Valuable new platform chemicals obtained by valorisation of a model succinic acid and bio-succinic acid with an ionic liquid and high-pressure carbon dioxide

Daniel B. Silva, Ewa Bogel-Lukasik

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The potential application of biomass and catalysts is crucial to form a bridge between the emerging bio-based industry and the current process technology. Using this approach to succinic acid, a biomass derived acid, might lead to new routes for derivative production, opening its transition to the industrial scale. A considerable number of succinic acid-based products were obtained in this work in advanced, "one-pot" processes executed in a green solvent, supercritical carbon dioxide. Ionic liquids, which present an alternative to volatile and flammable solvents, allowed for a subsequent transformation of carbohydrate rich renewable feedstock by a simple reaction in alternative media. Reactions give a possibility of conversion of a cheap lignocellulosic biomass to succinic acid-based products, such as ethanol having a potential application in biorefinery, as well as to pyrrolidine-2,5-diones, representing antibiotics and to succinic acid esters, valuable platform chemicals. Mechanistic analysis of the formation of reaction products was successfully developed. The valorisation of a model succinic acid was compared with the valorisation of a bioderived succinic acid under identical reaction conditions and the results are discussed. The palladium catalyst nanoparticles formed seem to be stabilised by ionic liquids allowing for five successive cycles with efficient conversion and selectivity in the hydrogenation of bio-succinic acid. The presented valorisation of a biomass derived carboxylic acid is an excellent starting point for derivative production.

Original languageEnglish
Pages (from-to)4048-4060
Number of pages13
JournalGreen Chemistry
Volume19
Issue number17
DOIs
Publication statusPublished - 7 Sep 2017

Fingerprint

Ionic Liquids
Succinic Acid
Ionic liquids
Carbon Dioxide
Carbon dioxide
carbon dioxide
Pressure
Acids
acid
Biomass
biomass
Derivatives
catalyst
Catalysts
Hydrogenation
Palladium
Carboxylic Acids
chemical
ionic liquid
Reaction products

Keywords

  • AQUEOUS-PHASE HYDROGENATION
  • HETEROGENEOUS CATALYTIC-HYDROGENATION
  • SUPERCRITICAL CO2 MEDIUM
  • SELECTIVE HYDROGENATION
  • RENEWABLE RESOURCES
  • TETRAHYDROFURAN THF
  • GAMMA-BUTYROLACTONE
  • PD/TIO2 CATALYSTS
  • PD/AL2O3 CATALYST
  • REUSABLE CATALYST

Cite this

@article{56184af14823446ab9287a1fcde2dc42,
title = "Valuable new platform chemicals obtained by valorisation of a model succinic acid and bio-succinic acid with an ionic liquid and high-pressure carbon dioxide",
abstract = "The potential application of biomass and catalysts is crucial to form a bridge between the emerging bio-based industry and the current process technology. Using this approach to succinic acid, a biomass derived acid, might lead to new routes for derivative production, opening its transition to the industrial scale. A considerable number of succinic acid-based products were obtained in this work in advanced, {"}one-pot{"} processes executed in a green solvent, supercritical carbon dioxide. Ionic liquids, which present an alternative to volatile and flammable solvents, allowed for a subsequent transformation of carbohydrate rich renewable feedstock by a simple reaction in alternative media. Reactions give a possibility of conversion of a cheap lignocellulosic biomass to succinic acid-based products, such as ethanol having a potential application in biorefinery, as well as to pyrrolidine-2,5-diones, representing antibiotics and to succinic acid esters, valuable platform chemicals. Mechanistic analysis of the formation of reaction products was successfully developed. The valorisation of a model succinic acid was compared with the valorisation of a bioderived succinic acid under identical reaction conditions and the results are discussed. The palladium catalyst nanoparticles formed seem to be stabilised by ionic liquids allowing for five successive cycles with efficient conversion and selectivity in the hydrogenation of bio-succinic acid. The presented valorisation of a biomass derived carboxylic acid is an excellent starting point for derivative production.",
keywords = "AQUEOUS-PHASE HYDROGENATION, HETEROGENEOUS CATALYTIC-HYDROGENATION, SUPERCRITICAL CO2 MEDIUM, SELECTIVE HYDROGENATION, RENEWABLE RESOURCES, TETRAHYDROFURAN THF, GAMMA-BUTYROLACTONE, PD/TIO2 CATALYSTS, PD/AL2O3 CATALYST, REUSABLE CATALYST",
author = "Silva, {Daniel B.} and Ewa Bogel-Lukasik",
note = "This work was supported by Fundacao para a Ciencia e Tecnologia (PEst-C/EQB/LA0006/2013 and IF/01643/2013). This work was supported by COST Actions: CM 1304: {"}Emergence and Evolution of Complex Chemical Systems{"} and FPS COST Action FP1306: {"}Valorisation of lignocellulosic biomass side streams for sustainable production of chemicals, materials & fuels using low environmental impact technologies{"}. We would like to acknowledge the catalyst characterisation measurement performed by Dr Nuno Costa, Prof. Isabel Fonseca, and Dr Isabel Nogueira, with the financial support of projects: Plurianual 2017 and IF/01643/2013/CP1161/CT0004.",
year = "2017",
month = "9",
day = "7",
doi = "10.1039/c7gc00952f",
language = "English",
volume = "19",
pages = "4048--4060",
journal = "Green Chemistry",
issn = "1463-9262",
publisher = "ROYAL SOC CHEMISTRY",
number = "17",

}

TY - JOUR

T1 - Valuable new platform chemicals obtained by valorisation of a model succinic acid and bio-succinic acid with an ionic liquid and high-pressure carbon dioxide

AU - Silva, Daniel B.

AU - Bogel-Lukasik, Ewa

N1 - This work was supported by Fundacao para a Ciencia e Tecnologia (PEst-C/EQB/LA0006/2013 and IF/01643/2013). This work was supported by COST Actions: CM 1304: "Emergence and Evolution of Complex Chemical Systems" and FPS COST Action FP1306: "Valorisation of lignocellulosic biomass side streams for sustainable production of chemicals, materials & fuels using low environmental impact technologies". We would like to acknowledge the catalyst characterisation measurement performed by Dr Nuno Costa, Prof. Isabel Fonseca, and Dr Isabel Nogueira, with the financial support of projects: Plurianual 2017 and IF/01643/2013/CP1161/CT0004.

PY - 2017/9/7

Y1 - 2017/9/7

N2 - The potential application of biomass and catalysts is crucial to form a bridge between the emerging bio-based industry and the current process technology. Using this approach to succinic acid, a biomass derived acid, might lead to new routes for derivative production, opening its transition to the industrial scale. A considerable number of succinic acid-based products were obtained in this work in advanced, "one-pot" processes executed in a green solvent, supercritical carbon dioxide. Ionic liquids, which present an alternative to volatile and flammable solvents, allowed for a subsequent transformation of carbohydrate rich renewable feedstock by a simple reaction in alternative media. Reactions give a possibility of conversion of a cheap lignocellulosic biomass to succinic acid-based products, such as ethanol having a potential application in biorefinery, as well as to pyrrolidine-2,5-diones, representing antibiotics and to succinic acid esters, valuable platform chemicals. Mechanistic analysis of the formation of reaction products was successfully developed. The valorisation of a model succinic acid was compared with the valorisation of a bioderived succinic acid under identical reaction conditions and the results are discussed. The palladium catalyst nanoparticles formed seem to be stabilised by ionic liquids allowing for five successive cycles with efficient conversion and selectivity in the hydrogenation of bio-succinic acid. The presented valorisation of a biomass derived carboxylic acid is an excellent starting point for derivative production.

AB - The potential application of biomass and catalysts is crucial to form a bridge between the emerging bio-based industry and the current process technology. Using this approach to succinic acid, a biomass derived acid, might lead to new routes for derivative production, opening its transition to the industrial scale. A considerable number of succinic acid-based products were obtained in this work in advanced, "one-pot" processes executed in a green solvent, supercritical carbon dioxide. Ionic liquids, which present an alternative to volatile and flammable solvents, allowed for a subsequent transformation of carbohydrate rich renewable feedstock by a simple reaction in alternative media. Reactions give a possibility of conversion of a cheap lignocellulosic biomass to succinic acid-based products, such as ethanol having a potential application in biorefinery, as well as to pyrrolidine-2,5-diones, representing antibiotics and to succinic acid esters, valuable platform chemicals. Mechanistic analysis of the formation of reaction products was successfully developed. The valorisation of a model succinic acid was compared with the valorisation of a bioderived succinic acid under identical reaction conditions and the results are discussed. The palladium catalyst nanoparticles formed seem to be stabilised by ionic liquids allowing for five successive cycles with efficient conversion and selectivity in the hydrogenation of bio-succinic acid. The presented valorisation of a biomass derived carboxylic acid is an excellent starting point for derivative production.

KW - AQUEOUS-PHASE HYDROGENATION

KW - HETEROGENEOUS CATALYTIC-HYDROGENATION

KW - SUPERCRITICAL CO2 MEDIUM

KW - SELECTIVE HYDROGENATION

KW - RENEWABLE RESOURCES

KW - TETRAHYDROFURAN THF

KW - GAMMA-BUTYROLACTONE

KW - PD/TIO2 CATALYSTS

KW - PD/AL2O3 CATALYST

KW - REUSABLE CATALYST

UR - http://www.scopus.com/inward/record.url?scp=85028679371&partnerID=8YFLogxK

U2 - 10.1039/c7gc00952f

DO - 10.1039/c7gc00952f

M3 - Article

VL - 19

SP - 4048

EP - 4060

JO - Green Chemistry

JF - Green Chemistry

SN - 1463-9262

IS - 17

ER -