Transesterification

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Transesterification

In organic chemistry

Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
, transesterification is the process of exchanging the alcohol group of an ester compound with another alcohol

Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
. These reactions are often catalyzed by the addition of an acid

Acid

An acid is traditionally considered any chemical compound that, when dissolved in water, gives a solution with a hydrogen ion Activity greater than in pure water, i.e....
or base

Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
.

Acids can catalyse the reaction by donating a proton to the carbonyl

Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bond to an oxygen atom : C=O.The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex ; in this situation, carbon is triple-bonded to oxygen : C=O....
group, thus making it more reactive, while bases can catalyse the reaction by removing a proton from the alcohol, thus making it more reactive.

Transesterification is used in the synthesis of polyester

Polyester

Polyester is a category of polymers which contain the ester functional group in their main chain. Although there are many polyesters, the term "polyester" as a specific material most commonly refers to polyethylene terephthalate ....
, in which diesters undergo transesterification with diols to form macromolecules.

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Encyclopedia

In organic chemistry

Organic chemistry

Alcohol

Acid

An acid is traditionally considered any chemical compound that, when dissolved in water, gives a solution with a hydrogen ion Activity greater than in pure water, i.e....
or base

Base (chemistry)

Carbonyl

Polyester

Dimethyl terephthalate

Dimethyl terephthalate is an ester of terephthalic acid and methanol and is used in the production of polyesters, including polyethylene terephthalate and polytrimethylene terephthalate....
and ethylene glycol

Ethylene glycol

Ethylene glycol is an alcohol with two -OH groups , a chemical compound widely used as an automobile antifreeze. In its pure form, it is an odorless, colorless, syrupy, sweet tasting, toxic liquid....
react to form polyethylene terephthalate

Polyethylene terephthalate

Polyethylene tephthalate , commonly abbreviated PET, PETE, or the obsolete PETP or PET-P), is a thermoplastic polymer resin of the polyester family and is used in synthetic fibers; beverage, food and other liquid Packaging; thermoforming applications; and engineering resins often in combination with glass fiber....
and methanol

Methanol

Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a chemical compound with chemical formula carbonhydrogen3oxygenhydrogen ....
, which is evaporated to drive the reaction forward. The reverse reaction (methanolysis) is also an example of transesterification, and has been used to recycle polyesters into individual monomers (see plastic recycling

Plastic recycling

Plastic recycling is the process of recovering scrap or waste plastics and reprocessing the material into useful products, sometimes completely different in form from their original state....
).

History of biolipid transesterification

One of the first uses of transesterified vegetable oil (biodiesel

Biodiesel

Biodiesel refers to a non-petroleum-based diesel fuel consisting of long chain alkyl esters, made by transesterification of vegetable oil or animal fat , which can be used in unmodified diesel-engine vehicles....
) was to power heavy-duty vehicles in South Africa before World War II

World War II

Patent

A patent is a set of exclusive rights granted by a state to an inventor or his assignee for a term of patent in exchange for a disclosure of an invention....
ed in the U.S.

United States

The United States of America is a Federal government constitutional republic comprising U.S. state and a federal district. The country is situated mostly in central North America, where its Contiguous United States and Washington, D.C., the Capital districts and territories, lie between the Pacific Ocean and Atlantic Oceans, Borders of the U...
in the 1940s by Colgate

Colgate

Colgate may refer to:...
, though biolipid transesterification may have been discovered much earlier. In the 1940s, researchers were looking for a method to more readily produce glycerine, which was used to produce explosives for World War II

World War II

World War II, or the Second World War , was a global military conflict which involved a Participants in World War II, including all of the great powers, organised into two opposing military alliances: the Allies of World War II and the Axis powers....
. Many of the methods used today by producers and homebrewers have their origin in the original 1940s research.

Biolipid transesterification has also been recently shown by Japanese researchers to be possible using a super-critical methanol methodology, whereby high temperature, high-pressure vessels are used to physically catalyze the biolipid/methanol reaction into fatty-acid methyl esters.

Transesterification

History of biolipid transesterification

See also