Abstract: The specification discloses reacting a water soluble amino compound with a highly water reactive isocyanate by dissolving the isocyanate in a solvent, such as ethyl acetate, which is water insoluble to slightly water soluble and which has a degree of electrophilicity so as to attract the amino constituent of the amino compound. The two solutions are rapidly mixed together, affording superior yields of product.

Abstract: Gelatins are crosslinked in a non-anhydrous environment to yield water-swellable, essentially water-insoluble foams. The gelatin is contacted with a polyisocyanate at a pH between about 6 and about 8 and subjected to a high rate of agitation. The process of this invention can be employed to immobilize proteins, enzymes, antibodies, etc.

Abstract: Polyalkylenepolyamines are crosslinked in a non-anhydrous environment to yield water-swellable, essentially water-insoluble gels. The polyalkylenepolyamine is contacted with a polyisocyanate at a pH between about 5 and about 8 and subjected to a high rate of agitation. The process of this invention can be employed to immobilize proteins, enzymes, antibodies, etc.

Abstract: The title compounds are of the formula P --O--R--.sub.n R').sub.mwherein:P is a polymer matrix of sufficient structure and molecular weight so as to be substantially water- and hydrocarbon-insoluble;R is --CH.sub.2 CH.sub.2 O--, --CH.sub.2 CH.sub.2 CH.sub.2 O--, ##STR1## --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O- or a combination thereof; R' is hydrogen, hydrocarbyl or inertly-substituted hydrocarbyl;n is an integer of 3 to about 40; andm is a real number such that the weight percent of --O--R--.sub.n R') groups is at least about 1 percent of the total weight of the compound.A representative example of these compounds is the reaction product of a poly(ethyleneglycol ether) having a weight average molecular weight of about 300 and a chloromethylated polystyrene resin. These polymer-supported poly (alkyleneglycol ethers) are useful phase-transfer catalysts for a wide variety of reactions, such as alkylation, displacement and carbene formation.

Abstract: Quaternary ammonium salts and sterically unhindered, nucleophilic, tertiary amines are novel cocatalysts which are used in the process of reacting an alkali metal phenate, pyridinate or pyrimidinate with an O,O-dialkylphosphorochloridothioate or O-alkyl phenylphosphonochloridothioate to produce the corresponding phosphorothioates and phenylphosphonothioates. The process is conducted under alkaline conditions in a liquid reaction medium.

Abstract: Quaternary ammonium salts and sterically unhindered, nucleophilic, tertiary amines are novel cocatalysts which are used in the process of reacting an alkali metal phenate, pyridinate or pyrimidinate with an O,O-dialkylphosphorochloridothioate or O-alkyl phenylphosphonochloridothioate to produce the corresponding phosphorothioates and phenylphosphonothioates. The process is conducted under alkaline conditions in a liquid reaction medium.

Abstract: Mixtures of (1) a quaternary ammonium salt(s) and (2) a diazole are novel catalysts in the process of reacting an alkali metal phenate, pyridinate or pyrimidinate with an O,O-dialkyl phosphorochloridothioate or O-alkyl phenylphosphonochloridothioate to produce the corresponding title compounds. The process is conducted under alkaline conditions in a liquid reaction medium. As an example, O,O-diethyl O-(3,5,6-trichloro-2-pyridyl)phosphorothioate is prepared in excellent yields and purity by reacting sodium 3,5,6-trichloro-2-pyridinate with O,O-diethyl phosphorochloridothioate in a stirred methylene chloride-water reaction medium in the presence of a catalytic amount of benzyltriethylammonium chloride and 1-methylimidazole.

Abstract: The process of oxidizing organic compounds by dissolving the organic compound in a water-immiscible, inert organic solvent and contacting same with an aqueous hypohalite ion in the presence of a catalytic amount of a quaternary onium salt is improved by employing a primary alkyl ester as the organic solvent. For example, cyclohexylmethylamine is oxidized under mild conditions to a high yield of cyclohexylnitrile by dissolving the amine in ethyl acetate and contacting same with aqueous hypochlorite and in the presence of a catalytic amount of tetra-n-butylammonium chloride.

Abstract: Symmetrical ethers are prepared in high yield by reacting an alkyl halide, sulfate, or sulfonate with base in the presence of a catalytic amount of both an onium salt and a carboxylate salt. For example, dibenzyl ether is produced in yields exceeding 95 percent by contacting benzylchloride with a 50 percent sodium hydroxide solution in the presence of a catalytic amount of both tetra-n-butylammonium bisulfate and sodium acetate.

Abstract: Mixtures of (1) a quaternary ammonium salt(s) and (2) a diazole are novel catalysts in the process of reacting an alkali metal phenate, pyridinate or pyrimidinate with an O,O-dialkyl phosphorochloridothioate or O-alkyl phenylphosphonochloridothioate to produce the corresponding title compounds. The process is conducted under alkaline conditions in a liquid reaction medium. As an example, O,O-diethyl O-(3,5,6-trichloro-2-pyridyl)phosphorothioate is prepared in excellent yields and purity by reacting sodium 3,5,6-trichloro-2-pyridinate with O,O-diethyl phosphorochloridothioate in a stirred methylene chloride-water reaction medium in the presence of a catalytic amount of benzyltriethylammonium chloride and 1-methylimidazole.

Abstract: Quaternary ammonium salts and sterically unhindered, nucleophilic, tertiary amines are novel cocatalysts which are used in the process of reacting an alkali metal phenate, pyridinate or pyrimidinate with an O,O-dialkylphosphorochloridothioate or O-alkyl phenylphosphonochloridothioate to produce the corresponding phosphorothioates and phenylphosphonothioates. The process is conducted under alkaline conditions in a liquid reaction medium.

Abstract: Organic compounds oxidizable by hypohalite ion, such as amines, amides, primary and secondary alcohols, and alkanals are efficiently oxidized in a biphasic mixture comprising:A. a water immiscible, liquid organic phase comprising an organic compound oxidizable by hypohalite ion; withB. an aqueous phase containing hypohalite ion; andC. a catalytic amount of a quaternary ammonium salt and/or a quaternary phosphonium salt.

Abstract: Quaternary ammonium salts are novel catalysts in the process of reacting an alkali metal phenate, pyridinate or pyrimidinate with an O,O-dialkyl phosphorochloridothioate or O-alkyl phenylphosphonochloridothioate to produce the corresponding phosphorothioates and phenylphosphonothioates. The process is conducted under alkaline conditions in a liquid reaction medium. As an example, O,O-diethyl O-(3,5,6-trichloro-2-pyridyl)-phosphorothioate is prepared in excellent yields and purity by reacting solid particulate sodium 3,5,6-trichloropyridinate with O,O-diethyl phosphorochloridothioate dissolved in a stirred methylene chloride reaction medium in the presence of a catalytic amount of benzyltriethylammonium chloride.

Abstract: The reaction between the alkali metal halopyridinates with the lower alkyl esters of .alpha.-chloro or bromo acetic acid (or propionic acid) to form the corresponding O-alkylated halopyridinates is catalyzed by quaternary ammonium salts. For example, methyl .alpha.-(6-chloropyridinyloxy)acetate was prepared in excellent yield by reacting sodium 6-chloropyridinate with excess methyl .alpha.-chloroacetate in the presence of 2 mole percent of benzyl triethyl ammonium chloride.