Difference between revisions of "Benzoquinone"
(clean-up, expansion, cats, etc.) |
|||
| Line 5: | Line 5: | ||
| PIN = | | PIN = | ||
| SystematicName = | | SystematicName = | ||
| − | | OtherNames = Benzoquinone <br> para- | + | | OtherNames = Benzoquinone <br> para-Benzoquinone <br> Bara-quinone |
<!-- Images --> | <!-- Images --> | ||
| ImageFile = Benzoquinone Crystals.jpg | | ImageFile = Benzoquinone Crystals.jpg | ||
| Line 51: | Line 51: | ||
| BoilingPtC = | | BoilingPtC = | ||
| BoilingPt_ref = | | BoilingPt_ref = | ||
| − | | BoilingPt_notes = | + | | BoilingPt_notes = Sublimes |
| − | | Density = 1.318 g/cm | + | | Density = 1.318 g/cm<sup>3</sup> (at 20 °C) |
| − | | Formula = | + | | Formula = C<sub>6</sub>H<sub>4</sub>O<sub>2</sub> |
| HenryConstant = | | HenryConstant = | ||
| LogP = | | LogP = | ||
| − | | MolarMass = | + | | MolarMass = 108.10 g/mol |
| MeltingPt = | | MeltingPt = | ||
| − | | MeltingPtC = | + | | MeltingPtC = 115 |
| MeltingPt_ref = | | MeltingPt_ref = | ||
| MeltingPt_notes = | | MeltingPt_notes = | ||
| + | | Odor = Acrid, chlorine-like | ||
| pKa = | | pKa = | ||
| pKb = | | pKb = | ||
| − | | Solubility = | + | | Solubility = 1.1 g/100 ml (18 °C) |
| − | | SolubleOther = | + | | SolubleOther = Soluble in [[acetone]]<br>Slightly soluble in [[benzene]], [[diethyl ether]], [[ethanol]], [[petroleum ether]] |
| Solvent = | | Solvent = | ||
| − | | VaporPressure = 0.1 mmHg at | + | | VaporPressure = 0.1 mmHg at 25 °C |
}} | }} | ||
| Section3 = {{Chembox Structure | | Section3 = {{Chembox Structure | ||
| Line 89: | Line 90: | ||
| AutoignitionPt = | | AutoignitionPt = | ||
| ExploLimits = | | ExploLimits = | ||
| − | | ExternalMSDS = | + | | ExternalMSDS = [https://www.docdroid.net/ALXw0mn/p-benzoquinone-sa.pdf Sigma-Aldrich] |
| FlashPt = | | FlashPt = | ||
| − | | LD50 = | + | | LD50 = 130 mg/kg (rat, oral)<br>25 mg/kg (mouse, oral) |
| LC50 = | | LC50 = | ||
| MainHazards = Toxic | | MainHazards = Toxic | ||
| Line 104: | Line 105: | ||
| OtherFunction = | | OtherFunction = | ||
| OtherFunction_label = | | OtherFunction_label = | ||
| − | | OtherCompounds = [[ | + | | OtherCompounds = [[Hydroquinone]] |
}} | }} | ||
}} | }} | ||
| + | '''1,4-Benzoquinone''', commonly known as '''para-quinone''', is a chemical compound with the formula '''C<sub>6</sub>H<sub>4</sub>O<sub>2</sub>'''. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor. This six-membered ring compound is the oxidized derivative of [[hydroquinone]]. The molecule is multifunctional: it exhibits properties of a ketone, forming an oxime; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound. | ||
| − | + | It is an isomer of 1,2-benzoquinone. | |
| − | + | ||
==Properties== | ==Properties== | ||
===Chemical=== | ===Chemical=== | ||
| − | + | An acidic [[potassium iodide]] solution reduces a solution of benzoquinone to [[hydroquinone]], which can be reoxidized back to the quinone with a solution of [[silver nitrate]]. | |
===Physical=== | ===Physical=== | ||
| Line 121: | Line 122: | ||
==Availability== | ==Availability== | ||
| − | + | 1,4-Benzoquinone is sold by chemical suppliers. | |
==Preparation== | ==Preparation== | ||
| Line 127: | Line 128: | ||
==Projects== | ==Projects== | ||
| − | + | *Make hydroquinone | |
| + | *Make hydroxyquinol triacetate | ||
==Handling== | ==Handling== | ||
| − | |||
===Safety=== | ===Safety=== | ||
Benzoquinone vapours are very irritating to the eyes and to the respiratory system. Handle in a well ventilated area, ideally in a fume cupboard. | Benzoquinone vapours are very irritating to the eyes and to the respiratory system. Handle in a well ventilated area, ideally in a fume cupboard. | ||
| Line 137: | Line 138: | ||
Benzoquinone is probably carcinogenic. | Benzoquinone is probably carcinogenic. | ||
| − | |||
===Storage=== | ===Storage=== | ||
| Line 143: | Line 143: | ||
===Disposal=== | ===Disposal=== | ||
| − | + | Can be destroyed by oxidizing it with an oxidizing mixture, though due to its strong odor, this must be done outside or in a fumehood. | |
==References== | ==References== | ||
<references/> | <references/> | ||
===Relevant Sciencemadness threads=== | ===Relevant Sciencemadness threads=== | ||
| + | *[http://www.sciencemadness.org/talk/viewthread.php?tid=14232 p-benzoquinone HELP!!!] | ||
| + | *[http://www.sciencemadness.org/talk/viewthread.php?tid=8250 Benzoquinone from Paracetamol] | ||
| + | |||
| + | [[Category:Chemical compounds]] | ||
| + | [[Category:Organic compounds]] | ||
| + | [[Category:Aromatic compounds]] | ||
| + | [[Category:Quinones]] | ||
| + | [[Category:Solids]] | ||
| + | [[Category:Irritants]] | ||
Revision as of 19:50, 4 April 2018
| |
| Names | |
|---|---|
| IUPAC name
Cyclohexa-2,5-diene-1,4-dione
| |
| Other names
Benzoquinone
para-Benzoquinone Bara-quinone | |
| Properties | |
| C6H4O2 | |
| Molar mass | 108.10 g/mol |
| Appearance | Yellow solid |
| Odor | Acrid, chlorine-like |
| Density | 1.318 g/cm3 (at 20 °C) |
| Melting point | 115 °C (239 °F; 388 K) |
| Boiling point | Sublimes |
| 1.1 g/100 ml (18 °C) | |
| Solubility | Soluble in acetone Slightly soluble in benzene, diethyl ether, ethanol, petroleum ether |
| Vapor pressure | 0.1 mmHg at 25 °C |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
130 mg/kg (rat, oral) 25 mg/kg (mouse, oral) |
| Related compounds | |
| Related compounds
|
Hydroquinone |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor. This six-membered ring compound is the oxidized derivative of hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, forming an oxime; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.
It is an isomer of 1,2-benzoquinone.
Contents
Properties
Chemical
An acidic potassium iodide solution reduces a solution of benzoquinone to hydroquinone, which can be reoxidized back to the quinone with a solution of silver nitrate.
Physical
Benzoquinone readily undergoes sublimation, even at room temperature.
Benzoquinone forms bright yellow needle-like crystals.
Availability
1,4-Benzoquinone is sold by chemical suppliers.
Preparation
Benzoquinone can be prepared by oxidation of hydroquinone.
Projects
- Make hydroquinone
- Make hydroxyquinol triacetate
Handling
Safety
Benzoquinone vapours are very irritating to the eyes and to the respiratory system. Handle in a well ventilated area, ideally in a fume cupboard.
Skin contact can result in brown staining, and apparently even localised tissue necrosis in severe cases. Benzoquinone is potentially a skin sensitiser.
Benzoquinone is probably carcinogenic.
Storage
In tightly-closed glass bottles. Stains/degrades polyethylene containers.
Disposal
Can be destroyed by oxidizing it with an oxidizing mixture, though due to its strong odor, this must be done outside or in a fumehood.
