Monsanto Company

Richard C Hallcher

James P Coleman

Dudley E McMackins

Manuel M Baizer

Richard D Goodin

Thomas Edward Rogers

Steven R Auvil

Donald A White

Zane V Zeable

Charles R Penquite

Wayne D Wimbish

Apparatus and methods for removing silver and copper ions from purge streams from silver replacement processes by separately electrowinning silver and copper where silver removal is first effected in an electrowinning cell having a cathode/calomel reference electrode potential between -0.1 and -0.4 volts DC followed by copper removal effected in an electrowinning cell having a cathode/calomel reference electrode potential less than -0.5 volts DC. By this method formation of copper (+1) is prevented in the presence of high concentrations of silver, thus minimizing precipitation of silver metal and formation of copper (+2).

Silver bath waste treatment apparatus and method

Preparation of sorbic acid from precursors by contact with acid catalysts is improved by utilizing crystallization to separate sorbic acid during the preparation.

Sorbic acid process with crystallization

Butadiene and acetic acid are reacted with metal ion oxidant to prepare acetoxyhexenoic acids which are then converted to sorbic acid.

Sorbic acid process

This disclosure concerns acyloxyhexenoic acids and their salts with the acids being produced by reaction of butadiene and acetic acid with metal salt oxidants in a process involving electrolytic regeneration of the metal oxidants during the reaction. Iosmeric acetoxyhexenoic acids produced can be readily converted to sorbic acid, and antimicrobial and preservative uses for the acids are also disclosed.

Acyloxyalkenoic acids and process therefor

Perfluoroalkanoic acids and perfluoroalkanols are prepared by electrolysis of perfluoroalkyl chlorides in the presence of carbon dioxide or an aldehyde, for example, trifluoroacetic acid is obtained from chlorotrifluoromethane and carbon dioxide while trifluoroethanol is obtained from chlorotrifluoromethane and formaldehyde.

Electrolytic preparation of perfluoroalkanoic acids, perfluoroalkanols

Butadiene and acetic acid are reacted with a metal salt oxidant in molten salt medium to form .gamma.-vinyl-.gamma.-butyrolactone. The process includes electrolytic regeneration of the oxidant and provides a simple reaction system which permits product recovery and reactant recycle without extensive solvent handling. A high surface area reactor can be employed.

Production of lactone in molten salt electrolysis

In the process of preparing acetoxyhexenoic acids from butadiene, acetic acid and acetic anhydride, selectivity is improved by converting the acetoxyhexenoic acids to .gamma.-vinyl-.gamma.-butyrolactone before isolation. Copper and platinum are useful catalysts in the conversion.

Synthesis of .gamma.-vinyl-.gamma.-butyrolactone from acetoxyhexenoic

The acid conversion of certain precursors, e.g. .gamma.-vinyl-.gamma.-butyrolactone, to sorbic acid is improved by presence of copper or silver ions along with the acid.

Metal and acid catalysis in sorbic acid preparation

Acyloxyhexenoic acids are converted to .gamma.-vinyl-.gamma.-butyrolactone.

Lactone process

Acyloxyhexenoic acids are produced by reaction of butadiene and acetic acid with metal salt oxidants in a process involving electrolytic regeneration of the metal oxidants during the reaction.

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

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

Electrolytic oxidation of 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 leads to methyl-methyl coupled dehydrodimeric cresols.

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Maryland Heights, MO, United States of America

Richard C Hallcher