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Containing Nitrogen and Phosphorus Porous Organic Polymer-Supported Rhodium Catalyst for Hydroformylation of Olefins

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Abstract

Hydroformylation of olefins with CO and H2 is an attractive approach to synthesize value-added aldehydes. Numerous efforts have been dedicated to the development of novel and efficient catalyst systems, given the high demand for aldehydes. By immobilizing complexes on the surface of heteroatom-containing porous organic polymers have garnered renewed attention. In this paper, a series of porous organic polymer-supported rhodium catalysts were prepared, of which the results demonstrated that the Rh/PTBA-TTA catalyst with abundant nitrogen and phosphorus exhibited excellent activity (100% conversion) and high linear aldehyde selectivity (74%) for the heterogeneous catalytic hydroformylation reaction of 1-octene. The investigations of catalyst dosage, reaction temperature and partial pressure ratio were conducted. In addition, Rh/PTBA-TTA catalyst displayed broad substrate scope and recyclability. The structures of the catalysts were thoroughly characterized by mean of a spectrum of characterization techniques including FT-IR, XPS, solid-state MAS NMR, SEM and TEM. The data indicate that the presence of highly dispersed Rh active species might be on the Rh/PTBA-TTA catalyst. Moreover, the hot filtration test further confirmed the heterogeneity of the reaction, exhibiting great potential for the industrial applications.

Graphical Abstract

A series of nitrogen and phosphorus-containing porous organic polymer-supported Rh catalysts are demonstrated to be highly effective in the hydroformylation of various olefins.

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References

  1. Franke R, Selent D, Borner A (2012) Applied hydroformylation. Chem Rev 112:5675–5732. https://doi.org/10.1021/cr3001803

    Article  PubMed  CAS  Google Scholar 

  2. Cornils B, Herrmann WA, Rasch M (1994) Otto Roelen, pioneer in industrial homogeneous catalysis. Angew Chem Int Ed Engl 33:2144–2163. https://doi.org/10.1002/anie.199421441

    Article  Google Scholar 

  3. Bates RW, Kasinathan S (2013) Hydroformylation in natural product synthesis. Top Curr Chem 342:187–223. https://doi.org/10.1007/128_2013_428

    Article  PubMed  CAS  Google Scholar 

  4. Gorbunov DN, Volkov AV, Kardasheva YS, Maksimov AL, Karakhanov EA (2015) Hydroformylation in petroleum chemistry and organic synthesis: implementation of the process and solving the problem of recycling homogeneous catalysts (Review). Pet Chem 55:587–603. https://doi.org/10.1134/s0965544115080046

    Article  CAS  Google Scholar 

  5. Fleischer I, Dyballa KM, Jennerjahn R, Jackstell R, Franke R, Spannenberg A, Beller M (2013) From olefins to alcohols: efficient and regioselective ruthenium-catalyzed domino hydroformylation/reduction sequence. Angew Chem Int Ed Engl 52:2949–2953. https://doi.org/10.1002/anie.201207133

    Article  PubMed  CAS  Google Scholar 

  6. Dydio P, Detz RJ, de Bruin B, Reek JN (2014) Beyond classical reactivity patterns: hydroformylation of vinyl and allyl arenes to valuable beta- and gamma-aldehyde intermediates using supramolecular catalysis. J Am Chem Soc 136:8418–8429. https://doi.org/10.1021/ja503033q

    Article  PubMed  CAS  Google Scholar 

  7. Takahashi K, Yamashita M, Nozaki K (2012) Tandem hydroformylation/hydrogenation of alkenes to normal alcohols using Rh/Ru dual catalyst or Ru single component catalyst. J Am Chem Soc 134:18746–18757. https://doi.org/10.1021/ja307998h

    Article  PubMed  CAS  Google Scholar 

  8. Dydio P, Dzik WI, Lutz M, de Bruin B, Reek JN (2011) Remote supramolecular control of catalyst selectivity in the hydroformylation of alkenes. Angew Chem Int Ed Engl 50:396–400. https://doi.org/10.1002/anie.201005173

    Article  PubMed  CAS  Google Scholar 

  9. Vilches-Herrera M, Domke L, Börner A (2014) Isomerization–hydroformylation tandem reactions. ACS Catal 4:1706–1724. https://doi.org/10.1021/cs500273d

    Article  CAS  Google Scholar 

  10. Iu L, Fuentes JA, Janka ME, Fontenot KJ, Clarke ML (2019) High iso aldehyde selectivity in the hydroformylation of short-chain alkenes. Angew Chem Int Ed Engl 58:2120–2124. https://doi.org/10.1002/anie.201811888

    Article  PubMed  CAS  Google Scholar 

  11. Liu W, Yuan M, Fu H, Li R, Chen H (2009) Progress of rhodium/diphosphine-catalyzed homogeneous hydroformylation of internal olefins. Chin J Catal 30:577–586. https://doi.org/10.1021/ja050148o

    Article  CAS  Google Scholar 

  12. Klosin J, Landis CR (2007) Ligands for practical rhodium-catalyzed asymmetric hydroformylation. Acc Chem Res 40:1251–1259. https://doi.org/10.1021/ar7001039

    Article  PubMed  CAS  Google Scholar 

  13. Clark TP, Landis CR, Freed SL, Klosin J, Abboud KA (2005) Highly active, regioselective, and enantioselective hydroformylation with Rh catalysts ligated by bis-3,4-diazaphospholanes. J Am Chem Soc 127:5040–5042. https://doi.org/10.1021/ja050148o

    Article  PubMed  CAS  Google Scholar 

  14. Beller M, Cornils B, Frohning CD, Kohlpaintner CW (1995) Progress in hydroformylation and carbonylation. J Mol Catal A Chem 104:17–85. https://doi.org/10.1016/1381-1169(95)00130-1

    Article  CAS  Google Scholar 

  15. Casey CP, Whiteker GT, Melville MG, Petrovich LM, Gavney JA Jr, Powell DR (1992) Diphosphines with natural bite angles near 120.degree. increase selectivity for n-aldehyde formation in rhodium-catalyzed hydroformylation. J Am Chem Soc 114:5535–5543. https://doi.org/10.1021/ja00040a008

    Article  CAS  Google Scholar 

  16. Kranenburg M, van der Burgt YEM, Kamer PCJ, van Leeuwen PWNM, Goubitz K, Fraanje J (1995) New diphosphine ligands based on heterocyclic aromatics inducing very high regioselectivity in rhodium-catalyzed hydroformylation: effect of the bite angle. Organometallics 14:3081–3089. https://doi.org/10.1021/om00006a057

    Article  CAS  Google Scholar 

  17. Klein H, Jackstell R, Wiese K-D, Borgmann C, Beller M (2001) Highly selective catalyst systems for the hydroformylation of internal olefins to linear aldehydes. Angew Chem Int Ed 40:3408–3411. https://doi.org/10.1002/1521-3773(20010917)40:18%3c3408::AID-ANIE3408%3e3.0.CO;2-A

    Article  CAS  Google Scholar 

  18. Neto DHC, Dos Santos AAM, Da Silva JCS, Rocha WR, Dias RP (2020) Propene hydroformylation reaction catalyzed by HRh(CO)(BISBI): a thermodynamic and kinetic analysis of the full catalytic cycle. Eur J Inorg Chem 2020:3907–3916. https://doi.org/10.1002/ejic.202000799

    Article  CAS  Google Scholar 

  19. Behr A, Obst D, Schulte C, Schosser T (2003) Highly selective tandem isomerization–hydroformylation reaction of trans-4-octene to n-nonanal with rhodium-BIPHEPHOS catalysis. J Mol Catal A Chem 206:179–184. https://doi.org/10.1016/S1381-1169(03)00461-8

    Article  CAS  Google Scholar 

  20. Vogl C, Paetzold E, Fischer C, Kragl U (2005) Highly selective hydroformylation of internal and terminal olefins to terminal aldehydes using a rhodium-BIPHEPHOS-catalyst system. J Mol Catal A Chem 232:41–44. https://doi.org/10.1016/j.molcata.2005.01.019

    Article  CAS  Google Scholar 

  21. van der Veen LA, Kamer PCJ, van Leeuwen PWNM (1999) Hydroformylation of internal olefins to linear aldehydes with novel rhodium catalysts. Angew Chem Int Ed 38:336–338. https://doi.org/10.1002/(SICI)1521-3773(19990201)38:3%3c336::AID-ANIE336%3e3.0.CO;2-P

    Article  Google Scholar 

  22. Zuidema E, Escorihuela L, Eichelsheim T, Carbó JJ, Bo C, Kamer PCJ, van Leeuwen PWNM (2008) The rate-determining step in the rhodium–xantphos-catalysed hydroformylation of 1-octene. Chem Eur J 14:1843–1853. https://doi.org/10.1002/chem.200700727

    Article  PubMed  CAS  Google Scholar 

  23. Kumar M, Chaudhari RV, Subramaniam B, Jackson TA (2015) Importance of long-range noncovalent interactions in the regioselectivity of rhodium-xantphos-catalyzed hydroformylation. Organometallics 34:1062–1073. https://doi.org/10.1021/om5012775

    Article  CAS  Google Scholar 

  24. Eckl RW, Priermeier T, Herrmann WA (1997) Mono- and biphasic asymmetric hydroformylation with rhodium catalysts of the diphosphine ligand NAPHOS and its sulfonated derivatives. J Organomet Chem 532:243–249. https://doi.org/10.1016/S0022-328X(96)06745-9

    Article  CAS  Google Scholar 

  25. Rodrigues FMS, Carrilho RMB, Pereira MM (2021) Reusable catalysts for hydroformylation-based reactions. Eur J Inorg Chem 2021:2294–2324. https://doi.org/10.1002/ejic.202100032

    Article  CAS  Google Scholar 

  26. Zhao K, Wang X, He D, Wang H, Qian B, Shi F (2022) Recent development towards alkene hydroformylation catalysts integrating traditional homo- and heterogeneous catalysis. Catal Sci Technol 12:4962–4982. https://doi.org/10.1039/D2CY00845A

    Article  CAS  Google Scholar 

  27. Shi Y, Lu Y, Ren T, Li J, Hu Q, Hu X, Zhu B, Huang W (2020) Rh particles supported on sulfated g-C3N4: a highly efficient and recyclable heterogeneous catalyst for alkene hydroformylation. Catalysts 10:1359. https://doi.org/10.3390/catal10111359

    Article  CAS  Google Scholar 

  28. Alini S, Bottino A, Capannelli G, Comite A, Paganelli S (2005) Preparation and characterisation of Rh/Al2O3 catalysts and their application in the adiponitrile partial hydrogenation and styrene hydroformylation. Appl Catal A Gen 292:105–112. https://doi.org/10.1016/j.apcata.2005.05.048

    Article  CAS  Google Scholar 

  29. Tan M, Yang G, Wang T, Vitidsant T, Li J, Wei Q, Ai P, Wu M, Zheng J, Tsubaki N (2016) Active and regioselective rhodium catalyst supported on reduced graphene oxide for 1-hexene hydroformylation. Catal Sci Technol 6:1162–1172. https://doi.org/10.1039/C5CY01355K

    Article  CAS  Google Scholar 

  30. Li J, Mao A, Yao W, Zhu H, Wang D (2022) Iridium supported on porous polypyridine-oxadiazole as high-activity and recyclable catalyst for the borrowing hydrogen reaction. Green Chem 24:2602–2612. https://doi.org/10.1039/D2GC00190J

    Article  CAS  Google Scholar 

  31. Li J, Zeng W, Wang L, Shi G, Wang D (2023) Pyrazolyl-pyrimidine porous-organic-polymer supported single-site nickel composites as efficient catalysts for the synthesis of substituted pyrimidines. Chem Eng J 474:145642. https://doi.org/10.1016/j.cej.2023.145642

    Article  CAS  Google Scholar 

  32. Zhang Y, Riduan SN (2012) Functional porous organic polymers for heterogeneous catalysis. Chem Soc Rev 41:2083–2094. https://doi.org/10.1039/C1CS15227K

    Article  PubMed  CAS  Google Scholar 

  33. Kramer S, Bennedsen NR, Kegnæs S (2018) Porous organic polymers containing active metal centers as catalysts for synthetic organic chemistry. ACS Catal 8:6961–6982. https://doi.org/10.1021/acscatal.8b01167

    Article  CAS  Google Scholar 

  34. Jia X, Liang Z, Chen J, Lv J, Zhang K, Gao M, Zong L, Xie C (2019) Porous organic polymer supported rhodium as a reusable heterogeneous catalyst for hydroformylation of olefins. Org Lett 21:2147–2150. https://doi.org/10.1021/acs.orglett.9b00459

    Article  PubMed  CAS  Google Scholar 

  35. Liang Z, Chen J, Chen X, Zhang K, Lv J, Zhao H, Zhang G, Xie C, Zong L, Jia X (2019) Porous organic polymer supported rhodium as a heterogeneous catalyst for hydroformylation of alkynes to α,β-unsaturated aldehydes. Chem Commun 55:13721–13724. https://doi.org/10.1039/C9CC06834A

    Article  CAS  Google Scholar 

  36. Sun Q, Dai Z, Liu X, Sheng N, Deng F, Meng X, Xiao F-S (2015) Highly efficient heterogeneous hydroformylation over Rh-metalated porous organic polymers: synergistic effect of high ligand concentration and flexible framework. J Am Chem Soc 137:5204–5209. https://doi.org/10.1021/jacs.5b02122

    Article  PubMed  CAS  Google Scholar 

  37. Ji G, Li C, Xiao D, Wang G, Sun Z, Jiang M, Hou G, Yan L, Ding Y (2021) The effect of the position of cross-linkers on the structure and microenvironment of PPh3 moiety in porous organic polymers. J Mater Chem A 9:9165–9174. https://doi.org/10.1039/D0TA12316A

    Article  CAS  Google Scholar 

  38. Wang Y, Jiang M, Yan L, Li C, Wang G, He W, Ding Y (2023) Influence of phosphite ligands concentration on 1-butene hydroformylation over Rh-supported porous organic polymer catalysts. Mol Catal 539:113015. https://doi.org/10.1016/j.mcat.2023.113015

    Article  CAS  Google Scholar 

  39. Wang W, Li C, Yan L, Wang Y, Jiang M, Ding Y (2016) Ionic liquid/Zn-PPh3 integrated porous organic polymers featuring multifunctional sites: highly active heterogeneous catalyst for cooperative conversion of CO2 to cyclic carbonates. ACS Catal 6:6091–6100. https://doi.org/10.1021/acscatal.6b01142

    Article  CAS  Google Scholar 

  40. Li C, Wang W, Yan L, Wang Y, Jiang M, Ding Y (2016) Phosphonium salt and ZnX2–PPh3 integrated hierarchical POPs: tailorable synthesis and highly efficient cooperative catalysis in CO2 utilization. J Mater Chem A 4:16017–16027. https://doi.org/10.1039/C6TA05823J

    Article  CAS  Google Scholar 

  41. Chen X, Zhu H, Song X, Du H, Wang T, Zhao Z, Ding Y (2017) Ru–PPh3@porous organic polymer: efficient and stable catalyst for the trickle bed regioselective hydrogenation of cinnamaldehyde. React Kinet Mech Catal 120:637–649. https://doi.org/10.1007/s11144-016-1130-6

    Article  CAS  Google Scholar 

  42. Chen M, Mou X, Wang S, Chen X, Tan Y, Chen M, Zhao Z, Huang C, Yang W, Lin R, Ding Y (2020) Porous organic polymer-supported palladium catalyst for hydroesterification of olefins. Mol Catal 498:111239. https://doi.org/10.1016/j.mcat.2020.111239

    Article  CAS  Google Scholar 

  43. Ding ZC, Li CY, Chen JJ, Zeng JH, Tang HT, Ding YJ, Zhan ZP (2017) Palladium/phosphorus-doped porous organic polymer as recyclable chemoselective and efficient hydrogenation catalyst under ambient conditions. Adv Synth Catal 359:2280–2287. https://doi.org/10.1002/adsc.201700374

    Article  CAS  Google Scholar 

  44. Jiang W, Li J, Wu M, He L, Zhou G, Wang Z (2023) Preparation of porous organic polymers containing N or P atoms and their application in hydroformylation of 1-octene. Fuel 338:127291. https://doi.org/10.1016/j.fuel.2022.127291

    Article  CAS  Google Scholar 

  45. Ji G, Li C, Gao P, Jiang M, Ma L, Wang G, Hou G, Yan L, Ding Y (2023) Tuning the framework flexibility and equilibrium of HRh(CO)2P2 active isomers in single-atom Rh/P&N-POPs catalysts for hydroformylation reactions. Chem Eng J 470:144334. https://doi.org/10.1016/j.cej.2023.144334

    Article  CAS  Google Scholar 

  46. Yang Z, Yu B, Zhang H, Zhao Y, Chen Y, Ma Z, Ji G, Gao X, Han B, Liu Z (2016) Metalated mesoporous poly(triphenylphosphine) with azo functionality: efficient catalysts for CO2 conversion. ACS Catal 6:1268–1273. https://doi.org/10.1021/acscatal.5b02583

    Article  CAS  Google Scholar 

  47. Yang Y, Wang T, Jing X, Zhu G (2019) Phosphine-based porous aromatic frameworks for gold nanoparticle immobilization with superior catalytic activities. J Mater Chem A 7:10004–10009. https://doi.org/10.1039/C8TA12099D

    Article  CAS  Google Scholar 

  48. Deng G, Wang Z (2018) Hierarchical porous phenolic resin and its supported Pd-catalyst for Suzuki-Miyaura reactions in water medium. Macromol Rapid Commun 39:1700618. https://doi.org/10.1002/marc.201700618

    Article  CAS  Google Scholar 

  49. Zhao K, Wang H, Wang X, Li T, Dai X, Zhang L, Cui X, Shi F (2021) Confinement of atomically dispersed Rh catalysts within porous monophosphine polymers for regioselective hydroformylation of alkenes. J Catal 401:321–330. https://doi.org/10.1016/j.jcat.2021.08.004

    Article  CAS  Google Scholar 

  50. Tao R, Shen X, Hu Y, Kang K, Zheng Y, Luo S, Yang S, Li W, Lu S, Jin Y, Qiu L, Zhang W (2020) Phosphine-based covalent organic framework for the controlled synthesis of broad-scope ultrafine nanoparticles. Small 16:1906005. https://doi.org/10.1002/smll.201906005

    Article  CAS  Google Scholar 

  51. Pandey P, Katsoulidis AP, Eryazici I, Wu Y, Kanatzidis MG, Nguyen ST (2010) Imine-linked microporous polymer organic frameworks. Chem Mater 22:4974–4979. https://doi.org/10.1021/cm101157w

    Article  CAS  Google Scholar 

  52. Wang Y, Yan L, Li C, Jiang M, Wang W, Ding Y (2018) Highly efficient porous organic copolymer supported Rh catalysts for heterogeneous hydroformylation of butenes. Appl Catal A Gen 551:98–105. https://doi.org/10.1016/j.apcata.2017.12.013

    Article  CAS  Google Scholar 

  53. Yang X, Du Y-R, Guan P-X, Liu H-Y, Wang Y-F, Xu B-H (2022) The one-pot encapsulation of palladium complexes into covalent organic frameworks enables the alkoxycarbonylation of olefins. ChemCatChem 14:e202101594. https://doi.org/10.1002/cctc.202101594

    Article  CAS  Google Scholar 

  54. Wang J, Yu Y, Xu W, Yu H, Zhang W, Huang H, Zhang G-R, Mei D (2022) Covalent triazine framework encapsulated Pd nanoclusters for efficient hydrogen production via ammonia borane hydrolysis. J Catal 411:72–83. https://doi.org/10.1016/j.jcat.2022.05.009

    Article  CAS  Google Scholar 

  55. Jurado L, Esvan J, Luque-Álvarez LA, Bobadilla LF, Odriozola JA, Posada-Pérez S, Poater A, Comas-Vives A, Axet MR (2023) Highly dispersed Rh single atoms over graphitic carbon nitride as a robust catalyst for the hydroformylation reaction. Catal Sci Technol 13:1425–1436. https://doi.org/10.1039/D2CY02094G

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  56. Jin F, Liu Q, Quan Z, Kang M, Wang X, Song H (2022) Phosphorus-containing polymeric ionic liquids-supported rhodium catalyst for hydroformylation of dihydrofurans. Mol Catal 521:112207. https://doi.org/10.1016/j.mcat.2022.112207

    Article  CAS  Google Scholar 

  57. Liu B, Wang Y, Huang N, Lan X, Xie Z, Chen JG, Wang T (2022) Heterogeneous hydroformylation of alkenes by Rh-based catalysts. Chem 8:2630–2658. https://doi.org/10.1016/j.chempr.2022.07.020

    Article  CAS  Google Scholar 

  58. Li T, Chen F, Lang R, Wang H, Su Y, Qiao B, Wang A, Zhang T (2020) Styrene hydroformylation with in situ hydrogen: regioselectivity control by coupling with the low-temperature water–gas shift reaction. Angew Chem Int Ed 59:7430–7434. https://doi.org/10.1002/anie.202000998

    Article  CAS  Google Scholar 

  59. Wei R, Ju S, Liu LL (2022) Free metallophosphines: extremely electron-rich phosphorus superbases that are electronically and sterically tunable. Angew Chem Int Ed 61:e202205618. https://doi.org/10.1002/anie.202205618

    Article  CAS  Google Scholar 

  60. Li C, Sun K, Wang W, Yan L, Sun X, Wang Y, Xiong K, Zhan Z, Jiang Z, Ding Y (2017) Xantphos doped Rh/POPs-PPh3 catalyst for highly selective long-chain olefins hydroformylation: chemical and DFT insights into Rh location and the roles of Xantphos and PPh3. J Catal 353:123–132. https://doi.org/10.1016/j.jcat.2017.07.022

    Article  CAS  Google Scholar 

  61. Wang W, Li C, Zhang H, Zhang J, Lu L, Jiang Z, Cui L, Liu H, Yan L, Ding Y (2021) Enhancing the activity, selectivity, and recyclability of Rh/PPh3 system-catalyzed hydroformylation reactions through the development of a PPh3-derived quasi-porous organic cage as a ligand. Chin J Catal 42:1216–1226. https://doi.org/10.1016/S1872-2067(20)63746-9

    Article  CAS  Google Scholar 

  62. Zeng G, Liang K, Huang Y, Liu C, Chen H, Wang D, Ma J, Dong Z (2023) Rh nanoparticles anchored on phosphorous-doped porous carbon for efficiently catalytic hydroformylation of alkenes. Mol Catal 550:113548. https://doi.org/10.1016/j.mcat.2023.113548

    Article  CAS  Google Scholar 

  63. Sun Y, Harloff J, Kosslick H, Schulz A, Fischer C, Bartling S, Frank M, Springer A (2022) Influence of the framework on the catalytic performance of Rh-supported Zr-MOFs in the hydroformylation of n-alkenes. Mol Catal 517:112005. https://doi.org/10.1016/j.mcat.2021.112005

    Article  CAS  Google Scholar 

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Acknowledgements

The authors gratefully acknowledge financial support from National Natural Science Foundation of China (22072166, 21673260) and Key Program of the Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences (No. KJZLZD-2).

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  1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, People’s Republic of China

    Yongcheng Lan, Dong Yun, Chungu Xia, Bo Qian & Jianhua Liu

  2. University of Chinese Academy of Sciences, Beijing, 100049, People’s Republic of China

    Yongcheng Lan, Chungu Xia, Bo Qian & Jianhua Liu

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Lan, Y., Yun, D., Xia, C. et al. Containing Nitrogen and Phosphorus Porous Organic Polymer-Supported Rhodium Catalyst for Hydroformylation of Olefins. Catal Lett (2024). https://doi.org/10.1007/s10562-024-04602-4

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