Method for isolating diamondoids

Patent metadata

Field	Value
Publication number	US-10080980-B2
Application number	US-201314651428-A
Country	US
Kind code	B2
Filing date	Dec 10, 2013
Priority date	Dec 11, 2012
Publication date	Sep 25, 2018
Grant date	Sep 25, 2018

Abstract

Method for separating the diamondoids by liquid chromatography from a sample of iso-alkanes and cycloalkanes, or from a mixture of organic compounds, this method comprising introducing the sample into a column comprising a stationary phase comprising a material capable of forming inclusion complexes with the diamondoids, eluting with an eluent, and collecting the eluted fraction.

First claim

The invention claimed is:

1. Method for isolating diamondoids from a mixture of organic compounds by a method comprising the following steps:
a first separation step by liquid chromatography of a fraction of iso-alkanes and cycloalkanes from the mixture of organic compounds, said mixture of organic compounds comprising iso-alkanes, cycloalkanes, n-alkanes, aromatic compounds, polar compounds, high molecular weight and/or heteroatomic compounds, and said first separation step comprising:
introducing the mixture of organic compounds into a first single column comprising three stationary phases, the first stationary phase being of a material capable of adsorbing n-alkanes, the second stationary phase being of a material capable of adsorbing the aromatic compounds and the polar compounds, and the third stationary phase being of a material capable of adsorbing high molecular weight and/or heteroatomic compounds in which the third stationary phase comprises a silica selected from a silica grafted with aminoalkyl groups and a silica grafted with cyanoalkyl groups,
eluting with an eluent selected from isooctane, n-octane and mixtures thereof, and
collecting the fraction or fractions of eluted iso-alkanes and cycloalkanes, and
in said first separation step, the third stationary phase is arranged before the second stationary phase, the second stationary phase is arranged before the first stationary phase, following the direction of elution, and

a second separation step by liquid chromatography of the diamondoids from the said fraction or fractions of iso-alkanes and cycloalkanes, the second separation step comprising:
introducing the sample into a second column comprising a stationary phase comprising a material capable of forming inclusion complexes with the diamondoids, said material being selected from the cyclodextrins,
eluting with an eluent selected from mixtures of n-alkane and alkanol, and
collecting the eluted fractions comprising the diamondoids.

2. Method according to claim 1 , in which the first separation step is a separation step by low pressure chromatography, in which the liquid phase is eluted under a pressure of less than 25 bars.

3. Method according to claim 1 , which comprises an intermediate step of preparation of the fraction of iso-alkanes and cycloalkanes, this preparation comprising a filtration and/or a concentration by partial evaporation of the solvent.

4. Method according to claim 1 in which the mixture of organic compounds originates, directly or after treatment, from a deposit of crude oil, shale oils, or petroleum cuts.

5. Method according to claim 1 , in which the first stationary phase comprises a zeolite and the second stationary phase comprises a silica impregnated with silver nitrate.

6. Method according to claim 1 , in which the material capable of forming inclusion complexes with the diamondoids is β-cyclodextrin.

7. Method according to claim 1 , in which the eluent is selected from mixtures of C3-C8 n-alkane and C1-C4 alkanol with an alkane/alkanol volume ratio ranging from 90/10 to 99.5/0.5.

8. Method according to claim 7 , in which the eluent is a pentane/isopropanol mixture.

9. Method according to claim 8 , in which the volume ratio in the pentane/isopropanol mixture is of 98%/2% vol/vol.

10. Method according to claim 1 , in which the second column involved in the second separation step is an High Performance Liquid Chromatography (HPLC) column connected to an High Performance Liquid Chromatography (HPLC) device, the method being implemented with a pressure in the column ranging from 10 to 30 bars.

Assignees

• Total Sa

Inventors

• Serres Piole Coralie
• Berrut Jean-Bernard

Classifications

• C07C2603/90

  containing more than four rings · CPC title

• B01D15/3828 Primary

  Ligand exchange chromatography, e.g. complexation, chelation or metal interaction chromatography · CPC title

• C07C13/68

  with a bridged ring system · CPC title

• B01J20/286

  Phases chemically bonded to a substrate, e.g. to silica or to polymers · CPC title

• B01D15/1871

  placed in series · CPC title