Extraction of noble metal (ions) by means of ionic liquids

Abstract

The present invention relates to a process for the extraction of metals from an aqueous phase by means of specific ionic liquids.

Claims

1. A process for extraction of at least one metal from an aqueous phase, the process comprising extracting the at least one metal with an ionic liquid of general formula (I) ##STR00046## wherein i) X.sup.is an anion, ii) n is a number from 0 to 14, iii) R.sup.1 and R.sup.2 independently from each other are H, -halogen, NO.sub.2, NH.sub.2, NHR.sub.x, N(R.sub.x).sub.2, R.sub.x, C(O)OH, C(O)OR.sub.x, C(O)R.sub.x or OR.sub.x, wherein R.sub.x is a straight-chained or branched, substituted or unsubstituted C1 to C18 alkyl group; wherein no additional extracting agent is used; wherein the pH value of the aqueous phase is between 8 and 0; and wherein the at least one metal to be extracted is selected from the group consisting of heavy metals, the group of rare earths and the group of actinides.

2. The process according to claim 1, wherein X.sup.is bis(trifluoromethylsulfonyl)imide or dicyanamide.

3. The process according to claim 1, wherein n=5 to 13.

4. The process according to claim 1, wherein R.sup.1 is H and R.sup.2 is selected from the group consisting of H, -halogen, NO.sub.2, NH.sub.2, NHR.sub.x, N(R.sub.x).sub.2, R.sub.x, C(O)OH, C(O)OR.sub.x, C(O)R.sub.x and OR.sub.x, wherein R.sub.x is a straight-chained or branched, substituted or unsubstituted C1 to C18 alkyl group.

5. The process according to claim 1, wherein R.sup.1 and/or R.sup.2 are groups with a +M-effect.

6. The process according to claim 5, wherein R.sup.2 is -halogen or OR.sub.x, wherein R.sub.x is a straight-chained or branched, substituted or unsubstituted C1 to C18 alkyl group.

7. The process according to claim 1, wherein the metal to be extracted is platinum and/or europium.

8. The process according to claim 1, wherein the process is carried out in a pH range between 5 and 0.

9. The process according to claim 1, wherein the extraction ratio does not decrease by more than 60% over the whole pH range.

10. The process according to claim 1, wherein the extraction is a selective extraction of at least one metal from a mixture of at least two metals in an aqueous phase.

Description

EXAMPLES

(1) Measuring Methods

(2) .sup.1H and .sup.13C NMR spectra are recorded with Bruker DRX-300 at 300.13 and 75.453 MHz. The deuterated solvent serves as an internal reference. Elementary analyses are determined by the micro-analytical laboratory of the institute with a Euro Vektor Euro EA-3000 device. Melting points of compounds are determined either by a PolyTherm A melting point device from Wagner and Mulz or, in case of liquid samples, with a Mettler-Toledo DSC device. A Netzsch STA 409 device serves to measure the thermic stability (TGA). The measurements are performed under open-air conditions with a scan rate of 10 K/min in a temperature range from 30 to 500 C.

(3) The concentration of cations was determined by ICP-MS with a ELAN 9000 from Perkin Elmer SCIEX company. For this purpose, the samples are diluted by 1:1000 in 1% HNO.sub.3 and the metal content was determined in a triple determination using a calibration curve (5, 10, 20 and 50 g/L metal in 1% HNO.sub.3). CertPrep standards (1 g/L), a SPS-SW2 standard and Rh as internal standard with 5 g/L are used as the standards. The concentration is determined at 2 hours after each addition of the ionic liquid to the solution.

(4) The pH values of the aqueous solutions are measured by a HACH sension2 gel-filled electrode.

Example 1

Extraction Ratios of Some Ionic Liquids

(5) For measuring the partition of metal ions between the aqueous phase and the ionic liquid, 30 mL of an aqueous potassium tetrachloroplatinate solution (0.1 mmol/L) are contacted with 100 L of ionic liquid. The mixture is kept in agitation for 2 hours by use of a Vibramax 100 from Heidolph at 1200 rpm. After a certain time interval, samples are taken from the aqueous phase and contacted with each 10 L of concentrated HNO.sub.3 (this serves to stabilize Pt in the solution). The concentration of cations is determined by ICP-MS.

(6) TABLE-US-00001 TABLE 1 Platinum extraction ratios E in % of different ionic liquids; R.sup.1 is in the ortho position and R.sup.2 is in the para position, the anion is bis(trifluoromethylsulfonyl)imide R.sup.1 R.sup.2 n = 0 n = 2 n = 3 n = 4 n = 5 n = 10 n = 13 H H 52.3 27.6 >96.1 29 H OMe 26.6 26.4 12.3 95.5 54.0 OMe H 12.0 35.4 14.5 H OEt 12.7 15.5 3.8 27.9 75.0 19.5 OEt H 31.9 22.9 93.5 18.2 H Cl 27.0 40.0 50.0 H Br 34.2 62.1 96.5 Br H 27.5 29.0 12.0 H Et 45.0 21.3 24.1 74.7 30 Et H 44.0 42.9 23.8 61.9 33 OMe NO.sub.2 66.6

(7) TABLE-US-00002 TABLE 2 Platinum extraction ratios E in % of an ionic liquid; R.sup.1 is in the ortho position and R.sup.2 is in the para position, the anion is dicyanamide R.sup.1 R.sup.2 n = 0 n = 2 n = 3 n = 4 n = 5 n = 10 n = 13 H OMe 91.1

(8) The examined ionic liquids show very good extraction ratios. In particular, ionic liquids are particularly suitable for the platinum extraction where n=10 as they can extract more than 90% of Pt from the aqueous phase. If one compares the ionic liquid having dicyanamide as an ion with the corresponding ionic liquid having bis(trifluoromethylsulfonyl)imide as the ion, one recognizes that both ionic liquids show similarly good extraction ratios which suggests that both anions are well suitable for the intended process.

Example 2

Partition Ratio D of Some Ionic Liquids

(9) For measuring the partition of metal ions between the aqueous phase and the ionic liquid, 30 mL of an aqueous potassium tetrachloroplatinate solution (0.1 mmol/L) are contacted with 100 L of ionic liquid. The mixture is kept in agitation for 2 hours by use of a Vibramax 100 from Heidolph at 1200 rpm. After a certain time interval, samples are taken from the aqueous phase and contacted with each 10 L of concentrated HNO.sub.3 (this serves to stabilize Pt in the solution). The concentration of cations is determined by ICP-MS.

(10) TABLE-US-00003 TABLE 3 Platinum partition ratios D of different ionic liquids; R.sup.1 is in the ortho position and R.sup.2 is in the para position, the anion is bis(trifluoromethylsulfonyl)imide R.sup.1 R.sup.2 n = 0 n = 2 n = 3 n = 4 n = 5 n = 10 n = 13 H H 1.232 0.414 184.357 0.454 H OMe 0.399 0.389 0.151 109.7 1.345 OMe H 0.148 0.598 0.183 H OEt 0.157 0.198 0.043 0.420 3.614 0.257 H Cl 0.396 0.723 1.116 H Br 0.568 1.877 1570.3 Br H 0.413 0.442 0.148 H Et 0.916 0.294 0.344 3.548 0.458 Et Ht 0.864 0.828 0.338 1.851 0.525

(11) Many of the examined the ionic liquids show very good partition ratios. In particular, ionic liquids are particularly suitable for the platinum extraction where n=10 and, hence, carrying an undecyl chain.

Example 3

Extraction Ratios at Different pH Values

(12) For examining the pH dependency of the extraction of platinum from an aqueous potassium tetrachloroplatinate solution (0.1 mmol/L) by 1-(4-bromophenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide and 1-(4-ethoxyphenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide, different aqueous solutions with defined pH values are provided. Each 30 mL of the aqueous solution are contacted with 100 L of ionic liquid and kept in agitation for 2 hours by use of a Vibramax 100 from Heidolph at 1200 rpm. After a certain time interval, samples are taken from the aqueous phase and contacted with each 10 L of concentrated HNO.sub.3 (this serves to stabilize Pt in the solution). The concentration of cations is determined by ICP-MS.

(13) TABLE-US-00004 TABLE 4 Extraction ratios E in % at different pH values for 1-(4- bromophenyl)-3-undecyl-imidazoliumbis(trifluoromethyl- sulfonyl)imide and 1-(4-ethoxyphenyl)-3-undecyl-imidazo- liumbis(trifluoromethylsulfonyl)imide 1-(4-bromophenyl)-3-undecyl- 1-(4-ethoxyphenyl)-3-undecyl- imidazoliumbis(trifluoro- imidazoliumbis(trifluoro- methylsulfonyl)imide methylsulfonyl)imide pH E % pH E % 7.2 85.1 7.2 75 2.6 73.7 2.6 51 2.1 63.0 1.2 61.1 1.2 40

(14) The inventive extraction is possible not only in the neutral range but also in the acidic range. This can be gathered from table 4, the extraction performance decreases by 47% for 1-(4-ethoxyphenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide and by not even 29% for 1-(4-bromophenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide. Therefore, one can argue for a stable extraction performance over the whole pH range.

Example 4

Extraction of Different Metals

(15) For examining the extraction of further metals, iridium and europium are extracted exemplarily from an aqueous solution having a 0.1 mmol/L concentration of each metal (IrCl.sub.3 and EuCl.sub.3, respectively) by 1-(4-bromophenyl)-3-undecylimidazoliumbis-(trifluoromethylsulfonyl)imide. For this purpose, two different aqueous solutions (pH approx. 6.9) are provided and to each 30 mL of aqueous solution are added 100 L of ionic liquid. The mixtures are kept in agitation for 2 hours by use of a Vibramax 100 from Heidolph at 1200 rpm. After a certain time interval, samples are taken from the aqueous phase and contacted with each 10 L of concentrated HNO.sub.3 (this serves to stabilize Pt in the solution). The concentration of cations is determined by ICP-MS.

(16) TABLE-US-00005 TABLE 5 Extraction ratio E in % for 1-(4-bromophenyl)-3-undecyl- imidazoliumbis(trifluoromethylsulfonyl)imide Solution E % IrCl.sub.3 solution 75 EuCl.sub.3 solution 61

(17) Table 5 shows that not only platinum but also other metals may be extracted with the inventive process. Furthermore, it becomes apparent that the inventive process may not only be applied to heavy metals, such as iridium, but also shows very good results for the extraction of rare earths and actinides as, for example, europium.

Example 5

Selective Extraction (I)

(18) For examining the selective metal extraction, an aqueous solution containing a mixture of nickel nitrate and potassium hexachloroplatinate with a metal concentration of each 0.1 mmol/L is provided. The pH value of the solution is approx. 6.9. 30 mL of this solution are contacted with 100 L of 1-(4-bromophenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide. The mixture is kept in agitation for 2 hours by use of a Vibramax 100 from Heidolph at 1200 rpm. After a certain time interval, samples are taken from the aqueous phase and contacted with each 10 L of concentrated HNO.sub.3 (this serves to stabilize Pt in the solution). The concentration of cations is determined by ICP-MS

(19) TABLE-US-00006 TABLE 6 Extraction ratios E in % for 1-(4-bromophenyl)-3-undecyl- imidazolium-bis(trifluoromethylsulfonyl)imide with a mixture of Ni and Pt salts Metal E % Pt 96.1 Ni 0

(20) Table 6 clearly shows that the inventive process allows for a selective extraction. From a mixture of platinum and nickel, only platinum is extracted with an extraction ratio of 96.1%, whereas nickel remains in the aqueous phase.

Example 6

Selective Extraction (II)

(21) For examining the selective metal extraction, 3 different metal salt solutions are provided each containing nickel nitrate, iron trichloride or iridium trichloride with a metal salt concentration of each 0.1 mmol/L. The pH value of the solutions in 6.9. Each 30 mL of these mixtures are each contacted with 100 L of 1-(4-bromophenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide or 1-(4ethoxyphenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide. The mixtures are kept in agitation for 2 hours by use of a Vibramax 100 from Heidolph at 1200 rpm. After a certain time interval, samples are taken from the aqueous phase and contacted with each 10 L of concentrated HNO.sub.3. The concentration of cations is determined by ICP-MS.

(22) TABLE-US-00007 TABLE 7 Extration ratios E in % for 1-(4-bromophenyl)-3-undecyl- imidazoliumbis(trifluoromethylsulfonyl)imide and 1- (4-ethoxyphenyl)-3-undecyl-imidazoliumbis(trifluormethyl- sulfonyl)imide 1-(4-bromphenyl)-3-undecyl- 1-(4-ethoxyphenyl)-3-undecyl- imidazoliumbis(trifluoro- imidazoliumbis(trifluoro- methylsulfonyl)imide methylsulfonyl)imide Metal E % E % Fe 6.4 0 Ni 0.1 1.1 Ir 75.0 66.0

(23) Table 7 clearly shows that the tested ionic liquids selectively remove iridium from the aqueous phase, whereas iron and nickel remain in the aqueous solution. Therefore, the inventive process allows for the separation of, for example, iridium from a mixture of iridium, iron and nickel salts.

Example 7

Selective Extraction from Industrial Waste Water (III)

(24) For examining the selective metal extraction from industrial water, industrial water containing the following metals is used: Ag, Al, Au, Ca, Cu, Fe, Ir, Mg, Ni, Pb, Pd, Pt, Rh, Si, Sn, Zn. The industrial water is strongly acidic with a pH value of 0.41. 30 mL of the industrial waste water is contacted with 100 L of an ionic liquid (IL) and agitated with a GFL 3005 shaker at 300 rpm at room temperature. Shortly after addition of the IL to the industrial water and after an incubation period of 2 hours, samples are taken from the aqueous phase. A blank is monitored in parallel to the samples. The following ionic liquids are used in the experiment: 1-(4-methoxyphenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide, 1-(4-bromophenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide, 1-(2-methoxy-4-nitrophenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide and, for comparison, the commercially available ionic liquid 1-butyl-3-methyl-imidazoliumbis(trifluoromethylsulfonyl)imide [BMIM][N(Tf).sub.2]. In contrast to the inventive ionic liquids, [BMIM][N(Tf).sub.2] dissolves completely in the aqueous phase. A separation cannot be observed. For the inventive ionic liquids, a colour change from originally yellow-brown shades into darker brown shades can be observed.

(25) TABLE-US-00008 TABLE 8 Extraction results for different ionic liquids from acidic industrial waters (in mg/l) 1-(4-methoxyphenyl)-3- 1-(4-bromphenyl)-3- 1-(2-methoxy-4-nitrophenyl)- undecyl-imidazoliumbis- undecyl-imidazoliumbis- 3-undecyl-imidazoliumbis- (trifluoromethylsulfonyl)- (trifluoromethylsulfonyl)- (trifluoromethylsulfonyl)imide imide imide Element 0 h 2 h 0 h 2 h 0 h 2 h Mg 2.4 2.4 2.3 2.3 2.4 2.4 Al 10.6 10.2 10.7 10.4 10.7 10.6 Si 4.0 3.1 4.8 3.7 4.0 4.5 Ca 12.9 12.5 12.5 12.2 12.5 12.5 Fe 41.2 39.7 40.8 40.4 40.7 40.6 Ni 9.8 9.8 10.0 10.0 9.8 9.9 Cu 1960 1950 1980 1965 1965 1950 Zn 2.0 2.0 2.1 2.0 2.1 2.0 Rh 7.5 7.5 7.6 7.4 7.7 7.4 Pd 60.0 57.4 55.2 54.7 55.4 37.1 Ag 0.7 0.7 0.7 0.7 0.7 0.3 Sn 1.8 1.8 1.8 1.8 1.8 1.8 Ir 0.03 0.03 0.03 0.03 0.03 0.03 Pt 50.6 46.0 51.4 40.5 51.7 14.4 Au 28.9 12.0 18.4 13.0 27.3 2.0 Pb 62.0 62.2 62.2 63.0 59.8 62.7 1-butyl-3-methyl- imidazoliumbis- (trifluoromethylsufonyl)- Blank imide Element 0 h 2 h 0 h 2 h Mg 2.4 2.3 2.4 2.4 Al 10.6 10.5 10.5 10.5 Si 4.8 3.6 4.2 3.6 Ca 12.5 12.5 12.1 12.7 Fe 40.4 40.4 40.5 40.3 Ni 9.9 9.8 9.8 10.0 Cu 1950 1965 1950 1985 Zn 2.1 2.0 2.1 2.0 Rh 7.8 7.4 7.7 7.6 Pd 61.5 60.6 60.0 60.9 Ag 0.7 0.7 0.7 0.7 Sn 1.8 1.8 1.8 1.8 Ir 0.03 0.03 0.03 0.03 Pt 53.6 52.9 53.1 54.0 Au 41.9 41.8 40.6 42.9 Pb 62.1 60.8 60.7 62.1

(26) If one compares the conventional ionic liquid [BMIM][N(Tf).sub.2] with the blank, it can be observed that it is completely inactive with respect to metal extraction from strongly acidic industrial water. In contrast thereto, the inventive ionic liquids also show activity in a strongly acidic environment. Therefore, with 1-(2-methoxy-4-nitrophenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide one can extract Au, with 1-(4-methoxyphenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide one can extract Au and Pt and with 1-(4-bromophenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide one can extract Au, Pt and Pf. One can imagine to use this selectivity for a separation of metals in an extraction cascade. By using 1-(2-methoxy-4-nitrophenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide it is possible to separate Au followed by 1-(4-methoxyphenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide (separation of Pt) and 1-(4-bromophenyl)-3-undecyl-imidazoliumbis(trifluoromethylsulfonyl)imide (separation of Pd).

Synthesis of the Used Ionic Liquids

1-Phenyl-3-butyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(27) (C.sub.15H.sub.17F.sub.6N.sub.3O.sub.4S.sub.2, 481.434 g/mol)

(28) ##STR00004##
2.74 g (8.4 mmol) 1-Phenyl-3-butylimidazoliumiodide and 2.88 g (10 mmol) lithium bis(trifluoromethylsulfonyl)amide are dissolved in 100 mL methanol-water mixture and contacted with 10 mL dichloromethane. The reaction mixture was stirred at room temperature for 24 hours and the organic phase is separated subsequently. After removal of the solvent, an oily liquid was obtained (97% yield, 3.9 g).

(29) Thermic stabilty: decomposition onset: 305 C., inflection point: 435 C.

(30) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 9.00 (1H, s, NCHN), 7.59 (1H, m, NCHC), 7.49 (6H, m, CH arom., NCHC), 4.22 (2H, t, J=7.6 Hz, NCH.sub.2), 1.84 (2H, m, CH.sub.2), 1.34 (2H, m, CH.sub.2), 0.89 (3H, t, J=7.2 Hz, CH.sub.3)

(31) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 134.2 (C), 133.8 (NCHN), 130.5 (CH), 123.4 (CH), 122.0 (CH), 121.7 (CH), 50.4 (CH.sub.2), 31.9 (CH.sub.2), 19.3 (CH.sub.2), 13.2 (CH.sub.3)

(32) Elementary analysis (C.sub.15H.sub.17F.sub.6N.sub.3O.sub.4S.sub.2):

(33) calcd.: C, 37.42%, H, 3.56%, N, 8.73%, S, 13.32%.

(34) found: C, 37.59%, H, 3.61%, N, 8.94%, S, 12.91%.

1-Phenyl-3-hexyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(35) (C.sub.17H.sub.21F.sub.6N.sub.3O.sub.4S.sub.2, 509.487 g/mol)

(36) ##STR00005##
3.42 g (9.6 mmol) 1-phenyl-3-hexylimidazoliumiodide and 3.31 g (11.5 mmol) lithium bis(trifluoromethylsulfonyl)amide are dissolved in 100 mL methanol-water mixture and contacted with 10 mL dichloromethane. The reaction mixture was stirred at room temperature for 24 hours and the organic phase is separated subsequently. After removal of the solvent, an oily liquid was obtained (yield 98%, 4.81 g).

(37) Thermic stabilty: decomposition onset: 308 C., inflection point: 440 C.

(38) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 9.01 (1H, s, NCHN), 7.59 (1H, m, NCHC), 7.49 (6H, m, CH arom., NCHC), 4.22 (2H, t, J=7.7 Hz, NCH.sub.2), 1.86 (2H, m, CH.sub.2), 1.25 (6H, m 3xCH.sub.2), 0.79 (3H, t, J=6.9 Hz, CH.sub.3)

(39) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 134.3 (C), 133.8 (NCHN), 130.6 (CH), 123.3 (CH), 122.0 (CH), 121.9 (CH), 121.7 (CH), 50.6 (CH.sub.2), 30.9 (CH.sub.2), 29.9 (CH.sub.2), 25.7 (CH.sub.2), 22.2 (CH.sub.2), 13.8 (CH.sub.3)

(40) Elementary analysis (C.sub.17H.sub.21F.sub.6N.sub.3O.sub.4S.sub.2):

(41) calcd.: C, 40.08%, H, 4.15%, N, 8.25%, S, 12.59%.

(42) found: C, 40.16%, H, 3.81%, N, 8.37%, S, 12.68%.

1-Phenyl-3-undecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(43) (C.sub.22H.sub.31F.sub.6N.sub.3O.sub.4S.sub.2, 579.619 g/mol)

(44) ##STR00006##

(45) 5.76 g (13.5 mmol) 1-phenyl-3-undecylimidazoliumiodide and 4.65 g (16.2 mmol) lithium bis(trifluoromethylsulfonyl)amide are dissolved in 100 mL methanol-water mixture and contacted with 10 mL dichloromethane. The reaction mixture was stirred at room temperature for 24 hours and the organic phase is separated subsequently. After removal of the solvent, an oily liquid was obtained (yield 79%, 6.2 g).

(46) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 9.12 (1H, s, NCHN), 7.60 (1H, m, NCHC), 7.50 (6H, m, NCHC, CH arom.), 4.25 (2H, t, J=7.7 Hz, NCH.sub.2), 1.87 (2H, m, CH.sub.2), 1.22 (16H, m, 8xCH.sub.2), 0.79 (3H, t, J=6.8 Hz, CH.sub.3)

(47) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 134.3 (NCHN), 133.9 (C), 130.6 (CH), 123.3 (CH), 122.0 (CH), 121.6 (CH), 50.7 (NCH.sub.2), 31.8 (CH.sub.2), 30.1 (CH.sub.2), 29.5 (CH.sub.2), 29.4 (CH.sub.2), 29.3 (CH.sub.2), 29.2 (CH.sub.2), 28.8 (CH.sub.2), 26.1 (CH.sub.3)

(48) Elementary analysis (C.sub.22H.sub.31F.sub.6N.sub.3O.sub.4S.sub.2.0.25 EtOAc):

(49) calcd.: C, 25.93%, H, 5.53%, N, 6.97%, S, 10.64%.

(50) found: C, 46.16%, H, 4.87%, N, 6.97%, S, 9.63%.

1-Phenyl-3-tetradecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(51) (C.sub.25H.sub.37F.sub.6N.sub.3O.sub.4S.sub.2, 621.699 g/mol)

(52) ##STR00007##
2.11 g (5 mmol) 1-phenyl-3-tetradecylimidazoliumbromide and 1.72 g (6 mmol) lithium bis(trifluoromethylsulfonyl)amide are dissolved in 30 mL of methanol-water mixture and contracted with 10 mL of dichloromethane. The reaction mixture was stirred at room temperature for 24 hours and the organic phase is separated subsequently. After removal of the solvent, an oily liquid was obtained (yield 93%, 2.89 g).

(53) .sup.1H-NMR 300 MHz, CDCl.sub.3, ppm): 9.01 (1H, s, NCHN), 7.60 (1H, t, J=1.9 Hz, NCHC), 7.49 (6H, m, NCHC, CH arom.), 4.23 (2H, t, J=7.6 Hz, NNC.sub.2), 1.86 (2H, m, CH.sub.2), 1.22 (22H, m, 11xCH.sub.2), 0.79 ppm (3H, t, J=6.9 Hz, CH.sub.3)

(54) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 134.4 (C arom.), 133.9 (NCHN), 130.6 (CH), 123.3 (CH), 122.1 (CH), 121.7 (CH), 50.7 (NCH.sub.2), 31.9 (CH.sub.2), 30.1 (CH.sub.2), 29.6 (CH.sub.2), 29.5 (CH.sub.2), 29.4 (CH.sub.2), 29.3 (CH.sub.2), 28.9 (CH.sub.2), 26.1 (CH.sub.2), 22.6 (CH.sub.2), 14.1 (CH.sub.3)

(55) Elementary analysis (C.sub.25H.sub.37F.sub.6N.sub.3O.sub.4S.sub.2):

(56) calcd.: C, 48.30%, H, 6.00%, N, 6.76%, S, 10.32%.

(57) found: C, 48.48%, H, 6.26%, N, 6.94%, S, 10.20%.

1-(4-Methoxyphenyl)-3-methyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(58) (C.sub.13H.sub.13F.sub.6N.sub.3O.sub.5S.sub.2, 469.379 g/mol)

(59) ##STR00008##
8.68 g (0.027 mol) 1-(4-methoxyphenyl)-3-methylimidazoliumiodide and 7.8 g (0.027 mol) lithium bis(triflouoromethylsulfonyl)amide are dissolved in 160 mL water and 25 mL dichloromethane are added. After stirring for 1 hour at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product is obtained in 100% yield.

(60) Thermic stabilty: decomposition onset: 305 C., inflection point: 460 C.

(61) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.63 (1H, s, NCHN), 8.20 (1H, m, NCCH), 7.91 (1H, m, NCCH), 7.66 (2H, m, CH arom.), 7.21 (2H, m, CH arom.), 3.93 (3H, s, NCH.sub.3), 3.85 (3H, s, OCH.sub.3)

(62) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 160.0 (C arom.), 135.7 (NCHC), 127.9 (C arom.), 124.2 (CH), 123.5 (2CH), 121.3 (CH), 115.2 (2CH), 55.7 (ArOCH3), 36.0 (NCH.sub.3)

(63) Elementary analysis (C.sub.13H.sub.13F.sub.6N.sub.3O.sub.5S.sub.2)

(64) calcd.: C, 33.26%, H, 2.79%, N, 8.95%, S, 13.66%.

(65) found: C, 33.08%, H, 2.77%, N, 8.83%, S, 13.70%.

1-(4-Methoxyphenyl)-3-butyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(66) (C.sub.16H.sub.19FN.sub.3O.sub.5S.sub.2, 511.459 g/mol)

(67) ##STR00009##
9.69 g (0.027 mol) 1-(4-methoxyphenyl)-3-butyl-1H-imidazoliumiodide and 9.32 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 160 mL water and 25 mL dichloromethane are added. After stirring for 20 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product is obtained in 100% yield.

(68) Thermic stabilty: decomposition onset: 289 C., inflection point: 460 C.

(69) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.72 (m, 1 H, NCHN), 8.24 (m, 1 H, NCHC), 8.02 (m, 1 H, NCHC), 7.72 (d, J=9 Hz, 2 H, arom. CH), 7.21 (d, J=9 Hz, 2 H, arom. CH), 4.25 (t, J=7.2 Hz, 2 H, NCH.sub.2), 3.86 (s, 3 H, OCH.sub.3), 1.89 (m, 2 H, CH.sub.2), 1.35 (m, 2 H, CH.sub.2), 0.95 (t, J=7.4 Hz, 3 H, CH.sub.3)

(70) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 160.0 (arom. C), 135.1 (arom. CH), 127.9 (arom. C), 123.5 (arom. CH), 123.1 (arom. CH), 121.6 (arom. CH), 115.1 (arom. CH), 55.7 (OCH.sub.3), 49.1 (NCH.sub.2), 31.1 (CH.sub.2), 18.9 (CH.sub.2), 13.2 (CH.sub.3)

(71) Elementary analysis (C.sub.16H.sub.19FN.sub.3O.sub.5S.sub.2)

(72) calcd.: C, 37.57%, H, 3.74%, N, 8.22%, S, 12.54%.

(73) found: C, 37.69% H, 3.54% N, 8.53%, S, 12.50%.

1-(4-Methoxyphenyl)-3-hexyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(74) (C.sub.18H.sub.23F.sub.6N.sub.3O.sub.5S.sub.2, 539.513 g/mol)

(75) ##STR00010##
13.25 g (0.036 mol) 1-(4-methoxyphenyl)-3-hexyl-1H-imidazoliumbromide and 13.45 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 160 mL water and 25 mL dichloromethane are added. After stirring for 20 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product is obtained in 100% yield.

(76) Thermic stabilty: decomposition onset: 314 C., inflection point: 460 C.

(77) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.71 (1H, s, NCHN), 8.24 (1H, m, NCHC), 8.02 (1H, m, NCHC), 7.72 (2H, d, J=9 Hz, CH arom.), 7.21 (2H, d, J=9 Hz, CH arom.), 4.24 (2H, q, J=7 Hz, NCH.sub.2), 3.86 (3H, s, OCH.sub.3), 1.90 (2H, m, CH.sub.2), 1.33 (6H, m, 3xCH.sub.2), 0.89 (3H, m, CH.sub.3)

(78) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO): 160.0 (C-Aromat), 135.0 (NCHN), 127.9 (C arom.), 123.5 (2CH), 123.1 (CH), 121.5 (CH), 115.1 (2CH), 55.7 (OCH.sub.3), 49.3 (NCH.sub.2), 30.6 (CH.sub.2), 29.12 (CH.sub.2), 25.2 (CH.sub.2), 21.8 (CH.sub.2), 13.8 (CH.sub.3)

(79) Elementary analysis (C.sub.18H.sub.23F.sub.6N.sub.3O.sub.5S.sub.2)

(80) calcd.: C, 40.07%, H, 4.30%, N, 7.79%, S, 11.89%.

(81) found: C, 39.91%, H, 4.45%, N, 7.71%, S, 11.71%.

1-(4-Methoxyphenyl)-3-undecyl-1H-imidazoliumbis(trifuluoromethyl)sulfonylimide

(82) (C.sub.23H.sub.33F.sub.6N.sub.3O.sub.5S.sub.2, 609.646 g/mol)

(83) ##STR00011##
2.861 g (6.26 mmol) 1-(4-methoxyphenyl)-3-undecyl-1H-imidazoliumiodide and 2.16 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in a water-methanol mixture and 10 mL dichloromethane are added. After stirring for 20 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product (melting point 21 C.) is obtained in 100% yield.

(84) Thermic stabilty: decomposition onset: 262 C., inflection point: 440 C.

(85) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 8.98 (1H, m, NCHN), 7.52 (1H, m, NCHC), 7.43 (3H, m, NCHC arom, CH), 6.96 (2H, d, J=9.06 Hz, arom. CH), 4.22 (2H, t, J=7.6 Hz, NCH.sub.2), 3.78 (3H, s, ArOCH.sub.3), 1.86 (2H, m, CH.sub.3), 1.22 (16H, m, 8xCH.sub.2), 0.79 (3H, m, CH.sub.3)

(86) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 161.0 (C), 133.8 (NCHN), 127.2 (C), 123.6 (CH), 122.9 (CH), 121.8 (CH), 115.5 (CH), 55.7 (CH.sub.3), 50.5 (CH.sub.2), CH.sub.2 31.8, 30.1, 29.5, 29.4, 29.3, 29.2, 28.8, 26.1, 22.6, 14.0 (CH.sub.3)

(87) Elementary analysis (C.sub.23H.sub.33F.sub.6N.sub.3O.sub.5S.sub.2)

(88) calcd.: C, 45.31%, H, 5.46%, N, 6.89%, S, 10.52%.

(89) found: C, 45.62%, H, 5.37%, N, 7.03%, S, 9.58%.

1-(4-Methoxyphenyl)-3-tetradecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(90) (C.sub.26H.sub.39F.sub.6N.sub.3O.sub.5S.sub.2, 651.725 g/mol)

(91) ##STR00012##
4.061 g (8.99 mmol) 1-(4-methoxyphenyl)-3-tetradecyl-1H-imidazolium-bromide and 2.58 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in a water-methanol mixture and 10 mL dichloromethane are added. After stirring for 20 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator.

(92) The liquid product is obtained in 92% yield (5.41 g).

(93) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.69 (1H, s, NCHN), 8.24 (1H, s, NCHC), 8.01 (1H, s, NCHC), 7.70 (2H, d, J=8.9 Hz, ArH), 7.20 (2H, d, J=8.9 Hz, ArH), 4.22 (2H, t, J=7.4 Hz, NCH.sub.2), 3.85 (3H, s, ArOCH.sub.3), 1.88 (2H, m, CH.sub.2), 1.27 (22H, m, 11xCH.sub.2), 0.85 (3H, m, CH.sub.3)

(94) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 159.9 (C), 135.0 (NCHN), 127.9 (C), 123.4 (2CH), 123.1 (CH), 121.4 (CH), 115.1 (2CH), 55.7 (ArOCH.sub.3), 49.3 (NCH.sub.2), 31.3 29.1 28.9 28.8 28.7 28.4 25.5 22.1 (CH.sub.2), 13.9 (CH.sub.3)

(95) Elementary analysis (C.sub.26H.sub.39F.sub.6N.sub.3O.sub.5S.sub.2)

(96) calcd.: C, 47.92%, H, 6.03%, N, 6.45%, S, 9.84%.

(97) found: C, 48.20%, H, 6.38%, N, 6.64%, S, 8.86%.

1-(2-Methoxyphenyl)-3-hexyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(98) (C.sub.18H.sub.23F.sub.6N.sub.3O.sub.5S.sub.2, 539.513 g/mol)

(99) ##STR00013##
1.34 g (3.5 mmol) 1-(2-methoxyphenyl)-3-hexyl-1H-imidazoliumiodide and 1.2 g (4.2 mmol) lithium bis(trifluoromethylsulfonyl)amide are dissolved in a mixture of 80 mL of water and 20 mL of methanol and 25 mL of dichloromethane are added. After staring for 24 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product is obtained in 96% yield (1.8 g).

(100) Thermic stabilty: decomposition onset: 280 C., inflection point: 440 C.

(101) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 8.84 (1H, s, NCHN), 7.45 (2H, m, NCHC), 7.42 (1H, m, CH arom.), 7.36 (1H, m, CH arom.), 7.04 (2H, m, CH arom.), 4.22 (2H, t, J=7.6 Hz, NCH.sub.2), 3.82 (3H, s, OCH.sub.3), 1.85 (2H, m, CH.sub.2), 1.25 (6H, m, 3xCH.sub.2), 0.80 (3H, t, J=6.9 Hz, CH.sub.3)

(102) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 151.9 (C arom), 135.9 (NCHN), 131.9 (CH), 123.3 (CH), 123.6 (CH), 122.9 (C arom.), 121.9 (CH), 121.5 (CH), 113.4 (CH), 56.1 (OCH.sub.3), 50.4 (CH.sub.2), 30.9 (CH.sub.2), 29.9 (CH.sub.2), 25.6 (CH.sub.2), 22.3 (CH.sub.2), 13.7 (CH.sub.3)

(103) Elementary analysis (C.sub.18H.sub.23F.sub.6N.sub.3O.sub.5S.sub.2)

(104) calcd.: C, 40.07%, H, 4.30%, N, 7.79%, S, 11.89%.

(105) found: C, 40.11%, H, 4.13%, N, 7.93%, S, 11.92%.

1-(2-Methoxyphenyl)-3-undecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(106) (C.sub.23H.sub.33F.sub.6N.sub.3O.sub.5S.sub.2, 609.646 g/mol)

(107) ##STR00014##
0.94 g (2.6 mmol) 1-(2-methoxyphenyl)-3-undecyl-1H-imidazoliumiodide and 0.88 g (3.1 mmol) lithium bis(trifluoromethylsulfonyl)amide are dissolved in a mixture of 40 mL of water and 10 mL of methanol and 10 mL of dichloromethane added. After stirring for 24 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product (melting point 28 C.) is obtained in 84% yield (1.06 g).

(108) Thermic stabilty: decomposition onset: 190 C., inflection point: 430 C.

(109) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.59 (1H, s, NCHN), 8.08 (1H, s, NCHC), 8.01 (1H, s, NCHC), 7.62 (2H, m, CH arom.), 7.40 (1H, m, CH arom.), 7.20 (1H, m, CH arom.), 4.27 (2H, t, J=7.2 Hz, NCH.sub.2), 3.89 (3H, s, OCH.sub.3), 1.89 (2H, m, CH.sub.2), 1.29 (16H, m, 8xCH.sub.2), 0.86 (3H, m, CH.sub.3)

(110) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 152.2 (C), 137.1 (NCHN), 131.6 (CH), 126.2 (CH), 123.8 (CH), 123.4 (C), 122.2 (CH), 121.6 (CH), 113.2 (CH), 56.3 (OCH.sub.3), 49.2 (NCH.sub.2), CH.sub.2: 31.3, 29.2, 28.9, 28.8, 28.7, 28.3, 25.5, 22.1, 13.9 (CH.sub.3)

(111) Elementary analysis (C.sub.23H.sub.33F.sub.6N.sub.3O.sub.5S.sub.2)

(112) calcd.: C, 45.31%, H, 5.46%, N, 6.89%, S, 10.52%.

(113) found: C, 45.34%, H, 5.58%, N, 7.24%, S, 10.35%.

1-(2-Methoxyphenyl)-3-tetradecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(114) (C.sub.26H.sub.39F.sub.6N.sub.3O.sub.5S.sub.2, 651.725 g/mol)

(115) ##STR00015##
2.25 g (5 mmol) 1-(2-methoxyphenyl)-3-tetradecyl-1H-imidazoliumiodide and 1.72 g (6 mmol) lithium bis(trifluoromethylsulfonyl)amide are dissolved in a mixture of 30 mL of water and 30 mL of methanol and 10 mL of dichloromethane are added. After stirring for 24 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product is obtained in 94% yield (3.08 g).

(116) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 8.85 (1H, s, NCHN), 7.54 (3H, m, CH arom., NCHC), 7.38 (1H, m, CH arom.), 7.03 (1H, m, CH arom.), 4.22 (2H, t, J=7.6 Hz, NCH.sub.2), 3.82 (3H, s, OCH.sub.3), 1.85 (2H, m, CH.sub.2), 1.20 (22H, m, CH.sub.2), 0.79 (3H, t, J=6.8 Hz, CH.sub.3),

(117) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 152.0 (C), 135.9 (NCHN), 131.9 (CH), 125.3 (CH), 123.6 (CH), 122.9 (C), 121.9 (CH), 121.5 (CH), 112.6 (CH), 56.1 (CH3), 50.4 (CH.sub.2), 31.8 (CH.sub.2), 30.0 (CH.sub.2), 29.6 (CH.sub.2), 29.5 (CH.sub.2), 29.4 (CH.sub.2), 29.3 (CH.sub.2), 28.8 (CH.sub.2), 28.7 (CH.sub.2), 28.1 (CH.sub.2), 26.0 (CH.sub.2), 22.6 (CH.sub.2), 14.0 (CH.sub.3)

(118) Elementary analysis (C.sub.26H.sub.39F.sub.6N.sub.3O.sub.5S.sub.2)

(119) calcd.: C, 47.92%, H, 6.03%, N, 6.45%, S, 9.84%.

(120) found: C, 48.14%, H, 5.84%, N, 6.55%, S, 8.96%.

1-(4-Ethoxyphenyl)-3-propyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(121) (C.sub.16H.sub.19F.sub.6N.sub.3O.sub.5S.sub.2, 511.459 g/mol)

(122) ##STR00016##
7.91 g (0.025 mol) 1-(4-ethoxyphenyl)-3-propyl-1H-imidazoliumbromide and 7.29 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 100 mL of water and 25 mL of dichloromethane are added. After stirring for 20 hours at room temperature, the organic phase is separated and concentrated on the rotary operator. The liquid product (the melting point 20 C.) is obtained in 98% yield (12.77 g).

(123) Thermic stabilty: decomposition onset: 320 C., inflection point: 450 C.

(124) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.71 (1H, s, NCHN), 8.24 (1H, m, NCHC), 8.01 (1H, m, NCHC), 7.69 (2H, d, J=9 Hz, ArH), 7.19 (2H, d, J=9 Hz, ArH), 4.21 (2H, t, J=7.4 Hz, NCH.sub.2), 4.13 (2H, q, J=6.8 Hz, OCH.sub.2), 1.92 (2H, m, CH.sub.2), 1.37 (3H, t, J=6.9 Hz, CH.sub.3), 0.94 (3H, t, J=7.4, CH.sub.3)

(125) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO): 159.3 (C), 135.1 (NCHN), 127.7 (C), 123.5 (2CH), 123.1 (C), 121.6 (C), 115.5 (2CH), 63.7 (CH.sub.2), 50.8 (CH.sub.2), 22.7 (CH.sub.2), 14.4 (CH.sub.3), 10.4 (CH.sub.3)

(126) Elementary analysis (C.sub.16H.sub.19F.sub.6N.sub.3O.sub.5S.sub.2)

(127) calcd.: C, 37.57%, H, 3.74%, N, 8.22%, S, 12.54%.

(128) found: C, 37.46%, H, 3.81%, N, 8.41%, S, 12.72%.

1-(4-Ethoxyphenyl)-3-butyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(129) (C.sub.17H.sub.21F.sub.6N.sub.3O.sub.5S.sub.2, 525.486 g/mol)

(130) ##STR00017##
10.07 g (0.031 mol) 1-(4-ethoxyphenyl)-3-butyl-1H-imidazoliumbromide and 8.89 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 160 mL of water and 25 mL of dichloromethane are added. After stirring for 3 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product (melting point 6 C.) is obtained in 100% yield (16.08 g).

(131) Thermic stabilty: decomposition onset: 311 C., inflection point: 450 C.

(132) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.71 (1H, s, NCHN), 8.23 (1H, s, NCHC), 8.01 (1H, s, NCHC), 7.69 (2H, d, J=9 Hz, CH arom.), 7.18 (2H, d, J=9 Hz, CH arom.), 4.25 (2H, t, J=7.2, NCH.sub.2), 4.13 (2H, t, J=7 Hz, OCH.sub.2), 1.89 (2H, m, CH.sub.2), 1.37 (5H, m, CH.sub.3+CH.sub.2), 0.95 (3H, t, J=7.4)

(133) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 159.3 (C), 135.0 (NCHN), 123.5 (2CH), 123.1 (CH), 121.6 (CH), 115.5 (2CH), 63.7 (CH.sub.2), 49.1 (CH.sub.2), 31.2 (CH.sub.2), 18.9 (CH.sub.2), 14.4 (CH.sub.3), 13.2 (CH.sub.3)

(134) Elementary analysis (C.sub.17H.sub.21F.sub.6N.sub.3O.sub.5S.sub.2)

(135) calcd.: C, 38.86%, H, 4.03%, N, 8.00% S, 12.20%.

(136) found: C, 38.72%, H, 3.99%, N, 8.19%, S, 12.43%.

1-(4-Ethoxyphenyl)-3-pentyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(137) (C.sub.18H.sub.23F.sub.6N.sub.3O.sub.5S.sub.2, 539.513 g/mol)

(138) ##STR00018##
10.29 g (0.03 mol) 1-(4-ethoxyphenyl)-3-pentyl-1H-imidazoliumbromide and 8.71 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 160 mL of water and 25 mL of dichloromethane are added. After stirring for 1 hour at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product (glass transition temperature 58 C.) is obtained in 100% yield (16.63 g).

(139) Thermic stabilty: decompositin onset: 307 C., inflection point: 440 C.

(140) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.71 (1H, s, NCHN), 8.24 (1H, s, NCHC), 8.01 (1H, s, NCHC), 7.69 (2H, d, J=9 Hz, ArH), 7.19 (2H, d, J=8.9 Hz ArH), 4.23 (2H, t, J=7.4 Hz, NH.sub.2), 4.12 (2H, q, J=6.9 Hz, OCH.sub.2), 1.91 (2H, m, CH.sub.2), 1.35 (7H, m, CH.sub.3+2xCH.sub.2), 0.91 (3H, t, J=7 Hz, CH.sub.3)

(141) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 159.3 (C), 135.0 (NCHN), 127.7 (C), 123.5 (2CH), 123.1 (CH), 121.6 (CH), 115.5 (2CH), 63.7 (CH.sub.2), 49.3 (CH.sub.2), 28.9 (CH.sub.2), 27.7 (CH.sub.2), 21.5 (CH.sub.2), 14.4 (CH.sub.3), 13.6 (CH.sub.3)

(142) Elementary analysis (C.sub.18H.sub.23F.sub.6N.sub.3O.sub.5S.sub.2)

(143) calcd.: C, 40.07%, H, 4.30%, N, 7.79%, S, 11.89%.

(144) found: C, 39.75%, H, 4.03%, N, 7.77%, S, 12.14%.

1-(4-Ethoxyphenyl)-3-hexyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(145) (C.sub.19H.sub.25F.sub.6N.sub.3O.sub.5S.sub.2, 553.539 g/mol)

(146) ##STR00019##
11.85 g (0.034 mol) 1-(4-ethoxyphenyl)-3-hexyl-1H-imidazoliumbromide and 9.63 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 160 mL of water and 25 mL of dichloromethane are added. After stirring for 20 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product (melting point 27 C.) is obtained in 99% yield (18.45 g).

(147) Thermic stabilty: decomposition onset: 321 C., inflection point: 440 C.

(148) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.71 (1H, s, NCHN), 8.23 (1H, s, NCHC), 8.01 (1H, s, NCHC), 7.69 (2H, d, J=9 Hz, ArH), 7.19 (2H, d, J=9 Hz, ArH), 4.23 (2H, t, J=7.4 Hz, NCH.sub.2), 4.12 (2H, q, J=7 Hz, OCH.sub.2), 1.89 (2H, m, CH.sub.2), 1.37 (3H, t, J=7 Hz), 1.32 (6H, m, 3xCH.sub.2), 0.88 (3H, m, CH.sub.3),

(149) .sup.13 C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 159.3 (C), 135.0 (NCHN), 127.7 (C), 123.5 (2CH), 123.1 (CH), 121.6 (CH), 115.5 (2CH), 63.7 (OCH.sub.2), 49.3 (NCH.sub.2) 30.6 (CH.sub.2), 29.1 (CH.sub.2), 25.2 (CH.sub.2), 21.8 (CH.sub.2), 21.8 (CH.sub.2), 14.4 (CH.sub.3), 13.7 (CH.sub.3)

(150) Elementary analysis (C.sub.19H.sub.25F.sub.6N.sub.3O.sub.5.sub.S2)

(151) calcd.: C, 41.23%, H, 4.55%, N, 7.59%, S, 11.59%.

(152) found: C, 41.25%, H, 4.62%, N, 7.82%, S, 11.68%.

1-(4-Ethoxyphenyl)-3-undecyl-1H-imidazoliumbis(trifluorometyl)sulfonylimide

(153) (C.sub.24H.sub.35F.sub.6N.sub.3O.sub.5S.sub.2, 623.672 g/mol)

(154) ##STR00020##
5.71 g (0.012 mol) 1-(4-ethoxyphenyl)-3-undecyl-1H-imidazoliumiodide and 4.18 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 80 mL of water and 15 mL of dichloromethane are added. After stirring for 20 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product is obtained in 100% yield.

(155) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 8.91 (1H, s, NCHN), 7.49 (1H, m, NCHC), 7.42 (1H, m, NCHC), 7.40 (2H, d, J=9.1 Hz, CH arom.), 6.95 (2H, d, J=9.1 Hz, CH arom.), 4.21 (2H, t, J=7.7 Hz, NCH.sub.2), 4.00 (2H, q, J=6.9 Hz, OCH.sub.3), 1.85 (2H, m, CH.sub.2), 1.37 (3H, t, J=6.9 Hz, CH.sub.3), 1.22 (16H, m, 8xCH.sub.2), 0.79 (3H, t, J=6.9 Hz, CH.sub.3),

(156) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 160.5 (CO), 133.8 (NCHN), 126.2 (CN), 123.6 (2CH), 122.9 (CH), 121.9 (CH), 115.9 (CH), 64.1 OCH.sub.2) 50.6 (NCH.sub.2), (CH.sub.2: 31.8, 30.1, 29.5, 29.4, 29.3, 29.2, 28.9, 26.1, 22.6), 14.6 (CH.sub.3), 14.1 (CH.sub.3)

(157) Thermic stabilty: decomposition onset: 295 C., inflection point: 440 C.

(158) Elementary analysis (C.sub.24H.sub.35F.sub.6N.sub.3O.sub.5S.sub.2)

(159) calcd.: C, 46.22%, H, 5.66%, N, 6.74%, S, 10.28%.

(160) found: C, 46.15%, H, 4.78%, N, 6.91%, S, 9.99%.

1-(4-Ethoxyphenyl)-3-tetradecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(161) (C.sub.27H.sub.41F.sub.6N.sub.3O.sub.5S.sub.2, 665.752 g/mol)

(162) ##STR00021##
1.923 g (4.13 mmol) 1-(4-ethoxyphenyl)-3-tetradecyl-1H-imidazolium-bromide and 1.19 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 50 mL of water and 10 mL of dichloromethane. After stirring for 20 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator the liquid product (melting point 34 C.) is obtained in 89% yield (2.45 g).

(163) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.72 (1H, s, NCHN), 8.24 (1H, s, NCHC), 8.01 (1H, s, NCHC), 7.70 (2H, d, J=9 Hz, ArH), 7.18 (2H, d, J=9 Hz, ArH), 4.24 (2H, t, J=7.4 Hz, NCH.sub.2), 4.12 (2H, q, J=7 Hz, OCH.sub.2), 1.90 (2H, m, CH.sub.2), 1.37 (3H, t, J=7 Hz, CH.sub.3), 1.30 (24H, m, 12xCH.sub.2), 0.86 (3H, m, CH.sub.3)

(164) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 159.3 (C), 134.9 (NCHN), 127.7 (C), 123.4 (2CH), 123.1 (CH), 121.6 (CH), 115.5 (2CH), 63.7 OCH.sub.2), 49.3 (NCH.sub.2), 31.3 (CH.sub.2), 29.2 (CH.sub.2), 29.1 (CH.sub.2), 29.0 (CH.sub.2), 28.9 (CH.sub.2), 28.8 (CH.sub.2), 28.7 (CH.sub.2), 28.4 (CH.sub.2), 25.6 (CH.sub.2), 22.1 (CH.sub.2), 14.4 (CH.sub.3), 13.8 (CH.sub.3)

(165) Elementary analysis (C.sub.27H.sub.41F.sub.6N.sub.3O.sub.5S.sub.2)

(166) calcd.: C, 48.71%, H, 6.21%, N, 6.31%, S, 9.63%.

(167) found: C, 48.86%, H, 6.38%, N, 6.49%, S, 9.82%.

1-(2-Ethoxyphenyl)-3-butyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(168) (C.sub.17H.sub.21F.sub.6N.sub.3O.sub.5S.sub.2, 525.486 g/mol)

(169) ##STR00022##
5.73 g (15.4 mmol) 1-(2-ethoxyphenyl)-3-butylimidazoliumiodide and 5.31 g (18.5 mmol) lithium bis(trifluoromethylsulfonyl)amide are dissolved in 100 mL of a methanol-water mixture and 25 mL of methane are added. After stirring for 24 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product is obtained in 100% yield (8.16 g).

(170) Thermic stabilty: decomposition onset: 270 C., inflection point: 401 C.

(171) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 8.82 (1H, s, NCHN), 7.47 (1H, m, NCHC), 7.45 (1H, m, NCHC), 7.36 (2H, m, CH arom.), 7.01 (2H, m, CH arom.), 4.23 (2H, t, J=7.4 Hz, NCH.sub.2), 4.06 (2H, q, J=6.9 Hz, OCH.sub.2), 1.84 (2H, m, CH.sub.2), 1.32 (2H, m, CH.sub.2), 1.29 (3H, t, J=6.9 Hz, CH.sub.3), 0.89 (3H, t, J=7.4 Hz, CH.sub.3)

(172) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 151.33 (C arom.), 135.8 (NCHN), 131.9 (CH), 125.3 (CH), 123.6 (CH), 122.9 (CH), 122.0 (CH), 121.3 (CH), 113.3 (CH), 64.8 (CH.sub.2), 50.1 (CH.sub.2), 31.9 (CH.sub.2), 19.2 (CH.sub.2), 14.2 (CH.sub.3), 13.1 (CH.sub.3)

(173) Elementary analysis (C.sub.17H.sub.21F.sub.6N.sub.3O.sub.5S.sub.2)

(174) calcd: C, 38.86%, H, 4.03%, N, 7.89%, S, 12.20%.

(175) found: C, 38.15%, H, 4.35%, N, 7.92%, S, 11.65%.

1-(2-Ethoxyphenyl)-3-hexyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(176) (C.sub.19H.sub.25F.sub.6N.sub.3O.sub.5S.sub.2, 553.539 g/mol)

(177) ##STR00023##
5.13 g (12.8 mmol) 1-(2-Ethoxyphenyl)-3-hexylimidazoliumiodide and 4.41 g (15.4 mmol) lithium bis(trifluoromethylsulfonyl)amide are dissolved in 100 mL of a methanol-water mixture and 25 mL of dichloromethane are added. After stirring for 24 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product is obtained in 86% yield (6.11 g).

(178) Thermic stabilty: decomposition onset: 331 C., inflection point: 439 C.

(179) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 8.84 (1H, s, NCHN), 7.46 (2H, m, CH arom.), 7.37 (2H, m, CH arom.), 7.04 (1H, s, NCHC), 7.01 (1H, s, NCHC), 4.23 (2H, t, J=7.4 Hz, NCH.sub.2), 4.07 (2H, q, J=6.9 Hz, OCH.sub.2), 1.85 (2H, m, CH.sub.2), 1.30 (3H, t, J=6.9 Hz, CH.sub.3), 1.25 (6H, m, 3xCH.sub.2), 0.80 (3H, t, J=7.0 Hz, CH.sub.3)

(180) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 151.3 (C), 135.8 (NCHN), 131.9 (CH), 125.3 (CH), 123.6, 122.9 (C), 121.9 (CH), 121.3 (CH), 113.3 (CH), 64.8 (CH.sub.2), 50.4 (CH.sub.2), 30.9 (CH.sub.2), 29.9 (CH.sub.2), 25.6 (CH.sub.2), 22.2 (CH.sub.2), 14.2 (CH.sub.3), 13.8 (CH.sub.3)

(181) Elementary analysis (C.sub.19H.sub.25F.sub.6N.sub.3O.sub.5S.sub.2)

(182) calcd.: C, 41.23%, H, 4.55%, N, 7.59%, S, 11.59%.

(183) found: C, 41.35%, H, 4.48%, N, 7.77%, S, 10.56%.

1-(2-Ethoxyphenyl)-3-undecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(184) (C.sub.24H.sub.35F.sub.6N.sub.3O.sub.5S.sub.2, 623.672 g/mol)

(185) ##STR00024##
4.9 g (10.4 mmol) 1-(2-ethoxyphenyl)-3-undecylimidazoliumiodide and 3.58 g (12.5 mmol) lithium bis(trifluoromethylsulfonyl)amide are dissolved in 100 mL of a methanol-water mixture and 25 mL of dichloromethane are added. After stirring for 24 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator and the liquid product is obtained in 97% yield (6.29 g).

(186) Thermic stabilty: decompositin onset: 240 C., inflection point: 425 C.

(187) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 8.86 (1H, s, NCHN), 7.46 (2H, s, NCHC), 7.37 (2H, m, CH arom.), 7.01 (2H, m, CH arom.), 4.23 (2H, t, J=7.4 Hz, NCH.sub.2), 4.07 (2H, q, J=6.8 Hz, OCH.sub.2), 1.85 (2H, m, CH.sub.2), 1.30 (3H, t, J=6.9 Hz, CH.sub.3), 1.20 (16H, m, 8xCH.sub.2), 0.79 (3H, t, J=7.0 Hz, CH.sub.3)

(188) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 151.3 (C arom.), 135.8 (NCHN), 131.9 (CH), 125.3 (CH), 123.6 (CH), 122.9 (C arom.), 121.9 (CH), 121.3 (CH), 113.4 (CH), 50.4 (CH.sub.2), 3.18 (CH.sub.2), 30.0 (CH.sub.2), 29.5 (CH.sub.2), 29.4 (CH.sub.2), 29.2 (CH.sub.2), 29.2 (CH.sub.2), 29.1 (CH.sub.2), 28.8 (CH.sub.2), 25.9 (CH.sub.2), 22.6 (CH.sub.2), 14.2 (CH.sub.3), 14.0 (CH.sub.3)

(189) elementary analysis (C.sub.24H.sub.35F.sub.6N.sub.3O.sub.5S.sub.2)

(190) calcd: C, 46.22%, H, 5.66%, N, 6.74%, S, 10.28%.

(191) found: C, 46.26%, H, 5.50%, N, 6.90%, S, 10.24%.

1-(2-Ethoxyphenyl)-3-tetradecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(192) (C.sub.27H.sub.41F.sub.6N.sub.3O.sub.5S.sub.2, 665.752 g/mol)

(193) ##STR00025##
2.65 g (5.7 mmol) 1-(2-ethoxyphenyl)-3-tetradecylimidazoliumbromide and 1.96 g (6.8 mmol) lithium bis(trifluoromethylsulfonyl)amide are dissolved in 100 mL of a methanol-water mixture and 25 mL of dichloromethane are added. After stirring for 24 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product is obtained in 78% yield (2.97 g).

(194) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 8.83 (1H, s, NCHN), 7.45 (2H, m, NCHC), 7.37 (2H, m, CH arom.), 7.01 (2H, m, CH arom.), 4.23 (2H, t, J=7.6 Hz, NCH.sub.2), 4.07 (2H, q, J=6.9 Hz, OCH.sub.2), 1.85 (2H, m, CH.sub.2), 1.30 (3H, t, J=6.9 Hz, CH.sub.3), 1.20 (22H, m, 11xCH.sub.2), 0.79 (3H, t, J=6.8 Hz, CH.sub.3)

(195) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 151.3 (C arom.), 135.8 (NCHN), 131.9 (CH), 125.3 (CH), 123.6 (CH), 121.9 (CH), 121.3 (CH), 113.4 (CH), 64.8 (CH.sub.2), 50.4 (CH.sub.2), 31.8 (CH.sub.2), 30.0 (CH.sub.2), 29.6 (CH.sub.2), 29.5 (CH.sub.2), 29.4 (CH.sub.2), 29.3 (CH.sub.2), 28.9 (CH.sub.2), 25.9 (CH.sub.2), 22.6 (CH.sub.2), 14.2 (CH.sub.2), 14.0 (CH.sub.2),

(196) Elementary analysis (C.sub.27H.sub.41F.sub.6N.sub.3O.sub.5S.sub.2)

(197) calcd.: C, 48.71%, H, 6.21%, N, 6.31%, S, 9.63%.

(198) found: C, 48.70%, H, 6.63%, N, 6.62%, S, 8.75%.

1-(4-Bromophenyl)-3-butyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(199) (C.sub.15H.sub.16BrF.sub.6N.sub.3O.sub.4S.sub.2, 560.329 g/mol)

(200) ##STR00026##
4.42 g (0.011 mol) 1-(4-bromophenyl)-3-butylimidazoliumiodide and 3.74 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in a water-methanol mixture and 10 mL of dichloromethane are added. The reaction mixture is stirred for 24 hours at room temperature and the organic phase is separated subsequently. After removal of the solvent, the liquid product is obtained in 100% yield (6.012 g).

(201) Thermic stabilty: Decomposition onset: 324 C., inflection point: 450 C.

(202) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.83 (1H, s, NCHN), 8.33 (1H, s, NCHC), 8.05 (1H, s, NCHC), 7.90 (2H, d, J=8.6 Hz, CH arom.), 4.25 (2H, t, J=7.4, NCH.sub.2), 1.88 (2H, m, CH.sub.2), 1.34 (2H, m, CH.sub.2), 0.94 (3H, t, J=7.4 Hz, CH.sub.3)

(203) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 135.5 (NCHN), 134.1 (C arom.), 132.9 (2CH), 123.4 (2CH), 123.4 (CH), 122.3 (C arom.), 119.3 (CH), 49.3 (CH.sub.2), 31.1 (CH.sub.2), 18.9 (CH.sub.2), 13.2 (CH.sub.3)

(204) Elementary analysis (C.sub.15H.sub.16BrF.sub.6N.sub.3O.sub.4.sub.S.sub.2)

(205) calcd.: C, 32.15%, H, 2.88%, N, 7.50%, S, 11.45%.

(206) found: C, 32.3%, H, 2.55%, N, 7.78%, S, 11.27%.

1-(4-Bromophenyl)-3-hexyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(207) (C.sub.17H.sub.20BrF.sub.6N.sub.3O.sub.4S.sub.2, 588.383 g/mol)

(208) ##STR00027##
2.966 g (6.8 mmol) 1-(4-bromophenyl)-3-hexyl-1H-imidazoliumiodide and 2.33 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in a water-methanol mixture and 10 mL of dichloromethane are added. The reaction mixture is stirred for 24 hours at room temperature and the organic phase is separated subsequently. After removal of the solvent, the product (melting point 31 C.) is obtained in 100% yield.

(209) Thermic stabilty: Decomposition onset: 304 C., inflection point: 450 C.

(210) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.83 (1H, s, NCHN), 8.33 (1H, m, NCHC), 8.05 (1H, m, NCHC), 7.91 (2H, d, J=9 Hz, ArH), 7.77 (2H, d, J=9 Hz, ArH), 4.24 (2H, t, J=7 Hz, NCH.sub.2), 1.89 (2H, m, CH.sub.2), 1.32 (6H, m, 3xCH.sub.2), 0.88 (3H, t, J=6.5 Hz, CH.sub.3)

(211) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 135.5 (NCHN), 134.1 (C), 132.9 (CH), 123.9 (CH), 122.6 (C), 122.2 (CH), 121.1 (CH), 49.4 (NCH.sub.2), 30.6 (CH.sub.2), 29.0 (CH.sub.2), 25.2 (CH.sub.2), 21.8 (CH.sub.2), 13.8 (CH.sub.3),

(212) Elementary analysis (C.sub.17H.sub.20BrF.sub.6N.sub.3O.sub.4S.sub.2)

(213) calcd.: C, 34.70%, H, 3.43%, N, 7.14%, S, 10.90%.

(214) found: C, 34.77%, H, 3.35%, N, 7.41%, S, 10.15%.

1-(4-Bromophenyl)-3-undecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(215) (C.sub.22H.sub.30BrF.sub.6N.sub.3O.sub.4S.sub.2, 658.516 g/mol)

(216) ##STR00028##
4.38 g (9 mmol) 1-(4-bromophenyl)-3-undecyl-1H-imidazoliumiodide and 2.99 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in a water-methanol mixture and dichloromethane is added. The reaction mixture is stirred for 24 hours at room temperature and the organic phase is separated subsequently. After removal of the solvent, the product (melting point 35 C.) is obtained in 94% yield (5.54 g).

(217) Thermic stabilty: Decomposition onset: 243 C., inflection point: 460 C.

(218) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.83 (1H, s, NCHN), 8.33 (1H, m, NCHC), 8.05 (1H, m, NCHC), 7.91 (2H, d, J=8.7 Hz, CH arom.), 7.77 (2H, d, J=8.7 Hz, CH arom.), 4.24 (2H, t, J=7.2 Hz, NCH.sub.2), 1.89 (2H, m, CH.sub.2), 1.28 (16H, m, 8xCH.sub.2), 0.86 (3H, m, CH.sub.3)

(219) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 135.5 (NCHN), 134.1 (C), 132.9 (2CH), 123.9 (2CH), 123.3 (CH), 121.6 (CH), 49.5 (NCH.sub.2), CH.sub.2: 31.3, 29.1, 28.9, 28.8, 28.7, 28.4, 25.5, 22.1, 13.9 (CH.sub.3)

(220) Elementary analysis (C.sub.22H.sub.30BrF.sub.6N.sub.3O.sub.4S.sub.2)

(221) calcd.: C, 40.13%, H, 4.59%, N, 6.38%, S, 9.74%.

(222) found: C, 40.04%, H, 4.46%, N, 6.57%, S, 9.55%.

1-(4-Ethylphenyl)-3-methyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(223) (C.sub.15H.sub.17F.sub.6N.sub.3O.sub.4S.sub.2, 467.407 g/mol)

(224) ##STR00029##
4.0 g (0.013 mmol) 1-(4-ethylphenyl)-3-methylimidazoliumiodide and 3.73 g (0.013 mmol) lithium bis(trifluoromethylsulfonyl)amide are dissolved in 100 mL of water and 50 mL of dichloromethane are added. The reaction mixture is stirred for 2 hours at room temperature and the organic phase is separated subsequently. After removal of the solvent, the liquid product is obtained in 87% yield.

(225) Thermic stabilty: decomposition onset: 330 C., inflection point: 455 C.

(226) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.69 (1H, s, NCHN), 8.24 (1H, m, NCHC), 7.92 (1H, m, NCHC), 7.65 (2H, d, J=8.5 Hz, CH arom.), 7.49 (2H, d, J=8.5 Hz, CH arom.), 3.93 (3H, s, NCH.sub.3), 2.69 (2H, q, J=7.5 Hz, ArCH.sub.2), 1.21 (3H, t, J=7.5 Hz, CCH.sub.3)

(227) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 145.9 (C arom.), 135.8 (NCHN), 132.6 (C arom.), 129.4 (2CH), 124.4 (CH), 121.8 (2CH), 121.1 (CH), 36.1 (NCH.sub.3), 27.7 (ArCH.sub.2), 15.3 (CH.sub.3)

(228) Elementary analysis (C.sub.15H.sub.17F.sub.6N.sub.3O.sub.4S.sub.2)

(229) calcd.: C, 35.98%, H, 3.23%, N, 8.99%, S, 13.72%.

(230) found: C, 36.07%, H, 3.14%, N, 9.20%, S, 13.59%.

1-(4-Ethylphenyl)-3-butyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(231) (C.sub.17H.sub.21F.sub.6N.sub.3O.sub.4S.sub.2, 509.487 g/mol)

(232) ##STR00030##
3.15 g (8.84 mmol) 1-(4-ethylphenyl)-3-butyl-1H-limidazoliumiodide and 3.05 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 50 mL of water and 10 mL of dichloromethane are added. After stirring for 20 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product is obtained in 100% yield.

(233) Thermic stabilty: decomposition onset: 324 C., inflection point: 450 C.

(234) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.78 (1H, s, NCHN), 8.30 (1H, m, NCHC), 8.04 (1H, m, NCHC), 7.70 (2H, d, J=8.5 Hz, CH arom.), 7.51 (2H, d, J=8.5 Hz, CH arom.), 4.26 (2H, t, J=7.4 Hz, NCH.sub.2), 2.72 (2H, q, J=7.6 Hz, PhCH.sub.2), 1.90 (2H, m, CH.sub.2), 1.36 (2H, m, CH.sub.2), 1.23 (3H, t, J=7.6 Hz, CH.sub.3), 0.95 (3H, t, J=7.4 Hz, CH.sub.3)

(235) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 145.8 (C), 135.1 (NCHN), 132.6 (C), 129.3 (CH), 123.2 (CH), 121.8 (CH), 121.2 (CH), 49.1 (CH.sub.2), 31.1 (CH.sub.2), 28.7 (CH.sub.2), 18.8 (CH.sub.2), 15.4 (CH.sub.3), 13.2 (CH.sub.3)

(236) Elementary analysis (C.sub.17H.sub.21F.sub.6N.sub.3O.sub.4S.sub.2)

(237) calcd.: C, 40.08%, H, 4.14%, N, 8.25%, S, 12.59%.

(238) found: C, 40.43%, H, 4.37%, N, 8.42%, S, 12.37%.

1-(4-Ethylphenyl)-3-hexyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(239) (C.sub.19H.sub.25F.sub.6N.sub.3O.sub.4S.sub.2, 537.539 g/mol)

(240) ##STR00031##
6.38 g (0.017 mol) 1-(4-ethylphenyl)-3-hexyl-1H-imidazoliumiodide and 5.72 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 80 mL water and 25 mL of dichloromethane are added. After stirring for 20 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product is obtained in 86% yield (7.9 g).

(241) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 9.78 (1H, s, NCHN), 8.29 (1H, s, NCHC), 8.04 (1H, s, NCHC), 7.70 (2H, d, J=8.3 Hz, ArH), 7.50 (2H, d, J=8.3 Hz, ArH), 4.25 (2H, t, J=7.4 Hz, NCH.sub.2), 2.72 (2H, q, J=7.6 Hz, ArCH.sub.2), 1.91 (2H, m, CH.sub.2), 1.33 (6 H, m, 3xCH.sub.2), 1.23 (3H, t, J=7.6 Hz, CH.sub.3), 0.89 (3H, m, CH.sub.3)

(242) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 145.8 (C), 135.1 (NCHN), 132.6 (C), 129.3 (2CH), 121.8 (CH), 121.6 (2CH), 121.2 (CH), 117.4 (CF.sub.3), 49.4 (NCH.sub.2), 30.6 (CH.sub.2), 29.1 (CH.sub.2), 27.7 (CH.sub.2), 25.2 (CH.sub.2), 21.8 (CH.sub.2), 15.4 (CH.sub.3), 13.7 (CH.sub.3)

(243) Elementary analysis (C.sub.19H.sub.25F.sub.6N.sub.3O.sub.4S.sub.2)

(244) calcd.: C, 42.45%, H, 4.69%, N, 7.82%, S, 11.93%.

(245) found: C, 42.23%, H, 4.79%, N, 7.96%, S, 11.77%.

1-(4-Ethylphenyl)-3-undecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(246) (C.sub.24H.sub.35F.sub.6N.sub.3O.sub.4S.sub.2, 607.673 g/mol)

(247) ##STR00032##
2.27 g (0.005 mol) 1-(4-ethylphenyl)-3-undecyl-1H-limidazoliumiodide and 1.72 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 50 mL of water and 10 mL of dichloromethane are added. After stirring for 20 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product is obtained in 100% yield.

(248) Thermic stabilty: decomposition onset: 315 C., inflection point: 440 C.

(249) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 8.98 (1H, s, NCHN), 7.57 (1H, m, NCHC), 7.48 (1H, m, NCHC), 7.41 (2H, d, J=8.5 Hz, arom. CH), 7.31 (2H, d, J=8.5 Hz, arom. CH), 4.23 (2H, t, J=8.4 Hz, NCH.sub.2), 2.64 (2H, q, J=7.6 Hz, C.sub.arom-CH.sub.2), 1.86 (2H, m, CH.sub.2), 1.21 (19H, m, CH.sub.3, 8xCH.sub.2), 0.79 (3H, m, CH.sub.3)

(250) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 147.5 (C), 133.7 (NCHN), 131.9 (C), 129.9 (CH), 123.2 (CH), 121.9 (CH), 121.7 (CH), 50.6 (CH.sub.2), CH.sub.2 31.8, 30.1, 29.5, 29.4, 29.3, 29.2, 28.8, 28.4, 26.1, 22.6, 15.2 (CH.sub.3), 14.0 (CH.sub.3)

(251) Elementary analysis (C.sub.24H.sub.35F.sub.6N.sub.3O.sub.4S.sub.2.0.5H.sub.2O)

(252) calcd.: C, 46.74%, H, 5.88%, N, 6.81%, S, 10.38%.

(253) found: C, 46.73%, H, 5.95%, N, 7.27%, S, 9.91%.

1-(4-Ethylphenyl)-3-tetradecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(254) (C.sub.27H.sub.41F.sub.6N.sub.3O.sub.4.sub.S.sub.2, 649.753 g/mol)

(255) ##STR00033##
2.25 g (5 mmol) 1-(4-ethylphenyl)-3-tetradecyl-1H-imidazoliumbromide and 1.72 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 50 mL of water-methanol mixture and 10 mL of dichloromethane are added. After stirring for 20 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator.

(256) The liquid product is obtained in 100% yield (3.27 g).

(257) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 8.97 (1H, s, NCHN), 7.57 (1H, m, NCHC), 7.48 (1H, m, NCHC), 7.41 (2H, d, J=8.6 Hz, CH arom.), 7.31 (2H, d, J=8.6 Hz, CH arom.), 4.22 (2H, t, J=7.6 Hz, NCH.sub.2), 2.64 (2H, q, J=7.7 Hz, CH.sub.2), 1.86 (2H, m, CH.sub.2), 1.21 (22H, m, 11xCH.sub.2), 1.18 (3H, t, J=7.7 Hz, CH.sub.3), 0.78 (3H, t, J=6.8 Hz, CH.sub.3)

(258) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 147.3 (C), 133.7 (NCHN), 132.0 (C), 129.9 (CH), 123.2 (CH), 121.9 (CH), 121.7 (CH), 50.6 (CH.sub.2), 31.9 (CH.sub.2), 30.1 (CH.sub.2), 29.6 (CH.sub.2), 29.5 (CH.sub.2), 29.4 (CH.sub.2), 29.3 (CH.sub.2), 28.9 (CH.sub.2), 28.4 (CH.sub.2), 26.1 (CH.sub.2), 22.6 (CH.sub.2), 15.2 (CH.sub.3), 14.0 (CH.sub.3)

(259) Elementary analysis (C.sub.27H.sub.41F.sub.6N.sub.3O.sub.4S.sub.2)

(260) calcd.: C, 49.91%, H, 6.36%, N, 6.47%, S, 9.87%.

(261) found: C, 50.03%, H, 6.59%, N, 6.83%, S, 9.49%.

1-(2-Ethylphenyl)-3-methyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(262) (C.sub.14H.sub.15F.sub.6N.sub.3O.sub.4S.sub.2, 467.407 g/mol)

(263) ##STR00034##
17.5 g (0.056 mmol) 1-(2-ethylphenyl)-3-methylimidazoliumiodide and 16 g (0.056 mmol) lithium bis(trifluoromethylsulfonyl)amide are dissolved in 250 mL of water and 25 mL of dichloromethane are added. The reaction mixture is stirred for 2 hours at room temperature and the organic phase is separated subsequently. After removal of the solvent, an oily liquid is obtained in 97% yield.

(264) Thermic stabilty: decomposition onset: 255 C., inflection point: 460 C.

(265) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.45 (1H, s, NCCH), 8.04 (1H, s, NCCH), 7.95 (1H, s, NCCH), 7.6 (2 H, m, CH arom.), 7.5 (3H, m, CH arom.), 2.5 (2H, q, CCH.sub.2), 1.09 (3H, t, CH.sub.3)

(266) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 139.4 (C arom.), 137.8 (NCHN), 133.7 (C arom.), 130.9 (CH), 129.8 (CH), 127.3 (CH), 126.9 (CH), 124.0 (CH), 123.9 (CH), 36.1 (NCH.sub.3), 23.0 (ArCH.sub.2), 14.4 (CH.sub.3)

(267) Elementary analysis (C.sub.14H.sub.15F.sub.6N.sub.3O.sub.4S.sub.2)

(268) calcd.: C, 35.98%, H, 3.23%, N, 8.99%, S, 13.72%.

(269) found: C, 35.72%, H, 3.26%, N, 9.05%, S, 13.69%.

1-(2-Ethylphenyl)-3-butyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(270) (C.sub.17H.sub.21F.sub.6N.sub.3O.sub.4S.sub.2, 509.487 g/mol)

(271) ##STR00035##
0.68 g (1.91 mmol) 1-(2-ethylphenyl)-3-butyl-1H-imidazoliumiodide and 0.55 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 50 mL of water and 10 mL of dichloromethane are added. After stirring for 24 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product (melting point 16 C.) is obtained in 100% yield.

(272) Thermic stabilty: decomposition onset: 295 C., inflection point 440 C.

(273) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.57 (1H, s, NCHN), 8.09 (1H, s, NCHC), 8.07 (1H, s, NCHC), 7.56 (4H, m, CH arom.), 4.29 (2H, t, J=7.4 Hz, NCH.sub.2), 2.50 (2H, q, J=7.6 Hz, PhCH.sub.2), 1.91 (2H, m, CH.sub.2), 1.34 (2H, m, CH.sub.2), 1.10 (3H, t, J=7.6 Hz, CH.sub.3), 0.96 (3H, t, J=7.4 (3H, t, J=7.4 Hz, CH.sub.3)

(274) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 139.3 (C), 137.1 (NCHN), 133.7 (C), 130.9 (CH), 129.8 (CH), 127.3 (CH), 126.9 (CH), 124.3 (CH), 122.8 (CH), 121.6 (CF.sub.3), 117.4 (CF.sub.3), 49.0 (CH.sub.2), 31.1 (CH.sub.2), 23.1 (CH.sub.2), 18.8 (CH.sub.2), 14.3 (CH.sub.3), 13.2 (CH.sub.3)

(275) Elementary analysis (C.sub.17H.sub.21F.sub.6N.sub.3O.sub.4S.sub.2)

(276) calcd.: C, 40.08%, H, 4.15%, N, 8.25%, S, 12.59%.

(277) found: C, 40.34%, H, 4.36%, N, 8.48%, S, 12.26%.

1-(2-Ethylphenyl)-3-hexyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(278) (C.sub.19H.sub.25F.sub.6N.sub.3O.sub.4S.sub.2, 537.539 g/mol)

(279) ##STR00036##
6.38 g (0.017 mol) 1-(2-ethylphenyl)-3-hexyl-1H-imidazoliumiodide and 5.72 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 100 mL of water and 25 mL of dichloromethane are added after stirring for one hour at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product is obtained in 86% yield (7.9 g).

(280) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.57 (1H, s, NCHN), 8.09 (1H, m, NCHC), 8.07 (1H, m, NCHC), 7.56 (4H, m, CH arom.), 4.29 (2H, d, J=7.2 Hz, NCH.sub.2), 2.50 (2H, q, J=7.6 Hz, CH.sub.2), 1.92 (2H, m, CH.sub.2), 1.32 (6H, m, 3xCH.sub.2), 1.90 (3H, t, J=7.6 Hz, CH.sub.3), 0.89 (3H, m, CH.sub.3)

(281) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 139.3 (CH), 137.1 (NCHN), 133.7 (C), 131.0 (CH), 129.8 (CH), 127.3 (CH), 126.9 (CH), 124.3 (CH), 122.8 (CH), 121.6 (CF.sub.3), 117.4 (CF.sub.3), 49.3 (NCH.sub.2), 30.5 (CH.sub.2), 29.0 (CH.sub.2), 25.1 (CH.sub.2), 23.1 (CH.sub.2), 21.9 (CH.sub.2), 14.3 (CH.sub.3), 13.7 (CH.sub.3)

(282) Elementary analysis (C.sub.19H.sub.25F.sub.6N.sub.3O.sub.4S.sub.2)

(283) calcd.: C, 42.45%, H, 4.69%, N, 7.82%, S, 11.93%.

(284) found: C, 42.67%, H, 4.88%, N, 7.96%, S, 11.84%.

1-(2-Ethylphenyl)-3-undecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(285) (C.sub.24H.sub.35F.sub.6N.sub.3O.sub.4S.sub.2, 607.673 g/mol)

(286) ##STR00037##
1.095 g (2.41 mmol) 1-(2-ethylphenyl)-3-undecyl-1H-imidazoliumiodide and 0.83 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 60 mL of water and 10 mL of dichloromethane are added. After stirring for 20 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator. The liquid product (melting point 22 C.) is obtained in 100% yield.

(287) Thermic stabilty: decomposition onset: 299 C., inflection point: 430 C.

(288) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 8.73 ppm (1H, s, NCHN), 7.53 ppm (1H, s, NCHC), 7.47 ppm (1H, m), 7.36 ppm (1H, m), 7.26 ppm (3H, m), 4.25 ppm (2H, t, J=7.6 Hz, NCH.sub.2), 2.39 ppm (2H, q, J=7.6 Hz, ArCH.sub.2), 1.86 ppm (2H, m, CH.sub.2), 1.22 ppm (16H, m, 8xCH.sub.2), 1.07 ppm (3H, t, J=7.6 Hz, CH.sub.3), 0.80 ppm (3H, m, CH.sub.3)

(289) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 139.3 (C), 135.9 (NCHN), 132.9 (C), 131.5 (CH), 129.9 (CH), 127.6 (CH), 126.5 (CH), 124.2 (CH), 122.8 (CH), 50.5 (CH.sub.2), 31.8 (CH.sub.2), 30.0 (CH.sub.2), 29.5 (CH.sub.2), 29.4 (CH.sub.2), 29.3 (CH.sub.2), 29.2 (CH.sub.2), 28.8 (CH.sub.2), 26.0 (CH.sub.2), 23.5 (CH.sub.2), 22.6 (CH.sub.2), 14.4 (CH.sub.3), 14.0 (CH.sub.3)

(290) Elementary analysis (C.sub.24H.sub.35F.sub.6N.sub.3O.sub.4S.sub.2)

(291) calcd.: C, 47.44%, H, 5.81%, N, 7.02%, S, 10,55%.

(292) found: C, 47.45%, H, 5.62%, N, 7.06%, S, 10.26%.

1-(2-Ethylphenyl)-3-tetradecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(293) (C.sub.27H.sub.41F.sub.6N.sub.3O.sub.4S.sub.2, 649.753 g/mol)

(294) ##STR00038##
2.25 g (5 mmol) 1-(2-ethylphenyl)-3-tetradecyl-1H-imidazoliumbromide and 1.72 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in 50 mL of water-methanol mixture and 10 mL of dichloromethane are added. After stirring for 20 hours at room temperature, the organic phase is separated and concentrated on the rotary evaporator.

(295) The liquid product is obtained in 100% yield (3.27 g).

(296) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 8.72 (1H, s, NCHN), 7.52 (1H, m, NCHC), 7.46 (1H, m, CH arom.), 7.29 (4H, m, CH arom., NCHC), 4.24 (2H, t, J=7.6 Hz, CH.sub.2), 2.38 (2H, q, J=7.6 Hz, CH.sub.2), 1.86 (2H, m, CH.sub.2), 1.20 (22H, m, 11xCH.sub.2), 1.07 (3H, t, J=7.6 Hz, CH.sub.3), 0.80 (3H, t, J=6.9 Hz, CH.sub.3)

(297) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 139.2 (C), 135.9 (NCHN), 132.9 (C), 131.5 (CH), 130.0 (CH), 127.6 (CH), 126.5 (CH), 124.2 (CH), 122.7 (CH), 50.5 (CH.sub.2), 31.9 (CH.sub.2), 30.0 (CH.sub.2), 29.6 (CH.sub.2), 29.5 (CH.sub.2), 29.4 (CH.sub.2), 29.3 (CH.sub.2), 28.8 (CH.sub.2), 26.0 (CH.sub.2), 23.6 (CH.sub.2), 22.6 (CH.sub.2), 14.4 (CH.sub.3), 13.1 (CH.sub.3)

(298) Elementary analysis (C.sub.27H.sub.41F.sub.6N.sub.3O.sub.4S.sub.2)

(299) calcd.: C, 49.91%, H, 6.36%, N, 6.47%, S, 9.87%.

(300) found: C, 49.67%, H, 6.18%, N, 6.64%, S, 9.51%.

1-(2-Bromophenyl)-3-methyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(301) (C.sub.12H.sub.10BrF.sub.6N.sub.3O.sub.4S.sub.2, 518.253 g/mol)

(302) ##STR00039##
1.534 g (4.23 mmol) 1-(2-bromophenyl)-3-methyl-1H-imidazoliumiodide and 1.45 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in water and dichloromethane is added. The reaction mixture is stirred for 24 hours at room temperature and the organic phase is separated subsequently. After removal of the solvent, the product (melting point 15 C.) is obtained in 99% yield.

(303) Thermic stabilty: Decomposition onset: 337 C., inflection point: 450 C.

(304) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 8.72 (1H, s, NCHN), 7.70 (1H, m, NCHC), 7.49 (2H, m), 7.43 (2H, m), 7.35 (1H, m), 3.98 (3H, s, NCH.sub.3)

(305) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 136.7 (NCHN), 134.2 (CH), 133.3 (CH), 132.8 (CH), 129.4 (CH), 128.2 (CH), 123.9 (CH), 118.8 (C), 36.8 (CH.sub.3)

(306) Elementary analysis (C.sub.12H.sub.10BrF.sub.6N.sub.3O.sub.4S.sub.2)

(307) calcd.: C, 27.81%, H, 1.94%, N, 8.11%, S, 12.37%.

(308) found: C, 28.03%, H, 1.70%, N, 8.15%, S, 12.31%.

1-(2-Bromophenyl)-3-undecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(309) (C.sub.22H.sub.30BrF.sub.6N.sub.3O.sub.4S.sub.2, 658.516 g/mol)

(310) ##STR00040##
4.91 g (9.7) mmol) 1-(2-bromophenyl)-3-undecyl-1H-imidazoliumiodide and 3.07 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in a water-methanol mixture and dichloromethane is added. The reaction mixture is stirred for 24 hours at room temperature and the organic phase is separated subsequently. After removal of the solvent, the product is obtained in 41% yield (2.65 g).

(311) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 8.79 (1H, s, NCHN), 7.71 (1H, dd, J.sub.1=7.sub.1, Hz, J.sub.2=1.5 Hz, NCHC), 7.52 (2H, m, CH arom.), 7.44 (1H, dd, J.sub.1=14.7 Hz, J.sub.2=1.51 Hz, NCHC), 7.44 (1H, m, CH arom.), 7.38 (1H, m, CH arom.), 4.26 (2H, t, J=7.6 Hz, NCH.sub.2), 1.88 (2H, m, CH.sub.2), 1.22 (16H, m, 8xCH.sub.3), 0.80 (3H, t, J=6.8 Hz, CH.sub.3)

(312) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 144.3 (CBr), 136.3 (NCHN), 134.2 (CH), 133.4 (CN), 132.8 (CH), 129.5 (CH), 128.3 (CH), 124.2 (CH), 122.6 (CH), 50.8 (NCH.sub.2), (CH.sub.2: 31.9, 29.9, 29.5, 29.4, 29.3, 28.3, 28.8, 26.0, 22.7), 14.1 (CH.sub.3)

1-(2-Bromophenyl)-3-tetradecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(313) (C.sub.25H.sub.36BrF.sub.6N.sub.3O.sub.4S.sub.2, 700.595 g/mol)

(314) ##STR00041##
8.3 g (0.015 mol) 1-(4-bromophenyl)-3-tetradecyl-1H-imidazoliumbromide and 4.79 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in water-methanol mixture and dichloromethane is added. The reaction mixture is stirred for 24 hours at room temperature and the organic phase is separated subsequently. After removal of the solvent, the product is obtained in 99% yield (10.37 g).

(315) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 8.79 (1H, s, NCHN), 7.71 (1H, dd, J.sub.1=9.3 Hz, J.sub.2=1.5 Hz, NCHC), 7.51 (2H, m, CH arom.), 7.44 (1H, m, CH arom.), 7.44 (1H, dd, J.sub.1=17.2 Hz, J.sub.2=1.5 Hz, NCHC), 4.26 (2H, t, J=7.4 Hz, NCH.sub.2), 1.87 (2H, m, CH.sub.2), 1.24 (22H, m, 11xCH.sub.2), 0.80 (3H, t, J=6.9 Hz, CH.sub.3),

(316) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 144.3 (CBr), 136.2 (NCHN), 134.1 (CH), 133.4 (CN), 132.8 (CH), 129.4 (CH), 128.3 (CH), 124.1 (CH), 122.6 (CH), 50.7 (NCH.sub.2), (CH.sub.2: 31.9, 29.9, 29.6, 29.5, 29.4, 29.3, 28.8, 23.9, 22.6), 14.1 (CH.sub.3)

1-(4-Chlorophenyl)-3-butyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(317) (C.sub.15H.sub.16ClF.sub.6N.sub.3O.sub.4S.sub.2, 515.879, g/mol)

(318) ##STR00042##
2.96 g (8.2 mmol) 1-(4-chlorophenyl)-3-butyl-1H-imidazoliumiodide and 2.58 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in a water-methanol mixture. The reaction mixture is stirred for 2 days at room temperature and subsequently dichloromethane is added for a better phase separation. The organic phase is separated. After removal of the solvent, an oily liquid is obtained (96% yield).

(319) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 8.99 (1H, s, NCHN), 7.61 (1H, s, NCHC), 7.47 (5H, m, NCHC, CH arom.), 4.21 (2H, t, J=7.6 Hz, NCH.sub.2), 1.84 (2H, m, CH.sub.2), 1.32 (2H, m, CH.sub.2), 0.89 (3H, t, J=7.4 Hz, CH.sub.3)

(320) .sup.13C-NMR (75.5 MHz, CDCl.sub.3): 136.6 (CCl), 133.9 (NCHN), 132.7 (CN), 123.5 (CH), 121.8 (CH), 50.4 (NCH.sub.2), 31.8 (CH.sub.2), 19.3 (CH.sub.2), 13.1 (CH.sub.3)

(321) Elementary analysis (C.sub.15H.sub.16ClF.sub.6N.sub.3O.sub.4S.sub.2)

(322) calcd.: C, 34.92%, H, 3.13%, N, 8.15%, S, 12.43%.

(323) found: C, 34.85%, H, 3.20%, N, 8.36%, S, 12.63%.

1-(4-Chlorophenyl)-3-hexyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(324) (C.sub.17H.sub.20ClF.sub.6N.sub.3O.sub.4S.sub.2, 543.932 g/mol)

(325) ##STR00043##
2.80 g (7.2 mmol) 1-(4-chlorophenyl)-3-hexyl-1H-imidazoliumiodide and 2.26 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in a water-methanol mixture. The reaction mixture is stirred for 2 days at room temperature and subsequently dichloromethane is added for a better phase separation. The organic phase is separated. After removal of the solvent, an oily liquid is obtained (95% yield).

(326) .sup.1H-NMR (300 MHz, d.sup.6-DMSO, ppm): 9.83 (1H, s, NCHN), 8.33 (1H, m, NCHC), 8.05 (1H, m, NCHC), 7.84 (2H, d, J=7 Hz, ArH), 7.77 (2H, d, J=7 Hz, ArH), 4.25 (2H, t, J=7.1 Hz, NCH.sub.2), 1.89 (2H, m, CH.sub.2, 1.33 (3H, m, 3xCH.sub.2), 0.89 (3H, t, J=6.6 Hz, CH.sub.3)

(327) .sup.13C-NMR (75.5 MHz, d.sup.6-DMSO, ppm): 134.6 (NCHN), 130.1 (2CH), 123.7 (2CH), 123.3 (CH), 121.9 (C), 121.6 (CH), 49.4 (NCH.sub.2), 30.6 (CH.sub.2), 29.1 (CH.sub.2), 25.2 (CH.sub.2), 21.8 (CH.sub.2), 13.8 (CH.sub.3)

(328) Elementary analysis (C.sub.17H.sub.20ClF.sub.6N.sub.3O.sub.4S.sub.2)

(329) calcd.: C, 37.54%, H, 3.71%, N, 7.73%, S, 11.79%.

(330) found: C, 37.19%, H, 3.13%, N, 7.69%, S, 12.43%.

1-(4-Chlorophenyl)-3-undecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylamide

(331) (C.sub.22H.sub.30ClF.sub.6N.sub.3O.sub.4S.sub.2, 614.065 g/mol)

(332) ##STR00044##
1.04 g (2.3 mmol) 1-(4-chlorophenyl)-3-undecyl-1H-imidazoliumiodide and 0.71 g lithium bis(trifluoromethylsulfonyl)amide are dissolved in a water-methanol mixture. The reaction mixture is stirred for 2 days at room temperature and subsequently dichloromethane is added for a better phase separation. The organic phase is separated. After removal of the solvent, an oily liquid is obtained (98% yield).

(333) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 9.03 (1H, s, NCHN), 7.61 (1H, m, NCHC), 7.48 (5H, m, NCHC+CH arom.), 4.22 (2H, t, J=7.7 Hz, NCH.sub.2), 1.86 (2H, m, CH.sub.2), 1.22 (16H, m, 8xCH.sub.2), 0.88 (3H, t, J=6.8 Hz, CH.sub.3)

(334) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 136.8 (CCl), 134.0 (NCHN), 132.7 (CN), 130.8 (CH), 123.5 (CH), 123.4 (CH), 121.9 (CH), 50.8 (NCH.sub.2), (CH.sub.2: 31.8, 30.0, 29.5, 29.4, 29.3, 29.2, 28.8, 26.1, 22.6), 14.0 (CH.sub.3)

(335) Elementary analysis (C.sub.22H.sub.30ClF.sub.6N.sub.3O.sub.4S.sub.2)

(336) calcd.: C, 43.03%, H, 4.92%, N, 6.84%, S, 10.44%.

(337) found: C, 43.26%, H, 5.11%, N, 7.07%, S, 10.01%.

1-(2-Methoxy-4-nitrophenyl)-3-undecyl-1H-imidazoliumbis(trifluoromethyl)sulfonylimide

(338) (C.sub.23H.sub.33F.sub.6N.sub.3O.sub.3S.sub.2, 654.643 g/mol)

(339) ##STR00045##
2.61 g (5.21 mmol) 1-(2-methoxy-4-nitrophenyl)-3-undecyl-1H-imidazoliumiodide and 1.79 g (6.25 mmol) lithium bis(trifluoromethylsulfonyl)amide are dissolved in 60 mL of a methanol-water mixture and 10 mL of Byker methane are added. After stirring for 20 hours at room temperature the organic phase is separated and concentrated on the rotary evaporator. The liquid product is obtained in 93% yield (3.15 g).

(340) .sup.1H-NMR (300 MHz, CDCl.sub.3, ppm): 9.09 (1H, s, NCHN), 7.88 (2H, s, NCHC), 7.67 (1H, d, J=8.12 Hz, CH arom.), 7.61 (1H, m, CH arom.), 7.48 (1H, m, CH arom.), 4.25 (2H, t, J=7.6 Hz, NCH.sub.2), 3.96 (3H, s, OCH.sub.3), 1.87 (2H, m, CH.sub.2), 1.20 (16H, m, 8xCH.sub.2), 0.79 (3H, t, J=7.0 Hz, CH.sub.3)

(341) .sup.13C-NMR (75.5 MHz, CDCl.sub.3, ppm): 152.7 (C), 149.4 (C), 136.3 (CH), 127.8 (C), 126.6 (CH), 123.5 (CH), 122.4 (CH), 108.0 (CH), 57.1 (OCH.sub.3), 50.7 (NCH.sub.2), 31.8 (CH.sub.2), 29.9 (CH.sub.2), 29.4 (CH.sub.2), 29.3 (CH.sub.2), 29.2 (CH.sub.2), 28.8 (CH.sub.2), 26.0 (CH.sub.2), 22.6 (CH.sub.2), 14.0 (CH.sub.3)

(342) Elementary analysis (C.sub.23H.sub.33F.sub.6N.sub.3O.sub.5S.sub.2.0.485H.sub.2O)

(343) calcd.: C, 41.64%, H, 5.01%, N, 8.45%, S, 9.65%.

(344) found: C, 41.16%, H, 4.14%, N, 9.15%, S, 9.42%.