Adipic acid(s) prepared by catalytic carboxylation of 1,3-butadiene

  • Institut Català d'Investigació Química (ICIQ)
  • From Spain
  • Responsive
  • Patents for licensing

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.

Institut Català d'Investigació Química (ICIQ)
Institut Català d'Investigació Química (ICIQ)

Technology description

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:

  1. KA oil is rather expensive (ca. 2000 €/ton)
  2. 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. 

Specifications

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. 

Innovative aspects

  1. shortened value chain
  2. green process (consumes a contaminating waste)
  3. cheaper method
  4. higher substrate scope

Applications

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

Technology selling

Patent licensing

Technology development

Current development status

Laboratory prototypes

Intellectual property status

  • Patent already applied for
  • Patent application number :EP18382041

  • Patent already applied for
  • Patent application number :EP17382245

Attached documents

Related Keywords

  • Industrial Products
  • Chemicals and Materials
  • Plastic fabricators
  • Commodity chemicals and polymers
  • Industrial chemicals
  • Speciality/performance chemicals

About Institut 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.

Institut Català d'Investigació Química (ICIQ)

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