Suberic Acid Synthesis from Renewable Feedstocks

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Solution Overview

Problem

The lack of commercially available suberic acid limits the production of polymers with specific properties, as it is difficult to obtain from conventional petroleum-based feedstocks, restricting the availability of polymers with properties between those of adipic and sebacic acid-based polymers.

Innovation Solution

A method is developed to isomerize 9-decenoic acid methyl ester to form suberic acid using a fluorosulfonic acid group, followed by oxidation, which allows for the production of suberic acid from renewable feedstocks, reducing the need for undesirable solvents and side products.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If suberic acid is produced from conventional petroleum-based feedstocks, then production is possible, but the process is difficult and commercially unavailable

Engineering Contradiction:

Improveease of suberic acid productionVSAvoidavailability of renewable feedstocks

Core Design Contradiction:

Ease of manufactureVSAdaptability or versatility

Solution Approach 1:

The patent changes the feedstock parameter from petroleum-based to renewable sources (natural oils, fatty acid methyl esters). This parameter change enables suberic acid production through a new pathway: metathesis to produce terminal olefin esters, followed by isomerization to internal olefin esters, and oxidation to suberic acid, resolving the manufacturing difficulty while maintaining commercial viability

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent introduces intermediary compounds (terminal olefin esters and internal olefin esters) as mediators between the renewable feedstocks and suberic acid. These intermediaries facilitate the transformation by providing stable, isolatable stages in the synthesis pathway, making the overall process more controllable and manufacturable

Inventive Principle:

Principle #24Intermediary (Mediator)

2Productivity

If conventional methods are used to produce dicarboxylic acids, then adipic and sebacic acids are readily available, but suberic acid (C8) is not commercially available

Engineering Contradiction:

Improvecommercial availability of dicarboxylic acidsVSAvoidavailability of C8 dicarboxylic acid

Core Design Contradiction:

ProductivityVSQuantity of substance

Solution Approach 1:

The patent segments the production process into distinct stages: metathesis reaction to form terminal olefin esters, isomerization to form internal olefin esters, and oxidation to produce suberic acid. This segmentation allows each step to be optimized independently and enables the production of suberic acid (C8) which fills the gap between commercially available C6 (adipic) and C10 (sebacic) acids

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The patent creates a universal production pathway that can be applied to produce various dicarboxylic acids by adjusting the feedstock and reaction conditions. The same metathesis-isomerization-oxidation sequence can produce different chain-length dicarboxylic acids, making the process universally applicable while specifically enabling suberic acid production

Inventive Principle:

Principle #6Universality (Multi-functionality)

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 enables the production of suberic acid from renewable sources, providing a more cost-effective and sustainable route to produce polymers with unique properties, such as lubricants and greases, while reducing environmental impact.

Implementation Method 1

combining a substance including a terminal alkenyl group and a substance including a fluorosulfonic acid group in a reaction mixture, and forming a substance including a 2-alkenyl group from the substance including a terminal alkenyl group in the reaction mixture

Methodology Applied

Scientific EffectCatalysis: Catalysis

Implementation Method 2

combining the 8-decenoic acid methyl ester and an oxidizing agent in a second reaction mixture, and forming suberic acid from the 8-decenoic acid methyl ester in the second reaction mixture

Methodology Applied

Scientific EffectOxidation: Oxidation

Data Source

PatentUS10519088B2Methods of making functionalized internal olefins and uses thereof

Publication Date: 2019.12.31 WILMAR TRADING PTE LTD

AI summary

A method of isomerizing methyl 9-decenoate in a reaction mixture, and forming methyl 8-decenoate, and reacting the methyl 8-decenoate by metathesis to form 1,16-dimethyl 8-hexadecenedioate, and hydrogenating 1,16-dimethyl 8-hexadecenedioate to form 1,16-dimethyl hexadecanedioate. In some embodiments, the 1,16-dimethyl hexadecanedioate can be converted to hexadecanedioic acid.