Indanone Synthesis via Azeotropic Solvent Substitution
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Solution Overview
Problem
The existing method for producing 2-benzylidene-3,3-dimethyl-5,6-dimethoxy-1-indanone is economically and ecologically disadvantageous due to the use of carcinogenic diethylene glycol dimethyl ether, results in contamination with undesirable by-products, and produces a product with a disturbing yellow color.
Innovation Solution
The method involves dissolving indanone in a solvent that forms an azeotrope with water, converting it with an aromatic aldehyde in the presence of an organic base, and removing water from the reaction mixture, which reduces by-product formation and improves yield, using solvents like toluol and xylol to facilitate azeotropic distillation and minimize residual solvent contamination.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If diethylene glycol dimethyl ether is used as solvent, then the reaction can proceed, but the product is contaminated with carcinogenic substances and produces yellow coloring
Solution Approach 1:
The patent changes the solvent parameter from diethylene glycol dimethyl ether to toluol or xylol, which are non-carcinogenic solvents that do not produce yellow coloring. This parameter substitution maintains reaction feasibility while eliminating harmful effects in the final product.
Solution Approach 2:
The patent extracts and removes the harmful diethylene glycol dimethyl ether from the reaction system by replacing it with alternative solvents (toluol or xylol) that do not introduce carcinogenic substances or yellow coloring, thereby separating the harmful factor from the productive function.
2Ease of manufacture
If diethylene glycol dimethyl ether is used as solvent, then the reaction can proceed, but the solvent is highly water-soluble and causes ecological damage
Solution Approach 1:
The patent changes the solvent's water solubility parameter by substituting diethylene glycol dimethyl ether (highly water-soluble) with toluol or xylol (low water solubility). This parameter change maintains the solvent's ability to dissolve reactants while preventing ecological damage from water contamination.
3Productivity
If conventional method is used, then production yield is achieved, but by-products are formed and require complex extraction
Solution Approach 1:
The patent changes the solvent parameter to toluol or xylol, which provides superior selectivity in the reaction system. This parameter change enhances product purity by reducing by-product formation while maintaining good production yield, eliminating the need for complex extraction procedures.
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 approach significantly increases the yield, reduces the content of undesirable by-products and yellow coloring substances, and minimizes the use of organic bases, resulting in a product with high purity and reduced ecological impact.
Implementation Method 1
dissolving an indanone having the formula (II) in a solvent or in an admixture which contains a solvent, the solvent being selected from the group of solvents which form an azeotrope with water
Implementation Method 2
converting the indanone having the formula (II) with an aromatic aldehyde having the formula (III) in the presence of at least one organic base
Data Source
AI summary
A method is described for producing a compound having the formula (I)or an admixture comprising a compound having the formula (I),having the following steps:dissolving an indanone having the formula (II) in a solvent or in an admixture which contains a solvent, the solvent being selected from the group of solvents which form an azeotrope with water,converting the indanone having the formula (II) with an aromatic aldehyde having the formula (III) in the presence of at least one organic base, according to the drawing:where R1 and R2 independently of each other signify hydrogen or a branched or unbranched alkyl group having from 1 to 12 carbon atoms andwhere R3, R4, R5, R6, R7, R8, R9, R10 and R11 independently of each other signify hydrogen, hydroxy or a branched or unbranched alkyl or alkoxy group having from 1 to 12 carbon atoms andremoving water formed from the reaction admixture during the conversion.An admixture comprising a compound of the formula (I) and other components is further described.