The Dow Chemical Company

Micromidas, Inc.

Origin Materials Operating, Inc.

James H Plonka

Makoto Nathanael Masuno

Ryan L Smith

John Bissell

Alex Benjamin Wood

Daniel Randolph Henton

Dimitri A Hirsch-Weil

Robert Joseph Araiza

R Garth Pews

Ralph A Davis

Dimitri A Hirsch-weil

The present disclosure provides methods to produce 5-(halomethyl)furfural, including 5-(chloromethyl)furfural, by acid-catalyzed conversion of C6 saccharides, including isomers thereof, polymers thereof, and certain derivatives thereof. The methods make use of acids with lower concentrations, and allows for conversion of sugars into 5-(halomethyl)furfural at higher temperatures and faster reaction or residence times.

Methods for producing 5-(halomethyl)furfural

A new process for preparing .gamma.-halonitriles comprising reacting by contacting a 1,3-dihalopropane, such as 1-chloro-3-bromopropane, or mixtures thereof, such as 1-chloro-3-bromopropane and 1-chloro-3-iodopropane, with an alkali metal cyanide, such a sodium cyanide, in the presence of an onium salt, such as benzyltriethylammonium chloride, and an alkali metal halide, such as sodium chloride. The .gamma.-halonitriles are useful in preparing cyclopropylcyanide, a herbicide intermediate.

Process for production of .gamma.-halonitriles

Cyclopropylcyanide is prepared by an improved process comprising reacting by contacting a .gamma.-halo-butyronitrile or mixture thereof, with an alkali metal hydroxide in the presence of a catalytic amount of an onium salt. For example, the reaction of 4-chlorobutyronitrile with sodium hydroxide in the presence of benzyltriethylammonium chloride produces cyclopropylcyanide in high yield.

Process for production of cyclopropylcyanide

Growing community of inventors

Midland, MI, United States of America

James H Plonka