DE1014991B - Process for the production of cycloaliphatic 1,2-diamines - Google Patents
Process for the production of cycloaliphatic 1,2-diaminesInfo
- Publication number
- DE1014991B DE1014991B DEG19860A DEG0019860A DE1014991B DE 1014991 B DE1014991 B DE 1014991B DE G19860 A DEG19860 A DE G19860A DE G0019860 A DEG0019860 A DE G0019860A DE 1014991 B DE1014991 B DE 1014991B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- urea
- carbon dioxide
- solution
- filtered
- 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
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
Die Erfindung bezieht sich auf ein neues Verfahren zur Herstellung von cycloaliphatischen 1, 2-Diaminen, welche beispielsweise wertvolle Ausgangsstoffe für Arzneimittel, Schädlingsbekämpfungsmittel und Textilhilfsmittel darstellen. The invention relates to a new process for the preparation of cycloaliphatic 1, 2-diamines, which represent, for example, valuable starting materials for pharmaceuticals, pesticides and textile auxiliaries.
Es wurde überraschenderweise gefunden, daß man cycloaliphatische 1,2-Diamine mit sechs bis acht Ringgliedern in dem die Aminogruppen tragenden Ring entsprechend der allgemeinen FormelIt has surprisingly been found that cycloaliphatic 1,2-diamines with six to eight ring members can be used in the ring bearing the amino groups according to the general formula
NH,NH,
XH-NH9 XH-NH 9
worin R einen die Gruppe ,CH — CH, zu einemwherein R one the group, CH - CH, to one
Cycloalkylen-, Bicycloalkylen- oder Benzocycloalkenylenrest ergänzenden, zweiwertigen Kohlenwasserstoffrest mit 1,4-, 1,5- oder l,6ständigen Valenzen bedeutet, aus den ao leicht zugänglichen a-Halogencycloalkanonen der allgemeinen FormelCycloalkylene, bicycloalkylene or benzocycloalkenylene radical supplementing, divalent hydrocarbon radical with 1,4-, 1,5- or 1,6-valences means, from the ao easily accessible a-halocycloalkanones of the general formula
XOXO
IIII
XH-HaiXH shark
worin Hai Chlor oder Brom bedeutet und R denselben zweiwertigen Kohlenwasserstoffrest wie in Formel I bedeutet, in einer mit guten Ausbeuten durchführbaren dreistufigen Reaktionsfolge herstellen kann, indem man ein Halogenketon der allgemeinen Formel II mit Harnstoff in Gegenwart eines Halogenwasserstoffacceptors erhitzt, das entstandene Imidazolon von einer der beiden tautomeren Formelnwhere Hal is chlorine or bromine and R is the same divalent hydrocarbon radical as in formula I, can be prepared in a three-stage reaction sequence that can be carried out with good yields by a halogen ketone of the general formula II is heated with urea in the presence of a hydrogen halide acceptor, the resulting imidazolone from one of the two tautomeric formulas
Verfahren zur Herstellung
von cycloaliphatischen 1,2-DiaminenMethod of manufacture
of cycloaliphatic 1,2-diamines
Anmelder:
J. R. Geigy A. G., Basel (Schweiz)Applicant:
JR Geigy AG, Basel (Switzerland)
Vertreter: Dr. F. Zumstein
und Dipl.-Chem, Dr. rer. nat. E. Assmann,
Patentanwälte, München 2, Bräuhausstr. 4Representative: Dr. F. Zumstein
and Dipl.-Chem, Dr. rer. nat. E. Assmann,
Patent Attorneys, Munich 2, Bräuhausstr. 4th
Beanspruchte Priorität:
Schweiz vom 16. Juni 1955Claimed priority:
Switzerland from June 16, 1955
Dr. Charles Simon, Basel (Schweiz),
ist als Erfinder genannt wordenDr. Charles Simon, Basel (Switzerland),
has been named as the inventor
XOXO
mittels katalytisch aktiviertem Wasserstoff zu einem Imidazolidon der allgemeinen Formelby means of catalytically activated hydrogen to an imidazolidone of the general formula
r;r;
XH-NH,XH-NH,
"CH-NH""CH-NH"
IVIV
hydriert und dieses vorzugsweise in mineralsaurer Lösung zu einem 1,2-Diaminocycloalkan, -bicycloalkan oder -benzocycloalkan der allgemeinen Formel I hydrolysiert. hydrogenated and this preferably in mineral acid solution to a 1,2-diaminocycloalkane, bicycloalkane or benzocycloalkane of the general formula I hydrolyzed.
Als Halogenwasserstoffacceptor kann in der ersten Stufe beispielsweise ein Überschuß an Harnstoff von mindestens der halben molaren Menge dienen. Zweckmäßig verwendet man in diesem Falle etwa 2 Mol oder mehr Harnstoff auf 1 Mol Halogenketon und verfolgt den Reaktionsverlauf an Hand der Kohlendioxydentwicklung. Die Reaktion zwischen Halogencycloalkanon und Harnstoff setzt meist zwischen 50 bis 150° ein und geht unter Wärmeentwicklung vor sich, so daß meist die Verwendung eines organischen Lösungs- und Verdünnungsmittels zur Beherrschung des Reaktionsverlaufs nötig ist.As a hydrogen halide acceptor in the first stage, for example, an excess of urea of Serve at least half the molar amount. It is expedient to use about 2 moles or in this case more urea to 1 mol of haloketone and follows the course of the reaction on the basis of the evolution of carbon dioxide. The reaction between halocycloalkanone and urea usually sets in between 50 and 150 ° and goes under Heat development in front of you, so that mostly the use of an organic solvent and diluent is necessary to control the course of the reaction.
Als geeignete Verdünnungsmittel haben sich Diäthylenglykoläther, wie z. B. der Diäthylenglykoldiäthyläther, erwiesen.Suitable diluents have been diethylene glycol ethers, such as. B. the diethylene glycol diethyl ether, proven.
Als Ausgangsstoffe der allgemeinen Formel II kommenAs starting materials of the general formula II come
z. B.^-Chlorcyclohexanon,2-Bromcyclohexanon, 3-Chlorl-methylcyclohexanon-(2), 4-Chlor-l-methyl-cyclohexanon - (3), 3 - Chlor -1 - methylcyclohexanon - (4), 2 - Chlor- und 2-Bromcycloheptanon, 2-Bromcyclooctanon sowie auch anellierte Halogencycloalkanone, z. B. lXhlordekahydronaphthalin-2-on, 3-Chlordekahydronaphthalin-2-on, 1-Chlor-und l-Bromtetrahydronaphthalin-2-on, in Frage.z. B. ^ - chlorocyclohexanone, 2-bromocyclohexanone, 3-chloro-methylcyclohexanone- (2), 4-chloro-1-methyl-cyclohexanone - (3), 3 - chlorine -1 - methylcyclohexanone - (4), 2 - chlorine- and 2-bromocycloheptanone, 2-bromocyclooctanone and also fused halogenocycloalkanones, e.g. B. lXhlordekahydronaphthalin-2-one, 3-chlorodecahydronaphthalen-2-one, 1-chloro- and l-bromotetrahydronaphthalen-2-one, are possible.
Geeignete Katalysatoren für die Hydrierung der PoIy-Suitable catalysts for the hydrogenation of the poly
methylenimidazolone der allgemeinen Formel III sindmethylenimidazolones of the general formula III are
z. B. Nickelkatalysatoren, wie Raney-Nickel oder Nickel auf Kieselgur, ferner auch Edelmetallkatalysatoren, z. B. Platinkatalysatoren.z. B. nickel catalysts, such as Raney nickel or nickel on kieselguhr, also noble metal catalysts, z. B. platinum catalysts.
Als Lösungsmittel kommen bei der Hydrierung z. B. Alkohole wie Äthanol oder Propanol in Betracht. Den Wasserstoff läßt man mit Vorteil unter Druck bei Tem-The solvents used in the hydrogenation are, for. B. alcohols such as ethanol or propanol into consideration. The Hydrogen is advantageously left under pressure at temperature
709 660/428709 660/428
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1014991X | 1955-06-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1014991B true DE1014991B (en) | 1957-09-05 |
Family
ID=4552670
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEG19860A Pending DE1014991B (en) | 1955-06-16 | 1956-06-15 | Process for the production of cycloaliphatic 1,2-diamines |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE1014991B (en) |
-
1956
- 1956-06-15 DE DEG19860A patent/DE1014991B/en active Pending
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