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 materials, i.e., matter in its various forms that contain carbon atoms.Clay ...

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

glycerol Glycerol (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids know ...

. The term refers almost exclusively to the

transesterification In organic chemistry, transesterification is the process of exchanging the organic 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. The reaction ca ...

reaction of glycerol with

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

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. DAGs can act as ...

s. These find a variety of uses; as food emulsifiers (e.g.

E471 Mono- and diglycerides of fatty acids ( E471) refers to a naturally occurring class of food additive composed of diglycerides and monoglycerides which is used as an emulsifier. It is also used as a fruit coating agent. This mixture is also some ...

), 'low fat' cooking oils (e.g. diacylglycerol oil) and

surfactant Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, fo ...

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, 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 In flow chemistry, a chemical reaction is run in a continuously flowing stream rather than in batch production. In other words, pumps move fluid into a reactor, and where tubes join one another, the fluids contact one another. If these fluids ar ...

. 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