Processes And Systems For Catalytic Manufacture Of Wax Ester Derivatives

Patent No. US12203122 (titled "Processes And Systems For Catalytic Manufacture Of Wax Ester Derivatives") was filed by Cargill Inc on Jan 26, 2023.

What is this patent about?

’122 is related to the field of processing wax esters, specifically jojoba wax esters, for use in cosmetic and personal care products. Traditional methods of transesterification, which alter the physical properties of wax esters, often rely on chemical catalysts. These chemical processes can degrade desirable components naturally present in wax ester feedstocks, such as antioxidants and volatile compounds, and introduce undesirable byproducts.

The underlying idea behind ’122 is to use enzymatic catalysis with a lipase to transesterify wax esters, particularly jojoba wax esters. This enzymatic approach avoids the harsh conditions and side reactions associated with chemical catalysts. By using a lipase, the process can be performed at lower temperatures and ambient pressure, preserving the beneficial components of the feedstock and minimizing the formation of unwanted byproducts like methyl esters and free fatty alcohols.

The claims of ’122 focus on a continuous process for producing a jojoba wax ester product. The process involves continuously contacting a feedstock containing jojoba wax esters and hydrogenated jojoba wax esters with an immobilized lipase enzyme catalyst. The lipase then catalytically transesterifies the wax esters, resulting in a product containing transesterified wax esters and, importantly, retaining the feedstock's tocopherol (a natural antioxidant).

In practice, the feedstock is passed through a reactor containing the immobilized lipase. The continuous nature of the process allows for efficient and scalable production. The use of an immobilized lipase facilitates its reuse and prevents contamination of the product. The reaction conditions are mild enough to preserve heat-sensitive components like tocopherols, which contribute to the oxidative stability of the final product. The degree of hydrogenation of the jojoba wax esters can be controlled to tailor the dropping point of the final product.

Unlike chemical transesterification, the enzymatic process does not generate fatty acid methyl esters or free fatty alcohols. Furthermore, the enzymatic process surprisingly increases the oxidative stability index (OSI) of the transesterified product compared to the feedstock, indicating enhanced shelf life. The lipase catalyst also exhibits a longer lifespan than expected based on its use in triglyceride processing, achieving a higher product-to-catalyst ratio. This makes the enzymatic process more efficient and cost-effective.

How does this patent fit in bigger picture?

Technical landscape at the time

In the mid-2010s when ’122 was filed, wax esters were typically reacted and processed using chemical catalysts. At this time, systems commonly relied on chemical catalysts to carry out transesterification reactions. Hardware or software constraints made it non-trivial to achieve high yields and maintain the oxidative stability of the resulting products when using these chemical catalysts.

Novelty and Inventive Step

The examiner allowed the claims because the prior art (Lee et al. and Arquette) did not teach or suggest using a lipase enzyme catalyst to catalyze an ester-ester exchange of wax esters, specifically jojoba wax esters. The examiner agreed with the applicant's argument that prior art compositions comprised fats or oils with a glycerol backbone, and selective lipases would be expected to act on the glycerol. The examiner also cited a PTAB ruling that supported the non-obviousness of using a lipase enzyme for wax ester-ester transesterification compared to using it for triglyceride production, as lipase enzymes are known to bind with glycerol backbone structures, which wax esters lack. Furthermore, the applicant demonstrated that using a chemical catalyst altered the properties of the product by removing or degrading tocopherol, affecting oxidative stability, while a lipase enzyme catalyst did not.

Claims

This patent contains 20 claims, with claims 1 and 18 being independent. The independent claims focus on a jojoba wax ester product and a method of making it, both involving reacting jojoba wax esters and hydrogenated jojoba wax esters with an immobilized lipase enzyme catalyst. The dependent claims generally specify details and limitations related to the composition of the feedstock, the characteristics of the product, and the type of lipase enzyme catalyst used.

Key Claim Terms New

Definitions of key terms used in the patent claims.

Term (Source)Support for SpecificationInterpretation
Feedstock wax esters
(Claim 1, Claim 18)
“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.”Wax esters that are present in the feedstock before the transesterification process.
Hydrogenated jojoba wax esters
(Claim 1, Claim 18)
“The jojoba wax esters may further include hydrogenated jojoba wax esters.”Jojoba wax esters that have undergone hydrogenation.
Immobilized lipase enzyme catalyst
(Claim 1, Claim 18)
“Implementations of a process for transesterifying wax esters may include providing a feedstock including jojoba wax esters, contacting the feedstock with a lipase catalyst, and catalytically transesterifying the jojoba wax esters in the feedstock with the lipase to form a transesterified product.”A lipase enzyme catalyst that is not free-flowing within the reaction.
Jojoba wax esters
(Claim 1, Claim 18)
“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 derived from the jojoba plant.
Transesterified product wax esters
(Claim 1, Claim 18)
“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.”Wax esters that are the result of the transesterification process.

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.

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US12203122

CARGILL INC
Application Number
US18159747
Filing Date
Jan 26, 2023
Status
Granted
Expiry Date
Dec 19, 2034
External Links
Slate, USPTO, Google Patents