Summary of the technology
Adipic acid is mainly used industrially in the production of nylon 6,6. The offered technology consists in a nickel catalyzed process of carboxylation of butadiene. The developed process allows preparing adipic acid from carbon dioxide and 1,3-butadiene through a cost effective and competitive process. Industrial partners are sought for process optimization and/or industrialization.
Typically, adipic acid is currently industrially obtained by the treatment of KA oil with nitric acid which itself dervies from cyclohexane. The current process presents several drawbacks:
- KA oil is rather expensive (ca. 2000 €/ton)
- The process generates contaminating NOx species
Direct carboxylation of 1,3-butadiene(s) is a long sought after process, as such a process would consume carbon dioxide on the one hand (CO2 is responsible for greenhouse gas effect) and would use an easily available and affordable starting material (1,3-butadiene costs about 1200 €/ton). We have discovered a new catalytic process, using cheap and abundant metal species (nickel) allowing for the dicarboxylation of 1,3-butadiene to an unsaturated adipic acid derivative which can then undergo hydrogenation to provide adipic acid in 61% yield over the two steps. We expect the implementation of this process to significantly decrease operational expenses of adipic acid production.
The developed process for adipic acid production proceeds in two steps: (i) dicarboxylation and (ii) hydrogenation (typical catalytic hydrogenation can be used in this step). The dicarboxylation step occurs in the following conditions: catalytic amounts of NiBr4 · TBA2 (equivalent to NiBr2 and bromide salts), catalytic amounts of a bathophenanthroline derived ligand, reducing agent (e.g. stoichiometric amounts of Manganese), 50 ºC, atmospheric pressure of carbon dioxide.
- shortened value chain
- green process (consumes a contaminating waste)
- cheaper method
- higher substrate scope
Production of polyamides, Production of nylon 6,6, Uses of carbon dioxide
The market for adipic acid is currently experimenting an average growth of 3.7% annually, reaching a value estimated at more than $7,5 billions for year 2019 worldwide. The implementation of a cost effective production process for adipic acid would have benefitial impact on the competitiveness, market share and profits of a company.
Desired business relationship
Current development status
Intellectual property status
Patent already applied for
Patent already applied for
About Institut Català d'Investigació Química (ICIQ)
Technology Transfer Office from SpainInstitut Català d'Investigació Química (ICIQ)
ICIQ is a leading R&D institute based in Tarragona (Spain) dedicated to the development of excellent research in the fields of chemistry and catalysis.