Information about Glycol
A diol or glycol is a chemical compound containing two hydroxyl groups (-OH groups). 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 ((HO)2C=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 (H2C(OH)2), methanediol, is favored.
Examples of diols in which the hydroxyl functional groups are more widely separated include 1,4-butanediol and bisphenol A.
Examples of diols in which the hydroxyl functional groups are more widely separated include 1,4-butanediol and bisphenol A.
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 manganate(VII). Using alkaline potassium manganate(VII) produces a colour change from clear deep purple to clear green; acidic potassium manganate(VII) turns clear colourless.
- Osmium tetroxide can similarly be used to oxidize alkenes to vicinal diols.
- A chemical reaction called Sharpless bishydroxylation can be used to produce chiral diols from alkenes using an osmate reagent and a chiral catalyst.
- Another method is the Woodward cis-hydroxylation.
- 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
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Hydroxyl in chemistry stands for a molecule consisting of an oxygen atom and a hydrogen atom connected by a covalent bond. The neutral form is a hydroxyl radical and the hydroxyl anion is called a hydroxide.
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vicinal (from Latin vicinus = neighbour) stands for any two functional groups bonded to two adjacent carbon atoms. For example the molecule 2,3-dibromobutane carries two vicinal bromine atoms and 1,3-dibromobutane does not.
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Ethylene glycol (monoethylene glycol (MEG), IUPAC name: ethane-1,2-diol) is an alcohol with two -OH groups (a diol), a chemical compound widely used as an automotive antifreeze.
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Propylene glycol, known also by the systematic name propane-1,2-diol, is an organic compound (a diol alcohol), usually a tasteless, odorless, and colorless clear oily liquid that is hygroscopic and miscible with water, acetone, and chloroform.
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In chemistry, the term geminal (from Latin gemini = twins) refers to the relationship between two functional groups that are attached to the same atom. The prefix gem is applied to a chemical name to denote this relationship, as in a gem-dibromide.
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dehydration reaction is usually defined as a chemical reaction that involves the loss of water from the reacting molecule. Dehydration reactions are a subset of elimination reactions.
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carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O.
The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.g.
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The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.g.
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Carbonic acid (ancient name acid of air or aerial acid) has the formula H2CO3. It is also a name sometimes given to solutions of carbon dioxide in water, which contain small amounts of H2CO3.
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Carbon dioxide is a chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom. It is a gas at standard temperature and pressure and exists in Earth's atmosphere in this state.
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chemical equilibrium is the state in which the chemical activities or concentrations of the reactants and products have no net change over time. Usually, this state results when the forward chemical process proceeds at the same rate as their reverse reaction.
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Formaldehyde (methanal) is the chemical compound with the formula H2CO. The simplest aldehyde, it was first synthesized by the Russian chemist Aleksandr Butlerov but was conclusively identified by August Wilhelm von Hofmann.
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Water (H2O, HOH) is the most abundant molecule on Earth's surface, composing of about 70% of the Earth's surface as liquid and solid state in addition to being found in the atmosphere as a vapor.
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Methanediol, also known as dihydroxymethane, formaldehyde monohydrate, or methylene glycol is a chemical compound that occurs primarily as the product of formaldehyde in water solution. Its chemical formula is H2C(OH)2.
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1,4-Butanediol is an alcohol derivative of the alkane butane, carrying two hydroxyl groups. It is a colorless viscous liquid.
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Synthesis
Its industrial synthesis starts with acetylene, which is reacted with two molecules of formaldehyde to form 1,4-butynediol, also..... Read more.
Bisphenol A is a chemical compound containing two phenol functional groups. It belongs to the phenol class of aromatic organic compounds. It is widely prepared and sold and various important polymers/plastics are made from it.
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Redox (shorthand for reduction/oxidation reaction) describes all chemical reactions in which atoms have their oxidation number (oxidation state) changed.
This can be either a simple redox process such as the oxidation of carbon to yield carbon dioxide, or the
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This can be either a simple redox process such as the oxidation of carbon to yield carbon dioxide, or the
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alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond. The simplest alkenes, with only one double bond and no other functional groups, form a homologous series of hydrocarbons with the general formula
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ACID (Atomicity, Consistency, Isolation, Durability) is a set of properties that guarantee that database transactions are processed reliably. In the context of databases, a single logical operation on the data is called a transaction.
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Potassium permanganate is the chemical compound KMnO4. In this salt, manganese is in the +7 oxidation state. The salt is also known as "permanganate of potash." The permanganate ion is a strong oxidizing agent.
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Osmium tetroxide is the chemical compound with the formula OsO4. The compound is noteworthy for its many uses, despite the rarity of osmium. It also has a number of interesting properties, one being that the solid is volatile.
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Sharpless asymmetric dihydroxylation (also called the Sharpless bishydroxylation) is the chemical reaction of an alkene with osmium tetroxide in the presence of a chiral quinine ligand to form a vicinal diol.
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The term chiral (pronounced /ˈkaɪɹ(ə)l̩/) is used to describe an object that is non-superimposable on its mirror image. In terms of chemistry, such objects are usually molecules.
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A reactant or reagent is a substance consumed during a chemical reaction.[1] Solvents and catalysts, although they are involved in the reaction, are usually not referred to as reactants.
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catalysis is the acceleration (increase in rate) of a chemical reaction by means of a substance called a catalyst, which is itself not consumed by the overall reaction.
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The Woodward cis-hydroxylation is the chemical reaction of alkenes with iodine and silver acetate in wet acetic acid to form cis-diols. [1] [2] The reaction is named after its discoverer, Robert Burns Woodward.
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The Prins reaction is an organic reaction consisting of an electrophilic addition of an aldehyde or ketone to an alkene or alkyne followed by capture of a nucleophile [1] [2] [3].
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alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond. The simplest alkenes, with only one double bond and no other functional groups, form a homologous series of hydrocarbons with the general formula
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Formaldehyde (methanal) is the chemical compound with the formula H2CO. The simplest aldehyde, it was first synthesized by the Russian chemist Aleksandr Butlerov but was conclusively identified by August Wilhelm von Hofmann.
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alcohol is any organic compound in which a hydroxyl group (-OH) is bound to a carbon atom of an alkyl or substituted alkyl group. The general formula for a simple acyclic alcohol is CnH2n+1OH.
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