2,6-Di-tert-butylphenol

changed changed 477211972 2,6-Di-tert-butylphenol 2,6-di-tert-butylphenol.svg 190 Structural formula of 2,6-di-tert-butylphenol 2,6-Di-tert-butylphenol 3D ball.png 210 Ball-and-stick model of the 2,6-di-tert-butylphenol molecule 2,6-Di-tert-butylphenol 2,6-Bis(1,1-dimethylethyl)phenolDibutylphenol2,6-Bis(tert-butyl)phenol2,6-Di(1,1-dimethylethyl)phenol2,6-DTBPEthanox 701Ethyl 701Ethyl AN 701Irganox L 140Isonox 103TK 12891 correct chemspider 29135 changed EBI 131421 1/C14H22O/c1-13(2,3)10-8-7-9-11(12(10)15)14(4,5)6/h7-9,15H,1-6H3 DKCPKDPYUFEZCP-UHFFFAOYAK correct EBI 281071 correct chemspider 1S/C14H22O/c1-13(2,3)10-8-7-9-11(12(10)15)14(4,5)6/h7-9,15H,1-6H3 correct chemspider DKCPKDPYUFEZCP-UHFFFAOYSA-N correct CAS 128-39-2 31405 204-884-0 SK8265000 2430, 3077 21294V58PF Oc1c(cccc1C(C)(C)C)C(C)(C)C 14 22 1 Low-melting colourless solid 34 to 37 253 118 07 09 Warning 315 319 410 264 273 280 302+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 alkylated phenol and its derivatives are used industrially as UV stabilizers and antioxidants for hydrocarbon-based products ranging from petrochemicals to plastics.Antioxidants Peter P. Klemchuk 2005 10.1002/14356007.a03_091 Illustrative of its usefulness, it prevents gumming in aviation fuels. 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.Helmut Fiege Heinz-Werner Voges Toshikazu Hamamoto Sumio Umemura Tadao Iwata Hisaya Miki Yasuhiro Fujita Hans-Josef Buysch Dorothea Garbe Wilfried Paulus Phenol Derivatives 2002 10.1002/14356007.a19_313 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.Kolka Alfred J. Napolitano John P. Filbey Allen H. Ecke George G. The ortho-Alkylation of Phenols 1 The Journal of Organic Chemistry June 1957 22 6 642–646 10.1021/jo01357a014Küpper Friedrich-Wilhelm A new mechanism — key for an improved synthesis of 2,6-di-tert-butylphenol Applied Catalysis A: General June 2004 264 2 253–262 10.1016/j.apcata.2003.12.043 2004AppCA.264..253K If a conventional brønsted acid is used then 2,4-di-tert-butylphenol will be produced instead. Natural occurrence Two species of plants, Jastropa curcas and Metaplexis japonica, contain 2,6-DTBP in seeds.Zhao F Wang P Lucardi RD Su Z Li S Natural Sources and Bioactivities of 2,4-Di-Tert-Butylphenol and Its Analogs. Toxins 6 January 2020 12 1 35 10.3390/toxins12010035 free 31935944 7020479 Applications Its dominant use is as an antioxidant. 2,6-Di-tert-butylphenol is used in the synthesis of 4,4′-biphenol. The process involves oxidative coupling of followed by removal of the tert-butyl groups.Helmut Fiege Heinz-Werner Voges Toshikazu Hamamoto Sumio Umemura Tadao Iwata Hisaya Miki Yasuhiro Fujita Hans-Josef Buysch Dorothea Garbe Wilfried Paulus 3 Phenol Derivatives Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH Weinheim 10.1002/14356007.a19_313 3527306730 2,6-di-tert-butylphenol is a precursor to antioxidants and light-protection agents for the stabilization for polymers. One such case 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 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 is 9200 mg/kg, indicating a low toxicity. 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 Para tertiary butyl phenol References Category:Antioxidants Category:Alkylphenols Category:Fuel antioxidants Category:Tert-butyl compounds