Norbornene Ester Fragrance via Diels-Alder Synthesis

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Solution Overview

Problem

Natural fragrance compounds face challenges such as inconsistent quality, high costs due to low yield, and toxicity, necessitating the development of cost-effective, non-toxic, and environmentally friendly synthetic alternatives that maintain uniform quality and reduce waste.

Innovation Solution

The use of functionalized norbornene ester derivatives, specifically compounds of formulas (IA), (IB), and (IC), in combination with fragrance carriers and adjuvants, to create a fine fragrance composition that can be tailored for various perfumed products, enhancing or modifying odor properties through Diels-Alder reactions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If natural fragrance compounds are used, then pleasant aroma is achieved, but quality consistency deteriorates due to batch-to-batch variation

Engineering Contradiction:

Improvequality consistencyVSAvoidbatch-to-batch variation

Core Design Contradiction:

ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent creates synthetic copies of natural fragrance compounds through Diels-Alder reactions, producing identical molecular structures (norbornene derivatives) that replicate the desired aromatic properties while eliminating the variability inherent in natural extraction processes

Inventive Principle:

Principle #26Copying

Solution Approach 2:

The patent systematically varies chemical parameters including substituent groups (R1-R6), position isomers (exo/endo), and ester chain lengths to optimize fragrance properties while maintaining consistent quality through controlled synthesis rather than natural variation

Inventive Principle:

Principle #35Parameter changes

2Reliability

If natural fragrance compounds are extracted from natural sources, then aromatic properties are obtained, but production cost increases due to low yield

Engineering Contradiction:

Improvearomatic propertiesVSAvoidproduction cost

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

Instead of extracting fragrance compounds from expensive natural sources, the patent synthesizes copies using inexpensive starting materials (cyclopentadiene and dienophiles) through efficient Diels-Alder reactions, dramatically reducing production costs while maintaining aromatic quality

Inventive Principle:

Principle #26Copying

Solution Approach 2:

The patent optimizes synthesis parameters including reaction temperature, catalyst selection, and substituent patterns to maximize yield and minimize production costs while preserving the desired fragrance characteristics

Inventive Principle:

Principle #35Parameter changes

3Reliability

If natural fragrance compounds are used, then desirable scent is achieved, but environmental harm increases due to toxicity and waste

Engineering Contradiction:

Improvescent qualityVSAvoidtoxicity and waste

Core Design Contradiction:

ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent creates synthetic alternatives that copy the beneficial aromatic properties of natural compounds while eliminating the toxic components and environmental harm associated with natural extraction and purification processes

Inventive Principle:

Principle #26Copying

Solution Approach 2:

The patent converts the limitations of natural sources (toxicity, waste) into benefits by using green chemistry principles in the synthesis process, producing non-toxic norbornene derivatives through atom-efficient Diels-Alder reactions that generate minimal waste

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

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 solution provides a consistent, cost-effective, and environmentally friendly fragrance composition that maintains uniform quality, reduces waste, and is non-toxic, suitable for a wide range of perfumed products, including perfumes, colognes, and personal care items.

Implementation Method 1

enhancing or modifying odor properties through Diels-Alder reactions

Methodology Applied

Scientific EffectDiels-Alder reaction: Chemical Bonding

Data Source

PatentUS11549080B2Fine fragrance compositions containing norbornene ester derivatives

Publication Date: 2023.01.10 SUMITOMO BAKELITE CO LTD

AI summary

Embodiments in accordance with the present invention relate generally to a variety of norbornene derivatives exhibiting olfactive properties and are suitable as fine fragrance ingredients. More specifically, this invention relates to various fragrance compositions containing one or more of a compound of formulae (IA) to (IC):Wherein m, n, R1, R2, R3, R4, R5 and R6 are as defined herein. The compounds of formulae (IA) to (IC) are useful as perfumes, colognes, and in perfume augmenting, modifying, enhancing, and imparting compositions. The compositions of this invention are therefore useful in a variety of products including perfumes, colognes, soaps, detergents, candles, air fresheners, trash bags, tissues, deodorants, lotions, skin care products, hair products, sanitary products, cleaning products, and the like.