Z-Selective Olefin Metathesis for Cost-Efficient Pheromone Synthesis
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Solution Overview
Problem
The high cost of synthesizing insect pheromones using current techniques prohibits their widespread use beyond high-value crops, necessitating the development of cost-efficient production methods for these molecules and related compounds.
Innovation Solution
The use of Z-selective olefin metathesis catalysts in conjunction with low-cost feedstocks to produce high Z-isomeric purity unsaturated fatty olefin metathesis products, including synthetic insect pheromones, through stereo-retentive olefin cross-metathesis reactions.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If conventional synthesis techniques are used to produce insect pheromones, then high Z-isomeric purity can be achieved, but the synthesis cost becomes very high
Solution Approach 1:
The patent changes the chemical parameters of the reaction system by introducing Z-selective metathesis catalysts with specific ligand configurations (Formula V with specific M, X, Y, Z, m, n values and R groups) to achieve high Z-isomeric purity at lower synthesis costs. This parameter change in catalyst structure enables cost-effective production while maintaining high manufacturing precision.
2Ease of manufacture
If Z-selective olefin metathesis catalysts are used, then synthesis cost is reduced, but the complexity of the catalytic system increases
Solution Approach 1:
The patent applies local quality by introducing specific functional groups and ligand configurations at particular positions in the catalyst structure (Formula V). The catalyst contains specific elements (M from group 8, X and Y from S/O, Z from O/S(=O)/N/halogen) at defined positions, creating localized functional regions that enable Z-selectivity while maintaining overall cost-effectiveness. This localized functional assignment reduces the need for complex overall system design.
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 allows for the cost-effective synthesis of high-purity insect pheromones and related compounds, enhancing their industrial applicability and sustainability in pest control.
Implementation Method 1
contacting an olefin metathesis reaction partner with an internal olefin in the presence of a Z-selective group 8 transition metal metathesis catalyst to form the Z-enriched fatty olefin metathesis product
Implementation Method 2
Z-selective group 8 transition metal metathesis catalyst
Data Source
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AI summary
Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.