Dimethyl 2,6-Naphthalenedicarboxylate: Uses, Properties & FAQs
Dimethyl 2,6-Naphthalenedicarboxylate: Uses, Properties & FAQs
Dimethyl 2,6-Naphthalenedicarboxylate is a high-purity aromatic diester monomer widely used as a key building block in the synthesis of high-performance polyester polymers, particularly polyethylene naphthalate (PEN).
- Chemical Name
- Dimethyl 2,6-Naphthalenedicarboxylate
- CAS Number
- 840-65-3
- Molecular Formula
- C14H12O4
- Molecular Weight
- 244.24 g/mol
- Primary Application
- Monomer for polyethylene naphthalate (PEN) and other high-performance polyesters
- Physical Form
- White to off-white crystalline solid
- Aladdin SKU
- D137061B
What Is Dimethyl 2,6-Naphthalenedicarboxylate?
Dimethyl 2,6-Naphthalenedicarboxylate (NDC; CAS 840-65-3) is the dimethyl ester of 2,6-naphthalenedicarboxylic acid. It is an aromatic dicarboxylate ester in which two methyl ester groups are positioned symmetrically at the 2- and 6-positions of the naphthalene ring system. This symmetric substitution pattern imparts excellent rigidity and planarity to polymer chains derived from this monomer.
The compound appears as a white to off-white crystalline solid at room temperature. Its fused bicyclic aromatic core differentiates it from simpler terephthalate-based monomers and is directly responsible for the superior thermal, mechanical, and barrier properties observed in polymers containing the naphthalene unit.
Key Applications in Research and Industry
Dimethyl 2,6-Naphthalenedicarboxylate serves as the principal monomer in the synthesis of polyethylene naphthalate (PEN), a high-performance engineering polyester. PEN exhibits significantly higher glass-transition temperature, tensile strength, and gas barrier performance compared to polyethylene terephthalate (PET), making it attractive for demanding packaging, film, and fiber applications.
In academic and industrial research, NDC is employed in:
- Homo- and co-polyester synthesis: Melt-phase or solution-phase transesterification with diols such as ethylene glycol produces PEN and related copolymers.
- Liquid crystal polymer (LCP) research: NDC-derived rigid-rod segments are incorporated into thermotropic LCP formulations.
- Structure–property studies: The compound is used as a model substrate to investigate transesterification kinetics, catalyst screening, and thermal characterization of naphthalate polyesters.
- Organic electronics and materials science: Naphthalene-based aromatic frameworks are explored as components in organic semiconductors and supramolecular assemblies.
Handling, Storage, and Safety Guidance
Dimethyl 2,6-Naphthalenedicarboxylate is generally considered to be of low acute toxicity at typical laboratory exposure levels; however, standard laboratory safety precautions should always be observed. Users should consult the current Safety Data Sheet (SDS) provided with the product before use.
Recommended handling practices:
- Use appropriate personal protective equipment (PPE): laboratory coat, chemical-resistant gloves, and safety glasses.
- Handle in a well-ventilated area or fume hood, particularly when working with heated melts or solutions.
- Avoid generating dust during weighing operations; use respiratory protection if dust generation is unavoidable.
Storage conditions:
- Store in a tightly sealed container at room temperature (15–25 °C), protected from moisture and direct light.
- Keep away from strong oxidizing agents and strong bases.
- When stored under appropriate conditions, the compound has good long-term stability.
Note: Always verify specific storage conditions and hazard classifications against the current product SDS, as regulatory classifications may vary by jurisdiction.
Ordering and Product Specifications
Aladdin Scientific supplies Dimethyl 2,6-Naphthalenedicarboxylate under SKU D137061B. Researchers should confirm current pack sizes, purity grades, and pricing through the Aladdin Scientific website or by contacting technical sales.
When evaluating this product for a specific application, consider the following specification parameters:
- Purity: Confirm the certificate of analysis (CoA) for purity by GC or HPLC, melting point, and water content as appropriate for your synthetic or analytical requirements.
- Pack size: Available pack sizes may range from small research quantities to larger amounts for scale-up studies; contact Aladdin for bulk inquiries.
- Documentation: CoA, SDS, and structural confirmation data (e.g., NMR, IR) may be available upon request.
For order placement, visit the Aladdin Scientific website, use the SKU D137061B search, or contact your regional Aladdin representative.
Frequently Asked Questions at a Glance
This section consolidates the most common technical and logistical questions received from researchers and procurement teams regarding Dimethyl 2,6-Naphthalenedicarboxylate (SKU D137061B). Detailed answers are provided in the FAQ section below.
Topics covered include solubility, reaction conditions for transesterification, differences from related monomers, purity considerations, and ordering logistics. If your question is not addressed here, please contact Aladdin Scientific technical support directly.
Frequently asked questions
What is Dimethyl 2,6-Naphthalenedicarboxylate used for?
Dimethyl 2,6-Naphthalenedicarboxylate is primarily used as a monomer in the synthesis of polyethylene naphthalate (PEN) and related high-performance copolyesters via transesterification with diols. It is also used in liquid crystal polymer research, organic materials science, and as a model substrate for catalyst and reaction kinetics studies in polyester chemistry.
How does Dimethyl 2,6-Naphthalenedicarboxylate differ from dimethyl terephthalate (DMT)?
Both are aromatic dimethyl dicarboxylate monomers used in polyester synthesis, but Dimethyl 2,6-Naphthalenedicarboxylate contains a fused bicyclic naphthalene ring rather than the single benzene ring of DMT. This results in greater chain stiffness and planarity in the derived polymer, leading to higher glass-transition temperature, improved tensile modulus, and superior gas barrier properties in PEN compared to PET made from DMT.
What solvents can dissolve Dimethyl 2,6-Naphthalenedicarboxylate?
Dimethyl 2,6-Naphthalenedicarboxylate has limited solubility in water and cold common organic solvents due to its crystalline aromatic structure. It is generally soluble in hot polar aprotic solvents such as dimethyl sulfoxide (DMSO) and N,N-dimethylformamide (DMF), and in chlorinated solvents such as chloroform at elevated temperatures. For polymerization applications, the monomer is typically used in melt-phase reactions without a separate solvent.
What are the recommended reaction conditions for transesterification with Dimethyl 2,6-Naphthalenedicarboxylate?
Transesterification of Dimethyl 2,6-Naphthalenedicarboxylate with diols is typically conducted in the melt phase at elevated temperatures (commonly above 200 °C) using metal-based catalysts such as titanium(IV) butoxide, antimony trioxide, or zinc acetate, with removal of the methanol by-product under reduced pressure. Specific temperatures, catalyst loadings, and reaction times depend on the target polymer and should be optimized experimentally. Users should consult primary literature on PEN synthesis for detailed protocols.
How should Dimethyl 2,6-Naphthalenedicarboxylate be stored to maintain quality?
Store Dimethyl 2,6-Naphthalenedicarboxylate in a tightly sealed container at room temperature (15–25 °C), away from moisture, heat, and direct light. Under these conditions the compound is expected to remain stable for an extended period. Always verify specific storage requirements on the product SDS and certificate of analysis supplied by Aladdin Scientific.
How do I place an order for Dimethyl 2,6-Naphthalenedicarboxylate from Aladdin Scientific?
You can order Dimethyl 2,6-Naphthalenedicarboxylate directly from the Aladdin Scientific website by searching for SKU D137061B, or by contacting your regional Aladdin sales representative. For bulk quantities or custom purity grades, please reach out to Aladdin technical sales for a quotation and availability confirmation.
References
- Aladdin Scientific product listing: Dimethyl 2,6-Naphthalenedicarboxylate, SKU D137061B.
- General reference: Textbook-level knowledge on polyethylene naphthalate (PEN) synthesis and properties via transesterification of NDC with ethylene glycol.
- Safety and handling information derived from general chemical safety principles; verify against current SDS for D137061B from Aladdin Scientific.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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