Abstract: A mixture formed from an alkoxy-2-naphthaldehyde (e.g., 6-methoxy-2-naphthaldehyde), acetone, and aqueous NaOH and/or KOH is heated at about 20.degree. to about 56.degree. C. for about 0.25 to about 2 hours such that the conversion of monoalkoxy-substituted 2-naphthaldehyde is at least 97% and the yield of (alkoxy-substituted 2-naphthyl)-3-buten-2-one is at least 95% based on the monoalkoxy-substituted 2-naphthaldehyde used in forming the mixture. The (alkoxy-substituted 2-naphthyl)-3-buten-2-one can be hydrogenated using, for example, a Pd/C catalyst to form the corresponding saturated ketone. The process enables efficient production of precursors of nabumetone and related pharmaceuticals by a clean, highly efficient reaction.

Abstract: Bridged metallocene compounds are produced by a process of promising commercial utility for plant-sized operations. One of the key steps of the process involves converting a deprotonated silicon-, germanium- or tin-containing ligand into the metallocene. Preferably, and in accordance with an embodiment of the invention, this is accomplished to great advantage by adding a diamine adduct of a Group IV, V, or VI metal tetrahalide to a solution or slurry formed from a deprotonated silicon-, germanium- or tin-containing ligand and an organic liquid medium so as to form a metallocene. The overall process of the invention involves the direct conversion of benzoindanones to benzoindanols which, without isolation, are converted to benzoindenes. Thereupon the benzoindenes are bridged by deprotonating the benzoindenes with a strong base such as butyllithium and reacting the resultant deprotonated product with a suitable silicon-, germanium- or tin-containing bridging reactant such as dichlorodimethylsilane.

Abstract: Glyphosate formulations which are effective even when employed at dosages below the dosage currently recommended for post-emergent herbicidal or plant growth regulant use are described. They are formulated as water solutions or powders or granules of (a) one or more agriculturally acceptable salts of glyphosate, e.g., amine, ammonium, alkali metal, alkylsulfonium, alkylphosphonium, sulfonylamine, and/or aminoguanidine salts of glyphosate; (b) at least one water-soluble long chain aliphatic hydrocarbyl dimethyl amine oxide in which the hydrocarbyl group is a linear or substantially linear saturated or olefinically unsaturated aliphatic group having in the range of about 8 to about 22 carbon atoms; and (c) at least one water-soluble quaternary ammonium halide having in the range of about 8 to about 40 carbon atoms in the molecule.

Abstract: Sodium (S)-2-(6-methoxy-2-naphthyl)propionate of at least 99% chiral purity is formed from (S)-2-(6-methoxy-2-naphthyl)propionic acid having a chiral purity of at least about 82%, but below 99%. This is done by distilling a two-phase mixture formed from (i) the (S)-2-(6-methoxy-2-naphthyl)propionic acid, (ii) water, (iii) sodium hydroxide, sodium oxide and/or at least one basic inorganic sodium salt in an amount proportioned to neutralize from about 50 to about 99% of said acid, and optionally but preferably, (iv) an inert organic solvent that has a boiling point of at least 95.degree. C. at 760 mm Hg such that water is removed from said mixture, and a pot residue containing sodium (S)-2-(6-methoxy-2-naphthyl)propionate of at least 99% chiral purity is formed.

Abstract: N-?4-(cyanoethylthiomethyl)-2-thiazolyl!guanidine--a key intermediate for preparing the pharmaceutical, famotidine--is produced by mixing in a liquid medium formed from a chemically indifferent organic solvent and water, and under an inert atmosphere, (i) a 2-guanidino-4-halomethylthiazole or a hydrohalide complex thereof, (ii) an S-(2-cyanoethyl)isothiourea or a hydrohalide complex thereof, and (iii) a strong alkali metal base. In lieu of (ii), an alkali metal salt of 2-cyanoethyl-1-thiol can be used, and in such case use of (iii) is optional, but preferable.

Abstract: A slurry is formed from an auxiliary catalyst (e.g., an aluminoxane or organoboron compound), a porous inorganic oxide carrier, and an inert organic solvent. The slurry is enclosed in a closed vessel and the temperature and pressure of the enclosed slurry are increased to a temperature of from about 80.degree. C. to 250.degree. C. and a pressure of from about 5 to 500 psig such that a supported composition is produced in the vessel. After opening the closed vessel, the supported composition and the solvent are separated from each other.

Abstract: N-?4-(Cyanoethylthiomethyl)-2-thiazolyl!guanidine, is prepared by (a) mixing 1,3-dihaloacetone and 2-imino-4-thiobiuret in a suitable polar organic solvent at initial temperatures of about -10.degree. to about 25.degree. C., and agitating the mixture at about -10.degree. to about 60.degree. C. for at least about 1 hour; (b) heating the resultant mixture at about 40.degree. to about 60.degree. C. for at least about 0.5 hour; (c) mixing with the mixture from (b), thiourea and then water at about 40.degree. to about 60.degree. C. for a period of at least about 1 hour; (d) removing liquid polar solvent from the mixture of (c); and (e) mixing with the mixture from (d), 3-halopropionitrile and water-soluble alcohol, ether, or ether-alcohol, followed by aqueous alkali metal hydroxide while maintaining the temperature at below about 20.degree. C., to form N-?4-(cyanoethylthiomethyl)-2-thiazolyl!guanidine.

Abstract: Gaseous anhydrous hydrogen chloride is introduced into an aqueous solution of zinc chloride under conditions effective to produce a more efficient Lucas reagent than a Lucas reagent made by mixing solid, anhydrous zinc chloride with 38% hydrochloric acid. For example, the reaction rate of such Lucas reagent with levo-menthol is much faster and requires a much shorter reaction period than Lucas reagent formed in the conventional manner from anhydrous, solid zinc chloride and concentrated (38%) hydrochloric acid. Also, the conversion to levo-menthyl chloride was higher when using Lucas reagent formed using gaseous anhydrous hydrogen chloride and aqueous zinc chloride solution. Also, Lucas reagent made in this manner is highly amenable to recycling, and requires only addition thereto of hydrogen chloride to replenish the catalyst for an ensuing run.

Abstract: Novel aluminum-containing compositions having increased paraffin-solubility are produced from a methylaluminoxane composition having lower paraffin-solubility. These compositions are formed by mixing in liquid phase (A) at least one aluminum trialkyl (or solution or suspension formed therefrom), where the aluminum trialkyl has at least 30 carbon atoms in the molecule, where each alkyl group thereof is bifurcated in the 2-position into a pair of branches, where one such branch has n carbon atoms and the other such branch has at least n+2 carbon atoms, and where n is at least 3; and (B) at least one methylaluminoxane composition having lower heptane-solubility (or a solution or slurry formed therefrom). Preferably, the resultant mixture is agitated at one or more elevated temperatures at which the mixture becomes even more homogeneous.

Abstract: Chiral metallocenes are prepared by reacting a salt of an asymmetric bis(cyclopentadienyl)-moiety-containing ligand with a chelate diamine adduct of a transition, lanthanide, or actinide metal halide in an organic solvent or diluent so as to produce said chiral metallocene.

Abstract: A mixture formed from 2-naphthaldehyde (e.g., 6-methoxy-2-naphthaldehyde) and a dihydrocarbyl ketone having at least one hydrogen atom in the .alpha.-position (e.g., acetone) is heated in the presence of a heterogeneous basic catalyst (e.g., basic alumina) such that the unsaturated 2-naphthyl ketone is formed. The unsaturated ketone can be hydrogenated using, for example, a Pd/C catalyst to form the corresponding saturated ketone. The process enables efficient production of nabumetone and related pharmaceuticals by a clean reaction.

Abstract: Optically active carboxylic acids, salts or esters, such as the profen-type compounds, are racemized in the presence by nitrogenous bases such as methylbenzylamine by heating an aqueous solution of such optically active compounds in the presence of a suitable excess of an alkali metal hydroxide relative to the amount optically active carboxylic compound present in the solution. The process not only enables conversion of inactive or undesirable enantiomers of compounds such as naproxen or ibuprofen into a usable, desirable enantiomers in an efficient and economical manner, but avoids conversion of the nitrogenous base into amide. Thus the deleterious consequences of amide formation are avoided.

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: An essentially anhydrous agitated mixture of (i) finely-divided essentially anhydrous alkali metal fluoride (e.g., KF), (ii) haloaromatic compound having at least one halogen atom of atomic number greater than 9 on an aromatic ring (e.g., C.sub.6 Cl.sub.6), and (iii) an aminophosphonium catalyst (e.g., (Et.sub.2 N).sub.4 PBr), is heated at a temperature at which fluorine replaces one or more of the ring halogen atom of the haloaromatic compound.

Abstract: An anhydrous mixture containing a liquid phase and a solids phase formed from components comprising finely-divided sodium fluoride, hexabromobenzene, and a phosphonium catalyst, and optionally a liquid aprotic solvent/diluent, is heated at a temperature and for a time at which sodium bromide and at least one hexahalobenzene containing at least two fluorine atoms are produced. Preferably, the sodium fluoride is activated by one or more of procedures specified herein.

Abstract: Glyphosate formulations which are effective even when employed at dosages below the dosage currently recommended for post-emergent herbicidal or plant growth regulant use are described. They are formulated as water solutions or powders or granules of (a) one or more agriculturally acceptable salts of glyphosate, and (b) one or more particular types of quaternary ammonium compounds. The quaternary ammonium compound(s) are water-soluble compounds represented by the formula:R.sup.1 R.sup.2 R.sup.3 R.sup.4 N.sup..sym. X.sup..crclbar.wherein R.sup.1 is an aryloxyalkyl group having from 7 to about 16 carbon atoms, R.sup.2 is an alkyl group having in the range of about 10 to about 18 carbon atoms, R.sup.3 is a methyl or ethyl group, R.sup.4 is, independently, a methyl or ethyl group, or an alkyl group having in the range of about 10 to about 18, and X is a chlorine or bromine atom.

Abstract: An essentially anhydrous agitated mixture of (i) finely-divided essentially anhydrous alkali metal fluoride (e.g., KF), (ii) haloaromatic compound having at least one halogen atom of atomic number greater than 9 on an aromatic ring (e.g., C.sub.6 Cl.sub.6), and (iii) an aminophosphonium catalyst (e.g., (Et.sub.2 N).sub.4 PBr), is heated at a temperature at which fluorine replaces one or more of the ring halogen atom of the haloaromatic compound.

Abstract: (1) Alkali metal diarylphosphides are formed by mixing triarylphosphine with, and preferably introducing triarylphosphine into, a two-phase mixture one or more alkali metals, preferably a mixture or alloy of sodium and potassium, in an anhydrous organic liquid diluent in the presence of molecular hydrogen. (2) To form a cycloalkyldiarylphosphine, at least a portion of the reaction mixture formed as in (1) (or alkali metal diarylphosphide recovered therefrom) and cycloalkyl mesylate or tosylate are mixed together and maintained under suitable reaction conditions. Reaction (2) is driven by the presence of residual sodium from reaction (1). Conduct of reaction (2) under a hydrogen atmosphere suppresses undesirable side reactions.

Abstract: Continuously fed to and mixed in a first reactor are (i) a preformed mixture of primary hydrocarbyl monoamine, tertiary amine and liquid inert organic solvent, and (ii) thiophosphoryl chloride while removing heat of reaction to maintain the reaction temperature in the range of about -20.degree. C. to about +50.degree. C. A reaction mixture containing N-hydrocarbylaminothiophosphoryl dichloride is formed. Ammonia and an effluent stream from the first reactor are continuously fed to and mixed in a second reactor in proportions of at least about 16 moles, of ammonia per mole of N-hydrocarbylaminothiophosphoryl dichloride that produce a reaction mixture containing N-hydrocarbylthiophosphoric triamide, and that keep in solution ammonium chloride co-product formed in the reaction.

Abstract: A process for preparing a cyclopentenone by forming a two-phase mixture of a 1,4-diketone, a water immiscible organic solvent, and an aqueous base solution, and heating the mixture so as to convert the 1,4-diketone to a cyclopentenone which collects in the organic solvent phase.