Abstract: The present invention provides in a particular embodiment an improvement in the process for producing phenol by the acid-catalyzed cleavage of cumene hydroperoxide (CHP). The reactant stream fed to the cleavage reactor also includes the contaminant by-product dimethyl benzyl alcohol (DMBA) formed during the direct oxidation of cumene to CHP. This contaminant DMBA further reacts in the cleavage reactor to reduce the yield of phenol and produce undesirable and unreclaimable by-products. The improvement provided herein comprises performing the cleavage reaction at a reduced residence time of generally from one-half to five minutes, whereby the formation of .alpha.-methyl styrene from DMBA is promoted and the formation of the undesirable and unreclaimable by-products is reduced; .alpha.-methyl styrene is not only a useful by-product, but can be recycled and hydrogenated to the cumene starting material.

Abstract: A process for the reduction of methylbenzofuran (MBF) impurities in phenol obtained from the decomposition product of cumene hydroperoxide requires treating the phenol to reduce the level of acetol, contacting the phenol containing a low level of acetol with an acid resin at sufficient temperature and residence time to reduce the level of MBF by conversion to higher boiling compounds, then distilling the phenol to separate phenol from higher boiling compounds. The phenol may be treated in known ways, such as by treatment with an amine, to reduce the level of acetol. The phenol containing a low level of acetol is contacted with a strong acid resin to reduce the level MBF.

Abstract: The present invention provides in a particular embodiment an improvement in the process for producing phenol by the acid-catalyzed cleavage of cumene hydroperoxide (CHP). The reactant stream fed to the cleavage reactor also includes the contaminant by-product dimethyl benzyl alcohol (DMBA) formed during the direct oxidation of cumene to CHP. This contaminant DMBA further reacts in the cleavage reactor to reduce the yield of phenol and produce undesirable and unreclaimable by-products. The improvement provided herein comprises performing the cleavage reaction at a reduced residence time of generally from one-half to five minutes, whereby the formation of .alpha.-methyl styrene from DMBA is promoted and the formation of the undesirable and unreclaimable by-products is reduced; .alpha.-methyl styrene is not only a useful by-product, but can be recycled and hydrogenated to the cumene starting material.

Abstract: The present invention relates to a process for the preparation of aromatic polyhydroxy compounds, by reacting an aromatic hydroxyaldehyde with hydrogen peroxide, with or without the addition of a base, in the presence of a nitrile R--CN, in which R is an alkyl radical having 1 to 4 carbon atoms or a phenyl radical, which is unsubstituted or substituted by one or more alkyl groups.

Abstract: The phenols/phenol ethers are hydroxylated by reaction with hydrogen peroxide, in the presence of a catalytically effective amount of (a) at least one alkali metal or alkaline earth metal salt of a protonic acid having a pKa in water of less than -0.1 and (b) a free protonic acid.

Abstract: The phenols and phenol ethers, e.g., phenol itself, are effectively hydroxylated by reacting hydrogen peroxide therewith, in the presence of a catalytically effective amount of titanium dioxide.

Abstract: A process for producing dihydric phenols is disclosed. The process comprises reacting a phenol with a ketone peroxide or a combination of a ketone and hydrogen peroxide in the presence of a compound having at least one P-S bond. Dihydric phenols can be produced in high yield without requiring neutralization after the reaction.

Abstract: There is provided a novel organic hydroperoxide, 3-(2-hydroperoxy-2-propyl)phenol. The hydroperoxide is produced by oxidizing 3-(2-hydroxy-2-propyl)phenol or m-isopropenylphenol with hydrogen peroxide in the presence of an acid catalyst.There is further provided a method of producing resorcinol which comprises decomposing the 3-(2-hydroperoxy-2-propyl)phenol in the presence of an acid catalyst.

Abstract: Phenol is produced in a recycle manner by (a) reacting benzene with propylene to synthesize cumene, (b) oxidizing the cumene of step (a) into cumene hydroperoxide, (c) acid cleaving cumene hydroperoxide into phenol and acetone, (d) hydrogenating the acetone of step (c) into isopropanol, (e) dehydrating the isopropanol of step (d) into propylene, and (f) recycling the propylene of step (e) to step (a). It is also possible to take propylene from step (e). The acetone by-product produced upon preparation of phenol is converted into propylene which is useful by itself for any other uses or recycled to the phenol producing process.

Abstract: In a first form, a process is provided for preparing phenol by converting acetone by-produced by the cumene process into isopropanol, and alkylating benzene with the isopropanol and optional propylene, thereby forming phenol without acetone by-product. And cumene is prepared by alkylating benzene in the presence of a zeolite catalyst using isopropanol or a mixture of isopropanol and propylene as an alkylating agent. Further provided is the continuous alkylation of benzene with isopropanol wherein a reaction mixture is divided into first and second portions, with the first portion being recycled to the reactor and the second portion being taken out as a reaction product.

Abstract: The acetone peroxides contained in oxidate reaction mixtures thereof, e.g., those resulting from phenol syntheses, are hazardous and explosive compounds when present in the solid state, and are consumed by (a) adjusting the pH of such reaction mixture to a value ranging from 4 to 8; (b) adding a copper compound to such reaction mixture; and (c) maintaining such reaction mixture at a temperature ranging from 50.degree. C. to 150.degree. C.

Abstract: A process for the production of dihydric phenoles by oxidizing diisopropylbenzenes, which comprises oxidizing diisopropylbenzenes with molecular oxygen to obtain a reaction product mixture (A) containing at least diisopropylbenzene dihydroperoxide (DHP) and diisopropylbenzene monocarbinol monohydroperoxide (HHP), supply said product mixture (A) in a form of oily phase as a solution in an aromatic hydrocarbon solvent to an agitation reactor, supplying thereto at the same time, as an aqueous phase, hydrogen peroxide at a feed rate of 1-5 moles per mole of HHP contained in the product mixture and an acid catalyst in an amount sufficient to reach a concentration in the aqueous phase of 10-40% by weight, the concentration of hydrogen peroxide in the aqueous phase being maintained at a value of at least 20% by weight and the weight ratio of the oily phase/aqueous phase being at least 10, causing oxidization of the HHP into DHP by hydrogen peroxide while maintaining the reaction temperature at 30.degree.-60.degree.

Abstract: Process for the preparation of alkyl-substituted phenols or naphthols by oxidizing the corresponding dialkylbenzenes or dialkylnaphthalenes, respectively, at elevated temperatures of, for example, 70.degree. to 130.degree. C. by means of oxygen or oxygen donors, in the absence of solvents and in the presence of an alkali metal salt or alkaline earth metal salt of an organic carboxylic acid having 5 to 14 carbon atoms, to give the corresponding 2,6-dialkylnaphthalene-or 1,4-dialkylphenyl monohydroperoxides and subsequently hydrolysing the latter in a customary manner.The process results in pure, easily isolatable products in a good yield. The products of the process according to the invention are valuable precursors and intermediates for, inter alia, dyes, plastics or pharmaceuticals.

Abstract: A method is disclosed for the synthesis of phenol and acetone by decomposition over a heterogeneous catalyst from the group consisting of a heteropoly acid on an inert support or an ion exchange resin with a sulfonic acid functionality. The method allows for quantitative conversions with yields of up to >99 mole % or better.

Abstract: A method is disclosed for the synthesis of phenol and acetone by decomposition over a heterogeneous catalyst comprising a fluorine-containing acidic compound on an inert support. The method allows for quantitative conversions with yields of up to >99 mole %.

Abstract: A method is disclosed for the synthesis of phenol and acetone by acid-catalyzed decomposition over a catalyst comprising an acidic smectite clay, particularly an acidic montmorillonite silica-alumina clay. The method allows for quantitative conversions with yields of up to 98% mole or better. Further the method is capable of operating efficiently at high LHSVs.

Abstract: A process for the preparation of resorcinol from diisopropylbenzene includes the steps of oxidizing m-diisopropylbenzene under anhydrous, non-alkaline conditions with oxygen, extracting m-diisopropylbenzene dihydroperoxide and m-diisopropylbenzene hydroxyhydroperoxide with dilute sodium hydroxide, re-extracting with an organic solvent, converting m-diisopropylbenzene hydroxyhydroperoxide to m-diisopropylbenzene dihydroperoxide with hydrogen peroxide, drying the product, decomposing the m-diisopropylbenzene dihydroperoxide in the presence of a catalyst selected from the group consisting of boron trifluoride, ferric chloride and stannic chloride to coproduce resorcinol and actone, and purifying the resorcinol.

Abstract: An improvement in a process for the preparation of resorcinol which includes the steps of treating an extract of selected oxidation products of diisopropylbenzene with hydrogen peroxide to convert m-HHP to m-DHP, drying the treated extract and thereafter, decomposing the m-DHP in the presence of an effective amount, preferably within the range of about 10 to 50 ppm, of a catalyst selected from the group consisting of boron trifluoride, ferric chloride and stannic chloride.

Abstract: An improvement in the preparation of resorcinol includes the decomposition of m-diisopropylbenzene dihydroperoxide (m-DHP) to resorcinol and acetone in the presence of an effective amount of a catalyst selected from the group consisting of boron trifluoride, ferric chloride and stannic chloride. Minute quantities of the catalyst, preferably 10 to 50 ppm, are effective to increase the yields of resorcinol.

Abstract: A procedure for producing hydroquinone from a hydrocarbon mixture obtained as a by-product when producing cumene, by selectively oxidizing tertiary alkylaromatics to form hydroperoxides, by separating the dihydroperoxide of p-diisopropylbenzene from the oxidation product by selective crystallization through cooling, and by decomposing the dihydroperoxide of p-diisopropylbenzene with the aid of an acid catalyst to form the hydroquinone.

Abstract: A process for replacing an aromatic carbon-thallium bond with a carbon-oxygen bond. The process is particularly suitable for producing specific aromatic isomers by thallating an aromatic compound and replacing the thallium with a carboxylate group which can be further hydrolyzed if desired to form an aromatic hydroxyl compound.

Abstract: An improved process for the manufacture of a dihydric phenol such as hydroquinone wherein a dialkylbenzene is oxidized to a dihydroperoxide, the dihydroperoxide being extracted from the oxidate by a caustic solution, leaving an organic phase for recycle to the oxidizer, the improvement comprising decreasing the caustic concentration in the recycle organic phase and increasing the dihydroperoxide concentration of the recycle phase by washing the organic phase from the caustic extract with an aqueous phase removed from the oxidizer, separating the organic phase from the aqueous phase and subsequently introducing the organic phase to the oxidizer.

Abstract: The known nuclear hydroxylation of substituted phenols or phenol ethers with organic solutions of hydrogen peroxide in the presence of a catalyst is carried out in improved manner by employing both (1) a special, practically water free solution of hydrogen peroxide in an organic solvent which forms an azeotrope with water, which azeotrope boils below the boiling point of hydrogen peroxide, and (2) sulfur dioxide as a catalyst. Through this, the nuclear hydroxylation is substantially simpler than previously; difficult separations, e.g., from water-phenol, or the separation and recovery of the catalyst are eliminated. Besides, the yields are increased.

Abstract: There is disclosed an improved process for oxidizing a hydrocarbon to produce a reaction mixture containing the corresponding organic hydroperoxide of said hydrocarbon and decomposing said hydroperoxide to provide a mixture containing reaction products of said decomposition reaction, including alcohol and/or ketone products, comprising effecting said oxidation and/or decomposition in the presence of a catalytic quantity of a catalyst system comprised of ruthenium and chromium.

Abstract: Phenol and acetone are produced by the cleavage of cumene hydroperoxide in the presence of a solid heterogeneous catalyst with acidic activity comprising an intermediate pore size zeolite such as ZSM-5.

Abstract: Phenol and acetone are produced by the cleavage of cumene hydroperoxide in the presence of a solid heterogeneous catalyst with acidic activity comprising zeolite beta.

Abstract: A process for producing phloroglucin important as an intermediate compound of medicine, sensitizer and the like which comprises reacting an oxidation product containing at least one carbinol compound of carbinol dihydroperoxide, dicarbinol hydroperoxide and tricarbinol obtained by oxidation of 1,3,5-triisopropylbenzene, with hydrogen peroxide in a heterogeneous system in the presence of an acid catalyst and an organic solvent inert to the hydrogen peroxide and capable of dissolving the oxidation product, and decomposing the reaction product with an acid.

Abstract: An improved method for the acid-catalyzed rearrangement of a dialkylbenzene dihydroperoxide to a dihydric phenol which eliminates the formation of an emulsion during the subsequent separation and recovery of the dihydric phenol in a process which utilizes water, the method comprising the addition of the acid as a solution in a water soluble organic solvent, preferably a ketone, which is non-reactive with the acid.

Abstract: In a method for producing phloroglucin by a decomposition of 1,3,5-triisopropylbenzene trihydroperoxide (hereinafter referred to as THPO), a method for producing phloroglucin wherein an acid catalytic decomposition is carried out under the condition that:(1) at least one member selected from the group consisting of perchloric acid, sulfuric anhydride and boron trifluoride be used as a catalyst,(2) the amount of the catalyst above in the reaction solution be 1 to 100 ppm,(3) the water content in the reaction solution be not more than 2% by weight, and(4) the total amount of the carbinol group of carbinols (having a structure in which part or all of the three hydroperoxy groups of THPO have been replaced by hydroxyl groups) contaminating the raw material for reaction be not more than 1/5 equivalent based on THPO.The phloroglucin is useful as a starting material of medicines and photosensitizers.

Abstract: A method for purifying phloroglucin wherein crude phloroglucin obtained by an acid-decomposition of 1,3,5-triisopropylbenzene trihydroperoxide in the presence of a solvent and removal of the formed acetone and the solvent by evaporation, is extraction-treated within a pH range of 7.5 to 12 in the coexistence of an aqueous alkali liquor of 4 to 25 times by weight based on the crude phloroglucin and an organic solvent of 0.05 to 6 times by weight based on said aqueous alkali liquor selected from ketones and esters which are separable from the aqueous alkali liquor, and after acidifying the separated aqueous alkali extract, the deposited crystal is recrystalized.The phloroglucin is useful as a starting material of medicines and photosensitizers.

Abstract: Process for hydroxylating alkylphenols in which the carbon atoms of the alkyl group bonded to the aromatic nucleus has at least one hydrogen atom bonded thereto and the phenolic ethers thereof, at the meta position relative to the phenol or ether function, by reacting the phenol compound with an aqueous hydrogen peroxide solution in the presence of a liquid superacid at low temperature.

Abstract: Process for the isomerization of ortho- and para-bromophenols or the ethers thereof into corresponding meta-brominated derivatives by isomerizing ortho- and para-bromophenols in the corresponding ethers in the presence of a liquid superacid at a temperature in the region of ambient temperature.

Abstract: High quality hydroquinone is produced from p-diisopropylbenzene dihydroperoxide at a high yield according to the disclosed process. The p-diisopropylbenzene dihydroperoxide is decomposed in the presence of an acid catalyst and the concentration of the hydroperoxide is maintained in the range of 0.1 to 1% by weight; the remaining hydroperoxide in the decomposition step is further subjected to an acid decomposition prior to the recovery of the formed hydroquinone product.

Abstract: A process for recovery of resorcinol from an aqueous resorcinol solution containing hydroquinone which comprises oxidizing an aqueous resorcinol solution containing about 10 to about 60% by weight of resorcinol and up to about 1% by weight of hydroquinone with molecular oxygen at conditions of pH 6.5 to 9.5, followed by recovering resorcinol from the resultant oxidation product.

Abstract: Resorcinol is prepared in high yield and purity by an improved process through superacid (such as perfluorinated alkanesulfonic acids of one to eighteen carbon atoms or polymeric perfluorinated resinsulfonic acids, such as acidified Nafion-H, catalyzed cleavage-rearrangement reaction of meta-bis(2-hydroperoxy-2-propyl)-benzene (meta-diisopropylbenzene dihydroperoxide). Part of the process is the preparation of needed meta-diisopropylbenzene in high purity (98-100%) substantially free of other isomers by treating any mixture of diisopropylbenzenes with an excess of anhydrous hydrogen fluoride or a perfluorinated alkanesulfonic acid of one to six carbon atoms and a Lewis acid fluoride, or by alkylating (transalkylating) cumene with a propyl alkylating agent in the aforementioned superacid systems.

Abstract: In a process for producing resorcinol, which comprises cleaving m-diisopropylbenzene dihydroperoxide in the presence of a water-soluble acid catalyst in a mixed solvent consisting of an aromatic hydrocarbon and acetone, treating the resulting acid cleavage product containing resorcinol with an aqueous solution of a neutral salt under acidic conditions, separating the solvent layer containing resorcinol from the aqueous layer, and recovering resorcinol from the separated solvent layer; the improvement wherein (i) the acid cleavage is carried out while maintaining the weight ratio of the aromatic hydrocarbon to acetone at less than 0.6, and at a time after formation of the acid cleavage product but before the treatment of the cleavage product with the aqueous solution of the neutral salt, the amount of the aromatic hydrocarbon in the mixed solvent is adjusted so that the weight ratio of the aromatic hydrocarbon to acetone in the product is from 0.6 to 1.

Abstract: Resorcinol is prepared by an improved process through superacid (such as perfluorinated alkanesulfonic acids of one to eighteen carbon atoms or polymeric perfluorinated resinsulfonic acids, such as Nafion-H catalyzed cleavage-rearrangement reaction of meta-isopropylphenol hydroperoxide in the form of its protected ether or ester derivatives, including readily cleavable and reusable trimethylsilyl and trifluoromethanesulfonyl derivates. Part of the process is the preparation of needed meta-isopropylphenol in high purity free of other isomers by treating any mixture of isopropylphenol isomers in an excess of anhydrous hydrogen fluoride or a perfluorinated alkanesulfonic acid of one to six carbon atoms and a Lewis acid fluoride or by alkylating (transalkylating) phenol with a propyl alkylating agent in the presence of the aforementioned superacid systems.

Abstract: A process for the co-production of 2-alkanones having at least five carbon atoms and phenol or a substituted phenol. In the first step, benzene or a substituted benzene is alkylated with an alkyl moiety of at least five carbon atoms to selectively produce the 2-arylalkane isomer. Subsequent oxidation to the hydroperoxide and acid cleavage thereof yields the desired product. The alkylation step is carried out in the presence of a novel class of selective crystalline zeolite materials having pore openings with a major dimension of six to seven angstroms.

Abstract: A process is disclosed for converting p-isopropenylphenol and derivatives thereof and, more particularly, oligomers of p-isopropenylphenol and derivatives thereof, to hydroquinone via monomeric intermediates [e.g. p-(2-haloisopropyl)phenol in the case of p-isopropenylphenol and oligomers thereof]. The process involves reacting the starting materials with a hydrogen halide (e.g. gaseous hydrogen chloride) in the presence of an organic solvent and subjecting the product so obtained to oxidation with hydrogen peroxide or an organic hydroperoxide.

Abstract: In a process for producing a phenolic compound which comprises treating an aralkyl hydroperoxide with a mineral acid to cleave it to phenolic compound and a ketone, neutralizing or removing the mineral acid, feeding the resulting acid cleavage mixture containing the salt to a distillation column, distilling it therein to separate it into an overhead fraction consisting mainly of the ketone and a bottom fraction consisting mainly of the phenolic compound, and recovering the phenolic compound from the bottom fraction; the improvement which comprises withdrawing a liquid layer from a site of feeding the acid cleavage mixture in the distillation column or from a site below it but above the bottom of the distillation column, subjecting the liquid layer to an oil-water separating means, recycling the separated oil layer to a site below said site of withdrawal, optionally feeding a hydrocarbon having a lower boiling point than the phenolic compound but a higher boiling point than the keton and/or water to the distil

Abstract: Exothermic hydroperoxide decomposition reactions catalyzed by solid polymeric acid catalysts are controlled by contacting the reactants with a thin film of the acid catalyst supported on the surface of an impermeable heat exchanger element and contacting the opposite side of the heat exchanger element with a heat transfer fluid.

Abstract: Cumene hydroperoxide is decomposed to phenol and acetone by mixing it with acetone and a catalyst, flowing it without substantial back mixing through a reactor and controlling the reaction temperature by evaporating acetone and thus reducing the acetone concentration of the mixture in the course of the reaction.

Abstract: In a method for recovering resorcinol by thermally cracking high-boiling by-products formed by the acid-cleavage of m-diisopropylbenzene dihydroperoxide in the presence of at least one ammonium compound selected from the group consisting of ammonium sulfate and ammonium bisulfate at a temperature of about 170.degree. C. to about 350.degree. C. under reduced pressure, the improvement wherein said thermal cracking is carried out at a pressure of less than 50 mmHg gauge in the absence of any inert gas supplied.

Abstract: A process for preparing resorcinol in improved yields while avoiding the formation of reactive by-products which comprises(1) a first step of pre-treating an oxidation product of m-diisopropylbenzene composed of m-diisopropylbenzene dihydroperoxide and by-product m-substituted carbinol hydroperoxide and/or dicarbinol with hydrogen peroxide in the presence of an acid catalyst in a heterogeneous system of an aqueous aromatic hydrocarbon solvent under conditions which do not substantially cause the acid cleavage, the pretreatment being performed while removing by-product water as an azeotrope with the aromatic hydrocarbon in the treating system, and(2) a second step of acid-cleaving the pre-treated reaction product in the substantial absence of hydrogen peroxide.

Abstract: In the process for obtaining a concentrate of resorcin by acid-decomposing m-diisopropylbenzene hydroperoxide in an inert solvent in the presence of an acidic solid catalyst and distilling off acetone and the inert solvent from the resulting acid-decomposition reaction mixture, if water is added to this reaction mixture in an amount of 20 to 70% by weight based on resorcin and the reaction mixture is then subjected to distillation, resorcin can be obtained at a high recovery yield.

Abstract: The invention relates to a process in which an aromatic hydroperoxide of formula: ##STR1## wherein independently R.sub.1 is methyl or ethyl, R.sub.2 is hydrogen, methyl or ethyl, or where R.sub.1 and R.sub.2 together form an alicyclic ring of 5 or 6 carbon atoms, R.sub.3 is hydrogen or alkyl and R.sub.4 and R.sub.5 are hydrogen, alkyl or together form an automatic ring, n is 0, 1 or 2 and n.sup.1 is 1 or 2, is converted to a phenol and a carbonyl compound in a catalyzed cleavage decomposition reaction. In particular cumene hydroperoxide is converted to phenol and acetone. Instead of removing the decomposition products from the reactor in the liquid phase and dissipating the reaction heat as in prior art processes the heat is used to remove the phenol and the carbonyl compound in the vapor phase leaving a liquid residue of higher-boiling compounds and catalyst in the case where a liquid cleavage catalyst is employed.

Abstract: Benzene or alkylbenzene (e.g. toluene) is alkylated with propylene to produce diisopropylbenzenes or isopropylalkylbenzenes, which in turn are selectively cracked to remove the 1,4-isomer. The resultant product, containing a high level of the 1,3-isomer, is then oxidized to 1,3-dihydroxybenzene or 3-alkylphenol (e.g. 3-methylphenyl) in significant yield.

Abstract: A process for the preparation of resorcin comprising decomposing meta-diisopropylbenzene dihydroperoxide in the presence of a synthetic silica-alumina catalyst, wherein the concentration of water in the reaction system is maintained at 0.3 to 1.0% by weight, is disclosed.

Abstract: Dihydric phenols produced by rearrangement of p-dialkylbenzene hydroperoxides are recovered from the rearrangement effluent by distilling byproduct ketone in a distillation tower from a mixture of the rearrangement effluent with benzene and dihydric phenol-containing aqueous feed and extracting impurities and aromatic byproducts with benzene. Benzene containing dissolved impurities and aromatic byproducts, and water containing the dihydric phenol are removed from the bottom of the distillation tower and separated in an extractor column, the dihydric phenol is recovered from its aqueous solution by crystallization and the mother liquor from the crystallization step is recycled to the distillation tower.

Abstract: A continuous process for cleaving aralkyl hydroperoxides in acid media to yield phenols and carbonyl compounds in a reactor arranged and operated to limit the total residence time to less than the time required to form discoloration products.