Linear Alkane Production via Microbial Chain Elongation

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Solution Overview

Problem

Current methods for producing higher linear alkanes, such as undecane, from renewable sources are inefficient and do not effectively reduce carbon dioxide emissions, which are required to meet regulatory standards for the transport sector.

Innovation Solution

A combined biotechnological and chemical method involving the use of microorganisms like Clostridium kluyveri to elongate carbon chains from ethanol and lower alkanoic acids, followed by extraction with alkyl-phosphine oxide and trialkylamine, ketonization, hydrogenation, and dehydration to produce linear alkanes.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional methods are used to produce higher linear alkanes, then the production process is simple, but the yield is low and end-product inhibition occurs

Engineering Contradiction:
ImproveyieldVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The production process is divided into multiple discrete steps: (a) microbial carbon chain elongation to produce intermediate alkanoic acids, (b) extraction of intermediates using alkyl-phosphine oxide, (c) ketonization to form linear alkanones, (d) hydrogenation to produce secondary linear alkanols, (e) dehydration to form linear alkenes, and (f) final hydrogenation to yield linear alkanes. This segmentation allows each step to be optimized independently, preventing end-product inhibition and improving overall yield.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent employs extraction using alkyl-phosphine oxide to remove intermediate alkanoic acids from the microbial fermentation medium. This extraction step prevents accumulation of intermediates that would otherwise inhibit microbial growth and product formation, thereby maintaining high yield and productivity throughout the process.

Inventive Principle:
Principle #2Taking out (Extraction)

2Object-affected harmful factors

If conventional methods are used, then the process is straightforward, but carbon dioxide emissions are not effectively reduced

Engineering Contradiction:
Improvecarbon dioxide emissionsVSAvoidproduction efficiency
Core Design Contradiction:
Object-affected harmful factorsVSProductivity

Solution Approach 1:

The patent utilizes microorganisms capable of carbon chain elongation to convert carbon dioxide and hydrogen into higher alkanoic acids with extended carbon chains. This biochemical transformation changes the molecular parameters of carbon compounds, creating longer-chain alkanes that serve as efficient fuel alternatives while sequestering carbon dioxide and reducing emissions.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If simple extraction agents are used, then the extraction process is simple, but extraction efficiency is insufficient

Engineering Contradiction:
Improveextraction efficiencyVSAvoidextraction system complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent introduces alkyl-phosphine oxide as an intermediary extraction agent that selectively interacts with intermediate alkanoic acids. This intermediary substance forms soluble complexes with the intermediates, enabling efficient extraction from the fermentation medium while maintaining a relatively simple extraction system that can be easily separated and reused.

Inventive Principle:
Principle #24Intermediary (Mediator)

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 increases yield and reduces end-product inhibition, allowing for the efficient production of higher linear alkanes like undecane from renewable sources, thereby addressing carbon emissions and meeting regulatory requirements.

Implementation Method 1

contacting ethanol and/or a linear alkanoic acid comprising 2 to 5 carbon atoms or any salts thereof with at least one microorganism capable of carrying out two-carbon chain elongation to produce as an intermediate a linear alkanoic acid comprising 4 to 7 carbon atoms

Methodology Applied
Scientific EffectCarbon chain elongation:

Implementation Method 2

extracting the intermediate, its salt and/or ester thereof from (a) using at least one extractant, wherein the extractant comprises at least one alkyl-phosphine oxide and optionally at least one alkane comprising at least 12 carbon atoms

Methodology Applied
Scientific EffectLiquid-liquid extraction: Liquid-Liquid Extraction

Implementation Method 3

contacting the extracted intermediate and/or ester thereof from (b) and optionally a further alkanoic acid comprising 1 to 22 carbon atoms with at least one ketonization catalyst to a linear alkanone comprising 7 to 28 carbon atoms

Methodology Applied
Scientific EffectKetonization: Oxidation

Implementation Method 4

contacting the linear alkanone comprising 7 to 28 carbon atoms from step (c) with at least one hydrogenation metal catalyst for catalytic hydrogenation of the linear alkanone comprising 7 to 28 carbon atoms to a corresponding secondary linear alkanol comprising 7 to 28 carbon atoms

Methodology Applied
Scientific EffectCatalytic hydrogenation: Hydrogenation

Implementation Method 5

dehydration of the secondary alkanol in the presence of an acidic heterogeneous catalyst to form a corresponding linear alkene comprising 7 to 28 carbon atoms

Methodology Applied
Scientific EffectDehydration:

Implementation Method 6

contacting the linear alkene comprising 7 to 28 carbon atoms obtained in step (e) with at least one hydrogenation metal catalyst for catalytic hydrogenation to a corresponding secondary linear alkane comprising 7 to 28 carbon atoms

Methodology Applied
Scientific EffectCatalytic hydrogenation: Hydrogenation

Data Source

PatentUS20240191264A1Method for producing higher linear alkanes
Publication Date: 2024.06.13 EVONIK OPERATIONS GMBH
  • US20240191264A1 patent drawing
  • US20240191264A1 patent drawing

AI summary

The present invention relates to a method of producing higher linear alkanes using a combined biotechnological and chemical method. In particular, the present invention relates to producing linear alkanes comprising 7 to 28 carbon atoms, preferably undecane, via higher alkanones, i.e. linear alkanones comprising 7 to 28 carbon atoms, preferably 6-undecanone.