Ppg Industries, Inc.

Ppg Industries Ohio, Inc.

James A Manner

Suresh B Damle

Robert G Briody

James A Cook, Jr

Charles H Hoelscher

Frederick F Guzik

Charles B Kreutzberger

Wendy E Wallace

Novel process for preparing carbamoyl pyridinium compounds using novel solvent/fatty amine reaction systems.

Process for preparing carbamoyl pyridinium compounds

Describes a process for preparing N,O-disubstituted hydroxylamine compounds comprising reacting an aqueous solution of free hydroxylamine with an equimolar amount of a carbonyl halide-containing compound, e.g., a chloroformate such as phenyl chloroformate, in the presence of a substantially stoichiometric amount of a weak inorganic basic reagent, thereby to produce the N-substituted derivative, and thereafter further reacting an inert organic solvent solution of the N-substituted derivative with an equimolar amount of the corresponding carbonyl halide-containing compound in the presence of a substantially stoichiometric amount of weak inorganic basic reagent, thereby to produce the N,O-disubstituted derivative, e.g., N,O-bis(phenoxycarbonyl) hydroxylamine. In a preferred embodiment, the organic solvent is used also in the reaction that produces the N-substituted derivative. N,O-disubstituted hydroxylamine compounds containing less than 3 weight percent, e.g., less than 0.5 weight percent, of the hydrolysis by-product of the carbonyl halide-containing compound may be produced thereby.

Process for preparing N,O-disubstituted hydroxylamine compounds

Ethyl chloroformate is chlorinated in the rectifying zone of a distillation reactor to produce 1-chloroethyl chloroformate and 2-chloroethyl chloroformate.

Synthesis of monochloroethyl chloroformates by free radical initiated

Disclosed is a method for selectively separating 2-nitrosophenol from an isomeric mixture containing 2-nitrosophenol and 4-nitrosophenol by contacting the mixture with an organic solvent so as to preferentially dissolve the 2-nitrosophenol from the mixture.

Method of separating 2-nitrosophenol isomer from admixture with

Organic haloformate, e.g., chloroformate, compounds are converted to their corresponding halides, e.g., chlorides, by heating the haloformate, e.g., between 90.degree. C. and 150.degree. C., in the presence of a catalytic amount of an organic quaternary salt, e.g., quaternary ammonium or phosphonium salts, for a time sufficient to convert the haloformate to the corresponding halide.

Method for converting organic chloroformate to the corresponding organic

Organic haloformate, e.g., chloroformate, compounds are converted to their corresponding halides, e.g., chlorides, by heating the haloformate, e.g., between 90.degree. C. and 150.degree. C., in the presence of a catalytic amount of a carbon catalyst for a time sufficient to convert the haloformate to the corresponding halide.

This invention relates to an improvement in the process of isolating certain diphenyl ethers from an aprotic organic solvent by the addition of a diphenyl ether phase forming amount of water to a reaction mixture comprising a liquid phase of the diphenyl ether dissolved in the solvent.

Process improvement for diphenyl ether production

Aromatic esters of carbamic acid derivatives, e.g., p-chlorophenyl-N-methyl carbamate, are prepared by reaction of the corresponding aromatic alcohol, e.g., p-chlorophenol, and monoisocyanate, e.g., methyl isocyanate, in the presence of a catalytic amount of a combination of a 4-aminopyridine catalyst, e.g., 4-dimethylaminopyridine, and pyridine or methyl substituted pyridines. The product is substantially pure, having less than 0.80 weight percent allophanate ester by-product, e.g., p-chlorophenyl-N,N'-dimethyl allophanate, and less than 0.50 weight percent unreacted aromatic alcohol, e.g., p-chlorophenol. The reaction is readily controlled and characterized by the substantial absence of reflux. The product can be retained in the liquid state at reaction temperature for extended periods of time without significantly increasing the level of allophanate ester by-product.

Catalyst system for manufacturing p-chlorophenyl-N-methyl carbamate

Dialkyl peroxydicarbonates are prepared in aqueous reaction media, washed with water, and then dried with sodium sulfate, calcium chloride, or the like. Peroxydicarbonates, particularly heat-sensitive peroxydicarbonates, may be dried safely and more effectively with the use of molecular sieves by contacting substantially phase water free peroxydicarbonate with sieves. Contact between heat-sensitive peroxydicarbonate and sieves should be effected in a way that avoids abrupt, excessive warming of peroxydicarbonate.

Drying of dialkyl peroxydicarbonates

Methylchloroform formulations containing 1,3-dioxolanes and/or 1,4-dioxane are storage-stabilized by the addition of aliphatic aldehyde hydrazone.

Storage stabilized methylchloroform formulations

Sulfonyl peroxides represented by the formula ##STR1## wherein R and R' independently are alkyl, cycloalkyl, or substituted alkyl or cycloalkyl groups having 1 to 20 carbons, are prepared in a liquid reaction phase by the sulfoxidation of an alkane or cycloalkane reactant with SO.sub.2 and O.sub.2 and acylation of the sulfoxidation product with a carboxylic acid anhydride. In the practice of this invention, an inert, immiscible organic solvent for the sulfonyl peroxide is introduced into the liquid reaction phase to dissolve the peroxide as it is formed and to produce a lower crude product phase containing the sulfonyl peroxide already dissolved in the inert solvent.

Synthesis of sulfonyl peroxides

Ethylenically unsaturated material susceptible to free-radical polymerization, e.g., vinyl chloride monomer, is polymerized, e.g., in an aqueous medium, with an initiator system comprising, in combination, alkaline reagent, e.g., sodium bicarbonate, organic acid anhydride, e.g., isobutyric anhydride, peroxygen compound selected from organic peroxy acid (peracid), e.g., peracetic acid, and hydrogen peroxide, and alkyl pyrocarbonate, e.g., diethyl pyrocarbonate. The initiator system is added to the polymerization medium in amounts sufficient to polymerize the ethylenically unsaturated material.

Polymerization of ethylenically unsaturated monomer employing a catalyst

Ethylenically unsaturated material susceptible to free-radical polymerization, e.g., vinyl chloride monomer, is polymerized, e.g., in an aqueous medium, with an initiator system comprising, in combination, alkaline buffering reagent, e.g., sodium bicarbonate, organic acid anhydride, e.g., isobutyric anhydride, peroxygen compound selected from organic peroxy acid (peracid), e.g., peracetic acid, and hydrogen peroxide, and alkyl haloformate, e.g., ethyl chloroformate. The initiator system is added to the polymerization medium to form the initiator(s) in situ.

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Akron, OH, United States of America

James A Manner