DE1175678B - Process for the production of N-cyanlactams - Google Patents
Process for the production of N-cyanlactamsInfo
- Publication number
- DE1175678B DE1175678B DEB66854A DEB0066854A DE1175678B DE 1175678 B DE1175678 B DE 1175678B DE B66854 A DEB66854 A DE B66854A DE B0066854 A DEB0066854 A DE B0066854A DE 1175678 B DE1175678 B DE 1175678B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- lactams
- toluene
- production
- cyanogen
- 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
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000003951 lactams Chemical class 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 235000002639 sodium chloride Nutrition 0.000 description 7
- -1 aromatic N-cyanocarboxamides Chemical class 0.000 description 6
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 5
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VTBOTOBFGSVRMA-UHFFFAOYSA-N 1-Methylcyclohexanol Chemical class CC1(O)CCCCC1 VTBOTOBFGSVRMA-UHFFFAOYSA-N 0.000 description 1
- LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical class CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 description 1
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- CJYXCQLOZNIMFP-UHFFFAOYSA-N azocan-2-one Chemical compound O=C1CCCCCCN1 CJYXCQLOZNIMFP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Internat. KL: C 07 dBoarding school KL: C 07 d
Deutsche KL: 12 ρ - 5German KL: 12 ρ - 5
Nummer: 1175 678Number: 1175 678
Aktenzeichen: B 66854IV d / 12 ρFile number: B 66854IV d / 12 ρ
Anmeldetag: 17. April 1962Filing date: April 17, 1962
Auslegetag: 13. August 1964Opened on: August 13, 1964
Es ist bekannt, aliphatische oder aromatische N-Cyancarbonsäureamide herzustellen, indem man substituierte Cyanamide mit Acylierungsmitteln behandelt (vgl. Houben-Weyl-Müller, Methoden der organischen Chemie, Bd. 8 [1952], S. 177 bis 178).It is known to prepare aliphatic or aromatic N-cyanocarboxamides by substituted cyanamides treated with acylating agents (cf. Houben-Weyl-Müller, methods derorganic chemistry, vol. 8 [1952], pp. 177 to 178).
Es wurde nun gefunden, daß man N-Cyanlactame erhält, wenn man Salze von Lactamen mit 3 bis 11 Methylengruppen im Ring, bei denen die Wasserstoffatome in den Methylengruppen gegebenenfalls durch Alkylgruppen substituiert sind, in Gegenwart von organischen Lösungsmitteln mit Halogencyanen umsetzt.It has now been found that N-cyanolactams are obtained if salts of lactams with 3 to 11 methylene groups in the ring, in which the hydrogen atoms in the methylene groups optionally are substituted by alkyl groups, in the presence of organic solvents with cyanogen halides implements.
Die Methylengruppen können durch eine oder mehrere Alkylgruppen mit z. B. 1 bis 12 Kohlenstoffatomen substituiert sein.The methylene groups can be replaced by one or more alkyl groups with e.g. B. 1 to 12 carbon atoms be substituted.
Als Beispiele für Lactame mit unverzweigten Methylenketten seien genannt: Pyrrolidon-(2), Piperidon - (2), ε- Caprolactam, ζ - Önantholactam, /7-Capryllactam und oj-Laurinlactam. Für Lactame mit Alkylsubstituenten seien die verschiedenen Methyl-g-caprolactame erwähnt, wie man sie rein oder im Gemisch erhält, wenn man Kresole hydriert, die Methylcyclohexanole dehydriert, die dabei entstehenden Methylcyclohexanone oximiert und diese Oxime der Beckmannschen Umlagerung unterwirft.Examples of lactams with unbranched methylene chains are: pyrrolidone- (2), piperidone- (2), ε- caprolactam, ζ - enantholactam, / 7-capryllactam and oj-laurolactam. For lactams with alkyl substituents, mention should be made of the various methyl-g-caprolactams, as they are obtained in pure form or as a mixture when cresols are hydrogenated, the methylcyclohexanols are dehydrogenated, the resulting methylcyclohexanones are oximated and these oximes are subjected to the Beckmann rearrangement.
Die Salze der als Ausgangsmaterial verwendeten Lactame, vorzugsweise die Alkalisalze, lassen sich nach an sich bekannten Methoden herstellen, beispielsweise aus ε-Caprolactam und Natriummetall oder aus Pyrrolidon-(2) und Natriummethylat. Man kann aber auch Erdalkali- oder Erdmetall- oder andere Metallsalze der Lactame verwenden.The salts of the lactams used as starting material, preferably the alkali salts, can be produce by methods known per se, for example from ε-caprolactam and sodium metal or from pyrrolidone- (2) and sodium methylate. But you can also alkaline earth or earth metal or use other metal salts of lactams.
Von den Halogencyanen werden das leicht zugängliche Chlorcyan und das Bromcyan bevorzugt verwendet.Of the cyanogen halides, the readily available cyanogen chloride and cyanogen bromide are preferred used.
Man kann zur Durchführung des Verfahrens entweder das Salz des Lactams in einem inerten Lösungsmittel, z. B. einem aromatischen Kohlenwasserstoff, wie Toluol oder Xylol, oder einem aliphatischen oder cycloaliphatischen Kohlenwasserstoff, suspendieren und das Halogencyan gasförmig, gegebenenfalls unter Druck, einbringen oder in einem Lösungsmittel gelöst eintragen. Es läßt sich aber auch das Halogencyan im Lösungsmittel vorlegen und das Salz des Lactams, gegebenenfalls in Suspension, zugeben. Die Konzentration der Lösungen wird vorteilhaft zwischen 5 und 30% gehalten. Man kann aber auch geringere oder höhere Konzentrationen anwenden.You can carry out the process either the salt of the lactam in an inert Solvents, e.g. B. an aromatic hydrocarbon such as toluene or xylene, or an aliphatic or cycloaliphatic hydrocarbon, suspend and the cyanogen halide in gaseous form, if necessary under pressure, introduce or enter dissolved in a solvent. It can be but also submit the cyanogen halide in the solvent and the lactam salt, optionally in Suspension, admit. The concentration of the solutions is advantageously kept between 5 and 30%. But you can also use lower or higher concentrations.
Zweckmäßigerweise wird das Verfahren bei niedriger Temperatur, vorzugsweise bei —10 bis +50° C, durchgeführt.Conveniently, the process is carried out at low temperature, preferably at -10 to + 50 ° C.
Verfahren zur Herstellung von N-CyanlactamenProcess for the production of N-cyanolactams
Anmelder:Applicant:
Badische Anilin- & Soda-FabrikAniline & Soda Factory in Baden
Aktiengesellschaft, Ludwigshafen/RheinAktiengesellschaft, Ludwigshafen / Rhein
Als Erfinder benannt:Named as inventor:
Dr. Robert Gehm, Ludwigshafen/Rhein,Dr. Robert Gehm, Ludwigshafen / Rhine,
Dr. Gustav Steinbrunn, Schwegenheim (Pfalz),Dr. Gustav Steinbrunn, Schwegenheim (Palatinate),
Dr. Friedrich Bayerlein, Frankenthal,Dr. Friedrich Bayerlein, Frankenthal,
Dr. Günter Becht, Speyer,Dr. Günter Becht, Speyer,
Dr. Hans Wilhelm, Ludwigshafen/RheinDr. Hans Wilhelm, Ludwigshafen / Rhine
Die Lactame werden nach dem Abfiltrieren des ausgefallenen Niederschlags, der im wesentlichen aus anorganischem Metallhalogenid besteht, aus der Lösung gewonnen. Sie sind zum Teil destillierbare Flüssigkeiten oder ölige bis kristalline Substanzen.The lactams are after filtering off the precipitated precipitate, which essentially consists of inorganic metal halide is obtained from the solution. Some of them can be distilled Liquids or oily to crystalline substances.
Die neuen N-Cyanlactame stellen wertvolle Zwischenprodukte dar, z. B. zur Herstellung von Schädlingsbekämpfungsmitteln und Pharmazeutika. Sie sind aber auch unmittelbar als Fungizide, Herbizide und Insektizide verwendbar.The new N-cyanolactams are valuable intermediates, e.g. B. for the manufacture of pesticides and pharmaceuticals. But they can also be used directly as fungicides, herbicides and insecticides.
In einer Rührapparatur werden 21 Teile Bromcyan in 50 Teilen Toluol gelöst und auf 0 bis +50C abgekühlt. Man trägt im Laufe von einer Stunde 25 Teile Pyrrolidon-(2)-Kalium in 100 Teilen Toluol suspendiert ein und läßt anschließend die Reaktionstemperatur auf 30° C ansteigen. Nach dem Absaugen des unlöslichen Rückstandes, der in der Hauptsache aus Kaliumchlorid besteht, erhält man aus dem Filtrat 12 Teile rohes N-Cyanpyrrolidon-(2), aus dem sich durch Destillation 10 Teile der reinen Verbindung mit dem Kp.25 130 bis 132° C als wasserhelle Flüssigkeit gewinnen lassen.In a stirring apparatus, 21 parts of cyanogen bromide are dissolved in 50 parts of toluene and cooled to 0 to +5 0 C. 25 parts of pyrrolidone (2) potassium are suspended in 100 parts of toluene over the course of one hour and the reaction temperature is then allowed to rise to 30.degree. After suctioning off the insoluble residue, which consists mainly of potassium chloride, 12 parts of crude N-cyanopyrrolidone- (2) are obtained from the filtrate, from which 10 parts of the pure compound with the b.p. 25 130 to 132 ° are obtained by distillation Allow C to be obtained as a water-white liquid.
25 Teile Pyrrolidon-(2)-Kalium werden in 100 Teilen Toluol suspendiert, und in diese Suspension werden bei —10 bis ± 0° C 12 g gasförmiges Chlorcyan eingeleitet. Bei der Aufarbeitung erhält man das N-Cyanpyrrolidon-(2) in derselben Ausbeute wie bei Beispiel 1.25 parts of pyrrolidone (2) potassium are suspended in 100 parts of toluene, and in this suspension become 12 g of gaseous cyanogen chloride at -10 to ± 0 ° C initiated. Working up gives the N-cyanopyrrolidone- (2) in the same yield as in example 1.
409 640/406409 640/406
Man legt wie im Beispiel 1 12 Teile Chlorcyan in 100 Teilen Toluol vor und kühlt auf 0° C ab. Sodann trägt man 27 Teile s-Caprolactam-Natrium, das man in 100 Teilen Toluol suspendiert hat, langsam innerhalb einer Stunde ein. Die Temperatur steigt dabei auf +20° C. Es entsteht ein Niederschlag (Kochsalz und Nebenprodukte), der vom Toluol abgetrennt wird. Aus dem Filtrat lassen sich 18 Teile rohes N-Cyan-i-caprolactam gewinnen, das durch Destillation gereinigt wird. Der Siedepunkt des wasserklaren, kristallisierenden Öles beträgt bei 0,3 Torr 136 bis 138° C. F. 38 bis 40° C.As in Example 1, 12 parts of cyanogen chloride in 100 parts of toluene are initially taken and the mixture is cooled to 0.degree. Then 27 parts of sodium s-caprolactam, which has been suspended in 100 parts of toluene, are carried slowly within an hour. The temperature rises to + 20 ° C. A precipitate is formed (Table salt and by-products), which is separated from the toluene. Eighteen parts can be made from the filtrate Obtain crude N-cyano-i-caprolactam, which is purified by distillation. The boiling point of the water-clear, crystallizing oil is at 0.3 Torr 136 to 138 ° C. F. 38 to 40 ° C.
Man legt entsprechend Beispiel 3 31 Teile Chlorcyan in 100 Teilen Toluol vor und kühlt auf 0° C ab. Sodann trägt man eine Suspension von 81 Teilen jj-Capryllactam-Natrium in 500 Teilen Toluol innerhalb einer Stunde ein, wobei die Temperatur auf Zimmertemperatur ansteigt. Der entstehende Niederschlag, der aus Kochsalz und Nebenprodukten besteht, wird abgetrennt. Aus dem Filtrat werden durch Destillation bei 0,3 Torr und 123 bis 130° C 28 Teile N-Cyan-^-capryllactam in Form eines dickflüssigen Öles, das langsam erstarrt, erhalten. F. 60° C.As in Example 3, 31 parts of cyanogen chloride in 100 parts of toluene are initially taken and the mixture is cooled to 0.degree. A suspension of 81 parts of i-capryllactam sodium in 500 parts of toluene is then carried within one hour, during which the temperature rises to room temperature. The resulting precipitation, which consists of table salt and by-products is separated. From the filtrate are through Distillation at 0.3 Torr and 123 to 130 ° C 28 parts of N-cyano - ^ - capryllactam in the form of a viscous Obtain oil that slowly solidifies. F. 60 ° C.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB66854A DE1175678B (en) | 1962-04-17 | 1962-04-17 | Process for the production of N-cyanlactams |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB66854A DE1175678B (en) | 1962-04-17 | 1962-04-17 | Process for the production of N-cyanlactams |
| FR931750A FR1353439A (en) | 1963-04-17 | 1963-04-17 | Process for the production of cyclic n-cyanamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1175678B true DE1175678B (en) | 1964-08-13 |
Family
ID=25966221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB66854A Pending DE1175678B (en) | 1962-04-17 | 1962-04-17 | Process for the production of N-cyanlactams |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1175678B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1219711B (en) | 1964-02-27 | 1966-06-23 | Sick Erwin | Lens wheel arrangement |
| EP0049688A1 (en) * | 1980-10-07 | 1982-04-14 | Ciba-Geigy Ag | Process for preparing N-cyanolactames |
-
1962
- 1962-04-17 DE DEB66854A patent/DE1175678B/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1219711B (en) | 1964-02-27 | 1966-06-23 | Sick Erwin | Lens wheel arrangement |
| EP0049688A1 (en) * | 1980-10-07 | 1982-04-14 | Ciba-Geigy Ag | Process for preparing N-cyanolactames |
| US4356121A (en) * | 1980-10-07 | 1982-10-26 | Ciba-Geigy Corporation | Process for the production of N-cyanolactams |
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