Difference between revisions of "Tetralin"

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(Created page with "{{Chembox | Name = Tetralin | Reference = | IUPACName = 1,2,3,4-tetrahydronaphthalene | PIN = | SystematicName = | OtherNames = Bacticin<br>Benzocyclohexane<br>Naphthalene 1,...")
 
 
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| Name = Tetralin
 
| Name = Tetralin
 
| Reference =  
 
| Reference =  
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| IUPACName = 1,2,3,4-tetrahydronaphthalene
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| IUPACName = 1,2,3,4-Tetrahydronaphthalene
 
| PIN =
 
| PIN =
 
| SystematicName =
 
| SystematicName =
 
| OtherNames = Bacticin<br>Benzocyclohexane<br>Naphthalene 1,2,3,4-tetrahydride<br>THN
 
| OtherNames = Bacticin<br>Benzocyclohexane<br>Naphthalene 1,2,3,4-tetrahydride<br>THN
 
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| ImageFile = Tetralin vial by NurdRage.jpg
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| ImageSize = 300
 
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| ImageCaption = Tetralin used in the production of potassium metal via catalyzed magnesium reduction
 
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| pKb =  
 
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| Solubility = Insoluble
 
| Solubility = Insoluble
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| SolubleOther = Miscible with [[acetone]], [[benzene]], [[butanol]], [[chloroform]], [[decalin]], [[ethanol]], [[petroleum ether]]<br>Soluble in [[aniline]], [[diethyl ether]], [[methanol]] (50% w/w)
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| SolubleOther = Miscible with [[acetone]], [[benzene]], [[butanol]], [[chloroform]], [[decalin]], [[ethanol]], [[isopropanol]], [[petroleum ether]], [[toluene]]<br>Soluble in [[aniline]], [[diethyl ether]], [[methanol]] (50% w/w)
 
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| Section6 = {{Chembox Hazards
 
| Section6 = {{Chembox Hazards
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| AutoignitionPt = 385 °C
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| AutoignitionPt = 385 °C (725 °F; 658 K)
 
| ExploLimits =  
 
| ExploLimits =  
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| ExternalMSDS = [https://www.mathesongas.com/pdfs/msds/MAT23050.pdf MATHESON TRI-GAS]
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| ExternalMSDS = [https://www.docdroid.net/KySbryM/tetralin-sa.pdf Sigma-Aldrich]
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| FlashPt = 77°C
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| FlashPt = 77 °C (170.6 °F; 350 K)
 
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| MainHazards = Irritant
 
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'''Tetralin''' (IUPAC name '''1,2,3,4-tetrahydronaphthalene''') is an organic compound, a hydrocarbon having the chemical formula '''C<sub>10</sub>H<sub>12</sub>'''. It is similar to naphthalene in structure, except one ring is saturated.
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'''Tetralin''' (IUPAC name '''1,2,3,4-tetrahydronaphthalene''') is an organic compound, a hydrocarbon having the chemical formula '''C<sub>10</sub>H<sub>12</sub>'''. It is similar to [[naphthalene]] in structure, except one ring is saturated.
  
 
==Properties==
 
==Properties==
 
===Chemical===
 
===Chemical===
−
The reaction of elemental [[bromine]] with tetralin will give dry hydrogen bromide gas:
+
The reaction of elemental [[bromine]] with tetralin will give dry [[hydrogen bromide]] gas:
  
 
:C<sub>10</sub>H<sub>12</sub> + 4 Br<sub>2</sub> → C<sub>10</sub>H<sub>8</sub>Br<sub>4</sub> + 4 HBr ↑
 
:C<sub>10</sub>H<sub>12</sub> + 4 Br<sub>2</sub> → C<sub>10</sub>H<sub>8</sub>Br<sub>4</sub> + 4 HBr ↑
 +
 +
If [[iodine]] is used, the reaction will give [[hydrogen iodide]].
  
 
===Physical===
 
===Physical===
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Tetralin is a colorless viscous liquid, with a faint naphtalene-like smell.
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Tetralin is a colorless viscous liquid, with a faint naphthalene-like smell. It is insoluble in water, but miscible with many organic solvents, like alcohols.
  
 
==Availability==
 
==Availability==
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There are several ways to prepare Tetralin.
 
There are several ways to prepare Tetralin.
  
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The most convenient route involves the partial hydrogenation of [[naphthalene]] with a platinum catalyst. Small amounts of side products, such as decalin are also produced.
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The most convenient route involves the partial hydrogenation of [[naphthalene]] with a [[platinum]] catalyst. Small amounts of side products, such as decalin are also produced.
  
−
Birch reduction of naphthalene is another route, however the reaction is not selective and is a dangerous method.
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[[Birch reduction]] of naphthalene is another route, however the reaction is not selective. Birch reduction is also a dangerous and time-consuming method.
  
 
==Projects==
 
==Projects==
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*Maky dry [[Hydrogen bromide|HBr]] gas
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*Maky dry [[Hydrogen bromide|HBr]] and [[Hydrogen iodide|HI]] gas
 
*Preparation of elemental [[potassium]]
 
*Preparation of elemental [[potassium]]
  
 
==Handling==
 
==Handling==
 
===Safety===
 
===Safety===
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Tetralin is irritant and should be handled with care.
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Tetralin is irritant and should be handled with care. With a flash point of 77 °C, it is not very flammable and unless heated prior, it doesn't pose a fire hazard.
  
 
===Storage===
 
===Storage===
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In closed bottles.
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In closed air-tight bottles. Since it may form peroxides in contact with air, it's best to test it for peroxides every few months.
  
 
===Disposal===
 
===Disposal===
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[[Category:Nonpolar solvents]]
 
[[Category:Nonpolar solvents]]
 
[[Category:Liquids]]
 
[[Category:Liquids]]
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[[Category:Peroxide forming chemicals]]
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[[Category:Air-sensitive materials]]

Latest revision as of 18:24, 31 August 2020

Tetralin
Tetralin vial by NurdRage.jpg
Tetralin used in the production of potassium metal via catalyzed magnesium reduction
Names
IUPAC name
1,2,3,4-Tetrahydronaphthalene
Other names
Bacticin
Benzocyclohexane
Naphthalene 1,2,3,4-tetrahydride
THN
Identifiers
Jmol-3D images Image
Properties
C10H12
Molar mass 132.21 g/mol
Appearance Colorless liquid
Odor Naphtalene-like
Density 0.970 g/cm3 (at 20 °C)
Melting point −35.8 °C (−32.4 °F; 237.3 K)
Boiling point 207.6 °C (405.7 °F; 480.8 K)
Insoluble
Solubility Miscible with acetone, benzene, butanol, chloroform, decalin, ethanol, isopropanol, petroleum ether, toluene
Soluble in aniline, diethyl ether, methanol (50% w/w)
Hazards
Safety data sheet Sigma-Aldrich
Flash point 77 °C (170.6 °F; 350 K)
Related compounds
Related compounds
 Naphthalene
Decalin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tetralin (IUPAC name 1,2,3,4-tetrahydronaphthalene) is an organic compound, a hydrocarbon having the chemical formula C10H12. It is similar to naphthalene in structure, except one ring is saturated.

Properties

Chemical

The reaction of elemental bromine with tetralin will give dry hydrogen bromide gas:

C10H12 + 4 Br2 → C10H8Br4 + 4 HBr ↑

If iodine is used, the reaction will give hydrogen iodide.

Physical

Tetralin is a colorless viscous liquid, with a faint naphthalene-like smell. It is insoluble in water, but miscible with many organic solvents, like alcohols.

Availability

Tetralin can be purchased from chemical suppliers.

Preparation

There are several ways to prepare Tetralin.

The most convenient route involves the partial hydrogenation of naphthalene with a platinum catalyst. Small amounts of side products, such as decalin are also produced.

Birch reduction of naphthalene is another route, however the reaction is not selective. Birch reduction is also a dangerous and time-consuming method.

Projects

Handling

Safety

Tetralin is irritant and should be handled with care. With a flash point of 77 °C, it is not very flammable and unless heated prior, it doesn't pose a fire hazard.

Storage

In closed air-tight bottles. Since it may form peroxides in contact with air, it's best to test it for peroxides every few months.

Disposal

Should be mixed with a more flammable solvent and burned.

References

Relevant Sciencemadness threads

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