Sulfonates from natural oil metathesis

Patent metadata

Field	Value
Publication number	US-9598359-B2
Application number	US-201113880007-A
Country	US
Kind code	B2
Filing date	Oct 25, 2011
Priority date	Oct 25, 2010
Publication date	Mar 21, 2017
Grant date	Mar 21, 2017

Abstract

Sulfonate compositions are disclosed. The compositions include alkanesulfonates, alkenesulfonates, sultones, and hydroxy-substituted alkanesulfonates. The sulfonates comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a sulfonating or sulfitating agent. In one aspect, the sulfonate composition is a sulfo-estolide made by reacting a metathesis-derived C10-C17 monounsaturated acid or octadecene-1,18-dioic acid with a sulfonating agent, optionally in the presence of a saturated fatty acid. The sulfonates 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), paint additives, antimicrobial compositions, agricultural uses, and oil field applications.

First claim

We claim:

1. A composition comprising a mixture of:
a β-hydroxy-substituted alkanesulfonate
and
an alkenesulfonate;
wherein the composition has the structure:

2. A sulfo-estolide having
a structure selected from the group consisting of:

3. An anionic emulsifier for agricultural compositions, a water-soluble herbicide composition, an aqueous hard-surface cleaner, a paraffin dispersant for oilfield applications, or a paint or coating additive composition comprising the composition of claim 1 .

4. An anionic emulsifier for agricultural compositions, a water-soluble herbicide composition, an aqueous hard-surface cleaner, a paraffin dispersant for oilfield applications, or a paint or coating additive composition comprising the composition of claim 2 .

5. A sulfonate composition having the structure:

6. An anionic emulsifier for agricultural compositions, a water-soluble herbicide composition, an aqueous hard-surface cleaner, a paraffin dispersant for oilfield applications, or a paint or coating additive composition comprising the sulfonate composition of claim 5 .

7. A sulfo-estolide having the structure:

8. An anionic emulsifier for agricultural compositions, a water-soluble herbicide composition, an aqueous hard-surface cleaner, a paraffin dispersant for oilfield applications, or a paint or coating additive composition comprising the sulfo-estolide of claim 7 .

Assignees

• Allen Dave R
• Bernhardt Randal J
• Brown Aaron
• Luebke Gary
• Luka Renee
• Malec Andrew D
• Masters Ronald A
• Skelton Patti
• Sook Brian
• Weitgenant Jeremy Aaron
• Wolfe Patrick Shane
• Stepan Co

Inventors

• Allen Dave R
• Bernhardt Randal J
• Brown Aaron
• Luebke Gary
• Luka Renee
• Malec Andrew D
• Masters Ronald A
• Skelton Patti
• Sook Brian
• Weitgenant Jeremy Aaron
• Wolfe Patrick Shane

Classifications

• C07C309/17

  containing carboxyl groups bound to the carbon skeleton · CPC title

• C11D1/143

  Sulfonic acid esters · CPC title

• C07C303/32 Primary

  of salts of sulfonic acids · CPC title

• C09K23/00

  Use of substances as emulsifying, wetting, dispersing, or foam-producing agents · CPC title

• C11C3/08

  with fatty acids · CPC title