Unsaturated fatty alcohol derivatives from natural oil metathesis

US11760889B2 · kind B2 · utility

Assignee

• STEPAN COMPANY · US

Inventors

• David R. Allen · Chicago, US
• Marcos Alonso · Chicago, US
• Mary Beddaoui · Glenview, US
• Randal J. Bernhardt · Antioch, US
• Aaron Brown · Chicago, US
• Scott Dillavou · Skokie, US
• Xue Min Dong · Lincolnshire, US
• Wilma Gorman · Paddy Lane, US
• John C. Hutchison · Chicago, US
• Gary Luebke · Chicago, US
• Renee Luka · Paddy Lane, US
• Franz J. Luxem · Palatine, US
• Andrew D. Malec · Chicago, US
• Ronald A. Masters · Glenview, US
• Dennis S. Murphy · Wyckoff, US
• Nicholas Pendleton · Atlanta, US
• Irma Ryklin · Buffalo Grove, US
• Patti Skelton · Winder, US
• Brian Sook · Lawrenceville, US
• Chris Spaulding · Evanston, US
• Krista L. Turpin · Loganville, US
• Gregory Wallace · Chicago, US
• Michael Wiester · Chicago, US
• Patrick Shane Wolfe · Palatine, US

Key dates

• Filing date: Jul 15, 2020
• Grant date: Sep 19, 2023
• Expiry date: Jun 20, 2041

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61K2800/10
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

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 com…