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Acetyltributyl citrate
1Nonproprietary names
- USP–NFAcetyltributyl Citrate
2Synonyms and trade names
ATBC; Citroflex A-4; tributyl acetylcitrate; tributyl O-acetylcitrate
3Chemical name and CAS Registry Number
Tributyl 2-acetyloxypropane-1,2,3-tricarboxylate · [77-90-7]
UNII 0ZBX0N59RZ · PubChem CID 6505
4Empirical formula and molecular weight
C20H34O8 · 402.48
5Functional category
Plasticiser
Typical concentrations: — · Dosage forms: Solid
6Applications in pharmaceutical formulation
Used as a plasticiser for polymers in film coatings for tablets, capsules, beads and granules, including enteric and modified-release coatings based on acrylic polymers and cellulose derivatives. It is also used in polymer films and in food-contact plastics. Plasticiser levels are usually expressed relative to the polymer, typically about 10–30% w/w of the dry polymer.
7Description
A clear, colourless, practically odourless, oily liquid.
8Typical properties
- Density
- ≈ 1.05 g/cm³ at 25 °C
- Boiling point
- high (above about 320 °C at atmospheric pressure); very low volatility
- Refractive index
- ≈ 1.44 (25 °C)
- Solubility
- practically insoluble in water; miscible with acetone, ethanol and vegetable oils
9Stability and storage conditions
Stable. Store in a well-closed container in a cool, dry place.
10Incompatibilities
Incompatible with strong alkalis, which hydrolyse the ester groups, and with strong oxidising agents.
11Method of manufacture
Prepared by esterifying citric acid with n-butanol and then acetylating the remaining hydroxyl group with acetic anhydride; the product is purified by washing and distillation.
12Safety
Regarded as having low toxicity and as non-irritant at the levels used in oral coatings. It is used widely in food packaging and other consumer plastics as an alternative to phthalate plasticisers.
13Handling precautions
Observe normal precautions for the quantity handled. Gloves and eye protection are recommended.
14Regulatory status
Included in the FDA Inactive Ingredient Database (oral capsules and tablets). Permitted in the USA in certain food-contact materials.
15Related substances
Acetyltriethyl citrate; tributyl citrate; triethyl citrate.
16Comments
Acetyltributyl citrate is far less water-soluble than triethyl citrate, so it leaches less from coatings in aqueous media, but it is harder to incorporate into aqueous polymer dispersions and needs sufficient mixing time to partition into the polymer particles.