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Dibutyl sebacate (DBS, CAS number 109-43-3) is an organic compound synthesized by esterification of sebacic acid and butanol, with the chemical formula C18H34O4 and CAS number 109-43-3. Its appearance is a colorless and transparent liquid, slightly soluble in water, but soluble in organic solvents such as alcohols, ethers, chloroform, acetone, and benzene. With its unique physical and chemical properties, it has demonstrated extensive application value in various fields such as plastics, rubber, coatings, fragrances, and pharmaceuticals.
Its molecular structure contains two butyl ester groups and one sebacic acid ester group, and this long-chain fatty acid ester structure endows it with excellent flexibility and extensibility. As a plasticizer, its mechanism of action is to embed intermolecular forces into polymer chains, weaken intermolecular van der Waals forces, thereby reducing the glass transition temperature (Tg) of materials and enhancing their plasticity in low-temperature environments. For example, after adding DBS to polyvinyl chloride (PVC), the material's brittleness temperature can be reduced from -20 ℃ to -40 ℃, significantly expanding its low-temperature application range.

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C.F |
C18H34O4 |
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Exact Mass |
314 |
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M.W |
314 |
|
m/z |
314 (100.0%), 315 (19.5%), 316 (1.8%) |
|
E.A |
C, 68.75; H, 10.90; O, 20.35 |
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|
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Dibutyl Sebacate (DBS) is an organic compound synthesized by esterification of sebacic acid and butanol, with the chemical formula C ₁₈ H ∝₄ O ₄. Its colorless and transparent oily liquid form, with a fruity aroma and a light oily smell, is slightly soluble in water but easily soluble in organic solvents, making it uniquely valuable in the food industry.
1. The core role of cold resistant plasticizers
As a cold resistant plasticizer, it plays a crucial role in food packaging materials. The long-chain fatty acid ester groups in its molecular structure can be embedded into polymer chains (such as polyvinyl chloride PVC, polystyrene PS), weakening intermolecular van der Waals forces and thereby reducing the glass transition temperature (Tg) of the material. For example, after adding DBS to PVC, the brittleness temperature of the material can be reduced from -20 ℃ to -40 ℃, significantly expanding its application range in low-temperature environments. This is particularly important for food packaging that requires refrigeration or freezing, such as ice cream boxes and frozen food bags, as it can effectively prevent packaging materials from becoming brittle or cracking at low temperatures, ensuring the safety and integrity of food.
2. Food grade safety certification
DBS has been recognized by international authoritative institutions as a safe food grade plasticizer. Its GRAS (Generally Recognized as Safe) certification and FEMA (Flavor and Extract Manufacturers Association) code 2373 indicate that it is harmless to the human body at the prescribed dosage. Experimental data shows that the oral LD50 (median lethal dose) of rats is 16g/kg, which is much higher than the safety threshold of common food additives. In addition, DBS has extremely low migration in food packaging materials, meeting the relevant regulatory requirements of FDA (US Food and Drug Administration) and EU (European Union), and can be used with confidence for packaging that comes into direct contact with food.
3. Optimization of composite plasticizing system
Although DBS has excellent cold resistance, it has high volatility and is easily extracted by water, soap water, and detergent solutions. To overcome this drawback, DBS is often used in combination with phthalate plasticizers such as DBP and DOP. The composite plasticizing system can significantly improve the comprehensive performance of materials: DBS provides low-temperature flexibility, while phthalate plasticizers enhance the water resistance and durability of materials. For example, in PVC film, the composite use of DBS and DOP in a ratio of 3:7 can maintain the flexibility of the film at -30 ℃, while reducing the extraction rate in water to below 5%.
Food spices: Natural equivalent spices of fruit aroma type
1. Core ingredients of fruit essence
DBS has a unique fruity aroma and is widely used in the formulation of food spices. Its aroma characteristics are similar to those of fruits such as apples, pears, and bananas, and can be used as a natural equivalent spice. In soft drinks, the amount of DBS added is usually 1.0-5.0mg/kg, which can significantly enhance the fruit aroma and naturalness of the beverage. For example, adding 2.5mg/kg DBS to apple flavored carbonated beverages can increase the aroma score by 30% and significantly improve consumer acceptance.
2. Enhance the aroma of baked goods
DBS can be used as an aroma enhancer in baked goods such as cakes and cookies. Its high temperature resistance makes it less volatile during baking and can maintain the stability of food aroma for a long time.
Experiments have shown that adding 15mg/kg of DBS to cakes can maintain an aroma intensity of over 80% of the initial level after 7 days of storage, while cakes without DBS only maintain an aroma intensity of 50%. In addition, DBS can also be combined with fragrances such as vanillin and ethyl maltol to form more complex aroma profiles.
3. Blending of alcohol essence
DBS also plays an important role in the blending of alcohol essence. It can simulate the mature fruit aroma of brandy, rum and other alcoholic beverages, enhancing the quality and grade of the wine. For example, adding 5.6mg/kg DBS to brandy can make the fruity aroma of the wine more rich and the taste more rounded. At the same time, DBS can also be used as a solvent to help other flavor ingredients dissolve and disperse better and improve the stability and uniformity of essence.
Food additives: multifunctional and comprehensive applications
1. Seasoning agents and adjuvants
DBS can also be used as a flavoring agent or seasoning adjuvant in food. Its unique fruity aroma can enhance the taste and flavor of food, especially suitable for low-temperature foods such as ice cream and non-alcoholic beverages. In ice cream, the addition of DBS is usually controlled below 5ppm, which can significantly enhance the fruit aroma and smoothness of the ice cream. For example, adding 3ppm DBS to strawberry flavored ice cream can make the strawberry aroma of the ice cream more natural and long-lasting, and increase consumer satisfaction by 20%.
2. Plasticizers for oral preparations
In the pharmaceutical field, Dibutyl Sebacate can be used as a plasticizer for oral formulations. Its non-toxic and non irritating properties make it suitable for the preparation of tablet coatings, capsule shells, and other formulations. For example, in the coating of pediatric Ma Gan extract powder, DBS combined with coating materials such as Eudragit Elo and NE30D can significantly improve the flexibility and water resistance of the coating, preventing problems such as cracking and discoloration of the tablets during storage. Meanwhile, DBS has the same metabolic pathway as fat in oral formulations and does not have adverse effects on the human body.
3. Auxiliary components of transdermal drug delivery system
DBS can be used as plasticizer and solvent in transdermal drug delivery systems (such as patches and gel). It can improve the transdermal absorption rate of drugs, while enhancing the flexibility and adhesion of the drug delivery system. For example, in the transdermal delivery system of Headache Ning, DBS is combined with materials such as cellulose acetate and guar gum to form a stable pressure-sensitive adhesive solution, allowing the drug to be evenly distributed on the skin and improving treatment effectiveness. Experiments have shown that adding 2mg/cm ² DBS can increase the transdermal absorption rate of drugs by 15%, while significantly enhancing the flexibility of the drug delivery system.


preparation methods
The dosage of catalyst is 0.3%, the temperature is 130-140°C, the esterification is about 4-6 hours under normal pressure, and 0.1-0.3% activated carbon is added during esterification. The crude ester obtained is neutralized, dealcoholized and filtered to obtain the finished product. The raw material sebacic acid is prepared from castor oil. Raw material consumption (kg/t) sebacic acid 665 butanol 525
Refining method: vacuum distillation and refining.
In a 100mL three-necked flask equipped with a thermometer, reflux condenser and water separator, add a certain amount of sebacic acid, n-butanol and a small amount of catalyst, and use benzene as the water-carrying agent. After heating, dissolving and stirring, take a sample Determine its acid value. Heat and reflux to separate the water until almost no water comes out. After cooling slightly, take a sample to measure its acid value. After the reaction is completed, the reaction liquid is poured out. The catalyst is insoluble in the reaction liquid and remains in the reaction bottle for reuse. The reaction solution was washed with water, dilute Na2CO3 solution, and water respectively, and then dried with MgSO4. First, steam out the unreacted n-butanol and benzene under normal pressure, and then distill under reduced pressure to collect the fraction at 168~171℃/400Pa, which is the product. Copper sulfate is used as the esterification reaction catalyst. The reaction conditions are: 0.05 mol sebacic acid, the catalyst dosage is 3.0g, the amount ratio of alkyd substances is 4, the reaction time is 3.0h, the water-containing agent is 12mL, the ester of sebacic acid The conversion rate can reach 97.23%.
In a four-necked flask equipped with a water separator, a thermometer and a reflux condenser, add a certain amount of sebacic acid, n-butanol and ferric ammonium sulfate dodecahydrate. After heating, dissolving and stirring, take a sample to measure its acid value. Then heat and reflux to separate the water until almost no reflux water comes out. After cooling slightly, take a sample to measure its acid value. Use the GB1668-81 method to measure the change in acid value before and after the reaction, and calculate the esterification rate. After the reaction is completed, the reaction solution is neutralized to weak acidity, and then washed with water, 10% sodium carbonate aqueous solution, and water respectively; distilled, n-butanol is first evaporated under normal pressure, and then distilled under reduced pressure to collect the n-butanol at 172~175°C/400Pa. The fraction is the product.

Store in a cool, ventilated warehouse. Keep away from fire and heat sources. should be kept away from oxidizer, do not store together. Equipped with the appropriate variety and quantity of fire equipment. The storage area should be equipped with emergency release equipment and suitable containment materials.

Dibutyl sebacate is a versatile compound with a wide range of applications across various industries. Its unique properties make it a valuable addition to plastics, pharmaceuticals, cosmetics, food flavorings, and perfumes.
Applications
plastics
It is widely used as a plasticizer in the plastics industry. It effectively enhances the flexibility and cold resistance of plastics, making it a valuable additive in the production of various plastic products. As the plastics market continues to grow, the demand for DBS is also increasing.


pharmaceuticals
It is commonly employed as a film-forming agent and plasticizer in the pharmaceutical industry. DBS is used in the production of tablets, microspheres, granules, and microcapsule formulations. It helps to improve the dissolution and bioavailability of drugs, enhancing their therapeutic effect.
food flavorings
It is also used as a component in food flavorings. Its unique taste and aroma contribute to the overall flavor profile of various food products, making it a valuable addition to the food industry.


cosmetics
It finds applications in the cosmetic industry. It is used to adjust the viscosity and moisturizing properties of cosmetics, enhancing their performance and user experience. As the demand for cosmetics continues to rise, the use of DBS in this industry is also increasing.
perfumes
It is also employed in the production of perfumes and fragrances. DBS contributes to the creation of fruity and floral scents, adding depth and complexity to perfume formulations.


Chemical
It can also be used as a gas chromatographic fixed liquid and in organic synthesis.
When handling DBS, there are several important safety considerations and precautions that should be followed. Here are some key points to keep in mind,
precautions for product use
It is flammable, so it should be stored and used in a well-ventilated area away from open flames, sparks, and other ignition sources. Strictly adhere to the fire safety regulations and ensure that fire-extinguishing equipment is available in case of an emergency.
It is a chemical compound, and prolonged or repeated contact with skin or eyes can cause irritation. Therefore, it is essential to wear appropriate protective gear, including gloves, goggles, and protective clothing, when handling this chemical.
It may release harmful vapors if heated or exposed to high temperatures. Inhaling these vapors can be harmful to the respiratory system. It is crucial to wear a respirator or appropriate breathing protection when working with this compound.
It should be stored in tightly sealed containers and kept away from direct sunlight and heat. Prolonged exposure to light or high temperatures can degrade the compound and affect its properties.
It is not suitable for ingestion. Keep it out of the reach of children and pets to prevent accidental ingestion.
It is advisable to consult the Material Safety Data Sheet (MSDS) for DBS before handling it. The MSDS provides detailed information on the compound's hazards, safety measures, and emergency procedures, which are crucial for safe handling.
In summary, Dibutyl Sebacate requires careful handling and adherence to safety guidelines to ensure the safety of individuals and the environment. Always wear appropriate protective gear, store the compound in a safe and secure manner, and consult the MSDS for additional information.
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