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Catalysts 2013, 3(1), 104-124; doi:10.3390/catal3010104

Preparation of Thiophene-Fused and Tetrahydroquinoline-Linked Cyclopentadienyl Titanium Complexes for Ethylene/α-Olefin Copolymerization

Department of Molecular Science and Technology, Ajou University, Suwon 443-749, Korea
Honam Petrochemical Company and Catalyst Research Team 5th, 24-1 Jang-Dong, Yuseong-Gu, Daejeon 305-726, Korea
Department of Chemistry, Chonnam National University, 77 Yongbong-ro, Buk-gu, Gwangju 500-757, Korea
Author to whom correspondence should be addressed.
Received: 17 December 2012 / Revised: 25 January 2013 / Accepted: 29 January 2013 / Published: 6 February 2013
(This article belongs to the Special Issue Molecular Catalysis for Precise Olefin Polymerization)
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A synthetic scheme was developed for the large-scale preparation of a dimethylthiophene-fused and tetrahydroquinaldine-linked dimethylcyclopentadienyl titanium complex (2), which is a high-performance homogeneous Ziegler catalyst. 2,3,4,5-Tetramethyl-4,5-dihydrocyclopenta[b]thiophen-6-one was prepared without chromatography purification on the 40-g scale in a laboratory setting, from which the ligand precursor for 2 was obtained in 65% yield on a 50-g scale in a one-pot without the need for chromatography purification. Metallation was achieved in a high yield (78%) through reaction of the dilithiated compound with TiCl4. Many derivatives were prepared by employing the same synthetic scheme as applied for 2. Among them, the titanium complex prepared from 2-methyl-4,5-dimethyl-6-(2-n-butyl-2,3,4,5-tetrahydroquinolin-8-yl)-4H-cyclopenta[b]thiophene exhibited an exceptionally high activity. Under commercially relevant high-temperature polymerization conditions (160 °C), this compound showed a higher activity than 2 (126 × 106 g/molTi∙h versus 72 × 106 g/molTi∙h), albeit with the formation of a polymer of slightly lower molecular weight (Mw, 159,000 versus 218,000) and with a slightly lower 1-octene content (9.3 mol% versus 12 mol%). View Full-Text
Keywords: titanium complex; half-metallocene; thiophene-fused cyclopentadienyl; ethylene polymerization titanium complex; half-metallocene; thiophene-fused cyclopentadienyl; ethylene polymerization

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Kim, S.H.; Park, J.H.; Song, B.G.; Yoon, S.-W.; Go, M.J.; Lee, J.; Lee, B.Y. Preparation of Thiophene-Fused and Tetrahydroquinoline-Linked Cyclopentadienyl Titanium Complexes for Ethylene/α-Olefin Copolymerization. Catalysts 2013, 3, 104-124.

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