Ester

For other uses, see Ester (disambiguation).
An ester of a carboxylic acid. R stands for any group (typically hydrogen or organyl) and R′ stands for any organyl group.

In chemistry, an ester is a compound derived from an acid (organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group (−OH) of that acid is replaced by an organyl group (R′).[1] These compounds contain a distinctive functional group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well.[1] According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well (e.g. amides), but not according to the IUPAC.[1]

Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Lactones are cyclic carboxylic esters; naturally occurring lactones are mainly 5- and 6-membered ring lactones. Lactones contribute to the aroma of fruits, butter, cheese, vegetables like celery and other foods.

Esters can be formed from oxoacids (e.g. esters of acetic acid, carbonic acid, sulfuric acid, phosphoric acid, nitric acid, xanthic acid), but also from acids that do not contain oxygen (e.g. esters of thiocyanic acid and trithiocarbonic acid). An example of an ester formation is the substitution reaction between a carboxylic acid (R−C(=O)−OH) and an alcohol (R'−OH), forming an ester (R−C(=O)−O−R'), where R stands for any group (typically hydrogen or organyl) and R′ stands for organyl group.

Organyl esters of carboxylic acids typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. They perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers,[2] and are one of the largest classes of synthetic lubricants on the commercial market.[3] Polyesters are important plastics, with monomers linked by ester moieties. Esters of phosphoric acid form the backbone of DNA molecules. Esters of nitric acid, such as nitroglycerin, are known for their explosive properties.

There are compounds in which an acidic hydrogen of acids mentioned in this article are not replaced by an organyl, but by some other group. According to some authors, those compounds are esters as well, especially when the first carbon atom of the organyl group replacing acidic hydrogen, is replaced by another atom from the group 14 elements (Si, Ge, Sn, Pb); for example, according to them, trimethylstannyl acetate (or trimethyltin acetate) CH3COOSn(CH3)3 is a trimethylstannyl ester of acetic acid, and dibutyltin dilaurate (CH3(CH2)10COO)2Sn((CH2)3CH3)2 is a dibutylstannylene ester of lauric acid, and the Phillips catalyst CrO2(OSi(OCH3)3)2 is a trimethoxysilyl ester of chromic acid (H2CrO4).[4][5]

  1. ^ a b c IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "esters". doi:10.1351/goldbook.E02219
  2. ^ Cameron Wright (1986). A worker's guide to solvent hazards. The Group. p. 48. ISBN 9780969054542.
  3. ^ E. Richard Booser (21 December 1993). CRC Handbook of Lubrication and Tribology, Volume III: Monitoring, Materials, Synthetic Lubricants, and Applications. CRC. p. 237. ISBN 978-1-4200-5045-5.
  4. ^ "Acetoxytrimethyltin".
  5. ^ "Trimethyltin acetate | C5H12O2Sn | ChemSpider".