n-Butyryl tri-n-hexyl citrate Chemical Properties

Melting point:

−55 °C(lit.)

Boiling point:

520.24°C (rough estimate)

Density 

0.993

vapor pressure 

0Pa at 20-25℃

refractive index 

n20/D 1.448(lit.)

Flash point:

113 °C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Liquid

color 

Colorless to Light yellow

LogP

4 at 21℃ and pH5.7

EPA Substance Registry System

1,2,3-Propanetricarboxylic acid, 2-(1-oxobutoxy)-, trihexyl ester (82469-79-2)

Safety Information

HS Code 

2918.15.5000

n-Butyryl tri-n-hexyl citrate Usage And Synthesis

Uses

Trihexyl O-Butyrylcitrate is a non-toxic plasticizer, widely used in non-toxic PVC granulation, medical products, soft children's toys, ink coatings, etc.

Application

Trihexyl O-Butyrylcitrate can be used as an intermediate in pharmaceutical synthesis.

Synthesis

Trihexyl O-Butyrylcitrate was prepared as follows: 1) To a 1 liter four-neck flask equipped with a stirrer, immersion thermometer, subsurface nitrogen sparge tube and Barrett trap with condenser 330 g n-hexanol, 180 g citric acid and 50 ml heptane. The reaction mass was heated to reflux (about 120°C) with a heating mantle and 1.5 grams of tetra-n-butyl titanate esterification catalyst was added. The reaction mass was esterified at 120-140°C until the acidity was less than 2 mgKOH/g acidity. The pressure was reduced to 20 mmHg using a vacuum pump to distill off excess n-hexanol and heptane azeotrope. The ester-containing reaction mass was then stripped with fresh steam at a temperature of 130-140° C. and full vacuum until no residual n-hexanol was detected by gas chromatography.
2) The ester-containing reaction mass was cooled to 90°C, and 0.4 g of concentrated sulfuric acid was added dropwise with stirring. n-Butyric anhydride (166 g) was added dropwise with stirring, maintaining the acylation temperature between 90-110°C. The acylation reaction mixture was stirred and allowed to proceed for 2 hours to prepare the acylated ester. response quality. By-product butyric acid was removed by vacuum distillation at 110°C.

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