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The Mechanism of Acetal Formation in Acid-Free Rh-Catalyzed Tandem Hydroformylation–Acetalization of Olefins in MeOH

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Abstract

The acetal formation mechanism under acid-free Rh-catalyzed hydroformylation–acetalization condition has been studied using different rhodium catalyst precursors in MeOH. In the absence of added acidic co-catalyst, the acetalization is catalyzed by the H+ formed in situ under hydroformylation condition, and Rh active site on Rh-phosphine catalyst did not exhibit catalytic activity for acetalization. Whether H+ can be generated in situ is related with the structure of rhodium catalyst precursor. Under hydroformylation condition, added Brønsted acids as co-catalysts can improve acetalization efficiency, but the H+ concentration in the system should not be excessively high to avoid the acid-induced inhibition for hydroformylation.

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Acknowledgments

We gratefully thank the financial support from National Natural Science Foundation of China (No. 20606019, 20976086), the Foundation of Key Laboratory of Oil & Gas Fine Chemicals, Ministry of Education, China (No.XJDX0908-2010-01) and the Natural Science Foundation of Qingdao, China (No. 12-1-4-3-(6)-jch).

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Authors and Affiliations

  1. College of Chemical Engineering, Qingdao University of Science and Technology, 53 Zhengzhou Rd, Qingdao, 266042, China

    Xin Jin, Kun Zhao, Fangfang Kong, Feifei Cui, Qiangqiang Liu & Yaowu Zhang

  2. Key Laboratory of Oil & Gas Fine Chemicals of Ministry of Education, Xinjiang University, Wulumuqi, 830046, China

    Xin Jin

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  1. Xin Jin
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  2. Kun Zhao
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  3. Fangfang Kong
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  4. Feifei Cui
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  5. Qiangqiang Liu
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Correspondence to Xin Jin.

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Jin, X., Zhao, K., Kong, F. et al. The Mechanism of Acetal Formation in Acid-Free Rh-Catalyzed Tandem Hydroformylation–Acetalization of Olefins in MeOH. Catal Lett 144, 192–196 (2014). https://doi.org/10.1007/s10562-013-1109-0

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  • DOI: https://doi.org/10.1007/s10562-013-1109-0

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