Guerbet Condensation n-Hexanol Recovery for Higher Alcohol Yield

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Solution Overview

Problem

The existing processes for Guerbet condensation of ethanol to produce n-butanol result in significant amounts of n-hexanol, which has limited industrial applicability, necessitating the development of improved methods to maximize n-butanol and n-octanol production while minimizing n-hexanol generation.

Innovation Solution

A method involving a reaction mixture with a source of ethanol, hydrogen, and recovered n-hexanol, contacted with a Guerbet catalyst in a gas phase reactor at specific temperature and pressure conditions, to enhance the selectivity and yield of n-butanol and n-octanol, using a catalyst comprising bivalent, trivalent metals, and noble metals, and optionally vanadium or gallium.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If Guerbet condensation of ethanol is carried out to produce n-butanol, then n-butanol is obtained as a valuable fuel additive, but significant amounts of n-hexanol are produced as a byproduct which has limited industrial applicability and lower value

Engineering Contradiction:
Improven-butanol productionVSAvoidn-hexanol byproduct
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent converts the harmful byproduct n-hexanol into a valuable reactant by feeding it back into the Guerbet condensation reactor along with ethanol. This transforms the waste stream into a useful input that contributes to producing higher-value products (n-octanol and n-decanol), thereby eliminating the need to dispose of n-hexanol and converting it from a liability into an asset.

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

Solution Approach 2:

Instead of discarding n-hexanol as waste, the patent recovers it through fractionation and reintroduces it to the reaction system. This recovery process transforms a low-value byproduct into a precursor for higher-value C8 and C10 alcohols, improving overall process efficiency and product value.

Inventive Principle:
Principle #34Discarding and recovering

2Manufacturing precision

If conventional Guerbet catalysts are used for ethanol condensation, then n-butanol is produced, but the selectivity is low and significant n-hexanol is generated

Engineering Contradiction:
Improveselectivity to n-butanolVSAvoidoverall higher alcohol yield
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent employs a composite catalyst system comprising multiple metal oxides (such as ZnO, Cr2O3, Al2O3) combined with noble metals (Pd, Pt, Rh, or Ru). This composite catalyst structure synergistically enhances both the selectivity to n-butanol and the productivity for higher alcohol formation, resolving the contradiction between precision and output.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent optimizes reaction parameters including temperature (200-400°C), pressure (1-50 bar), and the molar ratio of ethanol to n-hexanol in the feed. By carefully controlling these parameters, the process achieves high selectivity to n-butanol while simultaneously maximizing the production of C8 and C10 alcohols, thus improving both manufacturing precision and productivity.

Inventive Principle:
Principle #35Parameter changes

3Loss of energy

If n-hexanol is incinerated for energy recovery, then energy is recovered, but the process complexity increases and the value of the byproduct is minimized

Engineering Contradiction:
Improveenergy recoveryVSAvoidprocess complexity
Core Design Contradiction:
Loss of energyVSDevice complexity

Solution Approach 1:

The patent makes the process self-sufficient by using the byproduct n-hexanol as a fuel source within the same system. The heat generated from partial oxidation or combustion of n-hexanol is utilized to maintain reaction temperature, eliminating the need for external energy input and reducing process complexity compared to separate incineration systems.

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

The patent merges the energy recovery function with the chemical transformation function by integrating n-hexanol utilization directly into the Guerbet condensation process. Instead of separate incineration and synthesis units, the system combines these functions, reducing overall process complexity while maintaining energy efficiency.

Inventive Principle:
Principle #5Merging (Combining)

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 approach increases the production of n-butanol and n-octanol while reducing n-hexanol production, optimizing the yield and selectivity of higher alcohols through controlled reaction conditions and catalyst composition.

Implementation Method 1

The reaction mixture is contacted with a Guerbet catalyst in a gas phase reactor

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

catalytic condensation of ethanol to n-butanol can be carried out

Methodology Applied
Scientific EffectDehydrogenation: Hydrogenation

Implementation Method 3

Guerbet condensation of ethanol to produce n-butanol

Methodology Applied
Scientific EffectAldol condensation:

Implementation Method 4

catalytic condensation of ethanol to n-butanol

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 5

The reactor product stream is fractionated to form the recovered n-hexanol, a n-butanol product stream and a n-octanol product stream

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentEP3218339B1Process for the preparation of higher alcohols from ethanol and n-hexanol by guerbet condensation
Publication Date: 2022.01.05 ABENGOA BIOENERGIA NUEVAS TECHAS
  • EP3218339B1 patent drawingFigure 1
  • EP3218339B1 patent drawingFigure 2
  • EP3218339B1 patent drawingFigure 3

AI summary

The present disclosure generally relates to processes for preparation of n-butanol, n-octanol and n-decanol from a reaction mixture comprising ethanoi and n-hexanol by Guerbet condensation. In some aspects, the present disclosure relates to improvements in n-octanol and n-decanol yield and selectivity by the selection of process reaction conditions such as, but not limited to, mole ratio of n-hexanol to ethanol. The present disclosure further generally relates to integrated processes for preparation of n-butanol in a n-butanol reactor from a reaction mixture comprising ethanol and hydrogen to produce a n-butanol product stream by Geurbet condensation comprising n-butanol and n-hexanol and for preparation of n-octanol in a n-octanol reactor from a reaction mixture comprising ethanol, n-hexanol and hydrogen to produce a n-octanol product stream by Geurbet condensation comprising n-butanol, n-hexanol and n-octanol. A predominant proportion of the n-hexanol contained in the n-butanol and n-octanol product streams is isolated and recycled to the n-octanol reaction mixture. In some aspects, the present disclosure relates to improvements in n-octanol and n-butanol yield and selectivity by the selection of process reaction conditions such as, but not limited to, mole ratio of n-hexanol to ethanol and recovery and recycle of n-hexanol.