Oleyl Alcohol Production via Direct Hydrogenation

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Solution Overview

Problem

Existing processes for producing oleyl alcohol, a key intermediate in surfactant synthesis, require energy-intensive distillation steps and generate waste fractions, making them inefficient and environmentally costly.

Innovation Solution

A process involving the hydrogenation of fatty acids or their methyl esters from a mixture of palm oil and sunflower seed oil variants, bypassing distillation, to produce oleyl alcohol, which is then converted into surfactants like oleyl sulfate and oleyl ethoxylate without the need for distillation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If distillation is used to fractionate fatty acids or methyl esters to produce oleyl alcohol, then the purity and composition of the product can be controlled, but energy consumption increases significantly and waste fractions are generated

Engineering Contradiction:
Improveproduct composition controlVSAvoidenergy consumption
Core Design Contradiction:
Manufacturing precisionVSUse of energy by moving object

Solution Approach 1:

The patent extracts and removes the distillation step from the conventional process sequence. By selecting specific oil feedstocks with predetermined fatty acid compositions (high oleic acid content), the process obtains oleyl alcohol through direct hydrogenation without requiring fractional distillation to separate oleyl alcohol from other fatty alcohols, thereby eliminating the energy-intensive separation step while maintaining product composition control

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the feedstock parameters by selecting oils with specifically high oleic acid content (such as high oleic sunflower oil, olive oil, or rapeseed oil variants) and controlling the oleic acid content in the feedstock to be at least 60 wt%. This parameter change in the input material composition allows the hydrogenation process to directly produce oleyl alcohol with the desired composition without requiring subsequent distillation for fractionation

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If distillation is used to fractionate fatty acids or methyl esters to produce oleyl alcohol, then the purity and composition of the product can be controlled, but waste fractions are generated

Engineering Contradiction:
Improveproduct composition controlVSAvoidwaste generation
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The patent removes the distillation fractionation step that generates waste fractions. By using feedstocks with high oleic acid content and directly hydrogenating them, the process produces oleyl alcohol as the main product without generating significant waste fractions that would require disposal or further processing

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent eliminates the need to discard waste fractions by selecting feedstocks where the natural composition aligns with the desired product specification. The hydrogenation of high oleic acid oils produces predominantly oleyl alcohol, allowing the process to recover and utilize essentially all of the feedstock material in the final product without generating discardable waste streams

Inventive Principle:
Principle #34Discarding and recovering

3Manufacturing precision

If complex fractionation processes are used to produce oleyl alcohol, then product specifications can be met, but process complexity increases

Engineering Contradiction:
Improveproduct specification complianceVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent extracts and eliminates the complex fractionation and distillation equipment from the process flow. By controlling the feedstock composition (oleic acid content ≥60 wt%) and using direct hydrogenation, the process achieves product specification compliance with a simple two-step process: transesterification (optional) followed by hydrogenation, removing the need for complex separation equipment

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent performs preliminary selection and preparation of feedstocks with high oleic acid content before the hydrogenation step. By pre-selecting oils such as high oleic sunflower oil, olive oil, or rapeseed oil variants with at least 60 wt% oleic acid, and optionally performing transesterification to convert triglycerides to methyl esters, the process ensures that the subsequent hydrogenation directly produces oleyl alcohol meeting specifications without requiring complex downstream fractionation equipment

Inventive Principle:
Principle #10Preliminary action

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 simplifies the production of oleyl alcohol and surfactants, reducing energy consumption and waste generation while maintaining the desired fatty acid composition, thus improving the efficiency and sustainability of surfactant production.

Implementation Method 1

hydrogenation of a fatty acid, a fatty acid methyl ester or a combination thereof to provide a fatty alcohol

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentEP4259597B1Process to produce oleyl alcohol
Publication Date: 2024.07.24 UNILEVER IP HLDG BV
  • EP4259597B1 patent drawing
  • EP4259597B1 patent drawing

AI summary

The invention concerns an oleyl alcohol, wherein the oleyl chain is obtained from a mixture of 1:9 to 6:4, preferably 2:8 to 5:5 of oil (1) : oil (2) by hydrogenation of a fatty acid, a fatty acid methyl ester or a combination thereof to provide a fatty alcohol, where oil (1) is selected from palm oil, cottonseed oil or a mixture thereof, and oil (2) is selected from tall oil, olive oil, low erucic rapeseed oil, sunflower seed oil variants containing greater than 60 wt.% oleic acid or mixtures thereof; and a process to make said oleyl alcohol.