DE878641C - Process for the production of higher molecular amines - Google Patents
Process for the production of higher molecular aminesInfo
- Publication number
- DE878641C DE878641C DET3000D DET0003000D DE878641C DE 878641 C DE878641 C DE 878641C DE T3000 D DET3000 D DE T3000D DE T0003000 D DET0003000 D DE T0003000D DE 878641 C DE878641 C DE 878641C
- Authority
- DE
- Germany
- Prior art keywords
- amines
- hydrogenation
- unsaturated
- higher molecular
- production
- 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.)
- Expired
Links
- 150000001412 amines Chemical class 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 17
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 8
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000001476 alcoholic effect Effects 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- FQMNVNKBWNEVMK-UHFFFAOYSA-J barium(2+);platinum(2+);disulfate Chemical compound [Ba+2].[Pt+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O FQMNVNKBWNEVMK-UHFFFAOYSA-J 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- -1 carbonyl compounds amines Chemical class 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 101150114464 ATRN gene Proteins 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- CEBSMELBIRTTBF-UHFFFAOYSA-N azane;n-propan-2-ylpropan-2-amine Chemical compound N.CC(C)NC(C)C CEBSMELBIRTTBF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- TXTHKGMZDDTZFD-UHFFFAOYSA-N n-cyclohexylaniline Chemical compound C1CCCCC1NC1=CC=CC=C1 TXTHKGMZDDTZFD-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229940053973 novocaine Drugs 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von höhermolekularen Aminen Es ist bekannt, durch Hydrierung von Carbonylverbindungen in Gegenwart von Ammoniak bzw. seinen Derivaten substituierte Amine herzustellen. So liefert z. B. bei Raumtemperatur die Hydrierung des Acetons in Gegenwart von Ammoniak das Di-isopropylamin; der Benzaldehyd wird bei der Hydrierung in Gegenwart von Dimethylamin zum N-Dimethylbenzylamin reduziert, und das Cyclohexanon liefert bei der Hydrierung in Gegenwart von Anilin das N-Phenylcyclohexylamin.Process for the preparation of higher molecular weight amines It is known by hydrogenation of carbonyl compounds in the presence of ammonia or its Derivatives to produce substituted amines. For example, B. at room temperature the hydrogenation of acetone in the presence of ammonia di-isopropylamine; the benzaldehyde is reduced to N-dimethylbenzylamine during the hydrogenation in the presence of dimethylamine, and the cyclohexanone gives the N-phenylcyclohexylamine on hydrogenation in the presence of aniline.
Weiter ist es bekannt, die aus ungesättigten Aldehyden und primären Aminen erhältlichen Schiffschen Basen durch katalytische Hydrierung in gesättigte Amine zu überführen. Schließlich ist es bekannt, daß Iminoverbindungen, die außer der ungesättigten Iminogruppe eine einzelne Äthylendoppelbindung enthalten, durch Reduktion in einfach ungesättigte Amine übergeführt werden können.It is also known that from unsaturated aldehydes and primary Amines available Schiff's bases by catalytic hydrogenation into saturated To convert amines. Finally, it is known that imino compounds that except of the unsaturated imino group contain a single ethylene double bond through Reduction can be converted into monounsaturated amines.
Eine besonders leicht zugängliche Klasse von ungesättigten Carbonylverbindungen sind diejenigen, die, wie z. B. das jonon oder das Pseudojonon, außer der Carbonylgruppe noch mehrere C, C-Doppelbindungen enthalten. Es wurde nun gefunden, daß man diese höhermolekularen, mehrfach ungesättigten Carbonylverbindungen dadurch in ungesättigte Amine überführen kann, daß man sie in Gegenwart von Aminen der partiellen Hydrierung unterwirft. Die Maßnahmen zur Durchführung einer partiellen Hydrierung sind an sich bekannt (Abderhalden, Handbuch der biologischen Arbeitsmethoden, Abt. z, Teil 12, S. 132 und I33). Es war jedoch keineswegs vorauszusehen, ob bei der nicht vollständig.durchgeführten Hydrierung dieser mehrfach ungesättigten Carbonylverbindungen überhaupt Amine entstehen würden. Denn in dem einzigen Fall, in dem im Schrifttum der Versuch zur Überführung einer mehrfach ungesättigten Carbonylverbindung durch partielle Hydrierung in ein ungesättigtes Amin beschrieben ist, nämlich bei der partiellen Hydrierung des Pseudojonons in Gegenwart.'von Ammoniak (vgl. Dissertation von Keil, Hannover, I928, S. 23), ist bekanntgeworden, daß hierbei überhaupt keine basischen Produkte erhalten werden.A particularly accessible class of unsaturated carbonyl compounds are those who, such as B. the jonon or the pseudojonon, except for the carbonyl group still contain several C, C double bonds. It has now been found that you can do this higher molecular weight, polyunsaturated carbonyl compounds are converted into unsaturated ones Amines can be converted by partial hydrogenation in the presence of amines subject. The measures for carrying out a partial hydrogenation are inherent known (Abderhalden, Handbook of Biological Working Methods, Dept. z, Part 12, P. 132 and I33). However, it was by no means foreseeable whether at the incomplete hydrogenation of these polyunsaturated carbonyl compounds amines would arise at all. Because in the only case in the literature the attempt to convert a polyunsaturated carbonyl compound by partial hydrogenation is described in an unsaturated amine, namely in the partial hydrogenation of the pseudoionon in the presence of ammonia (see dissertation von Keil, Hanover, 1928, p. 23), it has become known that here none at all basic products are obtained.
Es war daher überraschend, daß es gelingt, mehrfach ungesättigte Carbonylverbindungen, die andere gegen katalytische Hydrierung empfindliche Gruppen nicht enthalten, durch partielle Hydrierung in Gegenwart von Aminen in ungesättigte Amine zu überführen, in denen ein, Teil der den ungesättigten Carbonylverbindungen entstammenden C, C-Doppelbindungen abgesättigt ist.It was therefore surprising that polyunsaturated carbonyl compounds, which do not contain other groups sensitive to catalytic hydrogenation to convert partial hydrogenation in the presence of amines into unsaturated amines, in which some of the C, C double bonds originating from the unsaturated carbonyl compounds is saturated.
Die auf. diese Weise nunmehr leicht zugänglichen, höhermolekularen ungesättigten Amine besitzen wertvolle therapeutische Eigenschaften und sind z. B. vielfach den bekannten niedrigermolekularen Verbindungen ähnlicher Konstitution in ihrer Wirksamkeit überlegen. So sind die gemäß den Beispielen hergestellten höhermolekularen ungesättigten Amine nicht nur etwa 2omal so stark spasmolytisch wirksam wie das Methylamino-6-methyl-2-hepten-2, sondern sie zeigen darüber hinaus am isolierten Froschnerven eine 2o- bis 3omal so starke anästhesierende Wirkung wie das Cocain bzw. Novocain. Diese für ein Infiltrationsanästheticum außerordentlich-günstige Wirkungsweise ist dagegen bei dem Methylamino-6-methyl-2-hepten-2 nicht vorhanden. Beispiel i o,i Mol 2, 6-Dimethyl-undecatrien-(2, 6, 8)-on-(io) wird in 50 ccm Äthylalkohol gelöst und mit einer 25o/oigen alkoholischen Lösung von o,2 Mol Methylamin versetzt. Nach Zugabe von i ccm gesättigter, alkoholischer Salzsäurelösung werden-i» g Pt-Ba S 04-Katalysator, entsprechend i g Platin, hinzugefügt. Die Aktivität des Katalysators wird vor der Anwendung durch längeres Schütteln mit Wasserstoff in basischen Medien verringert. Die Hydrierung des ungesättigten Ketons in Gegenwart von Methylamin erfolgt zunächst bei Raumtemperatur und 3 Atrn. Überdruck. Während der Hydrierung erwärmt sich jedoch das Reaktionsgemisch infolge Auftretens von Reaktionswärme. Nach Aufnahme der für 3 Mol entsprechenden Menge Wasserstoff von 7,1 1 kommt die Hydrierung zum Stillstand. Zur vollständigen Absättigung aller Doppelbindungen wäre die Aufnahme von 4 Mol Wasserstoff erforderlich gewesen. Aus dem Filtrat vom Katalysator wird eine ungesättigte Base isoliert, die bei 3 mm bei 13o° destilliert. Die Titration mit n-Schwefelsäure ergibt, daß das 2, 6-Dimethylio-methylamino-undecen-8 vorliegt. Die Ausbeute beträgt etwa 8o °/o des angewandten Ketons.The on. this way now easily accessible, higher molecular weight unsaturated amines have valuable therapeutic properties and are z. B. in many cases superior to the known lower molecular weight compounds of similar constitution in their effectiveness. The higher molecular weight unsaturated amines produced according to the examples are not only about 20 times as strong spasmolytic as methylamino-6-methyl-2-hepten-2, but they also show an anesthetic effect on isolated frog nerves that is 20 to 3 times as strong as the cocaine or novocaine. This mode of action, which is extraordinarily favorable for an infiltration anesthetic, is not present in the case of methylamino-6-methyl-2-hepten-2. Example io, i mol of 2,6-dimethyl-undecatrien- (2, 6, 8) -one- (io) is dissolved in 50 cc of ethyl alcohol and mixed with a 25% alcoholic solution of 0.2 mol of methylamine. After adding 1 cc of saturated, alcoholic hydrochloric acid solution, 1 »g of Pt-Ba S 04 catalyst, corresponding to platinum, are added. The activity of the catalyst is reduced by prolonged shaking with hydrogen in basic media before use. The hydrogenation of the unsaturated ketone in the presence of methylamine is initially carried out at room temperature and 3 Atrn. Overpressure. During the hydrogenation, however, the reaction mixture heats up due to the occurrence of heat of reaction. When the amount of hydrogen of 7.1 l corresponding to 3 moles of hydrogen has been taken up, the hydrogenation comes to a standstill. The uptake of 4 mol of hydrogen would have been necessary for complete saturation of all double bonds. An unsaturated base is isolated from the filtrate from the catalyst and distilled at 130 ° at 3 mm. The titration with n-sulfuric acid shows that the 2,6-dimethylio-methylamino-undecen-8 is present. The yield is about 80% of the ketone used.
Beispiel 2 2o g frisch destilliertes jonon vom Kp" 134 bis I35° «'erden in 5o ccm Alkohol gelöst und nach Zusatz .von 27 ccm 23o/oiger alkoholischer Methylaminlösung sowie 17 g eines bereits mehrfach verwendeten Platin-Bariumsulfat-Katalysa.tors, der vorher längere Zeit mit Wasserstoff und Aminen geschüttelt war, bei Raumtemperatur und 3 Atm. der katalytischen Hydrierung unterworfen. Die Hydrierung kommt zum Stillstand, nachdem 3,5 1 Wasserstoff aufgenommen sind; die zur Absättigung sämtlicher Doppelbindungen erforderliche Menge Wasserstoff beträgt 7,5 1. Das Filtrat vom Katalysator wird im Vakuum vom Alkohol befreit. Der Rückstand wird, nachdem er im Vakuum destilliert ist, in verdünnter Schwefelsäure gelöst. Die Lösung wird zwecks Entfernung nicht basischer Bestandteile mehrfach ausgeäthert. Aus der schwefelsauren Lösung wird mit 3oo/oiger Natronlauge das ungesättigte Amin in Freiheit gesetzt. Es siedet bei 3 mm von 92 bis 93°. Die Lösungen der mineralsauren Salze dieser Base schäumen stark. Die Ausbeute beträgt etwa 7o oio des angewendeten Ketons. Beispiel 3 45 Teile Citral werden in 5o Teilen Alkohol gelöst und nach Zusatz von 4o Teilen etwa 2oo/oiger alkoholischer Methylaminlösung, der i ccm 2oo/oige alkoholische Salzsäure hinzugesetzt ist, sowie 12 g eines Platin-Bariumsulfat-Katalysators bei Raumtemperatur und 3 Atm. der Hydrierung unterworfen. Nach Absorption der für 2 Mol berechneten Menge Wasserstoff kommt die Hydrierung zum Stillstand; der Katalysator wird abfiltriert und mit Alkohol und Äther gewaschen. Nach Ansäuern wird im Vakuum eingedampft. Der Rückstand wird in Wasser aufgenommen und mit Äther gewaschen. Auf Zusatz von Alkali wird eine Base erhalten, die durch fraktionierte Destillation im Vakuum gereinigt wird. Bei 2 mm geht in einer Menge von etwa 70 °/o zwischen 73 und 74° das N-Methyl-3, 7-dimethyloctenylamin über.Example 2 20 g of freshly distilled jonon with a bp of 134 to 135 ° ground dissolved in 50 cc of alcohol and, after the addition of 27 cc of 23o per cent alcoholic methylamine solution and 17 g of a platinum-barium sulfate catalyst that has already been used several times, the was previously shaken with hydrogen and amines for a long time, subjected to catalytic hydrogenation at room temperature and 3 atmospheres. The hydrogenation comes to a standstill after 3.5 liters of hydrogen have been absorbed; the amount of hydrogen required to saturate all double bonds is 7.5 liters. The filtrate from the catalyst is freed from alcohol in vacuo. The residue, after it has been distilled in vacuo, is dissolved in dilute sulfuric acid. The solution is repeatedly extracted with ether to remove non-basic constituents. The unsaturated solution is obtained from the sulfuric acid solution with 300% sodium hydroxide solution Amine set free, boiling at 3 mm from 92 ° to 93 ° C. The solutions of the mineral acid salts of this base foam n strong. The yield is about 70,000 of the ketone used. Example 3 45 parts of citral are dissolved in 50 parts of alcohol and, after the addition of 40 parts, about 2oo% alcoholic methylamine solution to which 1 ccm of 2oo% alcoholic hydrochloric acid has been added, and 12 g of a platinum-barium sulfate catalyst at room temperature and 3 atmospheres. subjected to hydrogenation. After the amount of hydrogen calculated for 2 moles has been absorbed, the hydrogenation comes to a standstill; the catalyst is filtered off and washed with alcohol and ether. After acidification, it is evaporated in vacuo. The residue is taken up in water and washed with ether. The addition of alkali gives a base which is purified by fractional distillation in vacuo. At 2 mm, the N-methyl-3, 7-dimethyloctenylamine passes over in an amount of about 70% between 73 and 74 °.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET3000D DE878641C (en) | 1936-09-16 | 1936-09-16 | Process for the production of higher molecular amines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET3000D DE878641C (en) | 1936-09-16 | 1936-09-16 | Process for the production of higher molecular amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE878641C true DE878641C (en) | 1953-06-05 |
Family
ID=7544151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DET3000D Expired DE878641C (en) | 1936-09-16 | 1936-09-16 | Process for the production of higher molecular amines |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE878641C (en) |
-
1936
- 1936-09-16 DE DET3000D patent/DE878641C/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE878641C (en) | Process for the production of higher molecular amines | |
| DE1014089B (en) | Process for the preparation of 2,2-dimethylpropanediol- (1,3) | |
| DE2813162C3 (en) | Process for the preparation of N-methylpyrrolidine | |
| DE959825C (en) | Process for the preparation of 2, 3-dihydro-enzo-1, 3-oxazonen- (4) endocyclically substituted | |
| DE3020298C2 (en) | Process for the preparation of 2,2,4,5,5-pentamethyl-3-formyl-3-pyrroline | |
| DE2357346A1 (en) | 3-ALKYLAMINO-4-HYDROXY-ALPHA-AMINOMETHYLBENZYL ALCOHOLS, THEIR SALT, METHOD FOR THEIR MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS | |
| DE617596C (en) | Process for the preparation of secondary and tertiary unsaturated amines | |
| DE863189C (en) | Process for the preparation of butanetriol- (1,2,4) | |
| DE892893C (en) | Process for the production of carboxylic acid esters | |
| DE962333C (en) | Process for the preparation of cyclohexanone oxime | |
| DE1275042B (en) | Process for the production of saturated alcohols and carbonyl compounds | |
| DE2940256A1 (en) | N, N-DIMETHYL-N '- (BETA) -HYDROXYETHYL-PROPYLENE DIAMINE AND METHOD FOR PRODUCING THE SAME | |
| DE1215729B (en) | Process for the production of new bis-alkanolamine derivatives and their salts | |
| DE949654C (en) | Process for the production of acrylic acid and its functional derivatives | |
| AT117860B (en) | Process for the production of carbocyclic ketones with more than nine ring members. | |
| AT288394B (en) | Process for the preparation of new cinnamic acid amides | |
| CH253163A (en) | Process for the selective hydrogenation of organic compounds with a triple C-C bond in the gaseous phase to form compounds with a double C-C bond. | |
| AT230882B (en) | Process for the production of 6-aminochryses | |
| AT164547B (en) | Process for the production of vitamin B1 | |
| DE892447C (en) | Process for the preparation of dicyclohexyl ethane compounds | |
| AT205018B (en) | Process for cleaning acrylonitrile contaminated in particular with methyl vinyl ketone and acetaldehyde | |
| DE815043C (en) | Process for the preparation of derivatives of 1- (p-oxyphenyl) -2-aminopropanols- (1) | |
| DE825551C (en) | Process for the preparation of 1-ephedrine and its salts | |
| AT260438B (en) | Process for the production of new 14α-hydroxysteroids | |
| AT142359B (en) | Process for the production of hydrogenation products of the follicular hormones obtained from animal or vegetable material or synthetically. |