Bioplastics, monomers thereof, and processes for the preparation thereof from agricultural feedstocks
OwnerSuresh Narine, Peter Sporns +1inventors
InventorsSuresh Narine, Peter Sporns, Jin Yue
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Abstract
The present invention relates generally to polymers and monomers derived from agricultural feedstocks, and more particularly to methods for the production of monomers from renewable agricultural resources such as feedstocks, for example canola, flax and tallow, and polymers, in particular polyurethanes produced from monomers derived from such feedstocks. The present invention also relates to novel processes for the production of short-chain alcohols, as well as hydroxyl wax esters, from renewable feedstocks. An improved apparatus for carrying out ozonolysis reactions is also disclosed.
Claims40
A method for producing a polyol from a renewable feedstock comprising one or more unsaturated fatty acid triacylglycerols, wherein the method comprises the steps of:
- a. ozonolysis of two or more double bonds in the unsaturated fatty acids of the one or more triacylglycerols of the feedstock under conditions effective to afford two or more corresponding ozonide functionalities;
- b. subjecting the products of step (a) to reductive hydrogenation under conditions effective to produce one or more corresponding polyols,
- wherein the one or more polyols comprise at least one triacylglycerol containing at least two primary hydroxyl groups.
A method for producing nonanol, hexanol, propanol, and/or 1,3-propanediol from a renewable feedstock comprising a fatty acid triacylglycerol having at least one unsaturated fatty acid chain, the method comprising the steps of:
- a. ozonolysis of the double bonds in the fatty acid chain of the triacylglycerol of the feedstock;
- b. subjecting the products of step (a) to reductive hydrogenation to produce nonanol, hexanol, propanol, and/or 1,3-propanediol;
- and
- c. separating nonanol, hexanol, propanol, and/or 1,3-propanediol from the products of step (b) by wiped-blade molecular distillation.
A method for the production of a hydroxyl wax ester from a renewable feedstock comprising one or more unsaturated fatty acid triacylglycerols, wherein the method comprises the steps of:
- a. ozonolysis of the double bonds in the unsaturated fatty acids of the one or more triacylglycerols of the feedstock;
- b. subjecting the products of step (a) to reductive hydrogenation to produce at least one of a corresponding mono-ol, at least one of a corresponding polyol, or a mixture thereof, in the presence of a short chain alcohol;
- wherein the at least one mono-ol, the at least one polyol, or the mixture thereof, comprises a triacylglycerol containing at least one terminal hydroxyl group, and wherein the reaction conditions are sufficient to afford transesterification between the triacylglycerol containing at least one terminal hydroxyl group and the short chain alcohol, thereby affording said hydroxyl wax ester.
An improved apparatus for carrying out ozonolysis reactions, said improvement comprising:
- a longitudinally disposed agitator operatively connected to a motor, said longitudinally disposed agitator comprising a plurality of pitched blades,
- wherein said longitudinally disposed agitator extends downwardly into a reaction vessel having an upper and a lower end,
- said reaction vessel comprising an ozone inlet channel disposed at the lower end and extending across the diameter of said reaction vessel,
- said ozone inlet channel having two apertures for ozone input at opposing ends thereof and a plurality of pores for release of ozone into said reaction vessel.
A method for the production of a hydroxyl wax ester from a renewable feedstock comprising one or more unsaturated fatty acid triacylglycerols, wherein the method comprises the steps of:
- a. ozonolysis of the double bonds in the unsaturated fatty acids of the one or more triacylglycerols of the feedstock;
- b. subjecting the products of step (a) to reductive hydrogenation to produce at least one corresponding mono-ol, at least one corresponding polyol, or a mixture thereof, wherein the at least one mono-ol, the at least one polyol, or the mixture thereof comprises a triacylglycerol containing at least one terminal hydroxyl group;
- and
- c. subjecting the products of step (b) to transesterification with a short chain alcohol to produce said hydroxyl wax ester.
A compound having the formula:
- wherein said compound is isolated in substantially pure form.
Dependencies are inferred from the claim text.