IP Library Granted Patent US 10,668,452
Granted Patent B2
US 10,668,452 · App. 15/843,511 · Granted Jun 2, 2020

Methods and materials for improved catalytic oligomerization

Inventors: Ji Min (Dalian, CN); An Bowen (Dalian, CN); Brian Clancy-Jundt (Wilmington, DE); William M. Cross (Wilmington, DE); Daniel Travis Shay (Wilmington, DE); Cai Tian Xi (Dalian, CN)
Assignee: INVISTA NORTH AMERICA S.A.R.L.
B01J23/83B01J21/063B01J23/002B01J23/94B01J37/0201B01J37/0209B01J37/0236B01J37/08B01J37/086B01J37/088B01J37/12B01J37/16B01J38/02B01J38/04C07C2/24B01J21/04B01J2523/00C07C2521/04C07C2521/06C07C2523/83Y02P20/127Y02P20/52
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Quick Facts
Patent No.
US 10,668,452
App. No.
15/843,511
Granted
Jun 2, 2020
Kind
B2
Abstract

Described herein are materials and methods for improved catalytic oligomerization of an ethylene monomer and/or propylene monomer. The present disclosure teaches oligomerizing the ethylene monomer or propylene monomer to produce oligomers. Also described is a heterogeneous catalyst comprising sulfate modified nickel on titanium modified alumina and a surface modification with yttrium (Y) suitable for use in the disclosed oligomerization.

Claims (38)

1. A process for the catalytic oligomerization of an ethylene monomer comprising:

providing a first stream comprising ethane and ethylene monomer;

providing a heterogeneous catalyst, the heterogeneous catalyst comprising sulfate modified nickel on titanium modified alumina, and a surface modification with yttrium (Y);

contacting the first stream and the heterogeneous catalyst under oligomerization conditions;

oligomerizing the ethylene monomer in the first stream to produce an oligomer, the oligomer comprising one or more of a butene, hexene, octene, or a heavier olefinic compound, derivatives thereof or any combination thereof; and

optionally, providing an oligomer stream, wherein the concentration of oligomer in the oligomer stream is greater than the concentration of oligomer in the first stream.

2. A process for the catalytic oligomerization of a propylene monomer comprising:

providing a first stream comprising propane and propylene monomer;

providing a heterogeneous catalyst, the heterogeneous catalyst comprising sulfate modified nickel on titanium modified alumina, and a surface modification with yttrium (Y);

contacting the first stream and the heterogeneous catalyst under oligomerization conditions;

oligomerizing the propylene in the first stream to produce an oligomer, the oligomer comprising one or more of a hexene, nonene, or a heavier olefinic compound, derivatives thereof or any combination thereof; and

optionally, providing an oligomer stream, wherein the concentration of oligomer in the oligomer stream is greater than the concentration of oligomer in the first stream.

3. The process of claim 1 or claim 2 , wherein the first stream:

(i) comprises less than about 70% monomer; or

(ii) the stream is a dilute monomer stream.

4. The process of claim 1 or claim 2 , wherein the alumina:

(i)comprises a gamma alumina; or

(ii) is a gamma alumina.

5. The process of claim 1 or claim 2 , wherein the concentration of oligomer in the oligomer stream is about 100% or less.

6. The process of claim 1 or claim 2 , wherein the contacting occurs in a heterogeneous reactor, a continuous reactor, a fixed bed plug flow reactor or a continuous stirred tank reactor, fluidized bed reactor or reactive distillation system, or combinations thereof.

7. The process of claim 1 or claim 2 , wherein the nickel to yttrium molar ratio is from about 1:1 to about 50:1.

8. The process of claim 1 or claim 2 , wherein the oligomer is linear, branched, or a combination thereof.

9. The process of claim 1 or claim 2 , wherein the oligomerization conditions comprise at least one of:

(a) a temperature of less than about 50° C., and

(b) a liquid phase.

10. A heterogeneous catalyst for the oligomerization of ethylene or propylene comprising sulfate modified nickel on titanium modified alumina and a surface modification with yttrium (Y).

11. A composition comprising the catalyst of claim 10 and:

(i) ethylene monomer or propylene monomer and/or

(ii) an oligomer comprising one or more of a butene, hexene, octene, or a heavier olefinic compound, derivatives thereof or any combination thereof.

12. A method for processing the catalyst of claim 1 or 2 , comprising:

(a) activating the catalyst, the activating comprising:

(i) providing the catalyst,

(ii) contacting the catalyst with an oxidant, reducing agent or inert for at least one hour at about 200° C.; and

(iii) obtaining an activated catalyst, or

(b) regenerating the catalyst, the regenerating comprising

(i) providing the catalyst,

(ii) contacting the catalyst with nitrogen for at least about 30 minutes at about 200° C. or greater temperature, and optionally contacting said catalyst with an oxidant or inert; and

(iii) obtaining a regenerated heterogeneous catalyst.

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 13, 2021
From: INV NYLON CHEMICALS AMERICAS, LLC
To: KOCH TECHNOLOGY SOLUTIONS, LLC
Reel/Frame 056228/0391 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNOR'S NAME PREVIOUSLY RECORDED AT REEL: 055094 FRAME: 0793. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Mar 9, 2021
From: INVISTA NORTH AMERICA S.A.R.L.
To: INVISTA NORTH AMERICA, LLC
Reel/Frame 055537/0561 →
CHANGE OF NAME Recorded Feb 1, 2021
From: INVISTA NORTH AMERICAL S.A.R.L.
To: INVISTA NORTH AMERICA, LLC
Reel/Frame 055094/0793 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 7, 2021
From: INVISTA NORTH AMERICA, LLC
To: INV NYLON CHEMICALS AMERICAS, LLC
Reel/Frame 054914/0897 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 25, 2019
From: CLANCY-JUNDT, BRIAN
To: FLINT HILLS RESOURCES HOUSTON CHEMICAL, LLC
Reel/Frame 050824/0948 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 25, 2019
From: FLINT HILLS RESOURCES, LC
To: INVISTA NORTH AMERICA S.A.R.L.
Reel/Frame 050825/0414 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 25, 2019
From: CROSS, WILLIAM M., JR.
To: FLINT HILLS RESOURCES, LC
Reel/Frame 050825/0299 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 25, 2019
From: SHAY, DANIEL TRAVIS
To: INVISTA NORTH AMERICA S.A.R.L.
Reel/Frame 050825/0348 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 25, 2019
From: FLINT HILLS RESOURCES HOUSTON CHEMICAL, LLC
To: INVISTA NORTH AMERICA S.A.R.L.
Reel/Frame 050825/0398 →
Continuity (2)
Provisional Application 62436041 · Dec 19, 2016
Related Publication 20180169627A1 · Jun 21, 2018