Institute of Chemical Research of Catalonia

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

Posted by Institute of Chemical Research of CataloniaResponsive · Patents for licensing · Spain

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.

Institute of Chemical Research of Catalonia

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
EP17382245
Europe

Patent already applied for
EP18382041
Europe

Technology Owner

Institute of Chemical Research of Catalonia

Technology Transfer Office

Related keywords

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

About Institute of Chemical Research of Catalonia

Technology Transfer Office from Spain

The Institute of Chemical Research of Catalonia represents one of the very first fruits of the new scientific policy of the government of Catalonia (Spain) aimed at creating new research centres in strategic areas. ICIQ, in particular, has been created with the ambition of becoming a reference for chemistry in the European Research Space.

Our society faces important challenges in the XXI century, among which health and environmental concerns are of outmost importance. Chemistry will play an essential role in both of these challenges. To succeed, our increasingly knowledge-based economy will require a solid and strong chemical industry; currently 150.000 jobs in Catalonia (and more than 2 million in the EU) directly arise from the chemical industry. In order for this industry to be successful in the future, it must take a sustainable approach based on the rational use of feed-stocks and raw materials. For this, fundamental chemical research needs to be funded and novel approaches into transforming matter must be developed.

We at ICIQ consider that catalysis is the key activity for sustainable chemistry. Catalytic processes can minimize raw materials and energy consumption, and can lead to the selective formation of target products with minimal generation of wastes. In line with this consideration, we have taken catalysis as one of our main research topics.

Complementary to our research focus, attention has been paid to the development of a simple and efficient organizational model for ICIQ, able to overcome known difficulties normally associated with larger and more traditional research institutions. The Institute of Chemical Research of Catalonia aims at bridging the gap between academic research and industry, focusing its research on catalytic chemical processes for applications in health, energy and sustainability.

At ICIQ, we consider that patents are highly efficient, safe and solid tools to provide protection from competitors. This is why we file patents for our in-house developed-technologies: to give our co-development projects with industry a strong starting IP position. As a research centre our goal is always to co-develop our technology adapting it to the industrial partner’s specific needs and ultimately transfer the technology to this company, with a flexible licensing strategy adapted to each case.

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