Muconic Acid, Butadiene Dicarboxylic Acid, Hexadienedioic Acid, 505-70-4

MUCONIC ACID (CAS: 505-70-4) 

CAS Number: 505-70-4
EC Number (EINECS): 208-017-7
Molecular Formula: C₆H₆O₄
Molecular Weight: 142.11 g/mol
Chemical Class: Dicarboxylic acid (unsaturated)

SECTION 1: PRODUCT IDENTIFICATION AND CHEMICAL IDENTITY

SECTION 2: PHYSICAL AND CHEMICAL PROPERTIES

Muconic acid exists in three different stereoisomeric forms: cis,cis-, cis,trans-, and trans,trans-. The following table compares the key physical properties of these three isomers:

2.1. General Physical Properties

SECTION 3: ISOMERS AND IDENTIFICATION

Muconic acid exists in three stereoisomeric forms based on the geometry of the double bonds. These isomers have significantly different physical and chemical properties.

3.1. cis,cis-Muconic Acid (ccMA)

• Definition: Isomer with both double bonds in cis configuration

• CAS Number: 505-70-4

• Melting Point: 194-195°C

• Source: Primary product of biological fermentation

• Use: Precursor for adipic acid production; critical monomer for nylon-6,6 production

3.2. cis,trans-Muconic Acid (ctMA)

• Definition: Isomer with one double bond in cis and one in trans configuration

• Melting Point: 190-191°C

• Water Solubility: 5.2 g/L (5× higher than ccMA)

• Source: Spontaneous isomerization of ccMA under acidic conditions

3.3. trans,trans-Muconic Acid (ttMA)

• Definition: Isomer with both double bonds in trans configuration; thermodynamically most stable isomer

• CAS Number: 3588-17-8

• Melting Point: 301°C

• Water Solubility: < 0.1 g/L (very low)

• Special Property: Only isomer that undergoes Diels-Alder cycloaddition reactions

• Use: Bio-based terephthalic acid (for PET) and adipic acid production

SECTION 4: CHEMICAL PROPERTIES AND REACTIONS

4.1. Key Chemical Transformations

SECTION 5: MAJOR APPLICATIONS AND END-USES

5.1. Polymer and Plastic Production (Most Important Application)

5.2. Bio-based Chemicals

5.3. Biochemistry and Metabolomics

5.4. Other Applications

SECTION 6: INDUSTRY SUITABILITY MATRIX

SECTION 7: OTHER NAMES AND IDENTIFIERS

SECTION 8: PRODUCTION METHODS

8.1. Biotechnological Production (Preferred Method)

8.2. Chemical Synthesis

SECTION 9: TOXICOLOGY AND HEALTH EFFECTS

SECTION 10: ECOTOXICOLOGY AND ENVIRONMENTAL BEHAVIOR

SECTION 11: SAFETY AND STORAGE

SECTION 12: TRANSPORT INFORMATION

SECTION 13: FIRE-FIGHTING MEASURES

SECTION 14: ACCIDENTAL RELEASE AND CLEANUP

SECTION 15: FIRST AID MEASURES

SECTION 16: REGULATORY INFORMATION

SECTION 17: SUMMARY AND CRITICAL WARNINGS

Product Summary

CRITICAL WARNINGS

1. Sustainable Polymer Platform: Muconic acid is a "bio-privileged" molecule that can be produced from renewable sources (lignocellulosic biomass), enabling bio-based production of important polymers such as nylon-6,6, PET, and polyurethane.

2. Green Route to Nylon-6,6 and PET: Muconic acid can be hydrogenated to adipic acid (100% selectivity) for nylon-6,6 monomer or converted via Diels-Alder reaction to terephthalic acid for PET monomer. These routes provide up to 80% reduction in greenhouse gas emissions compared to conventional petrochemical production.

3. Isomer Selection is Critical: The three isomers of muconic acid (cis,cis-, cis,trans-, trans,trans-) have significantly different physical properties and reactivity profiles. For example, Diels-Alder reactions are effectively carried out only with the trans,trans-isomer. Isomer purity is critical for product selection and process design.

4. Advances in Bio-production: cis,cis-Muconic acid can be produced at 88.2 g/L titer from glucose using Corynebacterium glutamicum, demonstrating the industrial viability of biological production.

5. Alternative to Conventional Adipic Acid: Muconic acid route eliminates N₂O emissions compared to conventional cyclohexane/nitric acid oxidation process for adipic acid production.

6. Storage: Store in cool, dry, well-ventilated areas. Keep away from strong oxidizers.

7. Benzene Exposure Biomarker: trans,trans-Muconic acid is used as a urinary biomarker for benzene exposure in humans.

8. Solubility Challenges: Low water solubility of cis,cis- and trans,trans-isomers (<0.2 g/L) causes isolation and purification challenges. The 5× higher solubility of cis,trans-isomer may affect processing efficiency.

9. Catalytic Transformations: Single-atom Ru-zeolite catalyst enables highly selective (95%) isomerization of ccMA to ttMA, enabling PET production via Diels-Alder route.

10. Future Perspective: Muconic acid is recognized as a critical platform chemical for the bio-based economy, with ongoing research focused on sustainable polymer production.

IMPORTANT DISCLAIMER: This Technical Data Sheet (TDS) is for informational purposes only and is based on available technical data. The user is solely responsible for determining the product's suitability for their specific application and for complying with all applicable local, national, and international regulations. For complete safety, storage, handling, transportation, disposal, and regulatory compliance information, always refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. Users are responsible for testing the product in their own processes and applications. All local, national, and international regulations must be followed when working with Muconic Acid.