Unsaturated fatty alcohol derivatives from natural oil metathesis

Patent metadata

Field	Value
Publication number	US-11760889-B2
Application number	US-202016929420-A
Country	US
Kind code	B2
Filing date	Jul 15, 2020
Priority date	Apr 24, 2012
Publication date	Sep 19, 2023
Grant date	Sep 19, 2023

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 compositions, latex paints, and specialty foams.

First claim

We claim:

1. A sulfate derivative having the general structure:
R—CH═CH—(CH 2 ) 7 —CH 2 O-(AO) n —SO 3 X

wherein R is a C 2 alkyl; X is a mono- or divalent cation or an ammonium or substituted ammonium cation; AO is an oxyalkylene group; and n, which is the average number of oxyalkylene groups, has a value within the range of 0 to 200,
wherein the sulfate derivative has at least 80 mole % of trans-Δ 9 unsaturation.

2. The sulfate derivative of claim 1 wherein n has a value within the range of 1 to 50.

3. The sulfate derivative of claim 1 wherein n has a value within the range of 1 to 20.

4. The sulfate derivative of claim 1 wherein AO is an oxyethylene group.

5. The sulfate derivative of claim 4 wherein n is 1, 3, 5, 7, or 15.

6. The sulfate derivative of claim 5 wherein X is Na + or NH 4 + .

7. An agricultural composition comprising a pesticide and the sulfate derivative of claim 1 .

8. An aqueous hard-surface cleaner comprising the sulfate derivative of claim 1 .

9. A personal cleanser comprising the sulfate derivative of claim 1 .

10. A light-duty liquid detergent comprising the sulfate derivative of claim 1 .

11. A laundry detergent comprising the sulfate derivative of claim 1 .

12. The sulfate derivative of claim 1 , made by sulfating or alkoxylating and sulfating a monounsaturated fatty alcohol composition, wherein the fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester.

13. The sulfate derivative of claim 1 wherein the trans-Δ 9 unsaturation is at least 90 mole %.

14. The sulfate derivative of claim 13 wherein the trans-Δ 9 unsaturation is at least 95 mole %.

15. The sulfate derivative of claim 14 wherein the trans-Δ 9 unsaturation is 100 mole %.

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

• C09D7/45 Primary

  Anti-settling agents · CPC title

• A01N25/30

  characterised by the surfactants · CPC title

• A61K8/463

  containing sulfuric acid derivatives, e.g. sodium lauryl sulfate · CPC title

• A61K8/466

  containing sulfonic acid derivatives; Salts · CPC title

• A61K2800/10

  General cosmetic use · CPC title