1,3-Propanediol Property

Melting point:

-27 °C (lit.)

Boiling point:

214 °C/760 mmHg (lit.)

Density 

1.053 g/mL at 25 °C (lit.)

vapor pressure 

0.8 mm Hg ( 20 °C)

refractive index 

n20/D 1.440(lit.)

FEMA 

4753 | 1,3-PROPANEDIOL

Flash point:

>230 °F

storage temp. 

Store below +30°C.

solubility 

H₂O: soluble

pka

14.46±0.10(Predicted)

form 

Oily Liquid

color 

Clear

PH

4.5-7.0 (100g/l, H2O, 20℃)

explosive limit

2.5%(V)

Water Solubility 

100 g/L

Merck 

14,9714

BRN 

969155

Dielectric constant

35.0（20℃）

InChIKey

YPFDHNVEDLHUCE-UHFFFAOYSA-N

LogP

-0.71 at 20℃

CAS DataBase Reference

504-63-2(CAS DataBase Reference)

NIST Chemistry Reference

1,3-Propanediol(504-63-2)

EPA Substance Registry System

1,3-Propanediol (504-63-2)

Safety

Hazard Codes 

Xi

Risk Statements 

38

Safety Statements 

23-24/25

WGK Germany 

1

RTECS 

TY2010000

Autoignition Temperature

405 °C

TSCA 

Yes

HS Code 

29053980

Hazardous Substances Data

504-63-2(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 15670 mg/kg LD50 dermal Rabbit > 20000 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H315Causes skin irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

1,3-Propanediol Chemical Properties,Usage,Production

Chemical Properties

1,3-Propanediol, an isomer of propylene glycol, is a viscous, colorless, odorless, hygroscopic liquid that has a brackish irritating taste. miscible with various solvents such as water, ethanol, acetone, chloroform (chloroform) and ether, and is insoluble in benzene. Combustible.

Uses

1,3-Propanediol is used as a solvent for thin film preparations, in the production of polymers such as polytrimethylene terephthalate, adhesives, laminates, coatings, moldings, aliphatic polyesters, as an antifreeze and in wood paint. It also acts as a reagent for vinyl epoxide synthon, for epoxide ring-opening, for polymerization reactions and for natural product syntheses.

Uses

As a diol, 1,3-propanediol is subject to many of the same polymeric applications as other low molecular mass diols (e.g., ethylene glycol, propylene glycol, and 1,4-butanediol). However, its relatively high price limits its use to applications requiring very specific performance characteristics. It is a raw-material source for 1,3-dioxanes. 1,3-Propanediol-bis(4-aminobenzoate) can be used as a chain extender in polyurethane elastomers. This bisbenzoate, which can also be synthesized from 1,3-dichloro-propane, finds other applications as a cross-linking agent in epoxy formulations and as a rubber additive.

Definition

ChEBI: Propane-1,3-diol is the simplest member of the class of propane-1,3-diols, consisting of propane in which one hydrogen from each methyl group is substituted by a hydroxy group. A colourless, viscous, water-miscible liquid with a high (210℃) boiling point, it is used in the synthesis of certain polymers and as a solvent and antifreeze. It has a role as a protic solvent and a metabolite.

Application

In adipate polyesters with other diols these diols are partly substituted by 1,3-propanediol (PDO) to break crystallinity in order to obtain liquid polyester polyols. In polyesters for powder coatings PDO improves the flexibility but lowers the glass transition temperature somewhat. PDO finds also uses in cosmetics and personal care products, engine coolants, and solvents for ink-jet and screen inks.

Application

1,3-Propanediol is prepared as a by-product in the manufacture of glycerin by the saponification of fat. It is used to lower the freezing point of water and as a chemical intermediate. Industrial exposure is limited. It is also used to Solvent for thin film preparations, Vinyl epoxide synthon and reagent for epoxide ring-opening and polymerization reactions, Reagent for natural product syntheses.
A new large market for 1,3-propanediol will be in polyester coatings and in the production of poly(trimethylene terephthalate), a new material for the production of high quality carpet fibers.

Biosynthesis

1,3-Propanediol (1,3-PDO) can be produced by fermentation from glycerol, with different strains such as Klebsiella pneumoniae, Clostridium butyricum, Clostridium pasteurianum, and Citrobacter freundii. Drawbacks of industrial fermentation using these strains are strong inhibition of 1,3-PDO production and by-products during fermentation.

Flammability and Explosibility

Non flammable

Synthesis

1,3-Propanediol is produced commercially by Degussa starting from acrolein.
CH2CHCHO + H2O → HOHCH2CH2CHO
HOHCH2CH2CHO + H2 → HOHCH2CH2CH2OH
The addition of water under mild acidic conditions gives 3-hydroxypropionaldehyde with high selectivity. Preferentially buffer solutions with a pH 4-5 or weak acidic ion exchange resins are used as catalysts. Further hydrogenation of this aqueous solutions gives 1,3-propanediol. There is an alternative route via hydroformylation of ethylene oxide and subsequent hydrogenation of the intermediate 3-hydroxypropionaldehyde.

Purification Methods

Dry this diol with K2CO3 and distil it under reduced pressure. More extensive purification involves conversion with benzaldehyde to 2-phenyl-1,3-dioxane (m 47-48o) which is subsequently decomposed by shaking with 0.5M HCl (3mL/g) for 15minutes and standing overnight at room temperature. After neutralisation with K2CO3, the benzaldehyde is removed by steam distillation and the diol is recovered from the remaining aqueous solution by continuous extraction with CHCl3 for 1day. The extract is dried with K2CO3, the CHCl3 is evaporated and the diol is distilled. [Foster et al. Tetrahedron 6 177 1961, Beilstein 1 IV 2493.]