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20-September-2008 09:55:59 - Diol Ethylene glycol, a simple diol Ethylene glycol, a simple diol A diol or glycol is a chemical compound containing two hydroxyl groups -OH groups 1 Vicinal diols have hydroxyl groups attached to adjacent atoms. Examples of vicinal diol compounds are ethylene glycol and propylene glycol. Geminal diols have hydroxyl groups bonded to the same atom. In general, organic geminal diols readily dehydrate to form a carbonyl group. For example, carbonic acid HO2C=O is unstable and has a tendency to convert to carbon dioxide CO2 and water H2O. Nevertheless, in rare situations the chemical equilibrium is in favor of the geminal diol. For example, when formaldehyde H2C=O is dissolved in water the geminal diol H2COH2, methanediol, is favored. Examples of diols in which the hydroxyl functional groups are more widely separated include 1,4-butanediol and bisphenol A. Contents 1 Synthesis of diols 2 Reactions 3 See also 4 References Synthesis of diols Because diols are a common functional group arrangement, numerous methods of preparation have been developed. Vicinal diols can be produced from the oxidation of alkenes, usually with dilute acidic potassium permanganate, also known as potassium manganateVII. Using alkaline potassium manganateVII produces a colour change from clear deep purple to clear green; acidic potassium manganateVII turns clear colourless. Osmium tetroxide can similarly be used to oxidize alkenes to vicinal diols. hydrogen peroxide reacts with an alkene to the epoxide and then by saponification to the diol for example in the synthesis of trans-cyclohexanediol batch 2 or by microreactor 3: cyclohexanediol synthesis A chemical reaction called Sharpless asymmetric dihydroxylation can be used to produce chiral diols from alkenes using an osmate reagent and a chiral catalyst. Another method is the Woodward cis-hydroxylation cis diol and the related Prévost reaction anti diol, depicted below, which both use iodine and the silver salt of a carboxylic acid. Prevost reaction In the Prins reaction 1,3-diols can be formed in a reaction between an alkene and formaldehyde. Reactions A diol reacts like an alcohol, such as esterification and ether formation. Diols such as ethylene glycol are used as co-monomers in polymerization reactions forming polymers including some polyesters and polyurethanes. A different monomer with two identical functional groups, such as a dioyl dichloride or dioic acid is required to continue the process of polymerization through repeated esterification processes. In glycol cleavage, the C-C bond in a vicinal diol is cleaved with formation of ketone or aldehyde functional groups. See also Alcohols, chemical compounds with one hydroxyl group Triols, chemical compounds with three hydroxyl group Polyols, chemical compounds with multiple hydroxyl groups References ^ March, Jerry 1985. Advanced Organic Chemistry, Reactions, Mechanisms and Structure, third ion, John Wiley Sons. ISBN 0-471-85472-7. ^ trans-cyclohexanediol Organic Syntheses, Coll. Vol. 3, p.217 1955; Vol. 28, p.35 1948 http://www.orgsynth.org/orgsyn/pdfs/CV3P0217.pdf. ^ Advantages of Synthesizing trans-1,2-Cyclohexanediol in a Continuous Flow Microreactor over a Standard Glass Apparatus Andreas Hartung, Mark A. Keane, and Arno Kraft J. Org. Chem. 2007, 72, 10235-10238 doi:10.1021/jo701758p Retrieved from http://en..org/wiki/Diol Categories: Functional groups | Polyols Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Italiano Nederlands 日本語 Polski Português РуÑ?Ñ?кий Suomi Svenska ä¸æ–‡ This page was last modified on 2 June 2008, at 07:16
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