- Cu-Catalyzed carbamoylation: Versus amination of quinoline N -oxide with formamides
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An efficient, direct carbamoylation and amination of quinoline N-oxides with formamides to access 2-carbamoyl and 2-amino quinolines has been developed through copper-catalyzed C-C and C-N bond formations via cross-dehydrogenative coupling reactions. The reaction proceeds smoothly over a broad range of substrates with excellent functional group tolerance under mild conditions. Mechanistic studies suggest that the reaction is initiated by formamide radical or decarbonylative aminyl radical formation in the presence of TBHP, according to the different substituent on the N atom of formamide.
- Zhang, Yan,Zhang, Shiwei,Xu, Guangxing,Li, Min,Tang, Chunlei,Fan, Weizheng
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supporting information
p. 309 - 314
(2019/01/10)
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- Preparation method of 2,6-ditertbutyl p-alkylphenol
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The invention discloses a preparation method of 2,6-ditertbutyl p-alkylphenol. The preparation method comprises the following steps of: 1) adding aqueous or alcohol solution of aldehyde and dimethylamine and alcohol solution of 2,6-ditertbutylphenol into a reaction kettle, and reacting to obtain 2,6-ditertbutyl-4-(dimethylaminoalkyl)phenol, wherein the aldehyde is fatty aldehyde with 1-5 carbon atoms; 2) carrying out catalytic hydrogenolysis on 2,6-ditertbutyl-4-(dimethylaminoalkyl)phenol prepared by the step 1) in the reaction kettle to obtain 2,6-ditertbutyl p-alkylphenol. The preparation method disclosed by the invention has the advantages that the raw materials are low in cost and easy in obtaining, no corrosive waste water is caused, the reaction yield is high and the purity and the yield of a product can be up to 98% or more.
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Paragraph 0029; 0030; 0033; 0036
(2018/07/30)
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- METHODS AND COMPOSITIONS FOR INHIBITING VINYL AROMATIC MONOMER POLYMERIZATION
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Methods and compositions are provided for inhibiting the polymerization of a vinyl aromatic monomer, such as styrene monomer, during elevated temperature processing thereof or during storage or shipment of polymer containing product. The compositions comprise a combination of a quinone methide derivative A) and a phenol compound B). The methods comprise adding from about 1-10,000 ppm of the combination to the monomer containing medium, per one million parts of the monomer.
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- Direct phthalimidomethylation of 2,6-dialkylphenols. Reactions of N-(4-hydroxybenzyl)phthalimides with electrophiles and nucleophiles
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Reactions of 2,6-dialkylphenols with N-(N′,N′- diethylaminomethyl)phthalimide gave the corresponding 4-phthaloylmethylphenols, in which the phthaloyl group can be replaced by an alkylsulfanyl substituent via reactions with thiols. Phthaloylmethylphenols containing the tert-butyl groups that are ortho to the OH group can undergo acid-catalyzed de-tert-butylation.
- Bugaev,Dmitriev,Prosenko
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p. 298 - 302
(2013/06/26)
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- Synthesis and study of the antiradical activity of substituted hydroxybenzylamines and their hydrogen chloride salts
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Different alkylated hydroxybenzylamines and their hydrogen chloride salts were synthesized. The rate constants of their reactions with peroxide radicals k1 and the stoichiometric factors of inhibition f were measured in the initiated oxidation of cumene and methyl oleate. Copyright
- Dyubchenko,Nikulina,Terakh,Kandalintseva,Markov,Grigor'Ev,Prosenko
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p. 330 - 334
(2007/10/03)
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- Method for the preparation of acryloxy- or methacryloxy-functional organosilicon compounds
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A method to make high-purity acryloxy- or methacryloxy-functional organosilicon compounds in high yields by inhibiting gelation of the reaction product during preparation. The method comprises (A) reacting an acrylate or methacrylate ester of an alcohol comprising an aliphatically unsaturated bond or a phenol comprising an aliphatically unsaturated bond with a (B) SiH-functional silicon compound in the presence of (C) a hydrosilylation reaction catalyst and (D) a polymerization inhibitor described by formula STR1 where n is 0 or 1; M is an atom selected from the group consisting of N, P, As, Sb, O, S, Se, Sn, and I; R is a monovalent hydrocarbon group or hydrogen atom; m is 1, 2, or 3; and X is a conjugate base of an organic acid or inorganic acid. The present method can further comprise distillation of the reaction mixture resulting from the reaction of component (A) and (B) in the presence of component (D).
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- Method of treating inflammatory bowel disease
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Provided is a method for treating inflammatory bowel disease in mammals utilizing certain phenol and benzamide compounds.
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- Antioxidant Synergism Between Butylated Hydroxyanisole and Butylated Hydroxytoluene
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Decay of the 2,6-di-tert-butyl-4-methylphenoxy radical in the presence of butylated hydroxyanisole (BHA) was investigated in 1,2-dimethoxyethane with or without triethylamine.BHT-radical was conveniently generated by dissociation of its unstable dimer in solution.The products were BHT, 3,3'-di-tert-butyl-5,5'-dimethoxy-2,2'-dihydroxybiphenyl (BHA-dimer), 2,6-di-tert-butyl-p-quinone methide (QM), 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane, and 3,3',5,5'-tetra-tert-butyl-4,4'-stilbenequinone.The reaction without added triethylamine gave larger quantities of the last two products and BHA (recovery), whereas the reaction with it provided larger quantities of the first two products.The marked difference in the product distribution can be accounted for by a series of reactions including reversible dehydrogenation of BHA with BHT-radical, which generates 2-tert-butyl-4-methoxyphenoxy radical (BHA-radical) and BHT, reversible dimerization of BHA-radical, which affords an intermediary bis(cyclohexadienone), and spontaneous and base-catalysed prototropic rearrangement of the intermediate into BHA-dimer.Products of coupling between BHT-radical and BHA-radical were not obtained.BHA was found to undergo facile acid-catalyzed addition to QM, providing two isomeric bis(hydroxyphenyl)methanes.The results help to elucidate the mechanism of antioxidant synergism between BHA and BHT and may suggest that the synergism can be affected by base or acid. - Key words: Antioxidant synergism; butylated hydroxyanisole; butylated hydroxytoluene; effect of acid; effect of base; fate of phenoxy radicals involved.
- Omura, Kanji
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p. 1565 - 1570
(2007/10/03)
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- Heterocyclic Spirocyclohexadienones from Substituted Phenols
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Mannich bases were prepared from substituted phenols with aliphatic amines and formaldehyde.Amine exchange with N-methyl-2-naphthylamine followed by a Hofmann Martius rearrangement gave rise to o,o'-amino-hydroxy-diphenylmethane derivatives.Under cyclization conditions some of these compounds produced spirocyclohexadienones, which are the ipso analogs to the hypothetic intermediates postulated in the aminomethylation mechanism of phenols. - Keywords: Mannich Reaction; Phenol Dienone Tautomerism; Hofmann Martius Rearrangement
- Moehrle, H.,Schake, D.
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p. 1859 - 1868
(2007/10/03)
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- Method of treating type I diabetes
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Provided is a method for treating Type I diabetes in mammals utilizing certain phenol and benzamide compounds.
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- Method for treating inflammation
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Provided are methods of treating inflammation, arthritis and muscular dystrophy and preventing ischemia-induced cell damage employing certain phenol and benzamide compounds.
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- 2-Propanol derivatives as corrosion inhibitors
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New composition comprises a functional fluid in contact with ferrous metal and a corrosion inhibiting amount of at least one compound of formula (I) STR1 or a derivative thereof in which R1, R2 and R3 are, independently, hydrogen, a C1 -C15 straight or branched chain alkyl residue, a C5 -C12 cycloalkyl residue, a C6 -C15 aryl residue or C7 -C12 alkaryl residue, and R4 and R5 are, independently, hydrogen, 2-hydroxyethyl or 2-hydroxypropyl with the provisos that (a) R4 and R5 are not simultaneously hydrogen, (b) when R4 and R5 are each --CH2 --CH2 --OH, R1 and R2 are not simultaneously hydrogen and R3 is not a pentyl residue and (c) that polyalkylene and phenol or polycarboxylic ester co-additives are absent; as well as salts thereof. Some of the compounds of formula I are new.
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- Corrosion inhibiting composition
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A composition, in contact with a corrodable metal surface, which composition comprises: (a) an aqueous-based or oil-based system; and (b) as inhibitor for protecting the metal surface against corrosion, at least one compound having the formula I: STR1 as well as salts or partial esters thereof wherein: n is 0 or an integer ranging from 1 to 20, R is a straight or branched chain C4 -C30 alkyl group, optionally interrupted by one, two or three oxygen atoms or substituted by one, two or three hydroxy groups, a C5 -C12 cycloalkyl group, a C6 -C10 aryl group optionally substituted by one, two or three C1 -C12 alkyl groups, or a C7 -C13 aralkyl group which is optionally substituted by a hydroxyl group; R1 is H or a straight- or branched chain C1 -C4 alkyl group; R2 is H, a straight or branched chain C1 -C4 alkyl group or CO2 H; R3 is H, a straight or branched chain C1 -C4 alkyl group, --CH2 CO2 H or --CH2 CH2 CO2 H; R4 is H, a straight or branched chain C1 -C4 alkyl group or CO2 H; R5 is H, a straight or branched chain C1 -C4 alkyl group, CH2 CO2 H or CH2 CH2 CO2 H; provided that at least one group R4 must be CO2 H, with the provisio, that compositions comprising an oil-based system and a compound having the formula STR2 wherein R, R1 and R2 are hydrogen or alkyl radicals, having a total from 10 to 38 C-atoms, are excluded.
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- Triazole-organodithiophosphate reaction product additives for functional fluids
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New reaction products, useful as additives for functional fluids, are obtained by reacting, at elevated temperature, (A) a triazole having the formula IA or IB: STR1 wherein R7 is hydrogen or a C1 -C20 alkyl residue; R8 and R9 are the same or different and each is C1 -C20 alkyl, C3 -C20 alkenyl, C5 -C12 cycloalkyl, C7 -C13 aralkyl, C6 -C10 aryl or R8 and R9, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered heterocyclic residue or R8 and R9 is each a residue of formula: wherein X is O, S or N(R12), R12 is hydrogen or C1 -C20 alkyl, "alkylene" is a C1 -C12 alkylene residue and n is 0 or an integer from 1 to 6; R10 is hydrogen, C1 -C20 alkyl or C6 -C10 aryl or C7 -C18 alkyl phenyl; and R11 is hydrogen, C1 -C20 alkyl or a residue --CH2 NR8 R9 wherein R8 and R9 have their previous significance; with (B) an organodithiophosphate having the formula: STR2 in which R13 is a C1 -C20 alkyl or C7 -C18 alkyl phenyl or C7 -C13 aralkyl group, M is a metal ion of Group IA, IB, IIA, IIB, VB, VIB, VIIB or VIII of the Periodic System of Elements, and y is the valency of M.
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- SYNTHESIS OF SOME THIOMETHYL DERIVATIVES OF 2,6-DI-tert-BUTYLPHENOL AND THEIR ANTIOXIDANT CHARACTERISTICS
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The reactions of 3,5-di-tert-butyl-4-hydroxybenzyl-N-N-dimethylamine with various thiols leads to the formation of 3,5-di-tert-butyl-4-hydoxybenzyl alkyl (aryl) sulfides.By means of their electrochemical oxidation at a stationary graphite microelectrode in aqueous media over a wide range of pH it was established that the new sulfides have the same level of antiradical activity as ionole. 3,5-Ditert-butyl-4-hydroxybenzyl sulfide is the most easily oxidized.
- Bilalov, S. B.,Alieva, F. D.,Gasanov, B. R.
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p. 1355 - 1357
(2007/10/02)
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- Method of producing 2,6-dialkyl- and 2,6-diaralkyl-substituted derivatives of p-cresol
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A method of producing 2,6-dialkyl- and 2,6-diaralkyl-substituted derivatives of p-cresol of the general formula SPC1 Wherein R signifies an alkyl group having from 4 to 12 carbon atoms or SPC2 Comprising subjecting phenol to alkylation with olefines having from 4 to 12 carbon atoms or with styrene at a temperature of 50°-150°C in the presence of a catalyst, namely, aluminum, taken in an amount of 0.1-5 wt.% of phenol. 2,6-Dialkyl phenol or 2,6-diaralkyl phenol resulting after from the alkylation is treated with a mixture of formaldehyde and dimethylamine or with a product of their interaction having the formula EQU1 at a temperature of 20°-100°C with subsequent catalytic hydrogenolysis of N,N-dimethyl(3,5-dialkyl-4-hydroxybenzyl)/amine or N,N-dimethyl(3,5-diaralkyl-4-hydroxybenzyl/amine at a temperature of 80°-200°C., molar ratio of hydrogen to the product being treated of 1-5:1 and space velocity of 0.1-2 hour-1. The products produced by said method feature a high degree of purity, and they can be employed as effective inhibitors of thermooxidation degradation of polymers and hydrocarbon fuels, and also as intermediates for producing p-cresol, and 2-alkyl- and 2-aralkyl-substituted derivatives of p-cresol.
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