# Lactide

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Lactide Names Preferred IUPAC name 3,6-Dimethyl-1,4-dioxan-2,5-dione Other names Dilactid Identifiers CAS Number 4511-42-6 [(S,S)-Lactide] Y 25038-75-9 [(R,R)-Lactide] N 13076-19-2 [(R,S)-Lactide = meso-Lactide] N 26680-10-4 [mixture of three isomers] Y 95-96-5 [mixture of three isomers][1] Y 3D model (JSmol) Interactive image ChemSpider 7002 ECHA InfoCard 100.002.245 EC Number 202-468-3 PubChem CID 7272 UNII IJ13TO4NO1 [(S,S)-Lactide] Y 9J7G894K2M [mixture of three isomers] Y 7EH08MWO6M [mixture of three isomers] Y CompTox Dashboard (EPA) DTXSID7041253 InChI InChI=1S/C6H8O4/c1-3-5(7)10-4(2)6(8)9-3/h3-4H,1-2H3 Key: JJTUDXZGHPGLLC-UHFFFAOYSA-N SMILES CC1C(=O)OC(C(=O)O1)C Properties Chemical formula C6H8O4 Molar mass 144.126 g·mol−1 Melting point 95 to 97 °C (203 to 207 °F; 368 to 370 K) [(S,S)-Lactide and (R,R)-Lactide][2] Solubility in water Hydrolyses to lactic acid[2] Solubility soluble in chloroform, methanol slightly soluble in benzene [2] Hazards GHS labelling: Pictograms Signal word Warning Hazard statements H319 Precautionary statements P264, P280, P305+P351+P338, P337+P313 Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemical compound

**Lactide** is the [lactone](/source/Lactone) [cyclic](/source/Cyclic_compound) [ester](/source/Ester) derived by multiple [esterification](/source/Esterification) between two (usually) or more molecules from [lactic acid](/source/Lactic_acid) (2-hydroxypropionic acid) or other hydroxy carboxylic acid. They are designated as dilactides, trilactides, etc., according to the number of hydroxy acid residues. All lactides are colorless or white solids. The dilactide derived from lactic acid has the formula [CH(CH3)CO2]2. This lactide has attracted interest because it is derived from abundant renewable resources and is the precursor to a biodegradable [plastic](/source/Polylactic_acid).[3]

## Stereoisomers

The dilactide derived from lactic acid can exist in three different [stereoisomeric](/source/Stereoisomeric) forms. This complexity arises because lactic acid is [chiral](/source/Chirality_(chemistry)). These enantiomers do not racemize readily.

(*R*,*R*)-Lactide (left above), (*S*,*S*)-lactide (right above) and *meso*-lactide (below)

All three stereoisomers undergo [epimerisation](/source/Epimerisation) in the presence of organic and inorganic bases in solution.[4]

## Polymerization

Lactide can be [polymerized](/source/Polymerization) to [polylactic acid](/source/Polylactic_acid) (polylactide). Depending on the [catalyst](/source/Catalyst), [syndiotactic](/source/Syndiotactic) or a heterotactic polymers can result. The resulting materials, polylactic acid, have many attractive properties.[5][6]

## References

1. **[^](#cite_ref-SigmaAldrich_1-0)** [Sigma Aldrich product page for lactide](http://www.sigmaaldrich.com/catalog/product/aldrich/303143?lang=en&region=GB) Retrieved 8th of July 2015

1. ^ [***a***](#cite_ref-roempp_2-0) [***b***](#cite_ref-roempp_2-1) [***c***](#cite_ref-roempp_2-2) [Römpp Online Chemielexikon Version 3.3](http://www.roempp.com/prod/index1.html) aufgerufen am 25. März 2009

1. **[^](#cite_ref-Ullmanns_3-0)** Andreas Künkel; Johannes Becker; Lars Börger; Jens Hamprecht; Sebastian Koltzenburg; Robert Loos; Michael Bernhard Schick; Katharina Schlegel; Carsten Sinkel; Gabriel Skupin; Motonori Yamamoto (2016). "Polymers, Biodegradable". *Ullmann's Encyclopedia of Industrial Chemistry*. Weinheim: Wiley-VCH. pp. 1–29. [doi](/source/Doi_(identifier)):[10.1002/14356007.n21_n01.pub2](https://doi.org/10.1002%2F14356007.n21_n01.pub2). [ISBN](/source/ISBN_(identifier)) [978-3-527-30673-2](https://en.wikipedia.org/wiki/Special:BookSources/978-3-527-30673-2).

1. **[^](#cite_ref-4)** Shuklov, Ivan A.; Jiao, Haijun; Schulze, Joachim; Tietz, Wolfgang; Kühlein, Klaus; Börner, Armin (2011-03-02). "Studies on the epimerization of diastereomeric lactides". *Tetrahedron Letters*. **52** (9): 1027–1030. [doi](/source/Doi_(identifier)):[10.1016/j.tetlet.2010.12.094](https://doi.org/10.1016%2Fj.tetlet.2010.12.094). [ISSN](/source/ISSN_(identifier)) [0040-4039](https://search.worldcat.org/issn/0040-4039).

1. **[^](#cite_ref-5)** R. Auras; L.-T. Lim; S. E. M. Selke; H. Tsuji (2010). *Poly(lactic acid): Synthesis, Structures, Properties, Processing, and Applications*. Wiley. [ISBN](/source/ISBN_(identifier)) [978-0-470-29366-9](https://en.wikipedia.org/wiki/Special:BookSources/978-0-470-29366-9).

1. **[^](#cite_ref-6)** Odile Dechy-Cabaret; Blanca Martin-Vaca; Didier Bourissou (2004). "Controlled Ring-Opening Polymerization of Lactide and Glycolide". *Chem. Rev*. **104** (12): 6147–76. [doi](/source/Doi_(identifier)):[10.1021/cr040002s](https://doi.org/10.1021%2Fcr040002s). [PMID](/source/PMID_(identifier)) [15584698](https://pubmed.ncbi.nlm.nih.gov/15584698).

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Adapted from the Wikipedia article [Lactide](https://en.wikipedia.org/wiki/Lactide) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Lactide?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.