Acetyl tributyl citrate
[CAS# 77-90-7]

Identification

• Classification: API >> Respiratory medication >> Antitussive
• Name: Acetyl tributyl citrate
• Synonyms: Tributyl 2-acetylcitrate; Tributyl o-acetylcitrate
• Molecular Formula: C₂₀H₃₄O₈
• Molecular Weight: 402.48
• CAS Registry Number: 77-90-7
• EC Number: 201-067-0
• SMILES: CCCCOC(=O)CC(CC(=O)OCCCC)(C(=O)OCCCC)OC(=O)C

Properties

• Density: 1.048
• Melting point: -59 °C
• Boiling point: 327 °C
• Refractive index: 1.441-1.444
• Flash point: 204 °C
• Water solubility: <0.1 g/100 mL

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Carcinogenicity	Carc.	1B	H350
Germ cell mutagenicity	Muta.	1B	H340
Flammable gases	Flam. Gas	1	H220
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Flammable liquids	Flam. Liq.	3	H226
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

Discovery and Applications

Acetyl tributyl citrate, with the chemical formula C19H30O7, is a versatile ester used primarily as a plasticizer in various industrial and consumer products. It is an acetylated ester of tributyl citrate, which itself is derived from citric acid and butanol. The compound is characterized by its ability to enhance the flexibility and durability of polymers and other materials, making it valuable in a wide range of applications.

The discovery of acetyl tributyl citrate can be traced back to the late 20th century, during a period of increased interest in developing safer and more effective plasticizers. Researchers sought alternatives to phthalate-based plasticizers due to concerns over their potential health and environmental impacts. Acetyl tributyl citrate emerged as a promising substitute because of its favorable properties and lower toxicity.

One of the primary applications of acetyl tributyl citrate is in the plastic and rubber industries. It is used to improve the flexibility, workability, and durability of polyvinyl chloride (PVC) and other polymers. By incorporating acetyl tributyl citrate into these materials, manufacturers can produce products that are more pliable and resistant to environmental stressors. This makes it ideal for use in a variety of products, including flexible flooring, medical devices, and food packaging.

In addition to its role in plastics, acetyl tributyl citrate is used in the production of adhesives, coatings, and sealants. Its presence in these formulations enhances their performance by providing better adhesion, increased flexibility, and improved resistance to degradation. This makes acetyl tributyl citrate a valuable component in industries where durability and flexibility are crucial.

Acetyl tributyl citrate is also utilized in the formulation of personal care products and cosmetics. Its low toxicity and compatibility with skin make it suitable for use in products such as lotions, creams, and hair conditioners. It functions as a carrier and stabilizer for other ingredients, ensuring that products maintain their effectiveness and stability over time.

Furthermore, acetyl tributyl citrate has applications in the production of food-contact materials. It is used in food packaging and processing equipment due to its safety profile and ability to meet regulatory requirements for food contact substances. Its use in these applications helps ensure that food products remain safe and free from contamination.

Overall, acetyl tributyl citrate is a versatile chemical with a wide range of applications across different industries. Its ability to enhance the properties of polymers, adhesives, and personal care products, coupled with its low toxicity, makes it a valuable compound in both industrial and consumer contexts.

References

2024. Facile one-step synthesis of three-dimensional network-structured polyester plasticizers with superior migration resistance in poly(vinyl chloride). Journal of Materials Science, 59(34).
DOI: 10.1007/s10853-024-10140-6

2024. New Tricarboxylate Plasticizers for Use in Polylactic Acid: Synthesis, Thermal Behavior, Mechanical Properties and Durability. Journal of Polymers and the Environment, 32(10).
DOI: 10.1007/s10924-024-03254-0

2023. Efficient analysis of toxicity and mechanisms of environmental pollutants with network toxicology and molecular docking strategy: Acetyl tributyl citrate as an example. The Science of the total environment, 904.
DOI: 10.1016/j.scitotenv.2023.167904