| Revision as of 12:43, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 466516259 of page Tetralin for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 01:58, 2 December 2024 edit Citation bot (talk | contribs)Bots5,408,194 edits Add: bibcode, issue. | Use this bot. Report bugs. | Suggested by Abductive | Category:Tetralins | #UCB_Category 23/26 |
| Line 1: |
Line 1: |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{chembox |
|
{{chembox |
|
|
|Watchedfields = changed |
|
| verifiedrevid = 444220230 |
|
|verifiedrevid = 470604697 |
|
| Name = Tetralin |
|
|Name = Tetralin |
|
| ImageFile_Ref = {{chemboximage|correct|??}} |
|
|ImageFile_Ref = {{chemboximage|correct|??}} |
|
| ImageFile = Tetralin.svg |
|
|ImageFile = Tetralin.svg |
|
| ImageSize = 160px |
|
|
| ImageAlt = Skeletal formula |
|
|ImageSize = 160px |
|
|
|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 |
|
| IUPACName = 1,2,3,4-tetrahydronaphthalene |
|
|PIN = 1,2,3,4-Tetrahydronaphthalene |
|
| OtherNames = naphthalene 1,2,3,4-tetrahydride<br />Bacticin<br />benzocyclohexane<br />THN |
|
|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 |
|
| ⚫ |
| C=10|H=12 |
|
| ⚫ |
| Appearance = Clear, colorless liquid |
|
| ⚫ |
| Density = 0.970 g/cm³ |
|
| ⚫ |
| Solubility = Insoluble |
|
| ⚫ |
| MeltingPtC = -35.8 |
|
|
| BoilingPtCL = 206 |
|
|
| BoilingPtCH = 208 |
|
| ⚫ |
}} |
|
| ⚫ |
| Section7 = {{Chembox Hazards |
|
| ⚫ |
| ExternalMSDS = |
|
|
| FlashPt = 77 °C |
|
|
| Autoignition = 385 °C |
|
| ⚫ |
}} |
|
|
}} |
|
}} |
|
⚫ |
|Section2={{Chembox Properties |
|
⚫ |
|C=10 |H=12 |
|
⚫ |
|Appearance = colorless liquid |
|
⚫ |
|Density = 0.970 g/cm<sup>3</sup> |
|
⚫ |
|Solubility = Insoluble |
|
⚫ |
|MeltingPtC = -35.8 |
|
|
|BoilingPtC = 206 to 208 |
|
|
|Viscosity = 2.02 ] at 25 °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> |
|
⚫ |
}} |
|
⚫ |
|Section3={{Chembox Hazards |
|
⚫ |
|ExternalSDS = |
|
|
|FlashPtC = 77 |
|
|
|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/> |
|
|
|
|
|
==Production== |
|
|
Tetralin is produced by the catalytic hydrogenation of naphthalene.<ref name=Ullmann>{{Ullmann|first=Gerd|last=Collin|first2=Hartmut|last2=Höke|first3=Helmut|last3=Greim|title=Naphthalene and Hydronaphthalenes|year=2003|doi=10.1002/14356007.a17_001.pub2}}</ref> |
|
|
|
|
|
] |
|
|
|
|
|
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|issue=1 |pages=18–22|bibcode=1969CTFO....5...18K |s2cid=95026822}}</ref> Over-hydrogenation converts tetralin into decahydronaphthalene (]). Rarely encountered is dihydronaphthalene (]). |
|
|
|
|
|
===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> |
|
|
|
|
|
] |
|
|
|
|
|
==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 |
|
|
|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|bibcode=2018RSERv..81.1259I }}</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 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 |
|
|
The facility of this reaction is in part a consequence of the moderated strength of the ]ic C-H bonds. |
|
|
|
|
|
==Safety== |
|
|
{{LD50}} (rats, oral) is 2.68 g/kg. Tetralin induces ].<ref name=Ullmann/> |
|
|
|
|
|
==References== |
|
|
{{reflist}} |
|
|
|
|
|
{{Authority control}} |
|
|
|
|
|
] |
|
|
] |
|
|
] |