Chromatographic materials for the separation of unsaturated molecules

Patent metadata

Field	Value
Publication number	US-2018345248-A1
Application number	US-201816058069-A
Country	US
Kind code	A1
Filing date	Aug 8, 2018
Priority date	May 15, 2012
Publication date	Dec 6, 2018
Grant date	—

Abstract

The present disclosure relates to a method of separating a compound of interest, particularly unsaturated compound(s) of interest, from a mixture. The compound is separated using a column having a chromatographic stationary phase material for various different modes of chromatography containing a first substituent and a second substituent. The first substituent minimizes compound retention variation over time under chromatographic conditions. The second substituent chromatographically and selectively retains the compound by incorporating one or more aromatic, polyaromatic, heterocyclic aromatic, or polyheterocyclic aromatic hydrocarbon groups, each group being optionally substituted with an aliphatic group.

First claim

1 - 30 . (canceled)

31 . A method of separating a compound of interest from a mixture, the method comprising:
(a) providing the mixture containing the compound of interest; (b) introducing a portion of the mixture to a chromatographic system having a chromatographic column; and (c) eluting the separated compound of interest from the chromatographic column;
wherein the chromatographic column has a stationary phase comprising

or a mixture thereof;
wherein X is a chromatographic substrate containing silica, metal oxide, an inorganic-organic hybrid material, a group of block copolymers, or a combination thereof.

32 . The method of claim 31 , wherein the compound of interest is a lipid, vitamin, or polycyclic aromatic hydrocarbon.

33 . The method of claim 32 , wherein the lipid is a saturated or an unsaturated fatty acid, monoacylglyceride, diacylglyceride, triacylglyceride, phospholipid, sphingolipid or steroid.

34 . The method of claim 32 , wherein the vitamin is a water soluble vitamin selected from the group consisting of vitamin C, vitamin B, or derivatives or combinations thereof.

35 . The method of claim 32 , wherein the vitamin is a fat soluble vitamin selected from the group consisting of vitamin A, vitamin D, vitamin K, vitamin E, betacarotene, or derivatives or combinations thereof.

36 . The method of claim 31 , wherein the chromatographic stationary phase is adapted for supercritical fluid chromatography.

37 . The method of claim 31 , wherein the chromatographic stationary phase is adapted for carbon dioxide based chromatography.

38 . A method for mitigating or preventing retention drift in normal phase chromatography, high-pressure liquid chromatography, solvated gas chromatography, supercritical fluid chromatography, sub-critical fluid chromatography, carbon dioxide based chromatography, hydrophilic interaction liquid chromatography, or hydrophobic interaction liquid chromatography comprising:
chromatographically separating the mixture using the chromatographic system comprising the stationary phase according to claim 31 , thereby mitigating or preventing retention drift.

39 . A method of separating a compound of interest from a mixture, the method comprising:
(a) providing the mixture containing the compound of interest; (b) introducing a portion of the mixture to a chromatographic system having a chromatographic column; and (c) eluting the separated compound of interest from the chromatographic column;
wherein the chromatographic column has a stationary phase comprising

or a mixture thereof;
wherein X is a chromatographic substrate containing silica, metal oxide, an inorganic-organic hybrid material, a group of block copolymers, or a combination thereof.

40 . The method of claim 39 , wherein the compound of interest is a lipid, vitamin, or polycyclic aromatic hydrocarbon.

41 . The method of claim 40 , wherein the lipid is a saturated or an unsaturated fatty acid, monoacylglyceride, diacylglyceride, triacylglyceride, phospholipid, sphingolipid or steroid.

42 . The method of claim 40 , wherein the vitamin is a water soluble vitamin selected from the group consisting of vitamin C, vitamin B, or derivatives or combinations thereof.

43 . The method of claim 40 , wherein the vitamin is a fat soluble vitamin selected from the group consisting of vitamin A, vitamin D, vitamin K, vitamin E, betacarotene, or derivatives or combinations thereof.

44 . The method of claim 39 , wherein the chromatographic stationary phase is adapted for supercritical fluid chromatography.

45 . The method of claim 39 , wherein the chromatographic stationary phase is adapted for carbon dioxide based chromatography.

46 . A method for mitigating or preventing retention drift in normal phase chromatography, high-pressure liquid chromatography, solvated gas chromatography, supercritical fluid chromatography, sub-critical fluid chromatography, carbon dioxide based chromatography, hydrophilic interaction liquid chromatography, or hydrophobic interaction liquid chromatography comprising:
chromatographically separating the mixture using the chromatographic system comprising the stationary phase according to claim 39 , thereby mitigating or preventing retention drift.

Assignees

• Waters Technologies Corp

Inventors

• Brousmiche Darryl W
• Fairchild Jacob N
• Hill Jason F
• Isaac Giorgis
• Morris Michael F
• Wyndham Kevin D

Classifications

• B01J20/28083

  being in the range 2-50 nm, i.e. mesopores · CPC title

• B01D15/305

  Hydrophilic interaction chromatography [HILIC] · CPC title

• B01D15/26 Primary

  characterised by the separation mechanism · CPC title

• B01J20/28061

  being in the range 100-500 m2/g · CPC title

• B01J20/28069

  Pore volume, e.g. total pore volume, mesopore volume, micropore volume · CPC title