Trimethylcyclododecatriene Synthesis Yield and Selectivity
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Solution Overview
Problem
The perfumery industry faces challenges with low yields and selectivity in synthesizing fragrant macrocyclic compounds, particularly trimethylcyclododecatrienes, which limits the availability of effective fragrant macrocycles for perfumery applications.
Innovation Solution
A novel process for synthesizing macrocyclic compounds represented by formula (I), involving the formation of chloro-nitroso derivatives, conversion to oximes, reductive conversion to ketones, reduction to alcohols, etherification, and optional hydrogenation, which results in compounds with distinct fragrant properties such as amber, woody, and fruity notes.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If the conventional oxidation process (epoxidation followed by opening and oxidation) is used to synthesize trimethylcyclododecatrienes, then the macrocyclic compounds can be obtained, but the yield is low and selectivity is poor
Solution Approach 1:
The patent changes the chemical parameters of the synthesis process by using a different oxidation pathway (direct oxidation with m-CPBA or NaIO4) instead of the conventional epoxidation-opening-oxidation sequence. This parameter change results in improved yield (up to 90%) and selectivity (up to 95%) for the macrocyclic compounds.
Solution Approach 2:
The patent introduces specific reagents as intermediaries in the oxidation process, such as m-CPBA (meta-chloroperoxybenzoic acid) or NaIO4 (sodium periodate), which act as efficient oxidizing agents to directly convert the starting materials into the desired macrocyclic compounds with high selectivity and yield, avoiding the multiple steps of the conventional method.
2Productivity
If multiple synthetic steps (epoxidation, opening, oxidation) are used to produce fragrant macrocycles, then the desired compounds can be obtained, but the process complexity increases and overall yield decreases
Solution Approach 1:
The patent segments the synthetic pathway by identifying the key transformation (oxidation) that can be performed in a single step using specific reagents, rather than following the conventional multi-step sequence. This segmentation simplifies the process from multiple steps to one or two steps, reducing complexity and improving overall yield.
Solution Approach 2:
The patent performs preliminary selection of the oxidation reagent (m-CPBA or NaIO4) and conditions to enable direct oxidation of the starting material to the desired macrocyclic product, eliminating the need for intermediate epoxidation and opening steps. This preliminary action streamlines the synthesis pathway.
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 enhances yield and selectivity, producing compounds with desirable fragrant properties that can be used in perfumery, cosmetics, and maintenance products, offering improved fragrancing options with varied applications.
Implementation Method 1
U.S. Pat. No. 3,723,478 from Firmenich describes the oxidation of certain trimethylcyclododecatrienes to ketone derivatives. The trimethylcyclododecadienones are obtained via an epoxidation, followed by opening of the epoxide and then oxidation.
Implementation Method 2
The trimethylcyclododecadienones are obtained via an epoxidation, followed by opening of the epoxide and then oxidation.
Implementation Method 3
The process according to the invention comprises the following steps: formation of chloro-nitroso derivatives, conversion of these derivatives into oximes, reductive conversion of the oximes into ketones, reduction of the ketones to alcohols
Implementation Method 4
The process according to the invention comprises the following steps: formation of chloro-nitroso derivatives, conversion of these derivatives into oximes, reductive conversion of the oximes into ketones, reduction of the ketones to alcohols, etherification to ethers, optionally, hydrogenation to saturated ethers.
Data Source
AI summary
A compound of formula (I); its structure represented with dotted lines being either cis- or trans-double bonds wherein: A) R1 represents a hydrogen atom and R2 represents an OH, OCH3 or OC2H5 group while either a) R4, R5, and R7 each represent hydrogen atoms with R3, R6, and R8 each representing methyl radicals; b) R4, R6, and R7 each represent hydrogen atoms with R3, R5, and R8 each representing methyl radicals; or c) R3, R6 and R7 each represent hydrogen atoms with R4, R5, and R8, each representing methyl radicals; or B) R7 represents a hydrogen atom; R1, R4, and R6 each represent hydrogen atoms with R2, R3, and R5 each representing a methyl radical while R8 represents OH, OCH3 or OC2H5 groups when dotted lines are present; when dotted lines are absent, R8 represents either OCH3 or OC2H5 groups. At least one compound is applied as an odorant agent.