANNTMACHUNG
DER ANMELDUNG
UND AUSGABE DER
AUSLEGESCHRIFT: 30. MAI 1963 NOTICE
THE REGISTRATION
AND ISSUE OF THE
EDITORIAL: MAY 30, 1963

Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Ν,Ν,Ν'-Triacetylmethylendiamin bzw. Ν,Ν,Ν',Ν'-Tetraacetylmethylendiamin der FormelThe invention relates to a process for the preparation of Ν, Ν, Ν'-triacetylmethylenediamine or Ν, Ν, Ν ', Ν'-tetraacetylmethylenediamine der formula

CH3CO-CH 3 CO-

N-CH2-N^N-CH 2 -N ^

OCCH3 OCCH3 OCCH 3 OCCH 3

in der R ein Wasserstoffatom oder die CH3CO-Gruppe bedeutet, oder deren Mischungen.in which R denotes a hydrogen atom or the CH 3 CO group, or mixtures thereof.

Es ist bekannt, daß man Amine mit Essigsäureanhydrid acetylieren kann, wobei die bei der Umsetzung entstehende Essigsäure nicht die volle Ausnutzung des Amins hindert.It is known that amines can be acetylated with acetic anhydride, which in the reaction the resulting acetic acid does not prevent the full utilization of the amine.

Es wurde nun gefunden, daß man Ν,Ν,Ν'-Triacetylmethylendiamin bzw. Ν,Ν,Ν',Ν'-Tetraacetylmethylendiamin oder deren Mischungen herstellen kann, indem man Ν,Ν'-Diacetylmethylendiamin mit überschüssigem Essigsäureanhydrid in der Siede- ao hitze unter Rückfluß ohne Entfernen der gebildeten Essigsäure bzw. mit überschüssigem Essigsäureanhydrid und vollständigem oder teilweisem Abdestillieren der gebildeten Essigsäure bei einer Bodentemperatur von 140 bis 1460C acetyliert.It has now been found that Ν, Ν, Ν'-triacetylmethylenediamine or Ν, Ν, Ν ', Ν'-tetraacetylmethylenediamine or mixtures thereof can be prepared by Ν, Ν'-diacetylmethylenediamine with excess acetic anhydride in the boiling point heat under reflux without removing the acetic acid formed or with excess acetic anhydride and completely or partially distilling off the acetic acid formed at a bottom temperature of 140 to 146 ° C. acetylated.

Beispiel 1
Herstellung von Ν,Ν,Ν'-Triacetylmethylendiaminexample 1
Production of Ν, Ν, Ν'-triacetylmethylenediamine

325 g (2,5 Mol) Diacetylmethylendiamin (F. = 200 bis 200,5° C), das in bekannter Weise aus Acetamid und Paraformaldehyd hergestellt wurde, werden unter Erhitzen in 3060 g (30 Mol) Essigsäureanhydrid (98%ig) gelöst. Nach 4stündigem Erhitzen der Mischung unter Rückfluß wird die Essigsäure-Essigsäureanhydrid-Mischung unter vermindertem Druck abdestilliert, wobei 433 g eines langsam kristallisierenden Produkts zurückbleiben. Durch Umkristallisation aus 433 ecm Isopropylalkohol werden 359 g (2,09 Mol) Ν,Ν,Ν'-Triacetylmethylendiamin mit einem Schmelzpunkt von 83 bis 84° C erhalten.325 g (2.5 moles) diacetylmethylenediamine (m.p. = 200 up to 200.5 ° C), which was produced in a known manner from acetamide and paraformaldehyde dissolved with heating in 3060 g (30 mol) of acetic anhydride (98%). After heating the Mixture under reflux is the acetic acid-acetic anhydride mixture under reduced Distilled off under pressure, leaving 433 g of a slowly crystallizing product. By Recrystallization from 433 ecm of isopropyl alcohol gives 359 g (2.09 mol) of Ν, Ν, Ν'-triacetylmethylenediamine obtained with a melting point of 83 to 84 ° C.

Beispiel 2Example 2

Herstellung von Ν,Ν,Ν',Ν'-TetraacetylmethylendiaminProduction of Ν, Ν, Ν ', Ν'-tetraacetylmethylenediamine

325 g (2,5 Mol) Ν,Ν'-Diacetylmethylendiamin (F. = 200 bis 200,50C) werden unter Erhitzen in 1530 g (15 Mol) Essigsäureanhydrid (98°/oig) gelöst. Mit Hilfe einer Fraktionierkolonne wird die während der Umsetzung gebildete Essigsäure bei einer BodenVerfahren zur Herstellung von325 g (2.5 mol) Ν, Ν'-Diacetylmethylendiamin (F. = 200 to 200.5 0 C) are dissolved under heating in 1530 g (15 mol) of acetic anhydride (98 ° / oig). With the help of a fractionation column, the acetic acid formed during the reaction is used in a soil process for the production of

NjNjN'-Triacetylmethylendiamin bzw. Ν,Ν,Ν^Ν'-TetraacetylmethylendiaminNjNjN'-triacetylmethylenediamine or Ν, Ν, Ν ^ Ν'-tetraacetylmethylenediamine

oder deren Mischungenor their mixtures

Anmelder:Applicant:

Koninklijke Industrieele MaatschappijKoninklijke Industrieele Maatschappij

voorheen Noury & van der Lande N. V.,voorheen Noury & van der Lande N.V.,

Deventer (Niederlande)Deventer (Netherlands)

Vertreter: Dr. A. Ullrich und Dr. T. Ullrich, Patentanwälte, Heidelberg, Bismarckstr. 17Representative: Dr. A. Ullrich and Dr. T. Ullrich, patent attorneys, Heidelberg, Bismarckstr. 17th

Beanspruchte Priorität: Großbritannien vom 13. Mai 1960 (Nr. 21 220)Claimed priority: Great Britain May 13, 1960 (No. 21 220)

Wilhelmus Johannes Cornells Viveen und Cornells Ugo Kloosterman, DeventerWilhelmus Johannes Cornells Viveen and Cornells Ugo Kloosterman, Deventer

(Niederlande), sind als Erfinder genannt worden(Netherlands) have been named as inventors

temperatur von 140 bis 145 0C in einem Zeitraum von 14 Stunden abdestilliert.temperature of 140 to 145 0 C distilled off over a period of 14 hours.

Die Umsetzung ist beendet, wenn das Destillat den Siedepunkt und den Brechungsindex von reinem Essigsäureanhydrid hat.The reaction is complete when the distillate has the boiling point and the refractive index of pure acetic anhydride.

Das Destillat beträgt 425 g und enthält 330 g Essigsäure.The distillate is 425 g and contains 330 g of acetic acid.

Durch Destillieren unter vermindertem Druck wird das gesamte Essigsäureanhydrid, das noch in der Reaktionsmischung vorhanden ist, entfernt. Man erhält 523 g Rohprodukt (theoretisch 535 g).All acetic anhydride that is still in the reaction mixture is present, removed. 523 g of crude product are obtained (theoretical 535 g).

Nach dem Umkristallisieren aus 523 ecm Isopropylalkohol werden 480 g (= 2,25 Mol) reines Ν,Ν,Ν',Ν'-Tetraacetylmethylendiamin mit einem Schmelzpunkt von 95 bis 96° C erhalten. 45 After recrystallization from 523 ecm of isopropyl alcohol, 480 g (= 2.25 mol) of pure Ν, Ν, Ν ', Ν'-tetraacetylmethylenediamine with a melting point of 95 to 96 ° C. are obtained. 45

Beispiel 3Example 3

Herstellung einer Mischung aus Tri- und TetraacetylmethylendiaminPreparation of a mixture of tri- and tetraacetylmethylenediamine

325 g (2,5 Mol) Diacetylmethylendiamin (F. = 200 bis 200,50C) werden unter Erhitzen in 1530 g (15 Mol) Essigsäureanhydrid (98%ig) gelöst.325 g (2.5 mol) Diacetylmethylendiamin (F. = 200 to 200.5 0 C) are dissolved under heating in 1530 g (15 moles) of acetic anhydride (98% strength).

309 598/333309 598/333

Mit Hilfe einer Fraktionierkolonne wurden während der Reaktion 160 g Essigsäure bei einer Ausgangstemperatur von 140 bis 145°C in 4 Stunden abdestilliert.With the aid of a fractionating column, 160 g of acetic acid were obtained at an initial temperature during the reaction distilled from 140 to 145 ° C in 4 hours.

Aus der Reaktionsmischung wurden die Lösungsmittel unter vermindertem Druck abdestilliert, wobei man 490 g Rohprodukt erhielt, das neben Triacetylmethylendiamin auch Tetraacetylmethylendiamin enthielt.The solvents were distilled off from the reaction mixture under reduced pressure, whereby 490 g of crude product were obtained which, in addition to triacetylmethylenediamine, also tetraacetylmethylenediamine contained.

Durch fraktionierte Destillation unter vermindertem Druck konnten 148 g Ν,Ν,Ν'-Triacetylmethylendiamin (Kp.2 = 129 bis 131 °C) und 301 g Ν,Ν,Ν',Ν'-Tetraacetylmethylendiamin (Kp.2 = 138 bis 140°C) aus dem Rohprodukt abgetrennt werden.By fractional distillation under reduced pressure, 148 g of Ν, Ν, Ν'-triacetylmethylenediamine (b.p. 2 = 129 to 131 ° C) and 301 g of Ν, Ν, Ν ', Ν'-tetraacetylmethylenediamine (b.p. 2 = 138 to 140 ° C) are separated from the crude product.

Die nach dem Verfahren der Erfindung herstellbaren Verbindungen können als Aktivatoren in Wasch- und bzw. oder Bleichmitteln, z. B. in Geschirrspülmitteln, verwendet werden, die neben einer anionischen oder kationischen oder einer nichtionogenen oberflächenaktiven Verbindung eine aktiven Sauerstoff abgebende' Verbindung enthalten.The compounds which can be prepared by the process of the invention can be used as activators in detergents and / or bleaches, e.g. B. in dishwashing detergents, used in addition to an anionic or cationic or a nonionic surface-active compound an active Oxygen-releasing compound included.

Claims (1)

PATENTANSPRUCH:
Verfahren zur Herstellung von Ν,Ν,Ν'-Triacetylmethylendiamin bzw. Ν,Ν,Ν',Ν'-Tetraacetylmethylendiamin der FormelPATENT CLAIM:
Process for the preparation of Ν, Ν, Ν'-triacetylmethylenediamine or Ν, Ν, Ν ', Ν'-tetraacetylmethylenediamine of the formula —CH2- n—CH 2 - n OCCH3 OCCH 3 p OCCH3 p OCCH 3 in der R ein Wasserstoffatom oder die CH3CO-Gruppe bedeutet, oder deren Mischungen, dadurch gekennzeichnet, daß man N,N'-Diacetylmethylendiamin mit überschüssigem Essigsäureanhydrid in der Siedehitze unter Rückfluß ohne Entfernen der gebildeten Essigsäure bzw. mit überschüssigem Essigsäureanhydrid und vollständigem oder teilweisem Abdestillieren der gebildeten Essigsäure bei einer Bodentemperatur von 140 bis 145°C acetyliert.in which R is a hydrogen atom or the CH 3 CO group, or mixtures thereof, characterized in that N, N'-diacetylmethylenediamine with excess acetic anhydride at the boiling point under reflux without removing the acetic acid formed or with excess acetic anhydride and complete or partial distilling off of the acetic acid formed at a bottom temperature of 140 to 145 ° C acetylated. In Betracht gezogene Druckschriften:
Houben—Weyl, Methoden der organischen Chemie, 4. Auflage, 1958, Bd. XI/2, S. 30 bis 34.Considered publications:
Houben-Weyl, Methods of Organic Chemistry, 4th Edition, 1958, Vol. XI / 2, pp. 30 to 34. 309 598/333 5.63309 598/333 5.63
DEK45423A 1959-06-19 1960-05-27 Process for the preparation of N, N, N'-triacetylmethylenediamine or N, N, N ', N'-tetraacetylmethylenediamine or mixtures thereof Pending DE1149349B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB21220/59A GB907356A (en) 1959-06-19 1959-06-19 Improvements in or relating to washing and/or bleaching compositions
GB2606159 1959-07-29
GB3469559 1959-10-13

Publications (1)

Publication Number Publication Date
DE1149349B true DE1149349B (en) 1963-05-30

Family

ID=27257993

Family Applications (2)

Application Number Title Priority Date Filing Date
DENDAT1162967D Pending DE1162967B (en) 1959-06-19 Detergents and / or bleaches
DEK45423A Pending DE1149349B (en) 1959-06-19 1960-05-27 Process for the preparation of N, N, N'-triacetylmethylenediamine or N, N, N ', N'-tetraacetylmethylenediamine or mixtures thereof

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DENDAT1162967D Pending DE1162967B (en) 1959-06-19 Detergents and / or bleaches

Country Status (7)

Country Link
US (1) US3163606A (en)
BE (1) BE591624A (en)
CA (2) CA678942A (en)
DE (2) DE1149349B (en)
FI (1) FI42698B (en)
GB (3) GB907356A (en)
NL (4) NL239952A (en)

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GB907358A (en) 1962-10-03
US3163606A (en) 1964-12-29
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GB907357A (en) 1962-10-03
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FI42698B (en) 1970-06-30
GB907356A (en) 1962-10-03
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CA678942A (en) 1964-01-28
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DE1162967B (en) 1964-02-13

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