- Process for isolation of cardanol from technical cashew (Anacardium occidentale L.) nut shell liquid.
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Commercially available technical cashew (Anacardium occidentale L.) nut shell liquid (CNSL) contains mainly cardanol (decarboxylated anacardic acid) and cardol. Cardanol, the monophenolic component of technical CNSL, is widely used as a synthon for the preparation of a number of polymers and agricultural products. This paper describes the separation of cardanol from toxic cardol. Technical CNSL was dissolved in a mixture of methanol and ammonium hydroxide (8:5) and extracted with hexane to obtain cardanol. The resultant methanolic ammonia layer was extracted with a mixture of ethyl acetate and hexane to yield cardol. This is the first industrially feasible process based on solvent extractions for the isolation of cardanol from technical CNSL.
- Phani Kumar,Paramashivappa,Vithayathil,Subba Rao,Srinivasa Rao
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- Synthesis and characterisation of coumarins from H-cardanol
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A facile conversion of H-cardanol (side-chain hydrogenated cardanol, 3-pentadecylphenol; renewable fine chemical from the cashew industry) into value added 3-acylcoumarins, including those incorporating (+) menthol or cholesterol, has been achieved. The H-cardanol coumarin hybrid compounds were low melting, lipophilic and soluble in hydrocarbon solvents. They exhibit UV characteristics typical of 7-alkyl-3-acylcoumarins.
- Rao, H. Surya Prakash,Kamalraj
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- Unequivocal structural assignments of three cardanol derivatives: An experimental and theoretical approach
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Cardanol was obtained by vacuum distillation of ‘‘cashew nut shell liquid’’ (CNSL). Cardanol is a by-product of cashew production and a building block for chemical synthesis; cardanol and its derivatives can be used for different types of applications. Three of these compounds are the subject of the present NMR study and theoretical comparison. 1H and 13C NMR signals were assigned using 1D and 2D NMR experiments. The DFT/B3LYP method using the cc-pVTZ basis set was employed for the calculations of the 1H and 13C NMR chemical shifts (δ). The obtained data were used as an auxiliary tool for unequivocal assignment of all 1H and 13C NMR signals. For these compounds, the adopted theoretical model was sufficient to obtain a good description of the chemical shifts.
- Barbosa, Layla R.,Souza, Daiane S.,Queiroz, Luiz H.K.,Neto, Alvaro C.,de Lima, Denis P.,Beatriz, Adilson,Rom?o, Wanderson,de Castro, Eustaquio V.R.,Lacerda, Valdemar
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p. 357 - 366
(2018/09/18)
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- Synthesis of bio-based surfactants from cashew nutshell liquid in water
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3-Pentadecylcyclohexylamines were synthesised via Pd/C-catalysed reductive amination of crude cashew nutshell liquid, an underused waste product, with hydrogen in water. The short, modular, and waste-minimised synthetic approach enables access to structurally diverse neutral, cationic, and zwitterionic tenside derivatives.
- Bragoni, Valentina,Rit, Raja K.,Kirchmann, Robin,Trita, A. Stefania,Goo?en, Lukas J.
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supporting information
p. 3210 - 3213
(2018/07/29)
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- Valorization of Madagascar's CNSL via the synthesis of one advanced intermediate (3-Pentadecylcyclohexanone)
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A unique advanced intermediate: 3-Pentadecylcyclohexanone was synthetized from the crude product which contained a mixture of cardanol, cardol and 2-methylcardol, which was hydrogenated onto Pd/C at 80 °C. From this alkylated cyclohexanone: C15 alkylated adipic acid, caprolactam, caprolactone, were synthetized in high yields, such products may have many potentially applications in polymer chemistry. The condensation of the 3-pentadecyl-cyclohexanone and triethylene glycol in oxidative or reductive conditions gave aryl ether and cyclohexyl ether, this may be a way to prepare intermediate for surfactant chemistry. Therefore we show that Cashew Nut Shell Liquid (CNSL) may lead to numerous useful compounds thank to the preparation of a unique advanced intermediate.
- Rahobinirina, Andrianarivo Irène,Rakotondramanga, Maonja Finaritra,Berlioz-Barbier, Alexandra,Métay, Estelle,Ramanandraibe, Voahangy,Lemaire, Marc
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supporting information
p. 2284 - 2289
(2018/03/26)
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- A 'meta effect' in the fragmentation reactions of ionised alkyl phenols and alkyl anisoles
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The competition between benzylic cleavage (simple bond fission [SBF]) and retro-ene rearrangement (RER) from ionised ortho, meta and para RC 6H4OH and RC6H4OCH3 (R = n-C3H7, n-C4H9, n-C5H11, n-C7H15, n-C9H19, n-C 15H31) is examined. It is observed that the SBF/RER ratio is significantly influenced by the position of the substituent on the aromatic ring. As a rule, phenols and anisoles substituted by an alkyl group in meta position lead to more abundant methylene-2,4-cyclohexadiene cations (RER fragmentation) than their ortho and para homologues. This 'meta effect' is explained on the basis of energetic and kinetic of the two reaction channels. Quantum chemistry computations have been used to provide estimate of the thermochemistry associated with these two fragmentation routes. G3B3 calculation shows that a hydroxy or a methoxy group in the meta position destabilises the SBF and stabilises the RER product ions. Modelling of the SBF/RER intensities ratio has been performed assuming two single reaction rates for both fragmentation processes and computing them within the statistical RRKM formalism in the case of ortho, meta and para butyl phenols. It is clearly demonstrated that, combining thermochemistry and kinetics, the inequality (SBF/RER) metaorthopara holds for the butyl phenols series. It is expected that the 'meta effect' described in this study enables unequivocal identification of meta isomers from ortho and para isomers not only of alkyl phenols and alkyl anisoles but also in other alkyl benzene series. Copyright
- Bouchoux, Guy,Sablier, Michel,Miyakoshi, Tetsuo,Honda, Takashi
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p. 539 - 546
(2012/09/22)
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- COMPOUNDS CAPABLE OF ABSORBING ULTRAVIOLET RADIATION, COMPOSITIONS CONTAINING THEM AND PROCESSES FOR THEIR PREPARATION
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The molecules capable of absorbing ultraviolet radiation from the cashew nut shell liquid changes are the object of the present invention; it is also described the compositions responsible for protecting the surfaces and chemical processes for the referred molecules production.
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Page/Page column 28
(2008/06/13)
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- METHOD OF INHIBITING ALDOSE REDUCTASE IN DIABETIC HOSTS USING PHENOL DERIVATIVES
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The use of alkyl or alkenyl phenols or pharmaceutical acceptable salts thereof as aldose reductase inhibitors, and hence, as an agent for preventing or alleviating chronic diabetic complications.
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