1,3-Propanediol

Catalog	BBC504632
CAS	504-63-2
Description	Liquid; OtherSolid, Liquid
Synonyms	Propane-1,3-Diol
IUPAC Name	Propane-1,3-diol
Molecular Weight	76.09
Molecular Formula	C3H8O2
Canonical SMILES	C(CO)CO
InChI	InChI=1S/C3H8O2/c4-2-1-3-5/h4-5H,1-3H2
InChI Key	YPFDHNVEDLHUCE-UHFFFAOYSA-N
Boiling Point	214 °C
Melting Point	-27 °C (lit.)
Flash Point	79.4±0.0 °C
Purity	98%
Density	1.053 g/ml
Solubility	In water, 1.0X10+6 mg/L at 25 °C (est);Miscible with water;Very soluble in ethyl ether; slightly soluble in benzene;Miscible with alcohol
Appearance	Liquid
Application	1,3-Propanediol is a versatile chemical compound known for its application in specialized performance areas due to its status as an isomer of propylene glycol. This colorless and odorless liquid boasts high miscibility with several solvents, such as water, ethanol, and acetone, which makes it valuable in a range of chemical reactions and industrial processes. Despite its higher cost, it serves critical functions as a raw material for producing 1,3-dioxanes and is utilized in the synthesis of polymers, notably poly(trimethylene terephthalate) for high-quality carpet fibers and polyester coatings. It acts as a chain extender in polyurethane elastomers and plays roles in epoxy formulations and as a rubber additive. Additionally, 1,3-Propanediol is employed in lowering the freezing point of water and as a solvent for thin film preparations. Prepared as a by-product in glycerin manufacture, it offers utility in various synthetic applications, including natural product synthesis and polymerization reactions, while its prospects in emerging markets continue to expand.
EC Number	207-997-3
pKa	14.46±0.10
Refractive Index	1.434
Solubility in Water	100 g/L
Vapor Pressure	0.04 mmHg;0.0441 mm Hg at 25 °C

Case Study

1,3-Propanediol (1,3-PDO) Used for the Extraction of Phenol from Toluene-Phenol Mixtures in Coal Tar

Yang, Chong, et al. The Journal of Chemical Thermodynamics 187 (2023): 107141.

1,3-Propanediol (1,3-PDO) has demonstrated superior performance as an extractant for the selective removal of phenol from coal tar systems containing toluene. Due to its strong hydrogen-bonding capability, 1,3-PDO forms stable associations with phenol, enabling its effective separation through liquid-liquid extraction (LLE).
In comparative ternary systems of phenol + toluene + solvent (either 1,2-PDO or 1,3-PDO), 1,3-PDO exhibited a significantly higher distribution of phenol into the extraction phase, confirming its greater affinity for phenol over toluene. Importantly, the mole fraction of 1,3-PDO in the raffinate phase was markedly lower than that of 1,2-PDO, indicating minimal solvent loss and enhanced solvent recovery during the process.
Furthermore, 1,3-PDO minimized the co-extraction of toluene into the extraction phase, reducing contamination and facilitating subsequent distillation steps. Ternary phase diagram analysis revealed that the system involving 1,3-PDO possesses a larger two-phase region than that with 1,2-PDO, indicating enhanced separation efficiency. The extraction performance of 1,3-PDO remained stable across a temperature range of 298.2-318.2 K, allowing the process to be effectively conducted under ambient conditions.
These findings establish 1,3-PDO as an optimal green solvent for phenol removal from aromatic mixtures, offering advantages in efficiency, selectivity, and process sustainability.

1,3-Propanediol Is Used for Synthesizing Bio-Based Polyols

Ruan, Mengmeng, et al. Industrial crops and products 128 (2019): 436-444.

Bio-based 1,3-propanediol (1,3-PDO) plays a pivotal role in the sustainable synthesis of aliphatic poly(1,3-propylene dicarboxylate) diols, which serve as essential building blocks for eco-friendly polyurethane adhesives. In a recent study, four types of bio-based polyols-poly(1,3-propylene adipate) diol (PPA-3500), poly(1,3-propylene suberate) diol (PPSu-3500), poly(1,3-propylene sebacate) diol (PPSe-3500), and poly(1,3-propylene dodecanedioate) diol (PPDo-3500)-were synthesized through the polycondensation of 1,3-PDO with different aliphatic dicarboxylic acids.
The reaction was carried out under argon at elevated temperatures (140-220 °C), using a trace amount of catalyst (TPT) and antioxidant (Irganox 1010). Water produced during the reaction was removed via distillation, and the process continued under vacuum until the acid value dropped below 1 mg KOH/g. The resulting diols exhibited an average molecular weight (Mn) of ~3500 Da, indicating suitability for polymeric applications.
These novel bio-based polyols demonstrate the versatility and performance of 1,3-PDO in producing renewable materials, aligning with green chemistry principles. Their potential as a component in polyurethane adhesive systems makes them attractive for industrial applications seeking to reduce environmental impact. This study highlights 1,3-PDO's crucial role in promoting the development of high-performance, bio-based polymers.

1,3-Propanediol Is Used for the Synthesis of Biodegradable Polyesters

Umare, S. S., A. S. Chandure, and R. A. Pandey. Polymer Degradation and Stability 92.3 (2007): 464-479.

1,3-Propanediol (1,3-PDO) is a key monomer employed in the bulk synthesis of biodegradable aliphatic polyesters through transesterification polycondensation reactions. In the referenced study, 1,3-PDO was reacted with various aliphatic dicarboxylic acids-including adipic, succinic, and sebacic acids-in the presence of titanium(IV) butoxide [Ti(OBu)₄] as a catalyst to prepare both homopolyesters and copolyesters.
The copolyester poly(1,3-propylene sebacate-co-1,3-propylene succinate) (PPSe-co-PPSu75) was synthesized using sebacic acid (0.75 mol), succinic acid (0.25 mol), and an excess of 1,3-PDO (1.1 mol) in a nitrogen-purged system. The reaction mixture was first heated to 170 °C for 5 hours to remove water via distillation, followed by a second-stage reaction at 240 °C under vacuum (<1 Torr) to drive the polycondensation to completion. The crude product was purified by reprecipitation in cold methanol, yielding a white solid with 95% recovery.
This synthetic route demonstrates the versatility of 1,3-PDO in constructing aliphatic polyester chains with tunable properties by varying dicarboxylic acid monomer ratios. The resulting biodegradable polymers are promising candidates for environmentally friendly materials, aligning with the principles of green chemistry and sustainable development. Thus, 1,3-PDO is an essential diol in the design of bio-based and biodegradable polyesters.