Abstract: The present invention relates to a process for the preparation of tetrafluorophthalic acid and/or tetrafluorophthalic anhydride by reacting a compound of the formula ##STR1## in which X is a radical ##STR2## which is optionally mono- or polysubstituted on the aromatic nucleus by fluorine and/or chlorine and/or alkyl groups having 1 to 4 carbon atoms, or is a radical ##STR3## in which R.sub.1, R.sub.2 and R.sub.3 are as defined, with water, and subsequently removing the water still present by azeotropic distillation or extracting the tetrafluorophthalic acid and/or its anhydride with a water-insoluble solvent or solvent mixture.

Abstract: The invention relates to a method for the purification of benzoic acid, which is obtainable through oxidation of the corresponding toluene derivative, by treating it with a --NH.sub.2 or --NHR containing component in which R represents a carbon containing group, said component being applied to a support.

Abstract: A process for producing crystalline ibuprofen having a crystal habit characterized by a particle length larger than 75 microns average and a length to width aspect ratio of greater than about 4 to 1 to about 5 to 1. The process involves crystallizing ibuprofen from a saturated solution of ibuprofen in a liquid hydrocarbon solvent by seeding and cooling such solution to a temperature of about 0.degree. C. to about -20.degree. C. at a rate to retard primary nucleation and promote secondary nucleation. The crystalline ibuprofen is separated from the slurry produced from such cooling.

Abstract: This invention provides an improved method for recovering an organic acid as a salt from various process streams by addition of a crystallizing base to a concentrated solution of neutralized organic acid. The addition of such a base causes crystallization of the salt. This process provides more efficient recovery of organic acid salt from a fermentation process stream than traditional recrystallization and it may be used essentially as a one step purification process. The improved method is particularly applicable to the recovery of trisodium or tripotassium citrate from process streams produced in the fermentation and recovery of citric acid, with the addition of a crystallizing base such as sodium hydroxide, potassium hydroxide or ammonia.

Abstract: Disclosed is a process for isolating and purifying 2,4,5-trifluorobenzoic acid from a solution in a decarboxylating solvent such as NMP. The solution is neutralized with a hydroxide. This results in the formation of a salt of the 2,4,5-trifluorobenzoic acid, which precipitates. The slurry is filtered to collect the precipitated salt and the precipitated salt is dissolved in water. The aqueous solution of the salt is then acidified which results in the reformation and precipitation of the 2,4,5-trifluorobenzoic acid.

Abstract: Cyclodextrin derivatives and inclusion complexes having increased solubility and stability are provided. Cyclodextrin derivatives include amino and other modified cyclodextrins, and linked cyclodextrins. Inclusion complexes comprising the foregoing cyclodextrins, and processes for making the cyclodextrin derivatives are disclosed. Also disclosed are cyclodextrin derivatives comprising otherwise substituted or unsubstituted cyclodextrins covalently bonded to agents such as pharmaceuticals. The covalent bond, when broken, yields the agent in active form. Pharmaceutical compositions and methods of treating an animal host are also described, as well as chromatographic compositions and a method for separating racemic mixtures.

Abstract: A process is disclosed for the enantioselective hydrogenation of olefins of the formula: ##STR1## where R is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, Z is ##STR2## where R' is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, --CN, C(NH)OR" where R" is C.sub.1 to C.sub.6 linear or branched alkyl, or --C(O)NH.sub.2 ; and Ar is phenyl or naphthyl unsubstituted or substituted with benzoyl or substituted benzoyl, C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched alkoxy, halo, or carboxylic acid or C.sub.1 to C.sub.6 linear or branched alkyl ester thereof, which comprises contacting said aromatic-substituted olefin with a catalytically effective amount of a ruthenium phosphite complex.

Abstract: 3,4,6-Trifluorophthalic acid may be decarboxylated in a controlled manner to form 2,4,5-trifluorobenzoic acid by heating the phthalic acid in a dipolar aprotic solvent in the absence of any catalyst.

Abstract: There is here disclosed a method for obtaining high-purity cinnamic acid containing less metals from crude cinnamic acid containing a metallic catalyst which is a mixture prepared by the synthetic reaction of a cinnamic acid ester. A disclosed purifying means is the combination of alkali hydrolysis, active carbon adsorption, solvent extraction and precipitation with an acid.

Abstract: A process is disclosed for preparation of purified terephthalic acid containing 200 ppmw or less of p-toluic acid. A filter cake of purified terephthalic acid is prepared by filtering, under a differential pressure of about or greater than 0.5 psi over the system pressure and a temperature within the range of from about 100.degree. C. to about 205.degree. C., an aqueous slurry of purified terephthalic acid containing a solution of p-toluic acid. The aqueous solution of p-toluic acid remaining in the filter cake of purified terephthalic acid is displaced from the filter cake by water under a pressure gradient over the system pressure at a temperature within the range of from about 100.degree. C. to about 205.degree. C. Pressure flash evaporation of water remaining in the filter cake occurs upon release of the system pressure to lower pressure with consequent lower temperature. The crystalline terephthalic acid product containing 200 ppmw or less p-toluic acid can be dried under atmospheric pressure.

Abstract: This invention pertains to a method of purifying ibuprofen-comprising reaction product mixtures. The method of purification is based on crystallization of ibuprofen from a hydrocarbon solvent and the discovery that there are impurity complexes in the ibuprofen-comprising reaction product mixtures which cannot be removed by crystallization from a hydrocarbon solvent.The method of the invention includes at least one step in which the impurity complex in a first ibuprofen-comprising mixture is destabilized or broken up, followed by crystallization of the ibuprofen from a second solution or mixture comprising the first ibuprofen-comprising mixture, whereby the impurities which were previously complexed can then be removed from the ibuprofen by the crystallization of ibuprofen from a solvent.

Abstract: Carboxylic acids are recovered from wet organic solutions by reducing the solutions' water content thus causing the acids to precipitate as recoverable crystals.

Abstract: A process for the purification of crude benzoic acid obtained by the catalytic oxidation of toluene in the liquid phase, which is contaminated with impurities including phthalic acid and benzylbenzoate, the process involves distilling the crude benzoic acid in a first distillation in the presence of an aliphatic amine or a mixture of aliphatic amines of the formulaHNR.sup.1 R.sup.2whereinR.sup.1 represents hydrogen or a straight-chain or branched hydroxyalkyl or aminoalkyl radical with 1 to 6 carbon atoms andR.sup.2 represents a straight-chain or branched hydroxyalkyl or aminoalkyl radical with 1 to 6 carbon atoms,and/or the salts of these amines, recovering from this distillation (a) a purified benzoic acid and (b) a benzylbenzoate containing residue, working up the residue by a second distillation and chlorinating the distillate resulting from this second distillation to give a benzoylchloride virtually free of benzonitrile.

Abstract: The invention relates to a method for improving the color and the stability of the color of carboxylic acid or a mixture of the same by treating the carboxylic acid or its mixture with a hydride-yielding substance at an elevated temperature and by distilling the mixture thus obtained. The color and the stability of the color of the distillate thus obtained are better than the corresponding quantities of a distillate of untreated carboxylic acid or an untreated mixture of the same. Sodium borohydride and lithium aluminum hydride are preferred hydride-yielding substances. The method according to the invention can be applied to all carboxylic acids, advantageously to fatty acids and resin acids.

Abstract: A process for manufacturing high-purity o-toluic acid from a partial oxidation product of o-xylene is disclosed. o-Toluic acid is widely used as a raw material for agricultural chemicals, medicines, polymerization initiators, and the like. Depending on its use, 99% by weight or more purity is demanded for o-toluic acid. Hitherto, o-toluic acid having purity of higher than 99% by weight could not be obtained by fractionation, and purification by fractional crystallization was used. Fractional crystallization is, however, and expensive operation and not only gives a low yield of product but also results a large amount of waste water. The process disclosed herein gives an economical, commercial way to obtain high purity o-toluic acid.

Abstract: This invention relates to methods of preparing and purifying .alpha.-substituted acetic acids, which comprise treating an .alpha.aromatic-substituted acetic acid represented by a specific general formula with a weak alkali while shielding light, or subjecting an .alpha.-aromatic-substituted acetonitrile represented by a specific general formula to acid hydrolysis, followed by treatment with a weak alkali while shielding light; and treating the alkali salt of .alpha.-substituted acetic acid thus formed with a decolorizing agent.

Abstract: A process is provided for removing water from a mixture of hydrogen fluoride (HF), a carboxylic acid, e.g., acetic acid, and water by extractive distillation in the presence of a Lewis base as solvent, which does not azeotrope with water, forms bonds with the HF and carboxylic acid which can be broken by heat and has a boiling point at atmospheric pressure at least about 20.degree. C. above that of the carboxylic acid, e.g., N-methyl-2-pyrrolidone, and taking off an overhead vapor comprising a major proportion of the water in said mixture. The extractive distillation may be advantageously integrated in an overall process with the production of an aromatic ketone, e.g., 4-hydroxyacetophone, by the Friedel-Crafts acylation of an aromatic compound, e.g., phenol, with the carboxylic acid, using HF as catalyst, to produce a product mixture comprising the aromatic ketone, HF, carboxylic acid and water, and the removal of aromatic ketone from the product mixture by means of a solvent assisted distillation.

Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.2 is 1-pyrrolidinyl which may have 1 to 2 substituents selected from the group consisting of (i) C.sub.1 -C.sub.6 alkyl, (ii) amino-(C.sub.1 -C.sub.6)alkyl, said amino being optionally substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkanoyl, and C.sub.1 -C.sub.6 alkoxycarbonyl, (iii) amino which may be substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl, and C.sub.1 -C.sub.6 alkanoyl, and (iv) 2-oxo-1,3-dioxolenemethylamino which is substituted by C.sub.1 -C.sub.6 alkyl; or 1-piperidinyl which may have 1 to 3 substituents selected from oxo, hydroxy, halogen and C.sub.1 -C.sub.6 alkyl, and R.sup.3 is C.sub.1 -C.sub.

Abstract: An effective method for producing highly pure (aryl substituted)carboxylic acid or its salt which comprises the steps of:(I) oxidizing (aryl substituted)aldehyde in an acidic phase in the presence of hypohalogenite; and(II) bringing the oxidized product obtained in the preceding step into contact in a liquid phase with hydrogen in the presence of a catalyst of transistion metal of the group VIII in the periodic table.

Abstract: A process for extracting pure components from a multi-component system, said system comprising a mixture of at least two solids or liquids in a supercritical fluid at constant pressure, which involves making use of the cross-over pressure points of the components which comprise the system.

Abstract: An effective method for refining 2-(aryl substituted)propionic acid or its salt which is characterized in that 2-(aryl substituted)propionic acid or its salt containing halogenated by-products is brought into contact with hydrogen in a liquid phase containing water under a basic condition at temperatures in the range of 20.degree. C. to 170.degree. C. in the presence of a catalyst of transition metal of the group VIII in the periodic table, thereby dehalogenating said halogenated by-product and producing highly pure 2-(aryl substituted)propionic acid or its salt.

Abstract: The invention relates to a process for preparing purified, virtually odorless, solid benzoic acid obtained from toluene by oxidation with a gas containing molecular oxygen, by means of a treatment using an inert gas or gas mixture, wherein the benzoic acid to be purified is supplied in a liquid state to a fluid or spouted bed granulator in which the prevailing temperature is below the solidification temperature of the benzoic acid and in which the benzoic acid is treated, during and possibly after the granulating process, with the said gas or gas mixture, the impurities present being taken up in whole or in part in the gas or gas mixture, upon which the benzoic acid thus purified is removed from the fluid or spouted bed device.

Abstract: Process for recovering benzoic acid purified by means of a supercritical extraction of solid benzoic acid, characterized in that after the extraction the purified benzoic acid is remelted at least in part and is carried off from the melting device in at least partly liquid form.

Abstract: Process for purifying benzoic acid obtained by oxidation of toluene with a gas containing molecular oxygen, which purification is carried out at a pressure of at least 3 MPa by means of a supercritical extraction using a gas or gas mixture the critical temperature of which is lower than 435 K. The process being characterized in that the benzoic acid to be purified is supplied in a liquid state to a crystallizer in which the prevailing temperatures is below the solidification temperature of the benzoic acid and in which the benzoic acid is treated during and possibly after the crystallization process with the said gas or gas mixture.

Abstract: The invention is concerned with a method of purifying benzoic acid, as obtained by catalytic oxidation of toluene and purification by rectification with the secondary streams being cycled back into the oxidation reactor, characterized in that the secondary streams flowing out of the stripping column undergo the following sequential steps: (a) at least one distillation and at least one crystallization in an organic solvent; (b) scrubbing of the crystals obtained from (a) with the same solvent as in (a); (c) cycling of the mother liquors from crystallization in (a) plus the scrubbing liquors as in (b) back into the dissolver; (d) further scrubbing of the crystals from (b) with the same solvent as in (a) and cycling back of the scrubbing liquors, the crystals scrubbed as in (d) being optionally (d1) further scrubbed with water.

Abstract: Deamination of aromatic primary amines by diazotization and hydrogen replacement of the diazo group is accelerated in the presence of hydrogen peroxide. Yields of at least about 85% are typical, with reaction times of usually about one hour or less.

Abstract: Pharmaceutical benzoic acid is prepared from raw benzoic acid made of oxidation of toluene with an oxygen containing gas, the process is characterized in that the oxidation reaction product is contacted with at least 1 m.sup.3 per kg of benzoic acid of a gas with a critical temperature lower than 435 K by passing this gas through the oxidation reaction product at a flow rate of at least 1 m.sup.3 per hour per kg of benzoic acid at a temperature of 340-600 K. and a pressure of at least 3 MPa. The pharmaceutical benzoic acid is separated from the mixture by cooling it to 315-370 K. at a pressure of 3-300 MPa.

Abstract: Stereoisomerically-enriched esters are prepared by treating a non-symmetrical ketene with a racemic or chiral tertiary-base-substituted alkylcarbinol. Optional hydrolysis of the esters gives the corresponding optically-active carboxylic acids corresponding to the non-symmetrical ketene.

Abstract: Benzoic acid is prepared by oxidation of toluene with an oxygen containing gas, the process is characterized in that the oxidation reaction product is subjected to an extraction with a gas of which the critical temperature is lower than 435 K, this being effected by passing it during at least 1 minute over or through the oxidation reaction product at a flow rate of at least 1 m.sup.3 gas per hour per kg of benzoic acid at a temperature of 285-340 K and at a pressure of at least 3 MPa.

Abstract: This invention pertains to a process for separating nitration isomers of 1,3-disubstituted and 1,2,4-trisubstituted benzene compounds. The separated isomers have a variety of uses including precursors for 2-haloacetanilide herbicides.

Abstract: A thermal process for the decarboxylation and dehydration of aromatic acid residue to convert such residue to grindable form and recover the solvent of reaction therefrom.

Abstract: Ibuprofen is crystallized from a .delta.H.gtoreq.8 liquid such as a C.sub.1 to C.sub.3 -alkanol, e.g., methanol, containing solutions thereof to obtain ibuprofen crystals which are equant (cube, sphere or grain) in shape, which ibuprofen crystals have larger average partile size, higher bulk density, lower bulk volume and improved flow properties compared to previously known bulk ibuprofen crystalline materials.

Abstract: An improved process for isolating organic compounds from crude product or reaction mixtures by dissolving said crude product or reaction mixture in a suitable solvent, contacting the resulting solution with a lithium salt to form a solid metal salt complex, separating, and thereafter recovering a pure product by decomposing the lithium salt complex.

Abstract: Compounds of the structure ##STR1## wherein: Q is oxygen, sulfur or imino.X and Y are hydrogen, halogen, hydroxy, alkoxy, trifluoromethyl, nitro, carboxy, cyano, sulfonamido, sulfhydryl, alkyl, alkenyl, alkynyl, alkanoyl, alkylmercapto, amino, alkylamino, dialkylamino, alkysulfinyl, and alkylsulfonyl and may be the same or different;R.sub.1 is hydrogen, alkanoyl, substituted alkanoyl wherein the substituent is hydroxy, amino or cycloalkyl, aroyl, arylalkanoyl, or cycloalkylcarbonyl,n is an integer from 1 to 4 inclusive,R.sub.2 and R.sub.

Abstract: This invention relates to a method of producing an aqueous solution which comprises soluble benzene carboxylic acid salts which is substantially free of soluble humic acid salts. A first aqueous solution (22) which comprises soluble humic acid salts and soluble benzene carboxylic acid salts is reacted with carbon dioxide (32) and an inorganic chemical (34) selected from the group consisting of magnesium bicarbonate, magnesium carbonate, a double salt of magnesium carbonate, and mixtures thereof in a mixing zone (30) under conditions operable for converting the soluble humic acid salts to precipitated magnesium humic acid salts while maintaining the soluble benzene carboxylic acid salts in solution.

Abstract: A process for selective cracking of 1,4-disubstituted benzene compounds having at least one polar substituent. Mixtures containing isomers of such a compound are brought into contact with a specified type of shape selective crystalline zeolite catalyst under conditions of temperature and pressure conducive to reaction of said benzene compound, thereby selectively reacting the 1,4-disubstituted isomer in preference to the 1,2- and 1,3-disubstituted isomers of said polar benzene compound. The shape selective zeolite catalysts employed herein are crystalline zeolites characterized by a silica to alumina ratio of at least about 12 and a constraint index within the approximate range of 1 to 12.

Abstract: Disclosed is a process for the recovery of aromatic carboxylic acid or ester thereof from the residue fraction of the oxidation or esterification reaction mixture resulting from the oxidation or oxidation and esterification of an aromatic compound having at least one methyl or formyl group directly bonded to a ring carbon atom. The process comprises treating the residue fraction with hydrogen and a hydrogenation catalyst.

Abstract: A process for recovering carboxylic acids with a material of which the main component is a polymeric compound having a pyridine skeletal structure and a crosslinked structure, followed by desorbing the captured carboxylic acids by use of a desorbing agent.

Abstract: A substituted aromatic compound e.g. p-xylene is oxidized to an aromatic dicarboxylic acid e.g. terephthalic acid using a Co/Mn/Br catalyst in acetic acid and the slurry product is purified by treating with molecular oxygen and diluting with fresh acetic acid before separation of the terephthalic acid and mother liquor.

Abstract: The invention relates to a method for the preparation of a pure alkali metal benzoate, specifically of a pure alkali metal benzoate from benzyl benzoate prepared by oxidation of an alkyl benzene compound, specifically toluene, with a gas containing molecular oxygen, besides benzyl alcohol. Very specifically the invention relates to a method for the preparation of sodium benzoate besides benzyl alcohol.For this purpose crude benzyl benzoate is subjected to a treatment with a reducing substance to convert impurities, under such circumstance that, in the process, there will be no conversion of any substantial quantity of benzyl benzoate. Subsequently the benzyl benzoate is saponified to the alkali metal benzoate and benzyl alcohol.

Abstract: There is provided an improved continuous homogeneous catalytic carbonylation process wherein a mixed gas stream is removed from the carbonylation reactor, condensable liquids separated from said gas stream and said gas stream vented, the improvement comprising contacting said gas stream with a plurality of hollow fiber membranes selectively permeable to hydrogen under conditions substantially non-degrading of the membranes to generate a non-permeated gas stream of higher carbon monoxide content and recycling said non-permeated gas stream to the carbonylation process reactor. There is also provided for the recovery and recycle to the process of carbonylation products such as acetic or propionic acids by adsorption and removal from a solid adsorbent or absorption in a liquid absorbent.

Abstract: Process for recovering carboxylic acids from dilute aqueous solutions of alkali metal salts of such carboxylic acids by mixing such solutions with from 10 to 1000% of a supercritical solution comprising at least 10 mole % carbon dioxide at a pressure from 80 to 500 atm and preferably 100 to 350 atm and at a temperature of from 35.degree. to 200.degree. C. and preferably from 35.degree. to 100.degree. C. whereby the salt reacts with the carbon dioxide to form the carboxylic acid which dissolves in the supercritical fluid. The aqueous phase is allowed to separate from the supercritical fluid phase. The pressure of the supercritical phase is lowered which lowers the solubility of the carboxylic acid in the supercritical fluid so that an acid phase is formed separate from the supercritical fluid phase whereby recovery of the acid is effected.

Abstract: Odorless benzoic acid is prepared by treating benzoic acid, after crystallization, with an inert gas at temperatures in the range of 50.degree.-100.degree. C. The process is best carried out using benzoic acid crystals or particles having a particle size of less than 1 mm in a moving or fluidized bed.

Abstract: An alkali-metal benzoate is prepared besides benzyl alcohol from a contaminated benzyl benzoate reaction residue obtained in the oxidation of a monoalkyl-benzene compound with a gas containing molecular oxygen. The disclosed process provides for distillation of the contaminated benzyl benzoate in the presence of a basic substance and the resulting distillate is hydrolyzed using an alkali-metal base.In this way, the benzyl benzoate that previously could not be separated from certain tar components by distillation is converted into a pure alkali metal benzoate such as sodium benzoate, besides pure benzyl alcohol, so that a waste product that was previously useless is converted into useful substances.

Abstract: A method for processing a tar which is formed during the oxidation of an alkyl-benzene compound and which contains substituted or unsubstituted benzyl benzoate, which method comprises the steps of subjecting the tar to either hydrolysis or ammonolysis and then extracting the reaction mixture which is formed from the hydrolysis or ammonolysis. The extracting agent is organic and causes the reaction mixture to separate into liquid phases. The liquid phases are then separated for further processing.