Ozonization of phenols from Anacardium occidentale (cashew)

Bruce

2003

J Surfact & Detergents

Polyethoxylates from cardanol and from cardol, the main component phenolic lipids in technical cashew nutshell liquid derived from the replenishable source Anacardium occidentale, were obtained by reaction with ethylene oxide under base-catalyzed conditions. Oligomeric mixtures resulted. In the cardanol series, the first six members of the mixture were independently synthesized for characterization purposes by a variety of reactions. The members in the oligomeric mixture were separated by HPLC, and the composition was determined by 1 H NMR spectroscopy and by chromatography. These studies were preparatory to surfactant and biodegradation studies involving comparison with commercially available polyethoxylates derived from petrochemical nonylphenol.

Section: Methodsmentioning

confidence: 99%

Synthesis and characterization of polyethoxylate surfactants derived from phenolic lipids

Bruce

2003

J Surfact & Detergents

“…Selective catalytic hydrogenolysis avoided the use of hydride reductions. A C 8 sidechain analogue is also available from ozonolysis of anacardic acid 20 and by alkylation of 6-methyl-2-hydroxybenzoic acid. 15 …”

Section: Resultsmentioning

confidence: 99%

“…3-n-Octylphenol (5, R = C 8 H 17 ) was used, prepared as described 20 by the reaction of 3-benzyloxybenzaldehyde with 1-bromoheptane and lithium followed by hydrogenolysis of the benzyl and secondary hydroxyl groups, and by ozonolysis of cardanol (1) followed by reduction. 20 By the general formylation method, 3-n-octylphenol gave a pale yellow golden oil (0.35 g), which upon column purification afforded 2-hydroxy-4-noctylbenzaldehyde (6, R = C 8 H 17 ) as an oil, R f 0.82 (CHCl 3 ).…”

Section: -Hydroxy-4-n-octylbenzaldoxime (7 R = N-c 8 H 17 ) (Scheme 1)mentioning

confidence: 99%

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The synthesis of oxime reagents from natural and semi‐synthetic phenolic lipid and alkanoic acid resources for the solvent recovery of copper(II)

J of Chemical Tech & Biotech

Iddenten

2005

In a study of the relationship between structure and efficiency towards recovery of copper(II) by chelation/solvent extraction, a series of homologous aldoximes has been synthesised from natural phenolic lipidic, and fatty lipidic renewable sources, for comparison with commercial reagents prepared from petrochemical sources. From cardanol, in technical cashew nut-shell liquid, isoanacardic aldoxime, [2-hydroxy-4-pentadec(en)yl]aldoxime, and from the natural phenolic lipid, anacardic acid, the isomer, 2-hydoxy-6-pentadec(en)ylaldoxime, have been synthesised. A C 11 analogue of anacardic aldoxime from Anacardium giganteum has been prepared. The isomeric n-octyl aldoximes have been synthesised, the o-and p-isomers from the readily available fatty acid n-octanoic acid and the m-isomer from cardanol. Related m-aldoximes have been prepared from the ketonic intermediates methyl isoamyl and methyl amyl ketones. The solvent extraction properties for copper(II) of the synthesised aldoximes have been compared with those of a current commercial reagent, 2-hydroxy-5-t-nonylbenzaldoxime (Acorga 5100, Cytec), and two former extractants, 2-hydroxy-5-t-nonylacetophenone ketoxime (SME 529, Shell) and 2-hydroxy-5-t-nonylbenzophenone ketoxime (LIX 65N, Henkel). All the aldoximes possessed useful properties in extraction efficiency, notably the isoanacardic and the C 8 aldoximes with the C 8 oisomer, 2-hydroxy-3-n-octylbenzaldoxime, exhibited optimal extraction, stripping and phase separation characteristics.

“…The use of additives from natural products has been reviewed [5]. Previously, [6] the syntheses of a series of thiobisphenols were described by reaction with sulphur dichloride, from 3-alkylphenols obtained from renewable, natural phenolic lipid sources [7,8], having saturated C 8 , C 11 and C 15 side chains. However, to our knowledge, there has been no study of the relationship between structure and properties in such thiobisphenols.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antioxidancy of Some n‐Alkyl, t‐Alkyl, Homologous and Isomeric Lipidic Alkylthiobisphenols

Johnson

2007

J Americ Oil Chem Soc

To study the relationship between structure and properties of members of the lipidic thiobis phenol series, as extreme pressure additives in lubricants, a series of homologous compounds has been synthesised by the reaction of alkylphenols with sulphur dichloride. The isomeric n-nonylphenols have been reacted to form the C9 isomeric 2,2¢-and 4,4¢-thiobisphenols. Longer alkyl sidechains resulted mainly in the formation of 4,4¢-thiobisphenols and some of the 2,2¢ isomer. With short alkyl, particularly t-alkyl side-chains, steric hindrance resulted in the 2,2¢-compound. Additive studies have indicated that the longer chain 4,4¢ compounds possessed antioxidant properties comparable and superior to former commercial branched chain 2,2¢ compounds produced from petrochemical intermediates.