Rhodium-catalyzed hydroformylation in γ-valerolactone as a biomass-derived solvent

Péter Pongrácz, Brigitta Bartal, L. Kollár, László T. Mika

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Rhodium-catalyzed hydroformylation of styrene, α-methylstyrene, dimethyl itaconate, and (R)-limonene was performed in gamma-valerolactone (GVL) as a proposed biomass-based environmentally benign solvent for hydroformylation referring to toluene as a generally used conventional solvent. Both achiral (triphenylphosphine, 1,3-bis(diphenylphoshino)propane) and enantiopure bidentate phosphine ligands ((S,S)-BDPP, (R)-BINAP, (R)-QUINAP, (R,R)-DIOP, (Rc),(Sp)-JOSIPHOS, (S)-SEGPHOS, (S)-(DM)-SEGPHOS) were investigated in in situ generated Rh-diphosphine catalyst systems. In general, the catalysts' activity in GVL was lower than in toluene; however, remarkable chemo- (>99%) and regioselectivities (>95%) were achieved in GVL under identical conditions. The BDPP-modified Rh-catalyst was recycled for three consecutive cycles; however a decrease in its activity was detected.

Original languageEnglish
Pages (from-to)140-145
Number of pages6
JournalJournal of Organometallic Chemistry
Volume847
DOIs
Publication statusPublished - Oct 1 2017

Fingerprint

Hydroformylation
Rhodium
biomass
rhodium
Biomass
Toluene
phosphine
catalysts
Regioselectivity
Catalysts
toluene
Propane
Styrene
Catalyst activity
Ligands
styrenes
phosphines
propane
ligands
cycles

Keywords

  • Alternative solvent
  • Gamma-valerolactone
  • Homogeneous catalysis
  • Hydroformylation
  • Rhodium

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Rhodium-catalyzed hydroformylation in γ-valerolactone as a biomass-derived solvent. / Pongrácz, Péter; Bartal, Brigitta; Kollár, L.; Mika, László T.

In: Journal of Organometallic Chemistry, Vol. 847, 01.10.2017, p. 140-145.

Research output: Contribution to journalArticle

Pongrácz, Péter ; Bartal, Brigitta ; Kollár, L. ; Mika, László T. / Rhodium-catalyzed hydroformylation in γ-valerolactone as a biomass-derived solvent. In: Journal of Organometallic Chemistry. 2017 ; Vol. 847. pp. 140-145.
@article{4fc9b71953394166b3975f477d1bb676,
title = "Rhodium-catalyzed hydroformylation in γ-valerolactone as a biomass-derived solvent",
abstract = "Rhodium-catalyzed hydroformylation of styrene, α-methylstyrene, dimethyl itaconate, and (R)-limonene was performed in gamma-valerolactone (GVL) as a proposed biomass-based environmentally benign solvent for hydroformylation referring to toluene as a generally used conventional solvent. Both achiral (triphenylphosphine, 1,3-bis(diphenylphoshino)propane) and enantiopure bidentate phosphine ligands ((S,S)-BDPP, (R)-BINAP, (R)-QUINAP, (R,R)-DIOP, (Rc),(Sp)-JOSIPHOS, (S)-SEGPHOS, (S)-(DM)-SEGPHOS) were investigated in in situ generated Rh-diphosphine catalyst systems. In general, the catalysts' activity in GVL was lower than in toluene; however, remarkable chemo- (>99{\%}) and regioselectivities (>95{\%}) were achieved in GVL under identical conditions. The BDPP-modified Rh-catalyst was recycled for three consecutive cycles; however a decrease in its activity was detected.",
keywords = "Alternative solvent, Gamma-valerolactone, Homogeneous catalysis, Hydroformylation, Rhodium",
author = "P{\'e}ter Pongr{\'a}cz and Brigitta Bartal and L. Koll{\'a}r and Mika, {L{\'a}szl{\'o} T.}",
year = "2017",
month = "10",
day = "1",
doi = "10.1016/j.jorganchem.2017.04.029",
language = "English",
volume = "847",
pages = "140--145",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",

}

TY - JOUR

T1 - Rhodium-catalyzed hydroformylation in γ-valerolactone as a biomass-derived solvent

AU - Pongrácz, Péter

AU - Bartal, Brigitta

AU - Kollár, L.

AU - Mika, László T.

PY - 2017/10/1

Y1 - 2017/10/1

N2 - Rhodium-catalyzed hydroformylation of styrene, α-methylstyrene, dimethyl itaconate, and (R)-limonene was performed in gamma-valerolactone (GVL) as a proposed biomass-based environmentally benign solvent for hydroformylation referring to toluene as a generally used conventional solvent. Both achiral (triphenylphosphine, 1,3-bis(diphenylphoshino)propane) and enantiopure bidentate phosphine ligands ((S,S)-BDPP, (R)-BINAP, (R)-QUINAP, (R,R)-DIOP, (Rc),(Sp)-JOSIPHOS, (S)-SEGPHOS, (S)-(DM)-SEGPHOS) were investigated in in situ generated Rh-diphosphine catalyst systems. In general, the catalysts' activity in GVL was lower than in toluene; however, remarkable chemo- (>99%) and regioselectivities (>95%) were achieved in GVL under identical conditions. The BDPP-modified Rh-catalyst was recycled for three consecutive cycles; however a decrease in its activity was detected.

AB - Rhodium-catalyzed hydroformylation of styrene, α-methylstyrene, dimethyl itaconate, and (R)-limonene was performed in gamma-valerolactone (GVL) as a proposed biomass-based environmentally benign solvent for hydroformylation referring to toluene as a generally used conventional solvent. Both achiral (triphenylphosphine, 1,3-bis(diphenylphoshino)propane) and enantiopure bidentate phosphine ligands ((S,S)-BDPP, (R)-BINAP, (R)-QUINAP, (R,R)-DIOP, (Rc),(Sp)-JOSIPHOS, (S)-SEGPHOS, (S)-(DM)-SEGPHOS) were investigated in in situ generated Rh-diphosphine catalyst systems. In general, the catalysts' activity in GVL was lower than in toluene; however, remarkable chemo- (>99%) and regioselectivities (>95%) were achieved in GVL under identical conditions. The BDPP-modified Rh-catalyst was recycled for three consecutive cycles; however a decrease in its activity was detected.

KW - Alternative solvent

KW - Gamma-valerolactone

KW - Homogeneous catalysis

KW - Hydroformylation

KW - Rhodium

UR - http://www.scopus.com/inward/record.url?scp=85018986546&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85018986546&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2017.04.029

DO - 10.1016/j.jorganchem.2017.04.029

M3 - Article

VL - 847

SP - 140

EP - 145

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

ER -