Biological Pathways for Dodecanedioic Acid

Introduction

Dodecanedioic acid (DDDA) is a 12-carbon aliphatic dicarboxylic acid with key applications in high-performance nylons (e.g., nylon-6,12), polyesters, adhesives, lubricants, and resins. Traditionally, DDDA is produced from petroleum-derived butadiene or through ozonolysis of cyclododecatriene, which are energy-intensive and environmentally hazardous.

With increasing focus on sustainable materials, biological production of DDDA has gained attention as a green alternative. Using engineered microbes, DDDA can be produced from renewable fatty acids or alkanes, converting biomass-derived feedstocks into long-chain dicarboxylic acids via ω-oxidation pathways

What Products Are Produced?

• Dodecanedioic acid (DDDA) – Bio-based version
• Applications:
• Nylon-6,12 and other specialty nylons
• Thermoplastic polyesters and polyurethanes
• Adhesives, coatings, and lubricants
• High-performance automotive and aerospace parts

Pathways and Production Methods

1. ω-Oxidation of Lauric Acid

• Lauric acid (C12) → ω-hydroxy lauric acid → ω-aldehyde → dodecanedioic acid
• Catalyzed by a series of monooxygenases, alcohol dehydrogenases, and aldehyde dehydrogenases

2. Alkane Oxidation

• Dodecane (from paraffin wax or waste plastics) → DDDA via terminal oxidation
• Utilizes alkane-degrading microbes like Candida tropicalis or Yarrowia lipolytica

3. Fatty Acid Fermentation

• Glucose → fatty acid biosynthesis → C12 fatty acid → DDDA
• Engineered microbes channel fatty acid intermediates into oxidation pathways

Catalysts and Key Tools Used

Microbial Hosts:

• Candida tropicalis – Strong ω-oxidation pathway
• Yarrowia lipolytica – Tolerant to long-chain fatty acids
• Engineered E. coli and Pseudomonas putida – Fatty acid route optimization

Key Enzymes:

• Cytochrome P450 monooxygenases (CYPs)
• Fatty alcohol oxidase (FAO)
• Aldehyde dehydrogenase (ALDH)
• Acyl-CoA oxidases

Tools:

• Metabolic engineering of peroxisomal pathways
• CRISPR-based control of fatty acid transport and elongation
• Bioprocess design for two-phase systems (oil-water) to enhance substrate solubility

Case Study: Cathay Biotech’s Industrial DDDA Fermentation

Highlights

• Developed robust Candida tropicalis strains for converting lauric acid to DDDA
• Achieved commercial-scale production using vegetable oil-derived feedstocks
• DDDA used to make bio-nylon 6,12 for automotive and electronics sectors

Timeline

• 2005 – R&D begins on microbial long-chain diacid production
• 2010 – First pilot production using coconut oil fatty acids
• 2015 – Commercial facility launched in China
• 2023 – Over 20,000 tons/year of bio-DDDA capacity

Global and Indian Startups Working in This Area

Global

• Cathay Biotech (China) – World leader in bio-DDDA from lauric acid
• Verdezyne (USA) – Used yeast fermentation of plant oils for DDDA
• Evonik Industries (Germany) – R&D on bio-ω-oxidation systems
• DSM – Enzyme screening for selective oxidation of fatty acids

India

• IIT Madras & ICT Mumbai – Pathway engineering for medium-chain ω-oxidation
• CSIR-IICT Hyderabad – Research on biotransformation of coconut oil to diacids
• Praj Industries – Evaluating long-chain dicarboxylic acid integration into oleochemical biorefineries
• Green Refinery Labs (startup) – Working on enzyme consortia for DDDA synthesis

Market and Demand

The global dodecanedioic acid market stood at USD 540 million in 2023, projected to reach USD 780 million by 2030 at a CAGR of ~5.3%. Bio-based DDDA is expected to grow at a higher CAGR of 9–10%, driven by the demand for sustainable nylons and lubricants.

Key Use Segments:

• Engineering nylons (e.g., Nylon 6,12)
• Polyesters and bio-polyurethane
• Lubricants for high-temperature and aircraft applications
• Epoxy curing agents and adhesives

Key Growth Drivers

• Demand for bio-based engineering plastics
• Availability of lauric acid from coconut and palm sources
• Push for green automotive and electronics components
• Biotech breakthroughs in long-chain fatty acid metabolism
• Commercial success of bio-nylons in textiles and industry

Challenges to Address

• Enzyme specificity and overoxidation control
• Handling of hydrophobic substrates in aqueous fermentation
• High oxygen demand for monooxygenase activity
• In India: Need for scale-up and value chain integration with agro-waste

Progress Indicators

• 2005–2010 – ω-oxidation engineering in yeast begins
• 2015 – First industrial bio-DDDA production launched
• 2018 – Enzyme cascades improved for >85% conversion efficiency
• 2022–2023 – Indian labs explore coconut oil derivatives for microbial DDDA
• 2024 – Ongoing efforts to integrate fatty acid and ω-oxidation modules

Lauric acid to DDDA (yeast-based): TRL 8–9 (commercial). Fatty acid biosynthesis route: TRL 5–6 (pilot). In India: Ranges from TRL 4–6, mostly in academic and early pilot stages

Conclusion

Biological production of dodecanedioic acid offers a renewable, eco-friendly route to high-performance nylons, lubricants, and specialty materials, reducing the environmental impact of long-chain diacids. Advances in ω-oxidation, microbial engineering, and oil-based feedstocks are enabling commercial viability.

India’s access to coconut and palm oil streams, combined with growing bio-polymer demand, positions it to become a regional hub for bio-DDDA production, provided infrastructure and policy support align with innovation pipelines.

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