An efficient route to biscardanol derivatives and cardanol-based porphyrins via olefin metathesis

Guo, Ying‐Cen; Mele, Giuseppe; Martina, Francesca; Margapoti, Eleonora; Vasapollo, Giuseppe; Xiao, Wen‐Jing

doi:10.1016/j.jorganchem.2006.07.020

Cited by 24 publications

(16 citation statements)

References 32 publications

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“…The overall synthesis of compound 5 from cardanol (2) is summarized in Scheme 1. The numbering assigned to cardanol (2) in Scheme 1, also applies to all target compounds, 5,6,7,8,9,10, and 13. E-Hexadec-2-ene (11) was not a target compound of this study but it was detected as a major product in the crude reaction mixture by GC-MS.…”

Section: Synthesis Of 3-propylphenol (5): a Kairomone Componentmentioning

confidence: 99%

“…The use of cardanol in synthesis is not a new concept. For instance, the y In celebration of the 60th Birthday of Christian Bruneau, Université synthesis of biscardanol derivatives for application as resins, surface coating and friction lining materials [5] and the synthesis of a detergent, sodium cardanol sulfate [6], from cardanol have been reported. In addition, synthesis of novel cardanol based fulleropyrrolidines has also recently been reported [7].…”

Section: Introductionmentioning

confidence: 99%

“…Although cardanol has been exploited as a starting material, the application of homogeneous catalysis to its modification to more valuable compounds has rarely been described. The one exception is metathesis [12,13], which has been used to make alkyl chain separated biphenols (self-metathesis) and phenol esters of varying chain length (cross metathesis with, e.g., diethyl fumarate) [12] in addition to being applied to cardanol porphyrins [5,14] and cardanol fullerenes [7]. We now report homogeneous catalytic modification of cardanol to lead to a natural tsetse fly attractant, 5, a new detergent, 6, 1-octene, a polymer additive, 7, and a detergent precursor, 8 (Fig.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of a kairomone and other chemicals from cardanol, a renewable resource

Mmongoyo

Mgani

Mdachi

et al. 2012

Euro J Lipid Sci & Tech

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Synthesis of a tsetse fly kairomone component (3-propylphenol), a detergent [sodium 2-(dec-8-enyl)-6hydroxybenzenesulfonate], a polymer additive (1-octene), and a detergent precursor [3-(non-8enyl)phenol] using cardanol [3-(pentadec-8-enyl)phenol], has been accomplished. Both carboncarbon double bond isomerization and metathesis methodologies were employed in the syntheses of these target molecules. The kairomone component was obtained, albeit in low yield, in three steps starting with cardanol. Synthesis of a new detergent, sodium 2-(dec-8-enyl)-6-hydroxybenzenesulfonate, was achieved by direct metathesis of cardanol with cis-2-butene followed by sulfonation and basification. Finally, synthesis of 1-octene and 3-(non-8-enyl)phenol was accomplished in one pot by direct metathesis of cardanol with ethylene. These products have been characterized spectroscopically, especially using 1 H and 13 C NMR.

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Section: Synthesis Of 3-propylphenol (5): a Kairomone Componentmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of a kairomone and other chemicals from cardanol, a renewable resource

Mmongoyo

Mgani

Mdachi

et al. 2012

Euro J Lipid Sci & Tech

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“…CNSL derived material can be used as chemical intermediates, additives, 4,5 stabilizers, 6 lubricants, 7 diesel engine fuel alternatives, 8 anti-oxidants, 9 anticorrosive paints, sodium cardanol sulfate detergent, 10 coating, brake linings 11 and resins. 12 Although there is a large number of applications of cashew nut shell liquid (CNSL) and its components, anacardic acid and cardanol, there are very few examples of the transformation of cashew nut shell liquid and its components into small value-added molecules. The examples predominantly focused on the metathesis of the double bonds in anacardic acid and cardanols using either homogeneous or heterogeneous catalysis (the latter with Ru catalysts supported on mesoporous molecular sieve SBA-15).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of pharmaceutical drugs from cardanol derived from cashew nut shell liquid

2019

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“…Este líquido é uma das fontes mais ricas de lipídeos fenólicos não-isoprenoides de origem natural, cuja composição quí-mica principal pode ser vista na Figura 2. [24][25][26][27] Possui diversas aplicações na química fina, de acordo com a funcionalização dos produtos isolados, [13][14][15][16][17][18][19][20][21][22][23][28][29][30][31][32][33][34][35][36][37][38] aspecto que será discutido ao longo dessa revisão.…”

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Óleo da castanha de caju: oportunidades e desafios no contexto do desenvolvimento e sustentabilidade industrial

Mazzetto¹,

Lomonaco²,

Mele³

2009

Quím. Nova

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136

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Recebido em 15/1/09; aceito em 20/3/09; publicado na web em 7/4/09 CASHEW NUT OIL: OPPORTUNITIES AND CHALLENGES IN THE CONTEXT OF SUSTAINABLE INDUSTRIAL DEVELOPMENT. The new millennium is marked by a growing search for renewable fuels and alternative raw materials from biomass in the petrochemicals industry. However, there are many challenges to overcome regarding technological and human resources aspects. In this scenario, cashew nut oil, which is rich in natural phenols, is considered to be very promising for the development of synthetic and functional products and as a feedstock for production of fine chemicals and a wide variety of new materials.Keywords: cashew nut shell liquid (CNSL); phenolic components; renewable source.Anacardium occidentale L. é o seu nome científico. Pertencente a família Anacardiaceae, 1 o cajueiro é uma árvore de aparência exótica, troncos tortuosos, folhas glabras, flores masculinas e hermafroditas e fruto reniforme. Seu pedúnculo superdesenvolvido e muito apreciado pela suculência é frequentemente confundido com o fruto, quando na verdade se trata do pseudofruto, cientificamente denominado de pedúnculo floral, com coloração variante entre o amarelo e o vermelho.O fruto do cajueiro, popularmente conhecido como castanha de caju, é um aquênio de comprimento e largura variável, casca coriácea lisa, mesocarpo alveolado, repleto de um líquido escuro quase preto, cáustico e inflamável, chamado de líquido da casca da castanha do caju (LCC) ou cashew nut shell liquid (CNSL) como é conhecido internacionalmente. Na parte mais interna da castanha está localizada a amêndoa, constituída de dois cotilédones carnosos e oleosos, que compõem a parte comestível do fruto, revestida por uma película em tons avermelhados (Figura 1).A origem do cajueiro fundamenta-se em provas circunstanciais que indicam, de forma convincente, o Brasil ou pelo menos o norte da América do Sul e parte da América Central como o centro de procedência da espécie cultivada. 2 O cajueiro adapta-se melhor às regiões costeiras do nordeste brasileiro, onde faz parte da vegetação de praias e dunas, além das formações de restingas, permitindo supor que a origem filogenética da espécie reside em limítrofes da Mata Amazônica ou cerrados com ecossistemas da região Nordeste, com base na maior diversidade e adaptação da planta nestas localidades.Um forte indício sobre a origem brasileira do caju está na mais antiga referência conhecida sobre a planta, a ilustração feita pelo monge naturalista francês André Thevet 2 (1502-1590) em seu livro intitulado Singularidades da França Antártica (Les singularitez de la France Antartique), em 1557, escrito após sua passagem pela costa do Nordeste e Norte do Brasil.Atualmente, a planta está disseminada em diversos países como Índia, Moçambique, Tanzânia, Quênia e mais recentemente Vietnã, Indonésia e Tailândia. No Brasil, de acordo com o Instituto Brasileiro de Geografia e Estatística -IBGE 3 e o Sindicato das Indústrias de Beneficiamento de Castanha de Caju e Amêndoas Vegetais do Estado do Ceará -S...

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An efficient route to biscardanol derivatives and cardanol-based porphyrins via olefin metathesis

Cited by 24 publications

References 32 publications

Synthesis of a kairomone and other chemicals from cardanol, a renewable resource

Synthesis of a kairomone and other chemicals from cardanol, a renewable resource

Synthesis of pharmaceutical drugs from cardanol derived from cashew nut shell liquid

Óleo da castanha de caju: oportunidades e desafios no contexto do desenvolvimento e sustentabilidade industrial

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