1 Ethyl 35 dimethyl 2 pentylpyridinium bistrifluoromethane sulfonylimide 11

1 ethyl 35 dimethyl 2 pentylpyridinium

This preview shows page 7 - 9 out of 9 pages.

1-Ethyl-3,5-dimethyl-2-pentylpyridinium bis(trifluoromethane- sulfonyl)imide (11). Yield 89%. 1 H NMR (CDCl 3 ): d 8.39 (1H, s, 6-H), 7.97 (1H, s, 4-H), 4.58 (2H, q, J = 7.3 Hz, NC H 2 ), 2.98 (2H, dd, J 1 = 7.2 Hz, J 2 = 9.5 Hz, 1 ¢ -Pen), 2.53 (3H, s, Ar- CH 3 ), 2.49 (3H, s, Ar-CH 3 ), 1.64 (5H, m, NCH 2 C H 3 , 2 ¢ -Pen), 2774 | Green Chem. , 2011, 13 , 2768–2776 This journal is © The Royal Society of Chemistry 2011 Published on 18 August 2011. Downloaded by Memorial University of Newfoundland on 12/22/2018 10:10:24 PM. View Article Online
Image of page 7

Subscribe to view the full document.

1.51–1.35 (4H, m, 2 ¢ ,3 ¢ -Pen), 0.95 (3H, t, J = 7.2 Hz, 5 ¢ -Pen). 13 C NMR (CDCl 3 ): d 153.8, 147.5, 142.3, 138.0, 136.9, 119.81 (q, J C-F = 321.5 Hz), 53.7, 31.8, 29.3, 27.5, 22.1, 19.1, 17.7, 16.7, 13.8. 19 F RMN (CDCl 3 ): d - 78.94. Electrospray MS (micrOTOF Focus) m / z (%) 692.29877 ([(C 14 H 24 N) 2 (C 2 F 6 NO 4 S 2 )] + requires 692.29849, 2), 207 [(C 14 H 24 N + 1] + (19), 206.19070 ([(C 14 H 24 N] + requires 206.19033, 100). 1-Butyl-3,5-dimethyl-2-pentylpyridinium bis(trifluoromethane- sulfonyl)imide (12). Yield 95%. 1 H NMR (CDCl 3 ): d 8.38 (1H, s, 6-H), 7.97 (1H, s, 4-H), 4.48 (2H, dd, J 1 = 6.2 Hz, J 2 = 10.0 Hz, NC H 2 ), 2.96 (2H, dd, J 1 = 5.8 Hz, J 2 = 10.9 Hz, 1 ¢ -Pen), 2.53 (3H, s, Ar-CH 3 ), 2.49 (3H, s, Ar-CH 3 ), 1.92 (2H, tt, J 1 = 6.3 Hz, J 2 = 9.3 Hz, NCH 2 C H 2 ), 1.64 (2H, m, 2 ¢ -Pen), 1.50 (4H, m, N(CH 2 ) 2 C H 2 , 3 ¢ -Pen), 1.41 (2H, m, 4 ¢ -Pen), 1.02 (3H, t, J = 7.3 Hz, N(CH 2 ) 3 C H 3 ), 0.95 (3H, t, J = 7.2 Hz, 5 ¢ -Pen). 13 C NMR (CDCl 3 ): d 153.7, 147.4, 142.7, 137.9, 136.7, 119.81 (q, J C-F = 321.4 Hz), 58.2, 33.6, 31.8, 29.3, 27.4, 22.1, 19.7, 19.2, 17.7, 13.8, 13.4. 19 F RMN (CDCl 3 ): d - 78.92. Electrospray MS (micrOTOF Focus) m / z (%) 749 [(C 16 H 28 N) 2 (C 2 F 6 NO 4 S 2 ) + 1] + (2), 748.35789 ([(C 16 H 28 N) 2 (C 2 F 6 NO 4 S 2 )] + requires 748.36209, 5), 236 [(C 16 H 28 N) + 2] + (2), 235 [(C 16 H 28 N) + 1] + (32), 234.22145 ([(C 16 H 28 N)] + requires 234.22163, 100). 1-Hexyl-3,5-dimethyl-2-pentylpyridinium bis(trifluorometha- nesulfonyl)imide (13). Yield 93%. 1 H NMR (CDCl 3 ): d 8.41 (1H, s, 6-H), 7.96 (1H, s, 4-H), 4.49 (2H, dd, J 1 = 5.9 Hz, J 2 = 10.4 Hz, NC H 2 ), 2.96 (2H, dd, J 1 = 5.8 Hz, J 2 = 11.0 Hz, 1 ¢ -Pen), 2.54 (3H, s, Ar-CH 3 ), 2.50 (3H, s, Ar-CH 3 ), 1.93 (2H, m, NCH 2 C H 2 ), 1.65 (2H, m, 2 ¢ -Pen), 1.55–1.32 (10H, m, N(CH 2 ) 2 C H 2 C H 2 C H 2 , 3 ¢ ,4 ¢ -Pen), 0.97 (3H, t, J = 7.2 Hz, 5 ¢ -Pen), 0.92 (3H, t, J = 6.9 Hz, N(CH 2 ) 5 C H 3 ). 13 C NMR (CDCl 3 ): d 153.7, 147.5, 142.6, 137.9, 136.6, 119.81 (q, J C-F = 321.6 Hz), 58.4, 31.8, 31.7, 31.0, 29.3, 27.4, 26.0, 22.3, 22.1, 19.1, 17.7, 13.8, 13.7. 19 F RMN (CDCl 3 ): d - 78.87. Electrospray MS (micrOTOF Focus) m / z (%) 805 [(C 18 H 32 N) 2 (C 2 F 6 NO 4 S 2 ) + 1] + (2), 804.41966 ([(C 18 H 32 N) 2 (C 2 F 6 NO 4 S 2 )] + requires 804.42369, 4), 264 [(C 18 H 32 N) + 2] + (2), 263 [(C 18 H 32 N) + 1] + (32), 262 [(C 18 H 32 N)] + (100). Liquid–liquid equilibrium The experimental LLE for the two studied systems were carried out at T = 298.15 K and atmospheric pressure. For the exper- imental determination of tie-lines, immiscible mixtures of the three components (or only two components, in the case of binary tie-lines for the pair heptane + ionic liquid and thiophene + ionic liquid) were prepared. Heptane (Fluka, 99.5%) and thiophene (Sigma–Aldrich, ACS reagent, > 99%), were used as received, without further purification. The mixtures were placed into 10 mL round bottomed flasks together with a magnetic stirring bar under argon atmosphere. Flasks were sealed to avoid losses by evaporation or water absorption from the atmosphere. The temperature within the flask was kept at a constant 25.0 C by means of an IKA RCT Basic thermostatic water bath. The mixtures were first magnetically stirred for 4 h, and then allowed to settle down overnight to achieve phase separation. Samples of both layers were withdrawn using syringes connected to long stainless steel needles, without disturbance of the interface.
Image of page 8
Image of page 9
  • Winter '14

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern

Ask Expert Tutors You can ask You can ask ( soon) You can ask (will expire )
Answers in as fast as 15 minutes