Tetralin is produced by the catalytic hydrogenation of naphthalene.[2]
Although nickel catalysts are traditionally employed, many variations have been evaluated.[3] Over-hydrogenation converts tetralin into decahydronaphthalene (decalin). Rarely encountered is dihydronaphthalene (dialin).
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.[5][2]
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fast reactors as a secondary coolant to keep sodium seals around pump impellers solidified; however its use has been superseded by NaK.[6]: 24:30
It is also used for the laboratory synthesis of hydrogen bromide:
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. S2CID 119843498.
^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: 18–22. doi:10.1007/BF00727949. S2CID 95026822.
^Michael B. Smith (2011). Organic Synthesis (third ed.). Academic Press. pp. 1209–1210. ISBN9780124158849.
^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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^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.
January 10, 2024
tetralin, tetrahydronaphthalene, hydrocarbon, having, chemical, formula, c10h12, partially, hydrogenated, derivative, naphthalene, colorless, liquid, that, used, hydrogen, donor, solvent, namespreferred, iupac, name, tetrahydronaphthaleneother, names, tetrahyd. 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 2 Tetralin NamesPreferred IUPAC name 1 2 3 4 TetrahydronaphthaleneOther names 1 2 3 4 Tetrahydronaphthalene Benzocyclohexane NSC 77451 Tetrahydronaphthalene TetranapIdentifiersCAS Number 119 64 2 Y3D model JSmol Interactive imageChEBI CHEBI 35008 YChemSpider 8097 YECHA InfoCard 100 003 946KEGG C14114 YPubChem CID 8404UNII FT6XMI58YQ YCompTox Dashboard EPA DTXSID1026118InChI InChI 1S C10H12 c1 2 6 10 8 4 3 7 9 10 5 1 h1 2 5 6H 3 4 7 8H2 YKey CXWXQJXEFPUFDZ UHFFFAOYSA N YInChI 1 C10H12 c1 2 6 10 8 4 3 7 9 10 5 1 h1 2 5 6H 3 4 7 8H2Key CXWXQJXEFPUFDZ UHFFFAOYAGSMILES c1ccc2c c1 CCCC2PropertiesChemical formula C 10H 12Molar mass 132 206 g mol 1Appearance colorless liquidDensity 0 970 g cm3Melting point 35 8 C 32 4 F 237 3 K Boiling point 206 to 208 C 403 to 406 F 479 to 481 K Solubility in water InsolubleViscosity 2 02 cP at 25 C 1 HazardsFlash point 77 C 171 F 350 K Autoignitiontemperature 385 C 725 F 658 K Safety data sheet SDS JT Baker MSDSExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Production 1 1 Laboratory methods 2 Uses 3 Safety 4 ReferencesProduction editTetralin is produced by the catalytic hydrogenation of naphthalene 2 nbsp Although nickel catalysts are traditionally employed many variations have been evaluated 3 Over hydrogenation converts tetralin into decahydronaphthalene decalin Rarely encountered is dihydronaphthalene dialin Laboratory methods edit 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 pent 4 ene using concentrated sulfuric acid 4 nbsp Darzens synthesis of tetralin derivativesUses editTetralin 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 5 2 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 6 24 30 It is also used for the laboratory synthesis of hydrogen bromide C10H12 4 Br2 C10H8Br4 4 HBrThe facility of this reaction is in part a consequence of the moderated strength of the benzylic C H bonds Safety editLD50 rats oral is 2 68 g kg Tetralin induces methemoglobinemia 2 References edit Goncalves 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 S2CID 119843498 a b c d Collin Gerd Hoke Hartmut Greim Helmut 2003 Naphthalene and Hydronaphthalenes Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a17 001 pub2 ISBN 978 3527306732 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 22 doi 10 1007 BF00727949 S2CID 95026822 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 amp Sustainable Energy Reviews 81 Part 1 1259 1268 doi 10 1016 j rser 2017 04 006 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link 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 Retrieved from https en wikipedia org w index php title Tetralin amp oldid 1153158044, wikipedia, wiki, book, books, library,
