Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Reductive Hydroformylation of Isosorbide Diallyl Ether.

ABSTRACT: Isosorbide and its functionalized derivatives have numerous applications as bio-sourced building blocks. In this context, the synthesis of diols from isosorbide diallyl ether by hydrohydroxymethylation reaction is of extreme interest. This hydrohydroxymethylation, which consists of carbon-carbon double bonds converting into primary alcohol functions, can be obtained by a hydroformylation reaction followed by a hydrogenation reaction. In this study, reductive hydroformylation was achieved using isosorbide diallyl ether as a substrate in a rhodium/amine catalytic system. The highest yield in bis-primary alcohols obtained was equal to 79%.

SUBMITTER: Ternel J

PROVIDER: S-EPMC8658770 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Reductive Hydroformylation of Isosorbide Diallyl Ether.

Ternel Jérémy J Lopes Adrien A Sauthier Mathieu M Buffe Clothilde C Wiatz Vincent V Bricout Hervé H Tilloy Sébastien S Monflier Eric E

Molecules (Basel, Switzerland) 20211202 23

Isosorbide and its functionalized derivatives have numerous applications as bio-sourced building blocks. In this context, the synthesis of diols from isosorbide diallyl ether by hydrohydroxymethylation reaction is of extreme interest. This hydrohydroxymethylation, which consists of carbon-carbon double bonds converting into primary alcohol functions, can be obtained by a hydroformylation reaction followed by a hydrogenation reaction. In this study, reductive hydroformylation was achieved using i ...[more]

PMID: 34885903

Similar Datasets

Auto-Tandem Catalytic Reductive Hydroformylation in a CO<sub>2</sub>-Switchable Solvent System.

Project description:Upgradation of olefin-enriched Fischer-Tropsch cuts by the synthesis of alcohols leads to drop-in-capable biosynthetic fuels with low carbon emissions. As an alternative to the conventional two-step production of long-chain alcohols, tandem catalytic systems improve the energy and resource efficiency. Herein, we present an auto-tandem catalytic system for the production of alcohols from olefin-paraffin mixtures. By utilization of a tertiary alkanolamine as the ligand as well as the switchable component in the solvent system, a lean reaction system capable of catalyst recycling was developed. The system was characterized with regard to the switchable solvent separation approach and reaction parameters, resulting in alcohol yields of up to 99.5% and turnover frequencies of up to 764 h-1. By recycling the catalyst in 10 consecutive reactions, a total turnover number of 2810 was achieved.

| S-EPMC8942186 | biostudies-literature

Green Process Design for Reductive Hydroformylation of Renewable Olefin Cuts for Drop-In Diesel Fuels.

Project description:CO2 -neutral fuels are a way to cleaner and more sustainable mobility. Utilization of bio-syngas via Fischer-Tropsch (FT) synthesis represents an interesting route for the production of tailormade biofuels. Recent developments in FT catalyst research led to olefin-enriched products, enabling the synthesis of alcohol-enriched fuels by reductive hydroformylation of the C=C bond. Several alcohols have already proven to be suitable fuel additives with favorable combustion behavior. Here, a hydroformylation-hydrogenation sequence of FT-olefin-paraffin mixtures was investigated as a potential route to alcohols. A liquid-liquid biphasic system with a rhodium/3,3',3''-phosphanetriyltris(benzenesulfonic acid) trisodium salt (TPPTS) catalyst system was chosen for effective catalyst recycling. After optimizing reaction conditions with a model substrate consisting of 1-octene and n-heptane the conversion of an actual olefin-containing C5 -C10 FT product fraction to alcohols in continuously operated processes for 37 h was achieved with a total turnover number of 23679.

| S-EPMC9291018 | biostudies-literature

Reductive elimination of ether from T-shaped, monomeric arylpalladium alkoxides.

Project description: Not available

| S-EPMC2819327 | biostudies-literature

Direct Conversion of Syngas to Higher Alcohols via Tandem Integration of Fischer-Tropsch Synthesis and Reductive Hydroformylation.

Project description:The selective conversion of syngas to higher alcohols is an attractive albeit elusive route in the quest for effective production of chemicals from alternative carbon resources. We report the tandem integration of solid cobalt Fischer-Tropsch and molecular hydroformylation catalysts in a one-pot slurry-phase process. Unprecedented selectivities (>50 wt %) to C2+ alcohols are achieved at CO conversion levels >70 %, alongside negligible CO2 side-production. The efficient overall transformation is enabled by catalyst engineering, bridging gaps in operation temperature and intrinsic selectivity which have classically precluded integration of these reactions in a single conversion step. Swift capture of 1-olefin Fischer-Tropsch primary products by the molecular hydroformylation catalyst, presumably within the pores of the solid catalyst is key for high alcohol selectivity. The results underscore that controlled cooperation between solid aggregate and soluble molecular metal catalysts, which pertain to traditionally dichotomic realms of heterogeneous and homogeneous catalysis, is a promising blueprint toward selective conversion processes.

| S-EPMC9400900 | biostudies-literature

Rhodium/Trialkylamines Catalyzed Reductive Hydroformylation in Ionic Liquid/Heptane Medium: An Unexpected Concept for Catalyst Recycling in Batch and Continuous Flow Processes.

Project description:We report here the rhodium catalyzed reductive hydroformylation of methyl 10-undecenoate. Our approach is based on an ionic liquid/heptane biphasic system associated with commercially available trialkylamines. The effects of various reaction parameters such as amine type, amine amount, temperature, syngas pressure and composition were studied in order to minimize the rhodium leaching and increase the production of primary alcohols. Although the amine is less soluble in the ionic liquid than in heptane, the catalytic system is efficiently maintained in the ionic liquid phase. For the optimized conditions, the catalytic ionic liquid layer can be recycled at least nine times by keeping an alcohol yield over 50 % and by limiting the rhodium leaching. As an extension of this system and to examine the long-term stability, this batch system was transferred to a miniplant for a continuous flow process. A pilot plant was operated for 45 h of total reaction time, reaching a TTON of 232 for alcohol production.

| S-EPMC11789979 | biostudies-literature

Robust, scalable, and highly selective spirocyclic catalysts for industrial hydroformylation and isomerization-hydroformylation.

Project description:Hydroformylation (HF) or isomerization-hydroformylation (ISO-HF) represents the most direct and practical route for producing aldehydes on an industrial scale. To resolve the issues of low activity, low linear/branched (l/b) ratio, and low stability in HF and ISO-HF, we herein reported a class of spirocyclic diphosphites. Notably, the ligand termed O-SDPhite afforded excellent catalytic activity and regioselectivity for the HF of various olefins. Excellent l/b ratio and an unprecedented turnover number of up to 17,620,000 were achieved. O-SDPhite was also found to be effective in the regioselective ISO-HF of the industrially related cheap and abundant C4 Raffinates to n-valeraldehyde produced on a multimillion-ton scale. The reaction with O-SDPhite, superior to that of benchmark Biphephos, was continuously operated for 41 days and afforded an average 38.6 l/b ratio (31 days and 14.7 l/b ratio for Biphephos).

| S-EPMC466942 | biostudies-literature

Effector responsive hydroformylation catalysis.

Project description:Herein, we report a supramolecular rhodium complex that can form dimeric or monomeric Rh-species catalytically active in hydroformylation, depending on the binding of effectors within the integrated DIM-receptor. X-ray crystal structures, in situ (high-pressure (HP)) spectroscopy studies, and molecular modelling studies show that in the absence of effectors, the preferred Rh-species formed is the dimer, of which two ligands coordinate to two rhodium metals. Importantly, upon binding guest molecules, -effectors-, to the DIM-receptor under hydroformylation conditions, the monomeric Rh-active species is formed, as evidenced by a combination of in situ HP NMR and IR spectroscopy studies and molecular modelling. As the monomeric complex has different catalytic properties from the dimeric complex, we effectively generate a catalytic system of which the properties respond to the presence of effectors, reminiscent of how the properties of proteins are regulated in nature. Indeed, catalytic and kinetic experiments show that both the selectivity and activity of this supramolecular catalytic system can be influenced in the hydroformylation of 1-octene using acetate as an effector that shift the equilibrium from the dimeric to monomeric species.

| S-EPMC6713872 | biostudies-literature

Enantioselective hydroformylation of aniline derivatives.

Project description:We have developed a ligand that reversibly binds to aniline substrates, allowing for the control of regioselectivity and enantioselectivity in hydroformylation. In this paper we address how the electronics of the aniline ring affect both the binding of the substrate to the ligand and the enantioselectivity in this reaction.

| S-EPMC3170429 | biostudies-literature

Regioselective hydroformylation of allylic alcohols.

Project description:A highly regioselective hydroformylation of allylic alcohols is reported toward the synthesis of β-hydroxy-acid and aldehyde products. The selectivity is achieved through the use of a ligand that reversibly binds to alcohols in situ, allowing for a directed hydroformylation to occur. The application to trisubstituted olefins was also demonstrated, which yields a single diastereomer product consistent with a stereospecific addition of CO and hydrogen.

| S-EPMC3096926 | biostudies-literature

Fabrication of Two Polyester Nanofiber Types Containing the Biobased Monomer Isosorbide: Poly (Ethylene Glycol 1,4-Cyclohexane Dimethylene Isosorbide Terephthalate) and Poly (1,4-Cyclohexane Dimethylene Isosorbide Terephthalate).

Project description:The thermal and mechanical properties of two types of polyester nanofiber, poly (1,4-cyclohexanedimethylene isosorbide terephthalate) (PICT) copolymers and the terpolyester of isosorbide, ethylene glycol, 1,4-cyclohexane dimethanol, and terephthalic acid (PEICT), were investigated. This is the first attempt to fabricate PICT nanofiber via the electrospinning method; comparison with PEICT nanofiber could give greater understanding of eco-friendly nanofibers containing biomass monomers. The nanofibers fabricated from each polymer show similar smooth and thin-and-long morphologies. On the other hand, the polymers exhibited significantly different mechanical and thermal properties; in particular, a higher tensile strength was observed for PICT nanofiber mat than for that of PEICT. We hypothesized that PICT has more trans-configuration than PEICT, resulting in enhancement of its tensile strength, and demonstrated this by Fourier transform infrared spectroscopy. In addition, PICT nanofibers showed clear crystallization behavior upon increased temperature, while PEICT nanofibers showed completely amorphous structure. Both nanofibers have better tensile properties and thermal stability than the typical polyester polymer, implying that they can be utilized in various industrial applications.

| S-EPMC5853689 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data