Peroxyester Production via Anhydride Recycling
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
Existing processes for preparing peroxyesters using acid anhydrides and organic hydroperoxides result in high Chemical Oxygen Demand (COD) waste streams and require expensive reagents, making them economically and environmentally unattractive.
Innovation Solution
A process involving the reaction of an anhydride with an organic hydroperoxide in the presence of a base to produce peroxyesters, followed by separation of carboxylic acid salts, liberation of carboxylic acid, optional recycling of carboxylic acid, and formation of an anhydride for recycling, which reduces COD and eliminates the use of acid chlorides.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If acid chlorides are used to prepare peroxyesters, then the reaction proceeds efficiently, but chloride-containing waste waters with high salt concentration are generated
Solution Approach 1:
The patent replaces expensive and environmentally harmful acid chlorides with cheaper and more environmentally friendly acid anhydrides. The acid anhydrides undergo reaction to form the desired peroxyesters while generating carboxylic acid salts that can be easily separated and converted back to carboxylic acid, eliminating the need for chloride-containing waste water treatment.
Solution Approach 2:
The patent changes the chemical parameter of the reagent from acid chloride to acid anhydride. This parameter change fundamentally alters the reaction pathway and waste product profile, transforming the harmful chloride-containing waste water into a system where carboxylic acid salts are generated and can be recycled back to carboxylic acid through acid treatment.
2Productivity
If acid anhydrides are used to prepare peroxyesters, then the reaction proceeds, but the waste stream contains high organic load with high COD value
Solution Approach 1:
The patent implements a recovery system for the carboxylic acid byproduct. Instead of discarding the carboxylic acid salt formed during the reaction, it is separated from the reaction mixture, treated with acid to regenerate the carboxylic acid, and recycled back to the reaction system. This recovery process eliminates the high COD waste stream that would otherwise be generated from the carboxylic acid salt.
Solution Approach 2:
The patent establishes a feedback loop where the carboxylic acid byproduct is converted back into a useful reagent. The carboxylic acid salt formed during the peroxyester synthesis is separated, treated with acid to regenerate carboxylic acid, and then recycled to react with more hydroperoxide and anhydride, creating a self-sustaining process that eliminates waste.
3Productivity
If acid chlorides are used in the process, then peroxyester production is achieved, but the process becomes economically unattractive due to high reagent cost
Solution Approach 1:
The patent replaces expensive acid chlorides with cheaper acid anhydrides as the key reagent. This substitution significantly reduces the cost of materials while maintaining the ability to produce peroxyesters efficiently. The acid anhydrides are less expensive and eliminate the need for costly chloride-based reagents and waste treatment processes.
4Productivity
If acid anhydrides are used in the process, then peroxyester production is achieved, but the process becomes environmentally unattractive due to high COD waste
Solution Approach 1:
The patent recovers and recycling the carboxylic acid byproduct to eliminate the high COD waste stream. The carboxylic acid salt formed during the reaction is separated from the organic phase, treated with acid to regenerate carboxylic acid, and recycled back to the reaction system. This closed-loop approach eliminates the need to discharge high COD waste water, making the process environmentally attractive.
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 achieves a significant reduction in COD effluents, eliminates the need for expensive acid chlorides, and enhances economic and environmental sustainability by allowing on-site production of peroxyesters with minimized storage and safety concerns.
Implementation Method 1
producing a mixture comprising one or more peroxyesters and one or more carboxylic acid salts or adducts by reacting an anhydride with the formula R1—C(═O)—O—C(═O)—R2 with an organic hydroperoxide of the formula R3(OOH)n in the presence of a base
Implementation Method 2
separating the one or more carboxylic acid salts or adducts from the mixture produced in step a)
Implementation Method 3
liberating the carboxylic acid from the salt or adduct
Implementation Method 4
producing an additional amount of carboxylic acid by reacting an aldehyde of the formula R2—C(═O)H with oxygen
Implementation Method 5
reacting the carboxylic acid obtained in step c) and optionally an additional amount of carboxylic acid of the formula R2—C(═O)OH—the additional amount of carboxylic acid being obtained from step d) and/or obtained in another way—with an acid anhydride or a ketene of the formula C(R4)2=C=O, each R4 being independently chosen from H and CH3, to form an anhydride with the formula R1—C(═O)—O—C(═O)—R2
Data Source
AI summary
Process for the production of a peroxyester involving the reaction of an anhydride with an organic hydroperoxide, separation of the formed carboxylic acid, production of an anhydride from said carboxylic acid, and recycling of the anhydride within the process.