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Towards the Development of a Process for Lupin Beans Detoxification Wastewater with Lupanine Recovery Biological Engineering

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Towards the Development of a Process for Lupin Beans Detoxification Wastewater with Lupanine Recovery Biological Engineering Towards the development of a process for lupin beans detoxification wastewater with lupanine recovery Catarina Borralho Mendes Barbeitos Thesis to obtain the Master of Science Degree in Biological Engineering Supervisor(s): Prof. Frederico Castelo Alves Ferreira Drª. Teresa Sofia Araújo Esteves Examination Committee: Chairperson: Prof. Gabriel António Amaro Monteiro Supervisor: Prof. Frederico Castelo Alves Ferreira Members of the Committee: Prof. Carlos Alberto Mateus Afonso Eng. Renata Alexandra Ferreira Loureiro November 2016 Acknowledgements Quero agradecer aos meus orientadores, Professor Frederico Ferreira e Drª Teresa Esteves pelas suas orientações contínuas, a imensa paciência, experiência e total disponibilidade que me demonstraram e foram valiosas durante o desenvolvimento e conclusão da tese de mestrado. Ao professor Carlos Afonso e ao Svilen por toda a ajuda e acompanhamento durante a minha estadia na Faculdade de Farmácia. Foram fundamentais para a inicialização e desenvolvimento deste trabalho e com quem muito pude aprender. E como prometido é devido, Svilen, obrigada por me ensinares que “Machines are never wrong, only men are.” . Ao Flávio pelo apoio constante e fundamental durante todo o trabalho laboratorial. Por ter sido a minha salvação inúmeras vezes e porque sem ele, posso afirmar com toda a certeza, que não seria a mesma coisa. Como não poderia deixar de ser, um muito obrigado à família mais concretamente aos meus pais, Carlos e Cecília, às minhas irmãs Sofia e Madalena e à minha prima Rita por terem aturado os meus devaneios e má disposição ao longo dos meses bem como pela enorme força, carinho e infinitos incentivos que partilharam comigo. Sem esquecer também, um agradecimento especial aos meus pais pelo apoio financeiro ao longo de todo o meu ensino e que sem isso nada disto seria possível. (Espero um dia contribuir-vos com um cruzeiro.) Às minhas queridas colegas de laboratório que me deram as boas vindas, Sónia, Rita, Sofia, Inês, Rosarinho e Jéssica, que rapidamente se tornaram em tão grandes amigas e importantes para mim. Foram essenciais e um verdadeiro suporte e por isso vos fico eternamente grata. Um especial beijinho à Sonia por toda a sua ajuda até às tantas da manhã, à Rita, Sofia e Inês. As minhas pessoas de sempre, Piko, que sempre se mantem por perto para dar apoio e fazer os possíveis para manter a minha sanidade mental; à Magali que agora longe fez questão de continuar a manter-se por perto e sempre disponível para mim com as suas sábias palavras e ao João Ramalheira, amigo do peito sempre com palavras de conforto. E por fim, mas não menos importante um obrigada ao António pela sua paciência e suporte bem como por me dar constantemente na cabeça mantendo-me com os pés bem assentes na terra e mostrar que tudo se faz com trabalho. Agradeço ainda ao projecto “Abordagem bio orgânica na valorização de águas residuais da indústria alimentar: Caso da lupanina”, (Biorg4WasteWaterVal+) financiado por WaterWorks2014, Water Joint Programming Initiative (WaterJPI), WaterWorks2014, ID 278 and Fundação para a Ciência e Tecnologia Project ID: WaterJPI/0002/2014 pelo sei apoio fincanceiro; bem como à Tremoçeira e à SADES especificamente. Por fim, ao iBB Institute for Biosciences and Bioengineering do IST o qual possibilitou também a realização da minha tese. ii “Science never solves a problem without creating another ten.” George Bernard Shaw iii Abstract Every year, large amounts of fresh water is used by food processing industry to deliver safe food to society. The resulting high volumes of wastewater have to be treated before released back to the environment. The present work considers lupin beans processing wastewater and discusses effectiveness of approaches for water treatment, able to recover lupanine, an alkaloid with pharmaceutical properties. Nanofiltration, ion exchange, liquid-liquid extraction are among the separation units evaluated for lupanine wastewater detoxification, with lupanine rejection, binding or extraction higher than 99% when using NF270 nanofiltration membrane, a strong acidic resin (e.g. Amberlyst36) and an extracting solvent, respectively. A process for lupin beans wastewater detoxification and lupanine recovery was envisaged with three sequential operations: a centrifugation for removal of suspended solids, a nanofiltration operation using a NF270 membrane to obtain a detoxified water permeate and a lupanine rich retentate, and a solvent extraction of the retentate stream for isolation of lupanine from aqueous soluble compounds. Alternatively, an additional lupanine purification stage using resin Amberlyst36 is also considered, between the nanofiltration and solvent extraction for additional purification and volume reduction. Additional work-up would include solvent exchange by distillation of extraction solvent and addition of hexane to promote lupanine crystals formation to be isolated by decantation. The envisaged process was modelled using the SuperPro Designer on the basis of the detoxification of wastewater from selected fractions with higher lupanine contents resulting into the estimation of lupanine recovery higher than 98.5% for an optimistic scenario and with a purity >95%. Key words: Lupanine, Alkaloid, Nanofiltration, Resin, Liquid-Liquid Extraction, Amberlyst36, NF270, SuperPro Designer iv Table of Contents Acknowledgements ........................................................................................................................ ii Abstract ......................................................................................................................................... iv List of Tables ................................................................................................................................ vii List of Figures ............................................................................................................................... vii List of Abbreviations .......................................................................................................................x 1. Aim of studies: Motivation, Objectives and thesis outline ................................................... 1 2. Introduction .......................................................................................................................... 2 2.1. Lupinus albus L............................................................................................................ 2 2.2. Quinolizidine Alkaloids ................................................................................................. 4 2.2.1. Quinolizidine alkaloids and its toxicity ..................................................................... 4 2.2.2. Lupanine and other QA biosynthetic pathways ....................................................... 6 2.2.3. Detection and quantification of alkaloids ................................................................. 8 2.3. Lupanine .................................................................................................................... 10 2.3.1. Lupanine’s potential ............................................................................................... 10 2.3.2. Extraction and isolation of lupanine ....................................................................... 11 2.4. Membrane filtration .................................................................................................... 14 2.4.1. Nanofiltration .......................................................................................................... 14 2.4.2. Ultrafiltration ........................................................................................................... 15 2.4.3. Membrane performance ........................................................................................ 15 2.4.4. Industrial commercial membranes ......................................................................... 16 2.4.5. Factors affecting membrane performance............................................................. 19 2.4.6. Dead-end and cross-flow operations ..................................................................... 20 2.4.7. Membranes used in this study ............................................................................... 21 2.5. Resins ........................................................................................................................ 24 3. Materials and Methods ...................................................................................................... 27 3.1. Material and reagents ................................................................................................ 27 3.1.1. Nanofiltration .......................................................................................................... 27 3.1.2. HPLC ..................................................................................................................... 28 3.1.3. Resins .................................................................................................................... 29 3.1.4. Extraction ............................................................................................................... 29 v 3.2. Methods ..................................................................................................................... 30 3.2.1. Lupanine Extraction and Purification ..................................................................... 30 3.2.2. Lupanine quantification: ........................................................................................
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