Stepan Company

Gregory Wallace

Randal J Bernhardt

Aaron Brown

Dennis S Murphy

Ronald Anthony Masters

Patrick Shane Wolfe

Andrew D Malec

Patti Skelton

Marcos Alonso

Renee Luka

Brian Sook

Michael Wiester

Gary R Luebke

Dave R Allen

Irene Shapiro

Michael R Terry

Laura Lee Whitlock

Brian Holland

Sangeeta Ganguly-Mink

Kelly Buchek

Lena Titievsky

Xue Min Dong

Irma Ryklin

Franz Josef Luxem

Wilma Gorman

David R Allen

John C Hutchison

Krista L Turpin

Nicholas Pendleton

Chris Spaulding

Mary Beddaoui

Scott Dillavou

Gary Luebke

Franz Luxem

Xue Dong

Krista Turpin

Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives. Microscopy studies indicate that the unsaturated sodium sulfates in particular have a lamellar phase that should enable formulation at high actives levels. Sulfate compositions comprising 40 to 60 wt. % of a monounsaturated fatty primary alcohol sulfate and 40 to 60 wt. % of a secondary hydroxyalkyl primary alcohol sulfate are also disclosed. The derivatives and sulfate compositions are valuable for many end-use applications, including, for example, agricultural dispersants, water-soluble herbicides, anionic emulsifiers for agricultural use, hard surface cleaners, light-duty liquid detergents, personal cleansers, gas well foamers for oilfield applications, laundry detergents, enhanced oil recovery compositions, latex paints, and specialty foams.

Unsaturated fatty alcohol derivatives from natural oil metathesis

Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives.

Fatty amide compositions and their derivatives are disclosed. The fatty amides comprise a reaction product of a metathesis-derived C-Cmonounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a primary or secondary amine. Derivatives made by reducing, quaternizing, sulfonating, alkoxylating, sulfating, and sulfitating the fatty amide are also included. The amine reactant can be diethylenetriamine or (2-aminoethyl)ethanolamine, which provide imidazoline amides or esters, respectively. In one aspect, the ester derivative of the C-Cmonounsaturated 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 compositions are valuable for cleaners, fabric treatment, hair conditioning, personal care, antimicrobial compositions, agricultural uses, and oil field applications.

Fatty amides and derivatives from natural oil metathesis

Imidazoline amides and derivitives from natural oil metathesis

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Chicago, IL, United States of America

Gregory Wallace