cas 1879-09-0, 2-(tert-Butyl)-4,6-dimethylphenol

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Stevens
p. 655,659
(1943)
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Chemical Kinetics of the Alkylation of Xylenol for the Separation of Their Close-Boiling Isomers from Coal Tar
Abstract: To support the industrial design and process development for the separation of xylenol isomers from coal tar, the present work was focused on 2,4/2,5-xylenol mixture as 2,4-xylenol and 2,5-xylenol have very close boiling points. Specifically, th
Cong-Yu, Ke,Lu, Guo-Min,Sun, Wu-Juan,Tang, Xuan,Wei, Ying-Lin,Zhang, Qun-Zheng,Zhang, Xiao-Xia,Zhang, Xun-Li
p. 1291 - 1299
(2020/12/02)

Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates
The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.
Hui, Zi,Jiang, Songwei,Qi, Xiang,Ye, Xiang-Yang,Xie, Tian
supporting information

(2020/05/18)

Highly selective conversion of guaiacol to: Tert -butylphenols in supercritical ethanol over a H2WO4 catalyst
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.
Mai, Fuhang,Cui, Kai,Wen, Zhe,Wu, Kai,Yan, Fei,Chen, Mengmeng,Chen, Hong,Li, Yongdan
p. 2764 - 2771
(2019/02/01)

Phenol o-position alkylation method
The invention provides a phenol o-position alkylation method which comprises the following step: in the presence of a catalyst, a phenol substance and an alkylating agent react, wherein the catalyst is an aryl zinc salt generated from a reaction of zinc and a phenol compound; the alkylating agent is olefin; the phenol substance comprises polyphenol such as catechol and hydroquinone, and further comprises one to two alkyl groups, or halide based phenols; the alkyl group is straight-chain or branched paraffin with 1-10 carbons. By adopting the phenol o-position alkylation method, the preparation efficiency is greatly improved, and the conversion rate can be further increased. The invention further provides a method for preparing 2,6-di-tert-butyl-4-methylphenol, and a reaction kettle for preparation.
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Paragraph 0045; 0046; 0047; 0048

(2017/08/27)

About selective methods of synthesis of 6-tert-butyl-2-methylphenol and 6-tert-butyl-2,4-dimethylphenol
Vapor phase catalytic methylation with methanol of 2-tert-butylphenol at the temperature 280-300°C proceeds selectively with formation of 6-tert-butyl-2-methylphenol. Elevating reaction temperature above 300°C leads to formation of 2,6-dimethylphenol. Reaction of 2-tert-butylphenol with methanol in alkaline medium in the presence of zinc oxide is shown to lead initially to formation of a mixture of calixarenes and methylenebisphenols that at elevated temperature exert splitting leading in future to 6-tert-butyl-2,4-dimethylphenol. Obtaining it in this reaction from 2,2′-methylenebis-(6-tert-butyl-4-methylphenol) proceeds selectively. Pathways of the reductive methylation of methylenebisphenols with methanol in alkaline medium is considered.
Krysin,Khlebnikova,Khlebnikov,Pokrovskii,Vasil'ev
p. 1156 - 1162
(2011/05/04)

4-Formyl amino-n-methylpiperidine derivatives, the use thereof as stabilisers and organic material stabilised therewith
The present invention relates to 4-formylamino-N-methylpiperidine derivatives of the formula (I) where the variables are as defined in the Description, to a process for preparing these piperidine derivatives, to the use of these piperidine derivatives of the invention, or prepared according to the invention, for stabilizing organic material, in particular for stabilizing plastics or coating materials, and also to the use of these piperidine derivatives of the invention, or prepared according to the invention, as light stabilizers or stabilizers for wood surfaces. The present invention further relates to stabilized organic material which comprises these piperidine derivatives of the invention or prepared according to the invention.
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(2008/06/13)

Thioether substituted hydroxybenzophenones and stabilized compositions
2-Hydroxybenzophenone derivatives substituted in the 4′-position by a thioether moiety exhibit enhanced absorption in the UV at longer wavelength. Compositions comprising organic material subject to actinic degradation are beneficially stabilized with such derivatives.
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(2008/06/13)

Color-stabilized basic monomers, process for producing the same and method for handling the same
Color-stabilized basic monomers are provided. Said basic monomers are obtained by adding, to a basic monomer ?e.g. an N,N-dialkylaminoalkyl (meth)acrylate or an N,N-dialkylaminoalkyl (meth)acrylamide!, at least one member selected from the group consisting of amido group-containing compounds, phosphorous acid esters, phosphoric acid esters and phosphines and at least one phenol compound represented by the general formula: STR1 wherein R5, R6, R8 and R9 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; and R7 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. The color-stabilized basic monomers are more resistant to coloration when they are handled under such conditions that the oxygen concentration in the gas phase contacting therewith is 0.01 to 10% by volume.
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(2008/06/13)

Lubricant composition
A composition comprising a) a lubricant or a hydraulic fluid and b) at least one compound of the general formula I STR1 in which x=1 or 2 and, if x=1, R is as defined for R1 or R3 --O-- or, if x=2, R is as defined for R8, and R1 and R3 are, for example, alkyl, cycloalkyl, alkenyl, phenyl, naphthyl, aralkyl or alkaryl, or alkyl, cycloalkyl, alkenyl, phenyl, naphthyl, aralkyl or alkaryl, which are monosubstituted or polysubstituted by groups from the series comprising halogen, cyano, nitro, e.g. --OCH3 or e.g. --COOCH3, or alkyl, cycloalkyl, alkenyl, aralkyl or alkaryl which are interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR2 or alkyl, cycloalkyl, alkenyl, aralkyl or alkaryl which are monosubstituted or polysubstituted by groups from the series comprising halogen, cyano, nitro, e.g. --OCH3 or e.g. --COOCH3 and interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR3 and R2 is NR4 R5, --OR6 or --SR7, and R4 and R5 are identical or different and are, for example, --H, alkyl, phenyl, naphthyl, aralkyl or alkaryl, or R4 and R5, together with the N atom linking them, form, for example, a piperidine or morpholine radical, and R6 and R7 can be alkyl which may be interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR4 or are, for example, phenyl, naphthyl, alkaryl or aralkyl, and R8 can be alkylene which may be interrupted by at least one --O-- group or alkylidene which may be interrupted by at least one --O-- group. Some of the compounds of the formula I are novel. The compositions show an improved stability towards oxidative degradation, confer protection under extreme pressures and reduce frictional wear.
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(2008/06/13)

Substituted 1,4-diamino-2-butene stabilizers
N,N,N',N'-Tetrasubstituted 1,4-diamino-2-butenes where the substituents are alkyl, cycloalkyl, aralkyl, aryl or mixtures thereof provide effective antioxidant protection to lubricants and/or synthetic polymers.
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(2008/06/13)

2-(2-hydroxy-3-perfluoroalkyl thiomethyl-5-alkylphenyl)2H-benzotriazoles and stabilized compositions thereof
2-(2-Hydroxy-3-perfluoroalkylthiomethyl-5-alkylphenyl)-2H-benzotriazoles are prepared by reacting the Mannich base hydrohalide or quaternary salt of a 2-(2-hydroxy-5-alkylphenyl)-2H-benzotriazole with a perfluoroalkyl mercaptan. The products exhibit outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the processing of stabilized compositions at elevated temperatures.
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(2008/06/13)

Substituted 1-aminonaphthalenes and stabilized compositions
Substituted 1-aminonaphthalenes of formula I STR1 wherein n is 1-3, Ar is arylene, R1 and R2 are independently hydrogen, alkyl or phenyl, R3 is hydrogen, alkyl or substituted alkyl, and R4 and R5 have independently the same definitions as R3 or are independently aryl, substituted aryl or cycloalkyl, are effective stabilizers for lubricating oil or polymer compositions. The instant compounds are particularly effective in lubricating oil compositions when used with a diarylamine antioxidant.
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(2008/06/13)

New triazole compounds
New triazole compounds, useful as metal deactivators and/or antioxidants in organic material, having the formula I: wherein X is the triazole residue of formula II: or the benzotriazole residue of formula III or IIIA: in which R is hydrogen or methyl.
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(2008/06/13)

Triazole compounds useful as metal deactivators
Composition comprising a functional fluid or fuel susceptible to degradation by a metal; and b) a metal deactivator having the formula I: in which X is a group having the formula II or III: in which R is hydrogen or C1-C4 alkyl. The compounds of formula I are new.
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(2008/06/13)

2-Propanol derivatives as corrosion inhibitors
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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(2008/06/13)

Corrosion inhibiting composition
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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(2008/06/13)

N-substituted tetrahydroquinolines for use as antioxidants in lubricants
Compounds useful as additives for lubricants, hydraulic oils and metal-working fluids include those of formula IV STR1 where R1 and R2 are independently alkyl or substituted aryl, R3 and R13 are independently hydrogen or methyl, R6 is alkyl, alkenyl, aralkyl or substituted benzyl, and R15 and R16 are independently hydrogen, alkyl, aryl or aralkyl.
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(2008/06/13)

Mercaptotriazine derivatives as lubricant additives
Compounds of the formula STR1 and of the formula STR2 in which X and X' are, for example, --S--CHR1, --NR2 R3, --S--R3, --NR2 R3 or --OR3, R1 is, for example, --H, alkyl, cycloalkyl or phenyl, R2 and R3 are, for example, --H, alkyl, cycloalkyl or phenyl, or R2 and R3 together form a 3- to 7-membered heterocyclic ring, and R is alkylene, and compositions containing at least one compound of the formulae I and/or II and at least one lubricant, one hydraulic fluid or one metal working fluid, the compounds of the formula I and/or II being used as extreme pressure and wear-reducing additives.
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(2008/06/13)

Lubricant compositions
The present invention provides a lubricant composition comprising a lubricating oil and, as multifunctional additive, at least one compound having the formula I: or amine salts thereof; wherein R1 and R2, independently, are hydrogen or methyl; n and m, independently, are 0 or 1; and X is SR3 or NR4R3 wherein R3 is C12-C20 linear or branched alkyl R4 and R5 are independently, C8-C20 linear or branched aikyl provided that those compounds of formula I are excluded in which m and n are each 0, X is S-C8-C20 linear or branched alkyl and R1 and R2 are as defined.
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(2008/06/13)

Corrosion inhibition
The present invention provides a composition in contact with a corrodable metal surface, comprising a functional fluid and, as corrosion inhibitor, a compound having the formula I: as well as salts or esters thereof, wherein, R1 is C4-C20 linear or branched alkyl, phenyl or C7-C20 alkylphenyl;, R2 is C1-C12 linear or branched alkyl, phenyl or C7-C20 alkylphenyl, or arylalkyl containing 7-20 carbon atoms;, X is CH2, O or S;, Y is O or S; and, Z is -(CH2)n- in which n is 1, 2, 3, 4 or 5, or Z is -CH2-CH(CH3)-. Some of the compounds of formula I are new.
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(2008/06/13)

Methylphosphonic acid amine salt lubricant additives
Novel salts of methylphosphonic acid with primary amines are described. These compounds are preferably used as extreme pressure additives in lubricant compositions.
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(2008/06/13)

Sulfur-containing compounds as antioxidants for lubricants and elastomers
Compounds of the formula (I) STR1 in which the Rs independently of one another are H, phenyl, naphthyl or C7 -C30 alkaryl and R1 is H, C1 -C8 alkyl, C7 -C9 aralkyl, C5 -C12 cycloalkyl, phenyl, naphthyl, C7 -C30 alkaryl or a group of the formula (II) R2 is C7 -C30 alkaryl, phenyl, naphthyl or phenyl containing, in the para-position, an HO or C1 -C18 alkoxy group or a group of the formulae STR2 or R1 and R2, together with the nitrogen atom to which they are attached, are a radical of the formula (III) STR3 R3 is a radical of the formulae --(CH2)b --COOR6 or --(CH2)2 OCOR7, a is the number 1, 2 or 3 and b is the number 1 or 2, and R4 is phenyl or a group of the formula (II), the two R5 s independently of one another are H, C1 -C24 alkyl, C5 -C12 cycloalkyl or C7 -C9 aralkyl, and R6 is H, C1 -C18 alkyl or benzyl, R7 is C1 -C14 alkyl, phenyl or a group of the formula in which Y is --O-- or --S--, a is the number 1, 2 or 3 and m is the number 1 or 2, B is a direct bond, --S--, --S--S-- or a C1 -C12 alkylene radical, X in the formula (III) is a direct bond, --S-- or a group of the formulae STR4 form a phenothiazine, phenazine, acridine or carbazole radical.
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(2008/06/13)

1,4-Oxathianones and 1,4-oxathiepanones
The compounds of the formula STR1 in which R is C1 -C24 alkyl, C3 -C20 alkenyl, C5 -C6 cycloalkyl, unsubstituted or C1 -C4 alkyl-substituted phenyl or phenyl-C1 -C4 alkyl, n is 1 or 2, and X is S or O, are highly suitable as additives, in particular as antiwear and high-pressure additives, and as corrosion inhibitors in functional fluids, for example in lubricants, fuels, hydraulic fluids, metal-working fluids and drilling fluids.
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(2008/06/13)

Hydroxyether-carboxylic acids and lactones thereof, process for their production and their use as corrosion inhibitors
A composition, in contact with a corrodable metal surface, comprising: a) an aqueous-based or oil-based system; and b) as an inhibitor for protecting the metal surface against corrosion, at least one compound having the formula I or II: in which, R is C4-C20alkyl, C4-C20alkyl interrupted by one or more oxygen atoms, C4-C20alkenyl, C6-C10aryl, C7-C15alkaryl, C7-C15aralkyl or C5-C12cyclo-alkyl;, R1, R2 and R3 are the same or different and each is methyl or, preferably, hydrogen;, M is hydrogen, a metal ion, ammonium or substituted ammonium ion;, a is 0 or 1;, b is 0 or an integer from 1 to 6, preferably 0, 1, 2 or 3 especially 0 or 1; and, c is an integer from 1 to 6; and/or at least one compound having the formula II: in which R, R3 and a are as defined above.
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(2008/06/13)

Triazole-organodithiophosphate reaction product additives for functional fluids
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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(2008/06/13)

THE 2,2'-SPIROBICHROMAN - 1,1'-SPIROBIINDAN-4,4'-DIOL REARRANGEMENT. II
The reaction of 2,2'-spirobichroman derivatives with either hydrobromic acid in the acetic acid solution or aluminum chloride in the chlorobenzene solution yielded 1,1'-spirobiindan-4,4'-diol analogues.The reaction is peculiar as compared with the reaction of alkyl aryl ethers with the same reagents in the same media.
Tanaka, Tsuguo,Miyaguchi, Masao,Mochisuki, Rosalina K.,Tanaka, Senichiro,Okamoto, Masaya,et al.
p. 463 - 484
(2007/10/02)

Chemical process
Phenols with a methyl group substituted on the phenolic benzene ring, such as 2,6-di-tert-butyl-p-cresol, can be produced by reacting a halomethyl group substituted on a phenol such as 2,6-di-tert-butyl-4-chloromethylphenol, with hydrogen in the presence of a hydrogenation catalyst, such as palladium.
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(2008/06/13)

Dual purpose stabilizer compounds and polymer compositions containing same
Diesters of partially hindered mercaptophenols and 3,5-di-alkyl-4-hydroxybenzoic acid and its corresponding acid salt, wherein such diester corresponds to the following formula STR1 wherein R and R1 are the same and are selected from among the following STR2 with R6 and R7 being an aliphatic hydrocarbon radical of 3 to 10 carbon atoms; and y being 0-5; R2 is a tertiary aliphatic hydrocarbon radical having from 4 to 10 carbon atoms or an alicyclic hydrocarbon radical having from 4 to 10 carbon atoms, where the carbon atom of attachment to the aromatic ring is fully substituted; R3 is hydrogen, halogen, an aliphatic hydrocarbon radical having from 1 to 10 carbon atoms or an alicyclic hydrocarbon radical having from 3 to 10 carbon atoms; and R4 and R5 is STR3 where WHERE A and A' are independently selected from among hydrogen, an aliphatic hydrocarbon radical of 1 to 10 carbon atoms or an alicyclic hydrocarbon radical of 3 to 10 carbon atoms. The above diesters are highly effective stabilizers of polyolefins against oxidative degradation and also impart a modest degree of protection and such materials against UV degradation.
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(2008/06/13)

Compounds containing both urea and urethane groups
Novel compounds of the general formula: STR1 wherein R and R2 are hydrocarbyl groups, R1 is a hydrocarbylene group and R3 is hydrogen or a hydrocarbyl group, which groups R, R1, R2 and R3 may be substituted by or contain one or more heteroatoms or heterogroups, have utility as antioxidants for organic materials such as lubricating oils.
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(2008/06/13)