organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...

glycerolysis refers to any process in which chemical bonds are broken via a reaction with

glycerol Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...

. The term refers almost exclusively to the

transesterification Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. Strong acids catalyze the r ...

reaction of glycerol with

triglyceride A triglyceride (from '' tri-'' and '' glyceride''; also TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates ...

s (fats/oils) to form mixtures of

monoglyceride Monoglycerides (also: acylglycerols or monoacylglycerols) are a class of glycerides which are composed of a molecule of glycerol linked to a fatty acid via an ester bond. As glycerol contains both primary and secondary alcohol groups two differe ...

s and

diglyceride A diglyceride, or diacylglycerol (DAG), is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Two possible forms exist, 1,2-diacylglycerols and 1,3-diacylglycerols. Diglycerides are ...

s. These find a variety of uses; as food

emulsifiers An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Although ...

(e.g. E471), 'low fat' cooking oils (e.g.

diacylglycerol oil Diacylglycerol oil (DAG oil) is a cooking oil in which the ratio of triglycerides, also known as Triacylglycerols (TAGs), to diacylglycerols (DAGs) is shifted to contain mostly DAG, unlike conventional cooking oils, which are rich in TAGs. Vegeta ...

) and

surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...

s (such as monolaurin). The transesterification process gives a complex mixture of products, however not all of these are of equivalent use. This has led to the development of optimized processes able to produce better defined products; in particular by using

enzymes An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as pro ...

, reactions in

supercritical carbon dioxide Supercritical carbon dioxide (s) is a fluid state of carbon dioxide where it is held at or above its critical temperature and critical pressure. Carbon dioxide usually behaves as a gas in air at standard temperature and pressure (STP), or a ...

and flow chemistry. The production of diglycerides (often called diacylglycerols or DAGs) have been investigated extensively due to their use in foods, with total annual sales of approximately US$200 million in Japan since its introduction in the late 1990s until 2009.

References

{{Reflist Carboxylate esters Lipids Organic reactions

See also

References