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Synthetic process for Cyclohexanone Oxime from Cyclohexane via Photo-catalysis

Status: New

Lab/Organization
Name & address of the Laboratory/Organization CSIR-National Chemical Laboratory (NCL)
Website address https://www.ncl-india.org
Affiliated to which Department/Ministry Council of Scientific and Industrial Research (CSIR)
CSR Registration Number CSR00017422
Registration under 12A
Registration under 80G
Name of the CSR Nodal Dr. Tanmoy Patra
Contact information of CSR Nodal +91-20-2590-2124, t.patra@ncl.res.in
Principal Investigator Dr. Pradip Maity , p.maity@ncl.res.in
https://pradipmaitylab.wixsite.com/phosphite-catalysis
Co- Principal Investigator (Co-PI)
Project Detail
Objective on the basis of need

Cyclohexanone oxime is a bulk fine chemical but its synthesis process need improvement. We established a lab-scale method from cyclohexane solvent as the starting material instead of cyclohexanone. This improvement should increase the efficiency of the process with lower cost of production.

Executive summary of the proposed project (In 250 words)

Cyclohexanone oxime is a bulk fine chemical for the synthesis of ɛ-caprolactam, the precursor for Nylon-6. Nylon 6 (polyamide 6) is an important construction material for many industries including automotive, aircraft, electronic, clothing, and medicine industry. It is being produced in metric tons worldwide. The primary synthetic route is the condensation of cyclohexanone and hydroxylamine. The product is highly crystalline and precipitates from the reaction mixture. It is problematic for heterogeneous catalysts and scale-up. Additionally, cyclohexanone is produced from cyclohexane via harsh reaction conditions with low yield, making the process expensive. A direct photochemical synthesis from cyclohexane has been known for decades, but the use of UV or near-UV light and low yields with decomposition and blackening of the reaction mixture hinders its industrial use. We developed a photocatalyzed lab-scale process from cyclohexane under visible light that leads to high yields with no darkening of the reaction mixture. This mild process generates an intermediate that is not crystalline and, therefore, suitable for scale-up via flow synthesis. The intermediate to product cyclohexanone oxime was produced under a slightly basic medium.

Technology Readiness Level (If not a new project but an advancement of existing know how)

New Project

Outomes or Deliverables

Establish a continuous flow synthesis process for the synthesis of cyclohexanone oxime starting from cyclohexane solvent.

Project aligned with which most relevant UN SDGs Goal 11 - Sustainable Cities & Communities
Duration (In years) 3 years
Expected Impact

The established industrial process for cyclohexanone oxime starts with cyclohexanone. Cyclohexanone is synthesized form cyclohexane via chemical oxidation process that generates toxic waste, and the yield of the product cyclohexanone is <50%. Synthesis of cyclohexanone oxime directly from cyclohexane would make the whole process greener and sustainable with higher efficiency.

Implementation model (self- implemented/ outsourced partnership)

self- implemented

Total Budget (Recurring +Non-Recurring Expenses) 75 lakhs
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