Carbohydrate-mediated purification of petrochemicals

Patent metadata

Field	Value
Publication number	US-10239044-B2
Application number	US-201515316393-A
Country	US
Kind code	B2
Filing date	Jun 8, 2015
Priority date	Jun 6, 2014
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

A separation medium consisting of a cyclodextrin metal-organic framework (CD-MOF) for separating aromatic compounds and methods of preparing the same are presented. Bottom-up preparations include the following steps: (a) preparing a first mixture comprising a cyclodextrin, an alkali metal salt, water and an alcohol; (b) performing one of the following two steps: (i) stirring the first mixture; or (ii) adding an amount of a surfactant to the first mixture to form a second mixture; and (c) crystallizing the CD-MOF from the first mixture or the second mixture. Top-down preparations include the following steps: (a) preparing a first mixture comprising the cyclodextrin, an alkali metal salt, water and an alcohol; (b) crystallizing the CD-MOF from the first mixture; and (c) optionally performing particle size reduction of the crystallized CD-MOF. The CD-MOFs are amenable for use in methods for separating alkylaromatic and haloaromatic compounds from a mixture of hydrocarbons.

First claim

The invention claimed is:

1. A method of separating an aromatic compound from a mixture of hydrocarbons, comprising:
providing a separation medium consisting of a crystalline cyclodextrin metal-organic framework (CD-MOF) that is made according to a synthetic method consisting of the following steps (i) and (ii):
(i) preparing a first mixture comprising a cyclodextrin, an alkali metal salt, water, and an alcohol; and
(ii) stirring the first mixture and subsequently crystallizing the CD-MOF from the first mixture or adding an amount of a surfactant to the first mixture to form a second mixture and subsequently crystallizing the CD-MOF from the second mixture to produce the crystalline CD-MOF,
wherein the crystalline CD-MOF has a particle size in the range of from about 1 micron to about 25 microns,

contacting the mixture of hydrocarbons with the separation medium;
resolving the aromatic compound from the mixture of hydrocarbons; and
isolating the aromatic compound from the mixture of hydrocarbons.

2. The method of claim 1 , wherein the aromatic compound is an alkylaromatic compound or a haloaromatic compound.

3. The method of claim 1 , wherein the aromatic compound is an alkylaromatic compound.

4. The method of claim 3 , wherein the alkylaromatic compound is selected from the group consisting of toluene, ethylbenzene, ortho-xylene, meta-xylene, para-xylene, styrene, α-methylstyrene, cumene, ethyltoluene, 2-methylstyrene, 3-methylstyrene, 4-methylstyrene, and a combination thereof.

5. The method of claim 1 , wherein the aromatic compound is a haloaromatic compound.

6. The method of claim 5 , wherein the haloaromatic compound is selected from the group consisting of fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, 1,2-dibromobenzene, 1,3-dibromobenzene, 1,4-dibromobenzene, 1-bromo-2-iodobenzene, 1-bromo-3-iodobenzene, 1-bromo-4-iodobenzene, 1,2-diiodobenzene, 1,2-dichlorobenzene, α,α,α-trifluorotoluene, and a combination thereof.

7. The method of claim 1 , wherein the resolving the aromatic compound from the mixture of hydrocarbons comprises using a liquid chromatography mobile phase.

8. The method of claim 7 , wherein the liquid chromatography mobile phase comprises at least one compound selected from the group consisting of hexane, methylene chloride, methanol, and 2-propanol.

9. The method of claim 7 , wherein the separation medium is disposed in a chromatography column.

10. The method of claim 9 , wherein the chromatography column is configured for high performance liquid chromatography.

11. The method of claim 1 , wherein the resolving the aromatic compound from the mixture of hydrocarbons comprises using a gas phase.

12. The method of claim 1 , wherein the crystalline CD-MOF has a particle size selected from the group consisting of: a particle size in the range of from about 1 micron to about 10 microns; a particle size in the range of from about 5 microns to about 15 microns; a particle size in the range of from about 10 microns to about 15 microns; and a particle size of about 25 microns.

13. The method of claim 1 , wherein the crystalline CD-MOF has a particle size in the range of from about 10 microns to about 15 microns.

Assignees

• Univ Northwestern
• King Abdulaziz City Sci & Tech
• King Abdulaziz City For Science And Tech Kacst

Inventors

• Holcroft James M
• Hartlieb Karel J
• Stoddart James Fraser

Classifications

• B01J20/305

  Addition of material, later completely removed, e.g. as result of heat treatment, leaching or washing, e.g. for forming pores · CPC title

• C07C15/085

  Isopropylbenzene · CPC title

• C07C15/08

  Xylenes · CPC title

• C07C15/02

  Monocyclic hydrocarbons · CPC title

• C07C13/23

  with a cyclohexadiene ring · CPC title