IP Library › Granted Patent US 8,980,643
Granted Patent B2
US 8,980,643 · App. 12/867,139 · Granted Mar 17, 2015

Dicationic liquid salts and methods of use thereof

Inventor: Daniel W. Armstrong (Arlington, TX)
Assignee: Sigma-Aldrich Co., LLC
H01J49/165
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Quick Facts
Patent No.
US 8,980,643
App. No.
12/867,139
Granted
Mar 17, 2015
Kind
B2
Abstract

Dicationic liquid salts and methods of using such dicationic liquid salts in techniques such as ESI-MS are provided.

Claims (32)

1. A method of detecting at least one charged analyte in a sample by ESI-MS, the method comprising:

adding to the sample at least one dicationic liquid salt comprising a dicationic species corresponding in structure to Formula I:

and at least one counter-anion, wherein the at least one counter-anion comprises OH − , and

detecting a complex formed between the at least one charged analyte and the dicationic species of the at least one dicationic liquid salt using ESI-MS,

wherein:

X is phosphonium substituted with one or more substituents independently selected from the group consisting of methyl, ethyl, propyl and butyl; and

B is C 1 -C 12 -alkylene or —CH 2 -phenyl-CH 2 —, wherein C 1 -C 12 -alkylene optionally contains in the chain one or more oxygen atom.

2. The method of claim 1 , wherein the dicationic species is selected from the group consisting of:

3. The method of claim 1 , wherein the ESI-MS is carried out in the positive ion mode.

4. The method of claim 1 , wherein the charged analyte comprises an anion having a charge of −1, wherein the charged analyte pairs with the dicationic species to form a complex having a net positive charge.

5. The method of claim 1 , wherein the dicationic liquid salt is added to a carrier flow solvent.

6. The method of claim 5 , wherein a dicationic liquid salt solution of about 1 μM to about 200 μM is added to the carrier flow solvent.

7. The method of claim 5 , wherein the carrier flow solvent is a water-miscible organic solvent or a mixture of water and the water-miscible organic solvent.

8. The method of claim 7 , wherein the water-miscible organic solvent is selected from the group consisting of methanol, ethanol, propanol, acetonitrile, tetrahydrofuran and dioxane.

9. The method of claim 1 , further comprising coupling ESI-MS with a separation technique.

10. The method of claim 9 , wherein the separation technique is selected from the group consisting of liquid chromatography, HPLC, ion chromatography, ion-exchange chromatography, SPE, SPME, TS-SPME and SPME/MALDI.

11. The method of claim 9 , wherein the dicationic liquid salt is added to the carrier flow solvent following the separation technique.

12. A method of detecting at least one charged analyte in a sample by ESI-MS, the method comprising:

adding to the sample at least one dicationic liquid salt comprising a dicationic species selected from the group consisting of:

and at least one counter-anion; and

detecting a complex formed between the at least one charged analyte and the dicationic species of the at least one dicationic liquid salt using ESI-MS.

13. The method of claim 12 , wherein the at least one counter-anion is F − .

14. The method of claim 12 , wherein the at least one counter-anion is OH − .

15. The method of claim 12 , wherein the ESI-MS is carried out in the positive ion mode.

16. The method of claim 12 , wherein the charged analyte comprises an anion having a charge of −1, and wherein the charged analyte pairs with the dicationic species to form a complex having a net positive charge.

17. The method of claim 12 , wherein the dicationic liquid salt is added to a carrier flow solvent.

18. The method of claim 17 , wherein a dicationic liquid salt solution of about 1 μM to about 200 μM is added to the carrier flow solvent.

19. The method of claim 17 , wherein the carrier flow solvent is a water-miscible organic solvent or a mixture of water and the water-miscible organic solvent.

20. The method of claim 19 , wherein the water-miscible organic solvent is selected from the group consisting of methanol, ethanol, propanol, acetonitrile, tetrahydrofuran and dioxane.

21. The method of claim 12 , further comprising coupling ESI-MS with a separation technique.

22. The method of claim 21 , wherein the separation technique is selected from the group consisting of liquid chromatography, HPLC, ion chromatography, ion-exchange chromatography, SPE, SPME, TS-SPME and SPME/MALDI.

23. The method of claim 21 , wherein the dicationic liquid salt is added to the carrier flow solvent following the separation technique.

Assignments (3)
MERGER Recorded Jul 6, 2011
From: SIGMA-ALDRICH CO.
To: SIGMA-ALDRICH CO. NEWCO INC.
Reel/Frame 026551/0161 →
CHANGE OF NAME Recorded Jul 6, 2011
From: SIGMA-ALDRICH CO. NEWCO INC.
To: SIGMA-ALDRICH CO. LLC
Reel/Frame 026552/0245 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2010
From: ARMSTRONG, DANIEL W.
To: SIGMA-ALDRICH CO.
Reel/Frame 024968/0678 →
Continuity (2)
Provisional Application 61029075 · Feb 15, 2008
Related Publication 20110017908A1 · Jan 27, 2011