Process for separating a divinyl hydrocarbon from monovinyl hydrocarbons and/or non-vinyl compounds

Patent metadata

Field	Value
Publication number	US-2016199754-A1
Application number	US-201414913617-A
Country	US
Kind code	A1
Filing date	Aug 27, 2014
Priority date	Aug 29, 2013
Publication date	Jul 14, 2016
Grant date	—

Abstract

A process for separating a divinyl hydrocarbon from a composition mixture stream containing at least a divinyl hydrocarbon and other components, the process including (a) passing a composition mixture feed stream containing at least (i) a divinyl hydrocarbon; and (ii) a monovinyl hydrocarbon, and/or (iii) a non-vinyl hydrocarbon through a process-scale chromatography unit; wherein the process scale chromatography unit includes a ligand exchange media comprising a metal adapted to form a ligand with an olefin functionality; wherein the metal of the ligand exchange media is loaded on an adsorbent; and wherein the divinyl hydrocarbon is adsorbed onto the ligand exchange media; (b) passing a weak first elution solvent through the unit to elute the monovinyl hydrocarbon and/or the non-vinyl hydrocarbon from the unit; (c) passing a strong second elution solvent through the unit to elute the divinyl hydrocarbon product stream from the unit; and (d) recovering the divinyl hydrocarbon product stream having been separated from the other components in the composition mixture stream; and an apparatus therefor.

First claim

1 . A process for separating a divinyl hydrocarbon from a composition mixture stream containing at least a divinyl hydrocarbon and other components, the process comprising the steps of:
(a) passing a composition mixture feed stream containing at least (i) a divinyl hydrocarbon; and (ii) a monovinyl hydrocarbon, and/or (iii) a non-vinyl hydrocarbon through a process-scale chromatography unit with or without heating; wherein the process scale chromatography unit includes a ligand exchange media comprising a metal adapted to form a ligand with an olefin functionality; wherein the metal of the ligand exchange media is loaded on an adsorbent; and wherein the divinyl hydrocarbon is adsorbed onto the ligand exchange media; (b) passing a weak first elution solvent through the unit to elute the monovinyl hydrocarbon and/or the non-vinyl hydrocarbon from the unit; (c) passing a strong second elution solvent through the unit to elute the divinyl hydrocarbon product stream from the unit; and (d) recovering the divinyl hydrocarbon product stream having been separated from the other components in the composition mixture stream.

2 . The process of claim 1 , wherein the divinyl hydrocarbon is a divinylarene, a divinylcycloaliphatic, a divinylaliphatic having carbon atoms of greater than 4, a polyvinyl hydrocarbon, an acetylenic hydrocarbon, or mixtures thereof.

3 . The process of claim 2 , wherein the divinylarene is divinylbenzene.

4 . The process of claim 1 , wherein the monovinyl hydrocarbon is an ethylvinylarene, and wherein the ethylvinylarene is ethylvinylbenzene.

5 . The process of claim 1 , wherein mixture feed stream contains naphthalene, an ethylvinylarene, a diethylarene, and light components.

6 . The process of claim 1 , wherein the non-vinyl hydrocarbon is a diethylarene and wherein the diethylarene is diethylbenzene.

7 . The process of claim 1 , including the step of recovering the monovinyl hydrocarbon having been separated from the composition mixture stream; and wherein the monovinyl hydrocarbon is an ethylvinylarene, a diethylarene, or a mixture thereof.

8 . The process of claim 1 , wherein step (a) is carried out without heating.

9 . The process of claim 1 , wherein the metal of the ligand exchange media is loaded onto an adsorbent mechanically, or wherein the metal of the ligand exchange media is loaded onto an adsorbent electrostatically.

10 . The process of claim 1 , wherein the solvent used in step (b) and step (c) is the same solvent, and wherein the solvent is acetone, acetonitrile, ethyl acetate, tetrahydrofuran, methanol, ethanol, isopropanol, water, or mixtures thereof.

11 . The process of claim 1 , wherein the metal of the ligand exchange media is silver, copper, salts of silver, salts of copper, platinum, palladium, gold, ruthenium, mercury, iridium, any metal known to be active to form complexes with organic compounds, or mixtures thereof.

12 . The process of claim 11 , wherein the silver or copper is disposed on a support material.

13 . The process of claim 1 , wherein the ligand exchange media is a silver-modified adsorbent, a copper-modified adsorbent, or mixtures thereof.

14 . The process of claim 1 , wherein the metal of the ligand exchange media is regenerated.

15 . The process of claim 1 , wherein the composition mixture stream includes further (iv) a solvent and wherein the solvent is higher boiling point than divinylarene.

16 . The process of claim 1 , wherein the composition mixture stream includes further (iv) a solvent and wherein the solvent is lower boiling point than divinylarene.

17 . The process of claim 1 , wherein the composition of the composition mixture stream comprises from about 10 weight percent to about 50 weight percent divinyl hydrocarbon; from about 5 weight percent to about 50 weight percent monovinyl hydrocarbon, and from about 0 weight percent to about 20 weight percent non-vinyl hydrocarbon.

18 . The process of claim 1 , wherein the composition of the divinylarene product stream on a solvent-free basis comprises from about 50 weight percent to about 96 weight percent divinyl hydrocarbon; about 0 weight percent to about 20 weight percent from about 4 weight percent to about 50 weight percent monovinyl hydrocarbon; and from about 0 weight percent to about 20 weight percent non-vinyl hydrocarbon.

19 . The process of claim 1 , wherein the monovinyl hydrocarbon in the composition mixture stream comprises meta isomers, para isomers, ortho isomers or any combination thereof; wherein the non-vinyl hydrocarbon in the composition mixture stream comprises meta isomers, para isomers, ortho isomers, or any combination thereof; and
wherein the divinyl hydrocarbon in the composition mixture stream comprises meta isomers, para isomers, ortho isomers, or any combination thereof.

20 . The process of claim 19 , including the steps of:
(i) separating at least a portion of one or more of the meta isomer, para isomer, ortho isomer, or combination thereof from the other isomers and/or other components in the product stream; and (ii) adjusting the meta/para isomer ratio of the divinyl hydrocarbon in the composition mixture stream to a meta/para isomer ratio of from about 0.5 to about 4.0.

21 . An apparatus for separating a divinyl hydrocarbon from a composition mixture stream containing at least a divinyl hydrocarbon and other components, the apparatus comprising:
(A) a means for passing a composition mixture feed stream containing at least
(i) a divinyl hydrocarbon; and
(ii) a monovinyl hydrocarbon, and/or
(iii) a non-vinyl hydrocarbon through a process-scale chromatography unit with or without heating; wherein the process scale chromatography unit includes a ligand exchange media comprising a metal adapted to form a ligand with an olefin functionality; wherein the metal of the ligand exchange media is loaded on an adsorbent; and wherein the ligand exchange media is adapted for adsorbing the divinyl hydrocarbon onto the ligand exchange media;
(b) a means for passing a weak first elution solvent through the unit to elute the monovinyl hydrocarbon and/or the non-vinyl hydrocarbon from the unit; (c) a means for passing a strong second elution solvent through the unit to elute the divinyl hydrocarbon product stream from the unit; and (d) a means for recovering the divinyl hydrocarbon product stream having been separated from the other components in the composition mixture stream.

Assignees

• Blue Cube Ip Llc

Inventors

• Donaldson Megan E
• Campbell Robert M
• Holden Bruce S
• Frank Timothy C
• Hook Bruce D

Classifications

• B01D15/38 Primary

  involving specific interaction not covered by one or more of groups {B01D15/265 and} B01D15/30 - B01D15/36, e.g. affinity, ligand exchange or chiral chromatography · CPC title

• B01D15/3828

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

• B01D15/1821

  Simulated moving beds · 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

• B01J20/18

  Synthetic zeolitic molecular sieves · CPC title