Separation and extraction of Φ‐methyl ester sulfoxylates: New features

Cohen, L.; Soto, Fernando; Luna, M.

doi:10.1007/s11743-001-0162-8

Cited by 15 publications

(13 citation statements)

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“…ME C16, (CE-1695) from Procter & Gamble Chemicals, USA, with 99 wt.% of C16:0 alkyl chain • U-MES C16 sodium salt. This product was obtained in our laboratory according to a modification of the methodologies described previously [1,4].…”

Section: Methodsmentioning

confidence: 99%

“…According to the water procedure described in Ref. [4] after the separation of the non-reacted methyl ester, a small amount of dissolved methyl ester and some fatty acid remains in the aqueous phase, and these have to be removed in order to improve the final product quality. An updated procedure, that we present for the first time, has been implemented.…”

Section: Methodsmentioning

confidence: 99%

“…Two main conclusions were drawn: the palmitic acid U-MES (U-MES C16) could be used as an LAS partner in detergent formulations and the C16 alkyl chain was the optimal length. Since then, progress has been made concerning the development of a procedure for the separation of reaction products [4] and analysis [5,6]. These investigations have led to products with fewer impurities.…”

Section: Introductionmentioning

confidence: 99%

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Performance of Φ‐Sulfo Fatty Methyl Ester Sulfonate Versus Linear Alkylbenzene Sulfonate, Secondary Alkane Sulfonate and α‐Sulfo Fatty Methyl Ester Sulfonate

Cohen

Soto

Melgarejo

et al. 2008

J Surfact & Detergents

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Sulfoxidation of fatty acid methyl esters with SO 2, O 2 and ultraviolet light of appropriate wavelength, has led to the synthesis of methyl esters sulfonates or sulfoxylates, known as U-MES, because of the possible random position of SO 3 group in the alkyl chain. Aqueous solutions based on the sulfoxylated methyl ester of palmitic acid (U-MES C16) have been studied and compared to the leading types of surfactants used today: linear alkylbenzene sulfonate (LAS) secondary alkane sulfonate (SAS) and asulfo fatty methyl ester sulfonate (a-MES) with regard to solubility, performance and skin compatibility. The experimental results obtained indicate that U-MES C16 can be regarded as a potential component of detergent formulations and most likely also of body care products.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Performance of Φ‐Sulfo Fatty Methyl Ester Sulfonate Versus Linear Alkylbenzene Sulfonate, Secondary Alkane Sulfonate and α‐Sulfo Fatty Methyl Ester Sulfonate

Cohen

Soto

Melgarejo

et al. 2008

J Surfact & Detergents

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“…In addition, the sodium sulfonate has been extracted with n-butanol. The detailed analytical procedure has been published previously (3). The selection of the methyl ester carbon range was done according to the performance previously obtained (2).…”

Section: Methodsmentioning

confidence: 99%

Sulfoxylated methyl esters as potential components of liquid formulations

Cohen

Soto

Luna

2001

J Surfact & Detergents

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Sulfoxylated methyl esters (Φ-MES) are obtained via sulfoxidation of fatty acid methyl esters with SO 2 , O 2 , 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-MESC 16 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.Paper no. S1222 in JSD 4, 147-150 (April 2001).KEY WORDS: Φ-MES, LAS, AES, hand dishwashing liquids.In previous papers (1,2), the synthesis, characterization, and performance of sulfoxylated methyl esters (Φ-MES) were described. According to these results (2), Φ-MES showed: good solubility, very low viscosity of water solutions even at high concentration, and low sensitivity to water hardness. Furthermore, these are natural products and are then expected to have (i) excellent biodegradability and (ii) good skin compatibility. As a result, these products can be viewed as new anionic surfactants with potential application in formulations for hand dishwashing liquids or for heavy-duty liquids. The aim of the present work is to study their behavior in hand dishwashing formulations, where Φ-MES has been combined with the leading types of surfactants used in the world today: linear alkylbenzene sulfonate (LAS), alkyl ether sulfate (AES), and alcohol ethoxylate (AE). DISHWASHING LIQUID FORMULATIONSA competitive dishwashing liquid has to meet certain basic requirements, such as: good water solubility, low viscosity even at high concentrations, mildness to skin, effective fat and oil dissolution, and high and stable foam. Almost all European dishwashing liquid formulations are a mixture of LAS, AES, and other minor components and solvents (most frequently water). In order to study how the former formulations would behave if one or both of the major components (LAS or AES) were replaced partially by Φ-MES, the following ternary formulations (Table 1) were tested with regard to solubility, viscosity, stability to water hardness, skin compatibility, foaming, and hand dishwashing performance. MATERIALSΦ-MESC 16 sodium salt (where C 16 = carbon chain length). This product was obtained in our laboratory according to a modification of the methodology described (1). Basically, the modification consists of the use of hot water instead of a mixture of water and ethanol for the separation of the acid phase at the reactor outlet. In addition, the sodium sulfonate has been extracted with n-butanol. The detailed analytical procedure has been published previously (3). The selection of the methyl ester carbon range was done according to the performance previously obtained (2).LAS sodium salt. A commercial sodium sulfonate mixture derived from a linear alkylbenzene (LAB) with the following wt% composition:

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“…(ii) GC-MS showed the presence of at least 11 isomers that could not be characterized. (iii) 1 H NMR indicated that the major species present contained one CHSO 3 and one CH 2 CO 2 group, confirmed the presence of different isomers, and suggested the presence of polysulfonates. (iv) LSIMS and LSIMS/MS confirmed the presence of CH 3 (CH 2 ) m CH(SO 3 Me)(CH 2 ) n CH 2 CO 2 Me (M.W.…”

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confidence: 82%

Analysis of sulfoxylated methyl esters (Φ-MES): Sulfonic acid composition and isomer identification

et al. 2003

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Derivatization of a C 12 Φ-methyl ester sulfonic acid by using iodide-trifluoroacetic anhydride in dimethylformamide in a one-step reaction yielded derivatized sulfonic thiotrifluoroacetates. The latter have been analyzed by gas chromatography-mass spectrometry (MS) and liquid chromatography-MS techniques so that, for the first time, the acid composition and the mono sulfonic acid isomer distribution are shown.Paper no. S1298 in JSD 6, 151-154 (April 2003).KEY WORDS: C 12 Φ-sulfoxylated methyl ester, composition, derivatization, isomer identification.In our previous work (1), a C 16 Φ-methyl ester sulfonic acid (Φ-MES C 16 ) sample was derivatized by methylation with trimethylorthoacetate in excess to give the dimethylester sulfonate. Different analytical techniques were used to analyze the sample, such as gas chromatography (GC)-mass spectrometry (MS), 1 H nuclear magnetic resonance (NMR), liquid secondary ionization mass spectrometry (LSIMS), and tandem MS. The main conclusions drawn from that investigation were as follows: (i) The SO 3 group was positioned randomly. (ii) GC-MS showed the presence of at least 11 isomers that could not be characterized. (iii) 1 H NMR indicated that the major species present contained one CHSO 3 and one CH 2 CO 2 group, confirmed the presence of different isomers, and suggested the presence of polysulfonates. (iv) LSIMS and LSIMS/MS confirmed the presence of CH 3 (CH 2 ) m CH(SO 3 Me)(CH 2 ) n CH 2 CO 2 Me (M.W. = 364 where m + n = 12); very little α or β substitution; and the presence of polysulfonated species of the forms CH 3 (CH 2 ) m CH(SO 3 Me)(CH 2 ) n CH(SO 3 Me)(CH 2 ) p CH 2 CO 2 Me and CH 3 (CH 2 ) m C(SO 3 Me) 2 (CH 2 ) n CH 2 CO 2 Me. Probably as a result of the instability of the derived methyl esters, the research (1) could not be completed and the identification of each isomer remained a goal to be reached.Therefore, in the present investigation a C 12 fatty acid methyl ester was sulfoxidized with SO 2 , O 2 , and ultraviolet light of 257.3 nm wavelength as described previously (2). The sulfonic acid was further extracted from the reactor outlet product with n-hexane as described previously (3), and a different derivatization technique was applied using potassium iodide and trifluoroacetic anhydride (TFAA) (4).Although the random position hypothesis was confirmed for Φ-MES C 16 (1), the present work describes the sulfonic acid composition and identifies each positional isomer for the first time by means of GC-MS and liquid chromatography (LC)-MS. EXPERIMENTAL PROCEDURESDerivatization of Φ-MES C 12 . According to a method developed by Li and Lin (5) and applied by Pratesi et al. (4), a sulfonic acid methyl ester sample, obtained through sulfoxidation (2) and further hexane extraction (3), was derivatized by the TFAA/potassium iodide method (4), and the derivatives were analyzed by GC-MS and LC-MS [electrospray ionization (ESI) source].In this procedure (4), the sulfonic group is first reduced to an alkyl-thiol group. Then the trifluoroacetic acid group is added to ...

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Separation and extraction of Φ‐methyl ester sulfoxylates: New features

Cited by 15 publications

References 1 publication

Performance of Φ‐Sulfo Fatty Methyl Ester Sulfonate Versus Linear Alkylbenzene Sulfonate, Secondary Alkane Sulfonate and α‐Sulfo Fatty Methyl Ester Sulfonate

Performance of Φ‐Sulfo Fatty Methyl Ester Sulfonate Versus Linear Alkylbenzene Sulfonate, Secondary Alkane Sulfonate and α‐Sulfo Fatty Methyl Ester Sulfonate

Sulfoxylated methyl esters as potential components of liquid formulations

Analysis of sulfoxylated methyl esters (Φ-MES): Sulfonic acid composition and isomer identification

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