1,2-Pentanediol Production via Heterogeneous Catalyst Hydrogenation

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Solution Overview

Problem

Current methods for producing 1,2-pentanediol from petrochemical sources are economically and ecologically disadvantageous, and existing processes using furfuryl alcohol and furfural result in low yields and unwanted by-products with unpleasant odors, making it challenging to achieve a neutral odor and high purity of 1,2-pentanediol suitable for cosmetic use.

Innovation Solution

A process involving the reaction of furfuryl alcohol or furfural with hydrogen in the presence of a heterogeneous catalyst containing platinum, rhodium, nickel, or iridium metals and carrier materials, such as activated carbon or aluminum oxide, to produce 1,2-pentanediol with high yield and selectivity, minimizing unwanted by-products and achieving a neutral odor.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If 1,2-pentanediol is produced from n-pent-1-ene using peroxides and organic/mineral acids, then the production route is established, but the process creates unpleasant-smelling by-products and requires complex cleaning steps

Engineering Contradiction:
Improveproduction routeVSAvoidunpleasant-smelling by-products
Core Design Contradiction:
Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The patent changes the chemical parameters of the starting material from petrochemical n-pent-1-ene to renewable furfuryl alcohol or furfural, and modifies the reaction conditions by using heterogeneous catalysts instead of peroxides and strong acids. This parameter change eliminates the formation of unpleasant-smelling by-products while maintaining production efficiency

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent extracts and removes the problematic intermediate steps (epoxidation with peroxides, saponification with strong bases) that generate harmful by-products. By using direct hydrogenation/hydrogenolysis of furfuryl alcohol or furfural, the process eliminates these intermediate steps and their associated harmful emissions

Inventive Principle:
Principle #2Taking out (Extraction)

2Productivity

If epoxidation of n-pent-1-ene is carried out with hydrogen peroxide and formic acid, then 1,2-pentanediol can be produced, but sodium formate co-product pollutes wastewater

Engineering Contradiction:
Improve1,2-pentanediol productionVSAvoidwastewater pollution
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent converts the harmful wastewater pollution issue into a benefit by using a catalytic process that does not generate soluble salt by-products. The heterogeneous catalyst can be filtered and reused, and the only by-products are water and unchanged starting materials, which do not pollute wastewater

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

Solution Approach 2:

The patent replaces the mechanical/chemical saponification process (which requires large amounts of water and generates polluting waste) with a catalytic hydrogenation/hydrogenolysis process that operates under milder conditions and produces minimal waste

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

3Ease of manufacture

If n-pent-1-ene is used as raw material, then 1,2-pentanediol production is established, but special protective measures are required due to low boiling point and explosion risk

Engineering Contradiction:
Improveproduction processVSAvoidexplosion risk
Core Design Contradiction:
Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

Instead of using highly reactive n-pent-1-ene that requires stringent safety measures, the patent inverts the approach by using stable, non-volatile furfuryl alcohol or furfural as starting materials. These materials have higher boiling points and do not pose explosion risks under normal handling conditions

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

Solution Approach 2:

The patent uses renewable, readily available furfuryl alcohol from grain waste instead of expensive petrochemical n-pent-1-ene that requires costly safety infrastructure. The renewable starting material is safer and more economical

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

4Productivity

If furfuryl alcohol or furfural is hydrogenated using existing catalysts, then 1,2-pentanediol can be produced, but yields are low and unwanted by-products with unpleasant odors are formed

Engineering Contradiction:
Improve1,2-pentanediol yieldVSAvoidproduct purity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent introduces a specifically designed heterogeneous catalyst as an intermediary that mediates the hydrogenation/hydrogenolysis reaction to selectively produce 1,2-pentanediol. The catalyst comprises platinum, rhodium, nickel, or iridium supported on activated carbon, aluminum oxide, silica gel, or molecular sieves, which controls the reaction pathway to minimize by-products

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent uses composite heterogeneous catalysts combining noble metals (platinum, rhodium, nickel, or iridium) with porous support materials (activated carbon, aluminum oxide, silica gel, or molecular sieves). This composite structure provides both high catalytic activity for 1,2-pentanediol formation and selectivity to reduce unwanted by-products

Inventive Principle:
Principle #40Composite materials

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 process achieves high yields and selectivity of 1,2-pentanediol, reducing unwanted by-products and resulting in a neutral odor, making the product suitable for cosmetic applications while being more environmentally friendly and resource-efficient.

Implementation Method 1

reacting a starting material comprising one or both compounds from the group consisting of furfuryl alcohol and furfural in the presence of a heterogeneous catalyst with hydrogen

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 2

the hydrogenolysis of furfuryl alcohol in the presence of a heterogeneous platinum catalyst gives the desired 1,2-pentanediol in good yield and/or good selectivity

Methodology Applied
Scientific EffectHydrogenolysis: Hydrogenation

Data Source

PatentEP2707351B1Method for producing 1-2-pentanediol
Publication Date: 2019.11.06 SYMRISE GMBH & CO KG
  • EP2707351B1 patent drawing
  • EP2707351B1 patent drawing

AI summary

The invention relates to a method for producing 1-2-pentanediol by reacting a reactant, which comprises one or both compounds from the group comprising furfuryl alcohol and furfural, with hydrogen in the presence a first heterogeneous catalyst.