A Novel Strategy of Homogeneous Catalysis and Highly Efficient Recycling of Aqueous Catalyst for the Hydroformylation of
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A Novel Strategy of Homogeneous Catalysis and Highly Efficient Recycling of Aqueous Catalyst for the Hydroformylation of Higher Olefins Based on a Simple Methanol/Water Mixed Solvent Jiangui Zhao1 · Jiwei Yi1 · Chunji Yang2 · Kefeng Wan1 · Xiaoxia Duan1 · Songbai Tang1 · Haiyan Fu1 · Xueli Zheng1 · Maolin Yuan1 · Ruixiang Li1 · Hua Chen1 Received: 10 July 2020 / Accepted: 3 September 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract This paper describes the homogeneous catalysis and highly efficient recycling of aqueous catalyst for the hydroformylation of higher olefins in the methanol/water mixed solvent for the first time. When sufficient methanol is added into aqueous HRh(CO)(TPPTS)3/TPPTS solution and 1-hexene, the reaction mixture becomes a single phase at reaction temperature (TPPTS: Trisodium triphenylphosphine-3,3′,3″-trisulfonate), which makes the 1-hexene hydroformylation proceed homogeneously. The turnover number (TON) is 11880 during an hour, and TON is up to 10428 during half an hour at a substrate to catalyst ratio of 12000. After the reaction, the methanol with low boiling point can be readily recovered by distilling the product mixture at the reaction temperature. And then, what’s left is the aqueous organic two-phase mixture. The aqueous catalyst solution can be separated from the products by a simple decantation. The recovered aqueous catalyst solution as well as methanol can be recycled for seven runs without significant loss of activity and selectivity for aldehydes. Moreover, the average rhodium leaching in products is less than 0.09 wt%.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10562-020-03385-8) contains supplementary material, which is available to authorized users. * Xueli Zheng [email protected]
Songbai Tang [email protected]
* Maolin Yuan [email protected]
Haiyan Fu [email protected]
Jiangui Zhao [email protected]
Ruixiang Li [email protected]
Jiwei Yi [email protected]
Hua Chen [email protected]
Chunji Yang [email protected]
1
Key Lab of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China
2
Petrochemical Research Institute Daqing Petrochemical Research Center, Daqing 163000, China
Kefeng Wan [email protected] Xiaoxia Duan [email protected]
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Graphic Abstract
Keywords Hydroformylation · Higher olefin · Water soluble phosphine · Rhodium · Water · Methanol
1 Introduction As is well known, high carbon aldehydes, as an important class of organic compounds and synthetical intermediates, are widely used in the synthesis of plasticizers, surfactants, pharmaceuticals, detergents and fine chemicals, and have great commercial value [1–7]. At present, high carbon aldehydes are produced by the hydroformylation of higher olefin (an example in Scheme 1). Although Rh-catalyzed homogeneous hydroformylation has the advantages of high activity and selectivity for
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