The present invention relates to monoterpenoid and phenylpropanoid containing derivative compounds, methods of making the compounds, compositions comprising the compounds, and methods of repelling pests using the compounds and/or compositions.

The present invention relates to monoterpenoid and phenylpropanoid containing derivative compounds, methods of making the compounds, compositions comprising the compounds, and methods of repelling pests using the compounds and/or compositions.

The present invention is a process for preparing a sorbate ester comprising the steps of: a) contacting together in a reaction vessel a first organic solvent, sorbic acid, a catalytic amount of TiC14, an anti-oxidant, and an alkylene oxide under conditions sufficient to form a mixture of the sorbate ester and residual water-soluble impurities; then b) separating the sorbate ester from the residual water-soluble impurities by washing. Sorbate esters can be prepared in an efficient and cost-effective manner by the process of the present invention.

The present invention is a process for preparing a sorbate ester comprising the steps of: a) contacting together in a reaction vessel a first organic solvent, sorbic acid, a catalytic amount of TiC14, an anti-oxidant, and an alkylene oxide under conditions sufficient to form a mixture of the sorbate ester and residual water-soluble impurities; then b) separating the sorbate ester from the residual water-soluble impurities by washing. Sorbate esters can be prepared in an efficient and cost-effective manner by the process of the present invention.

The present invention is a process for preparing a sorbate ester comprising the steps of: a) contacting together in a reaction vessel a first organic solvent, sorbic acid, a catalytic amount of TiC14, an anti-oxidant, and an alkylene oxide under conditions sufficient to form a mixture of the sorbate ester and residual water-soluble impurities; then b) separating the sorbate ester from the residual water-soluble impurities by washing. Sorbate esters can be prepared in an efficient and cost-effective manner by the process of the present invention.

The present invention is a process for preparing a hydroxyalkyl sorbate comprising the steps of of: a) contacting together in a reaction vessel a solvent, sorbic acid, a transition metal halide catalyst, an anti-oxidant, and an alkylene oxide under conditions sufficient to form the hydroxyalkyl sorbate; b) removing the solvent in vacuo, wherein the anti-oxidant is characterized by the following formula or a carboxylic acid salt thereof:

##STR00001##

wherein Y, x, and R.sup.1 are defined herein. The process of the present invention provides a convenient way of preparing hydroxyalkyl sorbates in high yield and purity without complicated workup steps.

The present invention is a process for preparing a hydroxyalkyl sorbate comprising the steps of of: a) contacting together in a reaction vessel a solvent, sorbic acid, a transition metal halide catalyst, an anti-oxidant, and an alkylene oxide under conditions sufficient to form the hydroxyalkyl sorbate; b) removing the solvent in vacuo, wherein the anti-oxidant is characterized by the following formula or a carboxylic acid salt thereof:

##STR00001##

wherein Y, x, and R.sup.1 are defined herein. The process of the present invention provides a convenient way of preparing hydroxyalkyl sorbates in high yield and purity without complicated workup steps.

The present invention is a process for preparing a hydroxyalkyl sorbate comprising the steps of of: a) contacting together in a reaction vessel a solvent, sorbic acid, a transition metal halide catalyst, an anti-oxidant, and an alkylene oxide under conditions sufficient to form the hydroxyalkyl sorbate; b) removing the solvent in vacuo, wherein the anti-oxidant is characterized by the following formula or a carboxylic acid salt thereof:

##STR00001##

wherein Y, x, and R.sup.1 are defined herein. The process of the present invention provides a convenient way of preparing hydroxyalkyl sorbates in high yield and purity without complicated workup steps.

The present invention includes methods for producing and purifying esters of polyunsaturated fatty acids that include reacting a composition having triglycerides with polyunsaturated fatty acid residues in the presence of an alcohol and a base to produce an ester of a polyunsaturated fatty acid from the triglycerides. The composition can be a polyunsaturated fatty acid-containing composition that has not been conventionally processed. The reacted composition can be further processed by distillation.

The present invention includes methods for producing and purifying esters of polyunsaturated fatty acids that include reacting a composition having triglycerides with polyunsaturated fatty acid residues in the presence of an alcohol and a base to produce an ester of a polyunsaturated fatty acid from the triglycerides. The composition can be a polyunsaturated fatty acid-containing composition that has not been conventionally processed. The reacted composition can be further processed by distillation.