Abstract: A process is disclosed for the oxidation of esters of para- and meta-methyl-substituted phenols to the corresponding aromatic carboxylic acid in the presence of a promoter comprising an anhydride of a lower aliphatic carboxylic acid and a heavy metal catalyst with or without the presence of bromine. The resulting carboxylic acids are useful in liquid crystal polymers and polymers useful in engineering plastics.

Abstract: This invention relates to the production of a solid oxidized coal containing humic acids. Coal with a mean particle size of less than 3 mm is slurried with water and then oxidized with oxygen or mixtures of oxygen and air at temperatures ranging from 100.degree. to 300.degree. C., at partial oxygen pressures ranging from 0,1 to 10 MPa and reaction periods ranging from 5 to 600 minutes. In the absence of catalysts, e.g. alkaline bases, the main product of oxidation is humic acids. These humic acids are not dissolved because the pH of this slurry is in the range 4 to 9. Small amount of fulvic acids are formed and these are soluble in the water of the slurry.The coal-derived humic acids may for example find application as soil conditioners, organic fertilisers, briquette and pellet binders, drilling fluid dispersants and viscosity control agents, while the coal-derived fulvic acids may be utilized for the production of fuel extenders, plasticizers and petrochemicals.

Abstract: Centrifugates obtained by centrifuging the reaction product of a process in which organic acids selected from the group consisting of higher alkyl benzene sulfonic acids, higher alkyl naphthenic acids, higher alkyl salicylic acids and higher alkyl phenols or alkali metal salts of the acids are contacted with a base acting alkaline earth metal compound to produce an alkaline earth metal salt of the selected acid are mixed with a quantity of an aqueous solution of an acid having an ionization constant greater than 1.times.10.sup.-5 sufficient to bring the pH of the centrifugate-acid mixture to a level in the range about 2 to 10 and settling the mixture to separate a lower aqueous phase and an upper liquid product phase and recovering the upper phase.

Abstract: A process for the production of aromatic carboxylic acids which comprises carbonylating substituted iodoaromatic compounds in the presence of carbon monoxide, a catalytic amount of a transition metal catalyst, and a Bronsted base in a mixture of a carboxylic acid and water under aromatic carboxylic acid forming conditions of temperature and pressure.

Abstract: Particulate aluminum is intimately mixed with an aromatic material that contains at least one ar-halo substituent having an atomic number above 20 and at least one side-chain halo substituent having an atomic number below 20 in the presence of an aqueous alkali or alkaline earth metal hydroxide so as to effect selective removal of the ar-halo substituent.

Abstract: Essentially pure para-hydroxybenzoic acid crystals, typically containing but trace amounts of inorganic potassium salts and salicylic or 4-hydroxyisophthalic acid, well adopted for foodgrade applications, are facilely recovered from an aqueous solution of dipotassium and/or monopotassium para-hydroxybenzoate by (i) adding an organic solvent for para-hydroxybenzoic acid to such aqueous solution, in an amount sufficient to dissolve the para-hydroxybenzoic acid corresponding to said potassium salts thereof, (ii) next adding thereto an at least stoichiometric amount, relative to said dipotassium and/or monopotassium salt of para-hydroxybenzoic acid, and (iii) separating therefrom an essentially organic phase which comprises said para-hydroxybenzoic acid and an aqueous phase which comprises an inorganic potassium salt.

Abstract: A process is disclosed for the production of humic acids, which comprises an oxidation of coal in dry phase with oxygen or mixtures of oxygen and nitrogen in a fluidized-bed reactor, by using coal with a granulometry comprised within the range of from 100 .mu.m to 3 mm and operating at a temperature comprised within the range of from 150.degree. to 300.degree. C., under a partial pressure of oxygen comprised within the range of from 1.1 abs.atm. to 10 abs.atm., for a contact time comprised within the range of from 30 minutes to 600 minutes.

Abstract: A process for the preparation of p-hydroxybenzoic acid from p-methoxytoluene wherein said p-methoxytoluene is oxidized to p-anisic acid and said p-anisic acid is cleaved to p-hydroxybenzoic acid.

Abstract: The present invention provides a method for preparing solid p-disodium hydroxybenzoate which is characterized by comprising the steps of reacting phenol, carbon tetrachloride in an amount of 0.9 to 1.2 moles per mole of phenol and sodium hydroxide in an amount of 7 to 20 moles per mole of phenol prior to the reaction in an aqueous liquid containing 10 to 40% by weight of p-disodium hydroxybenzoate and/or sodium chloride in the presence of a transition metal powder in an amount of 0.01 to 1.00% by weight based on the weight of a reaction system at a reaction temperature of 50.degree. to 150.degree. C.; cooling the resulting reaction mixture to a level of -20.degree. to +20.degree. C.; and separating said p-disodium hydroxybenzoate therefrom.

Abstract: This invention relates to methods of preventing or reducing the degradation of elastin and other proteins and thereby preventing or retarding the disease states caused by said degradation by administering compounds of the formula: ##STR1## or their pharmacologically acceptable salts.

Abstract: Acyloxy aromatic carboxylic acids, e.g., 4-acetoxybenzoic acid, are prepared by oxidizing with oxygen an acyloxy aromatic ketone, e.g., 4-acetoxyacetophenone in the presence of manganese cations and a lower-carboxylic acid anhydride as catalyst and a co-reductant or promoter. The acyloxy aromatic ketone may be prepared by acylating a hydroxy aromatic ketone, e.g., 4-hydroxyacetophenone, which has the effect of "masking" the hydroxyl group of the ketone in a manner necessary to effect the subsequent transition-metal catalyzed oxidation of the ketone to the acyloxy aromatic carboxylic acid.

Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophlic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.

Abstract: A process is provided for the production of 4-acetoxybenzoic acid by subjecting phenyl acetate to a Fries rearrangement or phenol and an acetylating agent to a Friedel-Crafts acetylation to form 4-hydroxyacetophenone which is then acetylated with an acetylating agent such as acetic anhydride to form 4-acetoxyacetophenone. The 4-acetoxyacetophenone is then oxidized with oxygen in the presence of manganese cations and acetic acid as catalysts and a co-reductant or promoter to form 4-acetoxybenzoic acid. The acetylation of the 4-hydroxyacetophenone has the effect of "masking" the hydroxyl group of the latter compound in a manner necessary to effect the subsequent oxidation of the ketone group of the 4-acetoxyacetophenone.

Abstract: By reacting a phenol compound with an organic halide selected from the group consisting of a haloform, a carbon tetrahalide and a substituted or unsubstituted allyl halide in the presence of an alkali metal hydroxide, using as a catalyst a fixed cyclodextrin having hydroxyl groups crosslinked with a bivalent hydrocarbon group having free valences at its both ends, said hydrocarbon group having at least one hydrogen atom substituted or unsubstituted with a member selected from the group consisting of an alkyl group, a halogen atom and a hydroxyl group and containing or not containing at least one combination of two neighboring carbon atoms having therebetween at least one member selected from the group consisting of an oxygen atom, a sulfur atom and a phenylene, various useful para-substituted phenol derivatives can be advantageously obtained.

Abstract: The electronegative surface charge of humic acid-containing materials is increased by treating the humic acid-containing material with anhydrous hydrochloric acid. The humic acid-containing material of enhanced surface charge is an effective viscosity reducing additive for water base drilling fluids and other aqueous suspensions of solids.

Abstract: This invention relates to methods of preventing or reducing the degradation of elastin and other proteins and thereby preventing or retarding the disease states caused by said degradation by administering compounds of the formula: ##STR1## or their pharmacologically acceptable salts.

Abstract: P-oxybenzoic acid derivatives of formula (1) ##STR1## wherein R.sup.1 is hydrogen, or straight or branched alkyl of one to four carbon atoms;n is 1 or 2;X is ##STR2## and R.sup.2 is --OH or --NHCH.sub.2 COOH; and non-toxic pharmaceutically acceptable salts thereof.The compounds exhibit a hypolipemic effect. They may be prepared by methods known in themselves from the corresponding ester or acid halide compounds, wherein optionally the secondary alcohol group may be oxidized to a keto group.

Abstract: By reacting, using as a catalyst a modified or unmodified cyclodextrin, a phenol compound with an organic halide selected from the group consisting of a carbon tetrahalide and a substituted or unsubstituted allyl halide in the presence of an alkali metal hydroxide, a substituent group derived from said organic halide can be introduced to the para-position of the phenol compound with high selectivity, whereby various useful para-substituted phenol derivatives can be advantageously obtained.

Abstract: This invention relates to methods of preventing or reducing the degradation of elastin and other proteins and thereby preventing or retarding the disease states caused by said degradation by administering compounds of the formula: ##STR1## or their pharmacologically acceptable salts.

Abstract: A mixture of intermediate products including a carboxylic salt of 3,4,5-trimethoxybenzoic acid (TMB acid) and a dimethoxy benzoic acid derivative of such salt further containing an oxygen anion in the 3,4, or 5 position is prepared by initially reacting hydrolyzable tannin with a methylation agent in an alkaline medium under methylation conditions to form methylated tannin and thereafter hydrolyzing the methylated tanning by reaction thereof with a hydrolysis agent under alkaline hydrolysis conditions. The resulting reaction mixture is then methylated to form a reaction mixture containing methyl 3,4,5-trimethoxybenzoate and a salt of 3,4,5-trimethoxybenzoic acid. TMB acid can be formed in high yield by conversion of both the methyl ester thereof and the salt thereof. Such conversion can be effected by hydrolyzing the reaction mixture followed by acidification thereof.

Abstract: An aromatic compound is hydroxylated by reacting the aromatic compound in an aqueous solvent with a triiodide salt to form a reaction mixture containing the corresponding iodoaromatic compound. The mixture is reacted, without separating the iodoaromatic compound, with a hydroxylating agent to form the corresponding hydroxy aromatic compound. The iodide salt, formed as a by-product of the reaction, is then separated for reuse in the process.

Abstract: An alkylated phenolic ether is prepared by reacting in the absence of a protic solvent a phenolic compound containing an unreacted phenolic hydroxy group with an alkyl sulfite of the formula (RO).sub.2 SO in which R is a one to four carbon alkyl group, the reaction occurring in one step and without the intermediate preparation of a phenolate.

Abstract: A methylated phenolic ether is prepared by reacting in the absence of a protic solvent a phenolic compound containing an unreacted phenolic hydroxy group with trimethyl phosphate, the reaction occurring in one step and without the intermediate preparation of a phenolate.

Abstract: Milbemycin and avermectin macrolides are synthesized by the cyclized linking of separately synthesized northern and southern hemisphere intermediates. The northern hemisphere intermediate is a spiroketal alkenyl aldehyde, and the southern hemisphere intermediate is an aryl alkenyl phosphine oxide anion.

Abstract: 3-Hydroxybenzoic acid is obtained by reaction with an alkali metal hydroxide at a temperature of 220.degree. to 450.degree. C. and under a pressure of 1 to 120 bars, from a technical 3-sulphobenzoic acid mixture which contains sulphuric acid and/or sulphur trioxide and which contains at least 75% by weight of 3-sulphobenzoic acid, relative to the total organic constituents present, and not more than 35% by weight of sulphuric acid and/or SO.sub.3, relative to the total mass. For this purpose, this technical 3-sulphobenzoic acid mixture, if desired after dilution with an equal volume of water, is mixed with sufficient 50 to 100% strength by weight alkali metal hydroxide wherein the remaining 50 to 0% by weight consists essentially of water, for 2.5 to 8 mols of alkali metal hydroxide to be present per mol of 3-sulphobenzoic acid, after neutralization of the sulphuric acid and all the sulpho and carboxyl groups. In general, 10 to 45% by weight of water are present in the batch.

Abstract: A process for preparing hydroxy aromatic carboxylic acids, or the ester derivatives thereof, comprises carbonylating a hydroxy aromatic halide in the presence of a reactive alcohol solvent and a catalytic amount of a Group VIII metal catalyst. The process has particular applicability to the preparation of 6-hydroxy-2-naphthoic acid from 6-bromo-2-naphthol, which can be easily prepared from .beta.-naphthol, a readily available and inexpensive starting material.

Abstract: A method for synthesizing alpha amino acids proceding through novel intermediates of the formulas: R.sub.1 R.sub.2 C(OSOCl)CN, R.sub.1 R.sub.2 C(Cl)CN and [R.sub.1 R.sub.2 C(CN)O].sub.2 SO wherein R.sub.1 and R.sub.2 are each selected from hydrogen monovalent substituted and unsubstituted hydrocarbon radicals of 1 to 12 carbon atoms. The use of these intermediates allows the synthesis steps to be exothermic and results in an overall synthesis method which is faster than the synthesis methods of the prior art.

Abstract: A process for the preparation of meta sulfobenzoic acid wherein after solution sulfonation of benzoic acid, meta sulfobenzoic alkali metal salt is precipitated by treating the solution with an alkali metal salt at a temperature below about 120.degree. C. The precipitate is then filtered from the solution and rinsed at least once with a cold rinse solution containing from 3 to 10 percent of an alkali metal salt The resulting product has a lower concentration of alkali metal salt, usually sodium chloride, than was obtained using prior art methods. The product is especially suitable for use in a process to manufacture m-hydroxy benzoic acid.

Abstract: A process for the preparation of an alkali metal salt of 3-hydroxybenzoic acid and the preparation of 3-hydroxybenzoic acid therefrom is disclosed wherein sulphophthalic acid or a salt thereof is reacted with an alkali metal hydroxide at a temperature in the range of 200.degree. to 300.degree. C. at a pressure of 10 to 30 bars.

Abstract: A method for recovering purified m-hydroxybenzoic acid from crude m-hydroxybenzoic acid alkali metal salt. The method comprises dissolving the crude m-hydroxy benzoic acid alkali metal salt in water at a ratio of between about 13 and 20 milliliters of water per gram of pure m-hydroxybenzoic acid alkali metal salt contained in the crude salt; acidifying the resulting solution to a pH of below 2 with a mineral acid to neutralize all alkali metal hydroxide present and to convert the m-hydroxybenzoic acid alkali metal salt to free m-hydroxybenzoic acid; and cooling the solution to from about 0.degree. C. to about 15.degree. C. for a sufficient time to crystallize purified m-hydroxybenzoic acid from the solution.The method is particularly effective for removing impurities of parahydroxybenzoic acid, alkali metal hydroxide and water soluble inorganic salts.

Abstract: A new compound is produced which has the general formula: ##STR1## wherein R represents hydrogen atom or a lower alkyl group and which exhibits an immunopotentiating activity. This new compound as well as its pharmaceutically acceptable salts and hydrates are useful for immunotherapy and treatment of immune diseases and disorders in living animals including human beings. The new compound can be produced by reduction of a hydroxyterephthalic acid alkyl ester or by esterification of the corresponding 3-hydroxy-4-(hydroxymethyl)-benzoic acid.

Abstract: A liquid humic acid concentrate and a process for making the same is disclosed in which the humic acid is formed by mixing a humic acid bearing ore in a quantity of water and caustic soda for a specified period of time and continuing to mix to form a liquid product of humic acid.

Abstract: Oxidative dye compositions for keratin fibres are provided which contain a 2,5-dihydroxyphenylalkanoic acid or salt thereof as antioxidant.

Abstract: Carboxylic acids and/or esters are prepared by converting the ##STR1## moiety in a 1-substituted 2,2-trihaloethanol, or derivative wherein X represents halogen and R is hydrogen or an acyl group to an organic acid and/or ester grouping of the formula ##STR2## wherein R' is hydrogen or alkyl of 1 to 6 carbon atoms, in the process which comprises reacting the 1-substituted 2,2,2-trihaloethanol or acylated derivative with molecular oxygen in the presence of a catalyst comprising a complex of a transition metal having an atomic number from 21-30, 39-48 or 57-80 and at least one molecule of a ligand containing trivalent nitrogen, phosphorus, arsenic or antimony. This reaction is carried out in a reaction medium comprising an alcohol or aqueous alcohol having 1 to 6 carbon atoms optionally containing an alkali metal, said alcoholic solvent also serving as a reactant source when carboxylic acid esters are formed.

Abstract: A process for the preparation of aromatic ethers by the bromination of a compound of the formula ##STR1## wherein R.sub.1, independently, is hydrogen, hydroxy, lower alkoxy, lower alkyl; m is an integer from 1-4, and A is --CHO, --COOR.sub.3 or lower alkyl, and subsequently treating the reaction product of the bromination step with an alkali metal alkoxide in the presence of cuprous halide or oxide, is described.

Abstract: Demethylation of the 3,4,5-trimethoxybenzoic acid is carried out in the presence of an excess of alkali hydroxide in an amount of ethylene glycol just sufficient to obtain a heterogeneous medium sufficiently fluid in the course of the operation. The ethylene glycol monomethyl ether and the water formed are distilled off progressively with their production and the resulting 4-hydroxy-3,5-dimethoxybenzoic acid is separated by acidification by means of a strong acid and crystallization.

Abstract: Novel monoazo dyes (sparingly soluble in water) which are free of sulphonic groups and which contain an aliphatic-carboxylic chain directly bound to the aryl nucleus of the coupling compound are particularly useful in uniformly dyeing polyamide fibers and/or fabrics yellow to orange-yellow.

Abstract: The invention relates to an improved method of preparing salicylic acid and derivatives from phenyl esters which comprises the step of fusing acetoxyphenyl, or derivative suitable for preparing the desired salicylic acid derivative, with M.sub.2 CO.sub.3 where M is potassium or sodium in the presence of carbon dioxide, at a temperature of from 150.degree. to 250.degree. C., and at a pressure of from atmospheric to 500 p.s.i.g.

Abstract: Metal complex polyazo dyes having, as a coupling component radical, the radical of a coupling component K, being the product of the condensation, under acidic conditions, of the formaldehyde with a compound or mixture of compounds of formula (a), ##STR1## AND/OR A COMPOUND OR MIXTURE OF COMPOUNDS OF FORMULA (B), ##STR2## WHEREIN EACH R.sub.1 , R.sub.2, R.sub.3 and R.sub.4 is independently is hydrogen, halogen, hydroxy or optionally substituted alkyl or alkoxy, andM is hydrogen or a non-chromophoric cation,The mol ratio of formaldehyde to the other compound(s) (a) and/or (b) being at least 0.6:1 and at least 50 mol % of the other compound(s) (a) and/or (b) containing a --COOM group, and, as diazo or bisdiazo component radical, a radical D- or -D- where D contains at least one metallized azo group, their production and their use for the dyeing of anionic dyeable substrates, particularly leather. The dyes have good levelling capacity and the obtained dyeings possess notable fastness to light.