:Glycerolysis
{{Distinguish|Glycolysis}}
File:Acetates-of-glycerol-2D-skeletal.png
In organic chemistry glycerolysis refers to any process in which chemical bonds are broken via a reaction with glycerol. The term refers almost exclusively to the transesterification reaction of glycerol with triglycerides (fats/oils) to form mixtures of monoglycerides and diglycerides. These find a variety of uses; as food emulsifiers (e.g. E471), 'low fat' cooking oils (e.g. diacylglycerol oil) and surfactants (such as monolaurin).
The transesterification process gives a complex mixture of products, however not all of these are of equivalent use.{{cite journal|last1=Sonntag|first1=Norman O. V.|title=Glycerolysis of fats and methyl esters — Status, review and critique|journal=Journal of the American Oil Chemists' Society|volume=59|issue=10|year=1982|pages=795A–802A|issn=0003-021X|doi=10.1007/BF02634442}} This has led to the development of optimized processes able to produce better defined products; in particular by using enzymes,{{cite journal|last1=Phuah|first1=Eng-Tong|last2=Tang|first2=Teck-Kim|last3=Lee|first3=Yee-Ying|last4=Choong|first4=Thomas Shean-Yaw|last5=Tan|first5=Chin-Ping|last6=Lai|first6=Oi-Ming|title=Review on the Current State of Diacylglycerol Production Using Enzymatic Approach|journal=Food and Bioprocess Technology|volume=8|issue=6|year=2015|pages=1169–1186|issn=1935-5130|doi=10.1007/s11947-015-1505-0|url=http://psasir.upm.edu.my/id/eprint/46178/1/Review%20on%20the%20current%20state%20of%20diacylglycerol%20production%20using%20enzymatic%20approach.pdf}} reactions in supercritical carbon dioxide and flow chemistry.{{cite journal|last1=Junior|first1=Ivaldo I.|last2=Flores|first2=Marcela C.|last3=Sutili|first3=Felipe K.|last4=Leite|first4=Selma G. F.|last5=de M. Miranda|first5=Leandro S.|last6=Leal|first6=Ivana C. R.|last7=de Souza|first7=Rodrigo O. M. A.|title=Lipase-Catalyzed Monostearin Synthesis under Continuous Flow Conditions|journal=Organic Process Research & Development|volume=16|issue=5|year=2012|pages=1098–1101|issn=1083-6160|doi=10.1021/op200132y}} 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.{{cite journal|last1=Lo|first1=Seong-Koon|last2=Tan|first2=Chin-Ping|last3=Long|first3=Kamariah|last4=Yusoff|first4=Mohd. Suria Affandi|last5=Lai|first5=Oi-Ming|title=Diacylglycerol Oil—Properties, Processes and Products: A Review|journal=Food and Bioprocess Technology|volume=1|issue=3|year=2008|pages=223–233|issn=1935-5130|doi=10.1007/s11947-007-0049-3|url=http://psasir.upm.edu.my/id/eprint/14039/1/Diacylglycerol%20oil%20properties.pdf}}