Processes And Systems For Catalytic Manufacture Of Wax Ester Derivatives

Patent No. US11248245 (titled "Processes And Systems For Catalytic Manufacture Of Wax Ester Derivatives") was filed by Cargill Inc on Dec 19, 2014.

What is this patent about?

’245 is related to the field of transesterification of wax esters , specifically addressing the modification of wax esters derived from natural sources like jojoba oil. Wax esters, formed from fatty acids and fatty alcohols, are used in cosmetics and personal care products. Conventional transesterification methods, which alter the physical properties of these esters, often rely on chemical catalysts, leading to undesirable side reactions and degradation of beneficial components present in the original feedstock.

The underlying idea behind ’245 is to use enzymatic catalysis, specifically with lipases , to transesterify wax esters. This approach avoids the harsh conditions and side reactions associated with chemical catalysts. By using lipases, the process can be carried out at lower temperatures and ambient pressure, preserving valuable components like antioxidants, sterols, and volatile compounds naturally present in the wax ester feedstock, such as jojoba oil.

The claims of ’245 focus on a process involving a feedstock containing both jojoba wax esters and hydrogenated jojoba wax esters, where the hydrogenated portion constitutes 20% to 50% of the feedstock by weight. The feedstock is then contacted with a lipase to facilitate transesterification, resulting in a product with an improved oxidative stability index (OSI) compared to the original feedstock. This improvement in OSI is a key feature.

In practice, the enzymatic transesterification can be performed in a continuous reactor system, where the wax ester feedstock flows through one or more reactors containing immobilized lipases. This continuous process offers advantages over batch processing. The use of lipases allows for a more selective reaction, avoiding the formation of unwanted byproducts like methyl esters and free fatty alcohols, which can alter the desired properties of the final product. Furthermore, the process preserves the natural antioxidants present in the jojoba oil, contributing to the enhanced oxidative stability.

The enzymatic approach differentiates itself from traditional chemical methods by maintaining the integrity of the feedstock's natural components. While chemical transesterification often degrades or removes beneficial compounds, the lipase-catalyzed process preserves these elements, leading to a transesterified product with improved properties. Surprisingly, the OSI of the transesterified product is not only maintained but often increased, suggesting a synergistic effect of the enzymatic process. This results in a product with enhanced shelf life and performance characteristics, particularly in cosmetic and personal care applications.

How does this patent fit in bigger picture?

Technical landscape at the time

In the mid-2010s when ’245 was filed, chemical and enzymatic processes were commonly used for modifying fats, oils, and waxes. At a time when transesterification was typically implemented using chemical catalysts, enzymatic methods offered advantages such as milder reaction conditions and reduced byproduct formation. When hardware or software constraints made precise control of reaction parameters non-trivial, techniques for optimizing enzyme activity and stability were of interest.

Novelty and Inventive Step

The examiner allowed the claims because amendments filed by the applicant addressed previous rejections. Specifically, the examiner withdrew rejections based on new matter, obviousness over prior art (Arquette and Steinke), and provisional double patenting. The examiner stated that a declaration showed that enzymatic transesterification of jojoba oil feedstock with a lipase results in a significantly higher Oxidative Stability Index (OSI) even without adding alcohol. The examiner also noted that the prior art did not teach the feedstock comprising hydrogenated jojoba wax esters at an amount of 20% to 50% by weight of the feedstock, contacting the feedstock with a lipase to catalytically transesterify the wax esters in the feedstock to form a transesterified product, and does not teach the oxidative stability index (OSI) of the transesterified product is greater than an OSI of the feedstock.

Claims

This patent has 5 claims, with claim 1 being independent. Independent claim 1 is directed to a process for transesterifying wax esters using a feedstock comprising jojoba wax esters and hydrogenated jojoba wax esters. Dependent claims 2-5 further define the composition of the feedstock and transesterified product.

Key Claim Terms New

Definitions of key terms used in the patent claims.

Term (Source)Support for SpecificationInterpretation
Contacting the feedstock with a lipase
(Claim 1)
“Implementations of processes for transesterifying wax esters may include: providing a feedstock including wax esters, contacting the feedstock with a lipase, and catalytically transesterifying the wax esters in the feedstock with the lipase to form a transesterified product.”Bringing the feedstock into physical contact with a lipase enzyme.
Hydrogenated jojoba wax esters
(Claim 1)
“The jojoba wax esters may further include hydrogenated jojoba wax esters.”Jojoba wax esters that have undergone hydrogenation.
Jojoba wax esters
(Claim 1)
“A wax ester is formed from the chemical reaction of a fatty acid and a fatty alcohol, which results in the formation of an ester group that links two carbon chains. Wax esters are found in various animals and plants, including the jojoba plant (Simmondsia chinensis). Wax esters are used in various applications, including in cosmetic and personal care products.”Wax esters derived from the jojoba plant.
Oxidative stability index
(Claim 1)
“Implementations of processes for transesterifying wax esters may include: providing a feedstock including wax esters, contacting the feedstock with a lipase, and catalytically transesterifying the wax esters in the feedstock with the lipase to form a transesterified product. An oxidative stability index (OSI) of the transesterified product may be greater than an OSI of the feedstock.”A measure of the resistance of the transesterified product and feedstock to oxidation.
Transesterified product
(Claim 1)
“Implementations of processes for transesterifying wax esters may include: providing a feedstock including wax esters, contacting the feedstock with a lipase, and catalytically transesterifying the wax esters in the feedstock with the lipase to form a transesterified product.”The product resulting from the transesterification of wax esters.

Litigation Cases New

US Latest litigation cases involving this patent.

Case NumberFiling DateTitle
1:25-cv-00690Jun 4, 2025Cargill, Incorporated V. Vantage Specialty Chemicals, Inc.
1:22-cv-00979Jul 26, 2022Cargill, Incorporated et al v. Vantage Specialty Chemicals, Inc.

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US11248245

CARGILL INC
Application Number
US14578075
Filing Date
Dec 19, 2014
Status
Granted
Expiry Date
Jan 30, 2038
External Links
Slate, USPTO, Google Patents