Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 2,6-Di-tert-butylphenol: Difference between pages

{{DISPLAYTITLE:2,6-Di-''tert''-butylphenol}}

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477211972

| Name = 2,6-Di-''tert''-butylphenol

| ImageFile = 2,6-di-tert-butylphenol.svg

| ImageSize = 190

| ImageAlt = Structural formula of 2,6-di-tert-butylphenol

| ImageFile1 = 2,6-Di-tert-butylphenol 3D ball.png

| ImageSize1 = 210

| ImageAlt1 = Ball-and-stick model of the 2,6-di-tert-butylphenol molecule

| PIN = 2,6-Di-''tert''-butylphenol

| OtherNames = 2,6-Bis(1,1-dimethylethyl)phenol<br />Dibutylphenol<br />2,6-Bis(''tert''-butyl)phenol<br />2,6-Di(1,1-dimethylethyl)phenol<br />2,6-DTBP<br />Ethanox 701<br />Ethyl 701<br />Ethyl AN 701<br />Irganox L 140<br />Isonox 103<br />TK 12891

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 131421

| PubChem = 31405

| EC_number = 204-884-0

| RTECS = SK8265000

| UNNumber = 2430, 3077

| UNII = 21294V58PF

| SMILES = Oc1c(cccc1C(C)(C)C)C(C)(C)C

|Section2={{Chembox Properties

| C =14 | H=22 | O=1

| Formula =

| MolarMass =

| Appearance = Low-melting colourless solid

| Density =

| MeltingPtC = 34 to 37

| MeltingPt_notes =

| BoilingPtC = 253

| BoilingPt_notes =

| Solubility =

|Section7={{Chembox Hazards

| MainHazards =

| FlashPtC =118

| AutoignitionPt =

| GHSPictograms = {{GHS07}}{{GHS09}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|410}}

| PPhrases = {{P-phrases|264|273|280|302+352|305+351+338|321|332+313|337+313|362|391|501}}

'''2,6-Di-''tert''-butylphenol''' is an [[organic compound]] with the structural formula 2,6-((CH₃)₃C)₂C₆H₃OH. This colorless solid [[alkyl]]ated [[phenol]] and its derivatives are used industrially as [[UV]] stabilizers and [[antioxidant]]s for [[hydrocarbon]]-based products ranging from petrochemicals to plastics.<ref name=Ull>{{Ullmann|title=Antioxidants|author=Peter P. Klemchuk|year=2005|doi=10.1002/14356007.a03_091}}</ref> Illustrative of its usefulness, it prevents gumming in [[aviation fuel]]s.

==Production==

2,6-Di-''tert''-butylphenol is prepared industrially via the [[Friedel–Crafts alkylation]] of phenol with [[isobutene]] catalyzed by [[aluminium phenoxide]]:

:C₆H₅OH + 2 CH₂=C(CH₃)₂ → ((CH₃)₃C)₂C₆H₃OH

In this way, approximately 2.5M kg/y are produced.<ref name=Ullmann>{{Ullmann|author=Helmut Fiege|author2=Heinz-Werner Voges|author3=Toshikazu Hamamoto|author4=Sumio Umemura|author5=Tadao Iwata|author6=Hisaya Miki|author7=Yasuhiro Fujita|author8=Hans-Josef Buysch|author9=Dorothea Garbe|author10=Wilfried Paulus|title=Phenol Derivatives|year=2002|doi=10.1002/14356007.a19_313}}</ref> Alkylation of phenol usually favours the para-position, and a strong [[lewis acid]] such as the Al³⁺ ion is necessary to give selective ortho‑alkylation.<ref>{{cite journal |last1=Kolka |first1=Alfred J. |last2=Napolitano |first2=John P. |last3=Filbey |first3=Allen H. |last4=Ecke |first4=George G. |title=The ortho-Alkylation of Phenols 1 |journal=The Journal of Organic Chemistry |date=June 1957 |volume=22 |issue=6 |pages=642–646 |doi=10.1021/jo01357a014}}</ref><ref>{{cite journal |last1=Küpper |first1=Friedrich-Wilhelm |title=A new mechanism — key for an improved synthesis of 2,6-di-tert-butylphenol |journal=Applied Catalysis A: General |date=June 2004 |volume=264 |issue=2 |pages=253–262 |doi=10.1016/j.apcata.2003.12.043}}</ref> If a conventional [[brønsted acid]] is used then [[2,4-di-tert-butylphenol]] will be produced instead.

==Applications==

Its dominant use is as an antioxidant.

2,6-di-''tert''-butylphenol is a precursor to more complex compounds used as antioxidants and light-protection agents for the [[Stabilizer for polymers|stabilization for polymers]]. Of particular note is methyl-3-(3,5-di-''tert''-butyl-4-hydroxyphenyl)-propionate (CAS# 6386-38-5), which is formed by the [[Michael addition]] of [[methyl acrylate]]. This compound is used as a feedstock in the synthesis of more complex antioxidants such as [[Irganox 1098]]. 2,6-Di-''tert''-butylphenol is also used in the synthesis of [[CGP-7930]], [[probucol]], and [[nicanartine]].

==Safety and regulation==

The {{LD50}} is 9200&nbsp;mg/kg, indicating a low toxicity.<ref name=Ullmann/>

2,6-Di-tert-butylphenol is covered by the U.S. Department of Transportation Code of Federal Regulations 49 CFR 172.101, Appendix B (20 Dec 2004). This substance is designated by the U.S. Department of Transportation (DOT) as a marine pollutant.

==See also==

* [[Butylated hydroxytoluene]]

* [[2,4-di-tert-butylphenol]]

* [[2,4-Dimethyl-6-tert-butylphenol|2,4-Dimethyl-6-''tert''-butylphenol]]

* [[Para tertiary butyl phenol]]

==References==

<references/>

{{Motor fuel}}

{{Antioxidants}}

{{DEFAULTSORT:Di-tert-butylphenol, 2,6-}}

[[Category:Antioxidants]]

[[Category:Alkylphenols]]

[[Category:Fuel antioxidants]]

[[Category:Tert-butyl compounds]]