IP Library Granted Patent US 8,536,372
Granted Patent B2
US 8,536,372 · App. 13/647,546 · Granted Sep 17, 2013

Procatalyst composition with substituted 1,2-phenylene aromatic diester internal donor and method

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Quick Facts
Patent No.
US 8,536,372
App. No.
13/647,546
Granted
Sep 17, 2013
Kind
B2
Abstract

Disclosed are procatalyst compositions having an internal electron donor which include a substituted phenylene aromatic diester and optionally an electron donor component. Ziegler-Natta catalyst compositions containing the present procatalyst compositions exhibit high activity and produce propylene-based olefins with broad molecular weight distribution.

Claims (27)

1. A procatalyst composition comprising:

a combination of a magnesium moiety, a titanium moiety and an internal electron donor comprising a substituted phenylene aromatic diester having the structure (I)

wherein R 1 -R 14 are the same or different, and at least one of R 1 -R 4 is selected from the group consisting of a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, and combinations thereof.

2. The procatalyst composition of claim 1 wherein each of R 5 -R 14 is hydrogen.

3. The procatalyst composition of claim 1 wherein at least one of R 1 -R 4 and at least one of R 5 -R 14 is selected from the group consisting of a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a heteroatom, and combinations thereof.

4. The procatalyst composition of claim 1 wherein at least one of R 1 -R 4 , at least one of R 5 -R 9 , and at least one of R 10 -R 14 is selected from the group consisting of a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a heteroatom, and combinations thereof.

5. The procatalyst composition of claim 1 wherein each of R 1 , R 3 and R 4 is hydrogen and R 2 is selected from the group consisting of a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, and combinations thereof.

6. The procatalyst composition of claim 5 wherein each of R 5 -R 14 is selected from the group consisting of hydrogen, a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a halogen, and combinations thereof.

7. The procatalyst composition of claim 1 wherein each of R 2 , R 3 and R 4 is hydrogen and R 1 is selected from the group consisting of a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, and combinations thereof.

8. The procatalyst composition of claim 7 wherein at least one of R 5 -R 14 is selected from the group consisting of hydrogen, a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a halogen, and combinations thereof.

9. The procatalyst composition of claim 1 wherein R 1 is a methyl group and each of R 5 -R 14 is hydrogen.

10. A procatalyst composition comprising:

a combination of a magnesium moiety, a titanium moiety and an internal electron donor comprising a substituted 1,2-phenylene aromatic diester having the structure (I)

wherein R 1 -R 14 are the same or different; and

at least two of R 1 -R 4 are selected from the group consisting of a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, and combinations thereof.

11. The procatalyst composition of claim 10 wherein each of R 5 -R 14 is hydrogen.

12. The procatalyst composition of claim 10 wherein each of R 1 and R 3 is selected from the group consisting of a C 1 -C 8 alkyl group, a C 3 -C 6 cycloalkyl group, a substituted C 3 -C 6 cycloalkyl group, and combinations thereof.

13. The procatalyst composition of claim 10 wherein each of R 1 and R 3 is an isopropyl group.

14. The procatalyst composition of claim 10 wherein each of R 2 and R 4 is hydrogen and each of R 1 and R 3 is selected from the group consisting of substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, and combinations thereof.

15. The procatalyst composition of claim 14 wherein each of R 5 -R 14 is hydrogen.

16. The procatalyst composition of claim 10 wherein at least one of R 5 -R 14 is selected from the group consisting of a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a halogen, and combinations thereof.

17. A catalyst composition comprising the procatalyst composition of claim 1 ;

a cocatalyst; and

an activity limiting agent comprising an aliphatic mono-carboxylic acid ester.

18. The catalyst composition of claim 17 wherein each of R 5 -R 12 is hydrogen.

19. The catalyst composition of claim 18 wherein each of R 1 and R 3 is selected from the group consisting of a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a heteroatom, and combinations thereof.

20. The catalyst composition of claim 17 comprising an external electron donor comprising an alkoxysilane.

Assignments (13)
NOTES SECURITY INTEREST Recorded Jan 29, 2026
From: W. R. GRACE & CO.-CONN.; ADVANCED REFINING TECHNOLOGIES LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 074532/0229 →
SECURITY INTEREST Recorded Aug 19, 2025
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 072519/0265 →
SECURITY INTEREST Recorded Aug 19, 2025
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 072519/0240 →
SECURITY AGREEMENT (NOTES) Recorded Aug 19, 2025
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 072520/0653 →
SECURITY INTEREST Recorded Apr 2, 2023
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 063199/0472 →
NOTES SECURITY AGREEMENT Recorded Sep 23, 2021
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 057594/0156 →
TERM LOAN SECURITY AGREEMENT Recorded Sep 23, 2021
From: W. R. GRACE & CO.-CONN.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 057594/0104 →
RELEASE OF SECURITY INTEREST Recorded Sep 23, 2021
From: GOLDMAN SACHS BANK USA
To: W. R. GRACE & CO.-CONN.
Reel/Frame 057594/0026 →
SECURITY INTEREST Recorded Apr 3, 2018
From: W. R. GRACE & CO.-CONN.
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 045828/0683 →
RELEASE OF SECURITY AGREEMENT RECORDED AT REEL/FRAME NO.: 032159/0384 Recorded Apr 3, 2018
From: GOLDMAN SACHS BANK USA, AS THE COLLATERAL AGENT
To: W.R. GRACE & CO.-CONN.
Reel/Frame 045832/0887 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE NAME TO "W. R. GRACE & CO. - CONN." PREVIOUSLY RECORDED ON REEL 032554 FRAME 0730. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNEE NAME WAS PREVIOUSLY INCORRECTLY LISTED IN THE RECORDATION COVER SHEET DATED 3/28/2014 AS "W. R. GRACE & CO. CONN.". Recorded Apr 2, 2014
From: DOW GLOBAL TECHNOLOGIES LLC; UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY LLC
To: W. R. GRACE & CO. - CONN.
Reel/Frame 032589/0554 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 28, 2014
From: DOW GLOBAL TECHNOLOGIES LLC; UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY LLC
To: W. R. GRACE & CO. CONN.
Reel/Frame 032554/0730 →
SECURITY AGREEMENT Recorded Feb 4, 2014
From: W.R. GRACE & CO.-CONN.
To: GOLDMAN SACHS BANK USA, AS THE COLLATERAL AGENT
Reel/Frame 032159/0384 →