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{{chembox {{chembox
| Watchedfields = changed |Watchedfields = changed
| verifiedrevid = 470604697 |verifiedrevid = 470604697
| Name = Tetralin |Name = Tetralin
| ImageFile_Ref = {{chemboximage|correct|??}} |ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Tetralin.svg |ImageFile = Tetralin.svg
| ImageSize = 160px |ImageSize = 160px
| ImageAlt = Skeletal formula |ImageAlt = Skeletal formula
| ImageFile1 = Tetralin-3D-balls.png |ImageFile1 = Tetralin-3D-balls.png
| ImageSize1 = 170px |ImageSize1 = 170px
| ImageAlt1 = Ball-and-stick model |ImageAlt1 = Ball-and-stick model
| PIN = 1,2,3,4-Tetrahydronaphthalene |PIN = 1,2,3,4-Tetrahydronaphthalene
| OtherNames = 1,2,3,4-Tetrahydronaphthalene, Benzocyclohexane, NSC 77451, Tetrahydronaphthalene, Tetranap |OtherNames = 1,2,3,4-Tetrahydronaphthalene, Benzocyclohexane, NSC 77451, Tetrahydronaphthalene, Tetranap
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}} |ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 35008 |ChEBI = 35008
| SMILES = c1ccc2c(c1)CCCC2 |SMILES = c1ccc2c(c1)CCCC2
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8097 |ChemSpiderID = 8097
| PubChem = 8404 |PubChem = 8404
| UNII_Ref = {{fdacite|correct|FDA}} |UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FT6XMI58YQ |UNII = FT6XMI58YQ
| KEGG_Ref = {{keggcite|correct|kegg}} |KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14114 |KEGG = C14114
| InChI = 1/C10H12/c1-2-6-10-8-4-3-7-9(10)5-1/h1-2,5-6H,3-4,7-8H2 |InChI = 1/C10H12/c1-2-6-10-8-4-3-7-9(10)5-1/h1-2,5-6H,3-4,7-8H2
| InChIKey = CXWXQJXEFPUFDZ-UHFFFAOYAG |InChIKey = CXWXQJXEFPUFDZ-UHFFFAOYAG
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H12/c1-2-6-10-8-4-3-7-9(10)5-1/h1-2,5-6H,3-4,7-8H2 |StdInChI = 1S/C10H12/c1-2-6-10-8-4-3-7-9(10)5-1/h1-2,5-6H,3-4,7-8H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CXWXQJXEFPUFDZ-UHFFFAOYSA-N |StdInChIKey = CXWXQJXEFPUFDZ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}} |CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 119-64-2 |CASNo = 119-64-2
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| C=10 |H=12 |C=10 |H=12
| Appearance = colorless liquid with an odor similar to naphthalene |Appearance = colorless liquid with an odor similar to naphthalene
| Density = 0.970 g/cm<sup>3</sup> |Density = 0.970 g/cm<sup>3</sup>
| Solubility = Insoluble |Solubility = Insoluble
| MeltingPtC = -35.8 |MeltingPtC = -35.8
| BoilingPtC = 206 to 208 |BoilingPtC = 206 to 208
| Viscosity = 2.02 ] at 25&nbsp;°C<ref>{{cite journal|doi=10.1007/BF00514480|title=Density and viscosity of tetralin and trans-decalin|year=1989|last1=Gonçalves|first1=F. A.|last2=Hamano|first2=K.|last3=Sengers|first3=J. V.|journal=International Journal of Thermophysics|volume=10|issue=4|pages=845|bibcode=1989IJT....10..845G|s2cid=119843498}}</ref> |Viscosity = 2.02 ] at 25&nbsp;°C<ref>{{cite journal|doi=10.1007/BF00514480|title=Density and viscosity of tetralin and trans-decalin|year=1989|last1=Gonçalves|first1=F. A.|last2=Hamano|first2=K.|last3=Sengers|first3=J. V.|journal=International Journal of Thermophysics|volume=10|issue=4|pages=845|bibcode=1989IJT....10..845G|s2cid=119843498}}</ref>
}} }}
|Section7={{Chembox Hazards |Section3={{Chembox Hazards
| ExternalSDS = |ExternalSDS =
| FlashPtC = 77 |FlashPtC = 77
| AutoignitionPtC = 385 |AutoignitionPtC = 385
}} }}
}} }}


'''Tetralin''' ('''1,2,3,4-tetrahydronaphthalene''') is a ] having the ] C<sub>10</sub>H<sub>12</sub>. It is a partially ] derivative of ]. It is a colorless liquid that is used as a ].<ref name=Ullmann/> '''Tetralin''' ('''1,2,3,4-tetrahydronaphthalene''') is a ] having the ] C<sub>10</sub>H<sub>12</sub>. It is a partially ] derivative of ]. It is a colorless liquid that is used as a ].<ref name=Ullmann/>


==Production== ==Production==
Line 55: Line 55:
] ]


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-4-pentene 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-4-pentene using ] ],<ref>{{cite book |author= Michael B. Smith |title= Organic Synthesis |publisher= Academic Press |year= 2011 |pages= 1209–1210 |edition= third |isbn= 9780124158849 }}</ref>
Line 65: Line 65:
|author=Isa, Khairuddin Md.; Abdullah, Tuan Amran Tuan; Md. Ali, Umi Fazara|journal=Renewable & Sustainable Energy Reviews|year=2018|volume=81(Part_1)|page=1259-1268|doi=10.1016/j.rser.2017.04.006}}</ref><ref name=Ullmann/> |author=Isa, Khairuddin Md.; Abdullah, Tuan Amran Tuan; Md. Ali, Umi Fazara|journal=Renewable & Sustainable Energy Reviews|year=2018|volume=81(Part_1)|page=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}}


It is also used for the laboratory synthesis of ]: It is also used for the laboratory synthesis of ]:
: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
The facility of this reaction is in part a consequence of the moderated strength of the ]ic C-H bonds. The facility of this reaction is in part a consequence of the moderated strength of the ]ic C-H bonds.


==Safety== ==Safety==
{{LD50}} (rats, oral) is 2.68 g/kg. Tetralin induces ].<ref name=Ullmann/> {{LD50}} (rats, oral) is 2.68 g/kg. Tetralin induces ].<ref name=Ullmann/>


==References== ==References==

Revision as of 16:31, 22 April 2023

Tetralin
Skeletal formula
Ball-and-stick model
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 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H12/c1-2-6-10-8-4-3-7-9(10)5-1/h1-2,5-6H,3-4,7-8H2Key: CXWXQJXEFPUFDZ-UHFFFAOYSA-N
  • InChI=1/C10H12/c1-2-6-10-8-4-3-7-9(10)5-1/h1-2,5-6H,3-4,7-8H2Key: CXWXQJXEFPUFDZ-UHFFFAOYAG
SMILES
  • c1ccc2c(c1)CCCC2
Properties
Chemical formula C10H12
Molar mass 132.206 g·mol
Appearance colorless liquid with an odor similar to naphthalene
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). checkY verify (what is  ?) Infobox references
Chemical compound

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-4-pentene using concentrated sulfuric acid,

Darzens synthesis of tetralin derivatives

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

  1. 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.
  2. ^ 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.
  3. 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.
  4. Michael B. Smith (2011). Organic Synthesis (third ed.). Academic Press. pp. 1209–1210. ISBN 9780124158849.
  5. 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)
  6. 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.
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