DE710480C - Process for the preparation of derivatives of higher amides - Google Patents
Process for the preparation of derivatives of higher amidesInfo
- Publication number
- DE710480C DE710480C DEH136071D DEH0136071D DE710480C DE 710480 C DE710480 C DE 710480C DE H136071 D DEH136071 D DE H136071D DE H0136071 D DEH0136071 D DE H0136071D DE 710480 C DE710480 C DE 710480C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- amides
- weight
- parts
- derivatives
- 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
- 150000001408 amides Chemical class 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- -1 aliphatic amines Chemical class 0.000 description 7
- IQNKUQDXFKGYSX-UHFFFAOYSA-N 2-chloro-n-dodecylacetamide Chemical compound CCCCCCCCCCCCNC(=O)CCl IQNKUQDXFKGYSX-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 235000011941 Tilia x europaea Nutrition 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000004571 lime Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229940106681 chloroacetic acid Drugs 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 229940043237 diethanolamine Drugs 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- HXKXBCBZXXQPPD-UHFFFAOYSA-N 2-bromododecanoic acid Chemical compound CCCCCCCCCCC(Br)C(O)=O HXKXBCBZXXQPPD-UHFFFAOYSA-N 0.000 description 1
- LSLIPOCUJFXUNM-UHFFFAOYSA-N 2-chloro-5-sulfobenzoic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1Cl LSLIPOCUJFXUNM-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- DKEXFJVMVGETOO-LURJTMIESA-N Gly-Leu Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)CN DKEXFJVMVGETOO-LURJTMIESA-N 0.000 description 1
- 235000001008 Leptadenia hastata Nutrition 0.000 description 1
- 244000074209 Leptadenia hastata Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QQWGVQWAEANRTK-UHFFFAOYSA-N bromosuccinic acid Chemical compound OC(=O)CC(Br)C(O)=O QQWGVQWAEANRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- WOAZEKPXTXCPFZ-UHFFFAOYSA-N dimethyl(phenyl)azanium;chloride Chemical compound Cl.CN(C)C1=CC=CC=C1 WOAZEKPXTXCPFZ-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 108010050848 glycylleucine Proteins 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 0.000 description 1
- 108010084652 homeobox protein PITX1 Proteins 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OMEMQVZNTDHENJ-UHFFFAOYSA-N n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCNC OMEMQVZNTDHENJ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical class CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- NSFYPZRDTCJZAS-UHFFFAOYSA-M sodium;1-aminoethanesulfonate Chemical compound [Na+].CC(N)S([O-])(=O)=O NSFYPZRDTCJZAS-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/22—Amides or hydrazides
- C09K23/24—Amides of higher fatty acids with aminoalkylated sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/521—Carboxylic amides (R1-CO-NR2R3), where R1, R2 and R3 are alkyl or alkenyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Derivaten höherer Amide Es wurde gefunden, daß sich technisch wertvolle Derivate höherer Amide dadurch gewinnen lassen, daß man freie Carboxylgruppen und Hyäroxylgruppen nicht enthaltenden, aus mindestens einen höheren aliphatischen bzw. hydroaromatischen Rest im Molekül enthaltenden Aminen einerseits und austauschfähiges Halogen enthaltenden organischen Säuren andererseits hergestellte Amide mit Ammoniak bzw. organischen Substitutionsprodukten des Ammoniaks umsetzt.Process for the preparation of derivatives of higher amides It has been found that technically valuable derivatives of higher amides can be obtained in that one free carboxyl groups and not containing hydroxyl groups, from at least containing a higher aliphatic or hydroaromatic radical in the molecule Amines on the one hand and exchangeable halogen-containing organic acids on the other hand manufactured amides with ammonia or organic substitution products of ammonia implements.
Solche Substitutionsprodukte sind primäre, sekundäre oder tertiäre Amine. Zu der Umsetzung können beispielsweise aliphatische Amine, wie Äthylamin, Diäthylamin, Triäthylamin, Aminoessigsäure, Aminoäthansulfonsäure, Äthanolamin, Diäthanolamin, Triäthanoiamin u. dgl., ferner aromatische Amine, wie Anilin, sowie dessen Homologe und Substitutionsprodukte verwendet werden. Auch solche Verbindungen, die den Stickstoff ringförmig gebunden enthalten, wie Pyridin, Piperidin, können umgesetzt werden. Die Reaktion kann in Gegenwart oder Abwesenheit von Usungs- und Verdünnungsmitteln vorgenommen werden.Such substitution products are primary, secondary or tertiary Amines. For example, aliphatic amines such as ethylamine, Diethylamine, triethylamine, aminoacetic acid, aminoethanesulfonic acid, ethanolamine, Diethanolamine, triethanoiamine and the like, and also aromatic amines such as aniline, as well as whose homologues and substitution products are used. Also such connections which contain the nitrogen bonded in a ring, such as pyridine, piperidine, can implemented. The reaction can be in the presence or absence of use and Diluents can be made.
Unter den zum Aufbau der zu der Umsetzung verwendeten Amide nötigen höheren Aminen haben sich als besonders geeignet erwiesen: die 6 oder mehr C-Atome enthaltenden aliphatischen Amine gesättigter oder ungesättigter Natur, wie beispielsweise das Undecylamin, das Dadecylamin, das Methyldodecylamin, ferner Homologe der genannten Amine, wie das Decyl- und Tetradecylamin, das Octodeoenylamin, das -Cyclohexylamin u. dgl. mehr.Among the amides required to build up the amides used for the reaction higher amines have proven to be particularly suitable: the 6 or more carbon atoms containing aliphatic amines of saturated or unsaturated nature, such as the undecylamine, the dadecylamine, the methyldodecylamine, further homologues of the named Amines such as decyl and tetradecyl amine, octodeoenyl amine, cyclohexyl amine and the like more.
Unter den zum Aufbau der zu der Umsetzung verwendeten Amide nötigen, reaktionsfähige Halogenatome enthaltenden Säuren haben sich als besonders geeignet erwiesen die a-Halogenfettsäuren, wie Monochloressigsäure, Monobrombernsteinsäure, Dichloressigsäure, a-Bromlaurinsäure; an Stelle derartiger a-Halogensäuren kann man aber auch aliphatische Carbonsäuren, die in anderen Stellungen durch Halogena.tame substituiert sind, benutzen; ferner auch bewegliche Halogenatome enthaltende Carbonsäuren anderer organischer Reihen, wie z. B.:. die Benzylchlorid-.l-carbonsäure, die 2-Chlör:: benzoesäure bzw. deren Substitutionsprodukte;, wie z. B. die 5-Sulfo-2-chlorbenzoesäure. Auch Sulfonamide, die ein reaktionsfähiges Halogenatom in dem Säurerest enthalten, können zu der Umsetzung benutzt werden.Among the amides required to build up the amides used for the reaction, Acids containing reactive halogen atoms have proven to be particularly suitable proved the a-halogen fatty acids, such as monochloroacetic acid, monobromosuccinic acid, Dichloroacetic acid, α-bromo lauric acid; in place of such α-halogen acids but you also have aliphatic carboxylic acids in others Positions are substituted by Halogena.tame, use; also mobile halogen atoms containing carboxylic acids of other organic series, such as. B.:. the benzyl chloride-.l-carboxylic acid, the 2-chloro :: benzoic acid or its substitution products; such. B. 5-sulfo-2-chlorobenzoic acid. Also sulfonamides, which contain a reactive halogen atom in the acid residue, can be used for the implementation.
So gelangt man beispielsweise zu wertvollen Verbindungen, wenn man das Chloressigsäure-N-dodecylamid mit Anilin, Piperidin, Pyridin, Triäthylamin und ähnlichen Aminen umsetzt. An Stelle des genannten Amids können auch seine 'Homologen, wie .das Chloressigsäure-N-undecylamid, sowie ;=d'eren Gemische verwendet werden.For example, you can make valuable connections if you the chloroacetic acid-N-dodecylamide with aniline, piperidine, pyridine, triethylamine and converts similar amines. Instead of the amide mentioned, its' homologues, like .the chloroacetic acid-N-undecylamide, as well as; = d'eren mixtures are used.
@#@T3ei der Umsetzung von beispielsweise _C-'.#loressigsäure-N-undecylamid#.@loressigsäure-N-undecylamid mit Moromethylamin wird das Methylamino2ssigsäure-N-undecylamid erhalten. Bei der Umsetzung mit Ammoniak oder anderen organischen Substitutionsprodukten des Ammoniaks gelangt man zu ähnlich konstituierten Verbindungen. Bei der Umsetzung mit tertiären Aminen erhält man Ammoniumderivate gemäß folgendem Reaktionsschema: Die neuen höhermolekularen Verbindungen sollen, soweit sie wasserunlöslich sind, als Weichmachungsmittel sowie in der Industrie des Kautschuks, z. B. als Alterungsschutzmittel, Anwendung finden.When reacting, for example, _C- '. # Loroacetic acid-N-undecylamide #. @ Loroacetic acid-N-undecylamide with moromethylamine, methylamino-acetic acid-N-undecylamide is obtained. The reaction with ammonia or other organic substitution products of ammonia leads to compounds with a similar structure. When reacting with tertiary amines, ammonium derivatives are obtained according to the following reaction scheme: The new higher molecular weight compounds should, insofar as they are water-insoluble, as plasticizers and in the rubber industry, e.g. B. as an anti-aging agent, use.
Die wasserlöslichen, gemäß der vorliegenden Erfindung hergestellten Produkte besitzen seifenartige Eigenschaften, z. B. gutes Netz-und Schaumvermögen. Sie zeichnen sich durch hervorragende Kalle- und Säurebeständigkeit aus. Die Produkte können als solche oder zusammen mit anderen Seifen, seifenartigen Stoffen, Füllstoffen, aktiven Sauerstoff abgebenden Verbindungen u. dgl. verwendet werden.The water soluble ones made according to the present invention Products have soap-like properties, e.g. B. good wetting and foaming properties. They are characterized by their excellent resistance to alkalis and acids. The products can be used as such or together with other soaps, soap-like substances, fillers, active oxygen releasing compounds and the like can be used.
Bei wissenschaftlichen Arbeiten über die Synthese von Polypeptiden ist bereits Chloracetylleucin mit Ammoniak zur Gewinnung des Glycylleucins umgesetzt worden. Demgegenüber unterscheidet sich das Verfahren der vorliegenden Erfindung dadurch, daß unter Verwendung von höhermolekularen carboxyl- und hydroxylgruppenfreien Aminen hergestellte S,äureamide zur Anwendung kommen. Auf diese Weise werden wertvolle kalkbeständige kapillaraktive Stoffe gewonnen. Auch ist bereits bekanntgeworden, organische Substitutionsprodukte des Ammoniaks mit Amiden aus Säuren mit austauschfähigem Halogen und Aminen mit 5 und weniger Kohlenstoffatomen im Molekül umzusetzen. Dabei wurden aber keine Produkte gewonnen, die technische Verwertung gefunden haben. Schließlich hat man auch schon vorgeschlagen; Amide aus höheren Aminen und Halogencarbonsäuren mit Sufiten umzusetzen. Diese Sulfoverbin.dungen sind schwer in kaltem Wasser löslich und wenig kalkbeständig, während nach der vorliegenden Erfindung Verbindungen gewonnen werden können, die leicht in Wasser löslich und gut kalkbeständig sind. Beispiele t. 82 Gewichtsteile Chloressigsäureundecylamid «-erden mit 27 Gewichtsteilen Pyridin etwa 2 Stunden auf dem Wasserbad erhitzt. Das Additionsprodukt, das aus Aceton umkristallisiert werden kann, fällt in Form von fast farblosen Kristallen an, die sich in kaltem Wasser Idar auflösen.For scientific work on the synthesis of polypeptides chloroacetylleucine has already been reacted with ammonia to obtain glycylleucine been. In contrast, the method of the present invention differs in that using higher molecular weight carboxyl and hydroxyl groups-free S, acid amides made from amines are used. That way it will be valuable lime-resistant capillary-active substances obtained. It has also already become known organic substitution products of ammonia with amides from acids with exchangeable To implement halogen and amines with 5 or fewer carbon atoms in the molecule. Included but no products were obtained that could be used for technical purposes. In the end one has already suggested; Amides from higher amines and halocarboxylic acids to implement with Sufites. These sulfo compounds are difficult to dissolve in cold water and little lime-resistant, while compounds obtained according to the present invention that are easily soluble in water and have good lime-resistance. Examples t. 82 parts by weight of chloroacetic acid undecylamide earths with 27 parts by weight of pyridine heated on the water bath for about 2 hours. The addition product which recrystallizes from acetone can be, falls in the form of almost colorless crystals, which are in cold Dissolve water Idar.
2. 1235 Gewichtsteile Chloressigs.äureundecylamid werden mit 56o Gewichtsteilen Triäthylamin etwa 6 bis 8 Stunden auf dem Wasserbad erhitzt. Man erhält das Additionsprodukt in Form einer weißen Kristallmasse, die sich in kaltem Wasser klar auflöst.2. 1235 parts by weight of chloroacetic acid undecylamide are heated with 56o parts by weight of triethylamine for about 6 to 8 hours on a water bath. The addition product is obtained in the form of a white crystal mass which dissolves clearly in cold water.
Zu .ähnlich konstituierten Verbindungen glangt man auch, wenn man die entsprechenden Halogenpropionsäureamide sowie Halogenäthan- oder -propansulfonamide verwendet.One can also achieve similarly constituted connections if one the corresponding halopropionic acid amides and haloethane or propane sulfonamides used.
3. 8o Gewichtsteile Chloressigsäureundecylamid werden mit 75 Gewichtsteilen Anilin etwa 3 bis q. Stunden auf dem Wasserbad erhitzt. Das Reaktionsprodukt wird durch mehrmaliges Waschen mit verdünnter Salzsäure vom überschüssigen Anilin befreit und aus Petroläther umkristallisiert. Das Anilinoessigsäureundecylamid stellt ein schwach gefärbtes weißes Pulver vom Fp. 4.9 bis 5o° dar.3. 80 parts by weight of chloroacetic acid undecylamide are combined with 75 parts by weight Aniline about 3 to q. Heated for hours on the water bath. The reaction product will freed from excess aniline by washing several times with dilute hydrochloric acid and recrystallized from petroleum ether. The anilinoacetic acid undecylamide ceases slightly colored white powder with a melting point of 4.9 to 50 °.
4. 8,9 Gewichtsteile aminoäthansulfonsaures Natrium, Zoo Gewichtsteile Alkohol (y5o;oig), 13 Gewichtsteile Chloressigsäuredodecylamid und 6,6 Gewichtsteile Dimethylanilin werden längere Zeit unter Rückfluß zum Sieden erhitzt. Das Reaktionsprodukt wird nach dem Verdampfen des Lösungsmittels von Dimethylanilinhydrochlorid befreit und gegebenenfalls neutralisiert. Es läßt sieh durch Umlösen und Aussalzen aus Wasser als gelbbraune klar wasserlösliche Paste gewinnen, deren wäßrige Lösungen gutes Netz-und Schaumvermögen sowie gute Kalk- und Säurebeständigkeit aufweisen. An Stelle des Chloressigsäure-N-dodecylamids kann die Umsetzung auch mit dessen Homologen oder Homologengemischen durchgeführt werden.4. 8.9 parts by weight of sodium aminoethanesulfonate, zoo parts by weight Alcohol (y5o; oig), 13 parts by weight of chloroacetic acid dodecylamide and 6.6 parts by weight Dimethylaniline are refluxed for a long time. The reaction product is freed from dimethylaniline hydrochloride after evaporation of the solvent and neutralized if necessary. It can be seen by dissolving and salting out of water win as a yellow-brown, clear water-soluble paste, the aqueous solutions of which are good Wetting and foaming power as well as good lime and Acid resistance exhibit. Instead of the chloroacetic acid-N-dodecylamide, the reaction can also be carried out with its homologues or homolog mixtures.
5. 4o Gewichtsteile Chloressigsäuredodecylamid, 33 Gewichtsteile Methyltaurin (Na-Salz), 13,3 Gewichtsteile Pyridin und 5oo Gewi:chtsteüe eines alkoholischen Wassergemisches (I : I) «erden längere Zeit unter Rückfuß zum Sieden erhitzt. Das Gemisch wird eingedampft, vom salzsauren Pyridin befreit und durch Umlösen aus Wasser oder Alkohol als reinweiße Substanz erhalten. Das Produkt von der Formel C],HZ5.NH#CO.CHz#N(CH3)#CHz#CHz.S03Na besitzt ausgezeichnetes Netz- und Schaum vermögen, löst sich klar in Wasser und ist völlig kalk- und säurebeständig.5. 40 parts by weight of chloroacetic acid dodecylamide, 33 parts by weight of methyl taurine (Na salt), 13.3 parts by weight of pyridine and 500 parts by weight of an alcoholic Mixtures of water (I: I) «are heated to boiling under the backfoot for a long time. That The mixture is evaporated, freed from the hydrochloric acid pyridine and redissolved from water or alcohol received as a pure white substance. The product of the formula C], HZ5.NH # CO.CHz # N (CH3) # CHz # CHz.S03Na has excellent wetting and foam properties, dissolves clearly in water and is completely resistant to lime and acids.
Die Umsetzung kann in derselben Weise mit Homologen des Chloressigsäuredodecylamids, wie Octyl-, Decyl , Tetradecyl-, Hexadecyl- oder Octodecylamiden der Chloressigsäure .sowie deren Gemischen erfolgen.The reaction can be carried out in the same way with homologues of chloroacetic acid dodecylamide, such as octyl, decyl, tetradecyl, hexadecyl or octodecyl amides of chloroacetic acid as well as their mixtures.
6. 5o Gewichtsteile Chloressigs,äuredod@ecylamid werden mit 45 Gewichtsteilen Diäthanolamin 3 Stunden auf 18o bis 19o° erhitzt. Das Reaktionsprodukt wird in Äther gelöst und mit verdüamter Salzsäure von nicht umgesetztem Diäthanol.amin befreit. Man erhält das Umsetzungsprodukt als weiße pulvrige Masse.6. 50 parts by weight of chloroacetic acid, äuredod @ ecylamid are mixed with 45 parts by weight Diethanolamine heated to 18o to 19o ° for 3 hours. The reaction product is in ether dissolved and freed from unreacted diethanol amine with diluted hydrochloric acid. The reaction product is obtained as a white powdery mass.
7. 5o Gewichtsteüe Chloressigs,äuredodecylamid werden mit 4o Gewichtsteilen (ß, y)-Dioxyp.ropylamin etwa 3 Stunden auf 185 bis 195' erhitzt. Nach dem Erkalten wird das Reaktionsprodukt in Äther gelöst, das unveränderte Amin entfernt, die ätherische Lösung mit Sodalösung neutral gewaschen und der Äther abgedampft. Das Produkt, das man gegebenenfalls aus Alkohol umkristallisieren kann, fällt als weiße Kristallmasse an. In gleicher Weise läßt sich die Umsetzung auch mit dem Di-(ß,y)-dioxypropylamin ausführen;.7. 50 parts by weight of chloroacetic acid and acid dodecylamide are added with 40 parts by weight (ß, y) -Dioxyp.ropylamine heated to 185 to 195 'for about 3 hours. After cooling down if the reaction product is dissolved in ether, the unchanged amine is removed, the ethereal one Solution washed neutral with soda solution and the ether evaporated. The product that you can optionally recrystallize from alcohol, precipitates as a white crystal mass at. The reaction can also be carried out in the same way with di- (β, γ) -dioxypropylamine carry out;.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH136071D DE710480C (en) | 1933-04-28 | 1933-04-28 | Process for the preparation of derivatives of higher amides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH136071D DE710480C (en) | 1933-04-28 | 1933-04-28 | Process for the preparation of derivatives of higher amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE710480C true DE710480C (en) | 1941-09-15 |
Family
ID=7177429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH136071D Expired DE710480C (en) | 1933-04-28 | 1933-04-28 | Process for the preparation of derivatives of higher amides |
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| Country | Link |
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| DE (1) | DE710480C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1103321B (en) * | 1954-04-27 | 1961-03-30 | Henkel & Cie Gmbh | Process for the preparation of amides ª ‡ -halogenated, aliphatic carboxylic acids |
-
1933
- 1933-04-28 DE DEH136071D patent/DE710480C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1103321B (en) * | 1954-04-27 | 1961-03-30 | Henkel & Cie Gmbh | Process for the preparation of amides ª ‡ -halogenated, aliphatic carboxylic acids |
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