Coupling reaction between CO2 and cyclohexene oxide: selective control from cyclic carbonate to polycarbonate by ligand design of salen/salalen titanium complexes

Yong Wang; Yusheng Qin; Xianhong Wang; Fosong Wang

doi:10.1039/C4CY00752B

Coupling reaction between CO₂ and cyclohexene oxide: selective control from cyclic carbonate to polycarbonate by ligand design of salen/salalen titanium complexes†

Yong Wang,^ab Yusheng Qin,*^a Xianhong Wang*^a and Fosong Wang^a

* Corresponding authors

^a Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, People's Republic of China
E-mail: ysqin@ciac.jl.cn, xhwang@ciac.jl.cn
Fax: +86 0431 85262252
Tel: +86 0431 85262252

^b University of Chinese Academy of Sciences, Beijing 100039, People's Republic of China

Abstract

Based on the mechanistic features of metal salen catalysis systems, titanium(IV) complexes from salen (salen-H₂ = N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-benzenediamine) and its half saturated form salalen have been prepared, which were used as catalysts in conjugation with bis(triphenylphosphino)iminium chloride ([PPN]Cl) for the coupling reaction of CO₂ and cyclohexene oxide (CHO). The salen titanium complex (salen)Ti(IV)Cl₂ showed moderate activity, producing a unique cis-isomer of cyclic carbonate with high conversion up to 100% in 8 h, however, it could not catalyze the copolymerization reaction. Meanwhile, the salalen titanium complex (salalen)Ti(IV)Cl was effective for the copolymerization of CO₂ and CHO, where only one chain grew on Ti during the chain propagation reaction, yielding completely alternating copolymers with –OH and –Cl as terminal groups. Moreover, the nearly complete conversion of CHO indicated that (salalen)Ti(IV)Cl might be used to synthesize multiblock poly(cyclohexene carbonate)s with controllable sequences.

Supplementary files

Article information

DOI: https://doi.org/10.1039/C4CY00752B
Article type: Paper
Submitted: 08 Jun 2014
Accepted: 03 Jul 2014
First published: 03 Jul 2014

Download Citation

Catal. Sci. Technol., 2014,4, 3964-3972

Author version available

Download author version (PDF)

Permissions

Request permissions

Coupling reaction between CO₂ and cyclohexene oxide: selective control from cyclic carbonate to polycarbonate by ligand design of salen/salalen titanium complexes

Y. Wang, Y. Qin, X. Wang and F. Wang, Catal. Sci. Technol., 2014, 4, 3964 DOI: 10.1039/C4CY00752B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Catalysis Science & Technology