New Plant and New Applications of Sucrose Esters

Kosaka, T.; Yamada, Taeko

doi:10.1021/bk-1977-0041.ch006

Cited by 18 publications

(10 citation statements)

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“…Bekkum and Lammers [30] report that Mitsubishi use DMSO as a solvent and that DKS use 138 emulsifiers in food technology the micro-emulsion process. However, authors from the two companies are less open about the precise process employed [21,31].…”

Section: Purification Methods For Sucrose Estersmentioning

confidence: 99%

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Sucrose Esters

and¹,

Cooper²

2004

Emulsifiers in Food Technology

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Section: Purification Methods For Sucrose Estersmentioning

confidence: 99%

“…This so-called USDA method involved a reaction between molten sucrose and methyl esters of fatty acids in the presence of alkali soaps that act as solubilisers and catalysts. A similar method called the Zimmer method was developed in Germany [21].…”

Section: Production Routes To Sucrose Estersmentioning

confidence: 99%

Sucrose Esters

and¹,

Cooper²

2004

Emulsifiers in Food Technology

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“…The general procedure is an interesterification process requiring a solvent [usually dimethyl sulfoxide or dimethylformamide (DMF)] and an alkaline catalyst, yielding approximately 25-35% sucrose mono-and diesters (12). 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).…”

Section: Sucrose Estersmentioning

confidence: 99%

“…Osipow and Rosenblatt stated that the need for removal of traces of toxic solvent probably contributed to the slow advancement of this industry, and hence a microemulsion might serve as a viable alternative to the mutual solvent. Eventually, propylene glycol was replaced by water (13).…”

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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“…in the final product. More recent processes for producing these emulsifiers are safer but suffer from the disadvantages that (i) their selectivities are low; (ii) they produce mixtures containing materials characterized by different degrees of esterification (3,4); (iii) they use high temperatures (170-185°C) and/or inorganic catalysts (5,6); (iv) caramelization and/or dehydration of the sugar takes place at high temperature; and (v) distillation is often required to remove unreacted reagents and alcoholic by-products. At present, mono-and diesters of sucrose and several different esters of sorbitan are commercially available.…”

mentioning

confidence: 99%

Different strategies for selective monoacylation of hexoaldoses in acetone

Arcos

Bernabé

Otero

1998

J Surfact & Detergents

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Experimental protocols for the selective production of 6-O-acylhexoaldose emulsifiers from precursor sugars (mannose, glucose, and galactose) and corresponding fatty acids are compared. The protocols employ an immobilized Candida antarctica lipase in a solvent (acetone) which is both easily eliminated and accepted by the European Economic Community for use as an extraction solvent in the manufacture of foods and/or food additives. This comparative study provides guidelines for selection of appropriate conditions for quantitative monoacylation of aldoses in acetone, on the basis of the solubilities of the precursor sugar and the monoester in acetone at different temperatures. Although relatively low temperatures (<40°C) favor precipitation of glucose monoesters, higher temperatures (e.g., 55°C) should be used to increase solubility of mannose and thus selectivity of the reaction leading to the mannose ester. Galactose is transformed with poor selectivity to the desired monoester by these procedures. Factors affecting the viability of these synthetic reactions in acetone are also discussed. JSD 1, 345-352 (1998). FIG. 1. (A) Effect of the molar ratio of lauric acid to glucose on the enzymatic synthesis of 6-lauroyl glucose. Conditions: 60 mg glucose, 2 mL acetone, 100 mg Novozym 435 (Novo Nordisk, Bagvaerd, Denmark), 200 mg of molecular sieves, 40°C. Lauric acid/glucose: • 6:1; ■, 3:1; ■ ■, 2:1; ▲, 1:1. (B) Effect of temperature on this reaction. Equimolar quantities of acid and sugar; •, 24°C, ■, 40°C; other conditions as in Figure 1A. Molar yields of monoand diesters are expressed in percentages with respect to the limiting reagent. 348 J.A. ARCOS ET AL.

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New Plant and New Applications of Sucrose Esters

Cited by 18 publications

References 0 publications

Sucrose Esters

Sucrose Esters

Carbohydrate‐alkyl ester derivatives as biosurfactants

Different strategies for selective monoacylation of hexoaldoses in acetone

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