Tetrahydromyrcenol Synthesis via Reductive Ring-Opening
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Solution Overview
Problem
Current methods for producing tetrahydromyrcenol, a compound used in the flavor and fragrance industry, lack an efficient and selective process, often resulting in undesired side products and suboptimal yields.
Innovation Solution
A reductive ring-opening process of a compound of formula (II) using H2 gas at pressures of 1-20 bar and temperatures of 15-100°C, in the presence of a catalyst like Pd/C and an acid, selectively producing tetrahydromyrcenol with minimal side products.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If conventional hydrogenation of alloocimenol isomers is used to produce tetrahydromyrcenol, then the production process is established, but the selectivity and yield are suboptimal with formation of undesired side products
Solution Approach 1:
The patent applies parameter changes by modifying reaction conditions including using H2 gas at pressures of 1-20 bar (preferably 3-15 bar) and temperatures of 15-100°C (preferably 20-80°C), and by selecting specific catalysts (Pd/C, Pt, Rh) to achieve high selectivity and yield in the reductive ring-opening reaction, resolving the contradiction between manufacturing precision and productivity
2Ease of manufacture
If conventional hydrogenation process is used, then production can proceed with established methods, but undesired side products are formed reducing product purity
Solution Approach 1:
The patent uses an intermediary approach by employing specific catalysts (Pd/C, Pt, Rh) and acid catalysts as mediators to facilitate the reductive ring-opening reaction, enabling high product purity while maintaining process simplicity through the use of these intermediary substances that guide the reaction toward the desired product
3Manufacturing precision
If reductive ring-opening is performed without optimized conditions, then the reaction can proceed, but selectivity at the correct position is not achieved leading to multiple ring-opening products
Solution Approach 1:
The patent applies local quality by creating specific local reaction conditions through the use of particular catalysts (Pd/C, Pt, Rh) and controlling local parameters such as H2 pressure (1-20 bar) and temperature (15-100°C) to ensure ring-opening occurs selectively at position 2, achieving high selectivity without excessive reaction control complexity
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 process achieves high selectivity and yield of tetrahydromyrcenol with minimal formation of undesired side products, ensuring a more efficient and effective production method.
Implementation Method 1
the reductive ring opening of a compound of formula (II) results in an excellent selectivity and yield of tetrahydromyrcenol... The reduction agent used in the process according to the present invention is preferably H2 gas... the reaction is carried out with H2-gas at a pressure of 1 - 20 bar, preferably at 3 - 15 bar
Implementation Method 2
The compound of formula (II) can, for example, be prepared from dehydrolinalool by ring closure catalysed by tungsten, molybdenum or polyphosphoric acid
Data Source
AI summary
The present invention relates to a new and improved synthesis of tetrahydromyrcenol (IUPAC name: 2,6-dimethyl-2-octanol).