Abstract
During interesterification, fatty acid moieties are reshuffled over the glycerol backbone of the triglycerides. The reaction requires a catalyst, which can be an alkali, such as sodium methoxide, or a lipase enzyme. The reaction has been used to produce fat substitutes (products that feel and taste like fat but are hardly digested, or not at all). Since at one stage, industry considered these fat substitutes to be promising products, several patent applications were filed; they are discussed in a separate section of this chapter. Another area that led to applications being filed is the use of enzymes. These can have a certain specificity, but because of acyl migration within partial glycerides, even the use of enzymes displaying positional specificity eventually leads to randomization. Patents disclosing attempts to lengthen enzyme half-life will also be discussed.
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- 1.
The nomenclature of the various reactions is far from uniform. When I worked in a polyester polymer plant, we described the reaction between dimethylterephthalate and ethylene glycol as an “ester interchange”; in the edible oil sector this is called an “interesterification.” When this reaction takes place within a triglyceride molecule, it can be referred to as “intraesterification,” but when this happens in a partial glyceride, it is called “acyl migration.” Enzymatic interesterification can also be referred to as “enzymatic rearrangement” (Ten Brink et al. 2006).
The process to produce FAME by reacting oil with methanol is commonly referred to as “transesterification” but can also be called “methanolysis.” Producing partial glycerides by reacting triglyceride oil with glycerol is usually called “glycerolysis.” When the hydrolysis reaction to produce free fatty acids and glycerol is carried out industrially, it is called “fat splitting.” “Acidolysis” refers to the replacement of a fatty acid moiety in a triglyceride molecule by another carboxylic acid, and esterifying a free hydroxyl group with a fatty acid is called “esterification,” but “reverse hydrolysis” has also been used (Schneider et al. 1996). However, the process in which free fatty acids and partial glycerides present in a crude or degummed oil are esterified has also been referred to as “remediation” (Cowan 2011) or “reforming” (Matsuzaki et al. 1991).
- 2.
When my boss asked me if my department had an answer to Olestra, I answered, “Mr. Raymond, this is a typical P&G product since this company is big in detergents and Pampers.”
- 3.
In the literature, these compounds are also referred to as dialkylketones. They can be formed as byproducts of the interesterification reaction. They were apparently a hot topic since searching for “difatty ketones” at www.google.com/patents results in nine P&G patents being listed.
- 4.
The patent (Sparsø and Engelrud 2004) has been assigned to Danisco A/S, a company that has experience with molecular distillation to isolate monoglycerides. Danisco is now part of E.I. du Pont de Nemours and Company.
- 5.
Would that be because of my Letter to the Editor, which convinced him that blending is cheaper?
- 6.
This company is now part of BASF.
- 7.
I had a look at the BASF websites and did not find any reference to this catalyst.
- 8.
This may be because Prof, Peter, who assigned his many patents to himself, passed away.
- 9.
I use the program ReferenceManager, which is now run by Thomson Reuters; I am quite pleased with it.
- 10.
The title mentions “transesterification,” but as explained before, this term is used today only to describe a process in which triglycerides are allowed to react with lower alcohols.
- 11.
Although this patent has a full page with corrections of typing errors, the title reading miehe instead of miehei has not been corrected.
- 12.
His presentation and others are available at http://www.soci.org/News/lipids-enzymatic-2011
- 13.
Presumably, Corman had to pay the European fees twice, which explains why it is uncommon for the EPO to publish the same invention twice.
- 14.
The specification is not well written. When discussing the dry degumming of shea butter in the example, it mentions an “acetic bleaching earth” instead of an “acid-activated bleaching earth.” This is not a typing error, but a lack of comprehension.
- 15.
When describing a range, I always put the lowest values first. So I would have written –15 to –10°C rather than “preferably –10 to –15°C.”
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Dijkstra, A.J. (2013). Interesterification. In: Edible Oil Processing from a Patent Perspective. Springer, Boston, MA. https://doi.org/10.1007/978-1-4614-3351-4_11
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