Process for the preparation of Diels-Alder adducts of halogenated cyclopentadienes
AssigneeHooker Chemicals & Plastics Corporation
InventorDonald H. Thorpe
Life of this patent
Estimating the term…
Abstract
An improved process for the preparation of solid Diels-Alder adducts of halogenated cyclopentadienes and mono- or diolefins is disclosed wherein the reactants are combined in an aqueous emulsion. The adducts are obtained in excellent yield and in an extremely fine particulate form. The new process avoids the use of organic solvents which are relatively costly, hazardous to use, and from which the adducts are usually obtained as relatively large crystals which require pulverization prior to use.
Claims16
In a process for the preparation of a Diels-Alder adduct by carrying out the Diels-Alder reaction of a halogenated cyclopentadiene, wherein the carbon atoms of the carbon-to-carbon double bonds are perhalogenated, with a mono-olefin or diolefin capable of reacting with said halogenated cyclopentadiene to form a solid adduct, the improvement which comprises carrying out the adduction reaction with the reactants emulsified in an aqueous reaction medium employing about 0.9 to about 2.2 mole of the halogenated cyclopentadiene per mole of the olefin, the proportion of the halogenated cyclopentadiene and olefin reactants in said aqueous emulsion being about 10 to about 60 weight percent of the emulsion and the reaction temperature being about 20.degree. Centigrade to about 160.degree. Centigrade to obtain the solid adduct in particulate form having substantially no particles with a maximum size greater than about 200 microns.
In a process for the preparation of a Diels-Alder adduct by reacting hexachlorocyclopentadiene and 1,5-cyclooctadiene, the improvement which comprises
- 1. emulsifying the reactants in water in the proportion of about 10 to about 60 weight percent of the reactants based on the weight of the aqueous emulsion, employing about 1.8 to about 2.2 moles of hexachlorocyclopentadiene per mole of 1,5-cyclooctadiene in the presence of a small effective amount of an organic emulsifying agent,
- 2. reacting the hexachlorocyclopentadiene and 1,5-cyclooctadiene at a temperature in the range of about 20.degree. Centigrade to about 160.degree. Centigrade to form a solid adduct in particulate form having substantially no particles with a maximum size greater than about 200 microns, and,
- 3. recovering said adduct as a product of the process.
In the process for the preparation of a Diels-Alder adduct by carrying out the Diels-Alder reaction of a halogenated cyclopentadiene, wherein the carbon atoms of the carbon-to-carbon double bonds are perhalogenated, with a mono-olefin or diolefin capable of reacting with said cyclopentadiene to form an adduct which is a solid at least at temperatures up to about 160.degree. Centigrade, the improvement which comprises:
- 1. forming an emulsion of the reactants in water in the presence of an organic emulsifying agent wherein the emulsion comprises about 10 to about 60 weight percent of said reactants based on the total weight of the emulsion, the emulsifying agent is employed in a proportion of about 0.1 to about 10 weight percent based on the weight of said reactants, with the amount of the halogenated cyclopentadiene employed being about 0.9 to about 2.2 mole per mole of said olefin;
- 2. reacting said reactants at a temperature in the range of about 20.degree. Centigrade to about 160.degree. Centigrade to form the solid adduct in particulate form having substantially no particles with a maximum size greater than about 200 microns, and,
- 3. recovering said adduct as a product of the process.
Dependencies are inferred from the claim text.