Studies on Sulfonation of Esters of Fatty Acids by a Continuous Thin Film Sulfonator and its Initial Reaction Products

Nagayama, Masuzō; Okumura, Osamu; Sakatani, Takenobu; Hashimoto, Shigeru; Noda, Satoshi

doi:10.5650/jos1956.24.395

Cited by 6 publications

(8 citation statements)

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“…Generally, the SO 3 is diluted with N 2 or air to concentrations of 5–10% to reduce reactivity and avoid strong reaction. ,,, Figure shows the effect of N 2 flow rates in the range from 50 to 900 mL/min. The increase in the N 2 flow rate leads to almost no change in the ME conversion and α-MES concentration, suggesting no dependence of the reaction on the SO 3 concentration.…”

Section: Resultsmentioning

confidence: 99%

“…Thus, the falling film reactors (FFRs), widely used for gas–liquid absorption and reaction processes such as sulfonation, chlorination, ethoxylation, and photocatalysis, − were consequently employed in this reaction for high capacity of mass and heat transfer and low pressure drop in the reactor. Various raw materials, such as methyl stearate and ME derived from coconut, palm kernel, palm stearin, tallow, and soya, were used. The sulfonations were usually conducted with a SO 3 -to-ME molar ratio of 1.2–1.3 and diluted SO 3 by air (about 7 vol %) at 50–100 °C.…”

Section: Introductionmentioning

confidence: 99%

“…Microchannels were not used for aging because of high viscosity of the resultant sulfonated ME. We thus elucidated the reaction process in the FFMR, based on the widely accepted reaction mechanism of sulfonation of ME with SO 3 ,,,− shown in the Scheme . Briefly, the ME ( I ) reacts fast with SO 3 adding to the carbonyl oxygen to form intermediate II , which is then quickly changed to intermediate III with a SO 3 -to-ME stoichiometry of 2:1.…”

Section: Introductionmentioning

confidence: 99%

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Preparation of Methyl Ester Sulfonates Based on Sulfonation in a Falling Film Microreactor from Hydrogenated Palm Oil Methyl Esters with Gaseous SO₃

Xie

Zeng

Wang

et al. 2013

Ind. Eng. Chem. Res.

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Fatty acid methyl ester sulfonate (MES) is an environmentally friendly anionic surfactant. It contains RCH(CO2Me)SO3Na (α-MES) as the active component and RCH(CO2Na)SO3Na (the disodium salt) whose content must be lower than 5%. In this paper, MES was prepared first in a falling film microreactor (FFMR) by sulfonation of hydrogenated palm oil methyl ester (ME) with SO3 diluted with N2, followed by aging in a tubular reactor and subsequent bleaching and neutralization with NaOH. The influences of the ME flow rate, the channel size, the N2 flow rate, the SO3-to-ME molar ratio, and the sulfonation temperature in the sulfonation step, as well as the influences of the SO3-to-ME molar ratio, the aging residence time, and the aging temperature in the aging step, were all examined. The results indicated that the ME flow rate had no evident influence on the ME conversion and the α-MES concentration both without overflow and with overflow. In the sulfonation step, the disodium salt (disalt) concentration increased with increase in the ME flow rate, the channel size, the SO3-to-ME molar ratio, and the sulfonation temperature or decrease in the N2 flow rate. In the aging step, the ME conversion, the α-MES concentration, and the disalt concentration increased with increase in the SO3-to-ME molar ratio, the aging residence time, and the aging temperature. The results of 1H NMR spectra indicated that RCH(CO2Me)SO3H was mainly formed in the sulfonation step in the microreactor, while it was formed in the aging step when the sulfonation was carried out in the conventional falling film reactor. Accordingly, a sulfonation reaction mechanism in the FFMR different from that in the conventional FFR was proposed. The final products with an α-MES concentration of 86.3% and a disalt concentration of 1.2% were obtained under the conditions of a ME flow rate of 2 mL/min, a channel size of 300 × 100 μm, a SO3-to-ME molar ratio of 1.2, a N2 flow rate of 900 mL/min, a sulfonation temperature of 85 °C, an aging temperature of 90 °C, and an aging residence time of 19.7 min.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Preparation of Methyl Ester Sulfonates Based on Sulfonation in a Falling Film Microreactor from Hydrogenated Palm Oil Methyl Esters with Gaseous SO₃

Xie

Zeng

Wang

et al. 2013

Ind. Eng. Chem. Res.

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“…Fatty acid methyl ester sulfonate (MES) is synthesized easily from natural oil and fat resources such as palm oil and coconut oil, and is widely used as an ecofriendly and attractive detergent from the viewpoint of sustainability. There have been many reports on the sulfonation mechanism of fatty acid methyl ester (ME) [1][2][3][4][5][6][7]. As shown in Scheme 1, Yoshimura and Matsutani proposed that ME reacted with SO 3 to give a 1:1 (ME:SO 3 ) adduct (step 1), which was then converted to a 1:2 adduct (step 2), and finally yielded MES through the release of SO 3 (step 3).…”

Section: Introductionmentioning

confidence: 99%

“…As shown in Scheme 1, Yoshimura and Matsutani proposed that ME reacted with SO 3 to give a 1:1 (ME:SO 3 ) adduct (step 1), which was then converted to a 1:2 adduct (step 2), and finally yielded MES through the release of SO 3 (step 3). The rate-limiting step of this reaction is step (3), and an aging process at a high temperature is required after SO 3 addition in order to complete the reaction.…”

Section: Introductionmentioning

confidence: 99%

Coloration Process in the Sulfonation of Fatty Acid Methyl Ester with Sulfur Trioxide

Niikura

Omine

Kimura

et al. 2013

J Americ Oil Chem Soc

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Fatty acid methyl ester sulfonate (MES), an anionic surfactant suitable as a laundry detergent, is produced commercially by the direct sulfonation of fatty acid methyl ester (ME) with SO 3 . However, intense coloration occurs during the sulfonation process. The sulfonation of ME was performed through the addition of SO 3 (SO 3 /ME molar ratio = 0.8-1.2) for 1-4 h and subsequent aging for 1 h at 80°C. Even when the amount of unsaturated bonds in ME was reduced to give an iodine value (IV) of less than 0.01, coloration occurred during the sulfonation, making the unbleached product unsuitable for commercial use. The formation of olefinic units and SO 2 was observed during the reaction, and the color of the reaction mixture was strongly correlated with their amounts. Further analysis confirmed that equimolar amounts of the olefinic unit and SO 2 were formed, and the rate profiles of the formation of MES and SO 2 agreed well with each other. From these observations, we concluded that the coloration of the reaction mixture was caused by oxidation of the alkyl chain with SO 3 during the liberation of SO 3 from the 1:2 adduct of ME and SO 3 , a key intermediate in the sulfonation process.Keywords Sulfonation Á Fatty acid methyl ester Á Coloration Á Sulfur trioxide Á Sulfur dioxide Á Olefinic unit Á Bleach Á Palm oil Abbreviations MES Fatty acid methyl ester sulfonate ME Fatty acid methyl ester IV Iodine value Fig. 11 Relation between the rates of formation of MES (black triangles) and SO 2 (black squares). Sulfonation of ME was carried out through addition of SO 3 for 2 h and subsequent aging for 1 h at 80°C with a SO 3 /ME molar ratio of 1.2 Scheme 2 Formation process of olefinic units J Am Oil Chem Soc (2013) 90:903-909 909

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Influence of process conditions on the sulfonation of methyl ester synthesized from used cooking oil: Optimization by Taguchi approach

Bode‐Olajide

Yusuff

Adesina

et al. 2023

J Surfact & Detergents

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Developing a robust and facile process route for fatty acid methyl ester sulfonate (MES) synthesis is of importance for industrial applications. Herein, Taguchi orthogonal array (OA) approach was used for the first time to establish the optimum process condition for the sulfonation of methyl esters (ME) with chlorosulfonic acid (CSA). According to the experimental design, the most significant parameter was sulfonation temperature, followed by CSA/ME molar ratio. Under the optimum sulfonation conditions (that is, 70°C sulfonation temperature, 2.0 h sulfonation time, 1.5:1 mol/mol CSA/ME molar ratio and 2.0 h aging time), the MES yield and the corresponding signal/noise ratio were 92.08 ± 0.28% and 39.28, respectively. The obtained FTIR and 1H NMR data revealed spectra associated with methyl (CH2 asymmetric and CH2 symmetric stretching vibrations), esters (CO, CO, and OCH3), and sulfonate (SO) groups in the MES sample synthesized under optimal conditions, thus confirming the target MES product. Surface tension measurements revealed that the optimal MES sample had a low critical miscelle concentration of 0.082 g/L at a surface tension of 51.2 mN/m, implying the possibility of better performance.

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Studies on Sulfonation of Esters of Fatty Acids by a Continuous Thin Film Sulfonator and its Initial Reaction Products

Cited by 6 publications

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Preparation of Methyl Ester Sulfonates Based on Sulfonation in a Falling Film Microreactor from Hydrogenated Palm Oil Methyl Esters with Gaseous SO₃

Preparation of Methyl Ester Sulfonates Based on Sulfonation in a Falling Film Microreactor from Hydrogenated Palm Oil Methyl Esters with Gaseous SO₃

Coloration Process in the Sulfonation of Fatty Acid Methyl Ester with Sulfur Trioxide

Influence of process conditions on the sulfonation of methyl ester synthesized from used cooking oil: Optimization by Taguchi approach

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Studies on Sulfonation of Esters of Fatty Acids by a Continuous Thin Film Sulfonator and its Initial Reaction Products

Cited by 6 publications

References 0 publications

Preparation of Methyl Ester Sulfonates Based on Sulfonation in a Falling Film Microreactor from Hydrogenated Palm Oil Methyl Esters with Gaseous SO3

Preparation of Methyl Ester Sulfonates Based on Sulfonation in a Falling Film Microreactor from Hydrogenated Palm Oil Methyl Esters with Gaseous SO3

Coloration Process in the Sulfonation of Fatty Acid Methyl Ester with Sulfur Trioxide

Influence of process conditions on the sulfonation of methyl ester synthesized from used cooking oil: Optimization by Taguchi approach

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Preparation of Methyl Ester Sulfonates Based on Sulfonation in a Falling Film Microreactor from Hydrogenated Palm Oil Methyl Esters with Gaseous SO₃

Preparation of Methyl Ester Sulfonates Based on Sulfonation in a Falling Film Microreactor from Hydrogenated Palm Oil Methyl Esters with Gaseous SO₃