Abstract: A process for preparing an alkylated hydroxyl aromatic compound comprising reacting (a) a hydroxyl aromatic compound (I), having the following structure; wherein n 1, 2 or 3; m is 0, 1, 2, or 3 and R1 is Hydrogen or hydrocarbyl group; and (b) at least one ?-branched primary alcohol component in the presence of an alkylating catalyst thereby producing an alkylated hydroxyl aromatic compound.

Abstract: The invention relates to the preparation of alkylated phenols. More specifically, the invention relates to an improved process for the manufacture of 2-secondary-alkyl-4,5-di-normal-alkylphenols.

Abstract: An alkylated hydroxyaromatic compound prepared by reacting at least one hydroxyaromatic compound with a branched olefinic oligomer having from about 20 to about 80 carbon atoms in the presence of a acid catalyst. The alkylated hydroxyaromatic compound has been determined to be substantially free of endocrine disruptive chemicals when the effects were quantified on pubertal development and thyroid function in the intact juvenile female rat.

Abstract: Catalyst comprising a combination of oxidized metals and processes for cleaving phenylalkyl hydroperoxides in the presence of the catalyst.

Abstract: Paraffin-containing liquid pour point depressants comprising the reaction product of a hydrocarbyl-substituted phenol and an aldehyde wherein: the olefin used in the preparation of the hydrocarbyl-substituted phenol has a high vinylidene content; the reaction between the hydrocarbyl-substituted phenol and the aldehyde is acid or base catalyzed; and/or the reaction further comprises phenol, are particularly useful for treating crude oils which have an initial pour point of 4° C. or higher, decreasing the fluid's pour point and improving the fluid's low temperature handling properties.

Abstract: The present invention relates to novel processes for the manufacture of chroman derivatives such as ?-tocopherol (TCP) and alkanoates thereof, especially ?-tocopheryl acetate (TCPA), whereby at least one step of the processes is carried out in the presence of a Lewis acid or a mixture of a Lewis acid with a Bronsted acid as the catalyst under pressure, preferably at an absolute pressure of at least 1.1 bar. As starting materials for the manufacture of TCP and its alkanoates either a mixture of 2,3,5-trimethylhydroquinone (TMHQ) or 2,3,6-trimethylhydroquinone-1-alkanoate (TMHQA) and a compound selected from the group consisting of phytol (PH), isophytol (IP) and (iso)phytol derivatives or 2-phytyl-3,5,6-trimethyl-hydroquinone (PTMHQ)/3-phytyl-2,5,6-trimethylhydroquinone-1-alkanoate (PTMHQA) and/or an isomer thereof are used. Suitable Lewis acids are indium(III) salts and scandium(III) salts. Suitable acid mixtures are iron/iron(II) chloride/hydrogen chloride and zinc(II) chloride/hydrogen chloride.

Abstract: Alkoxylated alkylphenols which have at least one long-chain alkyl radical having at least one tertiary or quaternary carbon atom are prepared and are used as fuel or lubricant additives in fuel and lubricant compositions.

Abstract: We describe a process for the preparation of polyurethane polyol from CARDANOL 3-(8pentadecenyl)phenol, derived from cashew nut shell liquid (CNSL), a renewable resource material. The polyol is made by oxidation with peroxy acid generated in situ to give epoxidised CARDANOL 3-(8-pentadecenyl)phenol and the epoxy derivative is converted to the polyol in the presence of the organic acid. The cardanol-based polyol may be reacted with isocyanate to form polyurethane. Alternatively blowing agents are included with the cardanol-based polyol before it is reacted with the isocyanate. These polyols are especially suitable for making rigid foams of very low density and high compressive strength.

Abstract: Polyisobutenylphenols are prepared by alkylating an aromatic hydroxy compound with substantially monoethylenically unsaturated and substantially homopolymeric polyisobutenes in the presence of a Lewis acid alkylation catalyst by a process in which the polyisobutenes have a ? double bond content of at least 35 mol %.

Abstract: Polyisobutenylphenols are prepared by alkylating an aromatic hydroxy compound with substantially monoethylenically unsaturated and substantially homopolymeric polyisobutenes in the presence of a Lewis acid alkylation catalyst by a process in which an ether is additionally used as a cocatalyst, the ether having a molecular weight of at least 102 g/mol in the case of BF3 as the Lewis acid.

Abstract: An alkylated hydroxyl-containing aromatic compound is produced by isomerizing a normal alpha-olefin having from about 16 to about 30 carbon atoms in the presence of a first solid, acidic catalyst capable of inducing both olefin isomerization and skeletal isomerization to produce a mixture of isomerized olefin, then alkylating an hydroxyl-containing aromatic compound with the mixture of isomerized olefins in the presence of a second solid, acidic catalyst. The first solid, acidic catalyst can be SM-3, MAPO-11, SAPO-11, SSZ-32, ZSM-23, MAPO-39, SAPO-39, ZSM-22, SSZ-20, ZSM-35, SUZ-4, NU-23, NU-87, natural ferrierite or synthetic ferrierite. The second solid, acidic catalyst can be a sulfonic acid anionic ion exchange resin catalyst or an acidic clay.

Abstract: A catalyst composition comprising trifluoromethanesulfonic acid (also referred to as triflic acid) and a sufficient quantity of a substance (also referred to as a retarder) to decrease but not eliminate the catalytic activity of the acid is disclosed. Also disclosed, is a method and composition for condensing a hydroxyaryl with a diene by use of the catalyst composition. The method is capable of producing condensates having: a mole ratio of 1 mole of the diene to one mole of the hydroxyaryl; one mole of diene to two moles of the hydroxyaryl as well as higher molecular weight products such as resins by changes in temperature, time of reaction, type and quantity of retarder and other variables.

Abstract: A 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.

Abstract: Allylic styrene ether compounds of the formula: ##STR1## where R.sup.1 is an optionally substituted allylic or propargyl hydrocarbon group, and R.sup.2, R.sup.3, and R.sup.4 are independently H, C.sub.1-6 hydrocarbon or C.sub.1-6 hydrocarbonoxy groups, are prepared in a single pot reaction from relatively low cost materials. The method includes the steps of reacting a 4-acyloxystyrene of the formula ##STR2## where R is an acyl group, with at least one mole of a base which can readily saponify or hydrolyze the phenolic ester bond per mole of acyloxystyrene, and then adding to the reaction mixture an alloylating agent of the formula R.sup.1 X, where R.sup.1 is as previously defined and X is chloride, bromide, iodide, a sulfonic ester or a hydrocarbon sulfate group, to form said allylic styrene ether compound. The method may be employed to prepare mono-styryl functional compounds or di-styryl functional compounds such as 1,4-bis(4'-vinylphenoxy)but-2-ene.

Abstract: The present invention is directed to oil-soluble lubricating oil additives comprising borated Mannich Base condensates of an alkyl substituted hydroxy aromatic compound with formaldehyde and an amine, wherein the alkyl-moiety of the aromatic compounds is derived from at least one ethylene alpha-olefin copolymer of 300 to 20,000 number average molecular weight, wherein at least about 30% of the polymer's chains contain terminal ethenylidene unsaturation. The borated Mannich Base condensates of this invention are useful as dispersants.

Abstract: The present invention is directed to oil-soluble lubricating oil additives comprising Mannich Base condensates of an alkyl substituted hydroxy aromatic compound with formaldehyde and an amine, wherein the alkyl-moiety of the aromatic compounds is derived from at least one ethylene alpha-olefin copolymer of 300 to 20,000 number average molecular weight, wherein at least about 30% of the polymer's chains contain terminal ethenylidene unsaturation. The Mannich Base condensates of this invention are useful as dispersants.

Abstract: A process for the preparation of a polyisobutyl hydroxyaromatic compound which comprises alkylating a hydroxyaromatic compound in the presence of an acidic alkylation catalyst with a polyisobutene having a number average molecular weight in the range of about 300 to 5,000 and wherein the polyisobutene contains at least about 70% of a methylvinylidene isomer.

Abstract: Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene to about the mid point of the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.

Abstract: A process for alkylating an aromatic polyol, such as catechol, with an alpha olefin oligomer of alpha olefins having from about 8 to 14 carbon atoms or mixtures thereof using an organic sulfonic acid catalyst which is soluble under the alkylation reaction conditions. The liquid alkyl aromatic polyol product is useful as a lubricating oil additive or lubricating oil base stock.

Abstract: The invention relates to producing ortho isopropyl phenol catalytically by contacting phenol with isopropanol or propylene, at a temperature of from about 200.degree. C. to about 300.degree. C., with ZSM-12 and zeolite Beta; and recovering ortho isopropyl phenol.

Abstract: Disclosed is a one step method for synthesis of alkylphenols which comprises reacting phenol with the corresponding olefin under adiabatic conditions in the presence of a catalyst comprising an acidic montmorillonite clay having the structure:M.sub.x/n.sup.n+ .multidot.yH.sub.2 O(Al.sub.4-x Mg.sub.x)(Si.sub.8)O.sub.20 (OH).sub.4where M represent the interlamellar (balancing cation, normally sodium or lithium) and x, y and n are integers, wherein the acidic clay has been pretreated with an acid and optionally has deposited thereon an acid selected from the group consisting hydrogen fluoride, a fluorosulfonic acid or a mineral acid, at a temperature of from 60.degree. C. to 250.degree. C. and a pressure of from near atmospheric to about 500 psi.

Abstract: There are disclosed novel compositions of matter comprising monoalkylphenols prepared by selectively alkylating the olefin component of a thermally cracked sulfur-containing petroleum distillate derived from residua. The monoalkylphenols have certain ortho to para ratios and may be used to prepare a number of useful derivatives such as ethoxylated and propoxylated surfactants, sulfoalkylated products, sulfurized antioxidants, overbased phenates, dithiophosphate derivatives, formaldehyde reaction products and similar methylene bridged products which are useful demulsifiers.

Abstract: There are disclosed novel compositions of matter comprising monoalkylphenols prepared by selectively alkylating the olefin component of a thermally cracked sulfur-containing petroleum distillate derived from residua. The monoalkylphenols have certain ortho to para ratios and may be used to prepare a number of useful derivatives such as ethoxylated and propoxylated surfactants, sulfoalkylated products, sulfurized antioxidants, overbased phenates, dithiophosphate derivatives, formaldehyde reaction products and similar methylene bridged products which are useful demulsifiers.

Abstract: Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene below the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.

Abstract: The process for preparing 4-isopropylphenol (4-IPP) from 2-isopropylphenol (2-IPP) comprising contacting phenol with 2-IPP in the presence of a catalyst system selected from: (1) the combination of sulfuric acid on comminuted acid clay and a molecular sieve; and (2) trifluoromethane sulfonic acid (TFMSA); at a temperature of from about 90.degree. C. to about 250.degree. C., preferably from about 110.degree. C. to about 200.degree. C., wherein the initial mole ratio of phenol/2-IPP is from about 6 to about 2, preferably from about 4 to about 2.5, for a sufficient period to give a mole ratio of 4-IPP/2-IPP in the reaction system of from about 0.6 to about 1.5, and preferably from about 0.8 to about 1.2, without significant meta-isopropylphenol formation, i.e., less than about 10 mole %. In the isolation procedure, distillation separates the reaction mixture into phenol, 2-IPP, and 4-IPP.

Abstract: p-tert-octyl phenol is produced by reaction of phenol with diisobutene in the presence of an acidic ion exchanger and water, in a first stage, in a solid-bed reactor at temperatures of 110.degree.-140.degree. C. and under an excess pressure of up to 5 bar. The resultant dioctyl phenol formed as a by-product is alkylated in a second stage in a further solid-bed reactor with phenol in the presence of an acidic ion exchanger, and water at temperatures of 110.degree.-140.degree. C. and under an excess pressure of up to 5 bar to obtain additional p-tert-octyl phenol.

Abstract: Resorcinol is prepared by an improved process through superacid (such as perfluorinated alkanesulfonic superacids 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 superacid of one to eighteen 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 continuous process is provided for the production of para alkyl phenols. In the process a mixture of phenol, olefin and strong organic acid, is reacted for a brief period of time. The resulting reaction mixture is quenched, and the para alkyl phenol recovered.

Abstract: Alkylation of 4-alkylphenols with 2-methylpropene in the presence of a macroreticular cation exchange resin bearing sulfonic acid groups with an internal surface area greater than about 200 m.sup.2 /g and an average pore diameter less than about 120 Angstroms leads to the 2,6-dialkylated product in high yields. Using a resin with an internal surface area of from about 525 to about 575 m.sup.2 /g and an average pore diameter from about 40 to about 60 Angstroms, there can be prepared from 4-methylphenol the antioxidant 2,6-di-tert-butyl-4-methylphenol in a yield in excess of 90%.

Abstract: A method of eliminating color-causing impurities in mixtures of t-butylalkyl phenols by treatment with trioxane at 100.degree. C. and 1 atmospheric pressure is described. These phenols are used as peroxide inhibitors in polyol formulations for polyurethane foams. Discoloration of the polyol occurs if the phenol mixture is not treated with trioxane. It is an essential part of the invention that the t-butyl alkylphenol mixture be derived from an alkylphenol made over an acid resin catalyst. Mixtures made by a BF.sub.3 process may not be decolorized by this method. Generally, the color decreases with increasing amounts of trioxane.

Abstract: Hydroxy-substituted aromatic compounds may be alkylated by treatment with an alkylating agent such as an olefin or an alcohol at a temperature in the range of from about 50.degree. to about 200.degree. C. and a pressure in the range of from about atmospheric to about 100 atmospheres in the presence of a fluoro-substituted resin. The resulting product will comprise both mono- and di-alkylated hydroxy-substituted aromatic compounds.

Abstract: Hydroquinone is subjected to an alkylation reaction utilizing isobutylene or t-butyl alcohol as the alkylating agent to obtain t-butyl hydroquinone. The alkylation reaction is effected in the presence of an acidic catalyst such as phosphoric acid at temperatures ranging from about 75.degree. to about 200.degree. C. and a pressure in the range of from about atmospheric to about 100 atmospheres. By employing a mixture of a nonpolar hydrocarbon solvent such as xylene and an aliphatic ketone such as 2-heptanone, it is possible to obtain a greater ratio of mono-alkylated product to di-alkylated product.

Abstract: Detrimental color change of phenolic antioxidants during production, storage and use in rubbers is inhibited by adding during the synthesis of the phenolic antioxidant a disubstituted hydroxylamine to the catalyst neutralization solution and a substituted oxime together with a disubstituted hydroxylamine to the reaction mixture prior to filtration.

Abstract: A mixture of 2,4-/2,5-xylenol can be alkylated with a suitable alkylating agent over a strongly acidic divinylbenzene-styrene copolymer to afford a greater amount of 4-t-alkyl-2,5-xylenol than 6-t-alkyl-2,4-xylenol provided the alkylation is carried out at a suitably low temperature of 60.degree. C. or less.

Abstract: A process for the conversion of an alkyl phenyl ether to the corresponding alkylphenol, involving heating in the presence of a dehydrated sulfonic acid type cation exchange resin having a macroreticular structure. The process has particular application to the recovery of unreacted alkylphenol from a product mixture resulting from a reaction in which the alkylphenol is used (in stoichiometrically excessive amounts) as a reactant.

Abstract: Butylation of a mixture of xylenols and trimethylphenols gives a product which is suitable for use as a stabilizer for polyvinyl chloride. The material can be added to the reactor during polymerization as a shortstopper and retain effectiveness as a stabilizer in the finished polymer.

Abstract: A process for preparing 5-t-butyl alkylphenols from alkylphenols in high selectivity is disclosed, wherein the starting alkylphenol is a 3-alkylphenol or a 2,3-dialkylphenol and the alkyl group is a C.sub.1 -C.sub.6 primary alkyl. The process comprises reacting a 3-alkylphenol or a 2,3-dialkylphenol, wherein the alkyl group is a C.sub.1 -C.sub.6 primary alkyl, with isobutylene in the presence of a catalyst, which is a sulfonated polystyrene crosslinked with divinylbenzene, at a temperature of at least 100.degree. C.

Abstract: A process for preparing 6-t-butyl alkylphenols from alkylphenols in high selectivity is disclosed, wherein the starting alkylphenol is a 3-alkylphenol or a 2,3-dialkylphenol and the alkyl group is a C.sub.1 -C.sub.6 primary alkyl. The process comprises reacting a 3-alkylphenol or a 2,3-dialkylphenol, wherein the alkyl group is a C.sub.1 -C.sub.6 primary alkyl, with isobutylene in the presence of a catalyst, which is a sulfonated polystyrene crosslinked with a divinylbenzene, at a temperature of 50.degree. to 90.degree.C.

Abstract: In a process for the manufacture of a p-alkylphenol by alkylating phenol with an olefin of 3 to 4 carbon atoms, at an elevated temperature, in the liquid phase, in two reaction zones in series and in the presence of a strongly acidic ion exchange resin as the catalyst, an improvement comprises:(a) passing in a first reaction stage at a temperature of 80.degree.-140.degree. C. over a suspended catalyst, the olefin as a gas at a gas velocity of 30 to 20 cm/second, based on the free cross-section of the empty reactor and on a molar volume of 25 liters per mole of olefin, from below into the reaction mixture; and(b) passing the resulting liquid reaction product, into a second reaction stage, at a temperature of 80.degree.-140.degree. C. over a fixed-bed catalyst;wherein a catalyst having an exchange capacity of 70-120 m. equivalents/100 cm.sup.3 is used in both reaction stages.

Abstract: Butylation of a mixture of xylenols and trimethylphenols gives a product which is suitable for use as a stabilizer for polyvinyl chloride. The material can be added to the reactor during polymerization as a short-stopper and retain effectiveness as a stabilizer in the finished polymer.

Abstract: Alkylphenol compounds are manufactured by continuous reaction of phenolic compounds with olefins in the presence of a pulverulent polystyrenesulfonic acid exchanger suspended in the reaction mixture. The products are starting materials for the manufacture of dyes, pesticides, pharmaceuticals, emulsifiers, dispersing agents, stabilizers, antioxidants, plasticizers, corrosion inhibitors, disinfectants, seed dressings, aging inhibitors, crop protection agents and scents.

Abstract: p-alkylphenols are manufactured by continuous reaction of phenol with olefins in the presence of a pulverulent polystyrenesulfonic acid ion exchanger which is suspended in the reaction mixture.

Abstract: An improved process for the continuous alkylation of phenol with olefins having 6 to 12 carbon atoms in the liquid phase and in the presence of strongly acid ion exchange resin catalysts mounted in a fixed bed. The phenol and olefins are passed in a first stage at temperatures from about 80.degree. to 120.degree. C. over an ion exchange resin catalyst having an exchange capacity of from 50 to 96 m Val per 100 ml of catalyst and then passed in a second stage at temperatures about 110.degree. to 130.degree. C. over another ion exchange resin catalyst having an exchange capacity of from 100 to 180 m Val per 100 ml of catalyst.

Abstract: An improved process of preparing phenolic antioxidants in increased yields with superior color properties, the improvements being obtained by carefully controlling process variables such as the temperature of the reaction, moisture level and catalyst level.