High-Weight Ester Synthesis via Cross-Metathesis
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
There is a need for environmentally friendly techniques to manufacture materials derived from petroleum sources, particularly for producing waxes that can substitute or extend natural waxes like beeswax, Montan wax, Carnauba Wax, Candelilla Wax, or Ouricury Wax, and for improving the efficiency of metathesis catalysts used in these processes.
Innovation Solution
The method involves refining natural oils by providing a starting feedstock with unsaturated esters or acids, hydrolyzing, transesterifying, and cross-metathesizing with an olefin feedstock in the presence of a metathesis catalyst to produce high-weight esters or acids with extended hydrocarbon chain lengths, which are then agitated and further processed to alter properties, forming wax compositions with desired properties.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If natural waxes (beeswax, Montan wax, Carnauba wax) are used as feedstock, then desired wax properties are achieved, but supply uncertainty and cost fluctuations occur
Solution Approach 1:
The patent replaces expensive, scarce natural waxes with abundant, inexpensive vegetable oils as feedstock. The vegetable oils serve as a disposable, renewable resource that can be continuously produced, eliminating supply uncertainty associated with natural wax extraction from limited sources like carnauba palms or bee hives.
Solution Approach 2:
The patent changes the chemical parameters of the feedstock from natural waxes to vegetable oils, then uses metathesis reactions to modify the molecular structure. By changing the carbon chain length and composition through catalytic reactions, the patent transforms readily available vegetable oils into products with wax-like properties, adapting the feedstock to match the desired product specifications.
2Productivity
If metathesis catalysts are used to extend hydrocarbon chains, then high-weight esters are produced, but catalyst efficiency needs improvement
Solution Approach 1:
The patent uses metathesis catalysts as intermediaries to facilitate the chain-extension reaction between vegetable oil esters and olefins. The catalyst enables the transfer of carbon chains without being consumed in the reaction, allowing continuous production of high-weight esters. By optimizing the catalyst system, the patent improves the efficiency of this intermediary process, reducing energy losses and increasing productivity.
3Quantity of substance
If Montan wax is extracted from brown coal, then wax component is obtained, but extensive and costly cleaning is required
Solution Approach 1:
The patent extracts the desired ester components from vegetable oils through selective chemical reactions rather than physical extraction from coal. By using metathesis to specifically extend the carbon chains of oil esters, the patent obtains purified high-weight esters without the extensive cleaning and chromic acid treatment required for Montan wax extraction from brown coal.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
This approach enables the production of wax compositions with properties similar to commercial waxes, such as beeswax, Montan wax, Carnauba wax, or Candelilla wax, offering sustainable alternatives and improving catalyst efficiency, thus addressing the challenge of fluctuating natural wax availability and cost.
Implementation Method 1
cross-metathesizing with an olefin feedstock in the presence of a metathesis catalyst to produce high-weight esters or acids with extended hydrocarbon chain lengths
Implementation Method 2
hydrolyzing, transesterifying, and cross-metathesizing with an olefin feedstock
Data Source
AI summary
Methods and compositions are provided for refining natural oils and for producing high-weight esters, high-weight acids, and/or high-weight derivatives thereof, wherein the compositions are made by cross-metathesizing low-weight unsaturated esters or low-weight unsaturated acids having hydrocarbon chain lengths less than or equal to C24 with an olefin feedstock, thereby forming a metathesized product composition including high-weight esters or high-weight acids having hydrocarbon chain lengths greater than C18, wherein at least a portion of the hydrocarbon chain lengths in the metathesized product are larger than the hydrocarbon chain lengths in the starting feedstock.