Identification of Certain Sultones as the Sensitizers in an Alkyl Ethoxy Sulfate

AND SUMMARYSaturated and unsaturated 1,3-and saturated 1,4-sultones in anionic surfactants are identified and measured by a series of separation maneuvers. The sultones are separated from the surfactant by ionexchange treatment and concentrated by thin layer chromatography. By the use of high performance liquid chromatography, the sultones are identified on the basis of their retention times and are measured by comparing their peak areas with those of reference compounds. Adequate responses are obtained from 5 /ag quantities of sultone, corresponding to 0.1 ppm sultone in a 50 g sample of alkylethoxy sulfate paste. All the sultones of interest are separated from each other. Chlorosultones can be determined after first treating them with collidine, which dehydrohalogenares them to the unsaturated sultones.

Section: Introductionmentioning

confidence: 99%

Determination of sultones in anionic surfactants

MacMillan

Wright

1977

“…Gas chromatographic (GC) and thin layer chromatographic (TLC) procedures (2) for sultone analysis were investigated simultaneously in our laboratories, but it was felt that gas chromatography was a more suitable method for use in quality control laboratories. Previous investigators (3)(4)(5) have stated that because of their thermal instability and reactivity, sultones could not be easily analyzed by gas chromatography. If these problems can be overcome, gas chromatography offers a quick and simple means for sultone analysis.…”

Section: Introductionmentioning

confidence: 99%

Gas chromatographic analysis for long chain sultones in olefin sulfonates

Callahan

Gildenberg

Omelczenko

1977

AND SUMMARYA gas chromatographic method is described for the analysis of tetradecane-l,4-sultone (C14 delta sultone) and the combination of 2-chlorotetradecane-1,3-sultone(C14 2-chloro gamma sultone), and 1tetradecene-l,3-sultone (C14 unsaturated gamma sultone) in neutral oils isolated from olefin sulfonate. Samples of the neutral oil are diluted in hexane and injected directly into the gas chromatograph. Quantitative data are obtained by comparison to known amounts of the respective sultones. Through the use of silica gel column chromatography followed by gas chromatography of collected fractions, separation and individual quantitation of the 2-chlorotetradecane-l,3 sultone and 1-tetradecene-l,3-sultone can be obtained. Routine use for control purposes has shown the method to be reliable and interlaboratory agreement of data has been good.

“…unsaturated impurities with hydrogen peroxide (Scheme 2) (14,15). ~,13-Unsaturated-7-sultones have previously been invoked as potential skin sensitizers (15).…”

mentioning

confidence: 99%

“…unsaturated impurities with hydrogen peroxide (Scheme 2) (14,15). ~,13-Unsaturated-7-sultones have previously been invoked as potential skin sensitizers (15). Plant safety represents another potential issue because of the large quantities of bleach and methanol that must be handled, and the need to continually flash off methanol for reuse (16).…”

mentioning

confidence: 99%

Nonbleach process for the purification of palm C16–18 methyl ester sulfonates

Sherry

Chapman

Creedon

et al. 1995

There has long been interest in methyl ester sulfonates (MES) derived from natural or renewable sources, such as palm oil, with considerable effort focused on process development. A major drawback with current process technology is the formation of dark brown impurities that create aesthetic and odor issues in the final product. These issues are usually addressed by bleaching rather than by chemical purification. This paper reports on a simple yet highly effective nonbleach, twostep process for purifying palm C16-18 potassium methyl ester sulfonates. The first step comprises addition of water to the impure surfactant mixture. Preferably, the temperature of the system is maintained above the Krafft point of the surfactant, thereby completely solubilizing the surfactant and associated impurities. Once completely dissolved, the surfactant mixture is allowed to cool, and the potassium-neutralized methyl ester sulfonate precipitates out selectively. In the second step, the purified surfactant is recovered by gravity-or pressure-filtration or by centrifugation, followed by drying. The process significantly improves C1 6-18 MES analytical purity and color without raising safety or environmental concerns. It also allows for the purification of products derived from lower-grade methyl esters, resolves odor issues, and does not require use of substantial amounts of solvent such as methanol. JAOCS 72, 835-841 (1995). KEY WORDS:Alkali metal methyl ester sulfonate, bleach, centrifugation, color, filtration, Krafft point, methanol, methyl ester sulfonate, purification, solubilization.Aggressive palm oil development programs in Malaysia and Indonesia are likely to make C 16-18 methyl ester sulfonates (MES) increasingly affordable (1,2). In principle, manufacturing MES from palm oil is straightforward (Scheme 1). Transesterification of the oil with methanol results in methyl esters that can be purified by distillation; sulfonation of them produces c~-sulfonic acid methyl esters that can then be neutralized with a suitable base to yield the desired MES surfactants (3,4). In practice, MES processing is complex, mainly because the sulfonation step requires a stoichiometric excess of SO 3. The excess SO 3 is necessary because the desired sulfonation reaction proceeds via one or more intermediates that