26472-26-4

Upstream product

• 1165952-92-0 cyclohexa-1,4-diene 
• 1119-72-8 cis,cis-Muconic acid 

Downstream Products

• 129159-01-9 cis-3-hexenedioic acid monobenzyl ester 
• 129838-67-1 (cis-5-benzyloxycarbonyl-3-pentenoyl)-(S-benzyl-L-cysteinyl)-(D-valine) benzyl ester 

Relevant academic research and scientific papers

Electrochemical hydrogenation of bioprivileged: Cis, cis -muconic acid to trans -3-hexenedioic acid: From lab synthesis to bench-scale production and beyond

The integration of microbial and electrochemical conversions in hybrid processes broadens the portfolio of products accessible from biomass. For instance, sugars and lignin monomers can be biologically converted to cis,cis-muconic acid (ccMA), a bioprivileged intermediate, and further electrochemically upgraded to trans-3-hexenedioic acid (t3HDA). This novel monounsaturated monomer is gaining increasing attention as it can substitute adipic acid in Nylon 6,6 to introduce desired properties and yield polyamides with performance advantages. The implementation of t3HDA for advanced polymer production is, however, hampered by the low productivities achieved to date, in the order of milligrams per hour per cm2. Here, we report on new synergies between microbial and electrochemical conversions and present a simple strategy to enhance the productivity of t3HDA by over 50 times. Specifically, we show that the broth composition has a dramatic role on the subsequent electrochemical step. Broth with neutral pH and high ccMA titer obtained from bacteria was found to enhance the electrochemical hydrogenation while impeding the parasitic hydrogen evolution reaction. As a result, high productivities were achieved under industrially-relevant current densities (200-400 mA cm-2). The effect of other parameters that are key for scale up and continuous operation, namely reactor configuration, potentiostatic/galvanostatic operation mode, and cathode material are also discussed. The experimental results served as input parameters for a detailed technoeconomic analysis and the blueprint of a hybrid microbial electrosynthesis process for t3HDA production.

Single particle analysis of secondary organic aerosols formed from 1,4-cyclohexadiene ozonolysis using a laser-ionization single-particle aerosol mass spectrometer

Real-time analysis of secondary organic aerosol (SOA) particles formed from 1,4-cyclohexadiene (CHD) ozonolysis in a smog chamber was performed using a laser-ionization single-particle aerosol mass spectrometer (LISPA-MS). The instrument can be used to obtain both the size and chemical compositions of individual aerosol particles with a high time-resolution (≈2 s at the maximum). Both positive- and negative-ion mass spectra can be obtained by changing the voltage polarity of the instrument. The negative-ion spectra of the SOA particles provided important information about the chemical compositions of the SOA particles. In the negative-ion spectra, intense mass peaks were determined to correspond to ions with carboxyl and aldehyde groups. The signal intensities of the intense mass peaks from compounds with carboxyl groups were higher than those from compounds with aldehyde groups as a function of the particle size. The peaks suggest that the SOA particles contain more oxygenated organic compounds as the particle size increases, namely, the chemical compositions of the SOA particles vary as a function of the particle size. We demonstrated that the real-time single-particle analysis of SOA particles by using the LISPA-MS technique can be used to clarify the formation and transformation processes of SOA particles in smog chambers.