1138-52-9Relevant articles and documents
Development of 3,5-Di- tert -butylphenol as a Model Substrate for Biomimetic Aerobic Copper Catalysis
Kwon, Ohhyeon,Esguerra, Kenneth Virgel N.,Glazerman, Michael,Petitjean, Laurène,Xu, Yalun,Ottenwaelder, Xavier,Lumb, Jean-Philip
, p. 1548 - 1553 (2017)
We develop 3,5-di- tert butylphenol as a strategic substrate for the evaluation of biomimetic Cu 2 -O 2 complexes intended to mimic the activity of tyrosinase. We describe a practical and scalable synthesis and validate its use in an aerobic ortho -oxygenation catalyzed by N, N ′-di- tert -butylethylenediamine and [Cu(CH 3 CN) 4 ]PF 6.
An unusually unstable ortho-phosphinophenol and its use to prepare benzoxaphospholes having enhanced air-stability
Wu, Shanshan,Deligonal, Nihal,Protasiewicz, John D.
, p. 14866 - 14874 (2013)
The primary phosphine 3,5-di-tert-butyl-2-phosphinophenol has been prepared and characterized. Oddly, the presence of a sterically demanding tert-butyl group adjacent to the PH2 centre renders the molecule very sensitive to loss of PH3 and formation of 3,5-di-tert-butyl-phenol in chloroform solutions in the presence of air. The process was catalyzed by HCl and dependent on the purity of CDCl3. Despite the instability of 3,5-di-tert-butyl-2-phosphinophenol, this material could be employed to produce a series of luminescent 2-R-4,6-di-tert-butyl-1,3-benzoxaphospholes having greater air stability than corresponding less bulky 2-R-1,3-benzoxaphospholes.
Highly selective conversion of guaiacol to: Tert -butylphenols in supercritical ethanol over a H2WO4 catalyst
Mai, Fuhang,Cui, Kai,Wen, Zhe,Wu, Kai,Yan, Fei,Chen, Mengmeng,Chen, Hong,Li, Yongdan
, p. 2764 - 2771 (2019/02/01)
The conversion of guaiacol is examined at 300 °C in supercritical ethanol over a H2WO4 catalyst. Guaiacol is consumed completely, meanwhile, 16.7% aromatic ethers and 80.0% alkylphenols are obtained. Interestingly, tert-butylphenols are produced mainly with a high selectivity of 71.8%, and the overall selectivity of 2,6-di-tert-butylphenol and 2,6-di-tert-butyl-4-ethylphenol is as high as 63.7%. The experimental results indicate that catechol and 2-ethoxyphenol are the intermediates. Meanwhile, the WO3 sites play an important role in the conversion of guaiacol and the Br?nsted acid sites on H2WO4 enhance the conversion and favour a high selectivity of the tert-butylphenols. The recycling tests show that the carbon deposition on the catalyst surface, the dehydration and partial reduction of the catalyst itself are responsible for the decay of the H2WO4 catalyst. Finally, the possible reaction pathways proposed involve the transetherification process and the alkylation process during guaiacol conversion.
Preparation method of 3,5-di-tert-butylphenol
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Paragraph 0031; 0032; 0036; 0041; 0046; 0051; 0056; 0061, (2018/09/08)
The invention relates to the field of organic synthesis, in particular to a preparation method of 3,5-di-tert-butylphenol.The method comprises the following steps of (1) adding 1,3-di-tert-butylbenzene and aluminum trichloride into an organic solvent; performing stirring; adding isopropanol and boron trifluoride diethyl etherate complexes; performing heating and stirring; (2) performing liquid separation and organic phase rectification; (3) adding 1,3-di-tert-butyl-5-isopropyl benzene, benzotrifluoride, N-hydroxyphthalimide, azodiisobutyronitrile and sodium carbonate into a reaction bottle; performing heating and stirring; (4) adding dilute sulphuric acid into reaction liquid obtained in the step (3); performing heating stirring, and still standing layering; performing organic phase rectification and drying; then, obtaining a 3,5-di-tert-butylphenol product. The preparation method provided by the invention has the advantages that the reaction conditions are mild; the preparation process is simple; the product yield is high.
Method for preparing hydrocarbyl phenol by catalytic conversion of phenolic compound in presence of molybdenum-based catalyst
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Paragraph 0043-0044; 0070, (2018/04/02)
The invention discloses a method for preparing hydrocarbyl phenol by catalytic conversion of a phenolic compound in the presence of a molybdenum-based catalyst. The method comprises mixing a phenoliccompound, a molybdenum-based catalyst and a reaction solvent, adding the mixture into a sealed reactor, feeding gas into the reactor, heating the mixture to 150-350 DEG C, carrying out stirring for areaction for 0.5-2h, then filtering to remove a solid catalyst and carrying out rotary evaporateion to obtain a liquid product. The phenolic compound has a wide source, a cost is low, product alkyl phenol selectivity is high, an added value is high, alcohol or an alcohol-water mixture is used as a reaction solvent, environmental friendliness is realized, pollution is avoided, any inorganic acids and alkalis are avoided in the reaction process, the common environmental pollution problems in the biomass processing technology are solved, the reaction conditions are mild, the process can be carried out at a low temperature, high-efficiency conversion of the reactants can be realized without consuming hydrogen gas and the method is suitable for large-scale industrial trial production.
Synthesis of ortho-Azophenols by Formal Dehydrogenative Coupling of Phenols and Hydrazines or Hydrazides
Esguerra, Kenneth Virgel N.,Lumb, Jean-Philip
supporting information, p. 8596 - 8600 (2017/06/30)
Azophenols are important chromophores and reagents in organic synthesis, with applications as pigments and molecular switches. Here, we describe a catalytic aerobic process that couples phenols and hydrazines or hydrazides for their synthesis. The key aromatic C?N bond is formed by condensation between the hydrazine or hydrazide and an ortho-quinone, which triggers a redox-isomerization to install the azo-functionality. Notable features include rapid access to highly functionalized azophenols with a range of electronic configurations, including “push–pull” systems, conditions that employ simple, unactivated substrates, occurrence at room temperature using an earth-abundant and commercially available copper catalyst, and production of water as the only stoichiometric byproduct.
METHOD FOR PRODUCING AN ARENE WITH AN AROMATIC C-N BOND ORTHO TO AN AROMATIC C-O BOND
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Paragraph 0358; 0359; 0360, (2017/03/28)
A method for producing an arene with an aromatic C—N bond ortho to an aromatic C—O bond from a hydroxy arene comprising said aromatic C—O bond is provided. This method comprising the steps a) ortho-oxygenating the hydroxy arene to produce an ortho-quinone, b) condensating the ortho-quinone with a nitrogen nucleophile to generate a compound of Formula (IVa) or (IVb), and c) allowing 1,5-hydrogen atom shift of the compound of Formula (IVa) or (IVb), thereby producing arenes with a C—N bond ortho to a C—O bond of Formula (Va) and (Vb), respectively:
Directional molecular transportation based on a catalytic stopper-leaving rotaxane system
Meng, Zheng,Xiang, Jun-Feng,Chen, Chuan-Feng
, p. 5652 - 5658 (2016/05/24)
Ratchet mechanism has proved to be a key principle in designing molecular motors and machines that exploit random thermal fluctuations for directional motion with energy input. To integrate ratchet mechanism into artificial systems, precise molecular design is a prerequisite to control the pathway of relative motion between their subcomponents, which is still a formidable challenge. Herein, we report a straightforward method to control the transportation barrier of a macrocycle by selectively detaching one of the two stoppers using a novel DBU-catalyzed stopperleaving reaction in a rotaxane system. The macrocycle was first allowed to thread onto a semidumbbell axle from the open end and subsequently thermodynamically captured into a nonsymmetrical rotaxane. Then, it was driven energetically uphill until it reached a kinetically trapped state by destroying its interaction with ammonium site, and was finally quantitatively released from the other end when the corresponding stopper barrier was removed. Although the directional transportation at the present system was achieved by discrete chemical reactions for the sake of higher transportation efficiency, it represents a new molecular transportation model by the strategy of using stopper-leavable rotaxane.
Chemo- and Regioselective Hydrogenolysis of Diaryl Ether C-O Bonds by a Robust Heterogeneous Ni/C Catalyst: Applications to the Cleavage of Complex Lignin-Related Fragments
Gao, Fang,Webb, Jonathan D.,Hartwig, John F.
supporting information, p. 1474 - 1478 (2016/02/12)
We report the chemo- and regioselective hydrogenolysis of the C-O bonds in di-ortho-substituted diaryl ethers under the catalysis of a supported nickel catalyst. The catalyst comprises heterogeneous nickel particles supported on activated carbon and furnishes arenes and phenols in high yields without hydrogenation. The high thermal stability of the embedded metal particles allows C-O bond cleavage to occur in highly substituted diaryl ether units akin to those in lignin. Preliminary mechanistic experiments show that this catalyst undergoes sintering less readily than previously reported catalyst particles that form from a solution of [Ni(cod)2].
BIPHENOL COMPOUND, OLEFIN POLYMERIZATION CATALYST USING THE SAME, AND OLEFIN POLYMER PRODUCTION METHOD
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, (2017/01/26)
PROBLEM TO BE SOLVED: To provide a transition metal complex having a quadridentate ligand allowing inexpensive production through a simple synthetic route, which forms a polymerization catalyst with high catalytic activity enabling polymerization of a high-molecular mass olefin. SOLUTION: The biphenol compound is represented by general formula (1). (Q1 and Q2 are C1-20 divalent hydrocarbon groups or the like; Q3 to Q8 are H, C1-20 hydrocarbon groups or the like; T1 and T2 are C6-20 aryloxy groups, amino groups or the like; and m and n are from 0 to 2.) COPYRIGHT: (C)2015,JPOandINPIT
