IP Library Granted Patent US 9,453,089
Granted Patent B2
US 9,453,089 · App. 14/118,254 · Granted Sep 27, 2016

Production of highly reactive low molecular weight PIB oligomers

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Quick Facts
Patent No.
US 9,453,089
App. No.
14/118,254
Granted
Sep 27, 2016
Kind
B2
Abstract

In one preferred embodiment, the present invention provides a process for the liquid phase polymerization of isobutylene to manufacture highly reactive PIB oligomers having Mn under 1000, using a catalyst composition comprising a Friedel-Crafts catalyst a complexing agent, a chain transfer agent and a polymerization-retarding agent. A chain transfer agent may be selected from: α-DIB and β-DIB and mixtures thereof. A polymerization-retarding agent may be selected from:

Claims (21)

1. A liquid phase polymerization process of isobutylene to manufacture highly reactive polyisobutylene (PIB) having Mn under 1000 and at least 50% terminal double bonds, said process comprising:

a) providing a feedstock comprising isobutylene;

b) providing a catalyst composition comprising a Friedel-Crafts catalyst and a complexing agent therefor;

c) providing an olefinic chain transfer agent (“CTA”);

d) providing a polymerization-retarding agent;

e) introducing said feedstock, said catalyst composition, said chain transfer agent and said polymerization-retarding agent into a reaction zone to form a reaction mixture;

f) intimately intermixing the reaction mixture in said reaction zone;

g) optionally adding a modifier;

h) maintaining the reaction mixture in its intimately intermixed condition to thereby cause the isobutylene therein to undergo polymerization to form polyisobutylene; and

i) withdrawing a product stream comprising low molecular weight, highly reactive polyisobutylene from said reaction zone.

2. The process of claim 1 , wherein said PIB has Mn under 800 and the polymerization-retarding agent comprises a phenolic compound.

3. The process of claim 1 , wherein said PIB has Mn weight under 500.

4. The process of claim 1 , wherein said Friedel-Crafts catalyst comprises BF 3 and said complexing agent is an alcohol.

5. The process of claim 1 , wherein said CTA is selected from the group consisting of 2,4,4-Trimethyl-1-pentene (“α-DIB”), 2.4.4.-Trimethyl-2-pentene (“β-DIB”), 2-ethyl-1-hexene, 2-methyl-1-pentene and mixtures thereof.

6. The process of claim 5 , wherein said CTA is α-DIB.

7. The process of claim 5 , wherein said CTA is β-DIB.

8. The process of claim 5 , wherein said CTA is a mixture of α-DIB and β-DIB.

9. The process according to claim 1 , wherein the polymerization-retarding agent comprises a phenolic compound.

10. The process according to claim 1 , wherein the polymerization-retarding agent is a hindered phenol.

11. The process according to claim 1 , wherein the polymerization-retarding agent is present in an amount of from 5 to 500 ppm by weight of the polyisobutylene composition.

12. The process according to claim 1 , wherein the polymerization-retarding agent is present in an amount of from 10 to 100 ppm by weight of the polyisobutylene composition.

Assignments (15)
RELEASE OF SECURITY INTEREST Recorded Dec 16, 2024
From: GLAS TRUST COMPANY LLC
To: TPC GROUP LLC
Reel/Frame 069602/0182 →
SECURITY INTEREST Recorded Dec 16, 2024
From: TPC GROUP LLC
To: JEFFERIES FINANCE LLC, AS AGENT
Reel/Frame 069594/0055 →
TERMINATION AND RELEASE OF GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS AT REEL/FRAME 060287/0820 Recorded Dec 20, 2022
From: GLAS AMERICAS LLC, AS COLLATERAL AGENT
To: TPC GROUP LLC
Reel/Frame 062171/0674 →
TERMINATION AND RELEASE OF SUPPLEMENTAL GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS AT REEL/FRAME 055119/0158 Recorded Dec 20, 2022
From: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS SUCCESSOR COLLATERAL AGENT TO U.S. BANK NATIONAL ASSOCIATION
To: TPC GROUP LLC
Reel/Frame 062171/0666 →
TERMINATION AND RELEASE OF SUPPLEMENTAL GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS AT REEL/FRAME 049949/0024 Recorded Dec 20, 2022
From: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS SUCCESSOR COLLATERAL AGENT TO U.S. BANK NATIONAL ASSOCIATION
To: TPC GROUP LLC
Reel/Frame 062171/0658 →
RELEASE OF SECURITY INTEREST AT REEL/FRAME 60113/0169 Recorded Dec 16, 2022
From: ECLIPSE BUSINESS CAPITAL LLC, AS AGENT
To: TPC GROUP LLC
Reel/Frame 062142/0523 →
SECURITY INTEREST Recorded Dec 16, 2022
From: TPC GROUP LLC
To: ECLIPSE BUSINESS CAPITAL LLC, AS COLLATERAL AGENT
Reel/Frame 062130/0001 →
SECURITY INTEREST Recorded Dec 16, 2022
From: TPC GROUP LLC
To: GLAS TRUST COMPANY LLC, AS COLLATERAL AGENT
Reel/Frame 062130/0137 →
RELEASE OF SECURITY INTEREST AT REEL/FRAME 49942/0467 Recorded Jun 8, 2022
From: BANK OF AMERICA, N.A., AS AGENT
To: TPC GROUP LLC
Reel/Frame 060392/0673 →
GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS Recorded Jun 6, 2022
From: TPC GROUP LLC
To: GLAS AMERICAS LLC, AS COLLATERAL AGENT
Reel/Frame 060287/0820 →
SECURITY INTEREST Recorded Jun 6, 2022
From: TPC GROUP LLC
To: ECLIPSE BUSINESS CAPITAL LLC, AS AGENT
Reel/Frame 060113/0169 →
SECURITY INTEREST Recorded Feb 2, 2021
From: TPC GROUP LLC
To: U.S. BANK NATIONAL ASSOCIATION, AS AGENT
Reel/Frame 055119/0158 →
SECURITY INTEREST Recorded Aug 2, 2019
From: TPC GROUP LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 049942/0467 →
SECURITY AGREEMENT Recorded Aug 2, 2019
From: TPC GROUP LLC
To: U.S. BANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 049949/0024 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 17, 2013
From: SHAIKH, SOHEL K.; LAWSON, REX
To: TPC GROUP LLC
Reel/Frame 032080/0864 →