3-Methylcyclopentadecane-1,5-dione Oxidation Process
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Solution Overview
Problem
Current methods for producing 3-methylcyclopentadecane-1,5-dione are inefficient, difficult to scale up, and involve the use of toxic or expensive reagents, such as ozone, singlet oxygen, and potassium permanganate.
Innovation Solution
Oxidation of 14-methylbicyclo[10.3.0]pentadecen[1(12)] using a mixture of formic acid and hydrogen peroxide as the sole oxidizing agent in the presence of water, with a stoichiometric ratio of at least 1.1 mol H2O2 per mol of the compound, directly forming 3-methylcyclopentadecane-1,5-dione with moderate yields and selectivity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If ozonolysis or photooxidation is used to prepare cyclopentadecane-1,5-dione, then the oxidation reaction can proceed, but the process becomes difficult to handle on large scale
Solution Approach 1:
The patent changes the oxidation method from ozonolysis or photooxidation to oxidation with hydrogen peroxide in formic acid, altering the reaction parameters to achieve both large-scale production capability and ease of operation. This parameter change allows the reaction to proceed efficiently while being manageable on industrial scale.
2Productivity
If potassium permanganate is used for oxidation, then the reaction can proceed, but the workup becomes difficult and produces waste
Solution Approach 1:
The patent replaces potassium permanganate with hydrogen peroxide as the oxidizing agent. Hydrogen peroxide decomposes into water and oxygen, eliminating the need for complex workup procedures and avoiding waste production from manganese byproducts. This substitution uses a cheaper, environmentally benign reagent that does not require disposal.
3Ease of manufacture
If sub-stoichiometric amount of H2O2 is used in formic acid, then the reaction proceeds as described in CH 513791, but only traces of 3-methylcyclopentadecane-1,5-dione are formed
Solution Approach 1:
The patent applies excessive action by using at least 1.1 mol H2O2 per mol of substrate, exceeding the sub-stoichiometric amounts used in prior art. This excessive use of hydrogen peroxide ensures complete oxidation and high yields of 3-methylcyclopentadecane-1,5-dione, resolving the low productivity issue while maintaining process simplicity.
4Manufacturing precision
If multiple reaction steps including Pb3O4 treatment are used, then the product can be obtained, but the process becomes tedious and requires toxic chemicals
Solution Approach 1:
The patent merges multiple reaction steps into a single oxidation step using hydrogen peroxide in formic acid. The oxidation and subsequent transformations that previously required separate steps with Pb3O4 treatment occur simultaneously in one pot, reducing the number of steps and eliminating toxic chemicals while maintaining product purity.
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 allows for efficient and scalable production of 3-methylcyclopentadecane-1,5-dione without the need for toxic or expensive reagents, as it forms the compound directly with high yields and selectivity, and is easier to handle than previous methods.
Implementation Method 1
oxidation of 14-methylbicyclo[10.3.0]pentadecen[1(12)] with an oxidizing agent, where the oxidation is performed by using a mixture of formic acid with H2O2 as sole oxidizing agent
Data Source
AI summary
The present invention relates to a process for producing 3-methylcyclopentadecane- 1,5-dione of formula (I), which comprises the oxidation of 14-methyl- bicyclo[10.3.0]pentadecen[1 (12)] of formula (II) with an oxidizing agent, where the oxidation is performed by using a mixture of formic acid with H2O2 as sole oxidizing agent in the presence of water and where the amount of H2O2 is at least 1.1 mol H2O2 per mol of the compound of formula (II).