In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I

##STR00001##

with a metathesis reaction partner according to Formula IIb

##STR00002##

in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb:

##STR00003##

and
b) converting the metathesis product to the fatty olefin derivative. Each R.sup.1 is independently selected from H, C.sub.1-18 alkyl, and C.sub.2-18 alkenyl; R.sup.2b is C.sub.1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.

In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I

##STR00001##

with a metathesis reaction partner according to Formula IIb

##STR00002##

in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb:

##STR00003##

and
b) converting the metathesis product to the fatty olefin derivative. Each R.sup.1 is independently selected from H, C.sub.1-18 alkyl, and C.sub.2-18 alkenyl; R.sup.2b is C.sub.1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.

The present invention relates to esters of at least one polyol and of a mixture of fatty acids comprising at least one C.sub.5-C.sub.12 saturated fatty acid and at least one C.sub.10-C.sub.12 unsaturated fatty acid.

Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amines, wherein the fatty amine is made by reducing the amide reaction product of a metathesis-derived C.sub.10-C.sub.17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and a secondary amine, are disclosed. Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amidoamines, wherein the amidoamine is made by reacting of a metathesis-derived C.sub.10-C.sub.17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and an aminoalkyl-substituted tertiary amine, are also disclosed. The quaternized compositions are advantageously sulfonated or sulfitated. In one aspect, the ester derivative of the C.sub.10-C.sub.17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The quaternary ammonium, betaine, and sulfobetaine compositions and their sulfonated or sulfitated derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.

Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amines, wherein the fatty amine is made by reducing the amide reaction product of a metathesis-derived C.sub.10-C.sub.17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and a secondary amine, are disclosed. Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amidoamines, wherein the amidoamine is made by reacting of a metathesis-derived C.sub.10-C.sub.17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and an aminoalkyl-substituted tertiary amine, are also disclosed. The quaternized compositions are advantageously sulfonated or sulfitated. In one aspect, the ester derivative of the C.sub.10-C.sub.17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The quaternary ammonium, betaine, and sulfobetaine compositions and their sulfonated or sulfitated derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.

Methods of making branched isoparaffin compositions derived from natural oil based linear internal olefins are disclosed. Uses of branched isoparaffins formed by such methods are also disclosed.

Methods of making branched isoparaffin compositions derived from natural oil based linear internal olefins are disclosed. Uses of branched isoparaffins formed by such methods are also disclosed.

Disclosed herein is an ophthalmic formulation comprising a compound of formula (I) wherein le is a linear or branched C.sub.9-C.sub.33 alkyl or a linear or branched C.sub.9-C.sub.33 alkenyl with 1 to 4 double bonds; R.sup.2 is a linear or branched C.sub.9-C.sub.19 alkyl or a linear or branched C.sub.9-C.sub.19 alkenyl with 1 to 4 double bonds; and an ophthalmologically acceptable carrier.

Disclosed herein is an ophthalmic formulation comprising a compound of formula (I) wherein le is a linear or branched C.sub.9-C.sub.33 alkyl or a linear or branched C.sub.9-C.sub.33 alkenyl with 1 to 4 double bonds; R.sup.2 is a linear or branched C.sub.9-C.sub.19 alkyl or a linear or branched C.sub.9-C.sub.19 alkenyl with 1 to 4 double bonds; and an ophthalmologically acceptable carrier.

Biodegradable surfactants are described, in which an amphiphilic heteroatom containing hydrocarbon optionally comprising at least one counterion (Z), and related compositions, methods and systems. Biodegradable surfactant described herein has an aHLB value in accordance with equation (1): aHLB=20*Gh/(Gh−Gt) (1) wherein Gh is the Group Number of a hydrophilic head portion of the biodegradable surfactant optionally comprising the at least one counterion (Z), and Gt is the Group Number of a hydrophobic tail portion of the biodegradable surfactant. A biodegradable surfactant in the sense of the disclosure can be tuned to a set hydrophilic-lipophilic balance (aHLB) by selectively modifying at least one tuning moiety of the biodegradable surfactants to provide tuned biodegradable surfactants having an increase or decrease in their adjusted hydrophilic-lipophilic balance (aHLB).