Compositions and methods for the liquid-phase separation of isomers of aromatic molecules

Patent metadata

Field	Value
Publication number	US-10183235-B2
Application number	US-201515532647-A
Country	US
Kind code	B2
Filing date	Nov 25, 2015
Priority date	Dec 5, 2014
Publication date	Jan 22, 2019
Grant date	Jan 22, 2019

Abstract

The present invention includes a composition and process for separating p-isomers of vinylbenzenes from a mixture of isomers comprising the steps of: providing a porous microwaved Mg(II) 2,4-pyridinedicarboxylic acid coordination polymer having a 1-D pore structure and showing reversible soft-crystal behavior by preferentially binding p-isomers of vinylbenzene; adding a mixture of vinylbenzenes isomers to the porous microwaved Mg (II) 2,4-pyridinedicarboxylic acid coordination polymer; adsorbing the p-isomers of vinylbenzene from the mixture of vinylbenzenes isomers; selectively adsorb the p-isomers of vinylbenzene in the 1-D pore structure; removing the mixture of vinylbenzenes isomers; and desorbing the p-isomers of vinylbenzene from the 1-D pore structure to purify the p-isomers of vinylbenzene.

First claim

What is claimed is:

1. A method for separating p-isomers from a mixture comprising the steps of:
providing a porous microwaved Mg(II) 2,4-pyridinedicarboxylic acid coordination polymer having a 1-D pore structure showing reversible soft-crystal behavior by preferentially binding p-isomers;
adding a mixture of isomers of an organic molecule to the porous microwaved Mg (II) coordination polymer;
adsorbing the p-isomers from the mixture of organic molecule isomers;
crystallize the p-isomers in the 1-D pore structure;
removing the remaining mixture of organic molecule isomers; and
desorbing the p-isomers from the 1-D pore structure to purify the p-isomers.

2. The method of claim 1 , wherein the mixture of isomers of the organic molecule comprises a mixture of vinylbenzene isomers.

3. The method of claim 2 , wherein the vinylbenzene comprises divinylbenzene, ethylvinylbenzene or both.

4. The method of claim 2 , wherein the mixture of vinylbenzene isomers comprises p-isomers, o-isomers, and m-isomers; p-isomers and o-isomers; or p-isomers and m-isomers.

5. The method of claim 1 , wherein the porous microwaved Mg(II) 2,4-pyridinedicarboxylic acid coordination polymer selectively adsorbs p-isomers of the organic molecule, which crystallize inside the pores at ambient temperature and pressure.

6. The method of claim 1 , wherein the organic molecule comprises pyridine, benzene, xylene, ethylvinylbenzene, divinylbenzene, or a combination thereof.

7. The method of claim 1 , wherein the p-isomer is p-xylene, p-ethylvinylbenzene, p-divinylbenzene or a combination thereof.

8. The method of claim 1 , wherein o-xylene, m-xylene, o-divinylbenzene, m-divinylbenzene, o-ethylvinylbenzene and m-ethylvinylbenzene are excluded from the porous microwaved Mg(II) 2,4-pyridinedicarboxylic acid coordination polymer.

9. A method of making a porous Mg(II) coordination polymer comprising the steps of:
providing a reaction chamber containing a Mg(II) complex in water;
adding 2,4-pyridinedicarboxylic acid to the Mg(II) complex;
exposing the reaction chamber to microwaves;
cooling the reaction chamber to form a crystalline solid; and
purifying the crystalline solid to form a porous microwaved Mg(II) coordination polymer, wherein the porous microwaved Mg(II) coordination polymer selectively adsorbs one or more organic molecule isomers, which crystallize inside the pores at ambient temperature and pressure.

10. The method of claim 9 , wherein the Mg(II) complex comprises
Mg(NO 3 )×H 2 O hydrate.

11. The method of claim 9 , wherein the one or more organic molecule isomers are the p-isomers.

12. The method of claim 11 , wherein the p-isomers are p-xylene, p-ethylvinylbenzene, p-divinylbenzene or a combination thereof.

13. The method of claim 9 , wherein the one or more organic molecules comprise pyridine, benzene, xylene, ethylvinylbenzene, divinylbenzene or a combination thereof.

14. The method of claim 9 , wherein o-xylene, m-xylene, o-divinylbenzene, m-divinylbenzene, o-ethylvinylbenzene and are m-ethylvinylbenzene excluded from the porous microwaved Mg(II) coordination polymer.

15. The method of claim 9 , wherein the method further comprises adding KOH to the reaction chamber in addition to the 2,4-pyridine carboxylic acid.

16. The composition made by the method of claim 9 .

17. A porous coordination polymer comprising:
metal complexes formed by coordination bonding between Mg (II) and 2,4-pyridinedicarboxylic, wherein the porous coordination polymer has a pore structure formed by integration of a plurality of the metal complexes that selectively binds a p-isomer of an organic molecule.

18. The porous coordination polymer of claim 17 , wherein the pore structure has a diameter of about 2 nm.

Assignees

• Univ Texas

Inventors

• Humphrey Simon M

Classifications

• B01D15/08 Primary

  Selective adsorption, e.g. chromatography · CPC title

• B01J20/28064

  being in the range 500-1000 m2/g · CPC title

• C07C7/12

  by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers · CPC title

• B01J20/28011

  Other properties, e.g. density, crush strength · CPC title

• B01D17/0202

  by ab- or adsorption · CPC title