Tetralin (1,2,3,4-tetrahydronaphthalene) is a

hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak ...

having the

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

C₁₀H₁₂. It is a partially hydrogenated derivative of

naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromati ...

. It is a colorless liquid that is used as a

hydrogen-donor solvent A hydrogen-donor solvent is hydrocarbon that transfers hydrogen to hydrogen-poor substrates, such as coal. The hydrogen-poor substrates could be a solute or suspension. The classic hydrogen-donor solvent (or just donor solvent) is tetrahydronapht ...

Production

Tetralin is produced by the catalytic hydrogenation of naphthalene. Tetralin synthesis 01

Although nickel catalysts are traditionally employed, many variations have been evaluated. Over-hydrogenation converts tetralin into decahydronaphthalene (

decalin Decalin (decahydronaphthalene, also known as bicyclo .4.0ecane and sometimes decaline), a bicyclic organic compound, is an industrial solvent. A colorless liquid with an aromatic odor, it is used as a solvent for many resins or fuel additives. ...

). Rarely encountered is dihydronaphthalene (

dialin Dialin (1,2-dihydronaphthalene) is a hydrocarbon with the chemical formula C10H10. It is similar to naphthalene but one ring is partially saturated. See also * Naphthalene * Tetralin * Decalin Decalin (decahydronaphthalene, also known as bi ...

Laboratory methods

In a classic named reaction called the Darzens tetralin synthesis, named for Auguste Georges Darzens (1926),

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...

s can be prepared by intramolecular

electrophilic aromatic substitution Electrophilic aromatic substitution is an organic reaction in which an atom that is attached to an aromatic system (usually hydrogen) is replaced by an electrophile. Some of the most important electrophilic aromatic substitutions are aromatic n ...

reaction of a 1-aryl-4-pentene using concentrated

sulfuric acid Sulfuric acid ( American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular fo ...

Uses

Tetralin is used as a

, for example in coal liquifaction. It functions as a source of H₂, which is transferred to the coal. The partially hydrogenated coal is more soluble. It has been used in sodium-cooled fast reactors as a secondary coolant to keep sodium seals around pump impellers solidified; however its use has been superseded by

NaK In data networking, telecommunications, and computer buses, an acknowledgment (ACK) is a signal that is passed between communicating processes, computers, or devices to signify acknowledgment, or receipt of message, as part of a communications ...

.US Atomic Energy Commission (1961) SRE Core Recovery
Remediation method after a failure in the moderator cans due to a crack in the secondary coolant tubes in the SRE, Spring 1959. This caused a leak of Tetralin into the reactor. It is also used for the laboratory synthesis of HBr: :C₁₀H₁₂ + 4 Br₂ → C₁₀H₈Br₄ + 4 HBr The facility of this reaction is in part a consequence of the moderated strength of the

benzyl In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure . Benzyl features a benzene ring () attached to a methylene group () group. Nomenclature In IUPAC nomenclature, the prefix benzyl refers to a subs ...

ic C-H bonds.

Safety

(rats, oral) is 2.68 g/kg. Tetralin induces

methemoglobinemia Methemoglobinemia, or methaemoglobinaemia, is a condition of elevated methemoglobin in the blood. Symptoms may include headache, dizziness, shortness of breath, nausea, poor muscle coordination, and blue-colored skin (cyanosis). Complications m ...

References

{{Authority control Aromatic solvents Aromatic hydrocarbons