High-Weight Ester Synthesis via Cross-Metathesis
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Solution Overview
Problem
There is a need for environmentally friendly techniques to manufacture materials typically derived from petroleum sources, and a demand for natural oil fatty acid or ester waxes that can substitute or extend existing waxes like beeswax, Montan wax, Carnauba Wax, Candelilla Wax, or Ouricury Wax, with metathesis reactions offering promising solutions but requiring improved efficiency and catalyst performance.
Innovation Solution
The method involves agitating metathesized products as they cool from elevated temperatures to alter their properties, reducing high-weight esters to form high-weight alcohols, and transesterifying them with fatty acid esters or alcohols to create beeswax-like compositions through cross-metathesis reactions with hydrocarbon and free fatty acid feedstocks.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Object-affected harmful factors
If metathesis reactions are used to produce high-weight esters from natural oils, then environmentally friendly manufacturing is achieved, but reaction efficiency and catalyst performance need improvement
Solution Approach 1:
The patent applies parameter changes by optimizing reaction conditions including temperature ranges (20-200°C), pressure conditions (1-100 atm), and catalyst concentrations (0.1-10 wt%) to enhance metathesis reaction efficiency while maintaining environmental sustainability through natural oil feedstocks
Solution Approach 2:
The patent uses metal oxide catalysts (such as tungsten oxide, molybdenum oxide, rhenium oxide) as intermediaries to facilitate the metathesis reaction between natural oils and olefins, improving reaction efficiency and selectivity for producing high-weight esters with desired properties
2Manufacturing precision
If extensive chromic acid treatment is used to refine Montan wax, then wax purity is improved, but the process becomes costly and environmentally problematic
Solution Approach 1:
The patent extracts and removes unwanted components from natural oil feedstocks through filtration and separation processes before and during the metathesis reaction, achieving high purity esters without requiring extensive chromic acid treatment, thereby reducing refining costs and environmental impact
Solution Approach 2:
The patent replaces expensive and environmentally harmful chromic acid treatment with more economical refining approaches using metal oxide catalysts and simple filtration processes, achieving comparable purity at lower cost
3Object-affected harmful factors
If natural oil feedstocks are used to produce wax substitutes, then sustainability is improved, but product consistency and supply reliability face challenges
Solution Approach 1:
The patent uses universal metal oxide catalysts that can process various natural oil feedstocks (vegetable oils, animal fats) to produce consistent high-weight ester products, ensuring supply reliability and product consistency while maintaining sustainability through renewable feedstock utilization
Solution Approach 2:
The patent optimizes reaction parameters including temperature, pressure, and catalyst loading to ensure consistent product properties regardless of natural oil feedstock variations, achieving reliable and reproducible wax substitutes from renewable sources
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 process enhances the production of high-weight ester compositions with properties similar to commercial waxes, improving efficiency and sustainability by utilizing natural oil feedstocks and optimizing catalyst use, resulting in wax-like materials suitable for various applications.
Implementation Method 1
cross-metathesizing a natural oil feedstock with an olefin feedstock in the presence of a metathesis catalyst to form a metathesized product
Implementation Method 2
hydrogenating the olefins in the metathesized product to form a hydrogenated product
Implementation Method 3
separating the metathesized product into olefin and ester streams
Data Source
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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 comprising 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. In certain embodiments, the low-weight unsaturated esters or low-weight unsaturated acids are derived by reacting a natural oil feedstock in a metathesis reactor in the presence of a metathesis catalyst to form a metathesized product composition comprising olefins and low-weight unsaturated esters, and then separating the olefins from the low-weight unsaturated esters. In some embodiments, the low-weight unsaturated ester compositions may be hydrolyzed to form the low-weight unsaturated acid compositions.