1,4-Cyclohexanedicarboxylic Acid CAS 1076-97-7

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1,4-cyclohexanedicarboxylic acid is a chemical substance with the molecular formula of C8H12O4. The cis-trans mixture is a white crystal, soluble in organic solvents such as ethanol, acetone and chloroform, with a solubility of about 10% and a solubility of 1% in water (20 ℃). Trans-1, 4-cyclohexanedicarboxylic acid is a white phosphorous columnar crystal with lower solubility in water than cis, and its melting point is more than 300 ℃. It is a white leaf crystal with considerable solubility in water. It is an important raw material for polyester production. It is esterified with terephthalic acid (PTA) with the characteristics of dicarboxylic acid and used to produce polyester fiber after polycondensation. This kind of fiber with the trade name of Kodel is developed by Eastman Company of the United States. It is a highly polymerized linear condensation polymer with low relative density, high melting point and good electrical properties. Especially suitable for electrical equipment. CHDA tool modified (PET) resin.

1. Resin for powder coating; Resin for coil coating;

2. In medicine, it is used to synthesize peptic ulcer drugs;

3. In terms of polyester resin, it can be used as a modified monomer to improve the yellowing of polyester resin and improve its flexibility (softness) without changing its hardness.

4. High solid polyester melamine baking enamel; Unsaturated polyester resin for gel coating.

5. Application in waterborne polyurethane resin: 1, 4-CHDA and AD (adipic acid) have good processability, low solution viscosity, PIA (phthalic acid) ranks next in dispersion stability: 1, 4-CHDA>PIA>AD 1, 4-CHDA can also make the resin achieve a good balance between hardness and flexibility 1, 4-CHDA can be used to improve the dispersion of acrylic resin, and also has good storage stability. In addition, the coordination of 1,4-CHDA and acrylic resin.

A preparation method of 1,4-cyclohexanedicarboxylic acid, comprising the following steps:

(1) The raw material of product dimethyl ester is mixed with sodium hydroxide and water, heated to 60-110 ℃, hydrolyzed for 4-12h, the reaction is over, and the solution is cooled to 20-30 ℃;

(2) After (1) cooling the solution, slowly add hydrochloric acid for acidolysis until the pH value of the solution is less than 3, filter and wash, and dry to obtain white powder it.

The advantages of this method are that it is synthesized from product dimethyl ester as raw material through hydrolysis with alkali solution and hydrochloric acid acidification. The product yield and purity are high, and the yield can be more than 90%, and the purity is more than 99%.

1,4-cyclohexanedicarboxylic acid is prepared by hydrogenation of terephthalic acid (pta). US patent us 6291706 uses pd/c catalyst, which is loaded in the autoclave basket. First, continuously stir the aqueous solution with 5% pta concentration at 200 ℃ and 4.5 mpa for 45 minutes, and then react with the catalyst for 3 hours. The conversion reaches 66.5%. The reaction solution after removing solvent water contains 98.5% product chda. Japanese patent jp 2002020346 uses pta/h2o as raw material in autoclave reactor, uses pd-ba/c catalyst, reacts at 170 ℃ and 5.0 mpa for 1 hour, and the yield of chda reaches 96.4%. Other patents also proposed to use ru with relatively low price as the active component, and ru/c of activated carbon carrier was used for the reaction, for example, the reaction was reported in us patents us3027398 and us4654064; However, ru/c catalyst has poor activity and selectivity for this reaction.

Polymer Industry

High-Performance Polyesters
CHDA is a key monomer in PCT, a polyester with superior heat resistance, dimensional stability, and hydrolytic stability compared to PET. Applications include:

Electrical Connectors: PCT's low moisture absorption and high dielectric strength make it ideal for electronic components.

Automotive Parts: Used in under-the-hood components due to its resistance to engine fluids and temperature extremes.

Copolymerization with other diols (e.g., ethylene glycol) or dicarboxylic acids (e.g., isophthalic acid) tailors properties for specific uses. For instance, PCTG (a glycol-modified PCT) combines clarity, toughness, and chemical resistance, used in food packaging and cosmetic containers.

Polyamides and Polyimides
CHDA-derived diamines or diesters contribute to the synthesis of polyamides and polyimides with enhanced thermal and mechanical properties. These materials find use in:

Aerospace: Lightweight, heat-resistant components for aircraft engines.

Electronics: Flexible printed circuit boards and high-temperature adhesives.

Coatings and Adhesives

CHDA-based resins improve the durability and weatherability of coatings, particularly in automotive and architectural applications. Its cross-linking ability enhances adhesion, chemical resistance, and UV stability in formulations for:

Automotive Paints: Protects against scratches, UV degradation, and corrosion.

Industrial Coatings: Used in pipelines, tanks, and marine structures exposed to harsh environments.

Specialty Chemicals

Powder Coatings
CHDA's thermal stability enables its use in powder coatings, which cure at high temperatures without emitting volatile organic compounds (VOCs). These coatings are favored in appliances, furniture, and architectural finishes.

Unsaturated Polyester Resins (UPRs)
CHDA-modified UPRs offer improved mechanical properties and chemical resistance, used in fiber-reinforced plastics (FRPs) for boats, wind turbine blades, and automotive parts.

Toxicity and Ecological Impact

CHDA is classified as a low-toxicity compound, with oral LD50 values in rats exceeding 5 g/kg. However, its limited biodegradability raises concerns about long-term environmental persistence. Studies indicate that CHDA may accumulate in sediment or soil, potentially affecting aquatic ecosystems.

Sustainability Initiatives

The industry is adopting green chemistry principles to reduce CHDA's carbon footprint:

Catalyst Optimization: Replacing noble metals with earth-abundant alternatives (e.g., iron, cobalt) to lower costs and environmental impact.

Solvent Recycling: Implementing closed-loop systems to minimize waste in purification steps.

Bio-Sourcing: Investing in microbial or enzymatic synthesis routes to use renewable feedstocks.

Regulatory Compliance

CHDA production and use adhere to regulations such as REACH (EU), TSCA (US), and GHS (Global Harmonized System). Occupational exposure limits (OELs) are set to protect workers from respiratory or dermal irritation, with recommended airborne concentrations below 0.5 mg/m³.

Advanced Material Development

The global market for CHDA and its derivatives is projected to grow at a CAGR of 4–5% through 2030, driven by demand for high-performance materials in automotive, electronics, and packaging sectors. Key players include:

Eastman Chemical: A leading producer of PCT and PCTG resins.

SK Chemicals: Specializing in bio-based polyesters and CHDA derivatives.

Toray Industries: Innovating in CHDA-based polyimides for aerospace applications.

Cost Drivers

Raw Material Prices: Fluctuations in p-xylene or methanol costs influence CHDA pricing.

Technological Advancements: Innovations in hydrogenation catalysts or purification techniques reduce production costs, enhancing competitiveness.

Emerging Opportunities

Electric Vehicles (EVs): CHDA-based polymers are evaluated for battery enclosures due to their flame retardancy and lightweight properties, potentially improving EV range and safety.

3D Printing: High-temperature CHDA resins enable additive manufacturing of durable parts for prototyping and end-use applications.

1,4-Cyclohexanedicarboxylic acid exemplifies the intersection of traditional chemistry and cutting-edge materials science. Its unique structural features enable the creation of advanced polymers that meet stringent performance requirements in diverse industries, from automotive to electronics. As research progresses, CHDA's role in circular economy models, biomedical innovations, and green technologies will likely expand, cementing its status as a versatile and indispensable compound.

Future challenges include scaling bio-based synthesis methods, optimizing recycling pathways, and addressing regulatory hurdles in global markets. However, with ongoing interdisciplinary collaboration, CHDA is poised to contribute significantly to the development of next-generation materials that balance functionality, sustainability, and economic viability.

By continuing to explore CHDA's chemical potential and industrial applications, scientists and engineers can unlock new solutions to global challenges, from climate change to healthcare, ensuring its relevance in the 21st century and beyond.

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