2-Phenyl-2-Alkene Nitrites Odour Strength and Manufacturing Complexity

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Solution Overview

Problem

The fragrance industry lacks compounds that can enhance or impart new, pleasant odor notes with low odor thresholds, and existing 2-phenyl-2-alkene nitrites were not recognized for their potential as fragrance ingredients due to their perceived musty unpleasant odour.

Innovation Solution

Certain 2-phenyl-2-alkene nitrites, particularly those with specific structural formulas, are found to have pleasant floral and fresh odour notes with significantly lower odor thresholds than their saturated counterparts, making them suitable for use as fragrance ingredients, and can be used alone or combined with other odorants in various applications.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If 2-phenyl-2-alkene nitrites are used as fragrance ingredients, then the odour strength is improved (7 to 9 times stronger than saturated compounds), but the manufacturing complexity increases due to stereogenic units and isomer separation requirements

Engineering Contradiction:

Improveodour strengthVSAvoidmanufacturing complexity

Core Design Contradiction:

Quantity of substanceVSDevice complexity

Solution Approach 1:

The patent changes the chemical structure parameter from saturated to unsaturated (α,β-unsaturated nitrites), which fundamentally alters the odour properties and increases odour strength 7 to 9 times while maintaining manufacturability through established chemical synthesis routes

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

Instead of separating stereoisomers to achieve pure forms (complex route), the patent inverts the approach by accepting and utilizing mixtures of stereoisomers, thereby simplifying manufacturing while still achieving the desired fragrance effect

Inventive Principle:

Principle #13The other way round (Inversion)

2Manufacturing precision

If stereoisomers are resolved to obtain isomerically pure forms, then the odour quality is improved, but the manufacturing and purification complexity increases

Engineering Contradiction:

Improveisomeric purityVSAvoidpurification complexity

Core Design Contradiction:

Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent inverts the conventional approach by rejecting isomeric purification and instead utilizing mixtures of stereoisomers directly, thereby eliminating complex purification steps while maintaining acceptable fragrance quality

Inventive Principle:

Principle #13The other way round (Inversion)

Solution Approach 2:

The patent accepts temporary presence of multiple stereoisomers during manufacturing without requiring their separation, effectively treating the mixture as an acceptable intermediate state that eliminates the need for expensive and complex purification equipment and processes

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

Data Source

PatentUS9102899B2Organic compounds

Publication Date: 2015.08.11 GIVAUDAN SA

AI summary

The use of 2-phenyl-2-alkene nitriles as fragrance ingredients and fragrance applications comprising them. These fragrance applications can be e.g. perfumes, household products, laundry products, body care products and cosmetics.