Monsanto Company

Manuel M Baizer

Richard C Hallcher

Richard D Goodin

Thomas Edward Rogers

Donald A White

Robert E Jansson

Electrolytic processes in which separate useful reactions are conducted at an anode and cathode, respectively, by electrolysis of an anolyte at an anode and a catholyte at the cathode wherein the anolyte and catholyte are of different composition and are prevented from contacting the cathode and anode, respectively, during electrolysis without the use of selective permeable membranes or permeable partitions.

Electrolysis cells and electrolytic processes

The invention relates to the process for making glyoxylate hemiacetals comprising reacting an alcohol of the formula ROH where R is alkyl, or reacting a formate ester of the formula ##STR1## where R is alkyl, with CO under pressure in the presence of a basic initiator of the formula M.sup.+ (OR).sup.- where M is an alkali metal and R is alkyl, and in the presence of a complexing agent for M.sup.+ having O and/or N donor atoms capable of solvating M.sup.+ or in the presence of a basic initiator of the formula NR'.sub.4.sup.+ (OR).sup.- where each R' is the same or a different alkyl or aralkyl and R is alkyl.

Process for making glyoxylate hemiacetals

The invention is a process for alkylating nitriles using an electrogenerated base and an alkylating agent comprising (a) electro-reducing an azobenzene probase at a cathode in an electrolysis medium comprising the azobenzene probase, a nitrile and a supporting electrolyte to produce an electrogenerated base, (b) deprotonating the nitrile with the electrogenerated base to produce a nitrile anion, and (c) reacting the nitrile anion with alkylating agent to form alkylated nitrile; the probase being more easily electro-reducible than the nitrile and producing an electrogenerated base strong enough to deprotonate the nitrile which is sufficiently acidic to permit such deprotonation, and the electrogenerated base not reacting readily, unless rapidly reversibly, with the alkylating agent.

Alkylation of nitriles using an electrogenerated base and an alkylating

The invention is a process for using certain electrogenerated bases in reactions such as acetoacetic ester condensations wherein an azobenzene probase is electro-reduced to produce an electrogenerated base, acetic ester is deprotonated by electrogenerated base to produce an anion, and the anion is condensed with acetic ester to produce acetoacetic ester condensation product; the probase being more easily electro-reducible than the acetic ester and producing an electrogenerated base strong enough to deprotonate the acetic ester which is sufficiently acidic to permit such deprotonation. The probase can be regenerated, either directly or indirectly, by anodic oxidation to probase making the reaction catalytic.

Use of electrogenerated bases in condensation reactions

The invention is a process for alkylating nitrogen acids using an electrogenerated base as a catalyst comprising (a) electro-reducing a probase at the cathode by electrolysis in an aprotic liquid electrolysis medium comprising a probase, an anhydrous aprotic solvent, and supporting electrolyte to produce an electrogenerated base, (b) deprotonating a nitrogen acid with the electrogenerated base to produce a nitrogen acid anion, and (c) reacting the nitrogen acid anion with an alkylating agent to produce an alkylated nitrogen acid; with the aforesaid probase being more easily electro-reducible than the nitrogen acid and producing an electrogenerated base strong enough to deprotonate the nitrogen acid which is sufficiently acidic to permit such deprotonation, and the electrogenerated base not reacting readily, unless rapidly reversibly, with the alkylating agent.

Alkylating of nitrogen acids using electrogenerated bases as catalysts

The invention is a process for anionically polymerizing vinyl monomers comprising contacting a vinyl monomer with an electrolytically reduced graphite having formed therein a Graphite R.sub.4 N.sup.+ intercalation compound wherein Graphite is a graphite anion radical and each R is alkyl, preferably alkyl having not more than 8 carbon atoms, to form vinyl polymer. The reduced graphite for polymerizing the vinyl monomers is prepared by electrochemical reduction of a graphite cathode in a polar aprotic solvent containing a quaternary ammonium salt electrolyte to form a graphite anion associated with a quaternary ammonium cation intercalated in the graphite. When the electrolysis is completed the graphite cathode is removed from the electrolysis cell, rinsed and contacted with vinyl monomer either dissolved in a solvent or neat to cause the polymer formation.

Initiation of anionic polymerization of vinyl monomers by reduced

Organic electrophiles are added to carbon acids via catalysis by electrogenerated bases to yield carbon acid-organic electrophile addition products.

Addition of organic electrophiles to carbon acids via catalysis by

Cresol salts substituted with non-interfering, blocking substituents at least at the 2,4,6-positions relative to the phenolic oxyanion where at least one of the substituents is the cresolic methyl are electrolytically oxidized to yield methyl-methyl coupled dehydrodimeric cresols.

Process for electrolytic oxidative methyl-methyl coupling of cresol salts

Electrolytic carboxylation of carbon acids via electrogenerated bases leads to carboxylated carbon acids.

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Santa Monica, CA, United States of America

Manuel M Baizer