Cardanol-Based Materials as Natural Precursors for Olefin Metathesis

Vasapollo, Giuseppe; Mele, Giuseppe; Sole, Roberta Del

doi:10.3390/molecules16086871

Cited by 65 publications

(50 citation statements)

References 29 publications

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“…The synthesis of porphyrins starting from cardanol are mentioned by many papers since 2004, [26][27][28][29] and they employed a procedure which consists in producing an aldehyde derivative as precursor. Normally, this precursor is compound 3 (4-[2-(3-pentadecylphenoxy) ethoxy] benzaldehyde), obtained by a reaction between compound 2 (1-(2-bromoethoxy)-3-pentadecylbenzene) and 4-hydroxybenzaldehyde in acetone using anhydrous potassium carbonate (K 2 CO 3 ) as base, stirred for 24 h and with 40% yield.…”

Section: Synthesismentioning

confidence: 99%

Synthesis, Characterization and Dielectric Properties of New 5-(4-Hydroxyphenyl)-10,15,20-tri-4-[2-(3-pentadecylphenoxy)ethoxy]phenyl porphyrin and Their Ni, Co and Cu Complexes

Mota¹,

Júnior²,

Ribeiro³

et al. 2016

J. Braz. Chem. Soc.

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New asymmetric cardanol-based porphyrins, free-base and coordinated with Ni, Co and Cu, were synthesized and completely characterized as A3B type. Such porphyrins were obtained aiming improved solubility in polar solvents due insertion of an −OH phenolic group. Their thermal and dielectric properties were also evaluated. Changes in the synthetic route reduced the reaction time and improved the yields of the aldehyde precursor obtainment. Electronic absorption spectra of the new porphyrins in CH 2 Cl 2 , EtOH and acetone, indicated a decrease in the ε (molar absorptivity) values with increasing solvent polarity, except for the nickel complex which, in acetone, showed a slight increase of 2% in the ε value. The dielectric measurements showed that the conductivity (σ) and the loss tangent (tan δ) increased with frequency, but the permittivity (ε') decreased. The results showed that the coordination of the porphyrin promoted a significant change in thermal and dielectric properties, specially for to the Ni-complex compound, which presented the best dielectric properties with interesting values of permittivity and loss tangent at 100 MHz (19.46 and 0.011 a.u., respectively). Keywords: asymmetric porphyrins, cardanol, dielectric properties IntroductionPorphyrins are relatively planar aromatic system consisting of four pyrrole type rings joined by four methynic carbons. They have attracted scientists from many areas due to their biological importance, their fascinating physical, chemical, and spectroscopic properties.1 These compounds have a high electron density due to its 18 π-electrons delocalized on the macrocyclic ring, which are responsible for their spectroscopic characteristics. 2Porphyrin and its derivatives play multiple roles in nature, such as energy transfer and light absorption in a wide range of the electromagnetic spectrum. Such features are of great interest to the industry of optoelectronic components, such as solar cells, due to its ability to act as photosensitizers when irradiated under visible light.3 Thus, this is certainly one of the most promising areas of application for these compounds. The structural modeling and synthesis of new porphyrins has grown exponentially in order to control their electronic and thermal properties. 4 The addition of substituents at the meso positions and metal ions in the center of porphyrins can improve the electrical and magnetic properties, protecting against auto-oxidation and reducing the formation of dimers. However, these structural modifications can promote, in some cases, a significant decrease in their planarity. 5A simple way to obtain porphyrins is the acid catalyzed condensation reaction of pyrrole with specific aldehyde, followed by oxidation of the porphyrinogen. This procedure, originally developed by Rothemund,6 has been refined by [7][8][9] due to the addition of metal salts to the reaction. Despite the modest yields, the relative simplicity of this method has become suited for preparation of large amounts of tetraarylporphyrins. Higher yields an...

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Section: Synthesismentioning

confidence: 99%

Synthesis, Characterization and Dielectric Properties of New 5-(4-Hydroxyphenyl)-10,15,20-tri-4-[2-(3-pentadecylphenoxy)ethoxy]phenyl porphyrin and Their Ni, Co and Cu Complexes

Mota¹,

Júnior²,

Ribeiro³

et al. 2016

J. Braz. Chem. Soc.

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“…1c). The mono-phenols, with molecular formula C 21 H 36À2n O (n = 0, 1, 2, 3), occur naturally in cashew nutshell (Vasapollo et al, 2011;Voirin et al, 2014), an agricultural by-product. Cashew nutshell liquid (CNSL) is commercially available at more than 300,000 tons per annum worldwide (Attanasi et al, 2006).…”

Section: Contents Lists Available At Sciencedirectmentioning

confidence: 99%

Extraction of gallium from Bayer liquor using extractant produced from cashew nutshell liquid

Hoang

Nguyen

Bui

et al. 2015

Minerals Engineering

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“…As can be seen in Fig. 5.19, anacardic acid, cardanol, and cardol consist [46]. Recently, Kasemsiri et al [47] have been investigated properties of experimentally manufactured wood polymer composites based on bisphenol-A/anilinetype benzoxazine (BA-a)-CNSL copolymer and eastern redcedar woodflour which also provided an economic incentive to convert a costly land management problem into the value-added products of wood composite panels.…”

Section: Novel Cardanol-benzoxazine-based Wood Compositesmentioning

confidence: 99%

Newly High-Performance Wood-Substituted Composites Based on Polybenzoxazines

Rimdusit

Jubsilp

Tiptipakorn

2013

Alloys and Composites of Polybenzoxazines

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Wood-substituted composites of natural woodflour-filled polybenzoxazine and theirs polybenzoxazine alloys with high mechanical properties, good thermal stability, and reduced water uptake have been developed. The outstanding compatibility between the woodflour and the polybenzoxazine-based polymer matrix is evidently seen from the large improvement in the composite's mechanical properties, glass-transition temperature (T g ), and char yield as also evidently seen in the fracture surface of the wood polymer composites based on polybenzoxazine. At the optimal woodflour content of 70 % by weight in polybenzoxazine results in the composite's T g as high as 200°C or about 40°C greater than that of the neat polybenzoxazine and the modulus in a range of 6.4-6.8 GPa compared to that of natural Hevea brasiliensis wood, i.e., 9.7 GPa. Polybenzoxazine is thus proved to be useful as an effective binder for lignocellulosic materials such as woodflour.

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Cardanol-Based Materials as Natural Precursors for Olefin Metathesis

Cited by 65 publications

References 29 publications

Synthesis, Characterization and Dielectric Properties of New 5-(4-Hydroxyphenyl)-10,15,20-tri-4-[2-(3-pentadecylphenoxy)ethoxy]phenyl porphyrin and Their Ni, Co and Cu Complexes

Synthesis, Characterization and Dielectric Properties of New 5-(4-Hydroxyphenyl)-10,15,20-tri-4-[2-(3-pentadecylphenoxy)ethoxy]phenyl porphyrin and Their Ni, Co and Cu Complexes

Extraction of gallium from Bayer liquor using extractant produced from cashew nutshell liquid

Newly High-Performance Wood-Substituted Composites Based on Polybenzoxazines

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