# US 8,785,711 B2 · Ionic liquids, the method for preparing the same and method for removing acetylenes from olefin mixtures using the ionic liquids

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- Number: US 8,785,711 B2
- Document ID: US8785711B2
- Status: Granted
- Kind: B2
- Application number: 12/970,346
- Filed: 2010-12-16
- Published: 2012-04-05
- Granted: 2014-07-22
- Earliest claimed: 2010-10-04
- Assignees: Kolon Industries, Inc.
- Applicants: Hyun Joo Lee; Byoung Sung Ahn; Hoon Sik Kim; Jin-Hyung Kim; Gyeong Taek Gong
- Inventors: Hyun Joo Lee; Byoung Sung Ahn; Hoon Sik Kim; Jin-Hyung Kim; Gyeong Taek Gong
- Web page: https://patentgrep.com/patent/US8785711B2

## CPC

- C07D 295/088: to an acyclic saturated chain
- C07D 233/60: with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
- C07F 1/08: Copper compounds
- C07C 7/10: by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
- C07C 309/68: of a carbon skeleton substituted by singly-bound oxygen atoms
- C07D 207/08: with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D 233/02: having no double bonds between ring members or between ring members and non-ring members
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

There are provided an ionic liquid having ether group(s) in which a copper(I) compound is included, a method for preparing the same, and a method for removing traces amounts of acetylene-based hydrocarbon compounds included in olefin by absorption or extraction using the same. When the disclosed solution is used, oxidation of Cu(I) to Cu(II) is prevented since CuX is stabilized by the ionic liquid. Thus, selective removal efficiency of acetylenic compounds is improved greatly while the removal performance is retained for a long period of time. Further, since the solution according to the present disclosure is applicable as an extractant as well as an absorbent, the associated operation is simple and apparatus cost can be decreased.

## Claims

### Claim 1

A method for removing acetylenic compounds from an olefin mixture comprising the steps of:
contacting the olefin mixture with an ionic liquid; and
recovering an effluent with reduced acetylene content,
wherein the ionic liquid comprises one or more organometallic compound(s) represented by Chemical Formula (1), (2) or (3):
wherein
X is an anion selected from Cl, Br and I,
R1 is C1-C4 substituted or unsubstituted alkyl,
n is an integer from 1 to 6, and
Y is a sulfonate anion represented by Chemical Formula (4), wherein R2 is C1-C4 substituted or unsubstituted alkyl.

### Claim 2 (depends on 1)

The method for removing acetylenic compounds from an olefin mixture according to claim 1, wherein the amount of the olefin mixture is 0.2 to 5 times the amount of the ionic liquid based on weight.

### Claim 3 (depends on 1)

The method for removing acetylenic compounds from an olefin mixture according to claim 1, wherein the removal is performed at 0 to 100 ° C.

### Claim 4 (depends on 1)

The method for removing acetylenic compounds from an olefin mixture according to claim 1, wherein the removal is performed at 20 to 50 ° C.

### Claim 5 (depends on 1)

The method for removing acetylenic compounds from an olefin mixture according to claim 1, whereby C2-C5 acetylenic compounds are removed from the olefin mixture.

### Claim 6 (depends on 5)

The method for removing acetylenic compounds from an olefin mixture according to claim 5, wherein the C2-C5 acetylenic compounds are selected from acetylene, methylacetylene, ethylacetylene and isopropylacetylene.

### Claim 7 (depends on 1)

The method for removing acetylenic compounds from an olefin mixture according to claim 1, wherein the ionic liquid is regenerated after removing the acetylenic compounds from the olefin mixture.

### Claim 8 (depends on 7)

The method for removing acetylenic compounds from an olefin mixture according to claim 7, wherein the regeneration is performed at 50 to 200 ° C.

### Claim 9 (depends on 8)

The method for removing acetylenic compounds from an olefin mixture according to claim 8, wherein the regeneration is performed at 100 to 200 ° C.

### Claim 10 (depends on 7)

The method for removing acetylenic compounds from an olefin mixture according to claim 7, wherein the regeneration is performed under a pressure of 1 to 200 mmHg.

### Claim 11 (depends on 10)

The method for removing acetylenic compounds from an olefin mixture according to claim 10, wherein the regeneration is performed under a pressure of 50 to 100 mmHg.