PL434306A1 - Bis-ammonium ionic liquids with L-tryptophanate anion, method of their preparation and use as cleaning agents - Google Patents
Bis-ammonium ionic liquids with L-tryptophanate anion, method of their preparation and use as cleaning agentsInfo
- Publication number
- PL434306A1 PL434306A1 PL434306A PL43430620A PL434306A1 PL 434306 A1 PL434306 A1 PL 434306A1 PL 434306 A PL434306 A PL 434306A PL 43430620 A PL43430620 A PL 43430620A PL 434306 A1 PL434306 A1 PL 434306A1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- bis
- solvent
- anion
- ionic liquids
- Prior art date
Links
- 239000002608 ionic liquid Substances 0.000 title abstract 4
- -1 L-tryptophanate anion Chemical class 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 239000012459 cleaning agent Substances 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 6
- 239000002904 solvent Substances 0.000 abstract 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 abstract 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 2
- 239000003456 ion exchange resin Substances 0.000 abstract 2
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 2
- 229960002510 mandelic acid Drugs 0.000 abstract 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 abstract 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 abstract 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 229910017053 inorganic salt Inorganic materials 0.000 abstract 1
- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
Landscapes
- Indole Compounds (AREA)
Abstract
Bis-amoniowe ciecze jonowe z anionem ʟ-tryptofanianowym o wzorze ogólnym 1, w którym A oznacza anion kwasu trans-cynamonowego o wzorze 4, albo kwasu migdałowego o wzorze 5, albo kwasu octowego o wzorze 6. Zgłoszenie obejmuje też sposób otrzymywania bis-amoniowych cieczy jonowych z anionem ʟ-tryptofanianowym, który charakteryzuje się tym, że dibromek alkilo-1,X-bis-(decylodimetyloamoniowy) o wzorze 2, poddaje się reakcji alkalizacji za pomocą żywicy jonowymiennej, albo wodorotlenku potasu, albo wodorotlenku sodu w stosunku molowym dibromku alkilo-1,X-bis-(decylodimetyloamoniowego) do donoru jonów hydroksylowych 1:2, w rozpuszczalniku z grupy alkoholi krótkołańcuchowych: metanol albo etanol, w temperaturze od 20 do 50°C, korzystnie 25°C, w czasie od 15 minut do 10 godzin, po czym z rozpuszczalnika odsącza się żywicę jonowymienną z zaadsorbowanymi jonami bromkowymi albo powstałą sól nieorganiczną, po czym układ reagentów, po reakcji alkalizacji za pomocą wodorotlenku potasu albo wodorotlenku sodu schładza się do temperatury od 2 do 10°C, korzystnie 2°C, następnie do otrzymanego wodorotlenku przy ciągłym mieszaniu dodaje się stechiometryczną ilość ʟ-tryptofanu o wzorze 3 oraz wybranego kwasu pochodzenia naturalnego, którym jest kwas trans-cynamonowy o wzorze 4, albo kwas migdałowy o wzorze 5, albo kwas octowy o wzorze 6 w temperaturze od 20 do 50°C, korzystnie 25°C, w czasie od 15 do 40 minut, korzystnie 40 minut, po czym odparowuje się rozpuszczalnik, a do otrzymanego produktu dodaje się bezwodnego acetonu albo 2-propanolu, dalej całość ochładza się do temperatury od 2 do 10°C, korzystnie 2°C, po czym z rozpuszczalnika odsącza się bromek potasu albo bromek sodu, a po odpędzeniu rozpuszczalnika produkt suszy się pod obniżonym ciśnieniem w temperaturze od 40 do 80°C, korzystnie 60°C. Przedmiotem zgłoszenia jest także zastosowanie ww. bis-amoniowych cieczy jonowych.Bis-ammonium ionic liquids with a ʟ-tryptophanate anion of the general formula I, in which A is the anion of trans-cinnamic acid of the formula 4, or mandelic acid of the formula 5, or acetic acid of the formula 6. The application also covers the preparation of bis-ammonium ionic liquids with an ʟ-tryptophanate anion, characterized in that the alkyl-1, X-bis- (decyldimethylammonium) dibromide of formula 2 is alkalized with an ion exchange resin, either potassium hydroxide or sodium hydroxide in the molar ratio of dibromide alkyl-1, X-bis (decyldimethylammonium) to the hydroxyl ion donor 1: 2, in a solvent from the group of short-chain alcohols: methanol or ethanol, at a temperature of 20 to 50 ° C, preferably 25 ° C, for 15 minutes to 10 hours, then the ion-exchange resin with adsorbed bromide ions or the formed inorganic salt is filtered off from the solvent, and then the reagent system, after the alkalization reaction with potassium hydroxide or with hydroxides sodium chloride is cooled to a temperature of 2 to 10 ° C, preferably 2 ° C, then a stoichiometric amount of ʟ-tryptophan of the formula 3 and the selected acid of natural origin, which is trans-cinnamic acid of the formula 4, are added to the obtained hydroxide with constant stirring , or mandelic acid of the formula 5 or acetic acid of the formula 6 at a temperature of 20 to 50 ° C, preferably 25 ° C, for 15 to 40 minutes, preferably 40 minutes, after which the solvent is evaporated off to the obtained product Anhydrous acetone or 2-propanol is added, the whole is then cooled to a temperature of 2 to 10 ° C, preferably 2 ° C, then the potassium bromide or sodium bromide is filtered off from the solvent, and after stripping the solvent, the product is dried under reduced pressure in from 40 to 80 ° C, preferably 60 ° C. The subject of the application is also the application of the above-mentioned bis-ammonium ionic liquids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL434306A PL242896B1 (en) | 2020-06-15 | 2020-06-15 | Bis-ammonium ionic liquids with L-tryptophanate anion, method of their preparation and use as cleaning agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL434306A PL242896B1 (en) | 2020-06-15 | 2020-06-15 | Bis-ammonium ionic liquids with L-tryptophanate anion, method of their preparation and use as cleaning agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL434306A1 true PL434306A1 (en) | 2021-12-20 |
| PL242896B1 PL242896B1 (en) | 2023-05-15 |
Family
ID=80001796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL434306A PL242896B1 (en) | 2020-06-15 | 2020-06-15 | Bis-ammonium ionic liquids with L-tryptophanate anion, method of their preparation and use as cleaning agents |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL242896B1 (en) |
-
2020
- 2020-06-15 PL PL434306A patent/PL242896B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL242896B1 (en) | 2023-05-15 |
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