Epoxy chemistry derived materials as mixed mode chromatography media, method for their synthesis and use

Patent metadata

Field	Value
Publication number	US-9329158-B2
Application number	US-201313842391-A
Country	US
Kind code	B2
Filing date	Mar 15, 2013
Priority date	Mar 15, 2013
Publication date	May 3, 2016
Grant date	May 3, 2016

Abstract

This invention provides mixed-mode stationary phase compositions, devices and systems comprising the stationary phases as well as methods of producing these compositions using epoxide ring-opening reactions. Also provided are methods of using the stationary phases of the invention in separations.

First claim

What is claimed is:

1. A composition comprising a compound covalently bound to a substrate, said compound having a structure according to Formula (I):

in which n is an integer selected from 0 and 1;
X is selected from the group consisting of NR f R 21 R 22 , SR f or OR f
wherein, when X is NR f R 21 R 22 ,
R f is selected from the group consisting of unsubstituted alkyl or substituted alkyl with at least one member selected from carboxylic acid, sulfonic acid, phosphoric acid, and an amino moiety and unsubstituted heteroalkyl or substituted heteroalkyl with at least one member selected from carboxylic acid, sulfonic acid, phosphoric acid, and an amino moiety;
R 21 is selected from the group consisting of H, substituted or unsubstituted alkyl, and substituted or unsubstituted heteroalkyl; and
R 22 is selected from the group consisting of a lone pair of electrons, H, substituted or unsubstituted alkyl, and substituted or unsubstituted heteroalkyl:

wherein when X is SR f or OR f ,
R f is substituted alkyl or substituted heteroalkyl each with at least one member selected from carboxylic acid, sulfonic acid, phosphoric acid and an amino acid;

R 1 , R 2 and R 3 are selected independently from the group consisting of halogen, OR 10 , NR 10 R 11 , OC(O)R 12 , OS(O) 2 R 12 , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl and a bond to said substrate
wherein each R 10 and each R 11 is selected independently from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl and a bond to a silica gel substrate,
with the proviso that at least one of R 1 , R 2 and R 3 is unsubstituted C 1 -C 3 alkyl or OH, and further with the proviso that at least one of R 1 , R 2 and R 3 is covalently bound to said substrate;
each R 12 is selected independently from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and substituted or unsubstituted heterocycloalkyl;

L 1 and L 2 are linker groups independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and substituted or unsubstituted heterocycloalkyl; and
Y is O.

2. The composition of claim 1 , wherein
R 1 , R 2 and R 3 are selected independently from the group consisting of OR 10 , OC(O)R 12 , OS(O) 2 R 12 , and unsubstituted alkyl,
wherein each R 10 and each R 11 is selected independently from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl and a bond to a silica gel substrate;
each R 12 is selected independently from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and substituted or unsubstituted heterocycloalkyl;

L 1 is C 3 unsubstituted alkyl; and
L 2 is C 1 -C 8 unsubstituted alkyl.

3. The composition of claim 1 , wherein the structure is according to Formula (II):

4. The composition of claim 2 , wherein R 21 is unsubstituted alkyl and R 22 is unsubstituted alkyl.

5. The composition of claim 2 , wherein R 21 is unsubstituted C 1 or C 2 or C 3 alkyl and R 22 is unsubstituted C 1 or C 2 or C 3 alkyl.

6. The composition of claim 2 , wherein R 22 is a lone pair of electrons.

7. The composition of claim 2 , wherein R 21 is H and R 22 is a lone pair of electrons.

8. The composition of claim 1 , wherein R f is alkyl substituted with a member selected from carboxylic acid, sulfonic acid, phosphoric acid, an amino acid and a combination thereof.

9. The composition of claim 1 , wherein the structure is according to Formula (III):

10. The composition of claim 9 , wherein R f is alkyl substituted with a carboxylic acid.

11. The composition of claim 1 , with the proviso that at least two of R 1 , R 2 and R 3 is covalently bound to said substrate.

12. The composition of claim 1 , with the proviso that R 1 and Rare covalently bound to said substrate and further, R 3 is unsubstituted C 1 -C 3 alkyl or OH.

13. The composition of claim 1 , with the proviso that R 1 and R 2 are covalently bound to said substrate, and R 3 is methyl.

14. The composition of claim 1 , with the proviso that R 1 and R 2 are covalently bound to said substrate, and R 3 is OH.

15. The composition of claim 1 , wherein n is 0, and L 2 is C 1 -C 8 unsubstituted alkyl.

16. The composition of a claim 1 , wherein n is 0, and L 2 is C 5 -C 8 unsubstituted alkyl.

17. The composition of claim 1 , wherein n is 0, and L 2 is C 8 unsubstituted alkyl.

18. The composition of claim 1 , wherein n is 1, and L 1 is C 2 -C 5 unsubstituted alkyl, and L 2 is C 1 -C 3 unsubstituted alkyl.

19. The composition of claim 1 , wherein n is 1, and L 1 is C 3 unsubstituted alkyl, and L 2 is C 1 unsubstituted alkyl.

20. A chromatographic system comprising the composition of claim 1 in a chromatographic column in fluidic communication with one or more of:
a) a suppressor;
b) an injection valve;
c) a source of eluent; and
d) a detector.

21. The composition of claim 3 , wherein, R f is an unsubstituted alkyl.

22. The composition of claim 3 , wherein, R f is an unsubstituted heteroalkyl.

Assignees

• Liu Xiaodong
• Cao Liang
• Pohl Christopher A
• Dionex Corp

Inventors

• Liu Xiaodong
• Cao Liang
• Pohl Christopher A

Classifications

• B01J20/289 Primary

  bonded via a spacer · CPC title

• B01J2220/54

  Sorbents specially adapted for analytical or investigative chromatography · CPC title

• B01J39/26

  Cation exchangers for chromatographic processes · CPC title

• B01J20/3259

  comprising at least two different types of heteroatoms selected from nitrogen, oxygen or sulfur with at least one silicon atom · CPC title

• B01J20/3285

  Coating or impregnation layers comprising different type of functional groups or interactions, e.g. different ligands in various parts of the sorbent, mixed mode, dual zone, bimodal, multimodal, ionic or hydrophobic, cationic or anionic, hydrophilic or hydrophobic · CPC title