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Use of green solvents and their mixtures for optimizing chemical processes

Grant number: 14/22136-4
Support type:Research Projects - Thematic Grants
Duration: July 01, 2015 - June 30, 2022
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal researcher:Omar Abou El Seoud
Grantee:Omar Abou El Seoud
Home Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil
Principal researchers:Erick Leite Bastos ; Joséf Wilhelm Baader
Associated grant(s):17/06394-1 - Muti-user equipment approved in grant 2014/22136-4: isothermal titration calorimeter (ITC) for the determination of thermodynamic parameters of molecular interactions, AP.EMU
Associated scholarship(s):19/02928-7 - Ionic liquids (ILs) recyclable for cellulose dissolution and regeneration: molecular structure / performance ratio, and properties of regenerated cellulose, BP.IC
18/19101-5 - Effect of antioxidants on the persistence of betalains in solutions, BP.IC
18/20592-3 - Build of a modular photoreactor, BP.IC
+ associated scholarships 18/06546-9 - Antioxidant capacity of a betalain-nitrone, BP.IC
17/20133-6 - Effect of N-methylation over the hydrolytic stability and fluorescence of betalainic probes, BP.MS
16/22869-7 - Novel solvents in cellulose chemistry: synthesis, properties, and application of quaternaryammonium electrolytes for dissolution, regeneration, and derivatization of cellulose, BP.PD
16/04648-3 - Hydrolysis of betalains in the presence of surfactants, BP.IC
15/25378-1 - Semisynthesis and photophysical properties of pyrrolic betalains, BP.IC
15/18474-4 - Functionalization of polysaccharides with photoresponsive betalains, BP.DD - associated scholarships

Abstract

This thematic project aims to rationalize, in molecular terms, the interactions between solutes and pure solvents or their binary mixtures and to apply this knowledge to optimize chemical processes of interest. Where possible, green solvents with low environmental impact will be employed, for example, water, esters of carbonic acid, and ionic liquids. The goals of this project include determination of the effects of the structure of ionic liquids and molecular solvents, as well as the composition of the corresponding mixtures on their ability to solubilize cellulose and control its derivatization in terms of degree of substitution and product regioselectivity. The use of suitable solvents and their binary mixtures is expected to increase both the light emission efficiency of analytically relevant chemiluminescent reactions, and the fabrication of cellulose nanocomposites. Solvents will be selected according to their macroscopic and microscopic properties. The microscopic parameters will be determined by studying the solvatochromic behavior of natural, semisynthetic and synthetic dyes. The thermodynamic properties of the interaction between the solute and the medium will be determined by isothermal titration calorimetry. (AU)

Articles published in Agência FAPESP Newsletter about the research grant:
Springer lança livro sobre derivados de celulose com autor brasileiro 
Articles published in other media outlets (1 total):
Agrosoft: O pigmento azul natural que é derivado da beterraba (26/May/2020)

Scientific publications (51)
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
KEPPELER, NICOLAS; GALGANO, PAULA D.; SANTOS, SORAYA DA SILVA; MALEK, I, NAVED; EL SEOUD, OMAR A. On the effects of head-group volume on the adsorption and aggregation of 1-(n-hexadecyl)-3-C-m-imidazolium bromide and chloride surfactants in aqueous solutions. JOURNAL OF MOLECULAR LIQUIDS, v. 328, APR 15 2021. Web of Science Citations: 1.
EL SEOUD, OMAR A.; KEPPELER, NICOLAS; MALEK, NAVED I.; GALGANO, PAULA D. Ionic Liquid-Based Surfactants: Recent Advances in Their Syntheses, Solution Properties, and Applications. POLYMERS, v. 13, n. 7 APR 2021. Web of Science Citations: 0.
CABELLO, MAIDILEYVIS C.; BELLO, LIENA V.; BAADER, WILHELM J. Use of coumarin derivatives as activators in the peroxyoxalate system in organic and aqueous media. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, v. 408, MAR 1 2021. Web of Science Citations: 0.
EL SEOUD, OMAR A.; BIONI, THAIS A.; DIGNANI, MARCELLA T. Understanding cellulose dissolution in ionic liquid-dimethyl sulfoxide binary mixtures: Quantification of the relative importance of hydrogen bonding and hydrophobic interactions. JOURNAL OF MOLECULAR LIQUIDS, v. 322, JAN 15 2021. Web of Science Citations: 0.
KOSTAG, MARC; JEDVERT, KERSTIN; EL SEOUD, OMAR A. Engineering of sustainable biomaterial composites from cellulose and silk fibroin: Fundamentals and applications. International Journal of Biological Macromolecules, v. 167, p. 687-718, JAN 15 2021. Web of Science Citations: 0.
DIGNANI, MARCELLA T.; BIONI, THAIS A.; PAIXAO, THIAGO R. L. C.; EL SEOUD, OMAR A. Cellulose Dissolution in Mixtures of Ionic Liquids and Dimethyl Sulfoxide: A Quantitative Assessment of the Relative Importance of Temperature and Composition of the Binary Solvent. Molecules, v. 25, n. 24 DEC 2020. Web of Science Citations: 0.
AUGUSTO, FELIPE A.; BARTOLONI, FERNANDO H.; PAGANO, ANA PAULA E.; BAADER, WILHELM J. Mechanistic Study of the Peroxyoxalate System in Completely Aqueous Carbonate Buffer. Photochemistry and Photobiology, v. 97, n. 2 NOV 2020. Web of Science Citations: 0.
BIONI, THAIS A.; DE OLIVEIRA, MAYARA L.; DIGNANI, MARCELLA T.; EL SEOUD, OMAR A. Understanding the efficiency of ionic liquids-DMSO as solvents for carbohydrates: use of solvatochromic- and related physicochemical properties. NEW JOURNAL OF CHEMISTRY, v. 44, n. 35, p. 14906-14914, SEP 21 2020. Web of Science Citations: 0.
FREITAS-DORR, B. C.; MACHADO, C. O.; PINHEIRO, A. C.; FERNANDES, A. B.; DORR, F. A.; PINTO, E.; LOPES-FERREIRA, M.; ABDELLAH, M.; SA, J.; RUSSO, L. C.; FORTI, F. L.; GONCALVES, L. C. P.; BASTOS, L. L. A metal-free blue chromophore derived from plant pigments. SCIENCE ADVANCES, v. 6, n. 14 APR 2020. Web of Science Citations: 0.
EL SEOUD, OMAR A.; KOSTAG, MARC; JEDVERT, KERSTIN; MALEK, NAVED I. Cellulose Regeneration and Chemical Recycling: Closing the ``Cellulose Gap{''} Using Environmentally Benign Solvents. MACROMOLECULAR MATERIALS AND ENGINEERING, v. 305, n. 4 FEB 2020. Web of Science Citations: 0.
FERNANDES, ARTHUR B.; PAVLIUK, V, MARIIA; PAUN, CRISTINA; CARVALHO, ALEXANDRINA C.; NOMURA, CASSIANA S.; LEWIN, ERIK; LINDBLAD, REBECKA; CAMARGO, PEDRO H. C.; SA, JACINTO; BASTOS, ERICK L. Recoverable and Reusable Polymer Microbead-Supported Metal Nanocatalysts for Redox Chemical Transformations. ACS APPLIED NANO MATERIALS, v. 3, n. 2, p. 1722-1730, FEB 2020. Web of Science Citations: 0.
GONCALVES, LETICIA C. P.; LOPES, NATHANA B.; AUGUSTO, FELIPE A.; PIOLI, RENAN M.; MACHADO, CAROLINE O.; FREITAS-DORR, BARBARA C.; SUFFREDINI, HUGO B.; BASTOS, ERICK L. Phenolic betalain as antioxidants: meta means more. Pure and Applied Chemistry, v. 92, n. 2, p. 243-253, FEB 2020. Web of Science Citations: 0.
CABELLO, MAIDILEYVIS C.; SOUZA, GLALCI A.; BELLO, V, LIENA; BAADER, WILHELM J. Mechanistic Studies on the Salicylate-Catalyzed Peroxyoxalate Chemiluminescence in Aqueous Medium. Photochemistry and Photobiology, v. 96, n. 1 DEC 2019. Web of Science Citations: 0.
EL SEOUD, OMAR A.; KOSTAG, MARC; JEDVERT, KERSTIN; MALEK, NAVED I. Cellulose in Ionic Liquids and Alkaline Solutions: Advances in the Mechanisms of Biopolymer Dissolution and Regeneration. POLYMERS, v. 11, n. 12 DEC 2019. Web of Science Citations: 0.
KOSTAG, MARC; DIGNANI, MARCELLA TEIXEIRA; LOURENCO, MATHEUS COSTA; BIONI, THAIS DE ALMEIDA; EL SEOUD, OMAR A. Assessing cellulose dissolution efficiency in solvent systems based on a robust experimental quantification protocol and enthalpy data. HOLZFORSCHUNG, v. 73, n. 12, p. 1103-1112, DEC 2019. Web of Science Citations: 3.
AUGUSTO, FELIPE A.; BARTOLONI, FERNANDO H.; CABELLO, MAIDILEYVIS C.; DOS SANTOS, ANA PAULA F.; BAADER, WILHELM J. Kinetic studies on 2,6-lutidine catalyzed peroxyoxalate chemiluminescence in organic and aqueous medium: Evidence for general base catalysis. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, v. 382, SEP 1 2019. Web of Science Citations: 1.
GODOY, ANNA P.; ECORCHARD, PETRA; BENES, HYNEK; TOLASZ, JAKUB; SMRZOVA, DARINA; SEIXAS, LEANDRO; PEDROTTI, JAIRO J.; DE SOUZA, EUNEZIO A. T.; EL SEOUD, OMAR A.; DONATO, RICARDO K. Ultrasound exfoliation of graphite in biphasic liquid systems containing ionic liquids: A study on the conditions for obtaining large few-layers graphene. ULTRASONICS SONOCHEMISTRY, v. 55, p. 279-288, JUL 2019. Web of Science Citations: 2.
NAKASHIMA, KARINA K.; BASTOS, ERICK L. Rationale on the High Radical Scavenging Capacity of Betalains. ANTIOXIDANTS, v. 8, n. 7 JUL 2019. Web of Science Citations: 0.
FERREIRA, DANIELA C.; OLIVEIRA, MAYARA L.; BIONI, THAIS A.; NAWAZ, HAQ; KING, ALISTAIR W. T.; KILPELAINEN, ILKKA; HUMMEL, MICHAEL; SIXTA, HERBERT; EL SEOUD, OMAR A. Binary mixtures of ionic liquids-DMSO as solvents for the dissolution and derivatization of cellulose: Effects of alkyl and alkoxy side chains. Carbohydrate Polymers, v. 212, p. 206-214, MAY 15 2019. Web of Science Citations: 4.
PIRES, PAULO A. R.; EL SEOUD, OMAR A.; MACHADO, VANDERLEI G.; DE JESUS, JESSICA C.; DE MELO, CARLOS E. A.; BUSKE, JONATAN L. O.; CARDOZO, AMANDA P. Understanding Solvation: Comparison of Reichardt's Solvatochromic Probe and Related Molecular ``Core{''} Structures. JOURNAL OF CHEMICAL AND ENGINEERING DATA, v. 64, n. 5, SI, p. 2213-2220, MAY 2019. Web of Science Citations: 0.
KOSTAG, MARC; EL SEOUD, OMAR A. Dependence of cellulose dissolution in quaternary ammonium-based ionic liquids/DMSO on the molecular structure of the electrolyte. Carbohydrate Polymers, v. 205, p. 524-532, FEB 1 2019. Web of Science Citations: 4.
KOSTAG, MARC; GERICKE, MARTIN; HEINZE, THOMAS; EL SEOUD, OMAR A. Twenty-five years of cellulose chemistry: innovations in the dissolution of the biopolymer and its transformation into esters and ethers. Cellulose, v. 26, n. 1, SI, p. 139-184, JAN 2019. Web of Science Citations: 6.
CABELLO, MAIDILEYVIS C.; EL SEOUD, OMAR A. A.; BAADER, WILHELM J. Effect of ionic liquids on the kinetics and quantum efficiency of peroxyoxalate chemiluminescence in aqueous media. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, v. 367, p. 471-478, DEC 1 2018. Web of Science Citations: 2.
PINHEIRO, AMANDA C.; GONCALVES, ANDRE B.; BAADER, WILHELM J.; YAMAGUCHI, LYDIA F.; MALEK, I, NAVED; BASTOS, ERICK L.; EL SEOUD, OMAR A. BIOFUELS FROM COCONUT FAT AND SOYBEAN OIL: MICROWAVE-ASSISTED SYNTHESIS AND GAS CHROMATOGRAPHY/MASS SPECTROMETRY ANALYSIS. Química Nova, v. 41, n. 10, p. 1200-1204, DEC 2018. Web of Science Citations: 1.
REIS, JOEL S.; FERNANDES, ARTHUR B.; FREITAS-DORR, BARBARA C.; BASTOS, ERICK L.; STEFANI, HELIO A. Oxazoline as acceptor moiety for excited-state intramolecular proton transfer. Tetrahedron, v. 74, n. 48, p. 6866-6872, NOV 29 2018. Web of Science Citations: 2.
ESTEVES, LARISSA C.; PINHEIRO, AMANDA C.; PIOLI, RENAN M.; PENNA, TATIANA C.; BAADER, WILHELM J.; CORRERA, THIAGO C.; BASTOS, ERICK L. Revisiting the Mechanism of Hydrolysis of Betanin. Photochemistry and Photobiology, v. 94, n. 5, p. 853-864, SEP-OCT 2018. Web of Science Citations: 6.
VACHER, MORGANE; GALVAN, IGNACIO FDEZ; DING, BO-WEN; SCHRAMM, STEFAN; BERRAUD-PACHE, ROMAIN; NAUMOV, PANCE; FERRE, NICOLAS; LIU, YA-JUN; NAVIZET, ISABELLE; ROCA-SANJUAN, DANIEL; BAADER, WILHELM J.; LINDH, ROLAND. Chemi- and Bioluminescence of Cyclic Peroxides. CHEMICAL REVIEWS, v. 118, n. 15, SI, p. 6927-6974, AUG 8 2018. Web of Science Citations: 53.
ESKILDSEN PAGANO, ANA PAULA; KHALID, NAUMAN; KOBAYASHI, ISAO; NAKAJIMA, MITSUTOSHI; NEVES, MARCOS ANTONIO; BASTOS, ERICK LEITE. Microencapsulation of betanin in monodisperse W/O/W emulsions. Food Research International, v. 109, p. 489-496, JUL 2018. Web of Science Citations: 0.
ACHTEL, CHRISTIAN; JEDVERT, KERSTIN; KOSTAG, MARC; EL SEOUD, OMAR A.; HEINZE, THOMAS. Surprising Insensitivity of Homogeneous Acetylation of Cellulose Dissolved in Triethyl(n-octyl)ammonium Chloride/Molecular Solvent on the Solvent Polarity. MACROMOLECULAR MATERIALS AND ENGINEERING, v. 303, n. 5 MAY 2018. Web of Science Citations: 4.
RAJPUT, SARGAM M.; KUMAR, SUGAM; ASWAL, VINOD K.; EL SEOUD, OMAR A.; MALEK, NAVED I.; KAILASA, SURESH KUMAR. Drug-Induced Micelle-to-Vesicle Transition of a Cationic Gemini Surfactant: Potential Applications in Drug Delivery. ChemPhysChem, v. 19, n. 7, p. 865-872, APR 5 2018. Web of Science Citations: 11.
BELTRAN RODRIGUES, ANA CLARA; AFONSO MARIZ, INES DE FATIMA; SENGO MACOAS, ERMELINDA MARIA; TONELLI, RENATA ROSITO; GASPAR MARTINHO, JOSE MANUEL; QUINA, FRANK HERBERT; BASTOS, ERICK LEITE. Bioinspired water-soluble two-photon fluorophores. DYES AND PIGMENTS, v. 150, p. 105-111, MAR 2018. Web of Science Citations: 4.
KOSTAG, MARC; JEDVERT, KERSTIN; ACHTEL, CHRISTIAN; HEINZE, THOMAS; EL SEOUD, OMAR A. Recent Advances in Solvents for the Dissolution, Shaping and Derivatization of Cellulose: Quaternary Ammonium Electrolytes and their Solutions in Water and Molecular Solvents. Molecules, v. 23, n. 3 MAR 2018. Web of Science Citations: 12.
DE JESUS, JESSICA C.; PIRES, PAULO A. R.; SCHARF, MAGDALENA; EL SEOUD, OMAR A. Solvation by aqueous solutions of imidazole-based ionic liquids: 2-A comparison between alkyl and alkoxy side-chains. Fluid Phase Equilibria, v. 451, p. 48-56, NOV 15 2017. Web of Science Citations: 4.
ACHTEL, CHRISTIAN; JEDVERT, KERSTIN; KOSAN, BIRGIT; EL SEOUD, OMAR A.; HEINZE, THOMAS. Dissolution Capacity of Novel Cellulose Solvents Based on Triethyloctylammonium Chloride. MACROMOLECULAR CHEMISTRY AND PHYSICS, v. 218, n. 21 NOV 2017. Web of Science Citations: 6.
SOUZA, GLALCI A.; LANG, ANDRE P.; BAADER, WILHELM J. Mechanistic Studies on the Peroxyoxalate Chemiluminescence Using Sodium Salicylate as Base Catalyst. Photochemistry and Photobiology, v. 93, n. 6, SI, p. 1423-1429, NOV-DEC 2017. Web of Science Citations: 4.
BASTOS, ERICK LEITE; FARAHANI, POORIA; BECHARA, ETELVINO J. H.; BAADER, WILHELM JOSEF. Four-membered cyclic peroxides: Carriers of chemical energy. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, v. 30, n. 9, SI SEP 2017. Web of Science Citations: 11.
FARAHANI, POORIA; BAADER, WILHELM J. Unimolecular Decomposition Mechanism of 1,2-Dioxetanedione: Concerted or Biradical? That is the Question!. Journal of Physical Chemistry A, v. 121, n. 6, p. 1189-1194, FEB 16 2017. Web of Science Citations: 5.
AUGUSTO, FELIPE A.; FRANCES-MONERRIS, ANTONIO; GALVAN, IGNACIO FDEZ; ROCA-SANJUAN, DANIEL; BASTOS, ERICK L.; BAADER, WILHELM J.; LINDH, ROLAND. Mechanism of activated chemiluminescence of cyclic peroxides: 1,2-dioxetanes and 1,2-dioxetanones. Physical Chemistry Chemical Physics, v. 19, n. 5, p. 3955-3962, FEB 7 2017. Web of Science Citations: 12.
DE JESUS, JESSICA C.; PIRES, PAULO A. R.; MUSTAFA, RIZWANA; RIAZ, NAHEED; EL SEOUD, OMAR A. Experimental and theoretical studies on solvation in aqueous solutions of ionic liquids carrying different side chains: the n-butyl-group versus the methoxyethyl group. RSC ADVANCES, v. 7, n. 26, p. 15952-15963, 2017. Web of Science Citations: 7.
FARAHANI, POORIA; OLIVEIRA, MARCELO A.; GALVAN, IGNACIO FDEZ; BAADER, WILHELM J. A combined theoretical and experimental study on the mechanism of spiro-adamantyl-1,2-dioxetanone decomposition. RSC ADVANCES, v. 7, n. 28, p. 17462-17472, 2017. Web of Science Citations: 4.
VAID, ZUBER S.; KUMAR, ARVIND; EL SEOUD, OMAR A.; MALEK, NAVED I. Drug induced micelle-to-vesicle transition in aqueous solutions of cationic surfactants. RSC ADVANCES, v. 7, n. 7, p. 3861-3869, 2017. Web of Science Citations: 12.
FERREIRA, DANIELA C.; BASTOS, GUSTAVO S.; PFEIFER, ANNETT; HEINZE, THOMAS; EL SEOUD, OMAR A. Cellulose carboxylate/tosylate mixed esters: Synthesis, properties and shaping into microspheres. Carbohydrate Polymers, v. 152, p. 79-86, NOV 5 2016. Web of Science Citations: 2.
SOUZA, GLALCI A.; PEIXOTO, MONICA M. M.; SANTOS, ANA P. F.; BAADER, WILHELM J. General Acid and Base Catalysis by Phosphate in Peroxyoxalate Chemiluminescence. CHEMISTRYSELECT, v. 1, n. 10, p. 2307-2315, JUL 1 2016. Web of Science Citations: 3.
KHALID, MUHAMMAD; DE SOUZA, JR., SERGIO P.; BARTOLONI, FERNANDO H.; AUGUSTO, FELIPE A.; BAADER, WILHELM J. Chemiexcitation Efficiency of Intermolecular Electron-transfer Catalyzed Peroxide Decomposition Shows Low Sensitivity to Solvent-cavity Effects. Photochemistry and Photobiology, v. 92, n. 4, p. 537-545, JUL-AUG 2016. Web of Science Citations: 4.
NOVAKI, LUZIA P.; MORAES, EDGAR O.; GONCALVES, ANDRE B.; DE LIRA, RAPHAEL A.; LINHARES, VANESSA N.; DE OLIVEIRA, MARCIA C. K.; MEIRELES, FRANCIS A.; GONZALEZ, GASPAR; EL SEOUD, OMAR A. Solvatochromic and Solubility Parameters of Solvents: Equivalence of the Scales and Application to Probe the Solubilization of Asphaltenes. ENERGY & FUELS, v. 30, n. 6, p. 4644-4652, JUN 2016. Web of Science Citations: 6.
SOUZA, JR., SERGIO P.; KHALID, MUHAMMAD; AUGUSTO, FELIPE A.; BAADER, WILHELM J. Peroxyoxalate chemiluminescence efficiency in polar medium is moderately enhanced by solvent viscosity. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, v. 321, p. 143-150, MAY 1 2016. Web of Science Citations: 5.
BAADER, WILHELM J.; STEVANI, CASSIUS V.; BECHARA, ETELVINO J. H. ``Photo{''} Chemistry Without Light?. Journal of the Brazilian Chemical Society, v. 26, n. 12, p. 2430-2447, DEC 2015. Web of Science Citations: 8.
KHALID, MUHAMMAD; OLIVEIRA, MARCELO A.; SOUZA, JR., SERGIO P.; CISCATO, LUIZ F. M. L.; BARTOLONI, FERNANDO H.; BAADER, WILHELM J. Efficiency of intermolecular chemiluminescence systems lacks significant solvent cavity effect in binary toluene/diphenylmethane mixtures. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, v. 312, p. 81-87, NOV 1 2015. Web of Science Citations: 8.
BARTOLONI, FERNANDO HEERING; DE OLIVEIRA, MARCELO ALMEIDA; MONTEIRO LEITE CISCATO, LUIZ FRANCISCO; AUGUSTO, FELIPE ALBERTO; BASTOS, ERICK LEITE; BAADER, WILHELM JOSEF. Chemiluminescence Efficiency of Catalyzed 1,2-Dioxetanone Decomposition Determined by Steric Effects. Journal of Organic Chemistry, v. 80, n. 8, p. 3745-3751, APR 17 2015. Web of Science Citations: 19.
WILHELM J. BAADER; CASSIUS V. STEVANI; ETELVINO J. H. BECHARA. "Photo" Chemistry Without Light?. Journal of the Brazilian Chemical Society, v. 26, n. 12, p. -, Dez. 2015.

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