Hexitol and sucrose esters of α‐sulfo fatty acids

Bistline, R. G.; Smith, Frank Dodd Tony; Well, J. K.; Stirton, A. J.

doi:10.1007/bf02633180

Cited by 6 publications

(4 citation statements)

References 6 publications

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“…The other sugar monosodium α-sulfonyl fatty acid esters were prepared by a method similar to that used to prepare the unsulfonated sugar esters described above. The appropriate sugar was transesterified with the appropriate methyl monosodium α-sulfonyl fatty acid ester, using sodium methoxide as the transesterification catalyst in dry dimethylformamide at 100°C and 40 mm Hg (21).…”

Section: Methodsmentioning

confidence: 99%

Sugar fatty acid ester surfactants: Structure and ultimate aerobic biodegradability

Baker

Matthews

Suares

et al. 2000

J Surfact & Detergents

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Ultimate aerobic biodegradabilities of an array of sugar ester surfactants were determined by International Standards Organisation method 7827, "Water Quality-Evaluation in an Aqueous Medium of the Aerobic Biodegradability of Organic Compounds, Method by Dissolved Organic Carbon" (1984). The surfactants were nonionic sugar esters with different-sized sugar head groups (formed from glucose, sucrose, or raffinose) and different lengths and numbers of alkyl chains [formed from lauric (C 12 ) or palmitic (C 16 ) acid]. Analogous anionic sugar ester surfactants, formed by attaching an α-sulfonyl group adjacent to the ester bond, and sugar esters with α-alkyl substituents were also studied. It was found that variations in sugar head group size or in alkyl chain length and number do not significantly affect biodegradability. In contrast, the biodegradation rate of sugar esters with α-sulfonyl or α-alkyl groups, although sufficient for them to be classified as readily biodegradable, was dramatically reduced compared to that of the unsubstituted sugar esters. An understanding of the relationship between structure and biodegradability provided by the results of this study will aid the targeted design of readily biodegradable sugar ester surfactants for use in consumer products.Surfactant biodegradability is a crucial factor in determining whether their concentrations in the environment remain below detrimental levels. Surfactants derived from sugar fatty acid esters are attractive because of their ready biodegradability, low toxicity, low irritation to eyes and skin, and the renewable nature of the sugar and fatty acid starting materials. They are widely used in food, cosmetic, and pharmaceutical formulations (1-3). Physicochemical properties of these surfactants can be tailored to suit potential applications by varying the sugar head group size and the length and number of alkyl chains. As well as nonionic surfactants, analogous anionic sugar ester surfactants can be produced by incorporation of a sulfonate group. These anionic sugar esters are more water soluble than their nonionic counterparts and may more easily replace conventional anionic surfactants in product formulations. Many effects of structural variations on the physicochemical properties of sugar ester surfactants have been reported (4-6).Sucrose fatty acid esters are rapidly biodegradable (7-13). However, the relationship between biodegradability and chemical structure of sugar ester surfactants has not been comprehensively studied. The aim of the current research was to investigate the ultimate aerobic biodegradation of surfactants derived from sugar fatty acid esters so as to develop an understanding of the relationships between surfactant structure and biodegradability. The biodegradabilities of an array of sugar ester surfactants in which the structure was systematically varied were determined. Structures of the surfactants studied are indicated in Scheme 1. Sugar head group size was varied from a monosaccharide (glucose) to a trisaccharide (raffinose). ...

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Section: Methodsmentioning

confidence: 99%

Sugar fatty acid ester surfactants: Structure and ultimate aerobic biodegradability

Baker

Matthews

Suares

et al. 2000

J Surfact & Detergents

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“…Other methods for preparation of sucrose esters have been developed, including interesterification of sucrose with fatty esters in propylene glycol solutions containing ca. 50% sodium soap (2) and interesterification of molten sucrose and fatty acid esters (3), as well as reaction of sucrose with a-sulfo fatty acids (4).…”

Section: Introductionmentioning

confidence: 99%

Lactose‐derived surfactants (I) fatty esters of lactose

Scholnick¹,

Sucharski²,

Linfield³

1974

J Americ Oil Chem Soc

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Lactose, the principal solid component of whey, is a potentially inexpensive and abundantly available raw material. Its chemical structure is well suited to serve as the hydrophilic portion of a nonionic surfactant molecule. Accordingly, a series of esters of lactose was prepared by reaction of fatty acid chlorides with anhydrous lactose in N-methyl-2pyrrolidinone. Monoesters of lauric, myristic, palmitic, stearic, oleic, and tallow fatty acids were obtained in this manner. Other methods of synthesis of the products were investigated but were unsuclpresented at the AOCS Spring Meeting, New Orleans, April 1973.2ARS, USDA.cessful. The lactose esters and their oxyethylated products were evaluated for detergency behavior, emulsification time, and lime soap dispersant requirement. The results indicate that their surfactant properties are comparable to those exhibited by analogous sucrose derivatives.

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“…These include esters of linear and branched chain, primary and secondary alcohols (ranging from 1-18 carbon atoms), and representative ring compounds to study the relationship of structure with useful properties. Recently, Weft et al (16,17) prepared monoesters of polyhydric alcohol and of hexitols and sucrose in their search for effective detergents and lime soap dispersing agents. Further work by these authors (18) has been the change of the cation from the standard Na to Li, NH4, K, Mg, and Ca and also ethanolamines to further study the structuresurfactant property relationship.…”

Section: Higher Fatty Acid Estersmentioning

confidence: 99%

“…Because the analytical methods available in the literature (8,16,39) are limited and sketchy, the writers have chosen to outline the various analyses used for a neutralized slurry of a tallow-derived alpha sulfo fatty ester.…”

Section: Analysis Of Sodium ~-Sulfo Estersmentioning

confidence: 99%

Summary of the technology for the manufacture of higher alpha‐sulfo fatty acid esters

Kapur¹,

Solomon²,

Bluestein³

1978

J Americ Oil Chem Soc

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Interest in 0t-sulfonated higher molecular weight (up to C20) fatty esters has increased in recent years in the surfactant industry due to the advent of economical sulfonation processes and methyl esters of fatty acids. In this paper, the authors present a review of the chemistry of the sulfonation of fatty esters and the two-step mechanism leading to a-sulfonation. Laboratory and pilot plant scale preparation of long chain fatty acid ot-sulfoesters with vaporized SO3 without the use of solvents are also summarized. Work on the falling film equipment with hydrogenated methyl tallowate with vaporized SO 3 is described along with procedures for neutralization and bleaching. Analytical methods for defining the a-sulfonates are discussed. A larger scale unit to continuously manufacture 0t-sulfo fatty esters from long chain fatty acid is described. A review of the commercially available continuous processes for sulfonation of the fatty acid esters with vaporized sulfur-trioxide have also been included. The properties of the salts of ~s u l f o fatty esters including the hydrolytic stability, aqueous solubility, lime soap dispersing ability, and biological properties have been tabulated. Uses of these surfactant range a-sulfo esters are included in this discussion.

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Hexitol and sucrose esters of α‐sulfo fatty acids

Cited by 6 publications

References 6 publications

Sugar fatty acid ester surfactants: Structure and ultimate aerobic biodegradability

Sugar fatty acid ester surfactants: Structure and ultimate aerobic biodegradability

Lactose‐derived surfactants (I) fatty esters of lactose

Summary of the technology for the manufacture of higher alpha‐sulfo fatty acid esters

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