cas 88-58-4, 2,5-Di-tert-butylhydroquinone

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Preparation method of 2, 5-di-tert-butyl-p-dimethoxybenzene
The invention discloses a preparation method of 2, 5-di-tert-butyl-p-dimethoxybenzene, which comprises the following steps: (1) reacting tert-butyl alcohol with hydroquinone in a first solvent under the action of a first catalyst, cooling and crystallizing after the reaction is finished, filtering, washing and drying to obtain 2,5-di-tert-butyl hydroquinone; and (2) reacting the 2, 5-di-tert-butyl hydroquinone obtained in the step (1) with methyl iodide in a second solvent under the action of a second catalyst, cooling to room temperature after the reaction is finished, adding brine and an organic solvent into the reaction liquid for extraction, washing the obtained organic layer, and performing vacuum drying to obtain the 2, 5-di-tert-butyl-p-dimethoxybenzene product. The method has the advantages of simple process, mild reaction conditions, environmental protection, low cost and high yield.
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Paragraph 0033-0035; 0038-0040; 0043-0045; 0048-0050; 0053

(2021/06/02)

A PROCESS FOR PREPARATION OF TERTIARY BUTYL HYDROQUINONE
A PROCESS FOR PREPARATION OF TERTIARY BUTYL HYDROQUINONE The present invention relates to a process for preparation of tertiary butyl hydroquinone. More particularly, it relates to a process for preparation 5 of TBHQ by eradicating the consumption of hazardous solvents like toluene and eliminating hazardous impurities like hydroquinone, tertiary butyl‐p‐benzoquinone and also drastically reducing the presence of heavy metals like lead and arsenic. The present invention includes stages I‐IV in which TBHQ is more purified and precipitated with a high scale purity results. TBHQ has 10 application in food additives, animal feeds, as an antioxidant, emulsifier and in edible oils, effectively as antioxidant.
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Page/Page column 9; 10; 11

(2020/07/15)

1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones
Pro-aromatic and volatile 1-methyl-1,4-cyclohexadiene (MeCHD) was used for the first time as a valid H-atom source in an innovative method to reduce ortho or para quinones to obtain the corresponding catechols and hydroquinones in good to excellent yields. Notably, the excess of MeCHD and the toluene formed as the oxidation product can be easily removed by evaporation. In some cases, trifluoroacetic acid as a catalyst was added to obtain the desired products. The reaction proceeds in air and under mild conditions, without metal catalysts and sulfur derivatives, resulting in an excellent and competitive method to reduce quinones. The mechanism is attributed to a radical reaction triggered by a hydrogen atom transfer from MeCHD to quinones, or, in the presence of trifluoroacetic acid, to a hydride transfer process.
Baschieri, Andrea,Amorati, Riccardo,Valgimigli, Luca,Sambri, Letizia
p. 13655 - 13664
(2019/10/28)

Reactivity of iPrPCPIrH4 with para-benzoquinones
In the interest of investigating new hydrogen acceptors for pincer–iridium catalyzed dehydrogenations with the ability to be catalytically recycled, a series of para-benzoquinones have been reacted with iPrPCPIrH4 in various solvents and conditions. Preliminary results indicate that a wide range of quinones are capable of dehydrogenating iPrPCPIrH4, and that several turn-overs in alcohol dehydrogenation by iPrPCPIr are possible at room temperature using benzoquinone acceptors. However, strong acceptor–catalyst interactions are inhibitory toward catalysis when the acceptor is used in excess. A new class of (bis)-η2 pi-adducts, formed between iPrPCPIr and benzoquinones, nicknamed “barber-chairs”, has been identified and 3 examples have been characterized.
Wilklow-Marnell, Miles,Brennessel, William W.,Jones, William D.
p. 209 - 214
(2017/11/24)

Diels-Alder trapping of in situ generated dienes from 3,4-dihydro-2H-pyran with p-quinone catalysed by p-toluenesulfonic acid
This comprehensive study portrays that p-toluenesulfonic acid is a more efficient catalyst for the reaction between p-quinones and 3,4-dihydro-2H-pyran, than the Lewis acids. The products were accomplished by the Diels-Alder cycloaddition reaction and their mechanistic pathways have been formulated. The impact of C2 and C2,5 substituents of the p-quinones on the cycloaddition reaction has been explored. Remarkably, it is the first report to explore this kind of in situ generated diene for the Diels-Alder cycloaddition reaction.
Mohan Raj, Radhakrishnan,Balasubramanian, Kalpattu K.,Easwaramoorthy, Deivanayagam
p. 1115 - 1121
(2017/02/10)

Production of martite nanoparticles with high energy planetary ball milling for heterogeneous Fenton-like process
Natural martite microparticles (NMMs) were prepared with a high energy planetary ball mill to form a nanocatalyst for a Fenton-like process. Martite nanoparticles (MNs) of different scales are formed when the milling time ranges from 1 to 5 h at the milling speed of 300 rpm. The catalytic performances of MNs are higher than the NMMs for the degradation of acid blue 5 (AB5) in a heterogeneous Fenton-like process. The NMMs and the MNs were characterized by SEM, EDX, BET, XRD and FT-IR analyses. The size distribution of the 5 h milled martite nanoparticles (MN3) is in the range of 20 nm to 100 nm, and these have the highest surface area (19.23 m2 g-1). The influence of the main operational parameters, including initial pH, MN3 dosage, H2O2 and initial dye concentration, were investigated on the AB5 degradation. The treatment process obeys pseudo first order kinetics and some of the degradation intermediates were recognized by the GC-MS method. The environmentally-friendly production of the MNs, low amount of leached iron and repeated catalyst usage are the significant advantages of this research. Finally, an artificial neural network (ANN) is expanded to estimate the degradation efficiency of AB5 on the basis of the experimental results, which indicates the appropriate performance (R2 = 0.955).
Rahmani, Amir,Khataee, Alireza,Kaymak, Baris,Vahid, Behrouz,Fathinia, Mehrangiz,Dindarsafa, Mahsa
p. 81219 - 81230
(2016/09/09)

Protonation and proton-coupled electron transfer at S-ligated [4Fe-4S] clusters
Biological [Fe-S] clusters are increasingly recognized to undergo proton-coupled electron transfer (PCET), but the site of protonation, mechanism, and role for PCET remains largely unknown. Here we explore this reactivity with synthetic model clusters. Protonation of the arylthiolate-ligated [4Fe-4S] cluster [Fe4S4(SAr)4]2- (1, SAr=S-2,4-6-(iPr)3C6H2) leads to thiol dissociation, reversibly forming [Fe4S4(SAr)3L]1- (2) and ArSH (L=solvent, and/or conjugate base). Solutions of 2+ArSH react with the nitroxyl radical TEMPO to give [Fe4S4(SAr)4]1- (1ox) and TEMPOH. This reaction involves PCET coupled to thiolate association and may proceed via the unobserved protonated cluster [Fe4S4(SAr)3(HSAr)]1- (1-H). Similar reactions with this and related clusters proceed comparably. An understanding of the PCET thermochemistry of this cluster system has been developed, encompassing three different redox levels and two protonation states. Transfer target: S-Ligated [4Fe-4S] clusters undergo proton-coupled electron transfer involving the reassociation of a thiol ligand (see figure). An understanding of the proton-coupled electron-transfer (PCET) thermochemistry of this cluster system has been developed, encompassing three different redox levels and two protonation states.
Saouma, Caroline T.,Morris, Wesley D.,Darcy, Julia W.,Mayer, James M.
p. 9256 - 9260
(2015/06/16)

Preparation and catalytic performance of perfluorosulfonic acid-functionalized carbon nanotubes
Perfluorosulfonic acid-functionalized carbon nanotubes were prepared by liquid deposition of the perfluorosulfonic acid-polytetrafluoroethylene copolymer and characterized by N2 adsorption, scanning electron microscopy, transmission electron mi
Zhang, Mengxiao,Li, Cuican,Hua, Weiming,Yue, Yinghong,Gao, Zi
p. 1874 - 1882
(2015/09/28)

Enhanced activity over alkyl/aryl functionalized porous pillared-zirconium phosphates in liquid-phase reaction
A series of porous pillared-zirconium phosphates functionalized with methyl, ethyl, propyl and phenyl groups were prepared and characterized by SEM, 29Si MAS NMR, TG and N2 adsorption. Their total surface acidity and accessible one were measured by potentiometric titration of n-butylamine and liquid phase 2,6-di-tert-butyl-pyridine adsorption, respectively. The catalytic behaviors of these hybrid materials for alkylation of hydroquinone and esterification of lauric acid were compared. Not the total acid sites but the accessible ones play a crucial role in both reactions of alkylation and esterification. The accession for acid sites can be enhanced by the introduction of alkyl/aryl groups, due to the improved hydrophobicity of the surface.
Liu, Ke,Wang, Xueyan,Ding, Shengda,Li, Ying,Hua, Weiming,Yue, Yinghong,Gao, Zi
p. 84 - 89
(2013/11/06)

Sulfonic acid functionalized MCM-41 as solid acid catalyst for tert-butylation of hydroquinone enhanced by microwave heating
Covalently linked sulfonic acid (SO3H) modified MCM-41 mesoporous catalysts was prepared, characterized and its catalytic activity under microwave irradiation was evaluated. The NH2-MCM-41 was first prepared by anchoring (3-aminoprop
Ng, Eng-Poh,Mohd Subari, Siti Norbayu,Marie, Olivier,Mukti, Rino R.,Juan, Joon-Ching
p. 34 - 41
(2013/02/25)

An efficient reduction of quinones by formate-palladium/carbon system
Ammonium formate in presence of palladium-carbon is an efficient system for catalytic transfer hydrogenation of several functional groups under mild conditions. However, this system was not found effective for reduction of quinones to hydroquinones, although reduction could be effected with phosphinic acid, phosphinates or cyclohexene as donors. A reexamination of this reaction suggested that formates were good hydrogen donors in this reduction but the reaction was inhibited due to quinhydrone formation. A simple expedient of maintaining low concentration of quinone during catalytic transfer hydrogenation reduction gave excellent yields of the hydroquinone. Compared to formates, formic acid was found to be a poor hydrogen donor.
Pande, Poorn Prakash
experimental part
p. 2549 - 2553
(2010/11/05)

PRODUCTION OF A DISUBSTITUTED HYDROQUINONES
A process for the production of a disubstituted hydroquinone which comprises alkylating hydroquinone in the presence of a sulphonic acid condensation catalyst with an olefin or a substance which under the reaction conditions acts as a source thereof. The preferred olefin is 2-methyl-2-butene either alone or in admixture- with isomers thereof, and the preferred catalyst is methane sulphonic acid and the reaction product is 2,5-di-tert-amylhydroquinone. Only catalytic amounts of catalyst are required. The reaction product is worked-up by complete dissolution of the desired product and washing with an aqueous medium containing a pH buffering agent and a reducing agent.
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Page/Page column 12-13

(2008/06/13)

Mild cleavage of aryl mesylates: Methanesulfonate as potent protecting group for phenols
A mild protocol for the chemoselective deprotection of aryl methanesulfonates is described. The transformation can be conducted on highly functionalized substrates and renders the methanesulfonate a useful, previously underutilized protecting group for phenols.
Ritter, Tobias,Stanek, Kyrill,Larrosa, Igor,Carreira, Erick M.
p. 1513 - 1514
(2007/10/03)

Hydrogen-bonding effects on the properties of phenoxyl radicals. An EPR, kinetic, and computational study
The effect of 1,1,1,3,3,3-hexafluoropropan-2-ol (HFP) on the properties of phenoxyl radicals has been investigated. HFP produces large variations of the phenoxyl hyperfine splitting constants indicative of a large redistribution of electron spin density, which can be accounted for by the increased importance of the mesomeric structures with electric charge separation. The conformational rigidity of phenoxyl radicals with electron-releasing substituents is also greatly enhanced in the presence of HFP, as demonstrated by the 2 kcal/mol increase in the activation energy for the internal rotation of the p-OMe group in the p-methoxyphenoxyl radical. By using the EPR equilibration technique, we have found that in phenols the O-H bond dissociation enthalpy (BDE) is lowered in the presence of HFP because it preferentially stabilizes the phenoxyl radical. In phenols containing groups such as OR that are acceptors of H-bonds, the interaction between HFP and the substituent is stronger in the phenol than in the corresponding phenoxyl radical because the radical oxygen behaves as an electron-withdrawing group, which decreases the complexating ability of the substituent. In phenols containing OH or NH2 groups, EPR experiments performed in H-bond accepting solvents showed that the interaction between the solvent and the substituent is much stronger in the phenoxyl radical than in the parent phenol because of the electron-withdrawing effect of the radical oxygen, which makes more acidic, and therefore more available to give H-bonds, the OH or NH2 groups. These experimental results have been confirmed by DFT calculations. The effect of HFP solvent on the reactivity of phenols toward alkyl radicals has also been investigated. The results indicated that the decrease of BDE observed in the presence of HFP is not accompanied by a larger reactivity. The origin of this unexpected behavior has been shown by DFT computations. Finally, a remarkable increase in the persistency of the α-tocopheroxyl radical has been observed in the presence of HFP.
Lucarini, Marco,Mugnaini, Veronica,Pedulli, Gian Franco,Guerra, Maurizio
p. 8318 - 8329
(2007/10/03)

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)

SLIME REMOVER AND SLIME PREVENTING/REMOVING AGENT
A drainage slime remover capable of spreading a solution of a solid over slime generated wall surface portions, comprising a solid containing a microorganism growth retarding substance and a container which has a shape for permitting the installation thereof at the inlet or upper portion of a drain outlet and stores the solid characterized in that the container has drain flow-in holes having an opening capable of controlling a drain flow-in amount and provided in the upper surface or the upper side portion of the container and solution flow-out holes having an opening capable of controlling a flow-out amount of a solid solution and provided in the bottom or the lower side portion of the container or additionally in the side surface thereof, and a slime preventing/removing agent which can remove slime from portions such as kitchen sinks and bathroom drain outlets where slime is grown by metabolites such as miscellaneous germs and mildews and which can prevent the occurrence of slime safely and for an extended period of time.
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(2008/06/13)

Method for C-alkylating hydroxylated aromatic compounds
PCT No. PCT/FR96/01722 Sec. 371 Date Aug. 31, 1998 Sec. 102(e) Date Aug. 31, 1998 PCT Filed Oct. 31, 1996 PCT Pub. No. WO97/16402 PCT Pub. Date May 9, 1997A method for C-alkylating a hydroxylated aromatic compound having at least one hydrogen atom in the ortho or para position relative to the hydroxyl grouping, wherein the aromatic compound is exposed to a proton acid and a compound causing the formation of a carbo-cation in the presence of the acid, and the reaction is performed in the presence of a solvent consisting of a water-alcohol pair.
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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)

p-di-t-butoxybenzene
p-Di-t-butoxybenzene (1) [p-di-tert-butoxybenzene; benzene, 1,4-di-tert-butoxy-; 1,4-bis(1,1-dimethylethoxy)benzene; 1,4-benzenediol (or benzene-1,4-diol) di-tert-butyl ether; Chem. Abstr. number 15360-01-7] does not have the physical properties ascribed to it in the Dictionary of Organic Compounds, where it has been mistaken for 2,5-di-t-butylhydroquinone (4).
Carman, Raymond M.,Kanizaj, Nicholas,Taylor, Richard J.K.
p. 515 - 516
(2007/10/03)

Amorphous modification of 1,1',1"-nitrilo(tri-2-propyl-tris-[2,2'-ethylidene-bis(4,6-di-tert-butylphenyl] phosphite)
The new amorphous modification of 1,1',1"-nitrilo{tri-2-propyl-tris-[2,2'-ethylidene-bis(4,6-di-tert-butylphenyl)]phosphite } is obtained by cooling rapidly said compound from the melt to ambient temperature. This amorphous form is an effective process stabilizer for polyolefins, particularly polypropylene.
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(2008/06/13)

3,9-carbohydrate substituted 2,4,8,10-tetraoxa-3,9-diphosphaspiro(5.5)undecane phosphite stabilizers
Carbohydrate substituted phosphites of Formula I STR1 where A is a carbohydrate residue are effective stabilizers for polymers processed at elevated temperatures and subject to thermal or oxidative degradation.
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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)

Perfluoroalkyl substituted hydroxyphenylalkanoic ester antioxidants and stabilized compositions
Perfluoroalkyl substituted neopentyl alcohols can be reacted with substituted hydroxphenylalkanoic esters to form perfluoroalkyl containing hydroxyphenylalkanoic ester antioxidants. The perfluoroalkyl substituted hindered hydroxyphenyl alkanoates are stablizers which confer superior processing stability to polymers processed at elevated temperatures such as polypropylene, as well as protecting said polymers from thermal and oxidative degradation.
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(2008/06/13)

Carbohydrate substituted dibenzo(d,f)(1,3,2)dioxaphosphepin stabilizers
Carbohydrate substituted dibenzo[d,f][1,3,2]dioxaphosphepin compounds of formula I STR1 where A is a carbohydrate residue are effective stabilizers for polymers processed at elevated temperatures and subject to thermal or oxidative degradation.
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(2008/06/13)

Beta crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl) phosphite]
The beta crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl) phosphite] is obtained by crystallizing said compound from the melt at elevated temperatures. The beta crystalline form is an effective process stabilizer for polyolefins, particularly polypropylene.
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(2008/06/13)

Solid state redox chemistry of hydroquinones and quinones
Solid state ceric ammonium nitrate (CAN) oxidation of hydroquinones to the corresponding quinones, gives best results when operating with ultrasonic irradiation. Nitrogen dioxide plays a key role in these 'solid-solid' oxidations. The oxidation of hydroquinones to quinones can also be achieved in a unique 'solid-solid-solid' reaction, i.e., by using a limited amount of CAN in the presence of a full equivalent of a solid cooxidant such as KBrO3. Reduction of quinones with sodium dithionite in the solid state gives rise to the corresponding highly colored quinhydrones and, eventually, to hydroquinones.
Morey,Saa
p. 105 - 112
(2007/10/02)

Non-migrating 1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidine 1,3,5-triazine derivatives
1-Hydrocarbyloxy-2,2,6,6-tetramethylpiperidine derivatives of s-triazines having functional groups such as hydroxy, amino, carboxy, epoxy, isocyanate or the like present are capable of chemically bonding with polymer substrates having anhydride, epoxide, alkoxymethylmelamine or isocyanate moieties present. This chemical bonding prevents migration or loss of the stabilizer during subsequent processing or end-use application of the stabilized polymer.
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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-hydroxy-2,6-diaryl-4-piperidone ketals and polymer compositions stabilized therewith
1-Hydroxy-2,6-diaryl-4-piperidone ketal derivatives, such as the compound of formula I STR1 wherein Ar1 and Ar2 are each phenyl, R1 to R6 are all hydrogen, X1 and X2 are each --O-- and T is a direct bond, are novel compounds and are effective process stabilizers, such as polypropylene, for polymers processed at elevated tempertures providing both good melt flow stabilization and good resistance against discoloration during said processing.
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(2008/06/13)

N-Allyl/benzyl substituted phenylenediamine stabilizers
Compositions are described which comprise (a) a lubricant, subject to oxidative or thermal degradation, and (b) at least one compound of formula I wherein, R5, R6, R7 and R8 are independently hydrogen, alkenyl of 3 to 18 carbon atoms, aralkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one to three substituents selected from the group consisting of alkyl of 1 to 20 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms, -CN, -NO6, halogen, -ORψ, -NR?R?, -SR?, -COOR and -CONR54R55 where Rψ, R?, R?, R?, R , R54 and R55 are independently hydrogen, alkyl of 1 to 20 carbon atoms, alkenyl of 3 to 18 carbon atoms, aryl of 6 to 10 carbon atoms, cycloalkyl of 5 to 12 carbon atoms or aralkyl of 7 to 15 carbon atoms. Some of the compounds of formula one are novel.
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(2008/06/13)

Clathrate composition including essential oils and method of using same
A composition for killing harmful organisms, which contains a clathrate compound composed of one or more natural essential oils and/or derivatives thereof selected from the group consisting of the following substances (1) to (22) and a polymolecular host compound capable of including the natural essential oils and/or derivatives thereof: (1) hinoki oil; (2) 1,8-cineole; (3) l-α-terpineole; l-carbone; (5) l-menthone; (6) d-pulegone; (7) citronellal; (8) linelool oxide; (9) d,l-citronellol; (10) 3,3,5-trimethylcyclohexanol; (11) l-perillaldehyde; (12) l-carveol; (13) myrtenal; (14) peppermint oil; (15) eucalyptus oil; (16) cinnamic aldehyde; (17) α-bromo-cinnamic aldehyde; (18) salicylaldehyde; (19) benzaldehyde; (20) paraphenyl-propionaldehyde; (21) paratolualdehyde; and (22) l-menthol.
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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)

Substituted 2,3-dihydroperimidine stabilizers
N-Allyl and N-methylene-thio substituted 2,3-dihydroperimidine compounds are very effective antioxidant stabilizers for organic material subject to oxidative or thermal degradation, particularly for lubricant compositions.
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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)

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)

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)

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)

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)

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)

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)

Reactivity of some Quinones with Alkylaluminium Compounds
The reactions of 2-methyl-1,4-naphthoquinone with triethylaluminium and 2,5-di-t-butyl-1,4-benzoquinone with triisobutylaluminium were studied.In each of these reactions three different products were obtained and characterized by n.m.r. and i.r.U.V. spectrophotometry showed that 2-methyl-1,4-naphthoquinone behaves as a weak base and the ionization constants pK1 = -0.922 and pK2 = -4.065 were reported in aqueous HClO4.This is a useful information for elucidating the mechanism of the first reaction studied, based on the different basicity of the carbonyl groups.
Leal, J. M.,Arcos, J.,Garcia, B.
p. 887 - 896
(2007/10/02)

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)

Silica Gel as an Effective Catalyst for the Alkylation of Phenols and Some Heterocyclic Compounds
In the presence of silica gel, the reaction of phenol with t-BuBr was examined under a variety of conditions and it was found that silica gel is an effective catalyst for the alkylation.As a result of this work 2-tert-butyl-, 2,6-di-tert-butyl-, and 2,4,6-tri-tert-butylphenols, all of which are hard to obtain directly by the Friedel-Crafts process, could be prepared easily by this one-step reaction.Several other alkyl halides were also used in this reaction.The alkylations of some heterocyclic aromatic compounds which cannot be alkylated by the conventional Friedel-Crafts method were also succesfully performed by this reaction.
Kamitori, Yasuhiro,Hojo, Masaru,Masuda, Ryoichi,Izumi, Tatsuo,Tsukamoto, Shuichi
p. 4161 - 4165
(2007/10/02)

Allylation of Quinones with Allyltin Reagents
Lewis acid (BF3) catalyzed allylation of quinones with allyl- (2a), 2-methyl-2-propenyl- (2b), trans-2-butenyl- (2c,d), 3-methyl-2-butenyl- (2e,f), and trans-cinnamyltrialkyltin (2g) gives the corresponding allylhydroquinones with high regioselectivity.Vitamin K2(5) (7) and coenzyme Q1 (9) were prepared in yields of 78 and 75percent, respectively.These reactions appear to proceed through allylquinol intermediates which undergo rearrangement under the influence of BF3.The success of this synthesis of vitamin K2(5) and coenzyme Q1 depends on the fact that the reaction of 3-methyl-2-butenyltin with quinones occurs at the α carbon of the allylic system.
Naruta, Yoshinori
p. 3774 - 3783
(2007/10/02)