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| Although nickel catalysts are traditionally employed, many variations have been evaluated.<ref>{{cite journal|doi=10.1007/BF00727949|title=Production of tetralin by the hydrogenation of naphthalene-containing fractions|year=1969|last1=Krichko|first1=A. A.|last2=Skvortsov|first2=D. V.|last3=Titova|first3=T. A.|last4=Filippov|first4=B. S.|last5=Dogadkina|first5=N. E.|journal=Chemistry and Technology of Fuels and Oils|volume=5|pages=18–22|s2cid=95026822}}</ref> Over-hydrogenation converts tetralin into decahydronaphthalene (]). Rarely encountered is dihydronaphthalene (]). | Although nickel catalysts are traditionally employed, many variations have been evaluated.<ref>{{cite journal|doi=10.1007/BF00727949|title=Production of tetralin by the hydrogenation of naphthalene-containing fractions|year=1969|last1=Krichko|first1=A. A.|last2=Skvortsov|first2=D. V.|last3=Titova|first3=T. A.|last4=Filippov|first4=B. S.|last5=Dogadkina|first5=N. E.|journal=Chemistry and Technology of Fuels and Oils|volume=5|pages=18–22|s2cid=95026822}}</ref> Over-hydrogenation converts tetralin into decahydronaphthalene (]). Rarely encountered is dihydronaphthalene (]). | ||
| ===Laboratory methods=== | ===Laboratory methods=== | ||
| In a classic ] called the '''Darzens tetralin synthesis''', named for ] (1926), ]s can be prepared by ] ] reaction of a 1-aryl-pent-4-ene using ] ],<ref>{{cite book |author= Michael B. Smith |title= Organic Synthesis |publisher= Academic Press |year= 2011 |pages= 1209–1210 |edition= third |isbn= 9780124158849}}</ref> | In a classic ] called the '''Darzens tetralin synthesis''', named for ] (1926), ]s can be prepared by ] ] reaction of a 1-aryl-pent-4-ene using ] ],<ref>{{cite book |author= Michael B. Smith |title= Organic Synthesis |publisher= Academic Press |year= 2011 |pages= 1209–1210 |edition= third |isbn= 9780124158849}}</ref> | ||
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| ==Uses== | ==Uses== | ||
| Tetralin is used as a ], for example in ]. It functions as a source of H<sub>2</sub>, which is transferred to the coal. The partially hydrogenated coal is more soluble.<ref>{{cite journal|title=Hydrogen donor solvents in liquefaction of biomass: A review | Tetralin is used as a ], for example in ]. It functions as a source of H<sub>2</sub>, which is transferred to the coal. The partially hydrogenated coal is more soluble.<ref>{{cite journal|title=Hydrogen donor solvents in liquefaction of biomass: A review | ||
| |author=Isa, Khairuddin Md.; Abdullah, Tuan Amran Tuan; Md. Ali, Umi Fazara|journal=Renewable & Sustainable Energy Reviews|year=2018|volume=81(Part_1)| |
|author=Isa, Khairuddin Md.; Abdullah, Tuan Amran Tuan; Md. Ali, Umi Fazara|journal=Renewable & Sustainable Energy Reviews|year=2018|volume=81(Part_1)|pages=1259–1268|doi=10.1016/j.rser.2017.04.006}}</ref><ref name=Ullmann/> | ||
| It has been used in ]s as a secondary coolant to keep sodium seals around pump impellers solidified; however its use has been superseded by ].<ref name=nak> Remediation method after a failure in the moderator cans due to a crack in the secondary coolant tubes in the ], Spring 1959. This caused a leak of Tetralin into the reactor.</ref>{{rp|24:30}} | It has been used in ]s as a secondary coolant to keep sodium seals around pump impellers solidified; however its use has been superseded by ].<ref name=nak> Remediation method after a failure in the moderator cans due to a crack in the secondary coolant tubes in the ], Spring 1959. This caused a leak of Tetralin into the reactor.</ref>{{rp|24:30}} | ||
Revision as of 23:30, 26 March 2024
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| Names | |
|---|---|
| Preferred IUPAC name 1,2,3,4-Tetrahydronaphthalene | |
| Other names 1,2,3,4-Tetrahydronaphthalene, Benzocyclohexane, NSC 77451, Tetrahydronaphthalene, Tetranap | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.003.946 
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| KEGG | |
| PubChem CID | |
| UNII | |
| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
| Chemical formula | C10H12 |
| Molar mass | 132.206 g·mol |
| Appearance | colorless liquid |
| Density | 0.970 g/cm |
| 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) |
| Solubility in water | Insoluble |
| Viscosity | 2.02 cP at 25 °C |
| Hazards | |
| Flash point | 77 °C (171 °F; 350 K) |
| Autoignition temperature |
385 °C (725 °F; 658 K) |
| Safety data sheet (SDS) | JT Baker MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
| |
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.
Production
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 decahydronaphthalene (decalin). Rarely encountered is dihydronaphthalene (dialin).
Laboratory methods
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,
Uses
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; however its use has been superseded by NaK.
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.
Safety
LD50 (rats, oral) is 2.68 g/kg. Tetralin induces methemoglobinemia.
References
- 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.
- ^ 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. 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 & 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.