DE881946C - Process for the preparation of monoacyl derivatives of 1,2-alkylenediamines - Google Patents
Process for the preparation of monoacyl derivatives of 1,2-alkylenediaminesInfo
- Publication number
- DE881946C DE881946C DEB4481A DEB0004481A DE881946C DE 881946 C DE881946 C DE 881946C DE B4481 A DEB4481 A DE B4481A DE B0004481 A DEB0004481 A DE B0004481A DE 881946 C DE881946 C DE 881946C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- radical
- molecular weight
- hydrogen
- alkylenediamines
- 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
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000003141 primary amines Chemical class 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- -1 methyl- Chemical group 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OTGQIQQTPXJQRG-UHFFFAOYSA-N N-(octadecanoyl)ethanolamine Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCO OTGQIQQTPXJQRG-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical class C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
- PMUNIMVZCACZBB-UHFFFAOYSA-N 2-hydroxyethylazanium;chloride Chemical compound Cl.NCCO PMUNIMVZCACZBB-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- HAAZMOAXEMIBAJ-UHFFFAOYSA-N 4-chloro-2-methylquinazoline Chemical compound C1=CC=CC2=NC(C)=NC(Cl)=C21 HAAZMOAXEMIBAJ-UHFFFAOYSA-N 0.000 description 1
- DDUHZTYCFQRHIY-UHFFFAOYSA-N 7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione Chemical compound COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- GCGYREODZIZPLJ-UHFFFAOYSA-N azepan-1-ium;chloride Chemical compound Cl.C1CCCNCC1 GCGYREODZIZPLJ-UHFFFAOYSA-N 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- VJLOFJZWUDZJBX-UHFFFAOYSA-N bis(2-hydroxyethyl)azanium;chloride Chemical compound [Cl-].OCC[NH2+]CCO VJLOFJZWUDZJBX-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- BOWVQLFMWHZBEF-KTKRTIGZSA-N oleoyl ethanolamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCCO BOWVQLFMWHZBEF-KTKRTIGZSA-N 0.000 description 1
- 239000011022 opal Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Birds (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Paper (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Monoacylderivaten von 1, 2-Alkylendiaminen Es wurde gefunden, daB man wertvolle Derivate von i, 2-Alkylendiaminen der allgemeinen Formel worin R1 einen organischen Rest mit mindestens 3 C-Atomen, R2 Wasserstoff, einen niedrigmolekularen Alkyl- oder Oxyalkylrest, R3 Wasserstoff oder einen niedrigmolekularen Alkylrest, R4 einen gegebenenfalls substituierten Alkyl-, Aryl- oder Cycloalkylrest, R6 Wasserstoff oder einen Alkylrest bedeuten und gegebenenfalls R4 und R5 unter Ringbildung verbunden sind, erhält, wenn man x, 2-Alkanolamide höhermolekularer Carbonsäuren der Formel R1C0-N(R2)-CH2-CH(R3)OH mit Salzen aus primären oder sekundären Aminen HN (R4) R6 und starken anorganischen Säuren auf 16o bis 25o°, vorzugsweise i8o bis 22o°, erhitzt, wobei unter R1, R2, R3, R4 und R5 die oben bezeichneten Atome bzw. Reste zu verstehen sind.Process for the preparation of monoacyl derivatives of 1,2-alkylenediamines It has been found that valuable derivatives of 1,2-alkylenediamines of the general formula can be obtained where R1 is an organic radical with at least 3 carbon atoms, R2 is hydrogen, a low molecular weight alkyl or oxyalkyl radical, R3 is hydrogen or a low molecular weight alkyl radical, R4 is an optionally substituted alkyl, aryl or cycloalkyl radical, R6 is hydrogen or an alkyl radical and optionally R4 and R5 are connected to form a ring, if x, 2-alkanolamides of higher molecular weight carboxylic acids of the formula R1C0-N (R2) -CH2-CH (R3) OH with salts of primary or secondary amines HN (R4) R6 and strong inorganic acids are obtained heated to 16o to 25o °, preferably 18o to 22o °, where R1, R2, R3, R4 and R5 are to be understood as meaning the atoms or radicals indicated above.
Als i, 2-Alkanolamide höhermolekularer Carbonsäuren eignen sich z. B. die Amide aus natürlichen oder synthetischen Fettsäuren, wie Buttersäure, Capronsäure, Laurinsäure, Palmitinsäure, Stearinsäure, Ölsäure, Ricinolsäure, Paraffincarbonsäuren oder Naphthensäuren, Benzoesäure, Salicylsäure, Phthalsäure, Naphthalincarbonsäuren u. dgl. und z, 2-Oxyalkylaminen, wie Mono- und Diäthanolamin, Methyl-, Äthyl-, Butyläthanolamin, r, 2-Mono- und -Dipropanolamin, Methyl-r, 2-propanolamin, z, 2-Butanolamin usw. Für die Umsetzung mit den z,- 2-Alkanolamiden geeignete Salze von primären oder sekundären Aminen sind beispielsweise die Sulfate, Chlorhydrate oder Phosphate von Monopropylamin, Dibutylamin, Dodecylamin, Mono- oder Diäthanolamin, z, 3-Butanolamin, Äthylpropanolamin, Cyclohexylamin, Anilin, Toluidin, Piperidin oder Hexamethylenimin usw.As i, 2-alkanolamides of higher molecular weight carboxylic acids, for. B. the amides from natural or synthetic fatty acids, such as butyric acid, caproic acid, Lauric acid, palmitic acid, stearic acid, oleic acid, ricinoleic acid, paraffin carboxylic acids or naphthenic acids, benzoic acid, salicylic acid, phthalic acid, Naphthalenecarboxylic acids and the like and z, 2-oxyalkylamines, such as mono- and diethanolamine, methyl-, ethyl-, butylethanolamine, r, 2-mono- and -dipropanolamine, methyl-r, 2-propanolamine, z, 2-butanolamine, etc. For the reaction with the z, - 2-alkanolamides suitable salts of primary or secondary amines are, for example, the sulfates, chlorohydrates or phosphates of Monopropylamine, dibutylamine, dodecylamine, mono- or diethanolamine, z, 3-butanolamine, Ethylpropanolamine, cyclohexylamine, aniline, toluidine, piperidine or hexamethyleneimine etc.
Die Reaktionskomponenten werden vorzugsweise in äquimolekularen Mengen umgesetzt, jedoch ist auch ein nicht zu großer Überschuß der einen oder anderen Komponente, z. B. des Aminsalzes, anwendbar. Die Umsetzung vollzieht sich bei den oberhalb 16o° liegenden Temperaturen unter Austritt von Z Molekül Wasser. Gegebenenfalls kann unter Anwendung von vermindertem Druck oder wasserentziehenden Mitteln gearbeitet werden. Die erhaltenen kondensationsprodukte sind j e nach dem Ausgangsmaterial im allgemeinen feste bis pastenförmige, wachsartige Massen, die sich in Wasser klar oder mit schwacher Trübung lösen. Durch Umsetzung mit Alkali oder den Alkahsalzen schwacher Säuren, wie Natriumacetat, lassen sich daraus die freien Basen bzw. die Salze mit schwachen Säuren gewinnen.The reaction components are preferably used in equimolecular amounts implemented, but there is also a not too great excess of one or the other Component, e.g. B. the amine salt, applicable. The implementation takes place at the Temperatures above 160 ° with the escape of Z molecule water. Possibly can be carried out using reduced pressure or dehydrating agents will. The condensation products obtained depend on the starting material generally solid to pasty, waxy masses that clear in water or dissolve with weak cloudiness. By reaction with alkali or the alkali salts weak acids such as sodium acetate, the free bases or the Obtain salts with weak acids.
Die erhaltenen Kondensationsprodukte können als Hilfsmittel für die Textil-, Leder- oder Papierindustrie oder als Ausgangsmaterial zur Herstellung solcher Mittel dienen.The condensation products obtained can be used as an aid for Textile, leather or paper industry or as a starting material for the production of such Serving means.
Die in den nachstehenden Beispielen angegebenen Teile sind Gewichtsteile. Beispiel r Man erhitzt 243 Teile Kokosfettsäureäthanolamid mit rzo Teilen Butyläminhydrochlorid 2 Stunden auf etwa 22o°. Dabei destillieren Wasser und etwas Amin ab. Das erhaltene Produkt ist eine vaselinartige Masse, die in Wasser mit schwacher Opalessenz löslich ist. Beispiel 2 Man erhitzt 325 Teile Ölsäuremonoäthanolamid mit 136 Teilen Cyclohexylaminhydrochlorid 2 Stunden auf etwa 22o°. Es destillieren dabei Wasser und etwas Amin ab. Das erhaltene Produkt ist eine weiche, helle Masse, die sich in Wasser klar löst -und sich nsbesondere durch gute Netzwirkung auszeichnet. Beispiel 3 327 Teile Stearinsäuremonoäthanolamid und 97 Teile Monoäthanolaminhydrochlorid werden miteinander gemischt und -2 Stunden- auf 22o°- erhitzt. Das erhaltene Produkt wird in geschmolzenem Zustand mit einer Lösung von 82-Teilen Natriumacetat in Zoo Teilen Wasser verrührt. Die erhaltene Verbindung stellt eine gelblichweiße, wachsartige Masse dar, die vorzügliche weichmachende Eigenschaften besitzt. Beispiel 4 327 Teile Stearinsäuremonoäthanolamid und 136 Teile Hexamethyleniminhydrochlorid werden 2 Stunden auf Zoo bis 22o° erhitzt. Das Reaktionsprodukt wird in 5oo Teilen Wasser gelöst und mit 8o Teilen 5o°Joiger Natronlauge versetzt. Das ausgeschiedene freie Amin führt man durch Umsetzung mit 6o Teilen Essigsäure in das Acetat über. Dieses stellt eine wachsartige Masse dar, die sich gut als Weichmachungsmittel eignet.The parts given in the examples below are parts by weight. EXAMPLE 243 parts of coconut fatty acid ethanol amide with 10 parts of butylamine hydrochloride are heated to about 220 ° for 2 hours. In the process, water and some amine distill off. The product obtained is a vaseline-like mass that is soluble in water with a weak opal essence. Example 2 325 parts of oleic acid monoethanolamide are heated with 136 parts of cyclohexylamine hydrochloride to about 220 ° for 2 hours. Water and some amine are distilled off in the process. The product obtained is a soft, light-colored mass that dissolves clearly in water - and is particularly notable for its good wetting effect. Example 3 327 parts of stearic acid monoethanolamide and 97 parts of monoethanolamine hydrochloride are mixed with one another and heated to 220 ° for -2 hours. The product obtained is stirred in the molten state with a solution of 82 parts of sodium acetate in zoo parts of water. The compound obtained is a yellowish-white, waxy mass which has excellent plasticizing properties. Example 4 327 parts of stearic acid monoethanolamide and 136 parts of hexamethyleneimine hydrochloride are heated to a temperature of 220 ° for 2 hours. The reaction product is dissolved in 500 parts of water and 80 parts of 50 ° Joiger sodium hydroxide solution are added. The precipitated free amine is converted into the acetate by reaction with 60 parts of acetic acid. This is a waxy mass that is well suited as a plasticizer.
Beispiel 5 ,34= Teile Ölsäure-z, 2-propanolamid werden mit =42 Teilen Diäthanolaminhydrochlorid 2 Stunden auf 22o° erhitzt. Das Reaktionsprodukt wird in geschmolzenem Zustand mit einer Lösung von 82 Teilen Natriumacetat in Zoo Teilen Wasser langsam verrührt. Das erhaltene.Acetat besitzt eine hohe Netzwirkung. Beispiel 6 343 Teile Stearinsäure-N-methylmonoäthanolamid werden mit 129 Teilen Anilinhydrochlorid 2 Stunden auf 22o° erhitzt. Das erhaltene Produkt wird in geschmolzenem Zustand mit einer Lösung von 82 Teilen Natriumacetat in Zoo Teilen Wasser verrührt. Man erhält eine weißlichgelbe, ziemlich feste Masse, die guten Weichmachungseffekt zeigt.Example 5, 34 = parts of oleic acid-z, 2-propanolamide are with = 42 parts Diethanolamine hydrochloride heated to 220 ° for 2 hours. The reaction product will in the molten state with a solution of 82 parts of sodium acetate in zoo parts Mix water slowly. The acetate obtained has a high wetting effect. example 6,343 parts of stearic acid-N-methylmonoethanolamide are mixed with 129 parts of aniline hydrochloride Heated to 22o ° for 2 hours. The product obtained is in a molten state stirred with a solution of 82 parts of sodium acetate in zoo parts of water. Man receives a whitish-yellow, fairly firm mass, which shows a good softening effect.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB4481A DE881946C (en) | 1950-06-14 | 1950-06-14 | Process for the preparation of monoacyl derivatives of 1,2-alkylenediamines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB4481A DE881946C (en) | 1950-06-14 | 1950-06-14 | Process for the preparation of monoacyl derivatives of 1,2-alkylenediamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE881946C true DE881946C (en) | 1953-07-06 |
Family
ID=6953681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB4481A Expired DE881946C (en) | 1950-06-14 | 1950-06-14 | Process for the preparation of monoacyl derivatives of 1,2-alkylenediamines |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE881946C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1098001B (en) * | 1957-09-12 | 1961-01-26 | Knoll Ag | Process for the preparation of N- (Diaethylaminoalkyl) -salicylamiden |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE683801C (en) * | 1934-09-18 | 1939-11-16 | Chem Ind Basel | Process for the preparation of substituted amides of fatty aromatic monocarboxylic acids |
-
1950
- 1950-06-14 DE DEB4481A patent/DE881946C/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE683801C (en) * | 1934-09-18 | 1939-11-16 | Chem Ind Basel | Process for the preparation of substituted amides of fatty aromatic monocarboxylic acids |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1098001B (en) * | 1957-09-12 | 1961-01-26 | Knoll Ag | Process for the preparation of N- (Diaethylaminoalkyl) -salicylamiden |
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