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Solution Overview
Problem
The yield of fragrance compounds like 2-oxygenated decalins is reduced due to side reactions of carbamate by-products formed during the chlorination of geranyl amine with chloroformate, leading to inefficient production processes.
Innovation Solution
A method involving a halogenation step followed by distillation to separate and purify geranyl chloride, reducing the concentration of carbamate impurities, thereby minimizing side reactions and enhancing the purity of geranyl chloride for improved fragrance compound production.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Quantity of substance
If chlorination of geranyl amine with chloroformate is performed to produce geranyl chloride, then geranyl chloride is obtained, but carbamate by-product is formed which reduces reaction yield through side reactions
Solution Approach 1:
The patent applies extraction by performing a distillation step that separates geranyl chloride from the carbamate by-product based on their different volatilities. The geranyl chloride is distilled off from the reaction mixture, leaving the carbamate behind, thereby removing the harmful by-product that causes side reactions and reduces yield.
Solution Approach 2:
The patent applies preliminary action by carrying out the distillation step immediately after the chlorination reaction to remove the carbamate by-product before it can participate in side reactions. This preliminary removal of the harmful substance prevents subsequent yield-reducing reactions when nucleophiles are added.
2Manufacturing precision
If distillation is performed to remove carbamate by-product, then geranyl chloride purity is improved, but additional process time and complexity are required
Solution Approach 1:
The patent utilizes phase transition (distillation) to separate geranyl chloride from carbamate by exploiting their different volatilities. Geranyl chloride has a lower boiling point and can be distilled off, while carbamate remains in the residue. This phase-based separation achieves high purity without requiring complex purification equipment.
3Productivity
If carbamate by-product remains in the reaction mixture, then process steps are simplified, but side reactions with nucleophiles reduce overall reaction yield
Solution Approach 1:
The patent converts the harmful carbamate by-product into a beneficial separation opportunity. By exploiting the volatility difference between geranyl chloride and carbamate, the distillation process transforms the presence of the by-product into a means of purifying the desired product. The carbamate, initially harmful, becomes a useful indicator for separation and removal.
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 distillation process increases the purity of geranyl chloride, allowing for more effective reactions with nucleophiles to produce intermediates for fragrances such as 2-oxygenated decalins, improving overall production efficiency.
Implementation Method 1
a distillation step, the distillation step comprising distilling a mixture comprising the first reaction mixture to produce a separated portion of the distillation mixture comprising a purified form of the compound of Formula (I)
Data Source
AI summary
Described herein are methods for making intermediates useful in the production of fragrance ingredients starting from myrcene. In particular, methods for making geranyl chloride, (E)-6,10-dimethylundeca-1,5,9-triene and (E)-6,10-dimethylundeca-5,9-dien-1-yne are described. Methods for making other intermediates in the process are also described.