C15-Wittig Salt Purification for High-All-E Lycopene
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Solution Overview
Problem
Conventional synthesis processes for producing synthetic lycopene result in low all-E content, with E/Z isomer ratios of 3.4:1 to 3.8:1, failing to meet the specifications of biological lycopene extracted from natural sources like Blakeslea trispora, and existing thermal isomerization processes only increase all-E content to 73.4%-87.8%.
Innovation Solution
Purification of C15-Wittig salts using a series of steps in aprotic solvents to achieve high E/Z selectivity, followed by a double Wittig reaction with C10-dialdehyde, allowing for the production of synthetic lycopene with up to 95% all-E content or 97% 5Z content by controlling solvent combinations and reaction temperatures.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If conventional synthesis process is used to produce C15 phosphonium salts, then lycopene can be synthesized, but the all-E content is low (65.2%-71.1%) and E/Z selectivity is poor (3.4:1 to 3.8:1)
Solution Approach 1:
The patent applies preliminary action by performing purification of C15 phosphonium salts before the main lycopene synthesis reaction. The purification step using aprotic solvents and controlled temperature removes cis-isomers in advance, ensuring high all-E content (≥90%) in the starting material, which directly leads to high all-E lycopene content in the final product.
Solution Approach 2:
The patent employs parameter changes by modifying reaction conditions including using aprotic solvents (acetone, ethyl methyl ketone, methyl isobutyl ketone), controlling reaction temperature (0°C to 50°C), and adjusting solvent ratios to optimize the E/Z selectivity during purification and synthesis, achieving E/Z ratios greater than 15:1.
2Manufacturing precision
If thermal isomerization process is used to increase all-E content, then all-E content can be improved (73.4%-87.8%), but the process is complex and time-consuming
Solution Approach 1:
The patent extracts and removes cis-isomers from the C15 phosphonium salt mixture through purification steps using aprotic solvents before synthesis. This extraction approach eliminates the need for subsequent thermal isomerization processes to convert Z-isomers to E-isomers, significantly reducing processing time while achieving ≥90% all-E content.
3Manufacturing precision
If high all-trans pseudoionone is used as starting material, then all-E lycopene content can be improved, but separation of all-trans from cis isomers is difficult
Solution Approach 1:
The patent changes the parameter of solvent type from conventional solvents to aprotic solvents (acetone, ethyl methyl ketone, methyl isobutyl ketone) and controls temperature parameters during purification. This enables effective separation of cis/trans isomers based on their different solubility and crystallization behavior in aprotic solvents, achieving high purity C15 phosphonium salts with ≥90% all-E content.
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 method achieves E/Z isomer ratios greater than 15:1 for all-E-C15-Wittig salts and less than 1:30 for 6Z-C15-Wittig salts, enabling the production of synthetic lycopene that meets or exceeds the all-E content specifications of biological lycopene, with all-E content up to 95% and 5Z content up to 97%.
Implementation Method 1
purification of C15-Wittig salts using a series of steps in aprotic solvents to achieve high E/Z selectivity
Implementation Method 2
double Wittig reaction with C10-dialdehyde, allowing for the production of synthetic lycopene with up to 95% all-E content or 97% 5Z content
Data Source
AI summary
The present invention relates to methods for preparation of lycopenes, especially to lycopenes with high all-E contents or high 6Z contents from C15-Wittig slats mixtures.(with high all-E-contents and high 6Z-contents, respectively). C15-Wittig slats mixtures are purified and 6Z-C15-Wittig salts are extracted from the mixtures. The extracted 6Z-C15-Wittig salts are, used in the synthesis of lycopenes with high 6Z contents and the residues are used in the synthesis of lycopenes with high All-E contents.