Halogenated amide ester and internal electron donor with same
View Patent ↗Disclosed are halogenated amide esters that are suitable as internal electron donors in procatalyst compositions. Ziegler-Natta catalyst compositions containing the present procatalyst compositions exhibit improved catalyst activity and/or improved catalyst selectivity and produce propylene-based olefins with broad molecular weight distribution.
1. A halogenated amide ester having the structure (I):
wherein R 1 -R 6 are the same or different, each of R 1 -R 6 is selected from a group consisting of hydrogen, a halogen, and an acyclic alkyl group having 1-20 carbon atoms, and at least one of R 1 -R 6 is an acyclic alkyl group; and
Ar 1 and Ar 2 are the same or different and each of Ar 1 and Ar 2 is selected from a group consisting of an aryl group having 6-20 carbon atoms and an arylalkyl group having 7-20 carbon atoms, and at least one of Ar 1 and Ar 2 is halogenated.
2. The halogenated amide ester of claim 1 , wherein each of Ar 1 and Ar 2 is selected from the group consisting of a phenyl group, a naphthyl group, an anthracenyl group, and a phenanthrenyl group.
3. The halogenated amide ester of claim 1 , wherein at least two of R 1 -R 6 are an acyclic alkyl group having 1-6 carbon atoms.
4. The halogenated amide ester of claim 1 having the structure (II)
wherein R 11 -R 13 and R 21 -R 23 are hydrogen, and at least one of R 11 -R 13 and at least one of R 21 -R 23 is a halogen.
5. The halogenated amide ester of claim 4 , wherein each of R 12 and R 22 is selected from the group consisting of chlorine and fluorine.
6. The halogenated amide ester of claim 1 , wherein each of R 1 and R 2 is a hydrocarbyl group having 1 to 6 carbon atoms.
7. The halogenated amide ester of claim 1 , wherein each of R 3 and R 5 is a hydrocarbyl group having 1 to 6 carbon atoms.
8. A procatalyst composition comprising:
a combination of a magnesium moiety, a titanium moiety and an internal electron donor comprising a halogenated amide ester of structure (I):
wherein R 1 -R 6 are the same or different, each of R 1 -R 6 is selected from a group consisting of hydrogen, a halogen, a hydrocarbyl group having 1-20 carbon atoms, and a substituted hydrocarbyl group having 1-20 carbon atoms; and
Ar 1 and Ar 2 are the same or different and each of Ar 1 and Ar 2 is selected from a group consisting of an aryl group having 6-20 carbon atoms and an arylalkyl group having 7-20 carbon atoms, and at least one of Ar 1 and Ar 2 is halogenated.
9. The procatalyst composition of claim 8 comprising a benzoate.
10. A catalyst composition comprising;
a procatalyst composition of claim 8 ; and
a cocatalyst.
11. The catalyst composition of claim 10 comprising an external electron donor selected from the group consisting of a silicon compound, a bidentate compound, a diether, a diol ester, a carboxylate, an amine, a phosphite, and combinations thereof.
12. The catalyst composition of claim 10 comprising an activity limiting agent selected from the group consisting of a carboxylic acid ester, a diether, a diol ester, and combinations thereof.
13. A process for producing an olefin-based polymer comprising:
contacting, under polymerization conditions, an olefin with a catalyst composition comprising a halogenated amide ester of structure (I):
wherein R 1 -R 6 are the same or different, each of R 1 -R 6 is selected from a group consisting of hydrogen, a halogen, a hydrocarbyl group having 1-20 carbon atoms, and a substituted hydrocarbyl group having 1-20 carbon atoms; and
Ar 1 and Ar 2 are the same or different and each of Ar 1 and Ar 2 is selected from a group consisting of an aryl group having 6-20 carbon atoms and an arylalkyl group having 7-20 carbon atoms, and at least one of Ar 1 and Ar 2 is halogenate; and
forming an olefin-based polymer comprising the halogenated amide ester.
14. The process of claim 13 wherein the olefin is propylene and the process comprises forming a propylene-based polymer having a polydispersity index of from about 5.0 to about 20.0.