Reilly Industries, Inc.

Reilly Tar and Chemical Corporation

Joseph E Toomey, Jr

A process for the selective chlorination of pyridine, a lower alkyl pyridine or 3-cyanopyridine includes passing the pyridine compound, chlorine and an inert gas through a two stage reaction. In a first reaction zone, these materials are subjected to a hot spot controlled at a temperature of about 350.degree. to about 500.degree. C. The materials are then subsequently passed through a second reaction zone at a relatively lower temperature, for example below about 340.degree. C.

Chlorination process

A preferred electrochemical process for producing an alcohol or carboxylic acid from a corresponding metal salt while also recovering metal cation residues is described. The preferred process does not require a three-compartment desalination cell but rather can be performed in a standard two-compartment cell divided by a cation-permeable membrane. The process comprises the step of electrolyzing an aqueous medium containing the metal salt in the anolyte of the cell to thereby yield alcohol or carboxylic acid in the anolyte and pass the metal cation into the catholyte. In one particularly preferred mode, the process provides a highly effective recovery of valuable materials from byproduct streams of base-catalyzed syntheses of polyols such as such as trimethylolpropane or pentaerythritol from aldehydes, and in another provides an efficient recovery of phenol.

Electro-synthesis of alcohols and carboxylic acids from corresponding

A process for the selective chlorination of pyridine or a lower alkyl pyridine includes passing the pyridine compound, chlorine and an inert gas through a two stage reaction. In a first reaction zone, these materials are subjected to a hot spot controlled at a temperature of about 350.degree. to about 500.degree. C. The materials are then subsequently passed through a second reaction zone at a relatively lower temperature, for example below about 340.degree. C.

A process in which an electrochemical cell is used to simultaneously conduct a product synthesis and purification while also regenerating conductive material. The improved process is applied to an electrochemical synthesis which is conducted by electrolyzing a working electrolyte into which ions selectively flow, as through an ion-exchange membrane, from a counter electrolyte. The improvement comprises the step of purifying a previously electrolyzed working electrolyte by including it in or as a counter electrolyte in a subsequent synthesis.

Electrochemical synthesis and simultaneous purification process

An electrochemical oxidation of a pi-deficient N-heterocyclic precursor compound having an oxidizable organic group attached by a carbon-to-carbon linkage. This precursor compound is at least sparingly water soluble. The preferred electro-oxidation is conducted at an effective anode and in a medium which consists essentially of water, carboxylic acid, and the precursor compound. Preferred are electro-oxidations of substituted pyridine and quinoline bases and a particularly preferred aspect provides a convenient electrochemical synthesis of niacin from 3-methylpyridine.

Electrochemical synthesis of niacin and other N-heterocyclic compounds

Electrochemical reductions of pyridine carboxamide bases performed by electrolysis in a divided flow cell utilizing an ion-exchange membrane at a high hydrogen-overvoltage cathode and in an aqueous or partly aqueous medium comprising a Lowry-Bronsted acid in at least a 1:1 equivalent ratio with the pyridine carboxamide base. A titanium salt catalyst and other means are disclosed to add selectivity to the reduction and improve yield of the amine or other desired reaction product. With all bases, significant advantages of a commercial and industrial nature are reported over prior art static, beaker cell technology.

Electrochemical reduction of pyridine carboxamide bases

An improved electrochemical dimerization of a N-substituted pyridinium salt to its corresponding N,N'-disubstituted 4,4'-tetrahydrobipyridine in a flow cell at a high-surface-area cathode, employing an ion-exchange membrane divider and an alkaline catholyte solution. Isolation and recovery of the resultant product are reported in significant yields are reported without the use of an extracting solvent or corrosion or other additive either in the catholyte solution or in any subsequent operation.

Electrochemical dimerizations of pyridinium salts

A filter press electrochemical cell with an improved fluid distribution system for even distribution of electrolyte between cell units when connected in parallel, and from side to side and across the thickness of reaction chambers in individual cells regardless of whether parallel or series flow connection is used. Each preferred cell unit comprises two electrodes and a fluid distributor plate having at least two first holes therein and channel portions including diverging walls connecting these holes with opposite sides of a central cell opening in each plate. Preferred configurations of the triangular-shaped channel opening thereby formed permit distribution of fluid without complicating barrier structures or other constrictions in the fluid path such as used in prior art cells. Preferred and alternate cell arrangements and configurations are disclosed.

Filter press electrochemical cell with improved fluid distribution system

Improved electrochemical oxidations of alkylpyridine bases in which the oxidation is performed by electrolysis in a membrane divided flow cell at a lead dioxide anode and in an aqueous medium comprising sulfuric acid in at least a 1:1 equivalent ratio with the alkylpyridine base in solution. Significant advantages of a commercial and industrial nature are reported over prior static, beaker cell technology.

Electrochemical oxidation of pyridine bases

Improved electrochemical reductions of cyanopyridine bases in which the reduction is performed by electrolysis in an ion-exchange membrane-divided flow cell at a lead dioxide cathode and in an aqueous or partly aqueous medium comprising sulfuric acid in at least a 1:1 mole ratio with the cyanopyridine base. In the case of 2- and 3- isomers, an iron salt is also added to the catholyte as a catalyst. In the case of the 4- isomer, an efficient, semi-continuous batch process is reported. With all bases, significant advantages of a commercial and industrial nature are reported over prior art static, beaker cell technology.

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Indianapolis, IN, United States of America

Joseph E Toomey, Jr