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Dioctyl adipate(DOA) is an organic compound with the molecular formula c22h42o4, CAS 123-79-5. It is yellowish or colorless oily liquid with slight odor, insoluble in water, soluble in organic solvents such as methanol, ethanol, ether, acetone, acetic acid, chloroform, ethyl acetate, gasoline, toluene, mineral oil, vegetable oil, etc. Slightly soluble in ethylene glycol. The relative density is 0.927, the refractive index (25 ℃) is 1.446, and the viscosity is 0.0135 PA · s. Acute oral toxicity test in mice showed no toxicity.
On october27,2017, the list of carcinogens published by the international agency for research on cancer of the World Health Organization was preliminarily sorted out for reference. Di (2-ethylhexyl) adipate was included in the list of Category 3 carcinogens. It can be used as plasticizer, cold resistant agricultural film, artificial leather plate, rubber softener and synthetic lubricant.
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CF |
C22H42O4 |
|
EM |
371 |
|
MW |
371 |
|
m/z |
370 (100.0%), 371 (23.8%), 372 (2.7%) |
|
EA |
C, 71.31; H, 11.42; O, 17.27 |
|
|
|
Dioctyl adipate is a common plasticizer widely used in medical devices. It has good plasticity and softness, making it an ideal choice for manufacturing medical devices. However, with increasing attention to the health risks of DEHP, some countries and regions have begun to restrict or prohibit its use.
1. Hoses: Widely used as plasticizers for medical device hoses. Hoses are an important component of many medical devices, such as intravenous infusion tubes, catheters, gastrointestinal drainage tubes, etc. DEHP can increase the flexibility and operability of hoses, making them easier to bend and insert, improving patient comfort and ease of use.
2. Infusion bags and tubes: also used as plasticizers for infusion bags and tubes. Infusion bags are commonly used infusion equipment in hospitals, and DEHP can make infusion bags have good flexibility and deformability, making them convenient for patients to carry and use.
The infusion tube is a channel for the flow of traditional Chinese medicine during the infusion process, and the addition of DEHP can increase the flexibility and durability of the tube.
3. Blood bag: A blood bag is a container for storing and transporting blood, often used as a plasticizer. DEHP can increase the flexibility, durability, and sealing of blood bags, ensuring the safety and stability of blood during storage and transportation.
4. Syringes and infusion sets: They are also widely used in the manufacturing of syringes and infusion sets. Syringes are one of the most commonly used medical devices by healthcare workers, and DEHP can improve the softness and operability of syringes, making them easier to use and control. Infusion sets are one of the important ways of drug delivery, and the addition of DEHP can improve the softness and durability of infusion sets, ensuring accurate delivery of medication.
Performance And Advantages:
Plasticity And Flexibility:
It has good plasticity and can make medical devices have good flexibility. This is very important for some medical devices that require bending and insertion, such as catheters, infusion tubes, etc.
Durability And Chemical Resistance:
It has high durability and chemical resistance, and can withstand multiple uses, cleaning, and disinfection processes. This makes medical devices made with dioctyl adipate more durable and reliable.
Transparency And Visibility:
With good transparency, medical workers can clearly observe the fluid or substance inside the device. This is very important for some medical devices that require monitoring and controlling fluids, such as infusion bags, infusion tubes, etc.
Cost Effectiveness:
Compared to other alternatives, the cost is relatively low, making it an economic choice for large-scale production of medical devices.
Related health and safety issues:
1. Potential endocrine disruptors:
Considered a potential endocrine disruptor that may have adverse effects on the human endocrine system. Some studies suggest that long-term exposure to DEHP may be associated with health issues such as reproductive developmental abnormalities, hormonal imbalances, and liver toxicity.
2. Releasability and pollution risk:It has a certain degree of releasability and can be released from medical devices and pollute the environment.
This may lead to patients or staff being exposed to DEHP, increasing their health risks.
3. Sensitivity to specific populations:
Specific populations such as children and pregnant women are more sensitive to the potential risk of DEHP. Children may have an impact on their reproductive and neurological development due to exposure to DEHP, and pregnant women may transmit DEHP to the fetus through the placenta.
Specific applications in medical products
Frozen medicine storage bag:
Material formula: PVC/DOA (100/40) blend, with 0.5% epoxy soybean oil added as an auxiliary stabilizer.
Performance: Impact strength>15 kJ/m ² at -40 ℃, ensuring the low-temperature storage safety of biological products such as plasma and vaccines.
Infusion set hose:
Multi layer co extrusion structure: inner layer (PVC/DOA)+middle layer (EVA oxygen barrier layer)+outer layer (PVC/DOA), DOA content gradient design enhances the flexibility and compression resistance of the hose.
Sterilization adaptability: It can withstand high temperature steam sterilization at 121 ℃ for 20 times, and DOA has better hydrolysis resistance (hydrolysis rate<0.5%/year) than citrate plasticizers.
Cardiac catheterization:
Material modification: Adding 5% nano silica to PVC/DOA substrate to improve the torque transmission efficiency (35% increase) and flexural resistance of the conduit.
Surface lubrication treatment: DOA is used as a carrier solvent to load polyethylene glycol (PEG) coating, reducing the friction coefficient between the catheter and the blood vessel wall (μ<0.02).
Artificial blood vessel:
Micro porous structure regulation: By plasticizing polyurethane (PU) materials with DOA, the porosity is controlled at 70-80% to meet the requirements of cell infiltration and nutrient permeation.
Dynamic compliance: The addition of DOA increases the vascular compliance index (CI) to 0.015-0.025, approaching the mechanical properties of natural blood vessels.
Blood collection tube additive:
Anticoagulant dispersion: DOA is used as a dispersant in heparin sodium/EDTA-K2 anticoagulant tubes to improve the uniform distribution of anticoagulants on the tube wall (coefficient of variation CV<5%).
Microbial culture dish:
Polystyrene (PS) modification: Adding 5% DOA increases the oxygen permeability of PS by 20% and promotes rapid growth of aerobic bacteria.
Innovative Applications in Drug Formulation Development
Preclinical research tools
Pharmacokinetic model:
Liposome simulation: DOA is used as a model membrane material to study the distribution behavior of drugs in lipid bilayers (distribution coefficient logP prediction error<0.3).
Nanotoxicity assessment:
Nanoparticle dispersion: DOA coated graphene oxide (GO) nanosheets exhibit a 60% increase in stability in physiological media, making them suitable for long-term toxicity studies.
Solid dispersion technology:
Solubilization of insoluble drugs: The carrier material prepared by compounding DOA with polyvinylpyrrolidone (PVP) can increase the solubility of curcumin by 12 times.
Preparation of sustained-release microspheres: DOA plasticized polylactic acid glycolic acid (PLGA) microspheres were used, and the drug release period was extended to 30 days (in vitro release test).
Transdermal drug delivery system (TTS):
Pressure sensitive adhesive modification: Adding DOA to acrylic pressure-sensitive adhesive reduces the modulus of the adhesive layer (from 800 kPa to 200 kPa) and improves the adhesion between the patch and the skin.
Drug storage design: DOA is used as a liquid storage material for loading lipophilic drugs (such as ketoprofen), with a drug loading capacity of 12-15%.
DOA is generally synthesized from adipic acid and ethyl hexanol isooctanol under acid catalysis. At present, there are many kinds of catalysts used to synthesize dioctyl adipate, which can be summarized into the following categories: inorganic acid catalysts, organic acid catalysts, titanate catalysts, solid acid catalysts. Among them, solid acid catalysts have the advantages of high catalytic activity, high selectivity, high temperature resistance, simple preparation, little pollution, simple post-treatment and so on. They are a kind of environment-friendly catalysts with wide application prospects, and have attracted much attention. Therefore, using solid acid catalysts instead of other types of catalysts to synthesize diacetyl adipate has become a development trend in modern industry.
Activity is a high specific surface active material developed in the late 1970s. As a catalyst carrier, it can not only help to disperse the active components, improve the role of the active phase, but also reduce the possibility of high-temperature sintering deactivation. The traditional activated carbon is a kind of spark treated porous carbon, which is in powder or granular form, while the activated carbon fiber is a fiber pile, and the fiber is covered with micropores. Its adsorption capacity for organic gases is several to dozens of times higher than that of granular activated carbon in air, 5 to 6 times higher in aqueous solution, and the adsorption rate is 100 to 1000 times faster.
Heteropoly acid is a multi-component proton acid with uniform strength. It has high catalytic activity and selectivity for many reactions, and has the advantages of non-volatile, good thermal stability and fast regeneration. It is an ideal catalyst. It has been reported that heteropoly acid and its supported catalyst were used to catalyze the reaction of adipic acid and n-octanol to synthesize DOA. The optimum reaction condition was that the molar ratio of acid to alcohol was 1 ∶ 2 4. The amount of catalyst is 1. 5% of the mass of adipic acid 4%, reaction time 3 5h, the esterification rate can reach 99 1%. It was also reported that di-n-octyl adipate was synthesized from adipic acid and n-octanol, using environment-friendly phosphotungstic heteropoly acid as catalyst and toluene as water carrying agent. The optimum process conditions were as follows: the molar ratio of alcohol to acid was 2.8 ∶ 1, the amount of catalyst was 1.2% of acid mass, the amount of water carrying agent was 75% of acid mass, the reaction time was 3h, and the esterification rate was 99.23%.
The concept of molecular sieve was put forward in 1932. It is a kind of silicoaluminate microporous crystal. With the in-depth study of molecular sieves, they have been widely used and occupy an important position. For example, petroleum processing, petrochemical industry, fine chemical industry and daily chemical industry. Taking advantage of the high adsorption capacity and strong thermal stability of molecular sieves, Dioctyl Adipate was synthesized from adipic acid and 2 - ethylhexanol with HY Molecular Sieves as catalyst. The optimum reaction conditions were as follows: reaction temperature 160 ℃, adipic acid 0 03mol, acid alcohol molar ratio 1 ∶ 3, catalyst dosage 1 0 g, reaction time 5h, the highest esterification rate was 98.7%.
FAQ
What is DOA used for?
The most commonly used adipate plasticizer is dioctyl adipate (Figure 8.4). Adipates are generally used along with phthalate plasticizers to improve cold resistance to plastics-cold resistant plastic sheeting, cable, electric wires, paints, varnishes, faux leather, and outdoor, exposed water pipes.
Is DOA toxic?
Dioctyl Adipate, the diester of octyl alcohol and adipic acid, and Diisopropyl Adipate, the diester of isopropyl alcohol, are used in cosmetics as emollients and bases. These two ingredients have a low acute oral and percutaneous toxicity.
What chemical is doa?
Dioctyl adipate (DOA) is an organic compound with the formula (CH2CH2CO2C8H17)2. It is a colorless oily liquid . As well as related diesters derived from 2-ethylhexanol, decanol, isodecanol, etc., it is used as a plasticizer.
How is DOA made?
Process description: The esterification of adipic acid and 2-ethylhexanol produces the main product dioctyl adipate. For this purpose, the process consumes caustic soda (50%), hydrochloric acid, activated carbon, 2-ethylhexanol, and adipic acid.
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