Unsaturated fatty alcohol derivatives from natural oil metathesis

Patent metadata

Field	Value
Publication number	US-10745347-B2
Application number	US-201314395835-A
Country	US
Kind code	B2
Filing date	Mar 13, 2013
Priority date	Apr 24, 2012
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

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.

First claim

We claim:

1. A sulfate composition comprising:
(a) 40 to 60 wt. % of a monounsaturated C 10 or C 12 primary alcohol sulfate of the formula

(b) 40 to 60 wt. % of a C 10 or C 12 secondary hydroxyalkyl primary alcohol sulfate of the formula

and
(c) 0.1 to 20 wt. % of sulfonated products;
wherein X in each formula is a mono- or divalent cation or an ammonium or substituted ammonium cation;
wherein the sulfate composition is made by falling-film sulfation using sulfur trioxide of a C 10 or C 12 monounsaturated primary alcohol of the formula

and
wherein cross-polarized light microscopy examination at 100× to 400× and 20-22° C. of aqueous mixtures comprising the sulfate composition reveals an isotropic clear phase at all actives levels up to 50 wt. % actives.

2. The sulfate composition of claim 1 comprising 45 to 55 wt. % of the monounsaturated C 10 or C 12 primary alcohol sulfate and 45 to 55 wt. % of the C 10 or C 12 secondary hydroxyalkyl primary alcohol sulfate.

3. The sulfate composition of claim 1 comprising 0.5 to 15 wt. % of sulfonated products.

4. The sulfate composition of claim 1 wherein the microscopy examination reveals a lamellar phase at actives levels within the range of 65 to 80 wt. % actives.

5. A dispersant for agricultural compositions comprising the sulfate composition of claim 1 .

Assignees

• Stepan Co

Inventors

• Allen David R
• Alonso Marcos
• Beddaoui Mary
• Bernhardt Randal J
• Brown Aaron
• Dillavou Scott
• Dong Xue Min
• Gorman Wilma
• Hutchison John C
• Luebke Gary
• Luka Renee
• Luxem Franz
• Malec Andrew D
• Masters Ronald A
• Murphy Dennis S
• Pendleton Nicholas
• Ryklin Irma
• Skelton Patti
• Sook Brian
• Spaulding Chris
• Turpin Krista
• Wallace Gregory
• Wiester Michael
• Wolfe Patrick Shane

Classifications

• C09K23/018

  Mixtures of two or more different organic oxygen-containing compounds · CPC title

• C09D7/63

  organic · CPC title

• A61K8/466

  containing sulfonic acid derivatives; Salts · CPC title

• C11D1/143

  Sulfonic acid esters · CPC title

• C04B38/10

  by using foaming agents (C04B38/02 takes precedence){or by using mechanical means, e.g. adding preformed foam} · CPC title