Metathesis Process for High-Purity Bifunctional Organic Compounds
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Solution Overview
Problem
Metathesis reactions applied to natural oil-derived feedstocks often result in mixtures of products, making it difficult to separate desired compounds like specific chain length diesters due to similarities in molecular weight and functionality.
Innovation Solution
A method involving cross-metathesis with a short-chain olefin to produce functionalized alkenes, which are then isolated and self-metathesized to form high-purity bifunctional organic compounds such as diacids, diesters, or dicarboxylate salts from starting materials like fatty acids or esters.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If metathesis is applied directly to natural oil-derived feedstocks, then the reaction can proceed with simple starting materials, but a mixture of products results that is difficult to separate
Solution Approach 1:
The patent segments the metathesis process into two distinct stages: first performing metathesis on the natural oil-derived feedstocks to produce intermediate products, then selectively isolating desired intermediates before performing a second metathesis reaction. This segmentation allows the final product to be obtained in high purity by controlling which intermediates react in the second stage.
Solution Approach 2:
The patent applies preliminary action by first conducting metathesis reactions to create a mixture of intermediate products, then selectively isolating specific intermediates before the final metathesis step. This preliminary isolation ensures that only the desired intermediates proceed to the final reaction, guaranteeing high product purity.
2Adaptability or versatility
If metathesis produces a mixture of monoesters and diesters with various chain lengths, then the reaction covers multiple product possibilities, but separation of desired product becomes difficult due to similarity in molecular weight and functionality
Solution Approach 1:
The patent segments the product mixture into distinct intermediate categories (monoesters, diesters with various chain lengths) after the first metathesis reaction, then selectively isolates the desired intermediate before the second metathesis step. This segmentation prevents the need to separate final products with similar properties.
Solution Approach 2:
The patent performs preliminary isolation of specific intermediates (such as C10 diester or C12 diester) from the first metathesis mixture before conducting the second metathesis reaction. This preliminary action ensures that only the desired intermediate concentration is carried forward, eliminating separation issues in the final product.
3Manufacturing precision
If cross-metathesis with short-chain olefin is performed first, then functionalized alkenes with pre-determined double bond position are produced that can be isolated at high purity, but an additional reaction step is required
Solution Approach 1:
The patent performs cross-metathesis with short-chain olefins as a preliminary step to create functionalized alkenes with predetermined double bond positions. These intermediates are then isolated in high purity before the final metathesis reaction, ensuring precise control over the final product structure.
Solution Approach 2:
The patent introduces functionalized alkenes as intermediary compounds with specific double bond positions that serve as controlled intermediates between the starting feedstocks and the final bifunctional organic compounds. These intermediaries allow precise control over the final product's carbon chain length and functionality.
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
Enables the production of high-purity bifunctional organic compounds by isolating and further processing functionalized alkenes, improving the yield and purity of desired products from natural oil-derived feedstocks.
Implementation Method 1
Metathesis is a catalytic reaction involving the rupture and reformation of carbon-carbon double bonds
Data Source
AI summary
Described are methods of making organic compounds by metathesis chemistry. The methods of the invention are particularly useful for making industrially-important organic compounds beginning with starting compositions derived from renewable feedstocks, such as natural oils. The methods make use of a cross-metathesis step with an olefin compound to produce functionalized alkene intermediates having a pre-determined double bond position. Once isolated, the functionalized alkene intermediate can be self-metathesized or cross-metathesized (e.g., with a second functionalized alkene) to produce the desired organic compound or a precursor thereto. The method may be used to make bifunctional organic compounds, such as diacids, diesters, dicarboxylate salts, acid/esters, acid/amines, acid/alcohols, acid/aldehydes, acid/ketones, acid/halides, acid/nitriles, ester/amines, ester/alcohols, ester/aldehydes, ester/ketones, ester/halides, ester/nitriles, and the like.