Biobased adipic acid

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Type of post: Fact sheet.
Series: Biobased chemicals – Organic acids.
Publication date: 25/05/2021. Last update: 25/05/2021.

Description
- C6 aliphatic dicarboxylic acid.
- White crystalline powder.
- Other names: hexanedioic acid; 1,4-butanedicarbocylic acid.


Applications
- Monomer for the production of nylon 6,6.
- Monomer for the production of polyurethane.
- Manufacture of plasticizers and lubricants.
- Gelling and acidulant agent (food grade).

Conventional petrochemical route
- Oxidation of cyclohexane to produce KA oil (cyclohexanone and cyclohexanol) / Nitric acid oxidation of KA oil. During the final reaction, the highly potent GHG nitrous oxide (N2O, 300 times more potent than carbon dioxide) is formed. It has been estimated that replacing the current petrochemical-based process with one employing renewable precursors will reduce greenhouse gas emissions by up to 95%, depending on the process used (1).

Main biobased routes
- [Muconic acid via] Fermentation of sugars to produce muconic acid / Hydrogenation.
- Direct fermentation.
- [Glucaric acid via] Anaerobic oxidation of sugar to produce glucaric acid / Hydrodeoxygenation of glucaric acid.

Actors – Active projects
- Genomatica (2,3)
It has a program focusing on polyamide intermediates and bio-nylon, including adipic acid.
- Additional note. Aemetis (through the acquisition of Draths Corporation in 2011), Amyris (through the acquisition of Draths Corporation in 2011) and Deinove (through its muconic acid production program) have the potential to develop adipic acid production routes based on fermentation but there have been no official declarations from their side.

Actors – Suspended/idle projects
- Bioamber (2)
In 2011, BioAmber entered into an exclusive licensing agreement with Celexion for technology related to the production of adipic acid. BioAmber built an in-house research facility in Plymouth (Minnesota, USA) to support its adipic acid development. BioAmber shut down in 2018.
- Rennovia [Glucaric acid via] (2,4)
It developed a proprietary chemo-catalytic process using glucose as feedstock. The company operated at pilot scale (4 tons per year) and was targeting construction of a demo and commercial units. In 2013, it produced and shipped samples of the first 100% bio-based nylon 6,6 polymer under the RENNLON™ brand. Both demo and commercial plants were expected to be developed with external partnerships, including an announced collaboration with Johnson Matthey Davy in 2015. Rennovia shut down in 2018.
- Verdezyne [Direct fermentation] (2,4)
The American biotech company Verdezyne developed a yeast that can produce adipic acid from vegetable oils and sugars in a single step. In 2011, Verdezyne opened a pilot facility in California for the production of adipic acid (5-15 kg per week). A number of major industrial parties including DSM and BP were partners in this project. Verdezyne shut down in 2018.

Market
- Global adipic acid production in 2018: 3 Mtons (4). All acrylic acid capacity is based on the two-stage oxidation of propylene route.
- Global biobased adipic acid production: Not commercial production. Some of the most promising actors have disappeared in the last few years.

References
(1) E. Skoog, J.-H. Shin, V. Saez-Jimenez, V. Mapelli, L. Olsson: "Biobased adipic acid – The challenge of developing the production host”. Biotechnology Advances, Volume 36, Issue 8, 2018, Pages 2248-2263.
(2) E4tech, RE-CORD and WUR (2015) “From the Sugar Platform to biofuels and biochemicals”. Final report for the European Commission, contract No. ENER/C2/423-2012/SI2.673791.
(3) Genomatica website. 
(4) P. Harmsen, M. Hackmann (2013) “Green building blocks for biobased plastics; biobased processes and market development”.

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