1,2,3,4-Tetrahydronaphthalene, Benzocyclohexane, NSC 77451, Tetrahydronaphthalene, Tetranap
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||132.206 g·mol−1|
|Appearance||colorless liquid with an odor similar to naphthalene|
|Melting point||−35.8 °C (−32.4 °F; 237.3 K)|
|Boiling point||206 to 208 °C (403 to 406 °F; 479 to 481 K)|
|Viscosity||2.02 cP at 25 °C|
|Safety data sheet||JT Baker MSDS|
|Flash point||77 °C (171 °F; 350 K)|
|385 °C (725 °F; 658 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Tetralin (1,2,3,4-tetrahydronaphthalene) is a hydrocarbon having the chemical formula C10H12. It is a partially hydrogenated derivative of naphthalene. It is a colorless liquid that is used as a hydrogen-donor solvent.
Tetralin is produced by the catalytic hydrogenation of naphthalene.
Although nickel catalysts are traditionally employed, many variations have been evaluated. Over hydrogenation converts tetralin into octahydronaphthalene (decalin). Rarely encountered is dihydronaphthalene (dialin).
In a classic named reaction called the Darzens tetralin synthesis, named for Auguste Georges Darzens (1926), derivatives can be prepared by intramolecular electrophilic aromatic substitution reaction of a 1-aryl-4-pentene using concentrated sulfuric acid,
Tetralin is used as a hydrogen-donor solvent, 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.
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 benzylic C-H bonds.
- Gonçalves, F. A.; Hamano, K.; Sengers, J. V. (1989). "Density and viscosity of tetralin and trans-decalin". International Journal of Thermophysics. 10 (4): 845. Bibcode:1989IJT....10..845G. doi:10.1007/BF00514480.
- Collin, Gerd; Höke, Hartmut; Greim, Helmut (2003), "Naphthalene and Hydronaphthalenes", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a17_001.pub2
- Krichko, A. A.; Skvortsov, D. V.; Titova, T. A.; Filippov, B. S.; Dogadkina, N. E. (1969). "Production of tetralin by the hydrogenation of naphthalene-containing fractions". Chemistry and Technology of Fuels and Oils. 5: 18. doi:10.1007/BF00727949.
- Michael B. Smith (2011). Organic Synthesis (third ed.). Academic Press. pp. 1209–1210. ISBN 9780124158849.
- Isa, Khairuddin Md.; Abdullah, Tuan Amran Tuan; Md. Ali, Umi Fazara (2018). "Hydrogen donor solvents in liquefaction of biomass: A review". Renewable & Sustainable Energy Reviews. 81(Part_1): 1259-1268. doi:10.1016/j.rser.2017.04.006.CS1 maint: Multiple names: authors list (link)