1,5-Pentanediol

Chemical properties

clear colorless oily liquid

The Uses of 1,5-Pentanediol

1,5-Pentanediol is used largely as a chemical intermediate. Industrial exposure is likely to be from direct contact.

The Uses of 1,5-Pentanediol

1,5-Pentanediol is used as a reagent in the total synthesis of (+)-Rubriflordilactone A, a nortriterpenoid natural product. 1,5-Pentanediol is also the starting material in the synthesis of Pseudomonic Acid D Sodium (P839520); an antibiotic isolated from Pseudomonas fluorescens.

Definition

ChEBI: Pentane-1,5-diol is a primary alcohol.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 1646, 1946 DOI: 10.1021/ja01212a085
Tetrahedron Letters, 21, p. 1501, 1980 DOI: 10.1016/S0040-4039(00)92757-6

Flammability and Explosibility

Not classified

Safety Profile

Mildly toxic by ingestion. A skin and eye irritant. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. Used as a plasticizer in cellulose products and adhesives, and in brake fluid.

Synthesis

1,5-Pentanediol usually is produced by catalytic hydrogenation of glutaric acid or of its esters, e.g., dimethyl glutarate, although dicarboxylic acid mixtures containing glutaric acid also may be used, giving typically a mixture of 1,4-butanediol, 1,5-pentanediol, and 1,6-hexanediol. A process using alkoxydihydropyrans as raw materials has also been reported. The crude products are purified by distillation.

Solubility in organics

1,5-Pentanediol is soluble in water, alcohols acetone, and relatively insoluble in aliphatic and aromatic hydrocarbons.