Revisiting the mechanisms of low-temperature, base-catalysed ester interchange reactions

Dijkstra, Albert J.

doi:10.1051/ocl.2008.0200

Cited by 8 publications

(10 citation statements)

References 8 publications

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“…Baltes found that sodium diacylglycerolate is formed after adding the catalyst, and he suggested a mechanism in which this compound serves as an active intermediate of the interesterification reaction (Dijkstra 2008). An enolate mechanism that has been suggested by Dijkstra (Dijkstra 2004;Dijkstra, Tőke et al 2005) incorporates all of these earlier suggestions and observations and provides an adequate explanation and illustration of these data as presented in [Fig 6].…”

Section: Mechanism and Kineticsmentioning

confidence: 84%

Edible lipids modification processes: A review

Kadhum

Shamma

2015

Critical Reviews in Food Science and Nutrition

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Lipid is the general name given to fats and oils, which are the basic components of cooking oils, shortening, ghee, margarine, and other edible fats. The chosen term depends on the physical state at ambient temperature; fats are solids and oils are liquids. The chemical properties of the lipids, including degree of saturation, fatty acid chain length, and acylglycerol molecule composition are the basic determinants of physical characteristics such as melting point, cloud point, solid fat content, and thermal behavior. This review will discuss the major lipid modification strategies, hydrogenation, and chemical and enzymatic interesterification, describing the catalysts used mechanisms, kinetics, and impacts on the health-related properties of the final products. Enzymatic interesterification will be emphasized as method that produces a final product with good taste, zero trans fatty acids, and a low number of calories, requires less contact with chemicals, and is cost efficient.

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Section: Mechanism and Kineticsmentioning

confidence: 84%

Edible lipids modification processes: A review

Kadhum

Shamma

2015

Critical Reviews in Food Science and Nutrition

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“…A final remark must be made about the base‐catalyzed interesterification process itself. It has been noted (Dijkstra, ) that a number of different catalytic intermediates are involved. When triacylglycerols are interesterified, the main intermediate is the enolate anion but when biodiesel is made by transesterification, the methanolate anion is involved.…”

Section: Discussionmentioning

confidence: 99%

Estimating the Composition of Interesterification Products Made from Triacylglycerol Oil with Glycerol and/or Propylene Glycol

Dijkstra

2019

J Americ Oil Chem Soc

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Thanks to the development of personal computers and software, it is often faster and, therefore, cheaper to calculate product properties than to determine them analytically, but such calculations are only possible after the appropriate mathematical equations have been formulated. Formulating these equations may use some assumptions and parameters that have been determined experimentally. This article describes a method of calculating the composition of the ester interchange reaction product of triacylglycerol oil with glycerol and/or propylene glycol; it can be extended to include further polyols. The calculation requires the composition of the starting material, the saponification and hydroxyl values of the oil, and three parameters indicating how the fatty acid distribution in the reaction product deviates from random. These parameters are not known but can be quantified by combining the method of calculation described in this article and some analytical results.

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“…First, the concentration of fatty acid groups is much higher than those of methanol and partial glycerides, and second, as illustrated before, the enolate anion is stabilized by resonance which makes the α‐hydrogen bond strength less than those in the free hydroxyl groups. In Figure , [ 16 ] I have tried to indicate by the thickness of the arrows what the equilibrium constants could look like.…”

Section: Equilibrium Between Various Anionsmentioning

confidence: 99%

Some Thoughts on the Mechanism of Ester Interchange Reactions Involving Acylglycerols

Dijkstra¹

2020

Euro J Lipid Sci & Tech

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Ester interchange reactions involving acylglycerides are industrially important because the interesterification process provides trans-isomer free hardstocks and the transesterification process produces biodiesel. This Commentary proposes to extend the enolate mechanism that has been suggested for the interesterification process to the transesterification process. It also highlights the gaps in people's knowledge and discusses the implication of these gaps. Practical Applications: Insight into the mechanism of the interesterification reaction provides means to eliminate the yield loss suffered by the current industrial processes. Use of an alkali metal glycerolate will avoid the formation of fatty acid methyl esters and their subsequent loss. Using the same catalyst during the transesterification will reduce the variable cost of this process since this catalyst can be easily produced on site from by-product glycerol.

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Revisiting the mechanisms of low-temperature, base-catalysed ester interchange reactions

Cited by 8 publications

References 8 publications

Edible lipids modification processes: A review

Edible lipids modification processes: A review

Estimating the Composition of Interesterification Products Made from Triacylglycerol Oil with Glycerol and/or Propylene Glycol

Some Thoughts on the Mechanism of Ester Interchange Reactions Involving Acylglycerols

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