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ADIPIC ACID POLYESTER

Adipic acid polyester possesses strong acidic properties and can be effectively used in acid-base reactions.
Adipic acid polyester is a non-natural dicarboxylic acid with a chemical formula of C6H10O4. 
Adipic acid polyester is synthetically produced commercially and is widely used in many industries, particularly in the production of nylon 6,6 polymer, constituting up to 90% of its composition.

CAS Number: 52089-65-3
Molecular Formula: C6H2D8O4
Molecular Weight: 154.19

Synonyms: Hexanedioic acid, polymer with 1,3-butanediol, hexadecanoate, 1,3-Butylene glycol, adipic acid polyester, terminated with palmitic acid 1,3Butylene glycol, adipic acid polyester, terminated with palmitic acid, ADMEX 330, Adipic acid, 1,3-butylene glycol, palmitic acid polymer, Adipic acid, 1,3butylene glycol, palmitic acid polymer, Adipic acid, palmitate, 1,3-butanediol polymer, Adipic acid, palmitate, 1,3butanediol polymer, DTXSID1097783, 68332-62-7HEXANEDIOIC-D8 ACID;HEXANE-DB-1,6-DIOIC ACID;ADIPIC-DB ACID;Hexanedioic Acid-D8;adipic acid-d8

Adipic acid polyester is most commonly synthesized from a polycondensation reaction between ethylene glycol and adipic acid.
Adipic acid polyesterhas been studied as it is biodegradable through a variety of mechanisms and also fairly inexpensive compared to other polymers.
Its lower molecular weight compared to many polymers aids in its biodegradability.

Adipic acid polyester or PEA is an aliphatic polyester.
Adipic acid polyester is a type of polymer made by the reaction of adipic acid with alcohols (such as diols), which leads to the formation of long-chain molecules known as polyesters. 
The polymerization process involves the condensation of adipic acid, a dicarboxylic acid, with alcohols that contain two hydroxyl groups, resulting in the formation of ester linkages. 

These polyester polymers are widely recognized for their high strength, durability, and resistance to wear and tear. 
The resulting material is commonly used in plastics, fibers, and resins for a variety of applications.
Adipic acid polyester can be synthesized through a variety of methods. 

First, it could be formed from the polycondensation of dimethyl adipate and ethylene glycol mixed in equal amounts and subjected to increasing temperatures (100 °C, then 150 °C, and finally 180 °C) under nitrogen atmosphere. 
Methanol is released as a byproduct of this polycondensation reaction and must be distilled off.
econd, a melt condensation of ethylene glycol and adipic acid could be carried out at 190-200 °C under nitrogen atmosphere.

Lastly, a two-step reaction between adipic acid and ethylene glycol can be carried out. 
A polyesterification reaction is carried out first followed by polycondensation in the presence of a catalyst. 
Both of these steps are carried out at 190 °C or above.

Many different catalysts can be used such as stannous chloride and tetraisopropyl orthotitanate. 
Generally, the PEA is then dissolved in a small amount of chloroform followed by precipitation out in methanol.[8][9]
Adipic acid polyester is an organic acid containing six carbon atoms and two carboxylic acid groups. 

Adipic acid polyester has a crystalline structure in solid state at room temperature.
The basic chemical structure of Adipic acid polyester is derived from hexanedioic acid, which features two carboxyl groups (-COOH) on opposite ends of a six-carbon chain. 
When this acid reacts with a diol (a compound with two alcohol groups, -OH), such as ethylene glycol or butanediol, the carboxyl groups of the adipic acid react with the alcohol groups to form ester bonds (C-O-C), releasing water molecules in the process. 

The polyester formed through this reaction is known for being versatile and can be modified in various ways to create materials with specific properties, such as varying degrees of rigidity, flexibility, or chemical resistance.
Adipic acid polyester is particularly notable for its use in the production of nylon-6,6 and nylon-6 fibers, which are integral to the textile industry, especially for clothing, carpets, and automotive fabrics. 

Additionally, Adipic acid polyester-based polyesters are used to create polyurethane resins for coatings, adhesives, and sealants due to their excellent adhesion properties and chemical stability. 
These polyesters can also be found in engineering plastics used in automotive, electronics, and construction industries, where high-performance materials are necessary.
Adipic acid polyester is soluble in water, making it suitable for applications in water-based systems.

Adipic acid polyester is an organic compound with the formula (CH2)4(COOH)2. 
From the industrial perspective, it is the most important dicarboxylic acid: About 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon. Adipic acid otherwise rarely occurs in nature.
Adipic acid polyester is a straight-chain dicarboxylic acid that exists as a white crystalline compound at standard temperature and pressure. 

Adipic acid polyester is one of the most important industrial chemicals and typically ranks in the top 10 in terms of volume used annually by the chemical industry.
Adipic acid polyester serves multiple purposes across various industries, from polyurethane production to food additives. 
Adipic acid polyester is non-harmful to human health and possesses low toxicity. 

Despite being synthetically produced, it is biodegradable and environmentally friendly.
Its solubility in water allows for use in water-based systems, as well as solubility in various solvents.

Adipic acid polyester is a versatile chemical compound widely used in industries, offering many advantages across different fields. 
However, ensuring appropriate formulations and safe usage practices is crucial for each intended application.

Melting point: 146-148oC
storage temp.: Refrigerator
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
color: White to Off-White

In terms of physical properties, Adipic acid polyester materials typically have good thermal stability, moderate flexibility, and are resistant to moisture and chemicals. 
This makes them suitable for use in durable goods, packaging, and medical devices. 
However, while they offer excellent mechanical properties, they can be sensitive to high temperatures, leading to thermal degradation in some cases.

Adipic acid polyesters are also part of the larger group of polyesters that include other biodegradable variants, as the adipic acid used in the polymerization process can come from renewable sources, making it a more eco-friendly option in some industrial applications. 
However, there are concerns about the environmental impact of polyester waste, as these materials can take a long time to decompose and may contribute to plastic pollution if not properly recycled.

Thus, while adipic acid polyester has a broad range of useful applications across many industries, it is important to consider both its performance and the environmental impact of its disposal.
Adipic acid polyester has been shown to be able to form both ring-banded and Maltese-cross (or ring-less) type spherulites. 
Ring-banded spherulites most notably form when crystallization is carried out between 27 °C and 34 °C whereas Maltese-cross spherulites form outside of those temperatures.

Regardless of the manner of banding, PEA polymer chains pack into a monoclinic crystal structure (some polymers may pack into multiple crystal structures but PEA does not).
The length of the crystal edges are given as follows: a = 0.547 nm, b = 0.724 nm, and c = 1.55 nm. 
The monoclinic angle, α, is equal to 113.5°.

The bands formed by PEA have been said to resemble corrugation, much like a butterfly wing or Pollia fruit skin.
An alternate and less frequently used method of synthesizing PEA is ring-opening polymerization. 
Cyclic oligo(ethylene adipate) can be mixed with di-n-butyltin in chloroform. 

This requires temperatures similar to melt condensation.
Conductivity of films made of PEA mixed with salts was found to exceed that of PEO4.5LiCF3SO3 and of poly(ethylene succinate)/LiBF4 suggesting it could be a practical candidate for use in lithium-ion batteries.
Notably, Adipic acid polyester is used as a plasticizer and therefore amorphous flows occur at fairly low temperatures rendering it less plausible for use in electrical applications. 

Blends of Adipic acid polyester with polymers such as poly(vinyl acetate) showed improved mechanical properties at elevated temperatures.
Adipic acid polyester is miscible with a number of polymers including: poly(L-lactide) (PLLA), poly(butylene adipate) (PBA), poly(ethylene oxide), tannic acid (TA), and poly(butylene succinate) (PBS).
Adipic acid polyester is not miscible with low density polyethylene (LDPE).

Miscibility is determined by the presence of only a single glass transition temperature being present in a polymer mixture.
Adipic acid polyester has a density of 1.183 g/mL at 25 °C and it is soluble in benzene and tetrahydrofuran.
Adipic acid polyester has a glass transition temperature of -50 °C.

Adipic acid polyester can come in a high molecular weight or low molecular weight variety, i.e.10,000 or 1,000 Da.
Further properties can be broken down into the following categories.

In general, most aliphatic polyesters have poor mechanical properties and Adipic acid polyester is no exception. 
Little research has been done on the mechanical properties of pure Adipic acid polyester but one study found PEA to have a tensile modulus of 312.8 MPa, a tensile strength of 13.2 MPa, and an elongation at break of 362.1%.
Alternate values that have been found are a tensile strength of ~10 MPa and a tensile modulus of ~240 MPa.

IR spectra for Adipic acid polyester show two peaks at 1715–1750 cm−1, another at 1175–1250 cm−1, and a last notable peak at 2950 cm−1. 
These peaks can be easily determined to be from ester groups, COOC bonds, and CH bonds respectively.
Aliphatic copolyesters are well known for their biodegradability by lipases and esterases as well as some strains of bacteria. 

Adipic acid polyester in particular is well degraded by hog liver esterase, Rh. delemar, Rh. arrhizus, P. cepacia, R. oryzae, and Aspergillus sp.
An important property in the speed of degradation is the crystallinity of the polymer. 
Neat Adipic acid polyester has been shown to have a slightly lower degradation rate than copolymers due to a loss in crystallinity.

Adipic acid polyester copolymers at high PEA concentrations were shown to degrade within 30 days while neat PEA had not fully degraded, however, mixtures approaching 50/50 mol% hardly degrade at all in the presence of lipases.
Copolymerizing styrene glycol with adipic acid and ethylene glycol can result in phenyl side chains being added to Adipic acid polyester. 
Adding phenyl side chains increases steric hindrance causing a decrease in the crystallinity in the PEA resulting in an increase in biodegradability but also a notable loss in mechanical properties.

Further work has shown that decreasing crystallinity is more important to degradation carried out in water than whether or not a polymer is hydrophobic or hydrophilic. 
Adipic acid polyester polymerized with 1,2-butanediol or 1,2-decanediol had an increased biodegradability rate over PBS copolymerized with the same side branches. 
Again, this was attributed to a greater loss in crystallinity as PEA was more affected by steric hindrance, even though it is more hydrophobic than PBS.

Adipic acid polyester urethane combined with small amounts of ligin can aid in preventing degradation by acting as an antioxidant. 
Additionally, the mechanical properties of the PEA urethane increased by ligin addition. 
This is thought to be due to the rigid nature of ligin which aids in reinforcing soft polymers such as PEA urethane.

When Adipic acid polyester degrades, it has been shown that cyclic oligomers are the highest fraction of formed byproducts.
Using toluene as a solvent, the efficacy of degrading PEA through ultrasonic sound waves was examined. 
Degradation of a polymer chain occurs due to cavitation of the liquid leading to scission of chemical chains. 

In the case of Adipic acid polyester, degradation was not observed due to ultrasonic sound waves. 
This was determined to be likely due to PEA not having a high enough molar mass to warrant degradation via these means.
A low molecular weight has been indicated as being necessary for the biodegradation of polymers.

Uses:
Adipic acid polyester is used in a variety of industries due to its versatile properties, making it a highly valuable material in the manufacturing of numerous products. 
One of the primary uses of adipic acid polyester is in the production of nylon fibers, particularly nylon-6,6 and nylon-6, which are integral in the textile industry. 
These fibers are widely used in the creation of clothing, carpets, upholstery, and automotive fabrics because they offer excellent durability, strength, and resilience.

The ability of these fibers to withstand wear and tear makes them ideal for high-stress applications, such as in the production of reinforced fabrics and high-performance textiles.
In addition to textiles, Adipic acid polyester is used in the manufacture of engineering plastics, where it plays a crucial role in industries like automotive manufacturing, electronics, and construction. 
These polyesters are often chosen for their mechanical strength, chemical resistance, and thermal stability, making them suitable for parts that need to endure extreme temperatures, chemical exposure, and heavy loads. 

In the automotive sector, for example, adipic acid polyesters are employed in the creation of engine components, electrical connectors, and interior trims, offering enhanced performance and longevity compared to other materials.
Adipic acid polyester is also used to produce polyurethane resins, which are utilized in a wide range of applications such as coatings, adhesives, sealants, and foams. 
These resins are particularly valued for their excellent adhesion properties and resilience in challenging environments. 

In construction and industrial applications, polyurethane-based materials made from adipic acid polyester are used for protective coatings on surfaces exposed to heavy traffic or environmental stress, providing long-lasting protection against abrasion, moisture, and chemical degradation.
Adipic acid polyester is a useful isotopically labeled research compound.
Adipic acid polyester is highly valued for its flexibility, strength, chemical resistance, and thermal stability, making it indispensable in a range of industries, from automotive and electronics to textiles, medical devices, and packaging.

Adipic acid polyester can effectively be used as a plasticizer reducing the brittleness of other polymers. 
Adding PEA to PLLA was shown to reduce the brittleness of PLLA significantly more than poly(butylene adipate) (PBA), poly(hexamethylene adipate) (PHA), and poly(diethylene adipate) (PDEA) but reduced the mechanical strength.
The elongation at break was increased approximately 65x over neat PLLA.

The thermal stability of PLLA also showed a significant increase with an increasing concentration of PEA.
Adipic acid polyester has also been shown to increase the plasticity and flexibility of the terpolymer maleic anhydride-styrene-methyl metacrylate (MAStMMA). 
Observing the changes in thermal expansion coefficient allowed for the increasing in plasticity to be determined for this copolymer blend.

Adipic acid polyesters is an effective method of healing microcracks caused by an accumulation of stress. 
Diels-Alder (DA) bonds can be incorporated into a polymer allowing microcracks to occur preferentially along these weaker bonds. 
Furyl-telechelic poly(ethylene adipate) (PEAF2) and tris-maleimide (M3) can be combined through a DA reaction in order to bring about self-healing capabilities in PEAF2. 

Adipic acid polyester was found to have some healing capabilities after 5 days at 60 °C, although significant evidence of the original cut appeared and the original mechanical properties were not fully restored.
Adipic acid polyester microbeads intended for drug delivery can be made through water/oil/water double emulsion methods. 
By blending PEA with Poly-ε-caprolactone, beads can be given membrane porosity. 

Microbeads were placed into a variety of solutions including a synthetic stomach acid, pancreatin, Hank's buffer, and newborn calf serum.
The degradation of the microcapsules and therefore the release of the drug was the greatest in newborn calf serum, followed by pancreatin, then synthetic stomach acid, and lastly Hank's buffer. 
The enhanced degradation in newborn calf serum and pancreatin was attributed to the presence of enzyme activity and that simple ester hydrolysis was able to be carried out. 

Additionally, an increase in pH is correlated with higher degradation rates.
Adipic acid polyester is used in the production of polyurethane foams and elastomers. 
This application is common in insulation materials, shoe soles, furniture fillings, and various other products.

Adipic acid polyester serves as a plasticizer in the production of certain plastics. 
It improves the properties of polyester resins and polyamide (nylon) plastics.
Adipic acid polyester can be used as a food additive in the food and beverage industry to regulate acidity and in products such as acid-tasting sweeteners.

Adipic acid polyester can be used in the production of some resins used in paints and coatings, enhancing the chemical resistance of the products.
Adipic acid polyester is utilized as an intermediate in the production of certain pharmaceutical compounds.
Adipic acid polyester plays a role in polyester-based films and plastic products, where its chemical stability and resistance to moisture make it a suitable material for packaging and protective films. 

These films are often used in food packaging, pharmaceutical products, and electronics, offering barrier properties that help preserve the integrity and quality of sensitive products. 
In the medical industry, adipic acid polyesters can be found in medical devices and drug delivery systems, where the material’s biocompatibility and strength ensure the safety and effectiveness of medical applications.

In addition to these established uses, Adipic acid polyester is also gaining attention as a sustainable material in certain bio-based applications. 
The renewable sources of adipic acid derived from biomass are encouraging the development of more eco-friendly products such as biodegradable plastics and green chemistry solutions. 
These efforts are aimed at reducing the environmental impact of traditional petroleum-based materials while maintaining the functional benefits of adipic acid polyester.

Safety Profile:
Adipic acid polyester, like many synthetic materials, presents several potential hazards, particularly during manufacturing, handling, and disposal processes. 
One of the primary concerns associated with adipic acid polyester is its flammability. 
The polymeric nature of the material means that when exposed to high heat or flames, it can catch fire and release potentially harmful fumes or toxic gases. 

These gases may include carbon monoxide, carbon dioxide, and other volatile organic compounds (VOCs), which can pose significant risks to human health if inhaled in large quantities.
Another hazard associated with adipic acid polyester is its potential to cause respiratory irritation. 
When the polyester material is processed, particularly during heating or melting processes, it can release dust or particulate matter into the air. 

Inhalation of these particles, especially in an industrial setting where they might be more concentrated, can lead to lung irritation, asthma-like symptoms, or other respiratory problems, particularly in individuals who are sensitive to such irritants. 
This risk can be mitigated with the use of proper ventilation systems and protective equipment like respirators in workplaces where adipic acid polyester is processed or handled.

The chemical composition of adipic acid polyester means that it may also pose certain environmental hazards if improperly disposed of. 
As a plastic material, it is not biodegradable under normal environmental conditions, which raises concerns about plastic pollution. 
When discarded improperly, adipic acid polyester can contribute to the growing issue of plastic waste in oceans, landfills, and other natural environments, where it may persist for years, affecting wildlife and ecosystems. 

Furthermore, the polymer’s non-biodegradability means that it could potentially accumulate in the environment, posing a long-term hazard to plant and animal life.
There is also a concern regarding the toxicity of certain chemicals involved in the production or breakdown of adipic acid polyester. 
Some of the precursors or additives used in the polymerization process may have toxicological properties that can pose risks during manufacturing or if the material is degraded or burned. 

For example, adipic acid itself can irritate the skin and eyes and can cause respiratory issues when inhaled as dust. 
The solvents used in the production or processing of adipic acid polyester could also contribute to health hazards, such as dermal irritation, nervous system effects, or liver toxicity if proper handling procedures are not followed.


 

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