Difference between revisions of "Benzoquinone"

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(clean-up, expansion, cats, etc.)
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| PIN =
 
| PIN =
 
| SystematicName =
 
| SystematicName =
| OtherNames = Benzoquinone <br> para-benzoquinone <br> para-quinone
+
| OtherNames = Benzoquinone <br> para-Benzoquinone <br> Bara-quinone
 
<!-- Images -->
 
<!-- Images -->
 
| ImageFile = Benzoquinone Crystals.jpg
 
| ImageFile = Benzoquinone Crystals.jpg
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| BoilingPtC =  
 
| BoilingPtC =  
 
| BoilingPt_ref =  
 
| BoilingPt_ref =  
| BoilingPt_notes =  
+
| BoilingPt_notes = Sublimes
| Density = 1.318 g/cm^3 at 20C
+
| 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 =  
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| SolubleOther = Soluble in [[acetone]]<br>Slightly soluble in [[benzene]], [[diethyl ether]], [[ethanol]], [[petroleum ether]]
 
| Solvent =  
 
| Solvent =  
| VaporPressure = 0.1 mmHg at 25C
+
| VaporPressure = 0.1 mmHg at 25 °C
 
   }}
 
   }}
 
| Section3 = {{Chembox Structure
 
| Section3 = {{Chembox Structure
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| 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
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| OtherFunction =  
 
| OtherFunction =  
 
| OtherFunction_label =  
 
| OtherFunction_label =  
| OtherCompounds = [[hydroquinone]]
+
| 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.
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.
+
  
 
==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===
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==Availability==
 
==Availability==
Delete this section if not applicable
+
1,4-Benzoquinone is sold by chemical suppliers.
  
 
==Preparation==
 
==Preparation==
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==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.
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Benzoquinone is probably carcinogenic.
 
Benzoquinone is probably carcinogenic.
 
  
 
===Storage===
 
===Storage===
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===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

1,4-Benzoquinone
Benzoquinone Crystals.jpg
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):
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.

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.

References

Relevant Sciencemadness threads