3-Phenylpropan-1-ol Production from Natural Cinnamaldehyde

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Solution Overview

Problem

Current methods for producing 3-phenylpropan-1-ol from cinnamaldehyde are hazardous to living organisms and the environment, require extensive purification steps, and rely on petrochemical starting materials, which are harmful and inefficient.

Innovation Solution

A process to produce 3-phenylpropan-1-ol from cinnamaldehyde derived from natural sources, such as essential oils and plant extracts with high cinnamaldehyde content, using catalytic hydrogenation with a nickel catalyst and subsequent purification by alkaline water extraction and distillation, avoiding the need for extensive purification and reducing environmental impact.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If cinnamaldehyde is obtained from natural sources through extensive purification steps, then purity is improved, but manufacturing complexity and time are worsened

Engineering Contradiction:
ImprovepurityVSAvoidmanufacturing complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent performs preliminary concentration of cinnamaldehyde in the natural starting material to at least 80 wt.% before hydrogenation. This preliminary action eliminates the need for extensive purification steps after hydrogenation, as the concentrated starting material directly yields high-purity phenylpropanol after a single distillation step, thereby reducing manufacturing complexity while maintaining high purity.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent extracts and concentrates cinnamaldehyde from natural sources to obtain a starting material with at least 80 wt.% cinnamaldehyde content. This extraction and concentration step removes impurities beforehand, allowing the hydrogenation process to proceed cleanly without requiring complex post-purification procedures.

Inventive Principle:
Principle #2Taking out (Extraction)

2Productivity

If conventional hydrogenation uses precious metal or transition metal catalysts, then reaction efficiency is improved, but cost and environmental impact are worsened

Engineering Contradiction:
Improvereaction efficiencyVSAvoidenvironmental impact
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent replaces expensive and environmentally problematic precious metal or transition metal catalysts with a simple, inexpensive, and environmentally benign nickel catalyst. The nickel catalyst achieves the same hydrogenation function without the harmful environmental impact and high cost associated with precious metals, making the process both economically viable and environmentally friendly.

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

Solution Approach 2:

The patent changes the catalyst parameter from precious metal or transition metal to nickel, which is abundant, inexpensive, and environmentally benign. This parameter change maintains reaction efficiency while eliminating the environmental harm and high cost associated with rare metals.

Inventive Principle:
Principle #35Parameter changes

3Quantity of substance

If aldol condensation is used to produce cinnamaldehyde, then production volume is improved, but yield and selectivity are worsened

Engineering Contradiction:
Improveproduction volumeVSAvoidyield
Core Design Contradiction:
Quantity of substanceVSManufacturing precision

Solution Approach 1:

Instead of synthesizing cinnamaldehyde through aldol condensation (which gives only 70-80% yield and poor selectivity), the patent inverts the approach by obtaining cinnamaldehyde directly from natural sources where it occurs abundantly. This inversion eliminates the low-yield synthesis step and provides both high production volume and high purity cinnamaldehyde starting material.

Inventive Principle:
Principle #13The other way round (Inversion)

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 provides an industrially feasible, environmentally friendly, and efficient production of 3-phenylpropan-1-ol with high purity and low allergen potential, suitable for use in perfumes, personal care products, and other applications, while minimizing the use of hazardous petrochemicals.

Implementation Method 1

conversion of cinnamaldehyde in starting material to 3-phenylpropan-1-ol by a catalytic hydrogenation

Methodology Applied
Scientific EffectCatalytic hydrogenation: Hydrogenation

Implementation Method 2

catalysed by Molybdenum-promoted sponge Nickel catalysts

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

distillation of 3-phenylpropan-1-ol

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 4

purification of the 3-phenylpropan-1-ol by alkaline water extraction

Methodology Applied
Scientific EffectExtraction: Liquid-Liquid Extraction

Data Source

PatentUS11739036B2Process to obtain 3-phenylpropan-l-ol from natural sources
Publication Date: 2023.08.29 MINASOLVE SOLUTIONS SPRL

AI summary

The present invention relates to a process for the manufacturing of 3-phenylpropan-1-ol, from nature derived starting material, wherein said nature derived starting material comprises not less than 80 wt. % of cinnamaldehyde. In another aspect, the present invention relates to the process, which further comprises the steps: a) conversion of cinnamaldehyde as starting material to 3-phenylpropan-1-ol by a catalytic hydrogenation; b) optional purification of the 3-phenylpropan-1-ol by alkaline water extraction; c) distillation of 3-phenylpropan-1-ol. In a third aspect the present invention relates to use of 3-phenylpropan-1-ol obtained by the process of the invention in perfumes and/or personal care and/or cleaning products.