Quantitative estimation of sucrose esters of plamitic acid

Weiss, T. J.; Brown, Myrtle L.; Zeringue, H. J.; Feuge, R. O.

doi:10.1007/bf02544937

Cited by 31 publications

(19 citation statements)

References 12 publications

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“…Typically, the sugar polyesters (SPE) are prepared through base-catalyzed transesterification of carbohydrates with fatty acid methyl esters, using sodium methoxide as catalyst [91][92][93][94][95] . However, some of these methods require very high temperatures (above 100 °C) and toxic low-volatile solvents (e.g.…”

Section: Fatty Acid Esters Of Carbohydratesmentioning

confidence: 99%

“…Another solvent-free process was proposed by Akoh and Swanson 93 , in which sorbitol and trealose octaoleate are produced in excellent yields (> 90%) through interesterification reactions of the correspondent acetates and methyl oleate, using Na as catalyst. The temperature (110 °C) and reaction time (2.5 h) are lower when compared to the previous work.…”

Section: Fatty Acid Esters Of Carbohydratesmentioning

confidence: 99%

See 1 more Smart Citation

Transesterification of vegetable oils: a review

Schuchardt¹,

Sercheli²,

Vargas³

1998

J. Braz. Chem. Soc.

982

539

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A transesterificação de óleos vegetais com metanol, bem como as principais aplicações de ésteres metílicos de ácidos graxos, são revisadas. São descritos os aspectos gerais desse processo e a aplicabilidade de diferentes tipos de catalisadores (ácidos, hidróxidos, alcóxidos e carbonatos de metais alcalinos, enzimas e bases não-iônicas, como aminas, amidinas, guanidinas e triamino(imino)fosforanos). Enfoque especial é dado às guanidinas, que podem ser facilmente heterogeneizadas em polímeros orgânicos. No entanto, as bases ancoradas lixiviam dos polímeros. Novas estratégias para a obtenção de guanidinas heterogeneizadas mais resistentes à lixiviação são propostas. Finalmente, são descritas várias aplicações para ésteres de ácidos graxos, obtidos por transesterificação de óleos vegetais.The transesterification of vegetable oils with methanol as well as the main uses of the fatty acid methyl esters are reviewed. The general aspects of this process and the applicability of different types of catalysts (acids, alkaline metal hydroxides, alkoxides and carbonates, enzymes and non-ionic bases, such as amines, amidines, guanidines and triamino(imino)phosphoranes) are described. Special attention is given to guanidines, which can be easily heterogenized on organic polymers. However, the anchored catalysts show leaching problems. New strategies to obtain non-leaching guanidine-containing catalysts are proposed. Finally, several applications of fatty acid esters, obtained by transesterification of vegetable oils, are described.

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Section: Fatty Acid Esters Of Carbohydratesmentioning

confidence: 99%

Section: Fatty Acid Esters Of Carbohydratesmentioning

confidence: 99%

Transesterification of vegetable oils: a review

Schuchardt¹,

Sercheli²,

Vargas³

1998

J. Braz. Chem. Soc.

982

539

View full text Add to dashboard Cite

show abstract

“…This process was commercialized in 1960 by Dai-Nippon Sugar Manufacturing Co. Ltd. of Japan for use in the food industry (13). Other applications in drying oil production for varnishes, paints, and other finishes have been explored and patented (14), using a variety of slightly modified synthesis methods (15)(16)(17)(18)(19)(20). The use of isomeric xylenes as solvents to replace DMF was studied by Curtis in 1961 (21).…”

Section: Sucrose Estersmentioning

confidence: 99%

Carbohydrate‐alkyl ester derivatives as biosurfactants

Allen

Tao

1999

J Surfact & Detergents

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Reaction of carbohydrates with long-chain plantderived lipids yields carbohydrate-alkyl ester surfactants with a polyol structure. Their renewability, low cost, and environmental acceptability make carbohydrate-alkyl ester surfactants an excellent alternative to petrochemically derived products. This article reviews developments in the synthesis and surface-active properties of carbohydrate-alkyl ester surfactants.Paper no. S1150 in JSD 2, 383-390 (July 1999). KEY WORDS:Biosurfactants, carbohydrate esters, sugar esters.Surfactants are critical to the cleaning, emulsifying, wetting, and foaming properties of many products. Surfactants are found in a host of applications, including cosmetics, textiles, pharmaceuticals, foods, ore flotation, soaps and detergents, pulp and paper manufacturing, lubricating and metalworking, agrichemicals, and petroleum mining fields. In most industrial cases, surfactants are used as processing aids and are disposed of following usage. Issues regarding disposal have created interest in more biologically acceptable alternatives and more focused use of renewable vs. nonrenewable resources.In this context, carbohydrate-based surfactants are gaining attention. Carbohydrates in the form of polysaccharides are produced naturally in plants and account for approximately three-quarters of the dry weight of the biological world and nearly 80% of the human caloric diet (1). Corn, potatoes, tapioca, and wheat are currently processed and constitute common sources of starch. Polysaccharides are of interest because of the number of reactive hydroxyl groups they carry. Condensation of one of the reactive groups of a saccharide with a fatty acid produces a surfactant. The saccharide provides the hydrophilic component, whereas the fatty acid provides the hydrophobic component. Various types of saccharides that have been used to furnish the required hydrophilicity are outlined in Scheme 1. Carbohydrate-based surfactants have been used primarily in the cosmetic, detergent, food, and pharmaceutical industries (2-4) as they are physiologically, dermatologically, and biologically acceptable (5,6). Because they are odorless, tasteless, nonionic, and biodegradable, they compare well in overall performance (i.e., emulsification, detergency, foam power, wetting power, and other related properties) with other surface-active compounds (7).To date, several major types of carbohydrate-based surfactants are used worldwide. Sucrose esters and sorbitan esters as well as other carbohydrate derivatives are highlighted here. SUCROSE ESTERSSucrose esters are synthesized primarily by combining the primary hydroxyl group of the nonreducing glucose moiety with a methyl ester of a fatty acid (Scheme 2). Synthesis of sucrose fatty acid derivatives was first considered by Herzfeld in 1880 (5). Sucrose octaesters were later synthesized and their physical properties measured (8,9). In 1924, a patent disclosing the condensation of fatty acid chlorides with sucrose in pyridine was awarded to Rosenthal (5), and in 1950 Zief (10) desc...

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“…preparation of these compounds (Weiss et al, 1971(Weiss et al, , 1972Bobaiek, 1977; Swanson, 1987, 1989), however others excluded solvents in such preparation (Heesen et al, 1976;Rizzi and Taylor, 1978).…”

Section: Palabras-clave: Emulsionante Alimentario -Esteres De áCidos mentioning

confidence: 99%

Preparation of sucrose fatty acid esters as food emulsifiers and evaluation of their surface active and emulsification properties.

Megahed¹

1999

Grasas y Aceites

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RESUMENPreparación de esteres de ácidos grasos con sacarosa como emulsionantes alimentarios y evaluación de sus propiedades superficiales y emulsionantes.Se ha llevado a cabo un método simple para la preparación de esteres de sacarosa a partir de ácidos grasos y sacarosa de bajo coste. Se han usado ácidos laurico, palmítico y oleíco en su preparación, en ausencia de solventes orgánicos. Se obtuvieron rendimientos aceptables del 86.5%, 87.3% y 88.6% para los ásteres del laurico, palmítico y oleíco respectivamente.En los productos se evaluaron sus balances hidrófilo-lipófilo (HLB), sus propiedades de tensión superficial e interfacial así como su estabilidad en emulsiones. Los resultados mostraron que estos esteres de sacarosa exhiben propiedades similares a las de los compuestos preparados comercialmente. PALABRAS-CLAVE: Emulsionante alimentario -Esteres de ácidos grasos con sacarosa -Propiedades emulsionantes -Propiedades superficiales.preparation of these compounds (Weiss et al., 1971(Weiss et al., , 1972Bobaiek, 1977; Swanson, 1987, 1989), however others excluded solvents in such preparation (Heesen et al., 1976;Rizzi and Taylor, 1978).It was planned to use a simple method for preparation of emulsifiers from sucrose and different fatty acids (lauric, palmitic and oleic) aiming to develop and improve the method of the preparation of sucrose esters. Therefore, it was objective to modify the method of Heesen et al., (1976) for the preparation of sucrose emulsifiers (solvent-free reaction) by replacing the expensive polyalcohols for the cheaper sucrose which constitutes the hydrophilic portion of the nonionic surfactant. The products were evaluated for the hydrophile-lipophile balance (HLB), surface and interfacial tension properties as well as emulsion stability. SUMMARY Preparation of sucrose fatty acid esters as food emulsifiers and evaluation of their surface active and emulsification properties.Asimple method for the preparation of sucrose esters, from fatty acids and the least expensive sucrose, has been conducted. Fatty acids namely lauric, palmitic and oleic were used in their preparation in the absence of any organic solvent. Reasonable yields amounting to 86.5%, 87.3% and 88.6% for sucrose esters of laurate, palmitate and oléate were obtained, respectively.The products were evaluated for their hydrophile-lipophile balance (HLB), surface and interfacial tension properties as well as emulsion stability. The results showed that these sucrose esters exhibit similar properties as those of the commercially prepared compounds.

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Quantitative estimation of sucrose esters of plamitic acid

Cited by 31 publications

References 12 publications

Transesterification of vegetable oils: a review

Transesterification of vegetable oils: a review

Carbohydrate‐alkyl ester derivatives as biosurfactants

Preparation of sucrose fatty acid esters as food emulsifiers and evaluation of their surface active and emulsification properties.

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