Heterogeneous base catalytic transesterification synthesis of sucrose ester and parallel reaction control

Zhao, Rongrong; Chang, Zhidong; Jin, Qiong; Li, Wenjun; Dong, Bin; Miao, Xiaowen

doi:10.1111/ijfs.12376

Cited by 17 publications

(18 citation statements)

References 20 publications

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“…In addition, the reaction rate of mMS2 within first 3 h was much higher than that of sMS2. In comparison to that of sMS2, the final products from mMS2 contained more SE, which was the same as that reported by Zhao et al (). It was reported that a small quantity of sucrose could be dissolved in FAME and the dissolved one would react with liquid FAME on the catalyst surface to form SE.…”

Section: Resultssupporting

confidence: 89%

Efficient Solvent‐Free Synthesis of Sucrose Esters via Sand‐Milling Pretreatment on Solid–Liquid Mixtures

Chen

et al. 2019

J Surfact & Detergents

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A general and efficient method, involving sand‐milling pretreatment and base‐catalyzed transesterification of sucrose and fatty acid methyl ester (FAME), was presented for the solvent‐free synthesis of sucrose esters. A metastable homogeneous paste with a solid particle size of 13 μm (D50) was obtained by milling at 1000 rpm for 1 h. This reaction mixture generated a total SE yield of 88.2% with a methyl stearate (MS) conversion of 91.4% using K2CO3 as a catalyst at 135 °C for 3 h at a stirring rate of 500 rpm, while those without milling (D50, 153 μm) yielded a total sucrose fatty acid esters (SE) of 49.3% with a MS conversion of 83.1% under the same reaction conditions. The reaction kinetics revealed that the reaction mixture with milling pretreatment displays a shorter induction time and a faster reaction rate for the formation of SE. The promotion of the solvent‐free synthesis of SE in the current study could be attributed to the reduction of solid particle sizes and the increased compatibility of solid–liquid phases. We believe that this strategy could be used as a general way for strengthening other heterogeneous reactions in the organic synthesis.

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Section: Resultssupporting

confidence: 89%

Efficient Solvent‐Free Synthesis of Sucrose Esters via Sand‐Milling Pretreatment on Solid–Liquid Mixtures

Chen

et al. 2019

J Surfact & Detergents

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“…As expected, in all experiments the viscosity of the reactive mixture markedly increased as reaction proceeds; this could be an indirect indicator of sucroester formation or sugar caramelization (i.e. for process control) (Deshpande et al, 2013;Le-Coent et al, 2003;Zhao et al, 2014). Reactions were carried out until viscosity hindered proper stirring, so the heat transfer was no longer homogeneous.…”

Section: Resultssupporting

confidence: 60%

“…Since continuous phase of reactive system is non-polar, it could be expected that an oil-soluble emulsifier was more appropriate to induce a stable sucrose-in-FAME suspension. However, Zhao et al 2014 reported that solubility of sucrose in FAME is higher using sucroesters with high HLB.…”

Section: Influence Of Type Of Emulsifiermentioning

confidence: 99%

“…Alkaline and multivalent fatty acid soaps have demonstrated emulsifying action in this reaction (Fitremann et al, 2007;Galleymore et al, 1981;James & Smith, 2009, 2012Le-Coent et al, 2003). Also, sucroesters have been used to improve reactants compatibility (Le-Coent et al, 2003;Zhao et al, 2014). Mono-and diacylglicerol have been also evaluated…”

Section: Chemicals and Reagentsmentioning

confidence: 99%

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Production of sucroesters using solvent-free reactive systems containing emulsifiers

et al. 2018

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The transesterification reaction of sucrose and fatty acid methyl esters to produce sucroesters was experimentally evaluated using commercial emulsifiers as compatibility agents. Reactions were carried out at temperatures between 100 and 140°C, using emulsifier concentrations in the range of 5 to 15 %wt, and potassium carbonate as catalyst. Fatty acid methyl esters consumption and sucroesters production was monitored by HPLC analysis of samples. Methyl esters conversions around 40 % were obtained with 68 %wt monoester content in sucroesters mixture. Despite the reaction times were reduced by operating at high temperatures and high emulsifier's concentration, multiple substitution and color degradation were observed. Higher productivities of sucroester and higher selectivity to monoesters were obtained when potassium palmitate was used as contacting agent. The lower monoester content in the final product was obtained when using a commercial sucroester emulsifier. Results of this study can be used for preliminary process design in a solvent-free production of biobased sucroesters.Keywords: Sucroester, solvent-free, transesterification, emulsifiers, Heterogeneous. RESUMENEn este trabajo se evaluó experimentalmente la reacción de transesterificación entre sacarosa y ésteres metílicos de ácidos grasos para producir ésteres de sacarosa, usando emulsificantes comerciales como agentes de compatibilidad. Las reacciones se llevaron a cabo a temperaturas entre 100 y 140°C, usando concentraciones de emulsionantes en un rango entre 5 y 15%p, y carbonato de potasio como catalizador. El consumo de ésteres metílicos de ácidos grasos y la producción de ésteres de sacarosa fueron seguidos por HPLC. Se obtuvieron conversiones de palmitato de metilo alrededor del 40% y ésteres de sacarosa de 68%p de monoéster. A pesar de que los tiempos de reacción se reducen operando a altas temperaturas y altas concentraciones de emulsionante, se observó que el producto final sufría degradación de color. Las mayores productividades de ésteres de sacarosa y la mayor selectividad hacia monoésteres fueron obtenidas cuando se usó palmitato de potasio como agente de contacto. El menor contenido de monoéster en el producto final fue obtenido usando éster de sacarosa comercial. Los resultados de este estudio pueden ser usados por diseño conceptual preliminar en la producción libre de solvente de ésteres de sacarosa biobasados. How to cite: Gutierrez M. F., Orjuela A., Rivera J. L., Suaza A. (2018). Production of sucroesters using solvent-free reactive systems containing emulsifiers.

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“…ILs and DESs have been described as potential solvents for several reactions in the last 20 years (Yang and Huang, 2012; Nowicki and Muszynski, 2014; Megías-Sayago et al, 2016; Vanda et al, 2018). The third approach involves iterative micellization to drive the molecular organization of the particles and their reactivity (Claverie et al, 2004; Zhao et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

Atypical Reaction Media and Organized Systems for the Synthesis of Low-Substitution Sugar Esters

et al. 2019

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Sugar esters are non-ionic surfactants with amphiphilic properties of interest for the formulation of various products in the fields of detergents, foods, medicines, pharmaceuticals, agriculture, and cosmetics. The properties of sugar esters depend on their degree of substitution (we consider degrees of substitution between 1 and 3 here) which guides their use. Sugar esters are biodegradable and non-toxic, and the demand for these compounds is high and continuing to increase. Indeed, interest in these compounds stems from the natural origin of the raw materials, the synthetic processes involved and the performance of the final product. The choice of reaction medium is crucial, to facilitate contact between reactants and prevent hydrolysis of the products. In this review, we provide an overview of the processes and synthesis routes for sugar ester production, ionic liquids and deep eutectic solvent as non-usual media or with organized systems.

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Heterogeneous base catalytic transesterification synthesis of sucrose ester and parallel reaction control

Cited by 17 publications

References 20 publications

Efficient Solvent‐Free Synthesis of Sucrose Esters via Sand‐Milling Pretreatment on Solid–Liquid Mixtures

Efficient Solvent‐Free Synthesis of Sucrose Esters via Sand‐Milling Pretreatment on Solid–Liquid Mixtures

Production of sucroesters using solvent-free reactive systems containing emulsifiers

Atypical Reaction Media and Organized Systems for the Synthesis of Low-Substitution Sugar Esters

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