Homogeneous catalysed hydrogenation of HMF

Alban Cadu; Kohei Sekine; Jaroslaw Mormul; Dominik M. Ohlmann; Thomas Schaub; A. Stephen K. Hashmi

doi:10.1039/c8gc01025k

Homogeneous catalysed hydrogenation of HMF

Alban Cadu, Kohei Sekine, Jaroslaw Mormul, Dominik M. Ohlmann, Thomas Schaub, A. Stephen K. Hashmi

Research output: Contribution to journal › Article

4 Citations (Scopus)

Abstract

In this report, hydroxymethylfurfural (HMF) is used as a bio-based feedstock for homogeneous metal-catalysed hydrogenation. Several ligand classes and metals are employed to reduce the aldehyde and aromatic ring of HMF. The previously unknown homogeneous catalysed hydrogenation of HMF to tetrahydrofuran-dimethanol (THFDM) was investigated using different catalyst systems. NHCs and phosphites give higher trans/cis ratios (between 1:1.25 and 1:3.95) of the product THFDM, but low conversions of only up to 17% accompanied by up to 92% yield of bis(hydroxymethyl)furan at 10 bar H ₂ and 120 °C. Conversely, di-phosphine ligated ruthenium catalysts in up to 87% yield lead to the highest overall conversion but only moderate trans/cis ratios of only 1:3.1-1:5.

Original language	English
Pages (from-to)	3386-3393
Number of pages	8
Journal	Green Chemistry
Volume	20
Issue number	14
DOIs	https://doi.org/10.1039/c8gc01025k
Publication status	Published - Jan 1 2018
Externally published	Yes

Fingerprint

All Science Journal Classification (ASJC) codes

Environmental Chemistry
Pollution

Cite this

Cadu, A., Sekine, K., Mormul, J., Ohlmann, D. M., Schaub, T., & Hashmi, A. S. K. (2018). Homogeneous catalysed hydrogenation of HMF. Green Chemistry, 20(14), 3386-3393. https://doi.org/10.1039/c8gc01025k

@article{e69b509a2cbb49559b8fcbcda17a5f68,

title = "Homogeneous catalysed hydrogenation of HMF",

abstract = "In this report, hydroxymethylfurfural (HMF) is used as a bio-based feedstock for homogeneous metal-catalysed hydrogenation. Several ligand classes and metals are employed to reduce the aldehyde and aromatic ring of HMF. The previously unknown homogeneous catalysed hydrogenation of HMF to tetrahydrofuran-dimethanol (THFDM) was investigated using different catalyst systems. NHCs and phosphites give higher trans/cis ratios (between 1:1.25 and 1:3.95) of the product THFDM, but low conversions of only up to 17{\%} accompanied by up to 92{\%} yield of bis(hydroxymethyl)furan at 10 bar H 2 and 120 °C. Conversely, di-phosphine ligated ruthenium catalysts in up to 87{\%} yield lead to the highest overall conversion but only moderate trans/cis ratios of only 1:3.1-1:5.",

author = "Alban Cadu and Kohei Sekine and Jaroslaw Mormul and Ohlmann, {Dominik M.} and Thomas Schaub and Hashmi, {A. Stephen K.}",

year = "2018",

month = "1",

day = "1",

doi = "10.1039/c8gc01025k",

language = "English",

volume = "20",

pages = "3386--3393",

journal = "Green Chemistry",

issn = "1463-9262",

publisher = "Royal Society of Chemistry",

number = "14",

}

TY - JOUR

T1 - Homogeneous catalysed hydrogenation of HMF

AU - Cadu, Alban

AU - Sekine, Kohei

AU - Mormul, Jaroslaw

AU - Ohlmann, Dominik M.

AU - Schaub, Thomas

AU - Hashmi, A. Stephen K.

PY - 2018/1/1

Y1 - 2018/1/1

N2 - In this report, hydroxymethylfurfural (HMF) is used as a bio-based feedstock for homogeneous metal-catalysed hydrogenation. Several ligand classes and metals are employed to reduce the aldehyde and aromatic ring of HMF. The previously unknown homogeneous catalysed hydrogenation of HMF to tetrahydrofuran-dimethanol (THFDM) was investigated using different catalyst systems. NHCs and phosphites give higher trans/cis ratios (between 1:1.25 and 1:3.95) of the product THFDM, but low conversions of only up to 17% accompanied by up to 92% yield of bis(hydroxymethyl)furan at 10 bar H 2 and 120 °C. Conversely, di-phosphine ligated ruthenium catalysts in up to 87% yield lead to the highest overall conversion but only moderate trans/cis ratios of only 1:3.1-1:5.

AB - In this report, hydroxymethylfurfural (HMF) is used as a bio-based feedstock for homogeneous metal-catalysed hydrogenation. Several ligand classes and metals are employed to reduce the aldehyde and aromatic ring of HMF. The previously unknown homogeneous catalysed hydrogenation of HMF to tetrahydrofuran-dimethanol (THFDM) was investigated using different catalyst systems. NHCs and phosphites give higher trans/cis ratios (between 1:1.25 and 1:3.95) of the product THFDM, but low conversions of only up to 17% accompanied by up to 92% yield of bis(hydroxymethyl)furan at 10 bar H 2 and 120 °C. Conversely, di-phosphine ligated ruthenium catalysts in up to 87% yield lead to the highest overall conversion but only moderate trans/cis ratios of only 1:3.1-1:5.

UR - http://www.scopus.com/inward/record.url?scp=85050504126&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85050504126&partnerID=8YFLogxK

U2 - 10.1039/c8gc01025k

DO - 10.1039/c8gc01025k

M3 - Article

AN - SCOPUS:85050504126

VL - 20

SP - 3386

EP - 3393

JO - Green Chemistry

JF - Green Chemistry

SN - 1463-9262

IS - 14

ER -

Access to Document

10.1039/c8gc01025k