The Composition of the Sucrose Monomyristate Prepared by Transesterification

Lemieux, R. U.; McInnes, A. G.

doi:10.1139/v62-363

Cited by 11 publications

(2 citation statements)

References 4 publications

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“…In the synthesis of carbohydrate esters, others have presented competing reactions for regiospecificity (21). The degree of reducing products reported here (approximately 72.5% molar basis) is consistent with the findings of others for formyl-substituted amylose (22) and myristoyl esters of sucrose (23).…”

Section: Resultssupporting

confidence: 91%

Synthesis and characterization of maltose fatty acid monoesters as biosurfactants

Allen

Tao

2002

J Surfact & Detergents

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Maltose long-chain fatty acid esters (MFAE), esterified at the 6 and 6′ position, were synthesized with stearic, palmitic, myristic, and oleic groups. Synthesis yields were 15-20% based on initial maltose present, and structural confirmation was obtained using plasma desorption mass spectrometry and nuclear magnetic resonance spectroscopy. These surfactants have surface tensions in the range of 34-36 dyn/cm at their critical micelle concentrations (CMC) of approximately 10 −5 -10 −6 mol/L. The increased chain lengths have a marked effect, reducing CMC values for MFAE by approximately three orders of magnitude over similar carbohydrate-based dodecyl chain sources. Within chain lengths between 14 and 18 carbons, the rate of change in CMC is significant and decreases with increasing chain length for MFAE. The melting points of MFAE are approximately 40°C, and the heat capacities range from 1.6 to 1.9 J/g·K. These numbers are comparable to those of sucrose esters, indicating their applicability in similar uses. However, because MFAE, unlike sucrose, possess an anomeric carbohydrate carbon position, these surfactants maintain their reducing nature and are susceptible to further derivatization. They are also synthesized from renewable, economical carbohydrates and lipids and may provide an excellent alternative to petrochemical-derived products.Paper no. S1273 in JSD 5, 245-255 (July 2002).KEY WORDS: Biosurfactants, carbohydrate esters, nonionic surfactants, sugar esters.Carbohydrate polysaccharides, produced naturally in plants, account for approximately 75% of the dry weight of the biological world and nearly 80% of the human caloric diet (1). Currently, corn, potatoes, tapioca, and wheat plants are all processed to provide common sources of starch. Carbohydrates are of interest because of the number of reactive hydroxyl groups they contain. Condensation of one of the reactive groups of a saccharide with a fatty acid produces a surface-active agent. Carbohydrate-based surfactants have been used primarily in the cosmetic, detergent, food, and pharmaceutical industries (2) because they are physiologically, dermatologically, and biologically acceptable (3). Because they are odorless, tasteless, nonionic, and biodegradable, they compare well in overall performance (i.e., emulsification, detergency, foam power, wettability, and other related properties) with other surface-active compounds (4). To date, several major types of carbohydratebased surfactants are commonly used worldwide, including sorbitan esters, sucrose esters, alkyl glycosides, and glucoseamide derivatives (5-8).There are three significant limitations with a majority of the existing petroleum-based surfactants. First, they are monofunctional, (i.e., can contribute only one desired property to a formulation). Therefore, several surfactants must be combined to achieve all desired properties.Second, many surfactants are incompatible and cannot function effectively with other surfactants. Cationic and anionic surfactants neutralize each other if they are combin...

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Section: Resultssupporting

confidence: 91%

Synthesis and characterization of maltose fatty acid monoesters as biosurfactants

Allen

Tao

2002

J Surfact & Detergents

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“…Independent of the method of synthesis, a complex product is formed because of the eight available hydroxyl groups. From these reaction sites, the three primary hydroxyl groups are the most reactive (5). Both for fundamental research in relation to the reactivity of the different hydroxyl groups of sucrose, and for research into the applications of sucrose esters {ratio of mono-, di-and higher substituted products}, it is important to have at our disposal a good method of analysis for these complex mixtures.…”

Section: Ghigh Performance Liquid Chromatographic Separation Of Sucrosementioning

confidence: 99%

High performance liquid chromatographic separation of sucrose fatty acid esters

Jaspers¹,

Leeuwen²,

Nieuwenhuis³

et al. 1987

J Americ Oil Chem Soc

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The synthesis of sucrose fatty acid esters always results in complex mixtures. Two procedures for quantitative analysis of sucrose monoesters, respectively sucrose diesters, by means of high performance liquid chromatography on reversed‐phase columns, are described. A mixture of methanol and water (85:15, v/v) was used for the separation of the monoesters, while methanol, ethyl acetate and water (65:25:10, v/v/v) was used for the separation of diesters. These methods gave information about the amount of monoesters and diesters in the product; the ratio between sucrose monopalmitate and sucrose monostearate, and the number of the most important structure isomers. A complete separation of all the possible diester products seemed to be impossible, due to the presence of more complex structure isomers. The described procedures can give important support during preparative work on sucrose fatty acid esters and also in the evaluation of these products for application purposes.

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