DE1001982B - Process for the preparation of cyclooctanone oxime - Google Patents
Process for the preparation of cyclooctanone oximeInfo
- Publication number
- DE1001982B DE1001982B DEM27935A DEM0027935A DE1001982B DE 1001982 B DE1001982 B DE 1001982B DE M27935 A DEM27935 A DE M27935A DE M0027935 A DEM0027935 A DE M0027935A DE 1001982 B DE1001982 B DE 1001982B
- Authority
- DE
- Germany
- Prior art keywords
- oxime
- chlorine
- cyclooctanone
- cyclooctanone oxime
- molar ratio
- 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
- KTPUHSVFNHULJH-UHFFFAOYSA-N n-cyclooctylidenehydroxylamine Chemical compound ON=C1CCCCCCC1 KTPUHSVFNHULJH-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims description 7
- 239000004914 cyclooctane Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 3
- -1 oxime hydrochloride Chemical class 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- 239000004157 Nitrosyl chloride Substances 0.000 description 4
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 4
- 235000019392 nitrosyl chloride Nutrition 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- CEWJNZXLHJFHGA-UHFFFAOYSA-N n-cyclooctylidenehydroxylamine;hydrochloride Chemical compound Cl.ON=C1CCCCCCC1 CEWJNZXLHJFHGA-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
- FYFICIKYVOUSBU-UHFFFAOYSA-N nitrosocyclooctane Chemical compound O=NC1CCCCCCC1 FYFICIKYVOUSBU-UHFFFAOYSA-N 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- REWAQQRQPBRHOR-UHFFFAOYSA-N 1-chloro-1-nitrosocyclooctane Chemical compound O=NC1(Cl)CCCCCCC1 REWAQQRQPBRHOR-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical class ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- NHYCGSASNAIGLD-UHFFFAOYSA-N chlorine monoxide Inorganic materials Cl[O] NHYCGSASNAIGLD-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Cyclooktanonoxim Es ist bekannt, daß man Oxime cyclischer Ketone, insbesondere Cyclohexanonoxim, erhält, wenn man cyclische Kohlenwasserstoffe, wie Cyclohexan, im aktiven Licht mit beispielsweise Nitrosylchlorid oder -bromid behandelt (vgl. N a y 1 o r und A n d e r s o n, Journ. organ. Chem., Bd. 18, 1953, S. 115 sowie die französische Patentschrift 1047 049).Process for the preparation of cyclooctanone oxime It is known that oximes of cyclic ketones, in particular cyclohexanone oxime, are obtained when cyclic hydrocarbons, such as cyclohexane, are treated in active light with, for example, nitrosyl chloride or bromide (cf. N ay 1 or and A nderson, Journ Organ. Chem., Vol. 18, 1953, p. 115 and French patent specification 1 047 049).
Man hat ferner vorgeschlagen, Ketoxime in der Weise herzustellen, daß man auf gesättigte aliphatische oder cycloaliphatische Kohlenwasserstoffe im Licht ein Gemisch aus Stickstoffmonoxyd und Chlor einwirken läßt, welches Stickstoffmonoxyd in einem großen molekularen Überschuß gegenüber Chlor enthält, nämlich je Mol Cl2 etwa 5 bis 15 Mol NO, worauf man die dabei als Hauptprodukt entstehenden Bis-(nitroso)-Verbindungen und die als Nebenprodukt gebildeten 1-Chlor -1-nitrosoverbindungen durch Erwärmen oder Belichten oder durch Reduktion in die gewünschten Oxime umwandelt, vgl. die deutschen Patentanimeldungen M 22553 IVb/12o, M 25674 IVb/ 12 o und M 23939 IV b / 12 o.It has also been proposed to prepare ketoximes in such a way that saturated aliphatic or cycloaliphatic hydrocarbons are exposed to a mixture of nitrogen monoxide and chlorine, which contains nitrogen monoxide in a large molecular excess over chlorine, namely about 5 to 15 moles per mole of Cl2 NO, whereupon the bis (nitroso) compounds formed as the main product and the 1 - chloro-1-nitroso compounds formed as a by-product are converted into the desired oximes by heating or exposure or by reduction, see German patent applications M 22553 IVb / 12o, M 25674 IVb / 12 o and M 23939 IV b / 12 o.
In der erwähnten deutschen Patentanmeldung M 25674IVb/ 12o ist als Ausgangsstoff auch das Cyclooktan genannt. Es ist dort beschrieben, wie man -durch Einleiten eines Gemisches von Stickstoffmonoxyd und Chlor im Molverhältnis 10:1 in Cvclooktan bei 20 bis 25° unter Belichten mit einer L?@'-Lampe im Laufe von 5 Stunden eine grüne Lösung erhält, aus der man in einer Reihe von Arbeitsgängen schließlich sehr reines Cyclooktanonoxim gewinnt.In the aforementioned German patent application M 25674IVb / 12o is as The starting material is also called cyclooctane. There is a description of how to go through Introducing a mixture of nitrogen monoxide and chlorine in a molar ratio of 10: 1 in Cvclooctane at 20 to 25 ° with exposure to a L? @ 'lamp in the course of 5 Hours, a green solution is obtained, from which one finally proceeds in a series of operations very pure cyclooctanone oxime wins.
Es wurde nun gefunden, daß man unmittelbar Cyclooktanonoxim bzw. sein Hydrochlorid erhält, wenn man in Cvclooktan unter Belichten in lebhaftem Strom ein Gemisch aus Stickstoffmonoxyd und Chlor einleitet, das die beiden Gas-- im ungefähren @lolverhältnis bis höchstens 4:1 enthält.It has now been found that one can immediately be cyclooctanone oxime or Hydrochloride is obtained if one enters Cvclooktane with exposure in a brisk stream Mixture of nitrogen monoxide and chlorine introduces the two gases - approximately @ lol ratio up to a maximum of 4: 1 contains.
Dabei fällt schon nach kurzer Zeit das Cyclooktanonoximhydrochlorid, meistens in kristalliner Form, aus, ohne daß sich wesentliche Mengen von Nitroso- und Chlornitrosoverbindungen und von Salpetersäure- oder Salpetrigsäureestern oder sonstigen Nebenprodukten bilden.The cyclooctanone oxime hydrochloride falls after a short time, mostly in crystalline form, without significant amounts of nitroso and chloronitroso compounds and of nitric acid or nitrous acid esters or other by-products.
Das Oximhydrochlorid läßt sich leicht abtrennen. '.Ulan löst es in Wasser und neutralisiert die Lösung mit Alkali, wobei man sehr reines Cyclooktanonoxim erhält. Die Ausbeuten sind, auf verbrauchtes Cyclooktan berechnet, sehr befriedigend und erreichen im Falle der Verwendung eines Molverhältnisses N O: Cl2 = 3: 1 etwa 8511/o der Theorie, berechnet auf die angewendete Chlormenge. Sie sind bei Verwendung des dem Nitrosylchlorid entsprechenden Molverhältnisses N O: C12 = 2 :1 zwar geringer (etwa 5211/e der Theorie), aber gleichwohl höher als die Ausbeuten an Cyclohexanonoxim, die bei der Einwirkung von fertigem Nitrosylchlorid auf Cyclohexan im Licht erhalten wurden (vgl. Journ. Organic Chemistry, Bd. 18, 1953, S. 115 ff.).The oxime hydrochloride can easily be separated off. '.Ulan dissolves it in water and neutralizes the solution with alkali, whereby very pure cyclooctanone oxime is obtained. The yields, calculated on the cyclooctane consumed, are very satisfactory and, if a molar ratio NO: Cl2 = 3: 1 is used, they reach about 8511 / o of theory, calculated on the amount of chlorine used. When using the molar ratio NO: C12 = 2: 1 corresponding to the nitrosyl chloride, they are lower (about 5211 / e of theory), but nonetheless higher than the yields of cyclohexanone oxime that were obtained when finished nitrosyl chloride was exposed to cyclohexane in the light ( see Journ. Organic Chemistry, Vol. 18, 1953, pp. 115 ff.).
Das Verfahren hat vor den bekannten, allerdings nicht auf Cyclooktanonoxim gerichteten Verfahren zur Herstellung von Oximen aus den entsprechenden Ketonen und Hydroxylamin (vgl. die deutschen Patentschriften 888 693, 898 000 und 907 777) den Vorteil, daß man hier unmittelbar aus dem Kohlenwasserstoff und Stickstoffmonoxyd das gewünschte Oxim erhält, während man die für die bekannten Verfahren benutzten Ausgangsstoffe (Keton und Hydroxylamin) erst aus dem entsprechenden Kohlenwasserstoff und Stickstoffoxyden herstellen muß. Ähnliches gilt auch für das aus der deutschen Patentschrift 927 506 bekannte, ebenfalls nicht auf Cyclooktanonoxim gerichtete Verfahren, bei dem Nitrokohlenwasserstoffe, die zunächst aus den Kohlenwasserstoffen und Salpetersäure hergestellt werden müssen, durch Sulfide oder Polysulfide reduziert werden, worauf man die Oxime von den Oxydationsprodukten der Sulfide und Polysulfide, insbesondere elementarem Schwefel, umständlich befreien muß. Das Verfahren ist demgegenüber viel einfacher und liefert aus Cyclooktan und Stickstoffmonoxyd unmittelbar sehr reines Cy clooktanonoxim.The method has before the known, but not based on cyclooctanone oxime directed process for the preparation of oximes from the corresponding ketones and hydroxylamine (see German patents 888 693, 898 000 and 907 777) the advantage that you can get directly from the hydrocarbon and nitrogen monoxide the desired oxime is obtained while using those for the known methods Starting materials (ketone and hydroxylamine) only come from the corresponding hydrocarbon and must produce oxides of nitrogen. The same applies to that from the German Patent specification 927 506 known, also not directed to cyclooctanone oxime Process in which nitro hydrocarbons are initially formed from hydrocarbons and nitric acid must be produced, reduced by sulfides or polysulfides whereupon the oximes of the oxidation products of sulphides and polysulphides, especially elemental sulfur, must be laboriously liberated. The procedure is opposite much simpler and yields very much directly from cyclooctane and nitric oxide pure cyclooctanone oxime.
Beispiel Man leitet in 250 g Cyclooktan bei 15 bis 17° unter Belichten mit einer Quecksilbertauchlampe 21/2 Stunden stündlich ein Gemisch aus 750 ccm Chlor und 2250 ccm Stickstoffmonoxyd ein (auf Normalbedingungen berechnet), wobei man für eine möglichst feine und gleichmäßige Verteilung des Gasstromes, z. B. durch Anwendung von Fritten, sorgt. Dann leitet man kurze Zeit Stickstoff durch das Reaktionsgemisch, um überschüssiges Chlor und Stickstoffmonoxyd und. entstandenen Chlorwasserstoff zu entfernen, und saugt den farblosen, aus Cyclooktanonoximhydrochlorid bestehenden Kristallbrei scharf ab. Das Filtrat kann ohne weiteres erneut verwendet werden.EXAMPLE 250 g of cyclooctane are passed through at 15 ° to 17 ° with exposure to light with a mercury immersion lamp for 21/2 hours a mixture every hour from 750 ccm of chlorine and 2250 ccm of nitric oxide (calculated on normal conditions), where for a fine and uniform distribution of the gas flow, z. B. by using frits. Then nitrogen is passed through for a short time the reaction mixture to remove excess chlorine and nitrogen monoxide and. resulting Remove hydrogen chloride and suck the colorless, from cyclooctanone oxime hydrochloride existing crystal pulp. The filtrate can easily be used again will.
Die Kristalle werden in wenig Wasser gelöst, worauf man die Lösung mit Natronlauge neutralisiert. Das Cyclooktanonoxim fällt dabei meistens zunächst ölig aus, erstarrt aber rasch. Es ist völlig farblos und zeigt ohne Umkristallisieren nach dem Trocknen an der Luft bereits den Schmelzpunkt 41 bis 42°. Die Ausbeute beträgt 18 bis 19 g.The crystals are dissolved in a little water, whereupon the solution neutralized with sodium hydroxide solution. The cyclooctanone oxime usually falls first oily, but solidifies quickly. It is completely colorless and shows no recrystallization after drying in the air it already has a melting point of 41 to 42 °. The yield is 18 to 19 g.
Leitet man stündlich ein Gemisch aus 2300 ccm Stickstoffmonoxyd und 570 ccm Chlor ein, so erhält man unter im übrigen gleichen Bedingungen 15 bis 16 g Cyclooktanonoxim, während im Cyclooktan noch kleine Mengen Bis,- (nitrosocyclooktan) und, 1-Chlor-1-nitrosocyclooktan gelöst sind.If one passes hourly a mixture of 2300 ccm of nitrogen monoxide and 570 cc of chlorine, 15 to 16 are obtained under otherwise identical conditions g cyclooctanone oxime, while in the cyclooctane there are still small amounts of bis, - (nitrosocyclooctane) and, 1-chloro-1-nitrosocyclooctane are dissolved.
Die folgende Tabelle zeigt die Abhängigkeit der Oximausbeute vom Molverhältnis
C12: N O unter den oben angegebenen Bedingungen. Es wurden jeweils in 250 g Cyclooktan
21/z Stunden bei 16° unter Belichten stündlich 750 ccm Chlorgas eingeleitet, während
die gleichzeitig eingeleitete Menge Stickstoffmonoxyd bei jedem Versuch geändert
wurde:
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM27935A DE1001982B (en) | 1955-08-09 | 1955-08-09 | Process for the preparation of cyclooctanone oxime |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM27935A DE1001982B (en) | 1955-08-09 | 1955-08-09 | Process for the preparation of cyclooctanone oxime |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1001982B true DE1001982B (en) | 1957-02-07 |
Family
ID=7300254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM27935A Pending DE1001982B (en) | 1955-08-09 | 1955-08-09 | Process for the preparation of cyclooctanone oxime |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1001982B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1095272B (en) | 1959-03-16 | 1960-12-22 | Dr Eugen Mueller | Process for the preparation of cycloaliphatic ketoximes and their hydrochlorides |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE888693C (en) * | 1938-11-29 | 1953-09-03 | Hoechst Ag | Process for the preparation of carbocyclic ketoximes |
| DE898000C (en) * | 1950-12-28 | 1953-11-26 | Chemische Werke Huels Ges Mit | Process for the preparation of cycloaliphatic oximes |
| DE907777C (en) * | 1938-11-29 | 1954-03-29 | Hoechst Ag | Process for the preparation of ketoximes of the cyclohexane series |
| DE927506C (en) * | 1950-03-31 | 1955-05-09 | Der Niederlaendische Staat | Process for the production of oximes by reducing alicyclic nitroparaffins |
-
1955
- 1955-08-09 DE DEM27935A patent/DE1001982B/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE888693C (en) * | 1938-11-29 | 1953-09-03 | Hoechst Ag | Process for the preparation of carbocyclic ketoximes |
| DE907777C (en) * | 1938-11-29 | 1954-03-29 | Hoechst Ag | Process for the preparation of ketoximes of the cyclohexane series |
| DE927506C (en) * | 1950-03-31 | 1955-05-09 | Der Niederlaendische Staat | Process for the production of oximes by reducing alicyclic nitroparaffins |
| DE898000C (en) * | 1950-12-28 | 1953-11-26 | Chemische Werke Huels Ges Mit | Process for the preparation of cycloaliphatic oximes |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1095272B (en) | 1959-03-16 | 1960-12-22 | Dr Eugen Mueller | Process for the preparation of cycloaliphatic ketoximes and their hydrochlorides |
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