Synthesis and characterization of polyethoxylate surfactants derived from phenolic lipids

Tyman, J. H. P.; Bruce, Ian E.

doi:10.1007/s11743-003-0272-3

Cited by 45 publications

(41 citation statements)

References 12 publications

(9 reference statements)

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“…Technical CNSL was obtained from 3M Research Ltd. (Harlow Essex, United Kingdom). The separation of cardanol and cardol from technical CNSL, their polyethoxylation with EO, and their characterization as surfactants have been described (1). t-Nonylphenol polyethoxylate, obtained from S.C. Johnson and Son, Inc. (Racine, WI) was of commercial origin.…”

Section: Methodsmentioning

confidence: 99%

Surfactant properties and biodegradation of polyethoxylates from phenolic lipids

Tyman

Bruce

2004

J Surfact & Detergents

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The surface tension of aqueous solutions of cardanol and cardol polyethoxylates derived from technical cashew nut-shell liquid were examined to determine their relative surfactancy. The compositions with the greatest surface tension reduction, or optimal surfactancy, were selected for biodegradation testing, in terms of total organic carbon, using a soil inoculum. The experimental surfactants in this study were compared with commercial t-nonyl polyethoxylate and glucose as reference materials. Over a period of 28 d, cardanol polyethoxylate and its saturated analog were degraded to 17 and 25%, respectively, and cardol polyethoxylate and its saturated analog were degraded approximately half that extent (37 and 46%). t-Nonylphenyl polyethoxylate remained substantially undegraded (77%), whereas glucose was almost completely degraded (5%).Technical cashew nut-shell liquid (CNSL), obtained by the industrial processing of phenolic lipids in the natural material Anacardium occidentale, which contains principally anacardic acid 1, cardol 2, and 2-methylcardol 3. Decarboxylation gives cardanol 4, together with unchanged cardol, as shown in Scheme 1. The polyethoxylates 5 and 6, depicted in Scheme 2, were obtained by the reaction of cardanol and cardol with ethylene oxide (1). t-Nonylphenol polyethoxylate 7 is shown for comparison. In each case, they contain a profile of oligomers in which m ranges from 1 to about 48. The ethoxylates were deemed ideal candidates for further surfactant and biodegradation studies, specifically, by first determining the optimal number of ethoxylate (EO) groups required for surfactancy, as judged by their relative reduction of the surface tension of water. With this information, biodegradation studies were carried out on the sample in each series exhibiting the highest surfactancy.Studies on the environmental occurrence of alkylphenols and alkylphenol ethoxylates (2) and their persistence in aquatic environments have both been reviewed extensively (3). Commercial alkylphenol polyethoxylates have received criticism on environmental and toxicological grounds (4), and although subsequent studies have suggested their accumulation is not significant (5), there also have been indications that they could be gradually phased out (6). Recent work (7) has indicated the continued existence of marine pollution with alkylphenol polyethoxylates. Studies on the response of activated sludge to variations in the composition of feed effluent (8) have indicated that alkyl ethoxylateadapted biomass was more capable of adaptation to alkylphenol ethoxylate than the reverse. Overall, there are conflicting views on the fate and effect of the present class of alkylphenol polyethoxylates in the environment.Since approximately 90% of the alkylphenol ethoxylates in the European Union are based on the petrochemical intermediate t-nonylphenol, it is of interest to examine the use of natural alkylphenols, based on the supposition that a biosynthesized compound might prove to be more biodegradable and environmentally acceptab...

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Section: Methodsmentioning

confidence: 99%

Surfactant properties and biodegradation of polyethoxylates from phenolic lipids

Tyman

Bruce

2004

J Surfact & Detergents

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“…Em função do acúmulo de poluição marinha provocada por essas substâncias, 78 derivados polietoxilados do LCC foram investigados, o que resultou em uma patente com um novo composto, de detergência similar ao nonilfenol polietoxilado comercial e biodegradabilidade superior. 79 Seguindo essa mesma linha, Peungjitton e colaboradores 80 sintetizaram e analisaram as características físico-químicas de um novo surfactante sulfonado derivado do cardanol, comparando suas propriedades com as do surfactante comercial dodecilbenzeno sulfonato de sódio (DBS). Resultados de CMC (concentração micelar crítica), tensão superficial e detergência, fazem do cardanol sulfonato de sódio (CDS) uma possível alternativa comercial ao DBS (Figura 9).…”

Section: Avanços Oportunidades E Sustentabilidadeunclassified

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

Mazzetto¹,

Lomonaco²,

Mele³

2009

Quím. Nova

135

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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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“…The crystalline material which separated was filtered (ethylene carbonate), washed with hexane and the filtrate kept at 0°C to afford the product as a white crystalline solid 0.33 g, 18%; a further crop of product (0.50 g) was separated from the filtrate kept at 0°C (total yield (46%); mp 45-46°C; (lit. 4 (1-Hydroxy-3-carbethoxymethoxy-5-pentadecylphenol), (5, n = 0) To 5-pentadecylresorcinol (1.00 g, 3.12 mmol) in refluxing benzene (40 cm 3 ) containing potassium carbonate, ethyl bromoacetate (0.52 g, 3.11 mmol) in benzene (10 cm 3 ) was added dropwise over 4 h. The mixture was refluxed for a further 20 h, then cooled and filtered and the filtrate concentrated to give an oil which was purified by column chromatography (2% ethyl acetate in chloroform) to give the product, 0.80 g, (34%); d H (500 MHz), CDCl 3 To methanolic potassium hydroxide (1.7 cm 3 ) prepared from potassium hydroxide (1.30 g, 23.2 mmol) in methanol (10 cm 3 ), 3-pentadecylphenol (1, n = 0) (1.0 g, 3.28 mmol) was added and the methanol evaporated to leave a dry solid. This was suspended in dichloromethane (10 cm 3 ) and ethylene sulfate (0.50 g, 4.03 mmol) added.…”

Section: -(3-pentadecylphenoxymentioning

confidence: 99%

“…Thus, cationic compounds [2,3], non-ionic [4,5] and anionic compounds (4 and Tyman and Durrani, Unpublished data) have been synthesised, although members of the latter have not been well characterised [6]. Technical CNSL which is obtained by the industrial process of thermal decarboxylation [1] of the natural cashew nut, contains the component C15 phenols cardanol (1, 65-70%), cardol (3, 15-20%), 2-methylcardol (5%) and polymeric material.…”

Section: Introductionmentioning

confidence: 99%

Anionic Surfactants Synthesised from Replenishable Phenolic Lipids

Bruce

Mehta

Porter

et al. 2009

J Surfact & Detergents

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The oligomers (m = 1,2,3,4 and 5) in the profile of compounds obtained in the ethoxylation of saturated cardanol with ethylene oxide have been synthesised. The first member which occurs only in traces in the reaction has now been synthesised by an improved method. This monoethoxylate of 3-pentadecylphenol and a diethoxylate of 5-pentadecylresorcinol (2-hydroxyethyl derivatives) have been synthesised by the base-catalysed reaction with ethylene carbonate. Cardanol and cardol separated from technical cashew nut-shell liquid (CNSL) have been similarly reacted as have saturated cardanol and saturated cardol obtained by reduction of the side-chain. Reaction of the anhydrous potassium salt of 3-pentadecylphenol in dichloromethane with ethylene sulfate has afforded a derivatives having a sulfate group in place of the terminal hydroxyl group and avoiding the use of sulfuric acid. Similarly CNSL and saturated CNSL reacted with ethylene sulfate gave sulfo derivatives which possess excellent surfactancy. By contrast, with sulfuric acid, 3-pentadecyl phenol monoethoxylate gave a trisulfo product comprising a terminal side-chain sulfate and a ring disulfonic acid. 3-Pentadecylphenol reacted with sulfuric acid in carbon tetrachloride to give 4-hydroxy-6-pentadecylphenol-1,3-disulfonic acid.

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Synthesis and characterization of polyethoxylate surfactants derived from phenolic lipids

Cited by 45 publications

References 12 publications

Surfactant properties and biodegradation of polyethoxylates from phenolic lipids

Surfactant properties and biodegradation of polyethoxylates from phenolic lipids

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

Anionic Surfactants Synthesised from Replenishable Phenolic Lipids

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