Influence of solvent on degree of acylation in the formation of sucrose esters

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

doi:10.1007/bf02628896

Cited by 18 publications

(6 citation statements)

References 5 publications

(3 reference statements)

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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%

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%

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

“…Infrared and C-13 NMR results illustrated that raffinose polyesters were synthesized by sodium metal catalyzed interesterfication of raffinose undecaacetate and FAME of long chain fatty acids. Analyses of sucrose polyesters by NMR (Mima and Kitamori, 1964) and TLC (Weiss et al, 1971(Weiss et al, , 1972Rizzi and Taylor, 1978;Mieth et al, 1983;Hamm, 1984) have been reported. Figure 6 illustrates a proposed general reaction pathway for raffinose polyester synthesis.…”

Section: Figures 2 and 3 Illustrate Tlc Analyses Of Synthesized Rpementioning

confidence: 99%

“…1976Jandacek and Webb, 1978;Mieth et al, 1983). Sucrose polyesters can be prepared by interesterification, but frequently high temperatures and toxic solvents, such as dimethylacetamide, dimethylformamide, or dimethylsulfoxide, are required (Mattson et al, 1971;Weiss et al, 1971Weiss et al, , 1972Bobalek, 1977), and the sucrose polyesters are, therefore, not suitable for food applications.Authors Akoh and Swanson are affiliated with the…”

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confidence: 99%

One‐Stage Synthesis of Raffinose Fatty Acid Polyesters

Akoh

Swanson

1987

Journal of Food Science

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Liquid polyesters of raffinose (raffinose polyesters, RPE) were synthesized by a one-stage solvent-free interesterification of raffinose undecaacetate (RUAC) and fatty acid methyl esters (FAME) of salad oils, long chain fatty acids and blends thereof. Interesterification was essentially a low temperature, low pressure process consisting of forming a homogenous melt of RUAC and FAME in the presence of an alkali metal catalyst (2% sodium). RPE were formed with 9.5.&99.3% yield based on initial weight of RUAC. Formation of RPE was evaluated with thin layer chromatography (TLC) and RPE composition determined by transesterification with 1.0 M methanolic NaOH, followed by TLC and gas liquid chromatography (GLC). The structure of RPE was confirmed by both infrared (IR) and nuclear magnetic resonance (C-13 NMR) spectroscopy. Physical properties of the synthesized RPE were similar to physical properties of sucrose polyesters (SPE), conventional salad and vegetable oils. Synthesis of RPE catalyzed by sodium metal appeared to be a deacetylation-acylation process.

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“…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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Influence of solvent on degree of acylation in the formation of sucrose esters

Cited by 18 publications

References 5 publications

Transesterification of vegetable oils: a review

Transesterification of vegetable oils: a review

One‐Stage Synthesis of Raffinose Fatty Acid Polyesters

Carbohydrate‐alkyl ester derivatives as biosurfactants

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