Catalytic hydrogenation of levulinic acid in aqueous phase

Clara Delhomme; Lars Arne Schaper; Mei Zhang-Preße; Gabriele Raudaschl-Sieber; Dirk Weuster-Botz; Fritz E. Kühn

doi:10.1016/j.jorganchem.2012.10.030

Catalytic hydrogenation of levulinic acid in aqueous phase

Clara Delhomme
, Lars Arne Schaper
, Mei Zhang-Preße
, Gabriele Raudaschl-Sieber
, Dirk Weuster-Botz
, Fritz E. Kühn

Technical University of Munich

Research output: Contribution to journal › Article › peer-review

80 Scopus citations

Abstract

The hydrogenation of levulinic acid (LA) yielding γ-valerolactone (GVL) has been examined in aqueous solution using various water soluble phosphine ligands in combination with the metal precursors [Ru(acac) ₃] and [RuCl₃]. Using catalyst loadings of only 0.2 mol%, GVL could be obtained in yields up to 99% conversion and 97% selectivity along with a maximum turnover frequency of 200mol_GVLmol_Ru- 1h^-1 within 5 h, using 3,3′,3′′- phosphinidynetris(benzenesulfonic acid) trisodium salt (TPPTS) and Ru(acac) ₃ as catalytic system. In addition, a ruthenium-phosphine complex immobilized on the amphiphilic copolymer PS-PEG was examined under the same conditions and gave 90% conversion of LA in 24 h.

Original language	English
Pages (from-to)	297-299
Number of pages	3
Journal	Journal of Organometallic Chemistry
Volume	724
DOIs	https://doi.org/10.1016/j.jorganchem.2012.10.030
State	Published - 15 Jan 2013

Keywords

Aqueous hydrogenation
Levulinic acid
Polymer immobilized complex
Water-soluble phosphines

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10.1016/j.jorganchem.2012.10.030

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@article{82b406acfab441b789d7a7afd03864a3,

title = "Catalytic hydrogenation of levulinic acid in aqueous phase",

abstract = "The hydrogenation of levulinic acid (LA) yielding γ-valerolactone (GVL) has been examined in aqueous solution using various water soluble phosphine ligands in combination with the metal precursors [Ru(acac) 3] and [RuCl3]. Using catalyst loadings of only 0.2 mol\%, GVL could be obtained in yields up to 99\% conversion and 97\% selectivity along with a maximum turnover frequency of 200molGVLmolRu- 1h-1 within 5 h, using 3,3′,3′′- phosphinidynetris(benzenesulfonic acid) trisodium salt (TPPTS) and Ru(acac) 3 as catalytic system. In addition, a ruthenium-phosphine complex immobilized on the amphiphilic copolymer PS-PEG was examined under the same conditions and gave 90\% conversion of LA in 24 h.",

keywords = "Aqueous hydrogenation, Levulinic acid, Polymer immobilized complex, Water-soluble phosphines",

author = "Clara Delhomme and Schaper, \{Lars Arne\} and Mei Zhang-Pre{\ss}e and Gabriele Raudaschl-Sieber and Dirk Weuster-Botz and K{\"u}hn, \{Fritz E.\}",

note = "Funding Information: C.D. is grateful to IGSSE (project 2.07) for a PhD grant and L.A.S. is grateful to TUM Graduate School and the Bavarian Elite Network NanoCat for financial support. ",

year = "2013",

month = jan,

day = "15",

doi = "10.1016/j.jorganchem.2012.10.030",

language = "English",

volume = "724",

pages = "297--299",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - Catalytic hydrogenation of levulinic acid in aqueous phase

AU - Delhomme, Clara

AU - Schaper, Lars Arne

AU - Zhang-Preße, Mei

AU - Raudaschl-Sieber, Gabriele

AU - Weuster-Botz, Dirk

AU - Kühn, Fritz E.

N1 - Funding Information: C.D. is grateful to IGSSE (project 2.07) for a PhD grant and L.A.S. is grateful to TUM Graduate School and the Bavarian Elite Network NanoCat for financial support.

PY - 2013/1/15

Y1 - 2013/1/15

N2 - The hydrogenation of levulinic acid (LA) yielding γ-valerolactone (GVL) has been examined in aqueous solution using various water soluble phosphine ligands in combination with the metal precursors [Ru(acac) 3] and [RuCl3]. Using catalyst loadings of only 0.2 mol%, GVL could be obtained in yields up to 99% conversion and 97% selectivity along with a maximum turnover frequency of 200molGVLmolRu- 1h-1 within 5 h, using 3,3′,3′′- phosphinidynetris(benzenesulfonic acid) trisodium salt (TPPTS) and Ru(acac) 3 as catalytic system. In addition, a ruthenium-phosphine complex immobilized on the amphiphilic copolymer PS-PEG was examined under the same conditions and gave 90% conversion of LA in 24 h.

AB - The hydrogenation of levulinic acid (LA) yielding γ-valerolactone (GVL) has been examined in aqueous solution using various water soluble phosphine ligands in combination with the metal precursors [Ru(acac) 3] and [RuCl3]. Using catalyst loadings of only 0.2 mol%, GVL could be obtained in yields up to 99% conversion and 97% selectivity along with a maximum turnover frequency of 200molGVLmolRu- 1h-1 within 5 h, using 3,3′,3′′- phosphinidynetris(benzenesulfonic acid) trisodium salt (TPPTS) and Ru(acac) 3 as catalytic system. In addition, a ruthenium-phosphine complex immobilized on the amphiphilic copolymer PS-PEG was examined under the same conditions and gave 90% conversion of LA in 24 h.

KW - Aqueous hydrogenation

KW - Levulinic acid

KW - Polymer immobilized complex

KW - Water-soluble phosphines

UR - https://www.scopus.com/pages/publications/84872898248

U2 - 10.1016/j.jorganchem.2012.10.030

DO - 10.1016/j.jorganchem.2012.10.030

M3 - Article

AN - SCOPUS:84872898248

SN - 0022-328X

VL - 724

SP - 297

EP - 299

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

Catalytic hydrogenation of levulinic acid in aqueous phase

Abstract

Keywords

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