Dehydro Rose Oxide Purification via Vigreux Distillation

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Dehydro rose oxide, a valuable intermediate in rose oxide production, has been overlooked as a fragrance material due to its formation of undesirable by-products and high production costs associated with purification processes.

Innovation Solution

Dehydro rose oxide is recognized as a potent fragrance material with a distinct green, rosy, metallic odor profile, and can be purified to a high standard using fractional distillation, allowing it to be used effectively in fragrance compositions at a weight ratio of 9:1 to 4:1 with nerol oxide, enhancing the olfactometric odor detection threshold.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If dehydro rose oxide is purified by repeated fractional distillation with high columns containing structured packing, then the purity of dehydro rose oxide is improved, but the production cost and labor intensity increase significantly

Engineering Contradiction:
Improvepurity of dehydro rose oxideVSAvoidproduction cost and labor intensity
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent changes the purification parameters by using a standard Vigreux column instead of high columns with structured packing, and employs a single distillation step instead of repeated fractional distillation. This parameter change achieves sufficient purification (essentially free of off-notes) at much lower cost and labor intensity while maintaining the necessary purity for fragrance applications

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces expensive, complex purification equipment (high columns with structured packing) with a simple, inexpensive Vigreux column. This substitution achieves the required purification level without the high capital investment and operational complexity of the alternative method

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Productivity

If dehydro rose oxide is used as an intermediate for rose oxide production, then the production of rose oxide is enabled, but the production cost increases due to additional purification steps

Engineering Contradiction:
Improveproduction of rose oxideVSAvoidproduction cost
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent makes dehydro rose oxide multi-functional by demonstrating its dual use: it can serve as an intermediate for rose oxide production OR be used directly as a fragrance material. When used directly, the simplified purification process (standard distillation instead of repeated fractional distillation) significantly reduces production costs while still achieving the necessary purity for fragrance applications

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The patent allows dehydro rose oxide to serve its own purpose as a fragrance material rather than requiring conversion to rose oxide. This self-service approach eliminates the need for additional hydrogenation steps and associated costs, making the process more economically attractive when high-quality fragrance material is the goal

Inventive Principle:
Principle #25Self-service

3Quantity of substance

If dehydro rose oxide is used in fragrance compositions, then the olfactory effect is enhanced with lower concentration, but the presence of impurities such as nerol oxide may affect the odor profile

Engineering Contradiction:
Improveconcentration of fragrance materialVSAvoidodor profile quality
Core Design Contradiction:
Quantity of substanceVSManufacturing precision

Solution Approach 1:

The patent optimizes the composition parameters by establishing a specific weight ratio range (9:1 to 4:1) of dehydro rose oxide to nerol oxide. This parameter optimization allows the use of lower concentrations of the potent dehydro rose oxide (enhancing olfactory effect) while accepting the presence of nerol oxide within this ratio range, as the combination produces a desirable odor profile rather than off-notes

Inventive Principle:
Principle #35Parameter changes

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 use of dehydro rose oxide in fragrance compositions provides a powerful, desirable odor profile at lower concentrations, surpassing rose oxide in potency and suitability for consumer products, such as perfumes, detergents, and cosmetics, while reducing production costs through efficient purification methods.

Implementation Method 1

a purification by standard distillation, such as a Vigreux column is sufficient to obtain a mixture consisting essentially of dehydro rose oxide and nerol oxide, which is essentially free of off-notes

Methodology Applied
Scientific EffectFractional distillation: Distillation

Data Source

PatentEP3658655B1Organic compounds
Publication Date: 2022.11.23 GIVAUDAN SA
  • EP3658655B1 patent drawing

AI summary

The use as fragrance ingredient of 4-methylene-2-(2-methylprop-1-enyl)-tetrahydropyran.