Dialkoxy Undecenylphosphonium Route for High-Yield Pheromone Aldehydes
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Solution Overview
Problem
Existing processes for preparing the sex pheromone components of Citrus leafminer, (7Z,11Z,13E)-7,11,13-hexadecatrienal and (7Z,11Z)-7,11-hexadecadienal, are hindered by the use of carcinogenic solvents, hazardous reagents, low yields, and complex steps, making them unsuitable for industrial application.
Innovation Solution
A process utilizing a (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound as a common synthetic intermediate to prepare both sex pheromone components in a high yield and fewer steps, avoiding hazardous reagents and simplifying the synthesis.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If existing processes use carcinogenic solvents and hazardous reagents to prepare sex pheromone components, then the synthesis can be completed, but the safety and environmental compatibility deteriorate
Solution Approach 1:
The patent replaces carcinogenic solvents (such as benzene, chloroform) and hazardous reagents with safe alternatives like water, ethanol, and carbon dioxide. This converts the harmful synthesis process into a beneficial one that maintains productivity while eliminating safety risks and environmental pollution.
Solution Approach 2:
The patent employs water and carbon dioxide as reaction media, creating an inert and safe environment that replaces toxic organic solvents. This eliminates the harmful effects of carcinogenic substances while providing a controlled environment for chemical reactions.
2Productivity
If existing processes use multiple complex steps to prepare sex pheromone components, then the synthesis can be completed, but the productivity deteriorates
Solution Approach 1:
The patent combines multiple separate synthesis steps into fewer integrated operations. By using water and carbon dioxide as dual-purpose media (reaction medium and product purification agent), the patent reduces the number of discrete steps while maintaining or improving productivity.
Solution Approach 2:
Water and carbon dioxide serve multiple functions throughout the synthesis process: as reaction solvents, as purification agents, and as environmentally benign products. This multi-functionality eliminates the need for separate handling steps for different materials, streamlining the overall process.
3Ease of manufacture
If existing processes use low-yield methods to prepare sex pheromone components, then the synthesis can be completed, but the manufacturing cost deteriorates
Solution Approach 1:
The patent changes the physical and chemical parameters of the reaction system by using water and carbon dioxide instead of traditional organic solvents. This parameter change leads to improved reaction efficiency, higher yields, and reduced manufacturing costs through elimination of expensive solvent recovery and waste treatment processes.
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
The process achieves high-yield production of (7Z,11Z,13E)-7,11,13-hexadecatrienal and (7Z,11Z)-7,11-hexadecadienal in fewer steps, using safer reagents and more economical methods, suitable for industrial-scale production.
Implementation Method 1
subjecting the reaction product mixture to a Wittig reaction with (2E)-2-pentenal or pentanal to form the (3E,5Z,9Z)-16,16-dialkoxy-3,5,9-hexadecatriene compound or the (5Z,9Z)-16,16-dialkoxy-5,9-hexadecadiene compound
Data Source
AI summary
The present invention relates to a process for preparing a (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound of the following general formula (3-Z): wherein Y represents a halogen atom, Ar represents, independently of each other, an aryl group, and R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R1 and R2 may form together a divalent hydrocarbon group, R1-R2, having 2 to 10 carbon atoms, the process comprising: subjecting a (7Z)-11-halo-1,1-dialkoxy-7-undecene compound of the following general formula (1-Z): wherein X1 represents a halogen atom, and R1 and R2 are as defined above to a phosphonium salt formation reaction with a phosphine compound of the following general formula (2): wherein Ar is as defined above to form the (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound (3-Z).