Terpene Ozonolysis Acid Recovery via pH Separation
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Solution Overview
Problem
Ozonolysis procedures for producing aldehydes result in significant over-oxidation, leading to the formation of unwanted acid products that are typically regarded as waste, negatively impacting the economic viability of aldehyde production in industries such as flavors and fragrances.
Innovation Solution
A method involving ozonolysis of terpenes or their analogs, followed by reaction with an oxidant or reductant, and subsequent pH-adjusted separation to isolate and recover the acid product, allowing for its use in flavors, fragrances, and preservatives, thereby reducing waste and improving cost efficiency.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Quantity of substance
If ozonolysis procedure is used to produce aldehydes, then aldehyde product is obtained, but significant over-oxidation occurs producing unwanted acid products that are regarded as waste
Solution Approach 1:
The invention converts the harmful over-oxidation side reaction that produces waste acid into a beneficial feature by intentionally producing both aldehyde and acid products through controlled ozonolysis, then separating and utilizing both products. The acid product, previously considered waste, is now recovered and sold as a valuable byproduct, turning a chemical disadvantage into an economic advantage.
Solution Approach 2:
The invention implements a recovery system for the acid product that was previously discarded. Through pH-adjusted liquid-liquid extraction, the acid is separated from the aldehyde in the reaction mixture, purified, and recovered as a sellable product. This recovery process eliminates waste disposal costs and creates additional revenue streams.
2Quantity of substance
If over-oxidation is prevented to maximize aldehyde yield, then acid waste is minimized, but additional process controls and potential yield loss occur
Solution Approach 1:
Instead of trying to prevent over-oxidation to maximize aldehyde yield, the invention inverts the approach by accepting and utilizing both aldehyde and acid products. The process is designed to produce both compounds intentionally, then separates them through pH-adjusted extraction, eliminating the need for complex control mechanisms to prevent side reactions.
Solution Approach 2:
The invention uses pH parameter changes to control product distribution and separation. By adjusting pH to alkaline conditions, the acid is converted to its salt form and extracted into the aqueous phase, while the aldehyde remains in the organic phase. This simple parameter change enables easy separation without complex process controls.
3Loss of substance
If acid product is isolated and purified, then waste is reduced and economic viability improves, but additional processing steps and costs are incurred
Solution Approach 1:
The invention merges the separation and purification of acid and aldehyde into a single integrated process step. By performing pH-adjusted liquid-liquid extraction, both products are separated simultaneously in one operation, rather than requiring multiple sequential purification steps. This maintains process simplicity while achieving effective product isolation.
Solution Approach 2:
The invention uses pH adjustment as an intermediary mechanism to facilitate easy separation. By converting the acid to its salt form through pH control, the acid becomes water-soluble and separates from the organic-soluble aldehyde. This intermediary step simplifies the manufacturing process compared to direct separation methods.
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 method enables the cost-efficient isolation and utilization of acid products, enhancing the economic viability of aldehyde production by minimizing waste and maximizing the use of terpene-derived compounds in flavor and fragrance industries.
Implementation Method 1
Ozonolysis of terpenes and analogs thereof can produce aldehydes that are used as ingredients in flavors and fragrances
Implementation Method 2
reacting a compound having the formula IB with ozone and subsequently with an oxidant different from ozone to obtain the compound of formula (I) wherein R1 is H
Implementation Method 3
reacting a compound having the formula IB with ozone and subsequently with a reductant to obtain a mixture comprising the compound of formula (I) wherein R1 is H and a compound of formula (IC)
Implementation Method 4
adjusting the pH of the aqueous mixture to a first pH value that is between 6 and 10 to obtain a first organic phase that comprises the compound of formula (IC) and a first aqueous phase that comprises a salt of compound of formula (I)
Data Source
AI summary
The invention relates to terpene-derived compounds, such as acids, esters thereof, produced by ozonolysis of terpenes, and to alcohols, amides, nitriles derived therefrom, as well as to processes for synthesizing them. Specifically, 2,3,7-trimethyloct-6-en-2-ol, 2,3,7-trimethyloct-7-en-2-ol, or a mixture thereof, produced by Grignard reaction of a terpene derived carboxylate with methyl magnesium bromide is disclosed.