Poly(oleic diacid-<i>co</i>-glycerol): Comparison of Polymer Structure Resulting from Chemical and Lipase Catalysis

Yang, Yixin; Lu, Wenhua; Cai, Jiali; Hou, Yu; Ouyang, Suyang; Xie, Wenchun; Gross, Richard A.

doi:10.1021/ma102939k

Cited by 73 publications

(97 citation statements)

References 30 publications

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“…21 It is worth to mention that the use of DBTO as catalyst in the polycondensation of glycerol and oleic diacid at 150 °C resulted in the formation of a gel due to cross-linking. 11 For Sc(OTf) 3 , TBD and DBTO, the amount of catalyst chosen was 0.5 mol%, as commonly used in literature. 10 Lipasecatalyzed polycondensation reactions performed using Novozyme 435 (an immobilized form of CALB) usually employ 10 wt% of immobilized biocatalyst compared to the total amount of monomers.…”

Section: Synthesis Of Sorbitol-based Polyesters Using Different Catalmentioning

confidence: 99%

Green and selective polycondensation methods toward linear sorbitol‐based polyesters: enzymatic versus organic and metal‐based catalysis

et al. 2016

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This is the peer reviewed version of the following article: "Gustini, L., Lavilla, C., Janssen, W., Martínez de Ilarduya, A., Muñoz-Guerra, S. FULL PAPER Green and selective polycondensation methods toward linear sorbitol-based polyesters: enzymatic vs. organic and metal-based catalysisLiliana Gustini [a,b] , Cristina Lavilla * [a] , William W.T.J. Janssen [a] , Antxon Martínez de Ilarduya [c] , Sebastián Muñoz-Guerra [c] , Cor E. Koning [a,d] Abstract: Renewable polyesters derived from a sugar alcohol, i.e. sorbitol, were synthesized by solvent-free polycondensation. The aim was to prepare linear polyesters with pendant hydroxyl groups along the polymer backbone. The performance of the sustainable biocatalyst SPRIN liposorb CALB and the organo-base catalyst triazobiciclodecene were compared with two metal-based catalysts, viz. scandium trifluoromethanesulfonate and dibutyl tin oxide. For the four catalytic systems, the efficiency and selectivity for the implementation of sorbitol were studied, mainly via 13 C and 31 P NMR spectroscopies, while side reactions such as ether formation and dehydration of sorbitol were evaluated via MALDI-ToF-MS. Especially the biocatalyst SPRIN liposorb CALB succeeded in incorporating sorbitol in a selective way without side reactions, leading to close-to-linear polyesters. By using a renewable hydroxylreactive curing agent based on L-lysine, transparent and glossy poly(ester urethane) networks were successfully synthesized offering a tangible example of bio-based coatings.

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Section: Synthesis Of Sorbitol-based Polyesters Using Different Catalmentioning

confidence: 99%

Green and selective polycondensation methods toward linear sorbitol‐based polyesters: enzymatic versus organic and metal‐based catalysis

et al. 2016

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“…Como exemplo da vantagem do uso de biocatalisadores, Yang et al 33 fizeram uma comparação entre o uso de óxido de di-butil-estanho (DBTO) e a enzima comercial Novozym 435 como catalisadores para a síntese de poli(diácido oléico-co-glicerol). Enquanto a reação com o catalisador químico se desenvolveu a 150 ºC, a reação utilizando a enzima se desenvolveu bem a 70 ºC.…”

Section: Síntese Via Reações De Policondensaçãounclassified

“…Essas características, identificadas na reação catalisada pela enzima, permitem a obtenção de um produto de maior valor agregado que pode ser utilizado para a confecção de fibras e filmes, dentre outros produtos. 33 …”

Section: Síntese Via Reações De Policondensaçãounclassified

Applications of Enzymes in Synthesis and Modification of Polymers

Albuquerque¹,

Ribeiro²,

Rabelo³

et al. 2014

Química Nova

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Recebido em 07/06/2013; aceito em 10/12/2013; publicado na web em 21/03/2014 APPLICATIONS OF ENZYMES IN SYNTHESIS AND MODIFICATION OF POLYMERS. Enzymes are biological catalysts that offer great potential for use in the synthesis and modification of polymers, being more specific and greener than chemical catalysts. In this work, enzymes from the classes of hydrolases (lipase, cutinase and protease) and of oxidoreductases (horseradish peroxidase, manganese peroxidase and laccase) were identified as the main biocatalysts responsible for the synthesis of polymers. Biocatalysis can potentially be part of the life cycle of several polymers, including polyesters, polyurethanes, polycarbonates, polyamides, functionalized polysaccharides and polystyrene, allowing the synthesis of specialty macromolecules for fine applications and with higher added-value than commodity polymers.Keywords: enzyme polymerization; biocatalysis; lipase. INTRODUÇÃOProcessos de polimerização representam uma das principais transformações químicas industriais da atualidade, sendo, em sua maioria, conduzidos na presença de catalisadores químicos não renováveis e sob elevadas temperaturas, demandando, em alguns casos, a proteção e desproteção de grupos funcionais, de forma a evitar a ocorrência de reações indesejadas. 1 Há cerca de 20 anos, a catálise enzimática tem sido apontada como uma estratégia de grande potencial para a síntese de políme-ros, por ser ambientalmente amigável e em geral bastante seletiva, permitindo assim a obtenção de macromoléculas com propriedades diferenciadas e de maior valor agregado.2 As enzimas para a síntese e também modificação de polímeros estão nas classes das hidrolases (como lipases, proteases e esterases) e das oxidorredutases. 3A biocatálise pode ser empregada tanto para a síntese de polí-meros naturais como de polímeros sintéticos, e dentre suas maiores vantagens está a elevada seletividade (enantio-, quimio-, éstereo-e régio-seletividade), levando à obtenção de polímeros perfeitamente estruturados na maioria dos casos. Além disso, a catálise enzimática ocorre em geral de forma bastante eficiente sob condições mais brandas de temperatura e pressão, 4 demanda reduzida (ou nenhuma) quantidade de solventes orgânicos, 5 não proporciona a formação de produtos secundários e os produtos finais são de fácil separação e recuperação.6-8 Tais vantagens ficam claras especialmente quando são empregados biocatalisadores na forma imobilizada, a qual é uma técnica amplamente reportada pela literatura.9,10 A biocatálise foi reconhecida na década de 1990 como uma área nova na síntese de polímeros de precisão. 11Dessa forma, o objetivo desse artigo é apresentar um panorama das principais enzimas e condições de processo que podem ser utilizadas para a síntese e a modificação de polímeros de interesse industrial. O reconhecimento da importância do tema se traduz pela existência hoje de livros inteiramente dedicados à polimerização enzimática. 12-14 APLICAÇÕES DE ENZIMAS NA SÍNTESE DE POLÍMEROS PoliésteresOs poliésteres estão dentre ...

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“…For academic and industrial purposes, C18 dibasic acid synthesis is based on biopathways involving the ω-oxidation of the terminal methyl group of fatty acids through microbial fermentation (Yang et al, 2011). However, the chemical process is also of potential interest.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound-assisted self-metathesis reactions of monounsaturated fatty acids

Elmkaddem

Thiébaud‐Roux

et al. 2016

OCL

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-An efficient protocol for the self-metathesis of oleic acid, using ruthenium catalysts is described. The self-metathesis reaction under ultrasonic activation allows the conversion of monoenic fatty acids such as oleic acid, elaidic acid and erucic acid into diacids and olefins with very short reaction times in the presence of Grubbs ruthenium catalysts. These yields and selectivity towards the desired products are influenced by the nature of solvents. This study demonstrated that metathesis reaction carried out in DCM or 1-butanol showed promising results, since it produced a variety of products, like n-alkenes and diacids with good yields (45-75%) and high selectivities (75-95%).Keywords: Self-metathesis / long-chain diacids / oleic acid / 1,18-octadec-9-enedioic acid / 1,26-hexacos-13-enedioic acid Résumé -Métathèse activée par les ultrasons : homocouplage d'acides gras monoinsaturés. Un nouveau protocole efficace pour l'homocouplage de l'acide oléique par réaction métathèse utilisant des catalyseurs de ruthénium est décrit dans cet article. La réaction d'homocouplage activée par ultrasons permet d'obtenir avec des temps de réac-tion très faibles, la conversion d'acides gras insaturés tels que l'acide oléique, l'acide élaïdique et l'acide érucique en diacides et oléfines en présence de catalyseurs au ruthénium de Grubbs. Les rendements et la sélectivité des produits obtenus sont influencés par la nature du solvant utilisé. Cette étude a démontré que la réaction de métathèse réalisée dans du dichlorométhane ou du 1-butanol donne des résultats prometteurs : elle permet d'obtenir une grande variété d'alcènes et des diacides à longues chaînes avec de bons rendements (45-75 %) et des sélectivités élevées (75-95 %). Mots clés :Homocouplage / métathèse / diacides à longue chaîne / acide oléique / acide 1,18-octadéc-9-ènedioïque / acide 1,26-hexacos-13-ènedioïque

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Poly(oleic diacid-co-glycerol): Comparison of Polymer Structure Resulting from Chemical and Lipase Catalysis

Cited by 73 publications

References 30 publications

Green and selective polycondensation methods toward linear sorbitol‐based polyesters: enzymatic versus organic and metal‐based catalysis

Green and selective polycondensation methods toward linear sorbitol‐based polyesters: enzymatic versus organic and metal‐based catalysis

Applications of Enzymes in Synthesis and Modification of Polymers

Ultrasound-assisted self-metathesis reactions of monounsaturated fatty acids

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