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New Catalyst Development for the Production of Linear Alpha-Olefins

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Presentation on theme: "New Catalyst Development for the Production of Linear Alpha-Olefins"— Presentation transcript:

1 New Catalyst Development for the Production of Linear Alpha-Olefins
Acknowledgments SPE/FlexPack organizers CPChem Prof. Mike Carney (U. Wisconsin – Eau Claire), Prof. Jason Halfen, Ben Schmiege, Deidra Gerlach, Tony Buerger Technicians Ray Rios, Eric Fernandez 29 February 2012 Brooke L. Small Senior Research Chemist Chevron Phillips Chemical Company LP Kingwood, TX

2 Entry Barriers to Commercial Alpha-Olefin Production
Demand for various AO fractions Captive requirements of AO producers Feedstock cost and availability Development of new end uses Product quality requirements Catalyst limitations Sell everything Use what you don’t sell Build it in the right place Work with customers Meet or exceed market requirements Understand the chemistry

3 Projected Growth Rates and Typical Product Distributions
Growth rates for comonomer (C4 - C8) higher than other olefins Smaller full range producers such as Sabic, Idemitsu Selective and non-ethylene based processes not shown Distribution flexibility tied to distillation CPChem, Shell governed by K value (K = mol Cn+2/mol Cn) Source: Lappin, Alpha Olefins Applications Handbook, 1989.

4 Catalyst Limitations Process design must consider specific traits of each catalyst system Catalyst distribution must be tailored to business need Intrinsic catalyst limitations must be considered (e.g. Ni isomerization, Zr PE formation, etc.)

5 Selective Alpha-Olefin Production – Another Alternative to Supply/Demand Balancing
1-Butene Axens (IFP) Alphabutol® process ~30 plants worldwide 700 kmt/yr of 1-butene Ti catalyst used to dimerize ethylene Primarily used in remote locations Raffinate distillation ExxonMobil and Texas Petrochemicals 450 million lbs/yr Much of the growth in the C4 comonomer demand can be met by selective production.

6 Selective Alpha-Olefin Production – 1-Hexene and 1-Octene
Cr-pyrrole system for ethylene trimerization CPChem first to commercialize this system (see, e.g., US 5,198,563; 7,384,886) Daqing and Mitsui also have announced commercial intentions Sasol 1-hexene and 1-octene via Fischer-Tropsch extraction 1-octene via hydroformylation/dehydration of 1-heptene 1/hexene/1-octene plant announced (ethylene tetramerization) Dow produces 1-octene from butadiene (Pd catalyst)

7 Catalysts for 1-Hexene and 1-Octene

8 Full Range Commercial Catalysts
1966 – Gulf  Chevron  CPChem alpha-olefin process 1970 – Ethyl  Albemarle  Amoco  BP  Ineos AO process Both processes based on triethylaluminum, TEA CPChem distribution is Schulz-Flory; Ineos distribution is stoichiometric (i.e. no chain termination) 1983 –Shell Higher Olefins Process (SHOP) 1989 – Idemitsu ZrCl4 based system with Al-alkyl cocatalyst SABIC also uses Zr

9 Pendant Donor Modified a-Diimine Complexes
Develop a hybrid between the A and B Create a favorable steric environment Develop a fairly rigid backbone Create new IP for alpha-olefin production Product distribution flexibility Lower pressure process than triethylaluminum (TEA)

10 Structural “Knobs” Four “handles” on the pre-catalyst complexes offer remarkable diversity of structures.

11 Structural Diversification

12 Catalyst Studies Steric changes on N-aryl affect distribution
Steric changes on P affect distribution and activity NNS complexes tend toward higher K values Modular approach provides significant “K-tunability” Extraordinary product quality (> 99% 1-octene in C8 fraction)

13 A Practical Consideration of K Tunability

14 Conclusions Commercialization of alpha-olefin technology presents significant entry barriers NNP and NNS Fe systems provide an attractive full range catalyst opportunity: K tunability Outstanding product purity Easily accessible portfolio of complexes Our publications B. L. Small,* R. Rios, E. R. Fernandez, M. J. Carney  Organometallics 2007, 26, 1744. B. L. Small,* R. Rios, E. R. Fernandez, D. L. Gerlach, J. A. Halfen, M. J. Carney  Organometallics 2010, 29, 6723. B. M. Schmiege, M. J. Carney,* B. L. Small, D. L. Gerlach, J. A. Halfen, Dalton Trans. 2007, 2547. US Patents 7,977,269; 7,728,161; 7,728,160; 7,727,926; 7,271,121; 7,268,096; 7,129,304

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