QUÍMICA VERDE: TÉCNICAS AVANÇADAS DE EXTRAÇÃO ISEP, … de resumos Workshop - 1QV.pdf · QUÍMICA VERDE: TÉCNICAS AVANÇADAS DE EXTRAÇÃO – ISEP, 22 de fevereiro de 2018

QUÍMICA VERDE: TÉCNICAS AVANÇADAS DE EXTRAÇÃO – ISEP, 22 de fevereiro de 2018 1


1º WORKSHOP

QUÍMICA VERDE:

TÉCNICAS AVANÇADAS DE EXTRAÇÃO Os processos de extração são largamente utilizados em meio industrial, tendo importantes aplicações nos sectores alimentar, cosmético, farmacêutico, petrolífero e químico, bem como noutras áreas, tais como a artística. Os seus impactos ambientais são geralmente significativos, pois para além de requererem o uso de elevadas quantidades de solventes orgânicos, estima-se que consumam cerca de 50% da energia envolvida no processo produtivo. Os métodos tradicionais de extração não cumprem, por isso, os princípios fundamentais da Química Verde, altamente focada na redução do uso de solventes, de forma a minimizar os impactos ambientais sem comprometer a eficiência e os custos de produção. Neste contexto, tem crescido o interesse na procura de métodos de extração mais verdes e sustentáveis, sendo este um tema de investigação multidisciplinar nas áreas da química aplicada, biologia e tecnologia. Este workshop pretende apresentar e discutir a utilização de tecnologias emergentes na extração seletiva de compostos, priorizando os princípios da Química Verde. O programa de trabalho abrange os mais recentes avanços nas principais técnicas de extração verde, bem como os seus princípios de funcionamento e aplicações. Serão aceites resumos para apresentação em poster (80 x 100 cm). Os participantes interessados poderão também trazer as suas amostras para extração por microondas, na sessão prática desenvolvida pela QLABO.

Informações: www.isep.ipp.pt/Page/ViewPage/TecnicasExtracao

Comissão Organizadora: Ana P. Carvalho César Oliveira Clara Grosso Cristina Delerue-Matos M. Fátima Barroso Maria João Ramalhosa

Valor da inscrição: Estudantes de licenciatura e mestrado: 10€ Estudantes de doutoramento e pós-doutoramento: 20€ Outros: 50€ Todas as inscrições incluem almoço.

Datas importantes: Submissão de resumos: 12 de fevereiro Aceitação de resumos: 14 de fevereiro Inscrição: 16 de fevereiro

http://www.isep.ipp.pt/Page/ViewPage/TecnicasExtracao



RESUMOS E

NOTAS BIOGRÁFICAS


ELECTROTECHNOLOGIES

AS AN ALTERNATIVE GREEN EXTRACTION METHOD

António Vicente

Departamento de Engenharia Biológica, Escola de Engenharia, Universidade do Minho

[email protected]

The utilization of cost-effective, mild, sustainable and low energy consumption techniques in

downstream processes, and in extraction processes in particular, is vital to ensure an

economically and environmentally sustainable process. However, the preservation of the

integrity and functionality of the compounds of interest is still a great challenge. In this regard,

electrotechnologies are a promising option that might have a significant role to overcome some

of these challenges.

These technologies are based on the application of external electric fields and are categorized

according to specific operational features such as the nature of the electric flow, the electric

field strength and extension of heat dissipation. These different features result in different

impacts on treatment temperature, cell viability, permeability and structural integrity among

other characteristics of treated cells. Electrotechnologies based on the effects of pulsed

electric fields (PEF), ohmic heating (OH) and its moderate electric fields (MEF), high voltage

electric discharge (HVED) and direct current (DC) electric field, have gained continuously

growing interest as very promising tools to improve extraction yields, both in quality and

quantity.

mailto:[email protected]


NOTA CURRICULAR

ANTÓNIO VICENTE

António Vicente é Engenheiro Alimentar (1994) pela Escola Superior de Biotecnologia da

Universidade Católica Portuguesa, no Porto (Portugal), Doutor em Engenharia Química e

Biológica (1998) pela Universidade do Minho, Braga (Portugal) e Agregado em Engenharia

Química e Biológica (1998) pela Universidade do Minho, Braga (Portugal).

Desde o Doutoramento que trabalha em tecnologia de fermentação, nomeadamente no

desenho e operação de reatores biológicos para obtenção de bioetanol e produtos de elevado

valor acrescentado a partir de subprodutos da indústria alimentar. Tem também dedicado a

sua atividade de investigação a temas relacionados com a Indústria Alimentar,

nomeadamente novas tecnologias de processamento térmico (campos elétricos

moderados/aquecimento óhmico, onde tem estudado o efeito da corrente elétrica em

biomoléculas), revestimentos comestíveis para produtos alimentares (queijos, frutos,

legumes, pescado...) e nanotecnologia aplicada a sistemas alimentares. Tem publicados mais

de 200 artigos em revistas internacionais com a avaliação plena, cerca de 25 capítulos em

livros de circulação internacional, 4 patentes e é editor de quatro livros científicos.

Orientou/orienta 16 investigadores pós-Doutorados, 25 trabalhos de Doutoramento, e cerca

de 35 trabalhos de Mestrado.

Tem sido uma prioridade a manutenção de um contacto muito próximo com a indústria, tendo

estado envolvido em vários projetos de investigação nacionais e internacionais, juntamente

com parceiros industriais, tanto como participante como coordenador.

Atualmente, é Professor Associado com Agregação, Diretor do Departamento de Engenharia

Biológica e Investigador do Centro de Engenharia Biológica da Universidade do Minho, em

Braga (Portugal).


USE OF EMERGING TECHNOLOGIES

FOR IMPROVED AND GREENER EXTRACTION PROCESSES

Jorge Saraiva

Research Unit of Organic Chemistry, Natural and Agro-food Products (QOPNA), Chemistry

Department, University of Aveiro, Aveiro, Portugal

[email protected]

Extraction is the first step for the recovery (isolation and purification) of important bioactive

components present in natural materials, and it can be described as a mass transport

phenomenon where solids present in a plant matrix are transferred into the solvent up to their

equilibrium concentration. The growing interest about bioactive compounds and high added

value ingredients from several different matrixes is related to the consumer preference of

natural additives and antioxidants over the synthetic ones. The major problem is that those

bioactive compounds, such as flavonoids, anthocyanins, etc., are enclosed in insoluble

structures, making its extraction very complicate. Many organic compounds in plant/herbal

material are heat-sensitive, losing integrity and biological activity by denaturation when

subjected to heat. The most used extraction techniques are the conventional ones, such as

Soxhlet, heat reflux, agitation, boiling, and distillation. Although these methods are easy to

perform and cheap to operate, they are mostly based on the choice of one correct solvent, the

use of mild/high temperatures (that causes thermal degradation) and agitation in order to

increase the solubility of materials and the mass transfer rate, being reflected on long

extraction times, high costs, and low extraction efficiency. For so, it is of great interest to

develop new extraction methods, such as high pressure, pulsed electric fields, ultrasounds,

and supercritical fluids (mostly CO2) assisted extractions. These technologies are considered

environmentally friendly; allow the use of lower amounts of organic solvents and the reduction

in extraction time and energetic consumption, conducting to higher yields and high quality and

bioactivity final extracts.



NOTA CURRICULAR JORGE SARAIVA

Jorge Saraiva é Licenciado em Bioquímica pela U. de Coimbra e Doutorado em Biotecnologia

(Ciência e Engª. Alimentar) pela U. Católica (Porto). É atualmente Investigador Auxiliar no

Dep. de Química da Universidade de Aveiro (Unidade de Investigação de Química Orgânica,

Produtos Naturais e Agroalimentares - QOPNA), onde é coordenador da Plataforma

Tecnológica Multidisciplinar Alta Pressão (https://www.ua.pt/ptaltapressao/) e Diretor da

Licenciatura em Biotecnologia.

A sua atividade de investigação centra-se em Tecnologias de Processamento e Conservação

de Alimentos, particularmente em novos processos de Conservação, com enfoque em

tecnologias emergentes, como pasteurização a frio por alta pressão visando garantir a

Segurança Alimentar a nível microbiológico, com melhor qualidade dos alimentos em termos

sensoriais, nutricionais e organoléticos. Nos últimos anos tem explorado novas aplicações de

tecnologias emergentes como a extração a frio de compostos bioativos de várias fontes

naturais.

Leciona Tecnologia Alimentar e Biocatalisadores no Mestrado em Biotecnologia, entre outras

disciplinas.

É membro eleito do Comité do European High Pressure Research Group (EHPRG) e membro

do Conselho Científico do Clube de Produtores do Continente (Grupo Sonae) e do Conselho

Consultivo do INOVLINEA do Tagusvalley - Tecnopolo do Vale do Tejo.

Para mais informação bibliográfica:

http://orcid.org/0000-0002-5536-6056; http://www.researcherid.com/rid/C-2996-2009;

Scopus Author ID: 35583570500; https://www.researchgate.net/profile/Jorge_Saraiva/stats/;

https://aveiro.academia.edu/JorgeSaraiva;

http://scholar.google.pt/citations?user=2Dg9WVQAAAAJ&hl=en

https://www.ua.pt/ptaltapressao/

http://orcid.org/0000-0002-5536-6056

http://www.researcherid.com/rid/C-2996-2009

http://www.scopus.com/inward/authorDetails.url?authorID=35583570500&partnerID=MN8TOARS

https://www.researchgate.net/profile/Jorge_Saraiva/stats/

https://aveiro.academia.edu/JorgeSaraiva

http://scholar.google.pt/citations?user=2Dg9WVQAAAAJ&hl=en


SUBCRITICAL WATER EXTRACTION

AN EMERGING TECHNIQUE

Jaroslava Švarc-Gajić

Faculty of Technology, Department for Applied and Engineering Chemistry,

University of Novi Sad, Serbia

[email protected]

Hot compressed water can be used both as an excellent solvent and as a reactive medium. In

its near-critical and critical (374C, 218 atm) state water becomes very reactive potentiating

numerous chemical reactions, such as oxidation, hydrolysis, isomerisation, condensation

hydrogenation/dehydrogenation, alkylation, and others. High reactivity of hot compressed

water can be exploited in chemical synthesis, remediation, waste destruction, plastic recycling

and biofuel production. Different added-value compounds, such as organic acids, aminoacids,

sugars, phenolic monomers, fatty acids, and other, can be produced from organic waste by

hot compressed water. By sequential hydrothermal extraction technology, multiple benefits

can be achieved in cascading approach of waste treatment.

As an extraction solvent subcritical water is used under milder conditions, below it`s critical

point, representing excellent alternative to organic solvents owing to its excellent selectivity,

efficiency, safety, low price and green character. The selectivity of subcritical water can be fine

tuned by changing operational parameters. With water heating it`s dielectric constant

decreases, becoming selective towards moderately polar compounds. In addition, heating

decrease it`s viscosity, surface tension and density, contributing further to extraction efficiency.

Modifiers added to subcritical water usually serve to make required operational parameters

milder and to modify sample matrix. Sodium dodecyl sulphate, e.g., is added as a micelle-

forming compound to allow extraction of non-polar compounds, such as PAHs, whereas acids

and chelating compounds are used for efficient extraction of metals.

Research demonstrate that bioactivity of plant extracts obtained by subcritical water is better

in comparison to extracts obtained by other extraction techniques, indicating specific chemical

composition. Extracts of agricultural and food industry by-products, such as leaves, seeds,

skin, stems, etc. demonstrate anti-oxidant, antilipidemic, anti-diabetic, neuroprotective, anti-

aging and other effects, offering wide array of applications. Chemical analysis of these extracts

suggests the presence of both naturally-occurring and neo-formed compounds. The field of

application of subcritical water is vast still requiring thorough research.



NOTA CURRICULAR

JAROSLAVA ŠVARC-GAJIĆ

Prof. Jaroslava Švarc-Gajić teaches at the Faculty of Technology, University of Novi Sad,

courses related to instrumental analysis, sample preparation and toxicology.

During her professional development, she developed numerous analytical methods, including

electroanalytical, chromatographic and optical, for trace analysis and quality control of

environmental samples, food, pharmaceutical and cosmetic products.

Her current research interest is oriented towards exploitation of subcritical water in different

applications including extraction and decomposition processes, isolation and characterisation

of natural bioactive compounds.

As a single author she published 6 international scientific books and monograph publications

related to bioactivity of natural compounds, sample preparation in analytical chemistry and

toxicology; two nationals, and was the editor of two international scientific books. In addition,

she is an author of more than 180 scientific publications related to instrumental analysis,

chemistry and bioactivity of natural compounds, food and pharmaceutical analysis.


ASE - ACCELERATED SOLVENT EXTRACTION:

A NEW APPROACH FOR SOLVENT EXTRACTIONS METHODS

Daniel Ettlin and Jorge Alves

Unicam Sistemas Analíticos Lda.

[email protected]

The traditional solvent extractions methods, like Soxhlet, are well-established methods, and

used in general for extraction of target or untargeted compounds in different solids materials,

as food, soil, plants, etc. The increase of pressure to achieve higher temperatures extraction

is a way to make any reaction faster. This same thermodynamic principle is used on the

Thermo Scientific solvent accelerated extractor. Using organic acids and aqueous solvents or

acids and bases at high temperatures and pressures, the Thermo Scientific™ Dionex™ ASE™

Accelerated Solvent Extraction system extracts compounds from solid and semi-solid samples

quickly with small solvent volume.

The usage of less solvent is an environmental concern for all the conscious and responsible

citizens and analytical chemist are no exception on working towards greener chemistry. It will

save time, solvent, and money, and generate results in a fraction of the time compared to

traditional techniques such as Soxhlet or sonication.

We will present a workflow for extraction using state of the art technology for faster, cleaner

and more effective extraction of organic compounds on solids. On a similar base of the

accelerated solvent extraction principles, we can use as an alternative microwave radiation as

a source of energy. Providing the temperature and pressure increase is achieved, we can

obtain faster and more effective extractions with a high yield. Using the fore mentioned

principle of microwave irradiation and consequent heating, some extractive systems for

Essential Oils have been designed. On these cases, the purpose is even more ambitious, as

using no solvent at all, and achieve extractions faster and with high yield. Microwaves can

better penetrate plant material, and disrupt cells on a more effective way. We will briefly

introduce systems that can extract aroma, flavours and essential oils in lab, and pilot scale,

with the objective to scale up to small industrial units.



NOTA CURRICULAR

DANIEL ETTLIN JORGE ALVES

Pharmacist

MBA (LSU)

Presently CEO and Product Manager for

Thermo Unicam Portugal

25 years’ experience in Scientific

Instrumentation, on Spectrometry and

Chromatography, Microwave Digestion and

Extraction Systems.

In charge of user training in different areas

of scientific instrumentation, and follow up

on Method development.

He was part of the Instrument development

advisor team of Unicam (Cambridge) for the

Molecular and Atomic absorption

instruments, and PM for those lines in Spain

and Portugal.

He worked previously in the Pharmaceutical

Industry on Production and on Product

development.

https://www.linkedin.com/in/danielettlin/

Pharmaceutical Chemist

Master in UP

Presently the Product Manager for HPLC

and IC at Thermo Unicam Portugal

4 years’ experience in Scientific

Instrumentation, specifically on HPLC and

Ion Chromatography.

In charge of user training in

Chromatography, and follow up on Method

development.

https://www.linkedin.com/in/jorge-alves-

269aa158/

https://www.linkedin.com/in/danielettlin/

https://www.linkedin.com/in/jorge-alves-269aa158/

https://www.linkedin.com/in/jorge-alves-269aa158/


SOLID PHASE EXTRACTION (SPE):

AN EXTRACTION METHOD SIMPLE, FASTER, CLEANER ...

AND GREENER?

Xavier Rodríguez Piró

Waters Corporation

[email protected]

Solid phase extraction (SPE) is a widely used technique in analytical chemistry. It is often

considered as one of the best options available to reduce the complexity of a sample matrix

while preserving and concentrating the analyte(s) of interest.

The benefits of SPE also include lower matrix factors and higher, more reproducible recoveries

and results. However, due to its perception of being time consuming, costly, and complicated,

SPE is often the last option selected.

In this presentation we will show the advances made in recent years by Waters to make SPE

a simpler, faster and cleaner technique. As a consequence of these advances SPE has also

become a greener technique.



NOTA CURRICULAR

XAVIER RODRÍGUEZ PIRÓ

Xavier has been working in the chromatography industry for almost two decades and has been

with Waters Corporation since 1999.

In the last decade, he has specialised in sample preparation, mainly in SPE and now serves

as a business development manager.

In his role, he works with customers to understand their sample prep challenges and helps

address them with Waters products. He is also responsible for delivering educational seminars

on sample preparation topics.


ASE: EXTRACCIÓN ACELERADA CON DISOLVENTES PRESURIZADOS

Y A ELEVADA TEMPERATURA

C. Pérez Llaguno; F. Macías

Laboratorio de Tecnología Ambiental. Instituto de Investigaciones Tecnológicas

Universidade de Santiago de Compostela

[email protected]

La preparación de muestras para análisis por Cromatografía líquida, cromatografía de gases,

IR y otras técnicas espectroscópicas es el paso clave en el proceso analítico de un gran

número de sustancias y suele necesitar demasiadas etapas y horas de trabajo. La capacidad

de integrar el pretratamiento, la extracción y la purificación es crítica para la productividad

total, reducir el manejo de muestra y disminuir el tiempo dedicado a la preparación de muestra.

Esto puede conseguirse con un equipo de Extracción Acelerada con Disolventes (ASE), un

método eficiente, de elevada reproductibilidad, que garantiza un menor consumo de

disolventes (unos 15 ml/10 gramos de muestra, frente a los 500 m de un Soxhlet), menor

generación de disolventes residuales y mayor rapidez (generalmente de 10 a 20 minutos para

una o varias muestras). La extracción se realiza con disolventes convencionales (agua,

hexano, ...) a temperatura superiores a las de ebullición del disolvente (normalmente de 30 a

200ºC) y a presiones elevadas (hasta 140 atmósferas). El preciso control de la temperatura

de la celda de extracción proporciona una excelente reproducibilidad y el alto nivel de

automatización aumenta la productividad del laboratorio. Tiene aplicación para la

determinación de contaminantes orgánicos (COV, PCB, PAH, dioxinas, pesticidas, …),

agentes tensioactivos, alimentos, productos farmacéuticos, polímeros, y, en general cualquier

sustancia que pueda ser extraída por métodos de Soxhlet, ultrasonidos o microondas. Su

principal desventaja es el coste de los equipos.



NOTA CURRICULAR

FELIPE MACÍAS

Profesor de la Universidad de Santiago de Compostela en materias de Ciencias de la Tierra.

Catedrático de Universidad del Depto. de Edafología y Química Agrícola de la Facultad de

Biología en la USC desde 1984.

Actividad Académica

Coordinador del curso de Doctorado «Medio Ambiente y Recursos Naturales». (Mención de

calidad MCD2006-00169). 1986-2008; Director General de la Agencia de Calidad Ambiental.

Consellería de Ordenación del Territorio. Xunta de Galicia. 1989-90; Profesor de cursos de

master y doctorado en las Universidades de Santiago, Murcia, Oviedo, Nancy, París, Rennes,

Sao Paulo, Minho y Vigo. 1990-...; Presidente de la Sociedad Española de Ciencia del Suelo

(Febrero 2001-2009).

Miembro del “Working Group on Research” de la Estrategia Europea de Suelos (en

representación del Ministerio de Medio Ambiente). 2002-2006; Coordinador del grupo de

investigación GI-1245 “Cartografía de suelos y paisajes, físico-química, degradación y

recuperación de suelos y aguas”. Máximo nivel de excelencia de la Xunta de Galicia. (2004-

2016); Membre étranger de l’Academie d’Agriculture de France. Agriculture, Alimentation et

Environnement (séction Physique et Chimie des milieux et des êtres vivants). Elegido en

votación de diciembre 2005; Coordinador del grupo de Suelos y Biogeoquímica para la

reforma de los hábitats de la Red Natura Española y el seguimiento de su calidad.

MINISTERIO DE MEDIO AMBIENTE. 2006-2009.

Actividad investigadora

Autor de más de 250 publicaciones en temas de Ciencia del Suelo, Biogeoquímica de

sistemas superficiales (suelos, aguas y hábitats), Evaluación y Planificación de Recursos

Naturales, Suelos Contaminados, Recuperación de Suelos, Aguas y Ecosistemas, Evaluación

de Impactos y Riesgos Ambientales, Secuestro de Carbono, ...

Investigador principal de más de 100 proyectos de investigación financiados por

administraciones y empresas y director de 31 tesis doctorales.


NOTA CURRICULAR

CARMEN P. LLAGUNO

Técnico Especialista (Modulo III) en Salud Ambiental y Técnico Superior en Química

Ambiental (IFP Nº1 Oviedo-IES Santiago).

Técnico de apoyo a la Investigación en la Universidad de Santiago de Compostela desde

2001.

Actividad Profesional-Investigadora

1994: Analista en el Laboratorio COGERSA (CONSORCIO de GESTION de RESIDUOS

URBANOS) y gestor de RTP´s en el Principado de Asturias. Posteriormente paso a formar

parte de los técnicos de Salud Pública para el control de aguas potables y de uso público

dependiendo de la Consejería de Fomento del Principado de Asturias. 1996-1998: Técnico de

Medio Ambiente en el Ayuntamiento de Avilés (Primera Ciudad en España proclamada como

Ciudad de Atmósfera Contaminada,) y con protocolo para la seguridad del Aire y la

Ciudadanía. Desde el 2001 y hasta la actualidad, he estado en diversos proyectos, formando

parte del grupo de Investigación GI-1245 Coordinado por el Dr. Felipe Macías Vázquez. En

este periodo destaca 2007-2011. Beca Isabel Barreto para Tecnólogos, otorgada por la

Consellería de Innovación e Industria. Xunta de Galicia. Desde el 2012 y hasta la actualidad,

ejerciendo de Responsable de Laboratorios Coordinados por F. Macías Vázquez.

Participación en diversas Reuniones y Congresos, entre otros: Conferencia Internacional de

Minería Sostenible, Comunicación escrita: “Recuperación aguas ácidas de la mina de Touro

mediante sistemas integrados de barreras reactivas con diferentes tecnosoles y humedales”

Coautora en los libros “Metales Pesados, Materia Orgánica y otros Parámetros de la capa

Superficial de los Suelos Agrícolas y de Pastos de la España Peninsular”. Resultados globales

y por Provincias. Ministerio de Medio Ambiente, Ministerio de Educación y Ciencia y Ministerio

de Agricultura, Pesca y Alimentación.

Colaboradora en múltiples artículos publicados en distintas revistas entre otros: “Molecular

characterization of Ulex europaeus biochar obtained from laboratory heat treatment

experiments – A pyrolysis–GC/MS study”, Journal of Analytical and Applied Pyrolysis, 2012,

95:205-212.


THE NEW LEADING EDGE OF SAMPLE PREPARATION

Duarte Ventura e João Nogueira

QLABO – Equipamentos de Laboratório e Serviços, Lda.

[email protected]



NOTA CURRICULAR

DUARTE VENTURA JOÃO PEDRO NOGUEIRA

Duarte Ventura

Formação em Engenharia Química

De 1989 a 2006 desenvolveu a sua

atividade profissional na Industria de

Celulose e Papel na vertente Técnico-

Comercial em Produtos Químicos e

Assistência Técnica; empresas:

GraceDearborn/Betz/Hercules atual

Solenis/Enkrott/BimKemi;

De 2007 a 2015 desenvolveu a sua

atividade profissional na Área das Energias

Renováveis na vertente Técnico-Comercial;

Empresa: Energie EST, Lda;

Desde 2015 desempenha funções na

QLABO – Equipamentos de Laboratório

e Serviços, Lda. na vertente Técnico-

Comercial na zona Norte/Centro.

João Pedro da Silva Nogueira

Licenciado em Biologia no ramo Científico -

Tecnológico pela Faculdade de Ciências da

Universidade do Porto. Mestre em Inovação

e Empreendedorismo Tecnológico pela

Faculdade de Engenharia da Universidade

do Porto.

Possui longa experiência em investigação

laboratorial. Tem diversas formações

complementares em áreas Tecnológicas,

Científicas e Empresariais. Ampliou o seu

espectro de conhecimentos através de

formação certificada em Gestão da

Qualidade e Auditorias Internas: ISO 9001:

2015 e ISO 19011: 2012, NP ISO 31000:

2013 e Gestão da Qualidade Total.

Atualmente, na QLABO – Equipamentos

de Laboratório e Serviços, Lda. atua na

área Técnico-Comercial na região norte de

Portugal, desde 2016.


HARNESSING AQUEOUS BIPHASIC SYSTEMS

AS AN EFFICIENT PLATFORM TO SEPARATE POLLUTANTS

AND VALUE ADDED CHEMICALS

María S. Álvarez1,2, Lois Morandeira1, Noel Escudero1, Neusa Pinheiro1,3, Ana

Rodríguez1, M. Ángeles Sanromán1, Francisco J. Deive1*

1Department of Chemical Engineering, University of Vigo, Vigo, 36310, Spain; 2Department of

Chemical and Biological Engineering, School of Engineering and Applied Science, Princeton

University, New Jersey, 08544, United States of America; 3Department of Chemical

Engineering, Faculdade de Engenharia e Ciências do Mar, Campus da Ribeira de Julião, 163

Mindelo

*Presenting author: [email protected]

During the last years, a reviving interest on the development of novel Aqueous Biphasic

Systems (ABS) has been detected. The main reason for that is placed on the possibility of

designing neoteric systems due to the existence of solvents like ionic liquids. These salts have

been called to replace the conventional organic solvents and they are expected to prevent

pollution and increase safety due to their special characteristics like their thermal stability,

negligible volatility, non-flammability, and high ability to dissolve a wide range of organic,

inorganic and polymeric compounds [1].

All these properties mark the onset of the interest in these molten salts, with at least one million

simple ILs that can be easily prepared in the laboratory, although up to date only about 300

ILs are commercialized [2]. In this sense, the selection of a particular combination of a cation

and an anion, strongly influences the physical and chemical properties and reactivity, thus

controlling the outcome of a specific process. This advantage, also named tuneability, is the

innovative breakthrough that ILs have posed in the field of chemistry and chemical

engineering, and made them to be christened “designer” solvents [2].



Actually, the pioneering work of Rogers and collaborators [3], reporting the ability of ionic

liquids to be salted out in aqueous solutions by high charge density inorganic salts, has opened

up an inconceivable array of extraction opportunities [4]. Thus, different ionic liquids, most of

them belonging to imidazolium family were the subject of many research works, while the use

of aqueous solutions of special polymeric compounds like surfactants has been barely

explored.

On the basis of these facts, in our research group we have demonstrated the ability of inorganic

and organic salts (including molten salts) to trigger phase segregation in aqueous solutions of

non-ionic surfactants commonly employed in biotechnological processes like Triton and Tween

families. After characterizing the phase separation ability, these systems have been applied

for the remediation of different pollutants, both hydrophobic and hydrophilic. Additionally, they

have been employed in downstream operations in biotechnological processes. In this sense,

we are now researching new biocompatible ionic liquids based on aminoacid anions and

choline cation to be implemented in extraction processes for obtaining antioxidant

biomolecules from microalgal biomass.

Acknowledgements: The authors thank Spanish Ministry of Economy and Competitivity for

funding through the project RyC-2013-14225, ED431F 2016/007. M.S.A. thanks Xunta de

Galicia for her postdoc grant (EDB481B2016/140-0).

References

[1] F. J. Deive, A. Rodriguez, A. B. Pereiro, J. M. M. Araujo, M.A. Longo, M. A. Z. Coelho, J.

N. Canongia Lopes, J. M. S. S. Esperanca, L. P. N. Rebelo, I. M. Marrucho Ionic liquid-based

aqueous biphasic system for lipase extraction, Green Chem. 13 (2011) 390-396.

[2] Plechkova, N. V., Seddon, K. R., Applications of ionic liquids in the chemical industry.

Chem. Soc. Rev. 37 (2008) 123-150.

[3] K.E. Gutowski, G.A. Broker, H.D. Willauer, J.G. Huddleston, R.P. Swatloski, J.D. Holbrey,

R.D. Rogers, Controlling the aqueous miscibility of ionic liquids: aqueous biphasic systems of

water-miscible ionic liquids and water-structuring salts for recycle, metathesis, and

separations, J. Am. Chem. Soc. 125 (2003), 6632-6633.

[4] M.G. Freire, A.F.M. Claudio, J.M.M. Araújo, J.A.P. Coutinho, I.M. Marrucho, J.N. Canongia

Lopes, L.P.N. Rebelo, Aqueous biphasic systems: a boost brought about by using ionic liquids,

Chem. Soc. Rev. 41 (2012) 4966-4995.


NOTA CURRICULAR

FRANCISCO JAVIER DEIVE HERVA

Assist. Prof. Dr. Deive has two degrees in Chemistry and Chemical Engineering from the

Universities of Vigo and Santiago de Compostela (Spain).

He received his PhD in Chemical Engineering in 2007 at the University of Vigo after defending

his PhD thesis focused on the isolation, characterization and production of industrially relevant

enzymes from extremophilic microorganisms. Afterwards, he started his posdoc period at the

Instituto de Tecnología Química e Biologica of Lisbon (Portugal), focused on the introduction

of a group of neoteric solvents, ionic liquids, for the extraction of metabolites with industrial

interest.

In general, he has participated in about 30 research projects (more than 2.0 M€), at an

international, national and regional level. His 74 articles in top-ranked journals and 6 book

chapters (h Index =19) include publications in the areas of antioxidants extraction,

development of bioprocesses with lower environmental impact and contaminants remediation.

He has supervised 2 postdoctoral researchers, 6 PhD and 16 MSc students. He is currently

Member of the Editorial Board of the Journal Enzyme Engineering and the Journal of

Chemistry, and he participates in the Evaluation Boards of different research agencies (e.g.

Chile, Argentina, Spain, etc.).

Links of interest:

http://orcid.org/0000-0001-6781-4082

https://www.researchgate.net/profile/Francisco_Deive_Herva

http://orcid.org/0000-0001-6781-4082

https://www.researchgate.net/profile/Francisco_Deive_Herva


MICROEXTRACTION TECHNIQUES

- HOW SIMPLE CAN WE GO?

J.M.F. Nogueira

Centro de Química e Bioquímica e Centro de Química Estrutural, Faculdade de Ciências,

Universidade de Lisboa, 1749-016 Lisboa, Portugal.

[email protected]

The modern microextraction techniques run towards great simplification, miniaturization, easy

manipulation of the analytical devices, strong reduction or absence of organic toxic solvents

and, low sample-volume requirements in agreement with the green analytical

chemistry principles [1]. For trace analysis, the sorption-based methods have demonstrated to

be the best choice, enabling direct microextraction, mainly of volatile and semi-volatile

compounds, from almost all types of samples, including gaseous, liquid and even solid

matrices. These analytical approaches have high throughput to enhance selectivity and

sensitivity prior the application of chromatographic or hyphenated systems [2].

Nowadays, some well-established examples are the passive liquid-based microextraction

techniques, such as dispersive liquid-liquid microextraction (DLLME), single-drop

microextraction (SDME) and hollow fibber liquid-phase microextraction (HF-LPME). On the

other hand, passive solid-based microextraction or sorption-based techniques have also been

proposed as effective alternatives for trace analysis, like solid phase microextraction (SPME),

stir bar sorptive extraction (SBSE) and, more recently, bar adsorptive microextraction (BAμE)

[3]. Despite all of this, one cannot simply use a single technique as a universal approach, but

the most suitable technique should be selected according to the target analytes and matrix

involved. Furthermore, some of these techniques are neither user-friendly, eco-friendly or cost-

effective nor suitable for the routine work. In general, the liquid-based microextraction

approaches (i.e. DLLME, SDME and HF-LPME) present fast kinetics, use very simple

apparatus and are costly-effective. On the other hand, the solid-based microextraction


https://www.sciencedirect.com/science/article/pii/S016599361500165X#bib0015


techniques (i.e. SPME, SBSE and BAμE) are easier to manipulate, more environmental-

friendly, allow automation although need a back-extraction stage, which is not attractive since

requires time-consuming steps particularly if liquid desorption (LD) is implemented.

Furthermore, this drawback is more pronounced if reusable devices are adopted, making the

LD the limitative stage. For all these reasons, novel ideas and concepts are welcome,

especially if using simple analytical strategies.

In this contribution, the main advantages and limitations of the most used microextration

techniques will be discussed, as well as proposing simple concepts using eco-user-friendly

and cost-effective approaches that simultaneously could be dedicated for the routine work

[4,5].

Acknowledgements: The author wishes to thank Fundação para a Ciência e a Tecnologia

(Portugal) for financial support (Project: UID/MULTI/00612/2013).

References:

[1] J.M.F. Nogueira, TrAC, 2015, 71, 214-223.

[2] J.M.F. Nogueira, Anal. Chem. Acta, 2012, 757, 1-10.

[3] N.R. Neng, A.R.M. Silva, J.M.F. Nogueira, J. Chromatogr. A, 2010, 1217, 7303-7310.

[4] A. Ide, J.M.F. Nogueira, J. Pharm. Biomed. Anal., 2018, in press

[5] A. Ide, J.M.F. Nogueira, Anal. Bioanal. Chem., 2018, in press


NOTA CURRICULAR

J.M.F. NOGUEIRA

Dr. J.M.F. Nogueira (b. 1965) is Associate Professor at the Faculty of Sciences of the

University of Lisbon (UL), Lisbon (Portugal). In 1990, he received a degree in Chemistry and

a PhD in Analytical Chemistry (UL) in 1995.

He worked several months at the Research Institute for Chromatography and University of

Gent (Belgium) during his PhD project. Currently, he is researcher at the Centre of Chemistry

and Biochemistry (UL) and head of the Separation Science & Technology group.

His main research activity focuses on the development and application of innovative analytical

methodologies involving chromatographic, electromigration and hyphenated techniques. In

this context, the development of novel analytical approaches, with emphasis to the modern

sorption-based microextraction techniques, point out the main research activities in areas such

as environment, water, food, phytochemistry, natural products, etc.

He is author and co-author of dozens of peer-reviewed articles (h-index: 34) and chapters of

international books, as well as supervisor of academic graduation and post-graduation projects

and referee in international scientific journals. In 1999, he founded the Chromatography group

of the Portuguese Chemical Society being president during several years.

He has been chairman and co-chairman of national and international meetings on

chromatography, as well as invited to be chairperson and speaker in scientific sessions. Now,

he is the Portuguese representative of the European Society for Separation Science.


SUPERCRITICAL CARBON DIOXIDE EXTRACTION

Manuel Nunes da Ponte

LAQV@REQUIMTE, Departamento de Química

Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Caparica

[email protected]

Supercritical fluids are gases at conditions sufficiently close to the vapour-liquid critical point

to show “abnormally” high dependency of density on pressure and temperature. Extraction

with a supercritical solvent is carried out in a high pressure extractor, where high density

ensures higher solvent power, and separation of solutes from the solvent is carried out in a

lower pressure vessel, where solvent density is sufficiently low to induce solute deposition.

The most characteristic advantage of using a supercritical fluid in an extraction process is

therefore the ability to implement the separation step, in principle, by a simple pressure drop

and/or temperature increase. Another advantage is that the physical properties of supercritical

fluids, such as diffusivity and viscosity, allow higher mass transfer rates than for liquid

extraction.

Carbon dioxide is the best known supercritical solvent due to its applications in food and natural

product extraction. CO2 is a poor solvent of most substances, which means that the solvent-

to-solute ratio in supercritical CO2 extraction is necessarily very high. On the other hand,

extremely selective extractions may be carried out, where only one or a few target compounds

are actually removed from a complex matrix. This makes supercritical CO2 extraction especially

attractive for cleaning, that is, removing unwanted substances from a product.

Some of the largest-scale applications are of this type: the first one, decaffeination of coffee,

and ScCO2 most recent success, removal of wine cork-tainting odour from cork. In these

cases, the widespread notion that supercritical fluid extraction is expensive and only applicable

to high value-added products is certainly not valid. Many economically viable processes have

been devised and they are being used worldwide. On the contrary, in cases where the extract



is the product, economic viability is much more dependent on the added value. Superior quality

to alternative extraction processes is sometimes the case, as solvent contamination is not an

issue, and moderate temperatures are used. Hops extraction for brewery, another large-scale

application, is a good example.

Carbon dioxide is currently perceived by the general public as a persistent pollutant, due to the

increased awareness of the greenhouse effect on climate. Paradoxically, this change of image,

from innocuous solvent to dangerous pollutant, will enormously stimulate carbon dioxide

utilisation. As plans for CCS – carbon capture and storage – develop in the next decades as

an indispensable technology for climate change mitigation, pure high-pressure carbon dioxide

will become available at very low prices. Supercritical CO2 extraction has a bright future.


NOTA CURRICULAR

MANUEL NUNES DA PONTE

Professor of Physical Chemistry at NOVA (New University of Lisbon), Portugal.

Born in Goa, India, in 1949; Portuguese nationality; PhD (1977) in Chemical Engineering /

Technical University of Lisbon. Visiting student, Oxford University (1975-76), and Visiting

Associate Professor, Cornell University (1983/84).

His research interests are focused on applications of Supercritical Carbon Dioxide, and, more

recently, Ionic Liquids, to separation and chemical reaction (http://orcid.org/0000-0003-4499-

4521)

Director of ITQB/NOVA, one of the largest research institutes in Portugal, from1999 to 2002.

Chairman of the EUREKA Initiative High Level Group during the 2008/09 Portuguese

Chairmanship.

Recently founded the start-up Zeyton Nutraceuticals.

http://orcid.org/0000-0003-4499-4521

http://orcid.org/0000-0003-4499-4521


SUPERCRITICAL CO2 EXTRACTION IN ART CONSERVATION

Ana Aguiar-Ricardo

REQUIMTE/LAQV, Departamento de Química, Faculdade de Ciências e Tecnologia,

Universidade Nova de Lisboa

[email protected]

Supercritical CO2 (scCO2) has already been tested and applied in conservation and restoration

operations, such as cleaning, protection and consolidation. CO2 has demonstrated a great

potential in replacing current conventional processes used in the conservation and restoration

of paper, wood, waterlogged, ethnographic materials, stone and textiles [1,2]. Cleaning

severely damaged textiles is an operation that can cause the loss of considerable amount of

material, especially if wet cleaning is used. Therefore, alternative methods and procedures for

cleaning and extract the dirty from the textiles are needed.

ScCO2 is considered a ‘‘green’’ alternative—CO2 is non-flammable, relatively non-toxic and

relatively inert—because after the extraction process it can be easily released as a gas simply

by returning to atmospheric pressure and temperature conditions [3]. Therefore, no residues

will be present in the extracted materials or in the extracted compounds. Furthermore,

processes involving CO2 as a solvent do not increase CO2 emissions but reuse the waste CO2

produced by other industries.

In this presentation, it will be outlined and discussed the research-based current knowledge

and know-how in the use of liquid and supercritical carbon dioxide for the treatment and

conservation of heritage and archaeological objects. In particular, it will be shown the

advantages of supercritical drying to stabilize to ambient conditions a wide range of

waterlogged organic materials without gross chemical or physical modification. Furthermore,

the results obtained for the cleaning of scapulary samples from the 18th century religious

garments from the Virgin and Child sculpture will be presented [4]. The Virgin’s garment are

composed of several pieces, and all the pieces were heavily damaged. Different sequences of

cleaning extractions with CO2, at liquid and supercritical conditions with and without the use of



co-solvents, in continuous conditions were tested. The best cleaning procedure was

established by analysis of loss of textile material, colour variation and dirt removal.

References

[1] B. Kaye, D. J. Cole-Hamilton and K. Morphet, Stud. Conserv., 2000, 45, 233.

[2] A. Unger, Focus Gas, 2004, 22, 20.

[3] G. Brunner, Gas Extraction. An Introduction to Fundamentals of Supercritical Fluids and

their Application to Separation Processes, Steinkopff Darmstadt, Springer, New York, 1994.

[4] M. Sousa, M. J. Melo, T. Casimiro, A. Aguiar-Ricardo, Green Chem. 2007, 9, 943-947.


NOTA CURRICULAR

ANA AGUIAR-RICARDO

Ana Aguiar-Ricardo é professora catedrática de Engenharia Química e Bioquímica, com

domínio de especialização em química verde e tecnologia supercrítica. A sua investigação

tem-se centrado no desenvolvimento de polímeros inteligentes, no seu processamento e no

desenho de novas metodologias de funcionalização. Em particular, tem desenvolvido novas

plataformas não-invasivas para libertação controlada de fármacos (e.g. por via dérmica e

pulmonar), e processos mais sustentáveis para bioseparação. Formou-se em Engenharia

Química pelo Instituto Superior Técnico (IST) e obteve um doutoramento pela Faculdade de

Ciências e Tecnologia, Universidade NOVA de Lisboa (FCT-NOVA, 1994) sob a supervisão

do Prof. M. Nunes da Ponte. Realizou um pós-doutoramento na Universidade de Nottingham,

Reino Unido (1995), no laboratório do Prof M. Poliakoff. Foi professora visitante no

Massachusetts Institute of Technology (MIT, EUA, Julho-Dezembro de 2007).

Em 2011, foi recipiente da Habilitação em Química Sustentável. Atualmente, é Presidente do

Departamento de Química (DQ), FCT-NOVA (desde Dezembro de 2017), membro da

Comissão Científica do Programa Doutoral em Química Sustentável e do corpo docente do

Programa MITPortugal (MPP), Bioengenharia de Sistemas. Foi membro do Conselho de

Faculdade da FCT-NOVA no termo 2013-2017. Representante da Sociedade Portuguesa de

Química na Associação Europeia para a Química e Ciências Moleculares (EuCheMS) na

Working Party da Química Verde e Sustentabilidade (2013-2015), na Divisão Química Verde

e Sustentabilidade (desde janeiro de 2015) e na IUPAC – Divisão Química e Ambiente (2014-

2015). É co-autora de noventa e cinco artigos em revistas científicas de especialidade, seis

capítulos de livros, mais de cinquenta artigos em anais de conferências com transferência de

direitos de autor e três artigos em revistas nacionais com revisão por pares. Registou também

duas patentes nacionais. Orientou 13 teses de doutoramento e mais de vinte dissertações de

mestrado. Foi reconhecida por duas vezes com o prémio Hovione – Solvay & Hovione

Innovation Challenge (SHIC’2008 and 2011).


VALORIZATION OF SPENT COFFEE GROUNDS

WITH SUB AND SUPERCRITICAL FLUIDS

Pedro Simões

LAQV, REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia,

Universidade Nova de Lisboa, Portugal.

[email protected]

Coffee is one of the most consumed beverages in the world. Between 2015 and 2016,

ca. 9 million tons of coffee were consumed worldwide. Spent coffee grounds (SCG), the

residue obtained from the treatment of coffee powder with hot water or steam during the

brewing process, is the major by-product of coffee industry, with up to 650 kg of dry SCG

produced per each ton of green coffee beans. SCG had until recently no commercial value,

being discarded as a solid waste or sent to compost facilities. However, SCG still contain many

compounds of interest that are present in the coffee beans, such as carbohydrates, lipids and

proteins (up to 50 wt.%, 10-15 wt.%, and 14 wt.% on a dry weight basis, respectively), besides

phenolic compounds with potential antioxidant activity. Thus, the search for the valorization of

this by-product has increased nowadays, especially with the use of environmentally clean

technologies.

Here, we show some potential applications of SCG with the use of sub and supercritical fluid

technology, ranging from the supercritical carbon dioxide extraction of SCG oil towards the

production of biodiesel [1], green biopolymers [2], or as an ingredient in topical formulations

with improved skin lipid levels and hydration [3,4], to the subcritical water extraction of bioactive

SCG extracts for enhanced skin anti-aging and lightening effects.

References

[1] R. Couto, J. Fernandes, M. Silva, P. Simões, Supercritical fluid extraction of lipids from spent coffee

grounds, The Journal of Supercritical Fluids 51 (2009) 159-166.

[2] M.V. Cruz, A. Paiva, P. Lisboa, F. Freitas, V.D. Alves, P. Simões, S. Barreiros, M.A.M. Reis,

Production of polyhydroxyalkanoates from spent coffee grounds oil obtained by supercritical fluid

extraction technology, Bioresource Technology 157 (2014) 360-363.

[3] H. Ribeiro, J. Marto, S. Raposo, M. Agapito, V. Isaac, B.G. Chiari, P.F. Lisboa, A. Paiva, S. Barreiros,

P. Simões, From coffee industry waste materials to skin‐friendly products with improved skin fat levels,

European Journal of Lipid Science and Technology 115 (2013) 330-336.

[4] J. Marto, L. Gouveia, B. Chiari, A. Paiva, V. Isaac, P. Pinto, P. Simões, A. Almeida, H. Ribeiro, The

green generation of sunscreens: Using coffee industrial sub-products. Industrial Crops and Products 80

(2016) 93-100.



NOTA CURRICULAR

PEDRO SIMÕES

Research Activities

The main area of scientific activity has been the development of integrated and sustainable

processes involving alternative green solvents such as fluids at sub- super-critical conditions,

divided in several key topics: High pressure phase equilibria, Mass transfer kinetics and

dynamic modelling of countercurrent packed columns, Valorisation of biomass resources.

Publications (related with subject of this workshop)

B Pedras, M Salema-Oom, I Sá-Nogueira, P Simões, A Paiva, S Barreiros, 2017. Valorization

of white wine grape pomace through application of subcritical water: Analysis of extraction,

hydrolysis, and biological activity of the extracts obtained. J Supercrit Fluids 128, 138-144;

DOI:10.1016/j.supflu.2017.05.020

J Marto, LF Gouveia, BG Chiari, A Paiva, V Isaac, P Pinto, P Simões, AJ Almeida, HM Ribeiro,

2016. The green generation of sunscreens: Using coffee industrial sub-products. Ind Crops

Prod 80, 93-100; DOI: 10.1016/j.indcrop.2015.11.033

MV da Cruz, A Paiva, P Lisboa, F Freitas, V Alves, P Simões, S Barreiros, MAM Reis, 2014.

Production of polyhydroxyalkanoates from spent coffee grounds oil obtained by supercritical

fluid extraction technology. Bioresour Technol 157, 360-363, DOI:

10.1016/j.biortech.2014.02.013

H Ribeiro, J Marto, S Raposo, M Agapito, V Isaac, BG Chiari, PF Lisboa, A Paiva, S Barreiros,

P Simões, 2013. From Coffee Industry Waste Materials to Skin-Friendly Products with

improved skin fat levels. Eur J Lipid Sci Technol 115, 330–336; DOI: 10.1002/ejlt.201200239


MICROWAVE-ASSISTED EXTRACTION:

PRINCIPLES AND APPLICATIONS

Simone Morais

REQUIMTE–LAQV, Instituto Superior de Engenharia do Porto, Instituto Politécnico do Porto,

R. Dr. António Bernardino de Almeida 431, 4200-072 Porto, Portugal

[email protected]

Last decade, the principals of green chemistry have been clearly encouraged and

implemented. Considering an environmental protection perspective, microwave-assisted

extraction is a convincing alternative and it has been successfully applied to various fields [1-

3]. This technique consists in using microwave energy (electromagnetic radiation in the

frequency range 0.3 to 300 GHz) to generate heat directly within the material - volumetric

heating – [4].

Microwave radiation is transformed into heat through ionic conduction and/or dipole rotation,

consequently non-polar compounds are not heated when exposed to this type of energy. MAE

may be performed using closed (pressurized) or open (focused) vessels operating,

respectively, at controlled temperature and/or pressure, and under atmospheric pressure.

Static and dynamic modes are also other two possibilities being the first usually applied with

closed vessels. Dynamic modes are particularly interesting for on-line industrial applications

[4]. Optimization of MAE variables is essential to maximize analytes recovery and minimize

degradation. The most important parameters that should be taken in consideration are the

matrix and analyte characteristics, the solvent type, the solvent volume (directly related to the

sample weight), the temperature and the extraction time. MAE has become relatively mature

(principally on the laboratory scale) and some patents have been published. Authors [1-3, 5-

6] are unanimous in concluding that the main merits of MAE are the inherent type of heating -

volumetric and selective heating-, energy savings, clean energy transfer, enhanced control of

process parameters, the reduction of solvents consumption and waste disposal, and extraction

time while sample throughput is increased and comparable or higher yields with higher

reproducibility are reached. However, a few disadvantages are still identified such as the low



selectivity (observed principally at high temperatures and pressures), equipment cost, and the

implementation complexity of electromagnetic heating in industrial applications coupled with

its safety aspects [7]. Moreover, MAE efficiency may be quite low when the viscosity of solvent

is extremely high [1]. Still, MAE is cost-effective when compared to other novel extraction

methodologies (i.e. supercritical-fluid extraction, accelerated solvent extraction). Combining

MAE with other extraction methodologies may help overcoming the limitations of the single

extraction technique and synergistic results may be reached; these possibilities have been

emerging and attracting more attention recently [8].

Acknowledgements:

Simone Morais thanks the financial support to the projects Operação NORTE-01-0145-FEDER-000011

– Qualidade e Segurança Alimentar – uma abordagem (nano)tecnológica. This work was also supported

by the project UID/QUI/50006/2013 – POCI/01/0145/FEDER/007265 with financial support from

FCT/MEC through national funds and co-financed by FEDER.

References:

[1] Morais, S. (2013) “Chapter 18: Ultrasonic- and microwave-assisted extraction and modification of

algal components”, in Functional Ingredients from Algae for Foods and Nutraceuticals (Ed. H.

Dominguez), ISBN: 978 0 85709 512 1, Woodhead Publishing Ltd, Cambridge (UK), 585-605.

[2] Moreira, M., Morais, S., Delerue-Matos, C. (2017) “Chapter 2: Environment-friendly Bioengineering,

Volume 3 Soft Chemistry and Food Fermentation (Ed. A. M. Grumezescu and A. M. Holban), ISBN:

978-0-12-811412-4, Elsevier, Amsterdam, The Netherlands, 21-47.

[3] Radojković, M., Moreira, M. M., Soares, C., M. Barroso, F., Cvetanović, A., Švarc-Gajić, J., Morais,

S., Delerue-Matos, C., “Microwave-assisted extraction of phenolic compounds from Morus nigra leaves:

optimization and characterization of the antioxidant activity and phenolic composition”, Journal of

Chemical Technology and Biotechnology (2018) in press.

[4] Balasubramanian, S., Allen, J.D., Kanitkar, A., Boldor, D. (2011) “Oil extraction from Scenedesmus

obliquus using a continuous microwave system – design, optimization, and quality characterization”,

Bioresource Technology, 102, 3396-3403.

[5] Sousa, A. M. M., Morais, S., Abreu, H., Pereira, R., Sousa-Pinto, I., Delerue-Matos, C., Gonçalves,

M. P. (2012) “Structural, physical and chemical modifications induced by microwave heating on native

agar-like galactans”, Jounal of Agricultural and Food Chemistry, 60, 4977-4985.

[6] Sousa, A.M.M., Alves, V.D., Morais, S., Delerue-Matos, C., Gonçalves, M.P. (2010) “Agar extraction

from integrated multitrophic aquacultured Gracilaria vermiculophylla: Evaluation of a microwave-

assisted process using response surface methodology”, Bioresource Technology, 101, 3258-3267.

[7] Groisman, Y., Gedanken, A. (2008) “Continuous flow, circulating microwave system and its

application in nanoparticle fabrication and biodiesel synthesis”, J Phys Chem C, 112, 8802-8808.

[8] Kokolakis, A.K., Golfinopoulos, S.K. (2013) “Microwave-assisted techniques (MATs); a quick way to

extract a fragrance: a review”, Nat Prod Commun., 8, 1493-504.

https://www.ncbi.nlm.nih.gov/pubmed/24354210


NOTA CURRICULAR

SIMONE MORAIS

Simone Morais (http://orcid.org/0000-0001-6433-5801) has a Ph.D. (1998) in Chemical

Engineering from the faculty of Engineering of the University of Porto.

She is Professor Adjunto at the Department of Chemical Engineering at the School of

Engineering of the Polytechnic of Porto (Portugal) and permanent researcher at REQUIMTE–

LAQV (http://www.requimte.pt/laqv/).

Her main research interests are (electro)analytical chemistry, including sample preparation

methods, biosensors, environmental health, food safety and quality.

Simone Morais co-authored more than 110 ISI papers (h-index: 24 – Scopus ID 7007053747)

and about 25 book chapters, having (co)supervised several PhD and post-doctoral fellows,

and having participated and coordinated several projects.

http://orcid.org/0000-0001-6433-5801

http://www.requimte.pt/laqv/


POSTERS


P1: PHENOLIC PROFILE AND ANTIOXIDANT ACTIVITY OF SACO

SWEET CHERRY PHENOLIC-RICH EXTRACTS

Ana C. Gonçalves1, Catarina Bento2, Fábio Jesus1, Luís R. Silva1,3*

1 CICS – UBI - Health Sciences Research Centre, University of Beira Interior, 6201-506 Covilhã, Portugal.

2 IPCB – ESALD - Polytechnic Institute of Castelo Branco, School of Health Dr. Lopes Dias,

6000-767, Castelo Branco, Portugal.

3 LEPABE – Department of Chemical Engineering, Faculty of Engineering, University of Porto,

4200-465 Porto, Portugal.

[email protected]

Over the past few years, a special attention has been paid to the use of plants and fruits

extracts in cosmetic, food and pharmaceutical industries due to their richness in phenolic

compounds whose antioxidant abilities are well-known. In this context, one of the challenges

is recovery as many as possible the most phenolics, and thus obtain high yields. Currently, the

extractions to obtain fractions rich in bioactive substances are preferentially carried out using

water-alcohol solvent mixtures, often including ethanol or methanol given their affinity with both

lipophilic and hydrophilic bioactive molecules. After that, the extracts normally are purified and

suffer partial concentration through solid-phase extraction (SPE) using C18 cartridges. This

last step allows to remove other constituents, like carbohydrates, lipids, organic acids and

sugars, and to isolate phenolics before analysis. Among fruits, sweet cherries (Prunus avium

Linnaeus (L.)) have been intensively studied owing to their high content in phenolics and

consequently great biological potential and health benefits. Therefore, in this work we prepared

three hydroethanolic (70:30) extracts of Saco sweet cherry cultivar using a C18 SPE column:

(i) total extract, (ii) non-coloured phenolic fraction and (iii) coloured phenolic fraction. The

extraction yields of the total extract, non-coloured fraction and coloured fraction were 13.0 ±

0.01%, 8.5 ± 0.02% and 3.6 ± 0.005%, respectively. These ones are considered satisfactory,

given the fact that sweet cherries are mainly composed by water (80%). The three extracts

were used to determine the phenolic profile of Saco cultivar by liquid chromatography with

diode array detection (LC-DAD) technique and to evaluate their biological potential, testing the

extracts’ capacity to scavenge free-radicals (DPPH●, nitric oxide (●NO), superoxide radical



(O2●-)) and to protect human erythrocytes against peroxyl radicals (ROO●). A total of twenty

non-coloured phenolics and six anthocyanin’s were detected. In respect to antioxidant activity,

Saco showed great antioxidant potential in a concentration-dependent manner, demonstrated

through the DPPH●, ●NO and O2●-, as well as to protect human erythrocytes against ROO●. In

a general way, the total extract showed the best efficiency, mostly due to a synergetic

interaction between the different phenolics. Additionally, comparing the two separate fractions,

the coloured fraction showed the most activity in all the assays, proving to be the biggest

contributor of Saco cherries’ biological activity. Our work proved that Saco cultivar is an

excellent source of phenolic compounds, which are natural antioxidants that easily capture

reactive species.

Acknowledgments – This work is supported by FEDER funds through the POCI - COMPETE

2020 - Operational Programme Competitiveness and Internationalisation in Axis I –

Strengthening research, technological development and innovation (Project POCI-01-0145-

FEDER-007491), Operational Program of the Center (Project CENTRO-01-0247-FEDER-

017547) and National Funds by FCT - Foundation for Science and Technology (Project

UID/Multi/00709/2013). Luís R. Silva (SFRH/BPD/105263/2014) was supported by post doc

grants from FCT and by a post doc incentive grant under the Protocol signed between the

University of Beira Interior (UBI) and Banco Santander / Totta. Ana Carolina and Catarina

Bento were supported by the R&D Business Project (Project CENTRO-01-0247-FEDER-

017547), co-financed by the European Regional Development Fund (ERDF) through the

Regional Operational Program of the Center (Portugal 2020).


P2: RECOVERY OF ANTIOXIDANT COMPOUNDS

FROM APPLE WOOD WASTES FROM PORTUGUESE VARIETIES

BY MICROWAVE-ASSISTED EXTRACTION

Manuela M. Moreiraa, Braam Devosa,b, M. Fátima Barrosoa, Raul Rodriguesc, Annick

Boeykensb,d, Hannes Withouckb, Simone Moraisa, Cristina Delerue-Matosa

aREQUIMTE/LAQV, Instituto Superior de Engenharia do Instituto Politécnico do Porto, Porto, Portugal

bOdisee University College, School of Technology, Chemistry, Ghent, Belgium

cCentro de Investigação de Montanha (CIMO), Escola Superior Agrária, Instituto Politécnico

Viana do Castelo

dKU Leuven, Faculty of Engineering Technology, Cluster Bioengineering Technology (CBeT),

Ghent, Belgium

[email protected]

Recently, the extraction of phenolic compounds from apple wood wastes is gaining

considerable attention [1]. These compounds are known to have many health-promoting

activities, especially anticancer, antiradical and antioxidant effects. Although, the referred

benefits can vary greatly between different apple varieties [2]. In this work, two traditional

Portuguese apple wood cultivars (Porta-da-Loja and Pipo-de-Basto) and four commercial

varieties (Golden, Jonagold, Fuji and Gala) were investigated in terms of their phenolic

composition and antioxidant activity. For that, two extraction techniques, namely conventional

extraction (CE) and microwave-assisted extraction (MAE), were employed for the recovery of

phenolic compounds. Further, different spectrophotometric assays, namely total phenolic

(TPC) and total flavonoid content (TFC), 2,2-diphenyl-1-picrylhydrazyl radical scavenging

activity (DPPH-RSA) and ferric reducing antioxidant power (FRAP) assays, were used to

characterize the apple wood wastes. The highest TPC and TFC were reported for Fuji extract

obtained by MAE (52.9±3.4 mg GAE/g DW and 17.2±1.4 mg EE/g DW for TPC and TFC,

respectively). Concerning the antioxidant activity, the apple wood variety presenting the

highest values was Gala also extracted by MAE (58.2±6.3 mg TE/g DW and 66.7±3.9 mg

AAE/g DW for DPPH-RSA and FRAP assays, respectively). Regarding the traditional

Portuguese apple wood varieties studied, the highest phenolic and flavonoid content, as well



as antioxidant activity was obtained for Porta da Loja variety (TPC: 45.9±2.0 mg GAE/g DW;

TFC: 15.8±1.1 mg EE/g DW; DPPH-RSA: 42.6±2.8 mg TE/g DW and FRAP: 52.2±4.7 mg

AAE/g DW). Work is in progress to identify by HPLC which compounds are the main

responsible for the antioxidant activity of the analysed apple wood wastes. However, the

previous results demonstrate the potential of Portuguese apple wood wastes from different

varieties to be used as a promising source of phenolic compounds with antioxidant activity, for

further application in cosmetic and/or pharmaceutical industries.

Acknowledgements:

Manuela M. Moreira (SFRH/BPD/97049/2013) is grateful for her postdoctoral fellowship

financed by POPH-QREN – Tipologia 4.1 – Formação Avançada, subsidized by Fundo Social

Europeu and Ministério da Ciência, Tecnologia e Ensino Superior. The authors are also

grateful for the financial support from FCT/MEC through national funds and co-financed by

FEDER, under the Partnership Agreement PT2020 through the project UID/ QUI/50006/2013

- POCI/01/0145/FERDER/007265; the project 6818 - Transnational Cooperation, Agreement

between Portugal (FCT) and Serbia (MSTD) is also acknowledged. Annick Boeykens wishes

to acknowledge Odisee for funding by means of a PWO grant (Flemish Government).

References:

[1] M.M. Moreira, M.F. Barroso, A. Boeykens, H. Withouck, S. Morais, C. Delerue-Matos, Ind.

Crops Prod. 2017, 104, 210-220.

[2] A.T. Serra, A.A. Matias, R.F.M. Frade, R.O. Duarte, R.P. Feliciano, M.R. Bronze, M.E.

Figueira, A. Carvalho, C.M.M. Duarte, J. Func. Foods 2010, 2, 46-53.


P3: OPTIMIZAÇÃO DO PROCESSO DE EXTRACÇÃO

DE AMOSTRAS DE PRÓPOLIS PORTUGUÊS

Ana Freitas1,2, Catarina Passão1, Cristina Almeida Aguiar1,2,3, Ana Cunha1,2,3

1Departamento de Biologia, Escola de Ciências, Universidade do Minho, 4710-057 Braga, Portugal.

2CITAB – Centro de Investigação e de Tecnologias Agro-Ambientais e Biológicas, Pólo da

Universidade do Minho, Portugal.

3CEB – Centro de Engenharia Biológica, Universidade do Minho, 4710-057 Braga, Portugal.

[email protected]

Ao longo dos anos, o interesse em produtos naturais, como o própolis, tem vindo a aumentar

surpreendentemente, não só devido a uma maior sensibilidade e apetência por produtos

biológicos e seguros, mas em particular pelo perfil bioactivo do própolis que lhe confere

propriedades farmacológicas relevantes como a actividade antioxidante, antimicrobiana, anti

tumoral, entre outras, que podem ser utilizadas nas indústrias alimentar, cosmética e

farmacêutica. As actividades biológicas de própolis estão normalmente ligadas ao seu teor e

diversidade em compostos fenólicos e flavonóides, sendo o etanol a 70 % geralmente aceite

como o solvente de eleição para a extracção de compostos bioactivos de própolis [1,2,3]. A

extracção por ultra-som tem demonstrado ser o método de extracção mais eficiente, tendo em

consideração factores como o rendimento, o tempo de extracção e a alta selectividade,

quando comparado com outros métodos, como o método de extracção tradicional

(maceração) ou o método de extracção assistida por microondas[3]. Outros autores defendem

que a extracção etanólica (50 a 90 %), permite obter extractos com baixa composição em

ceras e ricos em compostos biologicamente activos, sugerindo também o etanol a 70 % como

o solvente que garante os melhores resultados em termos de rendimento mas também de

actividade antimicrobiana[4,5,6].

Este trabalho tem como objectivo a optimização do processo de extracção de própolis visando

a obtenção de extractos ricos em compostos bioactivos, nomeadamente de compostos

fenólicos, e manutenção de propriedades antimicrobianas, reduzindo o tempo e os gastos

implicados no processo de extracção, uma vez que períodos de extracção longos podem



resultar na degradação de compostos bioactivos[7,8]. Desta forma, diferentes extracções

alcoólicas e hidroalcoólicas, à escala micro, foram realizadas a fim de determinar a razão

massa de própolis e volume de solvente, e efeito ciclos/tempos de sonicação no rendimento

de extracção de várias amostras de própolis.

Contudo, a extracção etanólica tem as suas limitações, principalmente no que diz respeito à

sua aplicabilidade nas indústrias cosmética e farmacêutica, pelo que é necessário o

desenvolvimento de extractos de própolis com recurso a solventes alternativos ao etanol,

igualmente eficazes[6].

Nota: Ana Freitas e Catarina Passão tiveram igual nível de participação no trabalho.

Agradecimentos:

À FCT- Fundação Portuguesa para a Ciência e Tecnologia (PD/BD/128276/2017), no âmbito

do programa doutoral “Agricultural Production Chains – from fork to farm” (PD/00122/2012) e

dos projetos PEstOE/AGR/UI4033/2014 e INTERACT – “Integrative Research in Environment,

Agro-Chains and Technology”, no. NORTE-01-0145-FEDER-000017. A Amadeu Fortunas e

Paulo Silva pelas amostras de própolis.

Referências:

[1] Park, Y. K., e Ikegaki, M. 1998. Bioscience, Biotechnology, and Biochemistry 62(11), 2230-

2232.

[2] Cunha, I., Sawaya, A. C., Caetano, F. M., Shimizu, M. T., Marcucci, M. C., Drezza, F. T.,

Povia, G. S., e Carvalho, P. D. O. 2004. Journal of the Brazilian Chemical Society 15(6), 964-

970.

[3] Trusheva, B., Trunkova, D., e Bankova, V. 2007. Chemistry Central Journal 1(1), 13.

[4] Pietta, P. G., Gardana, C., e Pietta, A. M. 2002. Fitoterapia 73, S7-S20.

[5] Dos Santos, C. R., Arcenio, F., Carvalho, E. S., Lúcio, E. M. R. A., Araújo, G. L., Teixeira,

L. A., Sharapin, N., e Rocha, L. 2003. Revista Brasileira de Farmacognosia 13, 71-74.

[6] Kubiliene, L., Laugaliene, V., Pavilonis, A., Maruska, A., Majiene, D., Barcauskaite, K.,

Kubilius, R., Kasparaviciene, G., e Savickas, A. 2015. BMC Complementary and Alternative

Medicine 15(1), 156.

[7] Salar, R. K., Purewal S.S. e Bhatti M.S. 2016. Resource-Efficient Technologies 2, 148-157.

[8] Hammoudi R., Khenfer S., Medjouel M., Tlili M. L. e Mahammed M. H. 2017. Lebanese

Science Journal 18, 2.


P4: SUBCRITICAL WATER EXTRACTION OF SACCORHIZA POLYSCHIDES

AS AN ENVIRONMENTAL FRIENDLY TECHNIQUE

TO PREPARE A NUTRIENT RICH LIQUID FERTILIZER

Cristina Soares1, Susana Machado1, Maria Teresa Oliva-Teles1, Nataša Nastić2,

Jaroslava Švarc-Gajić2, Marija Radojković2, Saša Savić3, Aleksandra Cvetanović2,

Cristina Delerue-Matos1

1REQUIMTE/LAQV, Instituto Superior de Engenharia do Instituto Politécnico do Porto, Portugal

2Faculty of Technology, Department for Applied and Engineering Chemistry, University of Novi

Sad, Bulevar cara Lazara 1, 21000 Novi Sad, Serbia

3Faculty of Technology, University of Niš, Bulevar Oslobođenja 124, 16000 Leskovac, Serbia

[email protected]

Seaweeds harvested during low tide from the seashore have been exploited for centuries and

are still used today, for their ability to improve soil nutrition and physical structure through

composting and their plant growth stimulant properties (Arioli et al., 2015). However, it was the

availability of liquid seaweed extracts and their ease of use that revolutionized the seaweed

extract industry in England around the 1950s and enabled their widespread use in agriculture

(Booth 1969; Craigie 2011). Liquid seaweed extracts are processed from seaweed biomass

using different extraction systems such as alkaline or acid hydrolysis or cellular disruption

under pressure or fermentation (Arioli et al., 2015). In this work Saccorhiza polyschides has

been extracted by subcritical water. The influence of the most important extraction parameters

(extraction temperature and extraction pressure) on the mineral composition of the obtained

extract has been analysed. Among macrominerals, the most abundant was K (156.88±1.9

mg/g dry sample), followed by Ca (109.02±1.1 mg/g dry sample), Na (54.63±1.1 mg/g dry

sample) and Mg (10.16±0.8 mg/g dry sample). Several important microelements (Zn, B, Bi,

Ba, In, Sr, Mo, V, I and Li) have been also detected in subcritical water extract of S.

polyschides. The present study highlights the importance of S. polyschides as a potential



source of valuable macro and trace elements and its potential application as a fertilizer.

Subcritical water extraction can be regarded as an environmental friendly technique to obtain

a nutrient rich extract from an undervalued seaweed.

References:

Arioli, T., Mattner, S.W. and Winberg, P.C., 2015. Applications of seaweed extracts in

Australian agriculture: past, present and future. Journal of applied phycology, 27(5), pp.2007-

2015.

Booth, E., 1969. The manufacture and properties of liquid seaweed extracts. In Proc Int

Seaweed Symp (Vol. 6, pp. 655-662).

Craigie, J.S., 2011. Seaweed extract stimuli in plant science and agriculture. Journal of Applied

Phycology, 23(3), pp.371-393.


P5: PTEROSPARTUM TRIDENTATUM:

A NATURAL EDIBLE PLANT WITH ANTIDIABETIC POTENTIAL

Luís R. Silva1,3*, Ana C. Gonçalves1, Catarina Bento2, Fábio Jesus1, Ana R. Nunes1,2

1 CICS – UBI – Health Sciences Research Centre, University of Beira Interior, 6201-506 Covilhã, Portugal.

2 IPCB – ESALD – Polytechnic Institute of Castelo Branco, School of Health Dr. Lopes Dias,

6000-767, Castelo Branco, Portugal.

3 LEPABE – Department of Chemical Engineering, Faculty of Engineering, University of Porto,

4200-465 Porto, Portugal.

[email protected]

Since ancient times, medicinal plants are used for prevention and treatment of several

ailments, owing they are rich in several bioactive substances with strong antioxidant,

antimicrobial, cardiovascular, immunosuppressive, antidiabetic and anticancer properties.

Among bioactive substances, phenolics assumes a relevant role, because they already

showed ability to scavenge free radical species and to inhibit α-glucosidase intestinal enzyme,

thus reducing oxidative stress levels and delaying the absorption of glucose, respectively.

Given these facts, we decided to characterize the phenolic profile of infusion and

hydroethanolic extracts of Pterospartum tridentatum, an endemic plant from the northwest of

the Iberian Peninsula and Marroco, commonly known as “carqueja” or “carqueija”, by liquid

chromatography with diode array detection (LC-DAD). Additionally, their biological potential

was evalueted though DPPH•, nitric oxide (•NO) and superoxide (O2•-) radical assays and their

capacity to inhibit the α-glucosidase activity. The LC-DAD analyses allowed the detection of

13 phenolics, being genistein the major flavonoid detected in both extracts. Regarding to in

vitro antioxidant assays, both extracts showed promising free-radical scavenger activities in a

dose-dependent manner. The hydroethanolic extract was the most active against DPPH•, while

the infusion was the most effective against O2•- and •NO radicals. Furthermore, both extracts

showed great capacity to inhibit the α-glucosidase enzyme in a concentration dependent-

manner (IC50 values of 129.84 ± 0.90 µg/mL and 147.85 ± 2.54 µg/mL for infusion and



hydroethanolic extract, respectively), presenting better results than the therapeutic drug

acarbose (IC50 = 389.88 ± 48.17 µg/mL). This property is intimately linked to the presence of

genistein and quercetin derivatives in both extracts. The obtained results suggest that the P.

tridentatum extracts may be of interest for pharmaceutical and food industries to further exploit,

however more studies are needed to unravel their properties and incite their inclusion in

pharmaceutical preparations and/ or food additives.

Acknowledgments:

This work is supported by FEDER funds through the POCI - COMPETE 2020 - Operational

Programme Competitiveness and Internationalisation in Axis I – Strengthening research,

technological development and innovation (Project POCI-01-0145-FEDER-007491),

Operational Program of the Center (Project CENTRO-01-0247-FEDER-017547) and National

Funds by FCT - Foundation for Science and Technology (Project UID/Multi/00709/2013). Luís

R. Silva (SFRH/BPD/105263/2014) was supported by post doc grants from FCT and by a post

doc incentive grant under the Protocol signed between the University of Beira Interior (UBI)

and Banco Santander/ Totta. Ana Carolina and Catarina Bento were supported by the R&D

Business Project (Project CENTRO-01-0247-FEDER-017547), co-financed by the European

Regional Development Fund (ERDF) through the Regional Operational Program of the Center

(Portugal 2020).


P6: SPATIOTEMPORAL ASSESSMENT OF PYRETHROID PESTICIDE

RESIDUES IN SOILS OF CITY PARKS AND PUBLIC PLAY AREAS

Idalina Bragança1, Paulo C. Lemos2, Cristina Delerue-Matos1 and Valentina F. Domingues1

1 REQUIMTE/LAQV-GRAQ, Instituto Superior de Engenharia, Instituto Politécnico do Porto, Portugal

2 LAQV-REQUIMTE, FCT/Universidade Nova de Lisboa, Caparica, Portugal

[email protected]

The intensive use of pyrethroid pesticides raises environmental concerns [1]. These pesticide

residues have been frequently detected in soils and sediments, and have been recognized to

contribute to toxicity.

Pyrethroid pesticides are widely used as insecticides for the control of insect pests in

agriculture, public health, and animal health [2-4]. Children, especially very young ones, are

particularly sensitive to contamination. A recently study suggests that exposure to pyrethroid

pesticides might be associated with increased risk of childhood brain tumors [5].

City parks and public play areas often contain contaminated soils. Therefore, such evaluation

should be performed, and background information on pollution and toxicity should be

assessed.

A quick easy cheap effective rugged and safe (QuEChERS) method together with gas

chromatography (GC) coupled to electron-capture detector (ECD) was performed in order to

help filling this data gap. The method for the determination of pyrethroids was successfully

established and allowed the quantification of trace amounts of 8 pyrethroid pesticides

(bifenthrin, tetramethrin, cyhalothrin, permethrin, cyfluthrin, cypermethrin, fenvalerate and

deltamethrin). Ten soils samples were collected at different locations in Porto city, and tested

for pyrethroid pesticides presence in two seasons (spring and autumn). No pyrethroid

contamination was found in the analyzed soil samples, in both seasons.


Acknowledgements:

I. Bragança is grateful to FCT for the doctoral research grant financed by fellowship

(SFRH/BD/52504/2014). This work received financial support from the European Regional

Development Fund (ERDF) through the COMPETE – Operational Competitiveness under the

project UID/QUI/50006/2013.

References:

[1] Zhang, W.J., F.B. Jiang, and J.F. Ou, Proceedings of the International Academy of Ecology

and Environmental Sciences, 2011. 1(2): p. 125-144.

[2] Pfeil, R. , Academic Press: Waltham, 2014. p. 31-34.

[3] Albaseer, S.S., et al., Trac-Trends in Analytical Chemistry, 2011. 30(11): p. 1771-1780.

[4] Bronshtein, A., et al., Journal of Agricultural and Food Chemistry, 2012. 60(17): p. 4235-

4242.

[5] Chen, S., et al., Environmental Pollution, 2016. 218: 1128-1134. [1] Pfeil, R., Pesticide

Residues: Pyrethroids A2 - Motarjemi, Yasmine, in Encyclopedia of Food Safety. 2014,

Academic Press: Waltham. p. 31-34.


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