CH252068A - Process for the preparation of a new amide derivative. - Google Patents
Process for the preparation of a new amide derivative.Info
- Publication number
- CH252068A CH252068A CH252068DA CH252068A CH 252068 A CH252068 A CH 252068A CH 252068D A CH252068D A CH 252068DA CH 252068 A CH252068 A CH 252068A
- Authority
- CH
- Switzerland
- Prior art keywords
- amide derivative
- mol
- carried out
- preparation
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000001408 amides Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 4
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 4
- 238000005187 foaming Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 claims description 3
- 239000003599 detergent Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 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 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- SPVVMXMTSODFPU-UHFFFAOYSA-N 3-methyl-n-(3-methylbutyl)butan-1-amine Chemical compound CC(C)CCNCCC(C)C SPVVMXMTSODFPU-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Amidabkömmlings. Es wurde gefunden, dass man zu einem neuen Amidabkömmling gelangt, wenn man 1 Mol technisches Ölsäureamid mit 1 Mol Crotonaldehyd und 2 Mol Natkumbisulfit umsetzt.
Die Umsetzung kann z. B. bei 100 bis 200 , vorteilhaft in Gegenwart eines Lösungs mittels, wie Diäthylenglykol oder N-F'ormyl- morphodin, vorgenommen werden. Im allge meinen ist es zweckmässig, die verfahrens gemässe Umsetzung in Gegenwart von ge ringen Mengen eines sekundären Amins oder eines entsprechenden Salzes, z. B. unter Zu satz von Piperidin, Diisoamylamin oder Di- äthanolamin, vorzunehmen.
Auf diese Weise kann die Reaktionsgeschwindigkeit erhöht werden.
Das neue Ergebnis bildet eine gelb liche, weiche, hygroskopische Masse, die vom Wasser zu einer schäumenden Lösung auf genommen wird. Es kann als Tegtilhilfsstoff, z. B. als Waschmittel, verwendet werden. Beispiel <I>1:</I> 5,6 Teile Ölsäureamid werden. in 15 Tei len Diäthylenglykol bei 110 bis 120 gelöst.
Nach dem Abkühlen auf 80 bis 90 werden zuerst unter Rühren 1,8 Teile Crotonaldehyd und hierauf 5 Teile pulverisiertes, gut ge trocknetes Natriumbisulfät eingetragen. Die Temperatur wird auf 130 bis 140 gesteigert und während 2 Stunden auf dieser Höhe ge halten. Durch Zusatz von 0,1 Teil Piperidin kann die Reaktion etwas beschleunigt wer den.
Durch Erwärmen mit Aceton, Kühlen und Filtrieren, kann das Produkte vom Di- äthylenglykol befreit werden. Es werden 8,5 Teile einer gelblichen, weichen, hygroskopi schen Masse erhalten. Eine Probe ist in Wasser leicht löslich. Die Lösung ist klar, schäumt kräftig und zeigt sehr gute Was6h- eigenschaften, auch in hartem Wasser.
Beispiel <I>2:</I> 2,8 Teile Ödsäureamid, 0,9 Teile Croton- aldehyd und 2,5 Teile fein pulverisiertes, gut getrocknetes Natriumbisulfit werden im Öl bad von 150 biss 160 unter langsamem Rüh ren erhitzt. Wenn die Masse zu schmelzen beginnt, wird 0,1 Teil Piperidin zugegeben.
Es tritt ziemlich starkes Schäumen auf und die zuerst gelbliche, dünnflüssige Masse versteift sich nach und nach. Nach ca. 30 Mi nuten hört das Schäumen ganz auf und das Produkt ist so fest geworden, dass nicht mehr gerührt werden kann. Eine Probe ist in Was ser unter geringer Trübung löslich.
Nachdem noch 30 Minuten ohne Rühren weiter erhitzt worden ist, werden 50 Teile absoluter Alko hol zugegeben, worauf man unter Rückfluss so lange kocht, bis alles gut verteilt ist. Nach dem Abkühlen wird das Reaktionsprodukt abfältriert. Es besitzt die gleichen Eigen schaften wie das Erzeugnis nach Beispiel 1.
Process for the preparation of a new amide derivative. It has been found that a new amide derivative is obtained if 1 mole of technical oleic acid amide is reacted with 1 mole of crotonaldehyde and 2 moles of sodium bisulfite.
The implementation can e.g. B. at 100 to 200, advantageously in the presence of a solvent means such as diethylene glycol or N-F'ormyl- morphodin are made. In general, it is expedient to carry out the implementation according to the process in the presence of small amounts of a secondary amine or a corresponding salt, eg. B. with the addition of piperidine, diisoamylamine or diethanolamine.
In this way, the reaction speed can be increased.
The new result is a yellowish, soft, hygroscopic mass that is absorbed by the water into a foaming solution. It can be used as a Tegtilhilfsstoff, z. B. can be used as a detergent. Example <I> 1: </I> 5.6 parts of oleic acid amide. dissolved in 15 parts diethylene glycol at 110 to 120.
After cooling to 80 to 90, 1.8 parts of crotonaldehyde and then 5 parts of powdered, well-dried sodium bisulfate are first introduced with stirring. The temperature is increased to 130 to 140 and held at this level for 2 hours. The reaction can be accelerated somewhat by adding 0.1 part of piperidine.
The product can be freed from diethylene glycol by heating with acetone, cooling and filtering. 8.5 parts of a yellowish, soft, hygroscopic mass are obtained. A sample is easily soluble in water. The solution is clear, foams vigorously and shows very good washing properties, even in hard water.
Example <I> 2: </I> 2.8 parts of edic acid amide, 0.9 parts of crotonic aldehyde and 2.5 parts of finely powdered, well-dried sodium bisulfite are heated in an oil bath from 150 to 160 with slow stirring. When the mass begins to melt, 0.1 part piperidine is added.
There is quite a strong foaming and the initially yellowish, thin-bodied mass gradually stiffens. After about 30 minutes, the foaming stops completely and the product has become so firm that it can no longer be stirred. A sample is soluble in water with little turbidity.
After heating has continued for 30 minutes without stirring, 50 parts of absolute alcohol are added, whereupon the mixture is refluxed until everything is well distributed. After cooling, the reaction product is filtered off. It has the same properties as the product according to Example 1.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH252068T | 1945-07-16 | ||
| CH246668T | 1945-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH252068A true CH252068A (en) | 1947-11-30 |
Family
ID=25729122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH252068D CH252068A (en) | 1945-07-16 | 1945-07-16 | Process for the preparation of a new amide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH252068A (en) |
-
1945
- 1945-07-16 CH CH252068D patent/CH252068A/en unknown
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