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1.
Sulfoxylated methyl esters (Φ-MES) are obtained via sulfoxidation of fatty acid methyl esters with SO2, O2, and ultraviolet light of appropriate wavelength. These products may be used as co-surfactants with linear alkylbenzene sulfonate
and alkyl ether sulfate, either in heavy-duty or in hand dishwashing liquids. Standard hand dishwashing formulations based
on Φ-MESC16 are presented and discussed with regard to solubility, viscosity, performance, and skin compatibility. The experimental results
obtained indicate that the above-mentioned products can be regarded as potential components for liquid formulations. 相似文献
2.
Sulfoxidation of fatty methyl esters with SO2, O2, and ultraviolet light of appropriate wavelength has led to a synthesis of sodium methyl ester sulfonates known as Φ-MES.
The designation of Φ refers to the random positioning of SO3 in the alkyl chain. This investigation describes for the first time the operating conditions necessary to produce these new
anionic surfactants as well as the analytical methods used in their isolation, analysis, identification. Some surface properties
are discussed as well. 相似文献
3.
Leon Cohen Fernando Soto Ana Melgarejo David W. Roberts 《Journal of surfactants and detergents》2008,11(3):181-186
Sulfoxidation of fatty acid methyl esters with SO2, O2 and ultraviolet light of appropriate wavelength, has led to the synthesis of methyl esters sulfonates or sulfoxylates, known
as Φ-MES, because of the possible random position of SO3 group in the alkyl chain. Aqueous solutions based on the sulfoxylated methyl ester of palmitic acid (Φ-MES C16) have been
studied and compared to the leading types of surfactants used today: linear alkylbenzene sulfonate (LAS) secondary alkane
sulfonate (SAS) and α-sulfo fatty methyl ester sulfonate (α-MES) with regard to solubility, performance and skin compatibility.
The experimental results obtained indicate that Φ-MES C16 can be regarded as a potential component of detergent formulations
and most likely also of body care products.
Dr. Leon Cohen received his Ph.D. in chemistry at Sevilla University. In 1994, he earned the EURCHEM designation. He worked for PETRESA from 1970 to 1996. Since 1989 he has been a Professor of Chemical Engineering at the University of Cadiz, where he has led the research group on “Surface Activity and Detergency” since 1993. He is the author of more than 25 papers, more than 40 contributions to Congresses, and has four patents related to detergency. Dr. Fernando Soto received his M.Sc. in chemistry at the Sevilla University and his Ph.D. in Chemical Engineering in 2001 at Cadiz University. He has been a Professor of Chemical Engineering at the University of Cadiz, since 1979. He has been a member of the research group on “Surface Activity and Detergency” since 1994. Ana Melgarejo received her B.Sc. in Chemical Engineering at Cadiz University in 2007. Dr. David W Roberts received his Ph.D. in Chemistry from Manchester University, UK, in 1965. He is a Fellow of the Royal Society of Chemistry and has the EURCHEM designation. He worked for Unilever Research from 1967 to 2003. Since 2003 he has been a consultant in Manufacturing and Toxicological Chemistry and is an honorary researcher at John Moores University in Liverpool. He is the author of more than 100 papers in the fields of surfactant science and toxicology. 相似文献
Leon CohenEmail: |
Dr. Leon Cohen received his Ph.D. in chemistry at Sevilla University. In 1994, he earned the EURCHEM designation. He worked for PETRESA from 1970 to 1996. Since 1989 he has been a Professor of Chemical Engineering at the University of Cadiz, where he has led the research group on “Surface Activity and Detergency” since 1993. He is the author of more than 25 papers, more than 40 contributions to Congresses, and has four patents related to detergency. Dr. Fernando Soto received his M.Sc. in chemistry at the Sevilla University and his Ph.D. in Chemical Engineering in 2001 at Cadiz University. He has been a Professor of Chemical Engineering at the University of Cadiz, since 1979. He has been a member of the research group on “Surface Activity and Detergency” since 1994. Ana Melgarejo received her B.Sc. in Chemical Engineering at Cadiz University in 2007. Dr. David W Roberts received his Ph.D. in Chemistry from Manchester University, UK, in 1965. He is a Fellow of the Royal Society of Chemistry and has the EURCHEM designation. He worked for Unilever Research from 1967 to 2003. Since 2003 he has been a consultant in Manufacturing and Toxicological Chemistry and is an honorary researcher at John Moores University in Liverpool. He is the author of more than 100 papers in the fields of surfactant science and toxicology. 相似文献
4.
The foamability (dishwashing and washing machine) and detergency of LAS in heavy-duty detergents is directly compared with
polypropylenė ABS (PPABS) at various mol wt, conen, water hardnesses and temp. In every case a peak in performance is obtained
in the C11 to C17 side chain range. The peak is shifted to lower mol wt as water hardness is increased, especially at low detergent conen.
LAS opt performance is generally equal to PPABS, except in dishwashing foam in soft water. The LAS peaks, however, are shifted
to ca. one carbon lower mol wt than the PPABS. Therefore, best over-all performance is obtained for LAS whose average mol
wt corresponds to a 12.5 carbon side chain, whereas PPABS is best with an average 13.5 carbon side chain.
Dishwashing foamability is markedly different for the different isomers contained in LAS. When the phenyl group it attached
to the middle of the alkyl chain, surprisingly high results are obtained. This dishwashing difference is great enough to be
noticeable when the isomer distribution changes in whole products made using different alkylation catalysts. Detergency and
washing machine foam are not affected enough to see differences between whole alkylates.
LAS solubility is greater than PPABS and is influenced by isomer distribution.
Present address: W. Reg. Res. Lab., USDA, Albany, Calif. 相似文献
5.
T. Okano J. Tanabe M. Fukuda M. Tanaka 《Journal of the American Oil Chemists' Society》1992,69(1):44-46
The surface-active properties and emulsification ability of sodium α-sulfonated fatty acid esters, CmH2m+1CH-(SO3Na)COOCnH2n+1, were studied as a function of the hydrophobic alkyl chainlength in the fatty acid (m=8−16) and the alcohol (n=8−18). As
a result, it was discovered that sodium α-sulfonated fatty acid esters have a structural effect on the Krafft point different
from that of amphiphiles with short alkyl chains. Moreover, some of the α-sulfonated fatty acid esters have quite low interfacial
tensions, as well as non-foaming properties, which depend upon the total (m+n) number of carbon atoms in the alkyl chains. 相似文献
6.
The dishwashing performance of sodium salts of α-sulfonated methyl esters derived from palm stearin (α-SMEPS) and nonylphenol
ethoxylate alcohol (NPEO) in mixed micelle systems was evaluated as a function of weight ratio at different water hardness
values (5.12, 51.2, and 512.0 ppm CaCO3) and temperatures (20, 30, and 45°C). Manipulating several parameters, such as weight ratios in α-SMEPS and NPEO mixtures,
washing temperature, and water hardness, can enhance detergency performance. In comparison, detergency efficiency of the mixtures
increased as follows: α-SMEPS/NPEO 400<α-SMEPS/NPEO 120<α-SMEPS/NPEO 95. 相似文献
7.
D. M. Marquis S. H. Sharman R. House W. A. Sweeney 《Journal of the American Oil Chemists' Society》1966,43(11):607-614
Alpha olefin sulfonate (AOS) can be made by SO3-air sulfonation of straight chain alpha olefins followed by saponification of the neutralized product. The sulfonation step
forms unsaturated sulfonic acids, sultones and sultone sulfonic acids. Hydrolysis of the various sultones yields a mixture
of unsaturated and hydroxy sulfonates. Sulfonation of commercial mixtures of straight chain alpha olefins in a large-scale
SO3 falling film unit has given AOS of 1.5–3.0% oil based on active content and tristimulus color of about 40% saturation (2%
solution) which is readily bleachable with 1–3% NaOCl to about 10–15% saturation.
Performance of AOS made from C15−C18 alpha olefin is comparable to that of the high-foaming C11−C14 LAS in both detergency and dishwashing foam. It is superior to similar products made from internal straight chain olefins.
The product shows a low order of toxicity and biodegrad-ability slightly better than that of LAS. A C15−C16 AOS blend is especially attractive in liquid detergent formulations.
Presented at the AOCS Meeting, Los Angeles, April 1966. 相似文献
8.
Yee Seng Lim Nur Bazlina Baharudin Yee Wei Ung 《Journal of surfactants and detergents》2019,22(3):549-558
The detergency performance of α-sulfo fatty-methyl ester sulfonate (α-MES) under different water hardness conditions was compared against the dominant workhorse in Home Care products, linear alkylbenzene sulfonate (LAS). Results demonstrate that α-MES has a higher soil removal index and its detergency performance is not drastically affected by water hardness, compared to that of LAS. The addition of α-MES to LAS also shows an improved cleaning performance and better water hardness resistance, due to the structural characteristics of α-MES, which allow the molecules to be relatively insensitive toward polyvalent ions such as Ca2+ and Mg2+. The washing performance of α-MES, α-MES/LAS, and LAS with different builders at various dosages was studied, and the results indicated that the dosage of builders in the detergent product could be reduced up to 33% with the application of α-MES, while the detergency is not sacrificed. 相似文献
9.
B. L. Kapur J. M. Solomon B. R. Bluestein 《Journal of the American Oil Chemists' Society》1978,55(6):549-557
Interest in α-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 α-sulfonation. Laboratory and pilot plant scale preparation of long chain fatty
acid α-sulfoesters with vaporized SO3 without the use of solvents are also summarized. Work on the falling film equipment with hydrogenated methyl tallowate with
vaporized SO3 is described along with procedures for neutralization and bleaching. Analytical methods for defining the α-sulfonates are
discussed. A larger scale unit to continuously manufacture α-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 α-sulfo fatty esters including the hydrolytic stability, aqueous solubility,
lime soap dispersing ability, and biological properties have been tabulated. Uses of these surfactant range α-sulfo esters
are included in this discussion.
Presented at the AOCS Meeting, New Orleans, April 1976. 相似文献
10.
Phenyl isomer distributions, within current commercial limits of HF and A1C13 linear alkylbenzene sulfonates (LAS), have little effect on dishwashing performance in light-duty liquids (LDL), detergency performance in heavy-duty powders (HDP), and interfacial tension value. The most important factor in determining performance differences among commercial LAS samples is carbon chain homolog distribution. Both HF and A1C13 LAS perform equally well and can be used interchangeably in high-performance products. The optimum for foam stability in light-duty liquids shifts towards shorter alkyl chain length as water hardness increases. At 0 ppm water hardness the optimum occurs at C13: at 50–150 ppm the optimum moves to C11 and C12; and above 150 ppm the optimum shifts to include C10, C11 and C,12. The detergency performance optimum range in a phosphate built heavy-duty powder at 50 and 150 ppm water hardness includes the C12, C13 and C14 alkyl chain lengths. In a nonphosphate built powder the optimum is similar at 50 ppm hardness to that of a phosphate built powder, but shifts at 150 ppm hardness to include C11, C12 and C13. 相似文献
11.
Leon Cohen Fernando Soto C. Pratesi L. Faccetti 《Journal of surfactants and detergents》2006,9(1):47-50
In this work several batch sulfoxidation reactions of different fatty acid methyl esters, having chain lengths of C12 to C18,
in the presence of SO2, O2, and ultraviolet light of 253 nm have been carried out. The average reaction conversion for each methyl ester has been calculated
and the selectivity determined by liquid chromatography. The results indicate that conversion increases dramatically with
the increase of carbon chain length, whereas selectivity to monosulfonate seems to increase slightly as the chain length increases. 相似文献
12.
Sajid Husain P. Nageswara Sarma G. Y. S. K. Swamy K. Sita Devi 《Journal of the American Oil Chemists' Society》1993,70(2):149-155
Physicochemical data such as vapor pressures (p0), heats of vaporization (ΔHv), activity coefficents at infinite dilution (γ∞) and excess partial molar entropy (ΔS
e
0
) are considered important for conducting unit processes and designing reactor equipment. Scanty information regarding such
data is available in the literature for the higher fatty acid methyl esters. The objective of this research was to determine
the physicochemical properties of higher fatty acid methyl esters (C11–C23) by a gas-liquid chromatographic technique with SE-30 and diethylene glycol adipate as stationary phases. Correlations between
carbon numbers and various thermodynamic properties have indicated definite trends, which could be useful in predicting the
properties of unknown fatty acid methyl esters. The data generated may be useful to chemical engineers in the construction
of storage tanks, solvent extractors and distillation columns.
IICT communication no. 2993. 相似文献
13.
Single carbon cut α-olefin sulfonates (AOS) having 12, 14, 16 and 18 carbon chain lengths and several of their blends were
prepared from high-quality α-olefins by continuous SO3 sulfonation in a laboratory falling film reactor. The ultimate biodegradability of these products was studied using a modified
shake flask procedure with CO2 evolution as the major biodegradability criterion. For comparison, commercial samples of a modified Ziegler-based AOS, linear
alkylbenzene sulfonates (LAS), and an alcohol ethoxysulfate (AEOS) were included. The results showed the AOS products bio-degraded
to CO2 more completely than LAS and slightly less extensively than AEOS. CO2 evolution decreased slightly in amount and rate as AOS carbon chain length increased in the C14 to C18 range.
Presented at the AOCS meeting, May 1977, New York City. 相似文献
14.
Francis E. Luddy R. A. Barford R. W. Riemenschneider 《Journal of the American Oil Chemists' Society》1960,37(9):447-451
Summary Methyl esters were prepared from cholesteryl esters, phospholipids, and glycerides in substantially quantitative yields by
methanolysis with large excess of sodium or potassium methoxide in absolute methanol.
A silicic acid chromatographic adsorption column technique was described, which was effective in separating methyl esters
from unsaponifiables such as sterols, pigments, etc., and free acids.
Conditions for complete methanolysis of glyceride fats and oils requiring only 5 min. of reflux time were described.
Quantitative conversion of fatty acids to methyl esters was accomplished by direct esterification with absolute methanol containing
4% HCL or H2SO4 and by methylation with diazomethane.
Presented at the 50th Meeting, American Oil Chemists’ Society, New Orleans, La., April 20–22, 1959.
Eastern Utilization Research and Development Division, Agricultural Research Service, U. S. Department of Agriculture. 相似文献
15.
T. J. Micich E. A. Diamond R. G. Bistline A. J. Stirton W. C. Ault 《Journal of the American Oil Chemists' Society》1966,43(9):539-541
In continuation of work reported a year ago describing branched chain fatty acids, a series of monosodium methyl 2-sulfo-2-alkylalkanoates
[RR'C (SO3Na) CO2CH3] were synthesized. The surface active properties of these compounds were evaluated and compared with the corresponding disodium
2-sulfo-2-alkylalkanoates [RR'C (SO3Na)CO2Na]. Alkaline hydrolysis rates show that the sodium methyl esters are stable. Relative to the disodium salts, these compounds
exhibit better wetting properties and more stable foams.
Presented at the AOCS Meeting, Cincinnati, October 1965.
E. Utiliz. Res. Dev. Div., ARS, USDA. 相似文献
16.
The jaw fat of the Atlantic bottlenose dolphin (Tursiops truncatus) contains unusual wax esters which can be separated into short chain (<C24) and long chain (>C24) fractions by thin layer chromatography. The short chain wax esters (28 wt. %) have been characterized as a 72∶24∶4 mixture
of isovaleroyl, isobutoryl, and 2-methylbutyrol, esters of C14–C18 n- and iso-alcohols. The intact <C24 esters have been resolved into individual molecular species by gas liquid chromatography on open-tubular polyester columns.
The long chain wax esters (12 wt. %) contain C10–C22 n- and iso-acids esterified to the same C14–C18 n- and iso-alcohols. Gas liquid chromatography of the intact, hydrogenated >C24 esters on a short JXR column has characterized them according to carbon number and the number of methyl branches they contain. 相似文献
17.
A fractionally distilled C14−C16 fatty acid methyl ester, derived from palm oil, was sulfonated with gaseous SO3 in a falling film reactor to form an α-sulfo fatty acid methyl ester (α-SF; unbleached and unneutralized form). The included
dark-colored impurities were then separated from α-SF as a diethyl ether-insoluble matter. After purification by thin-layer
chromatography, the colored species were analyzed by ion-exchange chromatography, gel-permeation chromatography, and nuclear
magnetic resonance spectrometry. These data suggested that the colored species were polysulfonated compounds with conjugated
double bonds. Minor components in the raw fatty acid methyl ester, found by gas chromatography/mass spectrometry, were spiked
into the purified methyl palmitate and then sulfonated. The unsaturated methyl ester and hydroxy ester showed the worst color
results. The methyl oleate and methyl 12-hydroxystearate were then sulfonated and analyzed. Deep black products were obtained,
which showed the same properties as the colored species in α-SF. It was concluded that low levels of unsaturated fatty acid
methyl esters and hydroxy esters in the fatty acid methyl ester are the main causes of the coloring. 相似文献
18.
The unwanted pick-up of low levels of vagrant dyes during washing of textile fabrics can be a significant contributor to long-term
polyester appearance degradation. Fabric appearance loss from pick-up of small quantities of a standard yellow dye are measured
on both optically brightened and unbrightened polyester. Linear alkylbenzene sulfonate (LAS) surfactant micelles act as effective
dye scavengers, reducing the level of dye pick-up by the fabric substantially. The efficacy of LAS as a dye scavenger is quantified
as a function of alkyl chain length and use concentration. Dye scavenging ability per unit weight of LAS increases with increasing
molecular weight and decreasing critical micelle concentration (cmc). Dye scavenging of up to 80% of the transferable dye
is achieved at high LAS concentrations. Results with C9, C11, C13 and C15 single homolog alkyl chain lengths, and with several mixed chain length blends are presented.
Presented at the AOCS symposium on “Surfactants in Textiles,” New Orleans, May 1981. 相似文献
19.
A. J. Stirton R. G. Bistline Jr. J. K. Weil Waldo C. Ault E. W. Maurer 《Journal of the American Oil Chemists' Society》1962,39(2):128-131
A series of esters of the general formula RCH(SO3Na)-CO2R′ of 14–19 carbon atoms prepared by the α-sulfonation of propionic, butyric, pelargonic, lauric, myristic, palmitie, and
stearic acids and esterification with normal primary alcohols were compared for critical micelle concentration, surface and
interfacial tension, Ca++ stability, wetting properties, foam height, detergency, and lime soap dispersing properties. Comparison of position isomers
showed that as the hydrophilic portion moved from the center toward either end, cmc and wetting efficiency decreased, surface
and interfacial tension increased, and Ca++ stability and lime soap dispersing properties improved.
A coconut oil fatty acid forerun sulfonated with SO3 vapor and esterified with 2-ethylhexanol gave a product with useful wetting properties in soft and hard water.
Presented at the fall meeting, American Oil Chemists' Society, Chicago, October 30–November 1, 1961.
Eastern Utilization Research and Development Division, Agricultural Research Service, U. S. Department of Agriculture. 相似文献
20.
James W. Lane Kurt Hukriede Adam Jersett Damodar Koirala Dan Levings Aaron Stewart Michael A. Waxman 《Journal of the American Oil Chemists' Society》2012,89(4):721-725
We report on the preparation and selected properties of some new biodiesels which we synthesized from oils of plants growing
in Northern Wisconsin and Minnesota. The composition and the low-temperature properties such as crystallization onset T
c and end of melting T
m investigated with the help of differential scanning calorimetry are presented. Some of these biodiesels exhibited remarkably
good low-temperature characteristics. In order to further improve these properties, we use a variety of alcohols during the
transesterification process, including isopropyl, 2-butyl, and isoamyl alcohols. Using several parameters such as oil content
and crystallization onset temperature T
c, plant species that appear most promising have been identified, among those highbush cranberry (T
c ≈ −31 °C for its methyl esters, T
c ≈ −41 °C for its 2-butyl esters), dotted horsemint (T
c ≈ −17 °C for its methyl esters, T
c ≈ −40 °C for its 2-butyl esters), and American hazelnut (T
c ≈ −19 °C for its methyl esters, T
c
≈ −30 °C for its 2-butyl esters). 相似文献