PL400709A1 - Proton ionic liquids with 1-(2-chloroethyl)piperydyne cation and 1-(2-chloroethyl)morpholine and a process for their preparation - Google Patents
Proton ionic liquids with 1-(2-chloroethyl)piperydyne cation and 1-(2-chloroethyl)morpholine and a process for their preparationInfo
- Publication number
- PL400709A1 PL400709A1 PL400709A PL40070912A PL400709A1 PL 400709 A1 PL400709 A1 PL 400709A1 PL 400709 A PL400709 A PL 400709A PL 40070912 A PL40070912 A PL 40070912A PL 400709 A1 PL400709 A1 PL 400709A1
- Authority
- PL
- Poland
- Prior art keywords
- chloroethyl
- carbon atoms
- chain length
- piperidinium
- alkyl chain
- Prior art date
Links
- 239000002608 ionic liquid Substances 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 150000001768 cations Chemical class 0.000 title abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 title 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- WNRWEBKEQARBKV-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine Chemical compound ClCCN1CCCCC1 WNRWEBKEQARBKV-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 150000002823 nitrates Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- -1 tetrafluoroborates Chemical class 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 abstract 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 238000005698 Diels-Alder reaction Methods 0.000 abstract 1
- 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 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Przedmiotem wynalazku sa protonowe ciecze jonowe z kationem 1-(2-chloroetylo)piperydyniowym oraz 1-(2-chloroetylo)morfoliniowym majace zastosowanie jako medium reakcji Dielsa-Aldera oraz sposób ich otrzymywania. Protonowe ciecze jonowe z kationem 1-(2-chloroetylo)piperydyniowym oraz 1-(2-chloroetylo)morforliniowym sa to zwiazki o wzorze ogólnym 1, w którym A- oznacza anion: organiczny alkilokarboksylowy o dlugosci lancucha alkilowego od 1 do 10 atomów wegla, lub alkanosulfonianowy o dlugosci lancucha alkilowego od 1 do 10 atomów wegla, lub bis(trifluorometylosulfonylo)imidkowy, albo nieorganiczny z grupy: weglanów, lub ortofosforanów(V), lub azotanów(III), lub azotanów(V), lub siarczanów(IV), siarczanów(VI), lub tetrafluoroboranów, lub heksafluorofosforanów, lub dicyjanoimidków. W odmianie sposób ich otrzymywania polega na tym, ze chlorowodorek 1-(2-chloroetylo)piperydyniowy lub 1-(2-chloroetylo)morfoliniowy, rozpuszcza sie w alkoholu alifatycznym o dlugosci lancucha weglowego od jednego do czterech atomów wegla, lub ich mieszaninie, korzystnie w metanolu, miesza sie z alkoholanowym roztworem soli sodowej lub potasowej, lub litowej, lub amonowej kwasu alkilokarboksylowego o dlugosci lancucha alkilowego od 1 do 10 atomów wegla, lub alkanosulfonowego o dlugosci lancucha alkilowego od 1 do 10 atomów wegla, o stezeniu co najmniej 1%, w stosunku molowym chlorowodorku 1-(2-chloroetylo)piperydyniowego lub 1-(2-chloroetylo)morfoliniowego do soli kwasu organicznego od 1:1 do 1:1,05, w temperaturze od 293 do 363K, w czasie co najmniej 10 minut, nastepnie odsacza sie nieorganiczny produkt uboczny, po czym z przesaczu usuwa sie rozpuszczalnik.The present invention relates to protic ionic liquids with a 1- (2-chloroethyl) piperidinium and 1- (2-chloroethyl) morpholinium cation for use as a Diels-Alder reaction medium and the method for their preparation. Protic ionic liquids with a 1- (2-chloroethyl) piperidinium and 1- (2-chloroethyl) morforlinium cation are compounds of general formula 1, in which A- is an organic alkylcarboxylic anion with an alkyl chain length of from 1 to 10 carbon atoms, or an alkanesulfonate with an alkyl chain length of 1 to 10 carbon atoms, or bis (trifluoromethylsulfonyl) imide or inorganic from the group of: carbonates, or orthophosphates (V), or nitrates (V), or nitrates (IV) , sulfates, or tetrafluoroborates, or hexafluorophosphates, or dicyanoimides. In a variation, the method for their preparation is that 1- (2-chloroethyl) piperidinium or 1- (2-chloroethyl) morpholine hydrochloride is dissolved in an aliphatic alcohol with a carbon chain length of one to four carbon atoms, or a mixture thereof, preferably in methanol, it is mixed with an alcoholic solution of a sodium or potassium or lithium or ammonium salt of an alkylcarboxylic acid with an alkyl chain length of 1 to 10 carbon atoms, or an alkanesulfonic salt with an alkyl chain length of 1 to 10 carbon atoms with a concentration of at least 1% , in a molar ratio of 1- (2-chloroethyl) piperidinium or 1- (2-chloroethyl) morpholinium hydrochloride to the salt of an organic acid from 1: 1 to 1: 1.05 at a temperature of 293 to 363K for at least 10 minutes , the inorganic by-product is filtered off and the solvent is removed from the filtrate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL400709A PL220868B1 (en) | 2012-09-10 | 2012-09-10 | Proton ionic liquids with 1-(2-chloroethyl)piperydyne cation and 1-(2-chloroethyl)morpholine and a process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL400709A PL220868B1 (en) | 2012-09-10 | 2012-09-10 | Proton ionic liquids with 1-(2-chloroethyl)piperydyne cation and 1-(2-chloroethyl)morpholine and a process for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL400709A1 true PL400709A1 (en) | 2014-03-17 |
| PL220868B1 PL220868B1 (en) | 2016-01-29 |
Family
ID=50240924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL400709A PL220868B1 (en) | 2012-09-10 | 2012-09-10 | Proton ionic liquids with 1-(2-chloroethyl)piperydyne cation and 1-(2-chloroethyl)morpholine and a process for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL220868B1 (en) |
-
2012
- 2012-09-10 PL PL400709A patent/PL220868B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL220868B1 (en) | 2016-01-29 |
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