DE1243184B - 2, 2, 6, 6-tetrachlorocyclohexane-1-hydroxy-carboxylic acid amide- (1) - Google Patents

2, 2, 6, 6-tetrachlorocyclohexane-1-hydroxy-carboxylic acid amide- (1)

Info

Publication number
DE1243184B
DE1243184B DEN24908A DEN0024908A DE1243184B DE 1243184 B DE1243184 B DE 1243184B DE N24908 A DEN24908 A DE N24908A DE N0024908 A DEN0024908 A DE N0024908A DE 1243184 B DE1243184 B DE 1243184B
Authority
DE
Germany
Prior art keywords
tetrachlorocyclohexane
hydroxy
carboxylic acid
benzene
acid amide
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
DEN24908A
Other languages
German (de)
Inventor
Cornelis Johannes Schoot
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.)
Koninklijke Philips NV
Original Assignee
Philips Gloeilampenfabrieken NV
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 Philips Gloeilampenfabrieken NV filed Critical Philips Gloeilampenfabrieken NV
Publication of DE1243184B publication Critical patent/DE1243184B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
    • C07C23/02—Monocyclic halogenated hydrocarbons
    • C07C23/10—Monocyclic halogenated hydrocarbons with a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton

Description

DEUTSCHES WWW" PATENTAMTGERMAN WWW "PATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Deutsche KL: 12 ο - 25German KL: 12 ο - 25

Nummer: 1243 184Number: 1243 184

Aktenzeichen: N 249081V b/12 οFile number: N 249081V b / 12 ο

j[ 243 184 Anmeldetag: 30. April 1964j [243 184 filing date: April 30, 1964

Auslegetag: 29. Juni 1967·Opened on: June 29, 1967

Die Erfindung betrifft eine neue Verbindung, das 2,2,6,6-Tetrachlorcyclohexan-l-hydroxy-carbonsäureamid-(l) der FormelThe invention relates to a new compound, the 2,2,6,6-tetrachlorocyclohexane-l-hydroxy-carboxamide- (l) the formula

NH2 NH 2

Diese Verbindung ist wirksamer Bestandteil von Mitteln zur Bekämpfung schädlicher Organismen im Ackerbau; sie weist eine fungizide Wirkung auf. Weiterhin ist diese Verbindung als AusgangsmaterialThis compound is an effective component of means for combating harmful organisms in the Agriculture; it has a fungicidal effect. Furthermore, this compound is used as a starting material

bei der Herstellung wichtiger herbizidwirksamer Stoffe wie des 2,6-Dichlorbenzamids von Bedeutung.in the production of important herbicidal substances such as 2,6-dichlorobenzamide.

überraschenderweise wurde festgestellt, daß die Verbindung nach der Erfindung in nahezu quantitativer Ausbeute durch Verseifung von 2,2,6,6-Tetrachlorcyclohexanoncyanhydrin mit starken Säuren hergestellt werden kann. Als Säure kommen beispielsweise Phosphorsäure, Benzolsulfonsäure und Schwefelsäure in Frage. Die Reaktion wird im allgemeinen unter mäßiger Erhitzung, z. B. bei 40 bis 70C, in konzentrierter Schwefelsäure durchgeführt; unter diesen Bedingungen tritt keine Salzsäurebildung auf.Surprisingly, it was found that the compound according to the invention in almost quantitative Yield from saponification of 2,2,6,6-tetrachlorocyclohexanone cyanohydrin with strong acids can be produced. Examples of acids are phosphoric acid, benzenesulfonic acid and Sulfuric acid in question. The reaction is generally carried out with moderate heating, e.g. B. at 40 to 70C, carried out in concentrated sulfuric acid; no hydrochloric acid is formed under these conditions on.

Beispielexample

a) Herstellung des Ausgangsmaterials
2,2,6,6-Tetrachlorcyclohexanoncyanhydrina) Production of the starting material
2,2,6,6-tetrachlorocyclohexanone cyanohydrin

In einen mit einem Rührer, Tropftrichter und Thermometer versehenen Dreihalskolben werden eine benzolische Lösung von 118 g (0,5 Mol) 2,2,6,6-Tetrachlorcyclohexanon und 33 g eiskalte Essigsäure vorgelegt. Eine Lösung von 27 g (0,55 Mol) NaCN in 60 ml Wasser wird zugetropft, wobei die Temperatur zwischen —3 und — 3 C gehalten wird. Nach 10 Minuten Rühren wird die Benzolschicht von der Wasserschicht getrennt, die Wasserschicht noch zweimal mit Benzol extrahiert und diese Extrakte mit der Benzolschicht vereinigt, getrocknet, und anschließend das Benzol unter vermindertem Druck entfernt. Der Rückstand, der nach der IR-Analyse weniger als 50Zo 2,2,6,6-Tetrachlorcyclohexanon enthält, hat einen Schmelzpunkt von 125 bis 136 C Der Schmelzpunkt ist abhängig von der Geschwindig-2,2,6,6-Tetrachlorcyclohexan-1 -hydroxycarbonsäureamid-( 1)A benzene solution of 118 g (0.5 mol) of 2,2,6,6-tetrachlorocyclohexanone and 33 g of ice-cold acetic acid are placed in a three-necked flask equipped with a stirrer, dropping funnel and thermometer. A solution of 27 g (0.55 mol) of NaCN in 60 ml of water is added dropwise, the temperature being kept between -3 and -3 ° C. After stirring for 10 minutes, the benzene layer is separated from the water layer, the water layer is extracted twice more with benzene and these extracts are combined with the benzene layer, dried, and then the benzene is removed under reduced pressure. The residue, after the IR analysis is less than 5 0 Zo contains 2,2,6,6-Tetrachlorcyclohexanon has a melting point of 125-136 C. The melting point is dependent on the VELOCITY-2,2,6,6-Tetrachlorcyclohexan -1 -hydroxycarboxamide- (1)

Anmelder:Applicant:

Ν. V. Philips' Gloeilampenfabrieken,
Eindhoven (Niederlande)Ν. V. Philips' Gloeilampenfabrieken,
Eindhoven (Netherlands)

Vertreter:Representative:

Dipl.-Ing. H. Zoepke, Patentanwalt,
c München 5, Erhardtstr. 11Dipl.-Ing. H. Zoepke, patent attorney,
c Munich 5, Erhardtstr. 11

Als Erfinder benannt:
Cornells Johannes Schoot, Eindhoven
(Niederlande)Named as inventor:
Cornells Johannes Schoot, Eindhoven
(Netherlands)

Beanspruchte Priorität:Claimed priority:

Niederlande vom 2. Mai 1963 (292 268)Netherlands May 2, 1963 (292 268)

keit, mit der das Benzol entfernt wird. Dadurch, daß der Uberschuß 10 Minuten lang in Benzol gekocht und dann das Benzol unter normalem Druck abdestilliert wird, ergibt sich ein Produkt mit einem Schmelzpunkt von 102 bis 105 C. Die beiden Modifikationen weisen in Lösung das gleiche IR-Spektrum auf. Der Schmelzpunkt beträgt nach Umkristallisation aus einem Gemisch von 20% Benzol und 80% Petroläther (Siedebereich 80 bis 100 C) 104 bis 107: Cthe speed with which the benzene is removed. The fact that the excess is boiled in benzene for 10 minutes and then the benzene is distilled off under normal pressure results in a product with a melting point of 102 to 105 C. The two modifications have the same IR spectrum in solution. After recrystallization from a mixture of 20% benzene and 80% petroleum ether (boiling range 80 to 100 ° C.), the melting point is 104 to 107 : C

b) 2,2,6,6-Tetrachlorcyclohexanon-l-hydroxycarbonamide 1)b) 2,2,6,6-Tetrachlorocyclohexanone-1-hydroxycarbonamide 1)

50 g des oben beschriebenen Cyanhydrins werden 1 Stunde lang unter Rühren in 100 ml konzentrierter H2SO4 auf 55 bis 60: C erhitzt und dann auf Eis ausgegossen. Der Niederschlag wird abfiltriert und mit Wasser säurefrei gewaschen. Die Ausbeute beträgt 52 g, das sind 98%, bezogen auf das Cyanhydrin. Der Schmelzpunkt des erzielten Carbonsäureamids ist etwa 166 C. Bei Umkristallisierung aus Benzol wird eine Modifikation mit einem Schmelzpunkt von 204 C erhalten. Die beiden Modifikationen weisen in Lösung das gleiche IR-Spektrum auf.50 g of the cyanohydrin described above are heated to 55 to 60 : C for 1 hour with stirring in 100 ml of concentrated H2SO4 and then poured onto ice. The precipitate is filtered off and washed acid-free with water. The yield is 52 g, that is 98% based on the cyanohydrin. The melting point of the carboxamide obtained is about 166 ° C. When recrystallizing from benzene, a modification with a melting point of 204 ° C. is obtained. The two modifications show the same IR spectrum in solution.

709 608 458709 608 458

Claims (1)

Patentansprüche:
1. Verfahren zur Herstellung von 2,2,6,6-Tetrachlorcyclohexan -1 -hydroxy-carbonsäureamid-( 1), dadurch gekennzeichnet, daß man 2,2,6,6 - Tetrachlorcyclohexanoncyanhydrin mitPatent claims:
1. A process for the preparation of 2,2,6,6-tetrachlorocyclohexane -1-hydroxy-carboxamide- (1), characterized in that 2,2,6,6 - tetrachlorocyclohexanone cyanohydrin with einer starken Säure unter mäßiger Erwärmung verseift.saponified with a strong acid with moderate heating. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man die Verseifung bei einer Temperatur zwischen 40 und 70° C durchführt.2. The method according to claim 1, characterized in that the saponification at a Temperature between 40 and 70 ° C performs. 709 608/458 6.67 © Bundesdruckerei Berlin709 608/458 6.67 © Bundesdruckerei Berlin
DEN24908A 1963-05-02 1964-04-30 2, 2, 6, 6-tetrachlorocyclohexane-1-hydroxy-carboxylic acid amide- (1) Pending DE1243184B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL292268 1963-05-02

Publications (1)

Publication Number Publication Date
DE1243184B true DE1243184B (en) 1967-06-29

Family

ID=19754669

Family Applications (1)

Application Number Title Priority Date Filing Date
DEN24908A Pending DE1243184B (en) 1963-05-02 1964-04-30 2, 2, 6, 6-tetrachlorocyclohexane-1-hydroxy-carboxylic acid amide- (1)

Country Status (10)

Country Link
AT (1) AT247851B (en)
BE (1) BE647497A (en)
BR (1) BR6458811D0 (en)
CH (1) CH445477A (en)
DE (1) DE1243184B (en)
DK (1) DK123026B (en)
FR (1) FR1397572A (en)
GB (1) GB1066812A (en)
NL (1) NL292268A (en)
SE (1) SE305440B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2675501A1 (en) * 1991-04-17 1992-10-23 Rhone Poulenc Chimie Synthetic intermediates having an alcoholic polyhalogenated hexane ring and processes for their preparation
EP0511036A1 (en) * 1991-04-17 1992-10-28 Rhone-Poulenc Chimie Synthesis intermediaries with an hexanic ring, and process for their preparation

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114835589B (en) * 2022-05-30 2024-03-15 河南金鹏化工有限公司 Preparation method of 2,4-difluoro-3,5-dichloroaniline

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2675501A1 (en) * 1991-04-17 1992-10-23 Rhone Poulenc Chimie Synthetic intermediates having an alcoholic polyhalogenated hexane ring and processes for their preparation
EP0511036A1 (en) * 1991-04-17 1992-10-28 Rhone-Poulenc Chimie Synthesis intermediaries with an hexanic ring, and process for their preparation
US5817890A (en) * 1991-04-17 1998-10-06 Rhone-Poulenc Chimie Process for preparation of halogenated or pseudohalogenated cyclic organic compounds

Also Published As

Publication number Publication date
BR6458811D0 (en) 1973-08-07
FR1397572A (en) 1965-04-30
GB1066812A (en) 1967-04-26
CH445477A (en) 1967-10-31
AT247851B (en) 1966-06-27
DK123026B (en) 1972-05-08
NL292268A (en)
BE647497A (en) 1964-11-04
SE305440B (en) 1968-10-28

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